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The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

Harry Stebbings

The Twenty Minute VC (20VC) interviews the world's greatest venture capitalists with prior guests including Sequoia's Doug Leone and Benchmark's Bill Gurley. Once per week, 20VC Host, Harry Stebbings is also joined by one of the great founders of our time with prior founder episodes from Spotify's Daniel Ek, Linkedin's Reid Hoffman, and Snowflake's Frank Slootman. If you would like to see more of The Twenty Minute VC (20VC), head to www.20vc.com for more information on the podcast, show notes, resources and more.

1170 - 20Growth: The Six Channels Startups Need to Dominate to Grow, Why the Best Growth Talent Never Comes from Marketing or Product, Who and How to Hire Growth Leaders and Teams and Why in a World of AI, Growth is More Science than Art with Matt Lerner

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1170 - 20Growth: The Six Channels Startups Need to Dominate to Grow, Why the Best Growth Talent Never Comes from Marketing or Product, Who and How to Hire Growth Leaders and Teams and Why in a World of AI, Growth is More Science than Art with Matt Lerner
Matt Lerner is one of the OGs of growth having spent 11 years leading growth teams at PayPal. Post PayPal, Matt led the growth marketing program at 500 Startups. He is also the bestselling author of Growth Levers and How to Find Them. Today, Matt is the Co-Founder and CEO of SYSTM, an accelerator program helping startups find their growth drivers.
In Today’s Episode with Matt Lerner We Discuss:
How did Matt make his way into the world of growth?
What were Matt’s biggest lessons from 11 years at PayPal?
What did Matt know now that he wished he’d known when he entered the world of growth?
What is growth to Matt? What is it not?
Why does Matt think growth is more science than art?
Does Matt Agee with Adam Gross @ Vimeo that paid acquisition below $100M ARR isn’t PLG?
How does Matt think AI will change the world of growth today?
What does Matt think are the most common growth mistakes founders make?
Why does Matt believe there are only six types of growth channels?
What is the “locksmith moment" & how do startups find channels that work for them?
How does Matt pick a Northstar metric?
What are the most common mistakes founders make when picking North Star metrics? When is the right time to change them?
How does Matt approach horizontal product messaging? What works? What doesn’t work?
What does Matt look for in the first head of growth hire?
What questions does Matt ask when interviewing?
What were Matt’s biggest hiring mistakes? What did he learn?
Why does Matt think the best growth hires have no marketing experience?
What are Matt’s two steps to master onboarding?
What are the 3 most common patterns in leaders according to Matt?
Fri, 31 May 2024 - 55min
1169 - 20VC: Former Meta CTO, Schrep on Why Climate is a $10TRN Problem, Operating Lessons Scaling Products to Billions at Meta and Why the Best Leaders are Like Music Conductors
Mike Schroepfer (Schrep) is the Founder & Partner @ Gigascale Capital, a new kind of climate-focused investment firm. Prior to Gigascale, Mike was the CTO @ Meta where he scaled products to billions of users, shipped millions of units of consumer hardware, constructed tens of millions of sq ft of data centres, built teams of up to 35,000, and made breakthroughs in AI. Before Meta, Mike led engineering at Mozilla and founded a company acquired by Sun Microsystems.
In Today's Show with Mike Schroepfer We Discuss:
1. Lessons from Mark Zuckerberg and Meta:
What are Schrep's biggest lessons from Zuck on truly effective leaders? Why does Schrep believe the best leaders are like music conductors? What does Schrep mean when he says, "building a company is a game of inches"? Why does Schrep believe "inertia is one of the most underappreciated forces in company building?"
2. The Future of Energy:
Why does Schrep believe that the "availability of cheap, clean energy is the biggest rate limiter to human progress?" Does Schrep agree with Sam Altman that energy will be the currency of the next decade? Or does he believe Mustafa Suleyman is right and it will soon be free and abundant? How does Schrep predict the next five years for both fusion and nuclear? Why does Schrep believe the next few years will be "messy but with huge opportunity"?
3. Investing in Climate: It has to be Profitable:
Why does Schrep believe that markets and not governments or philanthropy will solve the climate challenges we face? What leads Schrep to suggest that the climate change transition is a $10TRN opportunity for investors? What is the single hardest element of investing in climate change solutions today? Why do climate change solutions need to reshape how they market to consumers? How much capital does it take to build a defensible moat in climate?
4. Schrep: The Man Behind Whatsapp and Instagram: AMA:
How does Schrep reflect on his own relationship to money? How has it changed? How does Schrep think about what it takes to be a great father? How did Schrep manage the physical stress and pressure of managing engineering for products that serve billions of people in WhatsApp and Instagram?

Wed, 29 May 2024 - 1h 10min
1168 - 20VC: Why Seed is Systemically Broken | Why Pricing is Worse Than Ever and There is More Funding Than Ever | Benchmarks for Churn, Retention and Growth Rates - Good vs Great | Why Last Vintage for Private Equity Will Suck with Jason Lemkin
Jason Lemkin is one of the OG SaaS investors with all of his first five investments turning into unicorns with Pipedrive, Algolia, Talkdesk, Salesloft and RevenueCat all in his portfolio. SaaStr is the largest global community in SaaS and he has taught a generation the fundamentals of SaaS on saastr.com.
In Today's Episode with Jason Lemkin We Discuss:
1. Growth Rates and Churn Rates: Average/Good/Great:
What is a growth rate that would excite Jason in a SaaS company? What is average? What levels of churn would worry Jason to see? What would excite him to see? What does Jason never tolerate when it comes to either growth rate or retention?
2. What Founder Combination Always Wins:
Why does Jason believe you cannot lose money on a CEO salesperson and a technical CTO founding partnership? Why does Jason always meet the CTO for a second meeting in the diligence process? What questions does he ask? What do the best CTOs do or say? Why does Jason always want to sell his shares when the founders want to sell? Why does Jason believe that a company is never the same when the founders leave?
3. WTF is Happening in the World of VC:
Why does Jason believe that pricing is worse than it has ever been in venture? Why does Jason believe that traditional seed VC is systemically broken? Why are companies getting stuffed with more cash than ever before? What does Jason know now about dilution that he wishes he had known when he started? Why does Jason believe that you should always recycle everything?
4. WTF is Happening in PE and Later Stage Markets:
What happens to all the overpriced acquisitions like Zendesk and Salesloft where private equity way overpaid for them, they have no growth and no product innovation? What happens to the generation of public companies like Box, Dropbox and Twilio, all with low growth and little product innovation in the single-digit market caps? Why does Jason believe that Klaviyo is the most undervalued public company today? What does Jason believe will happen to Anaplan with Pigment eating their lunch?
Mon, 27 May 2024 - 1h 14min
1167 - 20VC: OpenAI's Sam Altman, Mistral's Arthur Mensch and more discuss: Will Foundation Models Be Commoditised | Which Startups Are Threatened vs Enabled by OpenAI | Is the Value in the Infrastructure or Application Layer?
Sam Altman is the CEO @ OpenAI, the company on a mission is to ensure that artificial general intelligence benefits all of humanity. OpenAI is one of the fastest-scaling companies in history with a valuation of $90BN and $2BN+ in revenue.
Brad Lightcap is the COO @ OpenAI and the man responsible for the incredible scaling of sales, GTM, partnerships and business to today being over $2BN in revenue.
Arthur Mensch is the Co-Founder and CEO of Mistral AI. Since its inception in May 2023, Mistral has raised over $520M in funding from investors like Andreeseen Horowitz, General Catalyst, Lightspeed Venture Partners, and Microsoft with a current valuation of $2 billion.
Des Traynor is a Co-Founder of Intercom, and has built and led many teams within the company, including Product, Marketing, and Customer Support. Today Des leads all of Intercom’s R&D efforts, and parts of Intercom’s marketing.
Tom Hulme is a Managing Partner of GV (Google Ventures), and leads the European team. Today, GV has over $10BN in AUM and Tom has led investments in Lemonade.com (IPO), Snyk, Secret Escapes, Blockchain.com, GoCardless, and Currency Cloud (exited to Visa).
Tomasz Tunguz is the Founder and General Partner @ Theory Ventures, just announced last week, Theory is a $230M fund that invests $1-25m in early-stage companies that leverage technology discontinuities into go-to-market advantages.
Sarah Tavel is a General Partner @ Benchmark, one of the most successful and renowned venture firms in the world. At Benchmark, Sarah has led rounds in Chainalysis, Hipcamp, Medely, Rekki, Glide, Cambly and more.
In Today's Episode We Discuss:
Fri, 24 May 2024 - 21min
1166 - 20VC: Box's Aaron Levie on Predictions for the Next Wave of AI: Will Foundation Models Be Commoditised | How the Business Model of SaaS Changes Forever | Startups vs Incumbents: Who Wins | App vs Infrastructure Layer: Where is the Value?
Aaron Levie is one of the OG founders of the last two decades as the Co-Founder and CEO of Box. Today, Box does over $1BN in revenue with a market cap of $3.85BN, and has raised over $560 million from the likes of DFJ, Andreesen Horowitz, and Coatue.
In Today’s Episode with Aaron Levie We Discuss:
Why does Aaron think we are currently in a transformative window in AI?
What does Aaron think it takes to be successful in this next wave?
Which areas does Aaron think founders should be focusing on today? Where should they not?
How does Aaron think AI will change how we work & run a business?
What does Aaron think is the single biggest obstacle to AI adoption in large organizations?
Does Aaron agree with Sarah Tavel @ Benchmark AI companies will be selling work not tools?
How does Aaron think AI will change the SaaS business model?
Why is Aaron not as worried about AI regulation? What are his biggest concerns today?
Why does Aaron believe the next big breakthrough in AI will be agents?
How does Aaron think AI agents will change org structures?
How does Aaron think agents will differ from RPA? How will RPA companies benefit from AI?
What does Aaron think AI agents will look like in five years?
What is Aaron’s advice to startups today building against OpenAI?
Does Aaron think startups have more advantage in foundational models or the application layer?
What advantages do incumbents have? What are their biggest weaknesses?
Who does Aaron think are the biggest winners in AI today? Who is underperforming?
Why does Aaron think Apple isn’t losing the AI race?
Wed, 22 May 2024 - 56min
1165 - 20VC: Palo Alto Networks CEO Nikesh Arora on How to Create and Sustain Competitive Advantage and Defensibility | What Makes Masa Son a Genius Investor of Our Time | How the Best Leaders Communicate and Delegate
Nikesh Arora is the CEO @ Palo Alto Networks, the leading cybersecurity company in the world with a market cap of $102BN. Before joining Palo Alto Networks, Nikesh was the President and COO of SoftBank Group. Before that, he spent ten years at Google as a senior exec, and President of Europe, the Middle East and Africa. Before that Nikesh was CMO for the T-Mobile International Division of Deutsche Telekom AG. Nikesh serves on the board of Compagnie Financière Richemont S.A. Previously, he served on the boards of SoftBank, Sprint, Colgate-Palmolive Inc., Yahoo! Japan and Tipping Point.
In Today's Episode with Nikesh Arora We Discuss:
1. From Investing with Masa @ Softbank to CEO of Largest Cyber Company:
What are Nikesh's biggest lessons from working and investing with Masa @ Softbank? What are Nikesh's biggest takeaways from 10 years at Google and working with Eric Schmidt? What does Nikesh know now that he wishes he had known when he started his career?
2. What Makes the Most Valuable Businesses in the World:
How does Nikesh think about competition and monopolies? How does Nikesh assess the idea of defensibility, moats and sustaining competitive advantages? What are the most common reasons why incumbents are overtaken? How have Palo Alto Networks been so successful in their M&A strategy? What has worked in M&A? What has not worked? What is their process?
3. What Makes the Best Leaders in the World:
Does Nikesh agree that the best CEOs are the best resource allocators? How do the best leaders communicate with large teams at scale? How do the best leaders approach decision-making? What is Nikesh's framework? How does Nikesh approach the idea of delegation? What does he delegate vs what does he not?
4. Behind the CEO: Nikesh Arora: Husband and Father:
How does Nikesh reflect on his own relationship to money today? What are Nikesh's biggest lessons in what it takes to bring children up in a world of affluence and ensure they have hunger and ambition? What are some of Nikesh's biggest lessons on parenting? How does Nikesh reflect on what it takes to have a great marriage?

Mon, 20 May 2024 - 52min
1164 - 20Product: How Linktree, Webflow and Airbnb Used Rituals and Product Principals to Guide Product Roadmap, Why All Product Teams Should Have a Scorecard and How to Use it & How to Run the Best "Product Jams" with JZ, CPO @ Linktree
Jiaona “JZ” Zhang is the Chief Product Officer at Linktree, the world’s leading link-in-bio platform empowering 45M+ creators, brands and SMBs. JZ joined Linktree from Webflow, where she served as SVP of Product. Before that, she spent four years at Airbnb where she built and led numerous teams on the host side. JZ’s also held leadership roles at the likes of Wework, Dropbox and teaches at Stanford University and Reforge.
In Today’s Episode with Jiaona Zhang We Discuss:
How did JZ first fall in love with product?
Why does JZ believe the best PMs have experience in the gaming industry?
Does JZ think Linktree could be a $100BN business? How could Linktree become a $100BN business?
Why does JZ think product is the most chameleon role? Where does product start & end?
Why does JZ think every function should have tension with product?
What is a KPI tree? How does JZ branch business & product metrics?
When does JZ think startups should set up a metric infrastructure?
What are the three levers of product? How does JZ determine which ones to trade off?
Why does JZ think planning should not exist?
What are strategy and rituals? When should founders do either?
What are JZ’s three core rituals?
What is the scorecard method? How do they help team transparency?
What are product jams? When does it work? When does it not work?
When does JZ think founders hire a product person?
What are the most common mistakes early stage founders make when hiring for product?
Does JZ think domain expertise is important? What does she look for in product hires?
What is JZ’s advice to PMs who want to get promoted today?
What is JZ’s advice to young people who want to get into product?
Fri, 17 May 2024 - 1h 01min
1163 - 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless
Dan Siroker is the Co-Founder and CEO @ Limitless, a personalized AI powered by what you’ve seen, said, or heard. For his latest funding round, Dan took an unusual approach resulting in 1,000 preliminary offers with valuations as high as $1BN — and resulted in a $350 million Series A valuation. Prior to founding Limitless, Dan was the Founder of Optimizely, scaling the company to $120M in ARR and raising from some of the best in the business including Peter Fenton @ Benchmark who led the Series A.
In Today's Episode with Dan Siroker We Discuss:
1. Serial Entrepreneurs are More Investable:
Why would Dan always prefer to invest in serial entrepreneurs than first time founders? How do serial entrepreneurs approach team building and size of team differently? How do serial entrepreneurs approach focus and prioritisation differently? How do serial entrepreneurs approach pivoting differently to first time founders? What is Dan's advice from Elad Gil and YC's Dalton Caldwell on when to pivot?
2. The Secret to Fundraising: How to Speak VC
Should founders always be raising? What is the right thing to respond to investors when they reach out to you outside of a round? What question are investors really asking when they ask, how much are you raising? How should founders approach valuation, what should they say when they are asked for it? How can founders create urgency in a funding round? What works? What does not?
3. How to Raise the Best Funding Round:
Should founders engage with associates or only worth it with decision-makers? Why should founders always choose the investor who is on the early arc of their career? Why was Dan's first meeting with Peter Fenton the best meeting he has ever had with a VC? Why does Dan believe that taking the highest price is never the right answer? To what extent does having a true Tier 1 VC lead your round, change the game for your company?
4. Dan Siroker: AMA:
How did becoming a father change the way that Dan operates? Why is Dan scared we might see technological progress stall for the next 20 years? Why did Dan not do YC the second time around with Limitless? What is the story of how Optimizely nearly bought Amplitude?

Wed, 15 May 2024 - 1h 16min
1162 - 20VC: Behind the Scenes at Y Combinator: The Interview Process | What the Best & Worst Do in the Program | Do the Best All Raise Pre-Demo Day & YC's Fundraising Advice to Startups | Why the Value is in Application Layer AI with Tom Blomfield
Tom Blomfield is a Group Partner at YC. Before YC, Tom founded two unicorns in the UK. He was co-founder of Monzo (most recently valued at $5BN), one of the first challenger banks in the UK. Monzo raised more than £1bn and counts 15% of the UK population as customers. Before Monzo, Tom founded GoCardless (YC S11), an online payments processor, most recently valued at $2.1BN.
In Today's Episode with Tom Blomfield We Discuss:
1. From Founding Two Unicorns to YC Partner:
Does Tom believe that all great founders show signs of exceptionalism early? What does Tom know now that he wishes he had known when he started his first company? Why did Tom decide now was the right time to switch from founder to investor with YC?
2. The YC Application Process: How it Works:
How do the YC partners select which companies are accepted vs rejected? What specifically does Tom look for in the problem the company is looking to solve? In the interview, what are the signals of the highest quality founders? What questions does Tom always want to ask in YC interviews with founders?
3. The YC Batch: How it Works:
How do the YC partners work with the 25 companies in their batch? What is the interaction? What are the single biggest mistakes companies make while in YC? What are the biggest pieces of advice YC gives founders on fundraising approaching demo day? How do the best YC founders fundraise and use demo day? How do the most nervous fundraise? How are YC partners measured in terms of their success and effectiveness?
4. AI: Consumer vs Enterprise/ Infrastructure vs Application Layer:
Does Tom believe there is money to be made investing in infrastructure layer models today? Why is the commoditization of foundation models the best outcome for society? Why is Tom most excited about the application layer for the next wave of AI? What are the most exciting opportunities in consumer AI that are wide open today?
20VC: Behind the Scenes at Y Combinator: The Interview Process | What the Best & Worst Do in the Program | Do the Best All Raise Pre-Demo Day & YC's Fundraising Advice to Startups | Why the Value is in Application Layer AI with Tom Blomfield
Mon, 13 May 2024 - 1h 04min
1161 - 20Sales: How to Build Vertical Sales Teams, Why No Customer Success is BS and Everyone Needs it, How to Hire, Train and Retain the First Reps and Lessons Scaling to $2.1BN Revenue and 1,300 People with Larry Schurtz, CRO @ Genesys
Larry Shurtz is the Chief Sales Officer at Genesys where he oversees the company’s global go-to-market strategies, including commercial activities, field sales and partner ecosystem operations. Larry has nearly three decades of experience in the software industry, from leading Confluent to delivering more than 60% revenue growth and doubling customer count as Chief Revenue Officer, to scaling a 1,300-person team at Salesforce to $2.1 billion in revenue.
In Today’s Episode with Larry Shurtz We Discuss:
How did Larry lead 1300 people to $2.1 billion revenue at Salesforce? What were his takeaways?
What did Larry learn about building vertical sales playbooks at Salesforce?
Which framework did Larry learn at Salesforce that he still uses at Genesys?
What are the biggest mistakes sales leaders make on prioritization today?
What are Larry’s “3 Rs” to master prioritization?
What does Larry think are the most common reasons fast-scaling teams break in sales?
Has Larry ever caused bad culture in a sales team? What did he learn from the experience?
Does Larry think sales is more art or science? How does Larry blend the two?
How does Larry structure the hiring process for a new sales hire?
How big should your recruitment team be?
What are Larry’s most commonly asked questions when interviewing?
What were Larry’s biggest hiring mistakes? What did he learn from them?
How does Larry structure the comp? How does he get it right? What do most new hires care about today?
How does Larry structure the onboarding process?
Why does Larry onboard new hires with big customers? What is the buddy system?
How does Larry tell if a new hire is bad? What are the biggest red flags to look out for?
What does Larry mean when he says “You can make all the physical errors, you cannot make mental errors?”
Does Larry agree with Max Levchin @ Affirm that “When there’s doubt, there’s no doubt?”
Fri, 10 May 2024 - 55min
1160 - 20VC: GV's Tom Hulme on Why Investing in Foundation Models is like Investing in "Power Stations", The Conventional Wisdom in VC that is BS & Lessons from a 24x Angel Track Record, 255x on Robinhood and Making Billions on Uber
Tom Hulme is a Managing Partner of GV (Google Ventures), and leads the European team. Today, GV has over $10BN in AUM and Tom has led investments in Lemonade.com (IPO), Snyk, Secret Escapes, Blockchain.com, GoCardless, Blue Vision Labs (exited to Lyft), and Currency Cloud (exited to Visa). Prior to joining venture full-time, Tom was one of Europe's most successful angel investors with a 5x DPI track record and 20x+ TVPI.
In Today's Episode with Tom Hulme We Discuss:
1. Lessons from a 24x TVPI Angel Track Record:
What are Tom's biggest lessons from his biggest winners angel investing? What are Tom's biggest takeaways from the 0's in his angel track record? What is the biggest advice Tom would give to angel investors starting out today? What are the single biggest mistakes Tom sees angel investors make today?
2. The Four Pillars of Venture Capital:
What does Tom believe are the four key components of being successful as a VC? Why does Tom describe VC as "being a founder on anti-depressants"? How does Tom categorise the three different types of investors that exist? Sourcing, selecting, servicing: What is Tom best at and what is he worst at?
3. The Conventional Wisdom in Venture That is Not True:
Why does Tom believe it is BS that you should never sell your winners? Why does Tom believe he has never had complete conviction in any of the companies he invests in? Why does Tom believe the "everything has to be a fund returner mindset" is BS? Why naivety doesn't lead to great founders? Why employees at rocketships are the best founders?
4. AI: Foundation Models, Generative AI, The Incumbents: Where Does the Value Go:
Does Tom believe there is money to be made investing in foundation models? Why does Tom liken investing in foundation models to investing in power stations? Where does Tom believe there is value in the application layer? Why does Tom think that generative AI is largely a sustaining innovation? Why does Tom think Microsoft will win the next wave of AI? Who else is well-positioned? Why does Tom believe there is a correlation between those that fear monger around AGI and those that need funding for their businesses?

Wed, 08 May 2024 - 1h 17min
1159 - 20VC: Benchmark's Sarah Tavel on Are Foundation Models Commoditising | Why Frontier Models Will Be Closed Source | Why the Value is in the Application Layer | The Future of AI is "Selling the Work" Not the Tools
Sarah Tavel is a General Partner @ Benchmark, one of the most successful and renowned venture firms in the world. At Benchmark, Sarah has led rounds in Chainalysis, Hipcamp, Medely, Rekki, Glide, Cambly and more. Prior to Benchmark, Sarah was a Partner at Greylock Partners. Before Greylock, Sarah was the first 30 employees at Pinterest. Sarah joined Pinterest in 2012 after co-leading the Series A investment while at Bessemer Venture Partners.
In Today's Episode with Sarah Tavel We Discuss:
1. Becoming a GP at The Most Renowned Firm in Venture:
How did the process of Sarah joining Benchmark start? How did it progress? What was it that convinced her to leave Greylock and join Benchmark? What does Sarah believe makes Peter Fenton the world-class investor that he is? What does Sarah know now that she wishes she had known when she started in venture?
2. Foundation Models: Is it All Going to Zero:
Will foundation models be commoditised? Will 99% of the funding going to foundation models go to 0? How does Sarah view the future of open vs closed source? Why does Sarah believe that all frontier models of the future will be closed-source? Why does the business model of foundation models remind Sarah of the food delivery business?
3. Application Layer: Where $BN Companies Will Be Built:
Why does Sarah believe that sustainable value-creating companies will be in the application layer? How does Sarah determine between a wrapper on top of ChatGPT and true product value? Are enterprises opening real budgets for AI today or are we still in experimental budgets? How does Sarah think about how AI companies differentiate when there are so many in the same space of customer service, sales team support etc etc? Why does Sarah believe that it is rational to pay more for these companies when investing in them? What does Sarah mean when she says the future is "selling the work and not the tools"?
4. Inside Benchmark: How the Best Do Venture:
What is the one rule that Benchmark is willing to break when doing a deal? Why do Benchmark aim to be the best recruitment firm in the world? Why do Benchmark not agree with the concept of reserves? In a case where Benchmark have lost, why did they lose? How did they change their approach?
Mon, 06 May 2024 - 1h 00min
1158 - 20VC: The Memo: Keith Rabois and Ramp's Eric Glyman on Behind The Scenes at The Best Run Private Company on the Planet; The Tools, Tips, Secrets and Process That Drive Efficiency
Eric Glyman is the Co-Founder and CEO of Ramp, America's fastest growing corporate card and finance automation platform. Under Eric’s leadership, Ramp has raised more than $1 billion in financing, with a valuation of $8.1 billion. Prior to Ramp, Eric co-founded Paribus, a price-tracking app to help consumers save money (acquired by Capital One). Ramp recently raised another $150 million series D round co-led by Founders Fund and Khosla ventures, with a post-money valuation of $7.65 billion.
Keith Rabois is a Managing Director @ Khosla Ventures and one of the most respected venture investors of the last decade. Keith has led investments in Stripe, Faire, Ramp, Affirm and many more. Prior to Khosla Ventures, Keith was General Partner at Founders Fund, where he led investments for Ramp, Trade Republic, and Aven.
In Today’s Episode with Eric Glyman and Keith Rabois We Discuss:
How did the first Founders Fund deal come to be? How was the first meeting?
What does Keith mean when he says Ramp has the “secret sauce” to be successful?
What are 1-2 things Keith thinks Eric is world-class at? What are 1-2 things Eric thinks Keith is world-class at?
How did the latest Khosla deal come to happen?
How is Eric so good at executing at Ramp? What is his biggest advice to founders on speed of execution?
What are Eric’s biggest challenges in the next 12 months at Ramp?
Why does Keith believe momentum is crucial for early stage startups? What are some easy ways founders can build momentum?
How does Eric think AI will accelerate Ramp and the world of finance?
What are Keith’s biggest lessons from Brian Chesky @ Airbnb?
What did Keith learn from Jack Dorsey @ Square about leadership?
What does Eric think founders today should build? What should they not build?
What did Eric learn from Keith on how founders should measure time & progress?
How did Ramp build a solid talent team? What did they do differently?
Does Keith & Eric believe it is better to hire externally or promote internally? What is the right balance?
Does Keith agree founders should hire & get out the way or micromanage?
How many direct reports does Keith think is enough?
Fri, 03 May 2024 - 42min
1157 - 20VC: Mark Suster on The Biggest Fundraising Lessons for VCs, Why the Correction in Venture is Still to Come, Why Private Equity Will Replace IPOs and M&A as the Exit Path & The Woke Left and a Trump Administration; What Happens?
Mark Suster is a General Partner @ Upfront Ventures, one of LA's leading early-stage venture firms. Prior to leading Upfront, Mark was a serial entrepreneur having founded two software companies, selling both with the last selling to Salesforce.com. Mark is also a prolific writer and one of his favourite pieces, Lines Not Dots is one for the ages.
In Today's Episode With Mark Suster We Discuss:
1. From Serial Entrepreneur to Leading VC:
How Mark made his way into the world of venture having sold two prior companies? What does Mark know now that he wishes he had known when he started in venture? What advice does Mark give to all young investors starting their career today?
2. How to Raise a Fund:
What are Mark's single biggest lessons from 15 years of fundraising for funds? Should managers look to institutions or friends and family first? Are LPs sheep? Do institutions anchoring funds lead to many others jumping in? What is the right amount to do a first close on? What is the right way to message the first close? What are the single biggest mistakes Mark sees managers make when raising?
3. Exit Environments are F******: What Now:
Why are IPOs not the liquidity events that everyone thinks they are? When does Mark believe IPO windows will open again? How does Mark evaluate the M&A landscape today? With little M&A and IPO activity, why does Mark believe private equity will step into their shoes? With the change to private equity being the buyer, what does that mean for the sale price of the assets? What does that mean for the future of venture returns?
4. Trump, The Woke Left and The World Around Us:
Is Mark concerned about the potential of Trump winning the election? Would Mark rather a Biden administration as the alternative? Why is Mark so worried by the woke left? Does Mark always believe there has been this deep-seated anti-semitism in the US education system? What can be done to remove this from our education system?

Wed, 01 May 2024 - 58min
1156 - 20VC: Mistral's Arthur Mensch: Are Foundation Models Commoditising | How Do We Solve the Problem of Compute | Is There Value in the Application Layer | Open vs Closed: Who Wins and Mistral's Position
Arthur Mensch is the Co-Founder and CEO of Mistral AI. Since its inception in May 2023, Mistral has raised over $520M in funding from investors like Andreeseen Horowitz, General Catalyst, Lightspeed Venture Partners, and Microsoft with a current valuation of $2 billion. Before founding Mistral, Arthur was a research scientist at DeepMind, one of the leading AI institutions in the world.
In Today’s Episode with Arthur Mensch We Discuss:
What were Arthur’s biggest lessons from his time at DeepMind?
How did DeepMind shape how Arthur built Mistral?
Why does Arthur believe smaller teams are better for AI?
Why did Arthur decide to leave DeepMind and start Mistral?
What made Mistral 7B so successful? What did Arthur learn from the model release?
What are the biggest barriers at Mistral today?
How does Arthur balance the sales and research teams at Mistral?
What does Arthur know now that he wishes he had known when he started Mistral?
Why did Arthur open-source some models? Why did he close some?
How quickly will the cost of compute go down? Why does Arthur believe marginal costs will not go to zero?
How will open-sourcing LLMs affect the marginal cost?
Does Arthur think open source is ready for enterprise adoption?
What questions should enterprises be asking about AI adoption today?
What are the biggest challenges to AI adoption today?
What does Arthur think are the largest bottlenecks of model quality today?
Does Arthur think future models will be more generalized or vertical-focused?
What does Arthur think about the future of commoditization in models?
Why is Arthur optimistic about the profitability of the application layer of AI?
How should models differentiate themselves today?
Mon, 29 Apr 2024 - 49min
1155 - 20Growth: Inside Dropbox, Salesforce & Heroku's Product-Led Growth Engine; What Works & What Doesn't | Why Startups Doing Paid Under $100M ARR are not PLG | Why PLG is a Business Model, Not a Go-To-Market Motion with Adam Gross, Former CEO @ Vimeo
Adam Gross is one of the masters of product-led growth (PLG). Most recently, Adam was Vimeo's interim CEO. Before Vimeo, Adam was CEO of Heroku, which he joined after selling his startup, Cloudconnect in 2013. Additionally, Adam has held executive leadership roles at Salesforce and Dropbox, and has been an active angel investor & advisor to companies, including Buildkite, Cribl, and Tailscale.
In Today’s Episode with Adam Gross We Discuss:
What were Adam’s biggest takeaways from his time at Salesforce? How did it shape his growth mindset?
What did Adam learn about customer acquisition at Dropbox?
What would Adam most like to change about growth today?
What is growth? What is it not? What do founders get wrong about growth?
Why does Adam think PLG is not for everybody?
What do most great PLG businesses have in common?
How are value propositions segmented in PLG? How can startups transition from individual to enterprise clients?
Why does Adam think startups doing paid acquisition sub $100M aren’t actually PLG?
What are the most common reasons fast-growing companies plateau?
How does Adam advise founders on diversifying channels?
What are the biggest mistakes founders make when scaling into enterprise?
How should startups do effective product marketing in horizontal products?
What is emotive & strategic marketing? How should startups balance both?
What are Adam’s top 3 pieces of advice for founders?
What does Adam mean when he says you are either hiring a poet or a librarian?
What are the biggest mistakes founders make when hiring?
What was Adam’s biggest investment miss? What did he learn from it?
Fri, 26 Apr 2024 - 41min
1154 - 20VC: Is Speed the Most Important Thing from 0-1 | Why Hiring Inexperienced People is Better | The Biggest Lessons Scaling Zip to $1.5BN Valuation with Rujul Zaparde, Co-Founder and CEO @ Zip
Rujul Zaparde is the Co-Founder and CEO of Zip, the world’s leading Intake-to-Pay solution, adopted by leading enterprises and startups including Snowflake, Canva, Airtable, Webflow, and others. In 2023, Zip raised $100 million in a Series C round, valuing the company at $1.5 billion. Before founding Zip, Rujul was a Visiting Partner at Y Combinator and a product manager at Airbnb.
In Today’s Episode with Rujul Zaparde We Discuss:
How did Rujul’s first company fail? What were his lessons?
What did Rujul learn from his time at Airbnb?
How did Rujul come to co-found Zip? What was the aha moment?
What did Rujul wish he’d known when he started Zip?
Why did Rujul pick such a competitive market? How did they stand out?
Does Rujul think founders should focus on pain points or platform solutions on day one?
What is Rujul’s advice to founders who are in the discovery process?
Does Rujul agree with Trae Stephens @ Founders Fund that serial entrepreneurs doing B2B enterprise SaaS are wasting their talent?
Which key moment caused Zip to accelerate?
Why does Rujul think speed is the most important element in startups?
Why does Rujul not believe in design partners?
Why does Rujul believe repeatability is the most important thing when pitching?
Does Rujul think AI will destroy outbound sales?
What was Rujul’s “rude awakening” building a sales team?
What was Rujul’s biggest hiring mistake? What did he learn from it?
How does Rujul decide where to focus his attention and resources?
Why does Rujul believe younger managers are more creative?
Wed, 24 Apr 2024 - 56min
1153 - 20VC: UiPath: The 10 Year Bootstrapping Journey that Turned into a $10BN Public Company | From a Dollar a Day to Romania's Richest Man | Happiness, Wealth, Risk and more with Daniel Dines, Co-Founder @ UiPath
Daniel Dines is the Co-Founder @ UiPath, one of the most incredible journeys in startups. For 10 years, UiPath was a bootstrapped company that scaled to just $500K in revenue. Then it all changed, product market fit became obvious and the rest is history. The company went on to raise funding from Sequoia, Accel, Kleiner Perkins and more. Today, the company is worth over $10BN, listed on the NASDAQ and does $1BN+ in revenue.
In Today's Episode with Daniel Dines We Discuss:
1. From a Dollar a Day to Romania's Richest Man:
How would Daniel's parents and teachers have described the young Daniel? How did Daniel first learn to code? Why was his first programming job on $300 per month the best? How did Daniel learn English by playing bridge with his friends? What was the a-ha moment for Daniel with UiPath?
2. Becoming a Billionaire: The Mental Journey:
What does Daniel mean when he says everyone is a prisoner of their own mind? How does Daniel reflect on his own relationship to money? How did having absolutely nothing impact Daniel's relationship to risk? Why does Daniel think that he does not really experience or feel happiness?
3. 10 Years to $500K ARR: The Miracle Bootstrapping Journey:
After 10 years, UiPath had just $500K in ARR, what was the one single moment that changed everything in 2014? How did raising the seed round change everything for Daniel? How did it change his approach to operating? What was the impact of having Sequoia invest? Does it change the game? Why did Daniel say no to them the first time they tried for the Series B?
4. Journey to a $10BN Public Company: The Crucible Moments:
How did the company almost go bust when it spent $400M against a plan of $150M in 2021? What is the single proudest moment Daniel has of the 19 year journey with UiPath? What have been Daniel's biggest management lessons in scaling UiPath to $1BN in ARR? Knowing all that Daniel does today, what would he have done differently about the UiPath journey?
Mon, 22 Apr 2024 - 1h 25min
1152 - 20VC: Three Core Lessons Scaling Freshworks to a $5.2BN Market Cap | Biggest Product and Pricing Lessons from Scaling to $597M in ARR | How India Can Compete Globally in Tech and AI with Girish Mathrubootham, Co-Founder @ Freshworks
Girish Mathrubootham is the founder and CEO of Freshworks, India’s first SaaS company to list on NASDAQ. Today, Freshworks has over $596M in ARR with a $5.27BN market cap, with investors like Accel Partners, Sequoia Capital, Tiger Global Management, and CapitalG. Girish is also a founding member of SaaSBOOMi, Asia’s largest community of founders and product builders, and has invested in over 60 startups. On top of that, Girish is also the Founder of Together Fund, a $150M fund focusing on Indian B2B companies going global from day 1.
In Today’s Episode with Girish Mathrubootham We Discuss:
How did a horrible customer service experience prompt Girish to start Freshworks? What was the aha moment?
What were Girish’s biggest challenges founding Freshwork in 2010?
How was building the first product? What worked? What didn’t work?
Why does Girish believe Indian companies have to win globally before winning India?
What were Girish’s biggest mistakes scaling Freshworks? What were his lessons?
Why does Girish believe starting high and going down never works in software?
When does Girish think is the best time to build the second product?
How did Freshworks lose against Slack? What did he learn from the experience?
How has Girish’s leadership style changed over time?
What were Girish’s biggest hiring mistakes?
What was Girish’s biggest challenge in building culture during COVID?
What is one piece of advice Girish believes every CEO should follow?
Why does Girish believe now is the time for India tech?
What are the most common misconceptions of India tech?
What traits does Girish look for in founders he invests in?
What was Girish’s biggest investment mistake? What did he learn from it?
Fri, 19 Apr 2024 - 49min
1151 - 20Product: Sequoia's Product-Market Fit Framework | Why the Best Product People Actually Build Less Product | Metrics 101, Good vs Great Product Strategy and more with Vickie Peng, Product Partner @ Sequoia Capital
Vickie Peng is a Product Partner at Sequoia and the co-creator of Arc, their company-building immersion programme for pre-seed and seed stage founders. Prior to Sequoia, Vickie was a product manager at Polyvore (acquired by Yahoo for $200M) and Instagram, where she grew SMB advertising from $200M to $1BN.
In Today’s Episode with Vickie Peng We Discuss:
How did Vickie make her way into the world of product?
How did Vickie turn a small side business into a massive revenue machine at TrialPay?
How did Vickie scale Instagram SMB ads to $1BN? What were her takeaways?
What was Vickie’s business model at Polyvore that eventually led to the $200M acquisition by Yahoo?
What does Vickie believe are the biggest mistakes early stage founders make when telling stories?
Which 2 components does Vickie believe every great product mission should include?
How should pre-product-market fit founders set their north star metric?
What was Vickie’s biggest product mistake? What were her lessons?
Why does Vickie think the best product people build less product?
What is Vickie’s advice to product leaders starting their first day on the job?
What are the most common mistakes founders make when hiring product teams?
Why does Vickie believe product-market fit is a journey not a destination?
What are the biggest reasons founders fail to get product-market fit?
What are the 3 types of product-market fit?
How does Vickie advise founders to differentiate themselves in competitive markets?
What is Vickie’s framework for competing against incumbents?
Wed, 17 Apr 2024 - 49min
1150 - 20VC: OpenAI's Sam Altman and Brad Lightcap on The Future of Foundation Models: Will They Be Commoditised | How to Solve the Problem of Compute | Open vs Closed: Which Dominates and Why | Which Companies and Verticals Will Be Steamrolled by OpenAI
Sam Altman is the CEO @ OpenAI, the company on a mission is to ensure that artificial general intelligence benefits all of humanity. OpenAI is one of the fastest-scaling companies in history with a valuation of $90BN and $2BN+ in revenue. Prior to OpenAI, Sam was the President and CEO @ Y Combinator and made angel investments in the likes of Airbnb, Stripe, Reddit, Pinterest, Asana and more.
Brad Lightcap is the COO @ OpenAI and the man responsible for the incredible scaling of sales, GTM, partnerships and business to today being over $2BN in revenue. Before OpenAI, Brad was an investor at Y Combinator, where he met Sam and before that led finance and operations initiatives at Dropbox.
In Today's Episode with Sam Altman and Brad Lightcap We Discuss:
1. The Partnership: The Most Powerful Double Act in Tech:
How did 25 people rejecting OpenAI's CFO positions 6 years ago, lead to Brad joining OpenAI before Sam even did? What did he see that the world did not? What does Brad think is Sam's biggest superpower that the world does not know? What does Sam think it Brad's biggest superpower that the world does not now? How do decisions get made between Brad and Sam? How do they decide what to delegate vs what not to? What is the most recent disagreement they had? How did they resolve it?
2. The Next 12 Months for OpenAI: Bottlenecks, Compute and Commoditisation:
What are the core bottlenecks facing OpenAI in the next 12 months? How does Sam believe we solve the fundamental problem of compute? What is the single biggest barrier to the quality of models improving? What is the end state for the model landscape? Will models become commoditised?
3. OpenAI: The Fastest Scaling Company in History:
What has been the secret to how OpenAI has scaled to $2BN in revenue in 24 months? Why does Sam believe that he is "not a great operator"? What drives this thinking? What have been the first things to break in the scaling of OpenAI? What do Brad and Sam know now about the scaling that they wish they had known at the start? Why does OpenAI lean towards hiring more experienced people in the team?
4. How to Invest and Operate in a World of OpenAI:
What single question can founders ask that will reveal if they will be steamrolled by OpenAI? Does Sam believe huge numbers of companies will be steamrolled by OpenAI? For investors, is there money to be made investing in the application layer of AI today? What question should all businesses be asking about how to adopt and use AI in their business?
5. Sam Altman: AMA:
What have been the single biggest lessons Sam has learned from the founders he has invested in? Which founders has he learned the most from? What did he learn from each? What is Sam most concerned about in the world today? Why what? What unexpected traits or characteristics does Sam most look for in the founders he invests in? Why does Sam say that he is not happy but he is grateful?

Mon, 15 Apr 2024 - 49min
1148 - 20Sales: The Biggest Sales Lessons Scaling Brex to $400M ARR, Why Startups are Doing Outbound Wrong and How to Fix It & Why Demand Gen is the Bottleneck for all Startups and How to Solve it with Sam Blond, Former CRO @ Brex
Sam Blond is the former CRO at Brex, where he led the company from near $0-$400M in ARR and a $12.5B valuation. Before Brex, Sam was VP of Sales at Zenefits, where he led the company from $0-$70M ARR in 2 years and a $4.5B valuation. Sam joined Founders Fund as a Partner in 2022 and recently left to focus more on operating.
In Today's Episode with Sam Blond We Discuss:
1. Lessons From Scaling Brex to $400M ARR & Zenefits to $70M ARR:
What are the secrets that very few people know, that led to the success of Brex and Zenefits? What was the single worst sales investment Brex made? What was the best? What are Sam's biggest tips to people picking the rocketship they will join?
2. Who, What and When to Hire:
When is the right time to hire your first sales rep? Should the founder be the one to create the sales playbook? What is the right profile for the first sales hire? Does it matter if the new hire has domain experience? Why does Sam always advocate to hire through network and not recruiters?
3. How to Hire the Best Sales Reps:
What are the questions Sam always asks in interviews with sales hires? Does Sam do case studies with candidates? What is he looking for? What are the biggest green and red flags a candidate can show in an interview process? What are the biggest mistakes founders make when hiring sales teams?
4. How to Have the Best Performing Sales Team:
What are the three ways to measure the success of a rep in the first 30-60 days? Why does Sam believe most startups are doing outbound wrong? What should they change? Why does Sam believe demand gen is the bottleneck for all companies? What can be done to solve the demand gen challenge? How does outbound change in a world of AI?
Fri, 12 Apr 2024 - 1h 14min
1147 - 20VC: Are the Best CEOs the Best Fundraisers, Are the Best Founders Insiders or Outsiders to a Problem, Why Ownership Should Not Be a Focus in VC & The Biggest Lessons Scaling MongoDB to $26BN Market Cap with Kevin Ryan, Founder @ AlleyCorp
Kevin Ryan is one of the leading serial entrepreneurs and investors in New York. Previously he co-founded MongoDB, Business Insider, Gilt Groupe, Zola, Nomad Health, Pearl Health, and was the CEO of DoubleClick (Acquired by Google for $3.1B). Today, Kevin is the founder and CEO of AlleyCorp, a venture capital firm that incubates and invests in transformative companies in healthcare, diversified tech, robotics, and impact. Just yesterday, Alleycorp announced their $250M fund, their first ever external capital.
In Today’s Episode with Kevin Ryan We Discuss:
How did Kevin’s early life shape his career? How would his parents and teachers describe him?
Does Kevin agree that successful entrepreneurs always show signs early?
What does Kevin think about luck vs. skill? Why does Kevin think that most things are out of your control as an entrepreneur?
Does Kevin agree the best CEOs are also the best fundraisers?
What were Kevin’s biggest lessons from scaling DoubleClick from 20 to 2000 employees?
What was Kevin’s a-ha moment behind Business Insider? What was the reason behind its success?
Why does Kevin believe the best founders are always in unfamiliar fields?
How does Kevin allocate resources between incubations vs. investments?
What are the biggest commonalities between successful companies at AlleyCorp?
Is Kevin a market-led or people-led investor?
What does Kevin think is the most important element in achieving product-market fit?
What was Kevin’s biggest miss on selecting founders? What were his takeaways?
Why does Kevin believe venture is more competitive now than ever before?
What does Kevin know now that wish he’d known when he started investing?
Does Kevin agree rich investors make better investors?
Why does Kevin not care about ownership?
Does Kevin agree with Doug Leone that venture has transitioned from a high boutique margin industry to a low margin commoditised industry?
Does Kevin agree with Peter Fenton that price is a mental trap?
Wed, 10 Apr 2024 - 1h 03min
1146 - 20VC: Postmates Founder Basti Lehmann on How the Uber Deal Went Down and How a $2.65BN Deal Turned into $5BN, Why Great VCs Add No Value and VC Value Add is BS Marketing & Why The Biggest Companies in History Will be Born Today and Replace Incumbents
Basti Lehmann is the co-founder and former CEO of Postmates, the on-demand delivery service that raised over $900M from the likes of Tiger Global, Founders Fund, Spark Capital and Andreesen Horowitz. Following Uber’s $2.65BN acquisition in 2020, Basti founded TipTop, a platform for fast tech sales which Marc Andreesen led the $20M seed round for.
In Today’s Episode with Basti Lehmann We Discuss:
How did Basti start his career hacking AT&T?
How did early hardships shape Basti’s work ethic?
What were Basti’s biggest challenges building Postmates?
How did Basti raise $20M from Marc Andreesen?
How does Basti select which VCs to work with?
Why does Basti think 99% of VCs are sheep?
Why does Basti think great VCs add no value?
Why does Basti think having to educate investors is a massive red flag?
Why did Basti sell Postmates to Uber? How did the acquisition happen?
Was there anything Basti would have done differently?
What does Basti think makes Dara Khosrowshahi a great CEO?
What is Basti’s biggest advice to founders on acquisitions?
What does Basti think is the biggest challenge of LLMs today?
Why does Basti think inference computing will be the future of AI?
Why does Basti think incumbents can be replaced?
Why does Basti think the biggest companies are being born today?
Mon, 08 Apr 2024 - 59min
1145 - 20VC: Oscar Health: How to Deal with a 94% Decline in Market Cap, "Why I Stood Aside as CEO" and The Rebound Journey to $5.8BN in Revenue with Mario Schlosser, Co-Founder @ Oscar Health
Mario Schlosser is the Co-Founder and Chief Technology Officer at Oscar Health. The public company that went public with a market cap of $7.1BN. Following a tumultuous time in the markets, their stock price dropped 94%. Today, the company has rebounded and has a market cap of $3.2BN with an astonishing $5.8BN of revenues. Before co-founding Oscar, Mario also co-founded the largest social gaming company in Latin America.
In Today's Episode with Mario Schlosser We Discuss:
1. From German Middle-Class to Public Company Founder:
How did Mario make his way into the world of tech and come to co-found Oscar with Josh Kushner? Does Mario agree with Jensen Huang that "we should all have lower expectations"? What does Mario know now that he wishes he had known when he started Oscar?
2. Why Did Oscar Tank 94% in the Public Markets:
What was the core reason why Oscar tanked 94% in the markets? What would Mario have done differently knowing all he knows now about public markets? Does Mario regret going public? What are the biggest pros and cons?
3. The Mental Challenge of a 94% Market Cap Decline:
How did Mario mentally deal with the company being down 94%? What does he say to himself in the truly hard times? How did Mario use his co-founder, a coach and his family, to get through the really bad times? What are Mario's experiences like with anti-depressants? What worked? What did not?
4. Firing Yourself as CEO:
Why did Mario decide to step aside as CEO? What was the decision-making process? On reflection, does Mario think he was a good CEO? Where was he good? Where was he bad? What are the biggest management pieces of advice that Mario thinks are BS?
Fri, 05 Apr 2024 - 1h 09min
1144 - 20VC: Founders Fund's Trae Stephens on Why The Most Competitive Deals are the Worst, Why No Company is Successful Because of their VC, Why We are Making ZIRP Mistakes Again Today, Why Loss Ratio is BS and Upside Maximisation is Everything
Trae Stephens is a Partner at Founders Fund, one of the world's leading funds where he has worked with some of the best and backed the likes of Palmer Luckey with Oculus and Ryan Peterson @ Flexport since the very early days. Trae is also Co-founder and Executive Chairman of Anduril Industries, a defense technology company focused on autonomous systems, and Co-founder of Sol, a next-generation wearable e-reader. Previously, Trae was an early employee at Palantir Technologies, where he was also an integral part of the product team, leading the design and strategy for new product offerings.
In Today's Episode with Trae Stephens We Discuss:
1. From Hustling into Georgetown to Peter Thiel Ushering You into VC:
What is Trae's story of how he got into Georgetown University, despite being rejected the first time? How did Trae make his way into the world of VC? How did Peter Thiel recruit him to Founders Fund? What advice did Brian Singerman give Trae in his first week in VC? Why is it so important?
2. How the Best Venture Firm in the World Invests:
Decision-Making Process: Why do Founders Fund not have partner meetings? What is the investment decision-making process? Why does more process lead to mediocre outcomes? Competitive Deals: Why does Trae believe the most competitive deals are always the worst? What do Founders Fund do to specifically avoid the "herd mentality"? Upside Maximisation: Why does no one at Founders Fund care about "downside protection"? How do the team approach scenario planning and upside maximisation?
3. Do VCs Really Add Value:
Why does Trae think putting VCs on a board for "value add" is total BS? Are there any cases in which Trae believes the VC can really move the needle for a company? Why does Trae believe venture would be better if it were just operator investors? Why does Trae believe platform approaches to VC value add is BS?
4. The Future of VC: Who and How to Win:
How did being an operator at the same time as investing, make Trae a better investor? Why does Trae believe that vertical investing is BS and generalised is better? How does Trae favour; market, product and people? Will Trae back a founder when he hates the idea? What have been Trae's biggest lessons from his biggest hits and biggest misses in 10 years?
Wed, 03 Apr 2024 - 1h 12min
1143 - 20VC: The Memo: The $23BN Company You Might Not Have Heard Of: Tradeweb, The Story of 27 Years of Compounding Growth Leading to the Market Leader with $1.4BN in Revenue and 50% EBITDA Margins
Billy Hult is Chief Executive Officer of Tradeweb Markets (Nasdaq: TW), as Billy puts it, they are the "electronic interface that connects Citadel and Goldman". They are also one of the most under the radar but incredible businesses of the last 20 years. Through no glitz acquisitions or specific moments, TradeWeb has compounded organic growth for the last 27 years to today, with a market cap of $22BN.
In Today's Episode with Billy Hult:
1. From Betting Shop Worker to Public Company CEO:
How would Billy's teachers and parents have described the young Billy? Why does Billy think it is so important to have a hard first job when growing up? What does Billy know now that he wishes he had known when he started?
2. What it Takes to be a World-Leading CEO:
How does Billy define the role of the CEO? What are the core tenets? What has been the single hardest element of CEOship to learn? Does Billy care about being liked? How does that impact his management style? Why does Billy think it is so important for CEOs to make "big bets"? What have been his biggest?
3. Hiring World-Class Teams in 2024:
What have been some of Billy's biggest hiring mistakes? What did he learn from them? How does Billy weigh IQ vs EQ and hustle? Which wins? Why? Does Billy think this generation of millennials is too soft? What are the single biggest lessons Billy has on when to delegate vs when to retain control?
4. Money, Power and Family:
How does Billy approach his relationship to money today? How has it changed over time? Fame, power or money, rank them from 1-3. How does Billy rank them? How does Billy describe his own style of parenting? How has it changed over time?
Fri, 29 Mar 2024 - 51min
1142 - 20VC: a16z's Chris Dixon on Who Will Win the Next Generation of Venture, The Two Ways to Make Great Venture Investments and Find the Best Entrepreneurs & Why AI Will Strengthen the Position of the Incumbents Moving Forward
Chris Dixon is a General Partner at Andreessen Horowitz, one of the leading venture firms of the last decade with investments in Oculus (acquired by Facebook), Coinbase, and many more. Chris also founded and leads a16z crypto, a division of the firm that he has grown from $300 million in 2018 to more than $7 billion of committed capital. Due to his many successes, Chris was named #1 on the Forbes Midas List in 2022.
In Today’s Episode with Chris Dixon We Discuss:
How did Chris make his way into the world of venture and startups? When did he realize investing was his calling? How did Chris Dixon come to co-found Founder Collective with Dave Frankel and Eric Paley?
What are Chris’ biggest lessons from working with Marc Andreesen and Ben Horowitz? Does Chris agree with Doug Leone, “venture has transitioned from a boutique high margin business to a low margin commoditised industry”? What are the two ways to win in venture? Does Chris agree the best founders don’t need their VCs? What is Chris’ biggest investing miss? How did it impact his mindset?
What is the biggest problem with open-source internet today? Does Chris think incumbents can be replaced? Why does Chris think AI will strengthen incumbents? Does Chris think OpenAI should be open-sourced?
What is the biggest misconception of crypto today? Does Chris think speculation is bad for crypto? What would Chris most like to change in the world of crypto? How does Chris think Trump will affect crypto?
Wed, 27 Mar 2024 - 55min
1141 - 20VC: Lessons from 32 Years of Fund Investing | Why Exits Will Be Larger & Funds Sizes Bigger | Top Reasons to Turn Down Potential Fund Investments | Fees, Carry, Deployment Pace; What Do LPs Inspect When Fund Investing with David Clark, CIO @ Vencap
David Clark is the CIO of Vencap, one of the leading fund of funds in the venture landscape. David has been at Vencap for 32 years and has been an LP his entire career.
In Today's Episode with David Clark We Discuss:
1. From Unemployed Student in Love to Leading LP:
How did a girlfriend lead to David taking his first steps into the world of fund investing? What does David know now about fund investing that he wishes he had known when he started?
2. Is Being an LP Harder than Ever Before:
Does David agree with Doug Leone, "venture has transitioned from a boutique high margin business to a low margin commoditised industry"? Does David agree with Ryan Akinna @ MIT, "it is harder than ever to be an LP"? Does David think that venture returns will worsen in the coming years? Has the denominator effect for LPs gone? Do LPs have liquidity today?
3. What Makes the Best Performing Funds:
What are the single biggest commonalities in managers that did a 3x net DPI fund? Of managers with a 3x net fund, how many had a single company return the fund? How do the best firms do generational transition? How do the best firms take cash off the table and sell part or all of their position?
4. Five Things LPs Hate In Potential VC Investments:
What are the two most common reasons David will turn down a manager? How does David feel about the varying fee and carry levels? How does David feel about the compression of deployment times of funds? How does David feel about managers increasing fund size so significantly on every cycle?
5. Fund Sizes, Exits and Concentrating Returns:
Why does David believe exit sizes will increase and fund sizes could be even larger? Why does David think that despite the above, the concentration of returns will be even smaller? Is David concerned by the IPO window being largely shut and the increased regulation on M&A?
Mon, 25 Mar 2024 - 1h 10min
1140 - 20VC: Bryan Johnson on Why Humans Are No Longer Qualified to Manage Our Own Affairs, How Algorithms Will Run our Bodies and How to Process New Ideas and Challenge Conventional Beliefs
Bryan Johnson is the founder of Blueprint, the man is at war with death and is mastering longevity. Bryan is on a mission aimed at enhancing human intelligence and being respected by people in the 25th century. Before starting Blueprint, Bryan also founded Braintree (acquired by PayPal for $800M) and OS Fund – a $100M venture capital fund investing in genomics, synthetic biology, and complex systems.
In Today’s Episode with Bryan Johnson We Discuss:
What does Bryan think is the biggest existential threat to humankind?
Why does Bryan believe humans are unfit to manage their own affairs?
Why does Bryan care about being liked by the 25th century?
Does Bryan think society is ready to adapt to immortality?
What 3 questions does Bryan ask to test new ideas?
How does Bryan combat against his own biases?
How does Bryan adapt to change? What has been his most painful experience?
Why does Bryan think religion is humanity’s most durable technology?
What did Bryan learn about himself as the most measured human in the world?
How does Bryan use algorithms to take care of himself?
What has been Bryan’s most expensive test?
How did Bryan use data to rejuvenate his sexual function?
How will tech & AI play a role in human longevity?
How does Bryan raise his children?
How does Bryan get perfect sleep every night? What are his tips?
What is Bryan’s advice to people who think it’s too late to start becoming healthy?
What health advice does Bryan think is BS?
Fri, 22 Mar 2024 - 52min
1139 - 20Product: Why Process is Killing Your Product Team and How to Remove it | Three Product Decisions Every Team Needs to Make | Why the Best Companies Build Movements and Lessons from Shopify and Atlassian on How to Do It Right with Jean-Michel Lemieux
Jean-Michel Lemieux is one of the OGs of engineering and product having been the CTO at Shopify and the VP Engineering at Atlassian. Jean-Michel helped grow both Shopify and Atlassian from single-product to multi-product companies and led the building of their platforms.
In Today’s Episode with Jean-Michel Lemieux We Discuss:
How did Jean-Michel make his way into the world of product?
What were Jean-Michel’s biggest lessons from his time at Atlassian & Shopify?
How are Shopify & Atlassian the same? How are they different?
Why does Jean-Michel think Shopify could have been 10x bigger?
How does Atlassian & Shopify build movements instead of product?
What does Jean-Michel know now that he wishes he had known before he joined Atlassian & Shopify?
How does Jean-Michel balance between shipping speed vs. quality?
Why does JM think scrums and TDDs are BS? How did his last year at Shopify change his approach in product development?
What is a time horizon friction? And how does it impact teams?
What is micro alignment, and why does Jean-Michel think it is so important?
What 3 types of decisions every team makes?
What does Jean-Michel think are the most common reasons teams become average? How does he prevent it?
What do Jean-Michel think are the most common mistakes CEOs make today?
How does Jean-Michel structure the interview process for new product hires?
What signals does Jean-Michel look out for when hiring? Why does he believe experience does not matter?
What are Jean-Michel’s biggest hiring mistakes? What were his lessons?
What are 2 of the most common mistakes founders make when hiring a product team?
Wed, 20 Mar 2024 - 1h 04min
1138 - 20VC: 19 Company Portfolio: 1 Decacorn, 7 Unicorns, 4 Acquisitions; One of the Best Seed Investors of All Time on How to Pick Generational Defining Founders, Why Nothing but the Founder Matters & Why the Best Investors are Never Happy w/ Gili Raanan
Gili Raanan is the Founder of Cyberstarts and one of the most successful seed investors ever. In his 19 company portfolio, Gili has invested in a decacorn (Wiz), seven unicorns and had three others acquired. Prior to Cyberstarts, Gili spent over 15 years as a General Partner @ Sequoia Capital investing in some of the world's best cyber security companies.
In Today's Episode with Gili Raanan We Discuss:
1. From Founder to World's Best Seed Investor:
How did Gili make the move into the world of venture with Sequoia? How did Mike Moritz and Doug Leone recruit him? What was that process like? What are 1-2 of Gili's biggest takeaways from working with Doug and Mike?
2. How to Find and Pick the Best Founders:
What did Mike Moritz teach Gili about getting to know founders? Why does Gili look for the pain in the eyes of the founder? What questions does he ask? What are the most common signals of truly exceptional founders, having backed 7 unicorns? Why does Gili believe that both market and product is BS? Why are the founders all that matters? Why does Gili believe that the founder does not have to be a domain expert in a market to create a massive company in that market?
3. What it Takes to be the Best Seed Investor:
Why does Gili believe that the best seed investors do not have theses? How important does Gili feel the brand of the VC firm is? What were his biggest lessons on brand from spending 15 years as a General Partner @ Sequoia? Why does Gili believe that the best investors are never happy? When you are happy, you lose.
4. 2021 is Back: Pricing, Uprounds and more
Why does Gili believe that the best companies are always expensive and will always be expensive at every round? Why does Gili believe that 2021 pricing and funding is back? Is this a good thing? How does Gili advise founders on how much to raise and what valuation to set with investors? What does Gili believe are the single biggest sins from the zero interest rate environment?
Mon, 18 Mar 2024 - 57min
1137 - 20VC: Bending Spoons: The Most Untold Success Story in Startups: Lessons Scaling to 500M Downloads, $360M in Reported 2023 Sales and a $2.55BN Valuation... Bootstrapped with Luca Ferrari, Co-Founder and CEO @ Bending Spoons
Luca Ferrari is Co-Founder and CEO of Bending Spoons, one of the most incredible but untold success stories in startups. Luca has scaled Bending Spoons to 100M monthly active users, $380M in sales in 2023 and aiming to reach $500M in EBITDA by the end of 2026. The company’s products include Evernote, Meetup, Remini, and Splice and their products have now been downloaded more than 500M times.
In Today’s Episode with Luca Ferrari We Discuss:
What was Luca like as a child? How would his parents have described him? Why did Luca share his McKinsey salary with his co-founders? What were Luca’s biggest lessons from his failed startup?
Why did Luca decide to bootstrap Bending Spoons? What does Luca think about the EU vs. US startup environment? Why did Luca kill a $7M project? What were his lessons? How did Luca pick his investors?
What are the 3 key traits Luca looks for when picking the best talent? Why does Luca think traditional interview strategies do not work? What tests does Luca conduct for each candidate? What were Luca’s biggest hiring mistakes?
How does Luca determine which products to acquire? How does he identify signals? How does Luca approach pricing assets? How does he win every bid? What are Luca’s biggest lessons from acquiring Evernote? What key lessons on risk management does Luca wish he’d known 10 years ago? What are Luca’s biggest challenges on user acquisition?
Fri, 15 Mar 2024 - 53min
1136 - 20Growth: Top Five Lessons from Leading Analytics at Facebook and Data Science at Sequoia Capital, The Two Skills Required to do Analytics Well, The Three Types of Execs within Companies and When and How to Hire for Growth with Chandra Narayanan
Chandra Narayanan is one of the growth and analytics OGs having spent 7 years at Facebook leading analytics for the Facebook App and for Instagram. After Facebook, Chandra became Chief Data Scientist @ Sequoia Capital, helping Sequoia, find, select and help the best entrepreneurs in the world. Today, Chandra is the Founder & CEO @ Sundial, building products to help builders make meaningful use of data to fulfill *their* mission.
In Today's Episode with Chandra Narayanan
1. From Working on the Weather to Leading Analytics at Facebook:
How did Chandra make his way from analyzing weather patterns to leading analytics for Facebook? What does Chandra know now that he wishes he had known when he started his career in growth? How did one piece of advice from his manager at Paypal change Chandra's mind forever on "quitting" and when to "quit"?
2. Growth and Analytics 101:
What does growth mean to Chandra? What is it? What is it not? When is the right time to hire a growth team/person? What is the right profile for the first growth hires?
3. How to Hire the Best Growth Teams in the World:
What are the must-ask questions when hiring for growth? How does Chandra use case studies to determine the quality of a candidate? What does Chandra believe are the four main reasons people go to work? What are the three different types of execs in tech? How do you know when you need each one?
4. Lessons from Leading Analytics at Facebook and Sequoia:
What are 1-2 of Chandra's biggest takeaways from leading analytics at Facebook? What does Chandra believe are the two core skills needed to do analytics well? How can you easily test if someone is good at analytics? How did being Chief Data Scientist @ Sequoia change Chandra's perspective on growth?
Wed, 13 Mar 2024 - 1h 15min
1135 - 20VC: The Future of TikTok; Is it a Danger to US National Security| Why the "Woke Mind Virus" is a "Post-Modern Religion" and Is it Too Late to Reverse | Why the Education System is Broken | Investing Lessons from Wish, Palantir and Lady Gaga | Joe Lonsda
Joe Lonsdale is the Founder and Managing Partner at 8VC, an early-stage venture capital firm managing over $6 billion in capital. In 2003, he founded Palantir Technologies. Since then, he has founded over a dozen companies, including Addepar, a wealth management platform helping investors manage over $5 trillion, and OpenGov, recently sold for $1.8BN.
In Today’s Episode with Joe Lonsdale We Discuss:
The Making of a Multi-Unicorn Founder:
What was Joe like as a child? How would his parents and teachers have described him? What does Joe know now that he wishes he had known when he started his career? How does Joe view the importance of luck and skill in success?
America’s New Dawn: Navigating Frontiers and Accountability
What did Joe mean by describing America as a “frontier nation”? How does Joe contrast America’s frontiers with Europe’s social safety nets? How does Joe propose restoring America using the “scalpel over the sledgehammer” approach? How can America introduce accountability to non-profit institutions? What role do for-profit prisons play?
Woke Mind Virus
Why does Joe consider the Woke Mind Virus a “Bad Postmodern Religion”? Why does Joe see Elon Musk as a key figure in challenging “woke minds”? Why does Joe believe the education system is a core problem? What needs to change? Is it too late to reverse the current state of “woke mind virus”?
TikTok, China, Israel:
What does Joe believe is the right solution for TikTok’s ownership? To what extent is TikTok a danger to American national security? What does Joe predict will happen to China from here? What needs to change? How does Joe predict the next 24 months for the conflict in Israel and Gaza?
Investing Lessons: Wish, Palantir and more
What are Joe’s biggest takeaways from the failing of Wish? What did Joe learn from the failed project with Lady Gaga? How does Joe reflect on when is the right time to sell? How does Joe reflect on his own relationship to money?
Mon, 11 Mar 2024 - 58min
1134 - 20Sales: Outbound Sales is Dead Today, Why Demand Generation Will Move Back Under Marketing, "Wisdom" that Everyone Needs to Unlearn About Sales & Why You Should Never Hire Someone You Do Not Know in Your First Five Hires with Brendon Cassidy
Brendon Cassidy is one of the OG of enterprise sales of the last decade, having advised the likes of Gong.io, Pipedrive, Showpad. Previously Brendon was first Head of Sales at LinkedIn and VP of Sales at Talkdesk.
In Today's Episode with Brendon Cassidy We Discuss:
1. From Recruiter to Sales OG and Linkedin's First Head of Sales:
How did recruiting prepare Brendon for a career in sales? What impact did the dot-com bubble burst have on his early career? What does Brendon know now that he wishes he had known when he started his career in sales?
2. The Sales Playbook and Hiring The Team:
How does Brendon define the "sales playbook"? Should the founder be the one to create and execute V1 of the playbook? Should the first sales hire be a rep or a sales leader? When is the right time to make that all-important first sales hire?
3. Why Discovery and Outbound Are Broken Today:
Why does Brendon feel discovery is useless in today’s sales process? Why does Brendon believe outbound will move under the marketing function? How does AI change the world of outbound sales? Why will no great sales leaders join a company that doesn’t have an inbound machine?
4. How to Master Onboarding and Increase Sales Performance:
What is the right way to onboard new sales reps? How quickly do you know if a sales rep is not good? What are the signs? What is the right way to measure the effectiveness of sales teams today? What are the biggest mistakes founders make in onboarding sales teams?
Fri, 08 Mar 2024 - 42min
1133 - 20VC: 27 Years of Investing Lessons on Picking Founders, Price Discipline, Reserves and Selling Positions | Can Seed Investors Compete with Multi-Stage Venture Firms | Why Returns Will Not Worsen Moving Forward with Peter Wagner, Founder @ Wing
Peter Wagner is a Founding Partner of Wing. Peter has led investments in dozens of early-stage companies including Snowflake, Gong, Pinecone, and many others which have gone on to complete IPO's or successful acquisitions. Prior to founding Wing, Peter spent an incredible 14 years at Accel, starting as an associate in 1996 and scaling to Managing Partner, before leaving to start Wing.
In Today's Episode with Peter Wagner We Discuss:
1. From Associate to Managing Partner to Founding Partner:
How did Peter first make his way into the world of venture as an associate at Accel? How important does Peter believe it is to have early hits in your career as an investor? What is the biggest mistake Peter sees young VCs make today?
2. The Venture Market: What Happens Now:
Does Peter agree with Roger Ehrenberg that venture returns will worsen moving forward? How does Peter answer the question of how large asset management venture firms co-exist in a world of boutique seed players also? Does Peter agree with Doug Leone that "venture has transitioned from a high-margin boutique business to a low-margin, commoditized industry?
3. Investing Lessons from 27 Years and Countless IPOs:
What have been some of Peter's single biggest investing lessons from 27 years in venture? Why is Peter so skeptical of capital-intensive businesses? Will defense and climate startups suffer the same fate as clean tech did in the 2000s? How does Peter reflect on his own relationship to price? When does it matter? When does it not? What have been Peter's biggest lessons on when to sell positions vs when to hold? What has been Peter's biggest miss? How did it impact his mindset?
4. Building a Firm from Nothing:
How was the fundraise process when leaving the Accel machine and raising with Wing? What have been the single hardest elements of building Wing? What did he not expect? What advice does Peter have for someone wanting to start their firm today?
Wed, 06 Mar 2024 - 55min
1132 - 20VC: Managing the Largest Sovereign Wealth Fund in the World: $1.55 Trn of Assets & Owning 1.5% of all Listed Companies with Nicolai Tangen, CEO @ Norges Bank Investment Management
Nicolai Tangen is the CEO of Norges Bank Investment Management, the largest sovereign wealth fund in the world with $1.55 Trn in assets, owning on average, 1.5% of every listed company. Tangen was previously Chief Executive Officer and Chief Investment Officer in AKO Capital, which he founded in 2005. Prior to this, Tangen was a partner and senior analyst at Egerton Capital and an equity analyst at Cazenove & Co.
In Today's Episode with Nicolai Tangen We Discuss:
From Religious Town in Norway to Leading the Largest Sovereign Wealth Fund:
What was Nicolai like as a child? How would his parents have described him? Why does Nicolai think that loners have a greater chance/ability to make money? What does Nicolai know now that he wishes he could tell a 20-year-old Nicolai?
The Top 10 Questions:
1. US Tech Firm Concentration: Is Nicolai concerned by the concentration of enterprise value in US tech firms? Have incumbents ever been as strong as they are today?
2. Impact of AI: What does Nicolai believe the impact of AI will be on society and productivity? What is his approach to investing in it moving forward?
3. Bitcoin: Why does Nicolai not want to hold Bitcoin? Why does he not understand it?
4. China: What would need to happen for China to be investable? How will the China situation play out?
5. Europe: Does Nicolai believe Europe is so far behind the US? Why? What can we do to improve?
6. Climate Change: How does Nicolai approach investing in climate? What works? What does not?
7. Sam Altman: Would Nicolai invest in Sam's new $7Trn project? What are some of Nicolai's biggest lessons from the time he has spent with Sam?
8. Investment Psychology: How does Nicolai retain a neutral investor psychology? How does he not get too up when doing well and too low when not doing well?
9. Investing Lessons: What are Nicolai's biggest investment hits and misses? What did he learn from them?
10. The Future: Why is Nicolai so optimistic about the future? What is he concerned about? How will we overcome our greatest challenges?
Mon, 04 Mar 2024 - 45min
1131 - 20VC: Are IPO Windows Shut? Has Regulation Killed the M&A Market? M&A OG Frank Quattrone on Lessons from 650 M&A Deals Worth Over $1TRN and Taking Amazon, Cisco and Netscape Public
Frank Quattrone is the Founder and Executive Chairman of Qatalyst and served as its CEO from the Firm’s founding until January 2016. Over more than four decades, Frank and the teams he has led have advised on more than 600 mergers and acquisitions with an aggregate transaction value over $1 trillion and on more than 350 financings that raised over $65 billion for technology companies worldwide. Frank led the IPOs of Amazon.com, Cisco, Intuit, Netscape, among many others. He advised Apple on its $400 MM acquisition of NeXT (which led to Steve Jobs’ return to Apple); Concur on its $8.3B sale to SAP; LinkedIn on its $28.1B sale to Microsoft; Qualtrics on its $8B sale to SAP and Twitch on its $1B sale to Amazon.com.
In Today's Episode with Frank Quattrone:
1. Has Regulation Killed M&A:
Why does Frank disagree that regulation has killed M&A? What is the real reason why M&A is so down at present? What would impact would a Trump administration have on the M&A environment? What are some of Frank's biggest lessons from 600 prior transactions over dour decades of what happens when an M&A market shuts down?
2. When Will the IPO Window Re-Open:
Does Frank agree that the IPO window is currently closed for tech companies? How does this IPO window compare to the dot com bust and 2007? What is needed for the IPO window to re-open? What is the timeline that Frank puts on the IPO window opening again?
3. M&A: How Do Companies Get Bought:
What is the process for a company to be bought? What are the single biggest mistakes the seller makes in the process? What do the best buyers and sellers do to get the best price? Does Frank agree with the notion that "companies are bought and not sold"?
4. IPOing Amazing, Selling Linkedin and Qualtrics:
What is the story behind, Frank, Bill Gurley, Jeff Bezos and John Doerr pricing the Amazon IPO? How did Linkedin come to be bought by Microsoft? What did that process look like? How did Frank structure an event to ensure that Ryan @ Qualtrics and Bill McDermot @ SAP would meet and lead to the acquisiiton?
Fri, 01 Mar 2024 - 58min
1130 - 20VC: Startups Only Fail When Founders Stop Trying, Why the Two Weeks Following Our IPO Were the Worst of my Life & Why Tieing Your Identity to Your Company is the Most Dangerous Thing and How to Avoid It with Sami Inkinen, Co-Founder & CEO @ Virta Health
Sami Inkinen is the Co-Founder and CEO of Virta Health, the company reversing type 2 diabetes. Before Virta, Sami was the Co-Founder of Trulia, steering the company to a successful IPO and its eventual sale to Zillow Group. Outside of the boardroom, he launched Fat Chance Row, a daring venture to row 2,750 miles across the Pacific, unsupported with his wife, rowing 18 hours straight per day.
In Today's Episode with Sami Inkinen:
1. From Farm in Finland to IPO Founder: Relationship to Money
How did Sami's humble upbringing on a farm in Finland impact his early mindset and ambition? How does Sami analyze his relationship to money today? How has it changed over time? Why was the two weeks following Trulia's IPO the worst two weeks of his life?
2. The Secret to Marriage: Rowing 2,750 Miles Together:
What are some of the biggest lessons on marriage Sami has from spending 45 days rowing the Pacific with only his wife for company? What was their single biggest argument over the 45 days? What did Sami learn from it? Sami worked with his wife, what are the biggest pros and cons of working with your spouse? Would Sami recommend it? What does Sami believe are the core fundamentals that underpin the best marriages?
3. The Secret to Parenting: The Regret of Delegation:
What is Sami's biggest regret when it comes to parenting? How does Sami think about what it means to be a great father today? How has that changed? How did Sami's relationship with his wife change when they had kids?
4. Relationship to Identity:
Why does Sami believe tieing your identity to the company, as a founder, is so dangerous? How does Sami advise on creating multiple personas to prevent this? Why does Sami believe that all the best founders are addicts to some extent?
Wed, 28 Feb 2024 - 1h 01min
1129 - 20VC: What it Takes to be Top 1% in Private Equity | Why the Best Companies are Talent Systems | Three Traits Required to Succeed in Private Equity | Marriage, Fatherhood and Sports Team Owner, What it Takes to Do It All, with Justin Ishbia, Founder @ Sho
Justin is the Founder and Managing Partner of one of the nation’s best-performing private equity firms, Shore Capital Partners (“Shore”). Since the firm’s inception in 2009, Shore has grown from 4 to over 140 team members managing over $6 billion in AUM, representing 900+ acquired companies and more than 33,000 employees. Shore is also one of the most active private equity firm in the world by deal volume according to PitchBook while continuing to achieve return profiles that rank Shore among the top 1% of private equity firms. Justin is an avid sports fan/investor and is the Alternate Governor for the Phoenix Suns (NBA), Phoenix Mercury (WNBA) and Nashville SC (MLS).
In Today's Episode with Justin Ishbia:
1. From Law Student to Founding Shore Capital:
How did seeing Justin's father operate impact how he thinks about building Shore today? What does he know now that he wishes he had known when he started Shore? How important a role does luck play in success? How has his mindset changed on this?
2. How to Make Top 1% PE Returns:
Why does Justin see private equity done well like "using a flashlight in a dark room"? What are the top 3 elements that Justin looks for in all acquisitions they make at Shore? When did Justin think there was an advantage of scale/network effect but was proved wrong? How does Justin think about downside protection and risk mitigation? Why does Justin like to back and invest in first time founders more than any other type?
3. Building World-Class Investing Teams:
Why does Justin believe the best companies are talent systems? How does Justin structure the talent system at Shore to ensure consistent incredible talent? What does Justin believe are the three traits required to win in private equity? What question does Justin ask all potential CEOs he hires for acquired companies? What has Justin learned is the single clearest sign of the top .1% talent?
4. Justin Ishbia: The Family Man and Husband:
What metric does Justin use to track whether he is being a good and present father? Is it possible to be top 1% and have balance with a wife and family? What does "great fatherhood" mean to Justin? How has his thoughts on this changed? How does Justin think about bringing kids up in a world of immense privilege and ensuring they remain ground and ambitious?
Mon, 26 Feb 2024 - 1h 21min
1128 - 20Product: The Five Step Process to Hiring the Best Product People, The Four Core Skills the Best PMs Need to Have, The Two Product Documents that Drive World Class Product Teams & Why the Best PMs are Writers with Scott Williamson, Former CPO @ Gitlab
Scott Williamson was most recently Chief Product Officer for GitLab, where he led a team of 65 in Product Management, Product Operations, Growth, Pricing, and Corporate Development functions. Before GitLab, Scott was VP of Product for SendGrid for over six years, where helped lead the company to a successful IPO and $3B acquisition by Twilio.
In Today's Episode with Scott Williamson We Discuss:
1. From Sales to Product Leader:
Why does Scott believe sales is a great starting point for product people? To what extent does an MBA help someone wanting to pursue a career in product management? What does Scott know now that he wishes he had known when he started his career in product?
2. What, Who, When: How to Build a Product Team:
Is product management art or science? What is the ratio? What are the four core roles of a product manager today? When is the right time to hire your first PM? What is the ideal profile for this first PM hire? What are the single biggest mistakes founders make when hiring PMs?
3. Hiring the Best Product People:
What does Scott's hiring process look like for all new product hires? How does Scott test for systematic thinking and problem-solving ability? What questions does Scott always ask in interviews? What are the best case studies to use to test a candidate's skill set? How important is it for the candidate to have domain expertise in your product category?
4. The Best Product Teams are the Best Writers:
What are the two different types of documents that product teams must use? How do you know when to use a one-pager vs a six-pager? How does the discussion and planning cycle for the different documents differ? How important is it for PMs to be great writers also?
Wed, 21 Feb 2024 - 55min
1127 - 20VC: Why VC Returns Will Get Worse, Why LP Incentive Structures are so Broken, What is the Answer to Liquidity with No M&A or IPOs, When to Sell vs Hold Your Winners & Turning $5M into $250M with The Trade Desk | Roger Ehrenberg, Eberg Capital
Roger Ehrenberg is a legend of the venture industry as the Founder of IA Ventures, among the most successful seed-stage venture firms of this generation, having seeded companies including Datadog (NASDAQ: DDOG), Digital Ocean (NYSE: DOCN), The Trade Desk (NASDAQ: TTD) and Wise (LSE: WISE.L). Today Roger is the Founder and Managing Partner of Eberg Capital, a pioneer in bridging the gap among sports franchises, sports betting, media and entertainment. Roger’s current sports investments include stakes in the Miami Marlins, Real Salt Lake, Alpine Racing, Betr, Commonwealth, Kero Sports, Simplebet, SlamBall, Smarkets and WagerWire.
In Today's Episode with Roger Ehrenberg We Discuss:
1. The Commoditisation of Venture and Worsening Returns:
Why does Roger disagree with Doug Leone that "we have moved from a boutique high margin business to a commoditised low margin industry"? Why does Roger believe we will see consistently worsening returns in venture? Is this influx of LP capital cyclical or is it here to stay?
2. The New LPs and The Broken Existing LP World:
Why does Roger think the existing incentive structure for LPs is totally broken? Who are the most important new LPs entering the venture market? How do sovereigns and pension funds entering venture change the industry? Which players have capitalised on this new LP class best?
3. Where Does the Liquidity Come From:
With the closed IPO window and lack of M&A, where will liquidity come from in the next 24 months? Would a Trump administration open M&A markets? Does Roger agree M&A markets are shut down? When does Roger believe IPO markets will open again? Will Databricks and Stripe go out in 2024? If Roger were to run a continuity fund strategy, how would he structure it? What would he do?
4. When to Sell and When to Hold:
How does Roger advise managers on when to sell vs when to hold? How important is it for a new firm to have a company go public in the first five years? What are Roger's biggest lessons from selling The Trade Desk at a $2.5BN valuation? How does Roger think about managers thinking they should manage the public book of their portfolio for their LPs? What are the pros and cons?
5. Relationship to Money:
Do rich investors make better investors? How does investing when you have a lot of cash already change your mindset around investing and exiting? How does Roger analyse his relationship to money today? What have been the single biggest needle movers in his wealth journey? How did it feel when he made a $6M bonus?
6. The Secrets to Parenthood and Marriage:
What does it mean to be a great father for Roger? How does Roger think about bringing his children up with the same level of hunger and ambition, despite being brought up with such wealth? What are Roger's two biggest lessons on the secret to a great marriage?
Mon, 19 Feb 2024 - 1h 11min
1126 - 20VC: From Selling 75% of Trade Republic for €600K to Raising $1.3BN at a $5.3BN Valuation, The Biggest Fundraising Lessons Having Raised $1.3BN From the Best in the World; Trade Republic CEO, Christian Hecker and Creandum General Partner Johan Brenner
Christian Hecker is the Founder and CEO of Trade Republic, the company making it easy and inexpensive for everyone with a smartphone to invest. To date, Christian has raised over $1.3BN for the company from the likes of Sequoia, Founders Fund, Accel and Creandum to name a few. Previously, Christian worked in Bank of America Merrill Lynch’s Investment Banking department.
Johan Brenner is a General Partner at Creandum. Johan has led Creandum’s investments in iZettle (acquired by PayPal for $2.2bn in 2018), Trade Republic, Klarna, Pleo, Neo4J, Vivino and more. Johan was previously a repeat entrepreneur, founding one of the first online brokers in Europe in 1997 (sold to E*TRADE in the US), then JobLine (sold to Monster), Bookatable (Michelin) and Tradera (Ebay).
In Today's Episode with Christian Hecker and Johan Brenner We Discuss:
1. Selling 75% of Trade Republic for €600,000:
How did Christian come to sell 75% of Trade Republic for €600K? How did Johan and Creandum solve this challenge when they invested? What are some of Christian's biggest pieces of advice on cap table construction?
2. Raising $1.3BN From the Best Investors in the World:
What are Christian's biggest fundraising lessons from raising $1.3BN from the best in the world? How did Doug Leone and Sequoia come to lead Trade Republic's round? What was the meeting with Doug like? What questions did he ask? How did it go? How important of a skill does Johan believe being a great fundraiser is for founders?
3. Scaling into Europe's Next Decacorn:
What are the single biggest issues that arise when scaling so fast? What breaks first? Does CAC increase with time or decrease? Why did Christian decide to stop paid marketing on Google and Facebook and stop spending $100M+ there overnight? Why is Christian so bullish on influencer marketing? What works? What does not work?
4. Europe: A Hub for Innovation or a Retirement Home:
Does Christian believe that young people in Europe work hard enough? What are the biggest challenges to scaling teams in Europe? Why does Johan believe the biggest challenge in Europe is the lack of exit markets? What can Europe do to improve and increase our chances of being successful?
Fri, 16 Feb 2024 - 56min
1125 - 20Growth: How to Master Product-Led-Growth, The Biggest Mistakes Startups Make When Scaling into Enterprise, How to Assess "Bets" in Growth; Which to Take and Which to Not with Gonto, Interim CMO @ Vercel
Martin Gontovnikas, a.k.a Gonto, is a software engineer at heart who moved to the “dark side” to focus on Marketing. With this career transition, he found a way to combine his 2 passions by applying his “engineering thinking” model to Marketing. He is now a B2B SaaS Advisor to Vercel and Airbyte among others and Co-Founder & GP of Hypergrowth Partners. Previously, he was SVP of Marketing and Growth at Auth0.
In Today's Episode with Martin Gontovnikas (Gonto) We Discuss:
1. From No Idea to Growth Leader:
How Gonto made his way into the world of growth when it was not a thing? What does Gonto know now that he wishes he had known when he entered the world of growth? Why does Gonto believe product and marketing is more important than sales and marketing?
2. Growth: What, When and Who:
What is growth? What is it not? What do people misunderstand most with growth? When is the right time to hire your first growth person? What is the right profile for the right first growth hire? Junior? Senior?
3. Mastering PLG and Enterprise:
What are the single biggest mistakes startups make when scaling into enterprise? Why does Gonto believe that all PLG companies should start with 6-8 design partners? Is it possible to do enterprise and PLG at the same time? How does one provide enough value in a PLG motion to convert enterprise buyers?
4. Data vs Intuition: Art vs Science:
Is growth more art or science? Why does Gonto believe qualitative data is more important than quantitative? How does Gonto think about psychology when selling and marketing? What do so few startups? understand about the psychology of their customers? How does Gonto approach messaging and what is truly great product marketing?
Wed, 14 Feb 2024 - 1h 10min
1124 - 20VC: The Ultimate Guide to Scaling Marketplaces, Why Rule of 40 and EBITDA Optimisation is BS, How Founders & VCs Should Approach Market Sizing and Outcome Scenario Planning and Why Europe is Failing with Vinted CEO, Thomas Plantenga & Alex Taussig
Thomas Plantenga is the CEO @ Vinted, one of the fastest-growing marketplaces in the world with a valuation of $4.5BN. Prior to becoming CEO, Thomas worked with a range of organisations including Bookaboat, OLX, Sellit/Wallapop and FJLabs.
Alex Taussig is a General Partner @ Lightspeed and co-leads the fund's Consumer investment team. Alex's portfolio includes the likes of All Day Kitchens, Archive Resale, Daily Harvest, Faire, Found, Frubana, Keychain, Kikoff, Vinted, YaySay, and Zola.
In Today's Episode with Thomas Plantenga and Alex Taussig We Discuss:
1. The CEO Who Did Not Want to be CEO:
How did Thomas come to be CEO @ Vinted? Why did he not want the job at first? What does Thomas know now that he wishes he had known when he started?
2. The Mechanics of the Fastest Growing Marketplace:
What is the single most important metric for Vinted? How does Vinted determine what market to open next? What do they look for? How does Vinted think about depth vs breadth in each country? What is the AOV today? How does it vary by country? How long does it take for each country to be cash flow positive?
3. The Biggest BS in Startups: Rule of 40 and EBITDA:
Why does Thomas think VC's obsession with "Rule of 40" is BS? Why does Thomas believe EBITDA optimization is BS and useless? What are the hardest elements of scaling a marketplace that no one knows?
4. The Bull, Bear and Investor Approach to Vinted:
Alex, what was Lightspeed's pre and post-mortem when investing in Vinted? How does Lightspeed analyze TAM and market sizing when investing? What was Lightspeed's single biggest concern when investing in Vinted?
5. Europe: A Hub of Innovation or a Retirement Home:
Does Thomas believe that European young people have a worse work ethic than those in the US? Is Thomas concerned by the state of regulation hampering innovation in Europe? What can be done to improve work ethic and the state of regulation today? Why is Alex and Lightspeed more bullish than ever on Europe today?
Mon, 12 Feb 2024 - 1h 13min
1123 - 20VC: Doug Leone, Bill Ackman, Bill Gurley and Orlando Bravo on "Does Price Matter"; When to Pay Up vs When to Stay Disciplined, The Biggest Lessons on Price Discipline from 8 of the World's Best Investors
Doug Leone is the Global Managing Partner @ Sequoia Capital, one of the world’s most renowned and successful venture firms with a portfolio including the likes of Google, Airbnb, Whatsapp, Stripe, Zoom and many more.
Marcelo Claure is the Founder & CEO of Claure Group, a multi-billion-dollar global investment firm. He is the Executive Chairman and Managing Partner of Bicycle Capital, a $500M Latin America-focused growth equity fund, and was appointed Chairman in Latin America of SHEIN, the global #1 on-demand fashion company in the world. Claure was also the CEO of SoftBank Group International where he launched SoftBank’s $8B Latin America Funds, and had direct oversight for SoftBank’s operating companies.
Geoff Lewis is a Founder and Managing Partner of Bedrock, one of the breakout and new venture firms of the last decade, famously in search of narrative violations. He serves or has served on the Board of Directors for companies including Lyft (NASDAQ: LYFT), Nubank (NYSE: NU), Epirus, and Vercel.
Bill Ackman is the CEO of Pershing Square Capital Management, L.P., an SEC-registered investment adviser founded in 2003. Pershing Square is a concentrated research-intensive fundamental value investor in long and occasionally short investments in the public markets.
Martín Escobari is Co-President, Managing Director and Head of General Atlantic’s business in Latin America. Martín is Chairman of the firm’s Investment Committee and also serves on the Management and Portfolio Committees.
Orlando Bravo is a Founder and Managing Partner of Thoma Bravo. He led Thoma Bravo’s early entry into software buyouts and built the firm into one of the top private equity firms in the world.
In Today's Episode on Price Sensitivity We Discuss:
Fri, 09 Feb 2024 - 28min
1122 - 20VC: The Chess.com Memo: The Most Untold Story in Startups; Scaling to $100M Revenue, 150M Members and 700 People, All with Zero Venture Funding | Erik Allebest, CEO @ Chess.com
Erik Allebest is the CEO @ Chess.com, the #1 online chess service on the planet with more than 150+ million members and 15+ million games played each day. Erik has scaled the company to over 700 people and $100M+ in revenue with no venture funding.
In Today's Episode with Erik Allebest:
1. From Unemployable to $100M+ Revenue Founder:
How did Erik make his way into the world of tech and startups? Was his MBA worth it? How does he advise others on whether to get one or not? What does Erik know now that he wishes he had known when he started?
2. Scaling to $100M Revenue with No Venture Funding:
Why did no one want to invest in Chess.com in the early days? What did Erik do differently as a result of not raising any venture funding? What would Erik have done if he had money from the start? What are Erik's biggest pieces of advice to founders with funding today?
3. Hard Lessons Scaling to 150M Members:
What are 1-2 of Erik's biggest lessons on how to scale users with zero budget? What customer acquisition worked? What did not work? How important was COVID and The Queen's Gambit to memberships and sign-ups? What are the single biggest mistakes Erik sees founders make on customer acquisition today?
4. Parenting, Marriage, Metrics and Money:
Why does Erik not care about money or capitalism today? How has Erik's style of parenting changed over the years? What works? What does not? What does Erik believe is the secret to marriage? What have been his biggest lessons? Why does Erik hate metrics? If so, how does he run the business towards goals and output?
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Wed, 07 Feb 2024 - 1h 11min
1121 - 20VC: The Biggest Misconceptions & Hardest Truths About Seed Investing Today; Why The Best Founders Don't Need You, Why Uncapped SAFEs Are Good, Why Reserves Are Bad, Why Signalling is BS, Why Price Doesn't Matter with David Tisch & Terrence Rohan
David Tisch is the Managing Partner of BoxGroup, one of the leading seed-stage investment firms of the last decade having invested in over 500 seed-stage startups, including Plaid, Ro, Ramp, PillPack, Amplitude, Stripe, Warby Parker, Harry’s, Flexport, Classpass, Airtable and more.
Terrence Rohan is the Managing Director @ Otherwise Fund, a fund that discretely empowers a network of today's top founders to make multi-stage venture investments. Terrence has invested in the likes of Figma, Hugging Face, Vanta, Notion and Robinhood to name a few.
In Today's Seed Investing Special We Discuss:
1. Is Seed Investing Now a Commoditised Asset Class:
Why does Dave Tisch believe seed investing will remain the most inefficient market? What does that mean for the future of returns at seed? Why should you always pay up and be price-insensitive at seed rounds? Why does David believe that no one is great at seed investing? Why does David believe that you cannot index the seed market?
2. The Biggest BS Elements of Venture Capital:
Signaling: Why does David believe that the theory of signaling is total BS? Why does Terrence disagree and think it is valid and common? Group Decision-Making: Why does Terrence believe that investing decisions should be made solo and groups merely encourage consensus decision-making? Reserves: Why does Terrence believe reserves hurt DPI and are not good? How does David respond given his growth fund? Venture Value Add: Why do David and Terrence think venture value add services platforms are BS and not worth it?
3. The World of LPs:
What is the single biggest misalignment between VCs and LPs? What are David and Terrence's biggest pieces of advice for emerging managers today? Should LPs expect depressed returns from venture as the asset class commoditises?
Mon, 05 Feb 2024 - 1h 29min
1120 - 20Product: Top Five Product Lessons from Creating Snapchat "Discover" and "Chat", How to Hire the Best Product Talent and Why Case Studies in Interviews are not Helpful & How AI Impacts the Future of Product Design with Will Wu, CTO @ Match Group
Will Wu is the CTO @ Match Group, the owner and operator of the largest global portfolio of popular online dating services including Tinder, Match.com, OkCupid, and Hinge to name a few. Prior to Match, Will was VP of Product at Snap Inc. As the 35th employee, Will spearheaded the creation of Snapchat’s “Discover” content platform. He also led the creation and growth of the “Chat” messaging feature, which today is a primary Snapchat engagement driver that connects hundreds of millions of people each day.
In Today's Episode with Will Wu We Discuss:
1. The Journey to Snap CPO:
How did Evan make his way into the world of product and come to meet Evan Spiegel? What are 1-2 of his biggest takeaways from his time at Snap? What does Will know now that he wishes he had known when he started in product?
2. How to Hire Product Teams:
How does Will structure the interview process for new product hires? What are the most telling questions of a candidate's product skills in hiring? What case studies and tests does Will do to assess a candidate? What are 1-2 of Will's biggest hiring mistakes in product?
3. How to Do Product Reviews Effectively:
What are Will's biggest lessons on what it takes to do product reviews well? What are the biggest mistakes product leaders make in product reviews? How can teams drive focus in product reviews? What works? What does not?
4. Product: Art or Science?
How does Will balance between gut/intuition and data in product decisions? Is simple always better in product design? What is human-centered design? How does it impact how Will approaches product?
Fri, 02 Feb 2024 - 54min
1119 - 20VC: The Metrics That Matter in SaaS Today; Why CaC Payback is Flawed & CAC Ratio is Better, Why You Need to Hire Three Sales Reps at a Time, How to Forecast in 2024 & Biggest Mistakes Made Forecasting & How to Make Customer Success Sell More with Dave K
Dave Kellogg is one of the OGs of Saas. Among his many accomplishments, Dave was the CMO of Business Objects where he helped scale the business from $30M to $1BN in revenue. Dave has also been a CEO twice, once scaling the business from $0 to $80M and the other business from $8M to $50M before selling it. Dave is also an advisor to some of the best including GainSight, Logickull, MongoDB, Pigment, Recorded Future, and Tableau.
In Today's Episode with Dave Kellogg We Discuss:
1. What are the Metrics That Matter:
Why is CAC payback period such a flawed metric? What is CAC ratio? Why is it more effective than understanding payback? Why is gross revenue retention more important than net revenue retention? What are the single biggest mistakes that founders make when using metrics today?
2. How to Build and Scale the Best Sales Teams:
Why should founders hire three sales reps at one time? What is the benefit? What are the three different types of sales calls all teams must have? What should all CEOs and Heads of Sales ask of their sales team in forecasting? What is the single biggest mistake most companies make in forecasting? How should a CEO/board member respond to a sales team that lets a deal slip to next quarter?
3. Are CFOs Buying New Tech and How to Win Renewals:
Are CFOs open for business? How has the top down sales process changed in the last year? Why is the way that startups think about renewals completely broken? What are the three different types of customer success teams we have today? What is the core role of customer success? How can we incentivise them to sell more?
4. Mastering Product Marketing, Customer Profiles and Crossing the Chasm:
How can we use product marketing to increase sales velocity? What is the single biggest risk in product marketing today? What does Dave mean when he says "an ICP starts as an aspiration and becomes a regression?"
Wed, 31 Jan 2024 - 1h 10min
1118 - 20VC: How MIT Selects Venture Managers to Invest in | The Three Categories of Check MIT Writes Into Funds | How MIT Builds Their Venture Fund Portfolio | How MIT Approach Direct Investing | Why Being an LP Has Never Been Harder with Ryan Akkina @ MIT
Ryan Akkina is a member of the Global Investment Team at the MIT Investment Management Company (MITIMCo), which is responsible for managing MIT's endowment and pension plans. Ryan has invested in the likes of Sequoia, Kleiner Perkins, a16z, Greenoaks and Initialized to name a few. Ryan also leads many of MITIMCo's direct co-investments including most notably into Coupang and Rippling. Prior to joining MITIMCo, Ryan was a consultant at McKinsey & Company.
In Today's Episode with Ryan Akkina We Discuss:
1. From Engineer to LP with MIT:
How did Ryan make his way into the world of fund investing as an LP with MIT? Why did he turn down the chance to be a VC early in his career? What does Ryan know now that he wishes he had known when he started at MIT?
2. The Manager Evaluation Process for MIT:
What does Ryan look for most when investing in new managers? How important is track record when evaluating a new manager? What is the biggest mistake Ryan has made in picking a manager? What did he not see that he wish he had seen? How did that change his process?
3. How MIT Builds Their Portfolio:
How does MIT construct their portfolio from private to public to everything in between? What are the three different types of check sizes that MIT writes when investing in new managers? What are the most common reasons why MIT will not re-up with a manager? What are the single biggest reasons why great managers turn bad?
4. MIT: The Direct Investor:
Why does MIT see so much opportunity in direct investing? How does MIT approach the direct investing process? How do they approach underwriting themselves vs working with their managers in the process? How do MIT think about the right number of direct deals to make up their portfolio? How do they approach check sizing on a per-company direct investment? What has been Ryan's biggest direct investing mistake? How did that change his approach and mindset?
5. LP Markets Today and Where We Go From Here:
Are LPs open for business today? What type of firms will not struggle? Which will? How does Ryan view liquidity windows today? When will M&A and IPO markets open? What would Ryan most like to change about the world of LPs? Why does Ryan believe the LP incentive structure in terms of compensation is broken?
Mon, 29 Jan 2024 - 57min
1117 - 20VC: Are the SEC Overreaching with its Approach to Crypto? Should Gensler Step Down? How do US Elections Impact Crypto Markets? How Did SBF and FTX Impact Crypto Long Term and more with Dave Ripley, CEO @ Kraken
Dave Ripley is the CEO @ Kraken, one of the world's largest cryptocurrency exchanges, valued in 2022 at a whopping $10.8BN. Prior to Kraken, Dave was the Co-Founder of Glidera, a market-leading Blockchain technology company that Kraken acquired in 2016.
In Today's Episode with Dave Ripley:
1. From Boston Consulting Group to CEO of Kraken:
How did Dave first make his way into the world of crypto? What are the single hardest elements of a CEO transition? What does Dave know now that he wishes he had known about CEOship?
2. What is the Usage for Crypto:
Other than as a store of value, what application usage does crypto serve? Global payments are fine as is and are improving, why do they need crypto? Global remittance is served by Remote and Deel, why do they need crypto? No applications have been provided well, what really is the use case that makes sense?
3. Should Gensler Be Let Go and The SEC is Wrong:
Why is the approach of the SEC completely flawed? Should Gensler be fired for his ineffectiveness? What is the right policy stance and approach to take from here?
Fri, 26 Jan 2024 - 30min
1116 - 20Sales: How to Scale Into Enterprise Effectively and the Biggest Mistakes Made When Making the Move From PLG to Enterprise, Why Discovery Today is F***** & The Biggest Lessons on How to Do Sales Team Compensation with Sean Murray, CRO @ Greenhouse
Sean Murray is the CRO @ Greenhouse which is the fourth company Sean has scaled successfully into the enterprise. Sean's prior roles include revenue leadership positions at Saleloft (CRO), Xactly (VP Sales), and CEB, now Gartner (Head of MID Global Sales).
In Today's Episode with Sean Murray
1. The Origin Story: Is a Love of Sales Born:
How did Sean first fall in love with Sales? What does Sean know now that he wishes he had known when he started his career in sales? What is Sean's biggest advice to a young person entering the sales world today?
2. Sales has Changed; You Need to Change with It:
Why do CMOs need to be good sellers and CROs need to be good marketers today? Have we seen the total blending of sales and marketing today? Should we get rid of all sales teams and just have content marketing teams?
3. How to Move into the Enterprise Successfully:
What are the three biggest mistakes startups make when scaling into the enterprise? What easy wins can they do early in the sales process to enterprises to get a good start? How important are logos? Does social validity really work in enterprise? How should sales teams use discounting in enterprise sales most effectively? What is the right way for sales leaders and CROs to budget for enterprise? Is there a way to test enterprise without committing the company and a lot of resources?
4. How to Build the Best Sales Team Today:
What is the right hiring process for all new sales hires? What are the questions you have to ask in the interviews? What do the case studies entail? What are signals of the best reps? What are the biggest mistakes teams make when hiring new sales reps? What have been Sean's biggest lessons on comp and negotiation with new reps?
Wed, 24 Jan 2024 - 1h 10min
1115 - 20VC: Why Small Markets are Better Than Big Markets, The Biggest Delusion of Early Stage VC, Why AI Investing is like a Horserace and Why The Most Ambitious Companies Growing the Fastest are not the Best Investments with Adam Fisher, Partner @ Bessemer
Adam Fisher is a Partner @ Bessemer Venture Partners and one of the most successful investors in Israel over the last two decades with seed investments in Fiverr, Wix, Melio, HiBob and more. Adam has now made over 60 investments and has had an incredible 23 successful exits. Adam has now been in venture for over 27 years having started his career at Jerusalem Venture Partners in 1996.
In Today's Episode with Adam Fisher We Discuss:
1. Lessons from 27 Years in Venture Capital:
How did Adam first make his way into the world of venture straight out of college? Does Adam agree with Doug Leone that VC has changed from a "boutique, high margin business to a commoditized, low margin industry"? What does Adam know now that he wishes he had known when he started in venture?
2. How to Pick Winners: 23 Exits in 60 Investments:
To what extent does Adam think pattern recognition is a good thing? When is it bad? Does Adam prefer to invest in outsider founders approaching a problem with fresh eyes or insider founders who know the problem back to front? Why does Adam believe that "category creation is BS"? Why does Adam not like to invest in big, hugely ambitious markets? Why are smaller markets best?
3. The Deal: Mastering the Art of Negotiation and the Deal:
How does Adam reflect on his own relationship to price? When doing an investment, does Adam think about who would do the next round? How important is ownership to Adam? Does he want it all on first check? Why does Adam not like to invest in hot AI rounds? What have been Adam's single biggest investing mistakes? How did it change his approach?
4. Mastering the Art of Portfolio Management:
Why does Adam believe that it is impossible to know which of your portfolio will be the breakout winners early on? How does Adam approach reserve allocations with this in mind? How does Adam know when is the right time to sell a position? What does Adam believe was the biggest sin of the zero interest rate environment period?
Mon, 22 Jan 2024 - 1h 11min
1114 - 20VC: How Duolingo Scaled to 8M TikTok Followers, How to Create Viral Content, Why Most Companies Suck at Content Marketing and How to Change & Why You Should Not Work with Content Agencies with Zaria Parvez, Global Social Media Manager @ Duolingo
Zaria Parvez is Duolingo’s Senior Global Social Media Manager where she is famed for scaling Duolingo's TikTok from 50K followers in September 2021 to 8M followers today. The Duolingo TikTok has 143 viral videos (view counts of 1M or higher) due to Zaria’s creativity. What started as a test-and-learn initiative has become Duolingo's most successful social buzz and word-of-mouth initiative to date – all because of Zaria's insights, instincts, and expertise.
In Today's Episode with Zaria Parvez:
1. From College Student to TikTok Star:
How did Zaria make her way into the world of social media and Duolingo? When did Zaria realize the power of TikTok? What did she do as a first step? What does Zaria know now about growing on TikTok that she wishes she'd known when she started?
2. How to Create a Viral Video:
What have been Zaria's biggest lessons in what it takes to create a viral video? What does Zaria mean when she says the best content is "medicine to candy"? What does the ideation process look like for new content ideas? How much budget should be set aside for new content? What does Zaria mean when she says Duolingo's TikTok needs to view like a "sitcom"?
3. How to Tie Success in Content Back to Hard Dollars:
How is "success" in content measured at Duolingo? How fast does Zaria know if a video is a hit or not? What is the right cadence to post? How should companies determine whether content is ultimately successful or not? What is the single metric that Zaria is focused on today?
4. How to Build the Best Content Team:
Why should companies not work with content agencies if they want the best results? Why does Zaria believe you have to hire troublemakers if you want success in content? What are the single biggest mistakes companies make w
Fri, 19 Jan 2024 - 51min
1113 - 20VC: Palantir CTO on The Broken Incentive Structure of How Governments Buy Defence, The Danger of Defence Spending at Historic Lows, How Elections and Wars Change Government Defence Buying & Why Budgets are Anti-Creative with Shyam Sankar
Shyam Sankar is Chief Technology Officer and Executive Vice President of Palantir Technologies in addition to the Chairman of Ginkgo Bioworks. Shyam holds a B.S. in Electrical and Computer Engineering from Cornell University and a M.S. in Management Science and Engineering from Stanford University.
In Today's Episode with Shyam Sankar:
1. Journey to the Top of Defence:
How did Shyam make his way into the world of startups and get a role with Kevin Hartz at Xoom? How did seeing Shyam's parents lose everything impact his mindset and drive? What does Shyam know now that he wishes he had known when he started his career?
2. How the World's Governments Buy Defence:
What is the playbook for selling defence to different governments? Why is the way that governments purchase and procure so broken? If Shyam were head of the DOD, what would he change? Why does the DOD "need to pick winners"? Which governments are the best to work with? Which are the worst?
3. A World In Conflict: What Changes:
How does conflict change the buying process and urgency for governments? How do elections change the buying cadence and process for different governments? Looking forward to 2024, how does Shyam predict the state of different global conflicts?
4. Hiring 101: You Have To Hire Artists:
What have been Shyam's single biggest lessons on what it takes to hire the best of the best? Why does Shyam believe that hiring great people is like talent management in Hollywood? Why does Shyam believe talent should be "shielded from budgets"? What have been some of Shyam's biggest hiring mistakes? How did he learn from them?
Wed, 17 Jan 2024 - 1h 00min
1112 - 20VC: Hubspot Co-Founder Brian Halligan on Leadership Lessons Scaling Hubspot to a $28BN Market Cap | The Best Series A Investment in Venture History & What Makes Sequoia so Successful?
Brian Halligan is the Co-Founder and Executive Chairperson of HubSpot. Brian led the business as CEO for 15 years from Day 1 to a $30BN public company with 7,000 employees. Among Brian numerous achievements, Brian is famed for coining the term "inbound marketing", he is a globally recognised author, he is also an incredible teacher having developed MIT’s popular Scaling Entrepreneurial Ventures class. In addition to all of this, he is also the Co-Founder of Propeller Ventures, a $100 million climate tech venture fund, specializing in ocean innovation investments.
In Today's Episode with Brian Halligan We Discuss:
1. The Makings of a Generational Defining Entrepreneur:
How did the first job as a paperboy lead to the founding of a $30BN company? How does Brian analyse the importance of luck vs skill in success? What is Brian running from? What is he running towards?
2. How to Be the Best Leader from 15 Years as CEO:
What are Brian's biggest lessons in leadership from Elon Musk and Jensen Huang? How has Brian's leadership style changed over time? Why is the way leaders prioritise what they do today completely broken? How can leaders use quarterly goals to prioritise most effectively? Does Brian believe people are born CEOs? Are MBAs worth it for CEOs?
3. How to Build the Best Team:
What is the #1 failure condition of teams today? Why does Brian believe most of your employees are mercenaries and not missionaries? Is that ok? Why do recovery plans never work? Once lost, can trust in teams be regained? Are people destined for certain stages of company growth? Why does culture always break when teams hit 100 people?
4. The Best Deal in VC History:
Why did Hubspot sell 47% of the company to General Catalyst in their Series A? How did Sequoia come to lead their Series D? How much of a needle mover is it for companies and founders to have Sequoia invest? Why did Brian sell secondary to Sequoia in the Series D? Is it the most costly mistake he has made?
Mon, 15 Jan 2024 - 1h 16min
1111 - 20VC Exclusive: Keith Rabois on Rejoining Khosla Ventures
Keith Rabois is a Managing Director @ Khosla Ventures and one of the most respected venture investors of the last decade. Keith has led investments in Stripe, Faire, Ramp, Affirm and many more. Just last week, Keith announced he would be rejoining Khosla from Founders Fund, where he spent an immensely successful 5 years as a General Partner. Prior to Founders Fund, Keith started his career at Khosla where he spent 6 years and led investments in DoorDash, Opendoor, Webflow and more.
In Today's Episode with Keith Rabois We Discuss:
1. The Decision to Rejoin Khosla Ventures:
Why did Keith decide to rejoin Khosla Ventures from Founders Fund? What did Keith miss most that Khosla did, that Founders Fund did not? How did Delian take the news?
2. Comparing Two Great Firms: Founders Fund vs Khosla Ventures:
Investing Style: How does Keith compare the investing styles when analyzing FF and KV? Price Discipline: Which firm is more price-disciplined? Does price discipline even matter? What are the single biggest mistakes Keith has made on price? How did it change how he invests? Founder Type: What sort of founder would choose KV? What founder would choose FF? How did the depth & quality of investment decision-making compare between KV and FF?
3. What It Takes To Win in Venture in 2024:
Liquidity: What have been Keith's biggest lessons on when is the right time to sell positions? Capital Planning: What have been Keith's biggest lessons on the most effective use of reserves? Why does Keith believe if you do not lose some deals as an investor, you are not competing for the right companies? Khosla Ventures recently raised $3BN. How important is the ability to support companies across their lifetime in 2024 vs stage specific?
4. Where is The Best Place to Invest:
Why does Keith think seed is the best place to be investing today? Why despite the better risk/reward profile, does Keith think Series A is not the best place to invest? Does Keith believe we will see the return of growth investing in 2024? What does Keith predict for the M&A market in 2024? Did Figma kill all activity? When will the IPO windows open again? Why would Stripe go out this year?
5. Keith Rabois: AMA:
Why did Keith not want to start his own fund? Will he ever? What have been Keith's biggest lessons from working with Vinod Khosla and Peter Thiel? What were Keith's biggest lessons from Roelof Botha on what it takes to be an effective board member? How does Keith think about bitcoin in 2024?
Fri, 12 Jan 2024 - 1h 06min
1110 - 20VC: Did Figma Kill M&A Markets in 2024, The Three Biggest Mistakes Made in Growth Investing, The Three Requirements Companies Need to Go Public in 2024 with Ed Sim and Jamin Ball
Jamin Ball is a Partner @ Altimeter Capital where he sits on the board of Airbyte, Clickhouse, dbt Labs, Prisma, Tabular. Jamin has also led investments in Deel, MotherDuck, Personio and Starburst. Prior to Altimeter, Jamin spent 5 years at Redpoint where he led investments in Workato, Monte Carlo, Cityblock Health, Root Insurance.
Ed Sim is one of the best seed round investors in venture as the Founder and Managing Partner @ Boldstart, Ed focuses specifically on developer, infra and SaaS at pre-seed and seed round. Over the last decade, Ed has backed some of the best including Snyk, BigID, Kustomer, Front and Superhuman.
In Today's Episode We Discuss:
1. How to Invest Successfully in 2024:
What are the three biggest mistakes growth investors can make in 2024? Why should founders not start a platform company? What were Jamin and Ed's biggest mistakes from the ZIRP era? How does Jamin justify paying an $8BN price for Hopin? What were his lessons?
2. The M&A Markets in 2024:
Did Figma kill the M&A markets for 2024? What should we expect in M&A? Why will private companies buying private companies be a massive segment in 2024? What are Ed and Jamin's biggest tips to founders considering selling their company in 2024?
3. When Will IPOs Come Back:
What will be the catalyst to the opening of the IPO markets? Will Stripe and Databricks go public in 2024? What others should we expect? What are the three requirements for a company to go public in 2024?
4. Firesales: Investors Need Cashback:
Why does Ed believe now is the time in the cycle where late-stage investors want cash back to distribute back to their LPs or to recycle? What should we expect to see in terms of acqui-hires and firesales? What are the different incentives when comparing founders vs early stage VCs vs late stage VCs when it comes to acquisitions?
Wed, 10 Jan 2024 - 1h 06min
1109 - 20VC Crypto Roundtable: How Will US Elections Impact Crypto? Why Will Trump Lean Into Crypto in 2024? Should FTX Investors Have Known About SBF? Will Opensea Ever Be Worth $13BN Again? Will NFTs Come Back with Kyle Samani and Nick Tomaino
Nick Tomaino is the Founder and General Partner @ 1confirmation, one of the leading seed firms fueling the decentralization of the web and society. The fund started with $26M and the firm now has over $1B in assets under management. Nick is famed for being one of the first investors in OpenSea.
Kyle Samani is the Co-Founder and Managing Partner @ Multicoin Capital, one of the leading crypto native funds of the last decade with positions in Solana, FTX, Fractal, and Helium to name a few.
In Today's Episode We Discuss:
1. Moving Away from a Shitcoin Casino:
What will it take for crypto to move away from being shitcoin casino? Why does Nick believe that "crypto has been a free for all and greed got the better of people"? Why does Nick believe that crypto shilling will reduce the amount of violence in the world?
2. FTX: The Biggest Ponzi Scheme in Plain sight:
How does Kyle reflect on SBF and FTX today? Should he have known it was a fraud? How did Nick see so far ahead of time that SBF was not genuine? What are the most striking lessons when comparing Coinbase's Superbowl advert to FTX's?
3. Where Politics and Crypto Collide:
SBF was one of the largest donors to Biden, what does this say about the rise of "crony capitalism"? What candidates running in the election will be best for crypto? Why will Trump win the election and be the first President to rule from a prison cell? Why is the strategy pursued by Gensler and the SEC so flawed?
4. The Great NFT Comeback, The Crypto IPO Season:
What will be the next crypto company to IPO? When? When will NFTs come back? What will cause this? Will Opensea ever be worth $13BN again? What is their future?
Mon, 08 Jan 2024 - 51min
1108 - 20VC: Predictions for 2024: What Happens to Early Stage VC Funding, Do a Load of Venture Funds Die, What do LPs Do in 2024, Does Figma Kill the M&A Market, Will IPOs Comeback & What Does a Trump Administration do for Startups with Jason Lemkin @ SaaStr
Joining Harry in the hot seat today is Jason Lemkin, Founder @ SaaStr and one of the OG SaaS investors of the last decade. The discussion today is broken into two segments:
2023: A Year in Review:
Breakout company Best early-stage fund Best late-stage fund Most surprising event Founder of the Year
2024: Predictions: What is to Come:
Does the IPO window open? Do Stripe, Databricks, and more go public? What happens to early-stage venture markets? Does the growth stage come roaring back? What happens to the M&A market? How does Trump change the startup ecosystem? Will a generation of young VCs be washed out the system? Will a ton of venture firms shut down?
Thu, 04 Jan 2024 - 1h 11min
1107 - 20VC: From a $1.1M Acquisition to $1.4BN in Revenues; The Meteoric Rise of Hoka Running with Deckers CEO, Dave Powers
Dave Powers serves as President and CEO of Deckers Brands, a global footwear and apparel company where he focuses on the company’s five high-performing brands: UGG®, Teva®, Sanuk®, HOKA One One® and Koolaburra®. Prior to Deckers, he held executive leadership roles at Converse and Timberland, where he led worldwide retail merchandising, marketing, visual and store design as well as the creation of a sustainable line of footwear and apparel.
In Today's Episode with Dave Powers:
1. The Unlikely CEO of a Global Footwear Company:
How did Dave make his way into the world of consumer and fashion from the ground up? Why did Dave never think he was the type of person to be a CEO? What does Dave know now that he wishes he had known when he started his career?
2. From $1.1M Acquisition to $1.4BN Revenues: The Hoka Story:
Why did Deckers acquire Hoka for $1.1M? What did they see in this, at the time, futuristic running shoe that no one else saw? Was the growth of Hoka linear or were there needle-moving moments that propelled the brand? What did they do so right that led to their success? What would Dave have done differently in the Hoka journey if he had his time again?
3. From $14.7BN Acquisition to Oprah's Favourite: The UGG Journey:
How much of a needle mover was it for UGG when Oprah added it to her list of favourite items? Why did UGG go through a tough period? What did they do wrong? What does it take to resurrect a brand? How can they bring UGG back to life and make it cool?
4. From Abercrombie to LVMH: An Analysis of the Industry:
How does Dave analyse the rise and fall of Abercrombie and Hollister? Where did it go wrong? What does Dave believe LVMH are the best in the world at? What does he learn from them? How important is it for consumer companies to have a hero product? How can consumer companies scale to mass markets without losing their core audience?
Fri, 22 Dec 2023 - 53min
1106 - 20VC Roundtable: Spotify, Adobe & Linkedin CPOs on How AI Changes The Future of Product, Why AI is Now the Product, How TikTok Changed Product, Why Cost is the Biggest Barrier to LLM Usage & Why Incumbents Can Adopt AI Faster Than Any Prior Innovation Cyc
Gustav Söderström is the Co-President, CPO & CTO at Spotify. Gustav has been instrumental in taking Spotify from a 30-person operation in Sweden when he joined to being the global leader of the space.
Scott Belsky is Adobe’s Chief Product Officer and Executive Vice President, Creative Cloud. Scott oversees all of product and engineering for Creative Cloud, as well as design for Adobe.
Tomer Cohen is the Chief Product Officer @ Linkedin where he is responsible for setting and executing the global product strategy at LinkedIn.
In Today's Episode on How AI Changes The Future of Product and Design We Discuss:
1. Why AI Is Now the Product that UI Serves:
Why does Gustav believe that AI is now the product? How has the importance of UI changed with the rise of AI? How did TikTok change the product paradigm over the last few years?
2. What Matters More Models or Data:
What is more important the size of the model or the amount of data a company has? Will companies use many models at the same time? Why will companies using many models at once create a huge opportunity for startups? Will every company have their own model? What will be the decision-making framework of whether to have your own model or leverage another? How does the rise of AI change how companies approach data acquisition, collection and cleaning?
3. The Workforce Needs to Change with AI:
How do product leaders and teams need to change in an AI-first world? What do designers need to do to stay up to date in an AI-first world? What does it mean to be good at prompting? How can people get good at prompting? Why will AI kill companies that charge by the hour? Why will seat pricing die in a world of AI? What will be the business model for AI?
4. Incumbents vs Startups: Who Wins:
Do incumbents win in a world of AI or do startups? Why is AI primed for incumbents to win and move fast in a way they could not in prior technology cycles? What are the biggest hurdles and challenges incumbents have to face that startups do not? What are the biggest barriers that startups have to win in a world of AI that incumbents do not have?
Wed, 20 Dec 2023 - 50min
1105 - 20VC: Why Now is the Best Time to Invest in Emerging Managers, Biggest Mistake Emerging Managers Make When Fundraising & Investing Lessons from Investing $1.5BN Per Year and Being Early Investors in Thrive, a16z and Founders Fund with Peter Lacaillade
Peter Lacaillade is a Managing Director @ SCS Financial Services where he leads its private investment program where he oversees the firm’s activities in private equity, opportunistic credit and private real assets. Peter has been an early backer of Thrive, Founders Fund, a16z, Greenoaks and 20VC. Before SCS, Peter was an Associate at HarbourVest Partners in its Secondary Group where he analyzed venture capital, growth equity and buyout investments.
In Today's Episode with Peter Lacaillade We Discuss:
1. Becoming One of the Great LPs in Venture:
How did Peter make his way into the world of fund investing as an LP? What does Peter know now that he wishes he had known when he started as an LP? Why does Peter believe now is the best time to be investing in newer, emerging managers?
2. How to Pick the Best Venture Managers:
What are the commonalities in the best VCs Peter has invested in? How important is track record for Peter when evaluating managers? What mistakes has Peter made when it comes to manager selection? What did he learn? How do the best managers build relationships with their LPs?
3. Building a Portfolio That Can 5x:
In a venture fund portfolio, what is the distribution between those that outperform, perform as planned and then underperform? How does Peter invest in both large franchises and emerging managers with a barbell approach? How much in established franchises and how much in emerging managers? Are managers actively marking down their portfolios in the last 18 months? Who has been the best at this and who has been the worst? How much should portfolios be marked down? How does Peter evaluate the compression of deployment timelines we saw in the last 18 months?
4. A Breakdown of the LP Landscape:
Family Offices: What are the biggest dangers of having family offices as LPs? Why do multi-family offices tend to be better? Endowments: Are they really as stable as people think they are? What separates a good vs great endowment? Who stands out? Fund of Funds: Why does Peter think fund of funds deserve more credit? How should managers think about working with FoFs most effectively? What is the right level of concentration managers should have between these different LP profiles? What are the biggest mistakes emerging managers make when approaching LPs?
Mon, 18 Dec 2023 - 1h 02min
1104 - 20VC: Cotopaxi: From Selling $6M of Pool Tables to Scaling $150M in Revenues and Challenging Patagonia, Fundraising Lessons from 100+ Rejections & What Founders Do Not Understand About VC with Davis Smith, Founder @ Cotopaxi
Davis Smith is the Founder and Chairman of Cotopaxi, an outdoor brand with a humanitarian mission. The company has assisted over 4 million people living in poverty. The company has been profitable for the last 4 years and is expected to do $160M in revenue in 2023, up from $55M just two years before. In April 2023, Davis resigned after 10 years as CEO to lead a mission for his church in Brazil for three years. Davis is an EY Entrepreneur of the Year and was recognized as Utah’s Businessperson of the Year in 2022. He is an adventurer who has floated the Amazon on a self-made raft, kayaked from Cuba to Florida, and explored North Korea.
In Today's Episode with Davis Smith We Discuss:
1. From Selling $6M Worth of Pool Tables to the Amazon of Brazil to Founding Cotopaxi:
How did Davis scale a pool table business to $6M in revenue? What were Davis' biggest takeaways from building the Amazon of Brazil, raising millions in VC funding and the business failing? How did depression and 36 hours on a sofa lead to the a-ha moment for Cotopaxi?
2. The Billion Dollar Company, Rejected by 100 Investors:
How was the early fundraising journey for Davis with Cotopaxi? Why did so many investors say no? What was the best VC meeting he has ever had? Why do women understand Cotopaxi better? What does Davis believe are the biggest misalignments between VCs and Founders? Why does Davis believe we need a new type of financial product to fund long term projects? What are the biggest elements of fundraising that Davis believes founders do not understand?
3. Scaling Cotopaxi to $150M in Revenue:
What are Davis' biggest lessons on what works and what does not from scaling Cotopaxi to $150M in revenue? Why did Davis not lay anyone off but decide everyone should take a pay cut instead? How did that go down? Why does letting people leave work earlier lead to better talent wanting to join your company? Why does Davis believe that you absolutely can build a huge business with balance in your life?
4. Life, Parenting, Marriage:
Why does Davis believe that so many entrepreneurs chase the wrong thing? What do they chase? What should they be chasing instead? How does Davis analyze his relationship to money today? Does it make you happy? What does great parenting mean to Davis? How has that changed over time? How does marriage change when comparing pre-kids and post-kids? Was Davis nervous about becoming a father for the first time at the age of 24?
Fri, 15 Dec 2023 - 58min
1103 - 20Sales: How to Close Sales When Selling to CFOs, How to Guarantee You Win Every Renewal, Core Questions All CFOs Ask Today When Buying, Why Revenue Operations is the Most Important Role in a Company with Steve Goldberg, CRO @ Salesloft
Steve Goldberg is the Chief Revenue Officer at Salesloft, the sales engagement platform that was acquired by Vista in 2022 for $2.3BN. Prior to Salesloft, Steve was Group Vice President of Enterprise at Yext and before that was a Senior VP @ InsideSales.com.
In Today's Episode with Steve Goldberg:
1. Becoming a Sales Leader:
When did Steve first fall in love with sales? Why does Steve believe sales is more psychology than anything else? What can sales reps do to master the psychology of their prospects? What does Steve know now about sales that he wishes he had known in the beginning?
2. How to Close Prospects Faster Than Ever:
How does Steve build relationships with prospects very fast? What questions does he ask? How does Steve know if he is really speaking to a buyer? What are the signals? How does Steve advise sales reps on getting multiple relationships within an account to prevent the potential of losing your champion? How does Steve feel about discounting? When is the right time to do it?
3. How To Do The Best Deal Reviews:
What makes good vs great deal reviews? Who is invited? Who is not? Who sets the agenda? Who is responsible for what? How do deal reviews change throughout the quarter and throughout the year? Is a deal slipping into the next quarter an acceptable excuse for a sales rep to give?
4. How to Ensure Renewals in a World When They are Not Guaranteed:
Have all budgets centralized back to the control of the CFO? Are people right to say that no CFOs are buying new technology today? What is the best way to show to customers the value you provide? Why does Steve believe revenue operations is the most valuable role within an org?
Wed, 13 Dec 2023 - 49min
1102 - 20VC: Why Founders Should Take as Many VC Meetings as Possible, Should Founders Meet Associates, How to Get Intros to the Best VCs, How To Extract the Most Value From Your Investors, Why Post IPO Operators Are the Best Angels with Sam Corcos @ Levels
Sam Corcos is the Co-Founder & CEO @ Levels, the company helping you see how food affects your health with data from biosensors like continuous glucose monitors (CGMs). To date, Sam has raised over $89M for Levels from the likes of a16z (Jeff Jordan sits on his board), Founder Collective, Breyer Capital and Shrug Capital to name a few. Prior to Levels, Sam founded two prior companies, CarDash; a Y Combinator company that makes automotive repair and maintenance convenient. Before Cardash, Sam founded, Sightline Maps, an intuitive platform for 3D printing and visualizing topographical maps, marketed primarily towards the U.S. military.
In Today's Episode with Sam Corcos:
1. The Founding Moment:
What was the a-ha moment for Sam with the founding Levels? What were the big mistakes Sam made with prior companies that he did not take with him to Levels? What does Sam know now that he wishes he had known when he started Levels?
2. How to Fundraise Like a Pro:
Why does Sam believe that founders should take as many meetings with VCs as possible? What are the biggest mistakes founders make when meeting investors? Should founders meet with associates in the fundraising process? What does Sam mean when he says, "you have to create theater" when pitching?
3. How to Extract the Most Value from Your Investors:
What have been Sam's biggest lessons on how to put your investors to work? What is the right and most strategic way to ask investors for specific help? How can founders create a competitive environment where VCs are competing to help? Which investors have been the most helpful? Why are post-IPO operators the best angels to have as investors? How has the a16z platform team been such a needle mover?
4. How to Find Your Partner and Master Parenting:
What does Sam mean when he says he had a "one pager" in what he wanted in a partner? What was in the one-pager? How did dates respond? What are the biggest mistakes people make when dating? What is Sam most nervous about on becoming a parent? How does Sam think having a child will impact his marriage?
Mon, 11 Dec 2023 - 1h 08min
1101 - 20VC: $18BN Market Cap and $1BN in ARR in 8 Years; Samsara | How to Find Product Market Fit Reliably | How to Create a Multi-Product Company | The Pros and Cons of Serial Entrepreneurship with Sanjit Biswas, Founder & CEO @ Samsara
Sanjit Biswas is the Founder and CEO @ Samsara, allowing businesses that depend on physical operations to harness Internet of Things (IoT) data. Over the last 8 years, Sanjit has scaled Samsara to $1BN in ARR and a public company with tens of thousands of customers. Before Samsara, Sanjit was the CEO and co-founder of Meraki, one of the most successful networking companies of the past decade. Sanjit grew Meraki from his Ph.D. research into a complete enterprise networking portfolio. Meraki's sales doubled every year from inception and in 2012, Cisco acquired Meraki for $1.2 billion. Huge thanks to Doug Leone for some fantastic question suggestions pre this episode.
In Today's Episode With Sanjit Biswas We Discuss:
1. From Founding to $1BN in ARR in 8 Years:
What was the founding a-ha moment for Sanjit with Samsara? Sanjit sold his prior company Meraki for $1.2BN, what worked with Meraki that Sanjit took with him to Samsara? What did not work that he left behind? What does Sanjit know now that he wishes he had known when he started Samsara?
2. The Man Who Found Product Market Fit Time and Time Again:
What is the one single moment that Sanjit believes you know you have product market fit? What are the biggest mistakes founders make when chasing product market fit? How does being a bootstrapped company change how a company approaches chasing PMF?
3. Mastering a Multi-Product Company:
How do you know when it is the right time to launch a second product? Does the second product have to make the first product better? What are the biggest mistakes companies make when going multi-product?
4. The Art of Great CEOship:
Does Sanjit believe that the best CEOs are the best capital allocators? What has been the single best and single worst capital allocation decision in Samsara's journey? What are the biggest mistakes Sanjit has made in leadership? How did he learn and grow from them?
Fri, 08 Dec 2023 - 53min
1100 - 20VC: Ramp's Product Playbook: How To Hire Product Teams, How to Run Sprints, How to Increase Product Velocity, When and How to Go Multi-Product with Geoff Charles, VP Product @ Ramp
Geoff Charles is the VP of Product at Ramp, leading the product management, operations, and support teams. Prior to Ramp, Geoff helped spin off Mission Lane and scale credit products to millions of consumers. He started his career advising Fortune 100 financial services companies.
In Today's Episode with Geoff Charles We Discuss:
1. How to Become a Product Leader:
How did Geoff make his way into the world of product? What are the single most important skills for product people to learn early? What are the biggest mistakes that product people make early in their career?
2. When and Who to Hire for the First Product Team:
When is the right time to hire your first product people outside of founding team? Why are the best product teams in the early days professional services teams? What is more important; the person has stage or sector experience, when joining? Should you hire senior product people or junior product people as the first hires?
3. How to Increase Velocity Using Sprints:
How does Geoff and Ramp use two-week sprints to have insane product velocity? How are they structured? How are goals set? Who is included? What makes a good vs a bad sprint? How is accountability tied to sprints? When do two-week sprints no longer become possible? What happens then?
4. Going Multi-Product, Will Incumbents Kill You and Product Re-Usability:
When is the right time to add a second product? What are the biggest mistakes companies make when going multi-product? Why is it unlikely that an incumbent is the one to kill you? What competitor should worry you? What does Geoff mean when he speaks of "product re-usability"? Why is it crucial to velocity?
Wed, 06 Dec 2023 - 52min
1099 - 20VC: From Construction Worker to Billionaire CEO; The 21-Year Epic Journey of Procore to an $8.6BN Company, Advice from Tobi at Shopify on Being a Great CEO & Why The Idea of "Becoming an Entrepreneur" is BS with Tooey Courtemanche
Tooey Courtemanche, Jr. is the Founder, CEO, President, and Chairman of the Board of Procore. He founded Procore in 2002 with a mission to connect everyone in construction on a global platform. After 13 years of business, the company had just $9.6M in revenue, 8 years after that they have over $890M in revenue. Under his leadership, Procore has grown to become a leading global provider of construction management software, connecting over 2 million users across 150+ countries. Today Procore trades on the New York Stock Exchange under the ticker PCOR. Huge thanks to Brian @ Bessemer and Will @ Iconiq for some amazing question suggestions today.
In Today's Episode with Tooey Courtemanche:
1. The Founding of a $8.5BN Company:
How did Tooey's wife, Hilary and their house-building lead to the idea for Procore? What does Tooey know now that he wishes he had known when he started? Did Tooey always know he would be a success? What was the moment of most doubt?
2. The 13-Year Journey to $9.6M in Revenue:
Why did it take so long to hit the $10M revenue mark? What changed in 2015? What is Tooey's biggest advice to founders and investors who face market timing risk? Why was Tooey laughed out of VC offices in 2008? What are his biggest pieces of advice to founders raising from VCs today? How does Tooey advise founders on the balance between vision and sticking to a mission vs realising when it is not working and giving up?
3. The Art of Great CEOship:
What advice did Tobi @ Shopify give Tooey on being a great CEO? How did it impact his approach? What are the biggest differences between the reality of being a CEO and the Instagram version? What have been Tooey's biggest lessons on hiring? Why does hiring smart, ambitious but not humble people never work? Why does Tooey believe the idea of "becoming an entrepreneur" to be BS?
4. Parenting, Money and Marriage:
Why does Tooey believe great parenting is like great CEOship? How does one bring up children to be ambitious and humble in a very privileged upbringing? What are the secrets to being there as a husband while also being a rockstar CEO? How does Tooey reflect on his own relationship to money and wealth today?
Mon, 04 Dec 2023 - 1h 14min
1098 - 20VC: HelloFresh CEO on Why When You Raise VC You Only Have Two Options, Why Your IPO Price is Irrelevant, Why Timing is So Important in Going Public & Why D2C is Not Dead with Dominik Richter
Dominik Richter is the Founder & CEO @ HelloFresh, one of the largest direct-to-consumer businesses of the last decade and the #1 recipe box delivery service. Fun fact, two of the three biggest cooking facilities in North America are HelloFresh facilities with the third being Disney World Orlando. Dominik has made over 40 angel investments in the EU and the US.
In Today's Episode with Dominik Richter We Discuss:
1. The Founding of One of the Largest D2C Companies:
How did Diminik's dreams of being a footballer translate to founding HelloFresh? What does he know now that he wishes he had known when he started? Why does Dominik respect the brands that large banks have built?
2. To Raise or Not to Raise:
Why does Dominik believe when you raise VC, you either have to sell or go public? What are the single biggest differences between raising in the US vs Europe? What are Dominik's biggest pieces of advice to founders raising today? Why does Dominik believe so many of the D2C companies should not have raised venture funding?
3. The IPO: When, How and Why:
Why did Dominik decide to IPO the business so early? Why does Dominik believe that the first-day trading price is irrelevant? Why does Dominik believe that timing is so important when going public? What are the biggest pros and cons of being public?
4. The Rise and Fall of D2C:
D2C has been crushed lately, why? Is this the end of D2C as a category? Is D2C an investable category for VC? HelloFresh is one of the biggest and $2.5BN market cap? What have been the best and worst resource allocations Dominik has made? Do recessions help or hurt recipe box businesses?
Fri, 01 Dec 2023 - 55min
1097 - 20Growth: The Golden Rule to $100M in ARR, Why CAC to LTV is BS Early On, Why Your First Growth Hire Should Be a Former Founder & How Ramp Does 200 Growth Experiments Per Quarter with Guillaume Cabane
Guillaume Cabane is a growth advisor to high-growth SaaS Startups, including Ramp, Spot, Airbyte, G2, Gorgias, Metadata, Madkudu, and others. Guillaume held VP of Growth roles at Drift, Segment, and other successful startups, where he helped them grow from ~50 to 300. Prior, Guillaume spent 6 years at Apple.
In Today's Episode with Guillaume Cabane We Discuss:
1. Entry into Growth:
How did Guillaume make his way into the world of growth? What are 1-2 of his biggest lessons from him time at Segment where he 4x revenue? What does Guillaume know now that he wishes he had known when he entered growth?
2. Enterprise vs SMB & CAC/LTV:
Why does Guillaume think it is harder to go enterprise down than SMB up? What are the biggest mistakes companies make when scaling into enterprise? What are the biggest mistakes startups make with product-led-growth motions? Why does Guillaume believe it is impossible to analyse CAC/LTV in early companies?
3. Activation, Engagement and KPI Setting:
What are the biggest mistakes companies and teams make in activation? What can growth and marketing teams do to guarantee engagement in prospects? Why are all KPIs not tied to revenue BS?
4. Hiring the Growth Team:
What are the core characteristics of great growth hires? How quickly does it become apparent when you have made a bad growth hire? Why do founders make the best profiles when hiring your first growth hire? What are the biggest mistakes Guillaume has made when hiring for growth?
5. Why Growth is Like Venture:
What is the secret to building a great growth portfolio? Why is it impossible to scale to $50M ARR with only one good channel? What is the right way to spread resources across channels? When is the right time to add new channels and diversify?
Wed, 29 Nov 2023 - 1h 04min
1096 - 20VC: Keith Rabois and Mike Shebat on Creating an Olympian Mindset to Work Ethic, Why First-Time Founders are Better Than Serial Entrepreneurs, Why Remote Work Does Not Work, Why the Best Founders Always Start in their Teens & Why Companies are Cults?
Keith Rabois is a General Partner @ Founders Fund, one of the world's best venture funds with a portfolio including the likes of Facebook, SpaceX, Anduril, Tesla and many more. For the last 23 years straight, Keith has either invested in or founded a $BN company. Keith is also the Co-Founder and CEO @ Openstore, the company that will buy or run your Shopify business.
Mike Shebat is the Founder and CEO @ Traba, the company providing industrial staffing when and where you need it. To date, Mike has raised $49M with Traba from some of the best including Founders Fund, General Catalyst and Khosla Ventures.
In Today's Episode We Discuss:
1. What it Takes to Build a Great:
Why does Mike expect everyone to work in office 12 hours per day, 4 days per week? At what point does an extra hour of work not lead to more output? What are the expectations in terms of emails, out of office, the weekends? Keith, from the 23 BN companies you have worked with, is this insane work ethic aligned to all of them? Which had it? What did not? What core components of PayPal's work ethic made it so strong? What does Keith mean when he says Linkedin could and should have been 5x bigger?
2. The Hiring Process for the Swat Team:
What does the hiring process look like for this type of work environment? What are the signs that someone is really aligned to it vs faking it for the interview process? What have been Keith's biggest lessons on both compensation and title in the hiring process? Why does Keith believe that culture is like concrete? What are the biggest mistakes he has made on culture and what would he have done differently?
3. First-Time Founders, Innate Entrepreneurs & Europe's Failing:
Does Keith agree the best founders always show signs of early entrepreneurship in their teens? Why does Keith prefer first-time founders to serial entrepreneurs? Why are they better? Why does Keith believe that Europe has not created a $100BN company since 1990?
4. Remote Work, Network Effects and Baseball:
Why does Keith believe being great in venture is like baseball? Why does Keith and Founders Fund not invest in remote teams? How does he explain Gitlab? Why does Keith believe Airbnb has the best network effect he has ever seen?
Mon, 27 Nov 2023 - 57min
1095 - 20VC: AI's Biggest Questions: The Commoditisation of LLMs, Open vs Closed: Who Wins, Model Size vs Data Quality, Why Google are Vulnerable and Apple are the Dark Horse
Des Traynor is a Co-Founder of Intercom, and has built and led many teams within the company, including Product, Marketing, and Customer Support.
Yann LeCun is VP & Chief AI Scientist at Meta and Silver Professor at NYU affiliated with the Courant Institute of Mathematical Sciences & the Center for Data Science. He was the founding Director of FAIR and of the NYU Center for Data Science.
Emad Mostaque is the Co-Founder and CEO @ StabilityAI, the parent company of Stable Diffusion. Stability are building the foundation to activate humanity’s potential.
Jeff Seibert is the Founder & CEO @ Digits, building the future of AI-powered accounting. Digits have raised funding from the likes of Peter Fenton @ Benchmark and 20VC.
Tomasz Tunguz is the Founder and General Partner @ Theory Ventures, just announced last week, Theory is a $230M fund that invests $1-25m in early-stage companies that leverage technology discontinuities into go-to-market advantages.
Douwe Kiela is the CEO of Contextual AI, building the contextual language model to power the future of businesses.
Cris Valenzuela is the CEO and co-founder of Runway, the company that trains and builds generative AI models for content creation.
Richard Socher is the founder and CEO of You.com. Richard previously served as the Chief Scientist and EVP at Salesforce. Before that, Richard was the CEO/CTO of AI startup MetaMind, acquired by Salesforce in 2016.
In Today's Episode We Discuss:
Will foundational models become commoditized? Who are the major players? What are their different strengths? Who will win? Who will lose? How important is the size of the model vs the quality of the data?
2. Open vs Closed:
What are the biggest pros and cons of an open ecosystem for LLMs? Why is it naive to think that open-source LLMs will prevail? What will determine which method wins?
3. An Analysis of the Incumbents:
Why is Google the most vulnerable? What can they do to regain ground? Why is Apple the sleeping giant? How could they win the next wave of AI? What should Amazon do today to compete with Microsoft?
4. The Future: Doom and Gloom?
Why is it ridiculous to assume AI systems want to dominate? Why will AI create a renaissance of creativity and human freedom? What role should regulation play in the advancement and progression of AI?
Fri, 24 Nov 2023 - 33min
1094 - 20VC: Why OpenAI Will Become an Infrastructure Play, Why Apple Will Win in an AI World, Why Google is the Most Vulnerable Incumbent, Will LLMs Be Commoditised, Which Startups Are Thin vs Thick Wrappers on Top of LLMs with Jeff Seibert, Founder @ Digits
Jeff Seibert is the Founder & CEO @ Digits, building the future of AI-powered accounting. Digits have raised funding from the likes of Peter Fenton @ Benchmark and 20VC. Jeff previously served as Twitter's Head of Consumer Product, a position he came to following the acquisition of his prior company, Crashlytics. Today, Crashlytics is the de-facto mobile crash reporting solution for iOS and Android and runs on over 6 Billion monthly active smartphones worldwide.
In Today's Episode with Jeff Seibert We Discuss:
1. The Art of the Pivot:
What are Jeff's biggest pieces of advice to founders pivoting? How do you know when you have enough data to make the decision to pivot? What are the single biggest mistakes founders make when pivoting?
2. AI: Who Wins and Who Loses:
Why does Jeff believe that OpenAI will transition into an infrastructure play? What are the most significant challenges OpenAI will face moving forward? Why does Jeff believe that Apple are best positioned to win in an AI world? Why does Jeff believe that Google are the most vulnerable incumbent? What would Jeff do if he was CEO of Google?
3. LLMs: What Happens Now:
Will we see the commoditization of LLMs? What are the biggest misconceptions people have on training and fine-tuning LLMs? Will we see LLMs increasingly specialise to vertical-specific models or will they remain horizontal? What is the difference between a thick and a thin wrapper when building on top of LLMs?
4. Angel Portfolio in Review:
How many angel checks has Jeff written? How many failed? How many home runs? Does Jeff believe that company valuations are being kept artificially high? How did Jeff make 200x selling through the secondary market for a now failing company? What are Jeff's three biggest pieces of advice for angels today?
Wed, 22 Nov 2023 - 58min
1093 - 20VC: The Ultimate Hiring Playbook: Five Questions to Ask Every New Hire | What Makes Truly Great Leaders and How They Give Feedback | Do VCs Really Add Value; Lessons from Hard Fundraises with Matteo Franceschetti, Co-Founder @ Eight Sleep
Matteo Franceschetti is the Co-Founder and CEO @ Eight Sleep, a company dedicated to fueling human potential through optimal sleep. To date, Matteo has raised over $160M for the business from the likes of Founders Fund, Ryan Petersen, Naval Ravikant, Kevin Hart, AROD and many more.
In Todays Episode with Matteo Franceschetti We Discuss:
1. Why Did Sleep Need "Solving":
Why did Matteo decide he wanted to spend decades of his life-solving sleep? If Matteo has known how hard it was going to be, would he do it again? What does Matteo know now that he wishes he had known at the start of the journey?
2. Hiring the Best Team:
What is Matteo's playbook for hiring? What are the five questions that Matteo asks in every interview? What are big red flags? What are strong signals of great talent? If people have been let go in a RIFF, is that a concern? How does Matteo construct hiring panels? What vote count is enough for an approved hire? What are Matteo's biggest lessons on title and pay a new hire receives? What are some of Matteo's biggest lessons when it comes to firing people?
3. Funding the Business:
What was the hardest round to raise? Why? Are investors justified in their skepticism of hardware? What are the single biggest pieces of advice Matteo would give to founders on raising? How impactful has it been having Keith Rabois and Founders Fund as an investor? Do VCs really add value?
4. Mastering Health, Sleep and Nutrition:
How does your diet impact the quality of sleep you have? How does exercise and the time of exercise impact your sleep? What are some common rules on sleep that are BS and myths? What are some of the most non-obvious truths about getting great sleep?
Mon, 20 Nov 2023 - 1h 39min
1092 - 20VC Will Seed Pricing Remain High | Where is the Funding Crunch? | Three Core Elements Required to Raise a Series B/C | Why AI is Like the Lottery Today | Why Now is the Best Time to be Investing in Crypto | Why Investors Do Not Want to Reprice Companies
Rebecca Kaden is a Managing Partner @ Union Square Ventures, one of the leading early-stage firms of the last decade with investments in Twitter, Twilio, Coinbase and many more.
Nicole Quinn is a General Partner @ Lightspeed where she has led investments or sits on the board of Calm, Cameo and LunchClub to name a few.
Eurie Kim is a Managing Partner @ Forerunner Ventures, the leading early-stage consumer fund. Eurie has led investments and sits on the board of Oura, The Farmers Dog, Curology and more.
In Today's Roundtable We Discuss:
1. Seed Rounds:
Is it even possible for traditional seed funds to play in a world of multi-stage funds investing so aggressively at the seed stage? Is seed immune to the macro environment? Will seed pricing remain as high as ever? What advice does the team have for seed founders approaching a Series A? What do they need?
2. Series A:
How is the Series A market looking today? Is there a crunch at the Series A? To what extent are valuations compressed at the Series A? What 3 core elements do companies at the A stage, looking for a Series B next, need to focus on?
3. Series B and Beyond:
Is the real crunch at the Series B? Why are down rounds so much better than structured rounds for companies raising? Will we see a wave of M&A in the next 12 months?
4. Crypto, AI and Hot Takes:
Why is now the best time to be investing in crypto? Why is investing in AI a lottery right now? What is the most controversial thing that each believes today?
Fri, 17 Nov 2023 - 40min
1091 - 20VC: How to Survive and Thrive in a World of OpenAI, Are LLMs Being Commoditised, Where Does the Value Lie; Infrastructure or Application Layer, How Apple Could Win in a World of AI, How Amazon Could Threaten OpenAI and Why Google Struggle with Des Trayn
Des Traynor is a Co-Founder of Intercom, and has built and led many teams within the company, including Product, Marketing, and Customer Support. Today Des leads all Intercom’s R&D efforts, and parts of Intercom’s marketing.
In Today's Episode with Des We Discuss:
1. From Consultancy to Founding a Unicorn:
What was the founding a-ha moment for Des and the team with Intercom? Why does Des believe that most startup advice is BS and outdated in 5 years? What does Des know now that he wishes he had known when he started?
2. LLMs: The World is Not Equal:
What does Des mean when he says the world of LLMs is not equal? How do the different LLMs very in quality, price and speciality? Does Des agree with Alex @ Nabla, "the best companies in the future will work with many LLMs at the same time and switch between them for different things"? To what extent does Des believe LLMs will be commoditised and it will be a race to the bottom? Would Des be a buyer of OpenAI at a $90BN price? Why not?
3. How to Survive in a World of OpenAI:
What two simple questions will determine if Open AI will kill your existing business? What 3 criteria will determine if there is a new business to be built on top of OpenAI? What is the different between a thin layer on top of an LLM and a thick wrapper with real value? Which traditional incumbents are most vulnerable? What should they do in this new world? How long does it take for incumbents to really be impacted?
4. The Titans of Tech: Who Wins:
Why does Des believe that Apple could be a massive winner in the next wave of AI? Why does Des believe that Google have not been impressive and failed to keep pace? Why does Des think OpenAI should be wary of Amazon? What could they do to threaten them? What opportunity does Facebook have here? How could Instagram and Whatsapp win?
5. Startup and Investing 101:
Why does Des believe that every founder should write a blog post per week? Why does Des believe that most B2B marketing sucks? What makes great B2B marketing? What are Des' biggest lessons from the Hopin journey? How has Des' angel investing changed in the last year with the rise of AI?
Wed, 15 Nov 2023 - 1h 18min
1090 - 20VC: Flexport's Ryan Petersen: Reflections on Leadership from 13 Years Leading Flexport, Why Velocity not Speed is Most Important in Company Building, How Money Creates Inefficiencies in Scaling, The Future of Trade with China & Why Remote Work is so Cha
Ryan Petersen is Founder & CEO @ Flexport, a leader in global supply chain technology. In 2022, Flexport moved more than $26 billion of merchandise. Over the last 10 years, Ryan has raised close to $2.5BN for the business with the latest valuation pegging the business at $8BN. Prior to starting Flexport, Ryan was the founder and CEO of ImportGenius, a premier provider of transaction data for the global trade industry.
In Today's Episode with Ryan Petersen We Discuss:
1. The Origins of a Generational Defining Leader:
What did Ryan want to be when he was growing up? How did scooters and motorbikes in China lead to the idea for Flexport? What does Ryan know now that he wishes he had known when he started Flexport?
2. Speed and Money: The Secrets To Execution:
Does Ryan believe speed is key to execution? What is the difference between speed and velocity? What advice does Ryan have to founders who raise a lot of money? How should it impact hiring? What are the most common ways founders become inefficient post-fundraising? Why does Ryan look to invest in founders with jaded pasts and a chip on their shoulder?
3. The Art of Resource Allocation:
Are the best CEOs the best resource allocators? What is the single best resource allocation Ryan has made? What did he learn? What is the worst? What did he learn? What have been Ryan's biggest hiring mistakes? How did that change his approach?
4. The Wider World:
Is Ryan long or short on China? Why? Will we see global trade become nationalized? Why? Will we see interest rates raised further? What impact does that have on trade? What has been the impact of war on trade and the shipping industry?
5. Ryan Petersen: The Father and Husband:
How has having kids changed how Ryan approaches leadership and management? How does Ryan juggle 2 young kids and leading a 2,500 person company? How does Ryan retain romance with his wife while also being a full-on CEO of a large co? Does money make you happy? What does it help with? What does it not help with?
Mon, 13 Nov 2023 - 57min
1089 - 20Sales: Five Lessons Scaling Snowflake to $1BN ARR, Why Customer Success is BS and Should Be Removed, Why All Sales Reps Should Do Eight Calls Per Week & Why You Should Hire a Head of Sales Sooner Than You Think with Chris Degnan, CRO @ Snowflake
Chris Degnan serves as Snowflake’s Chief Revenue Officer and has been with the company since 2013. Starting as employee #13 and Sales employee #1, Chris built a go-to-market strategy from the ground up, driving sustained high growth and global reach. Under his sales leadership, Snowflake has grown its annual product revenue from $0 to over $1 billion. Prior to Snowflake, Chris served in Sales leadership roles at EMC and Aveksa, and worked in enterprise sales at Informatica and Covalent Technologies (acquired by VMware).
In Today's Episode with Chris Degnen We Discuss:
1. From SDR To World Leading CRO:
How did Chris first make his way into the world of sales? What does he know now that he wishes he had known when he started in sales? What are the single biggest mistakes young sales people make today scaling their careers?
2. The Secret to Hitting Quota in Sales:
Why does Chris believe all reps need to do 8 customer calls per week? How do the best sales reps approach sales prospecting today? Is cold outbound dead? How does Chris advise his teams on cold calls and emails? What are the best reasons reps should say no to customers? Should reps be discounting today? What is an acceptable level?
3. Sales and Product: The Most Important Relationship:
Why does Chris believe sales and product is the most important relationship? What can leaders do to ensure sales and product communicate effectively? How does Chris use sales calls today both with his sales team and with product? What are the single biggest reasons comms between sales and product breaks?
4. Mastering Sales Leadership:
How does Chris approach sales forecasting? What works? What does not work? Does Chris celebrate when quota is hit? How do you find the balance between pushing further and harder but also celebrating the wins? How do the best sales leaders train and develop their talent? What do the worst do?
5. Customer Success is BS: Professional Services for the Win:
Why does Chris believe that customer succeed is BS and you should get rid of it? Why are professional services so much better? How should the org be structured then when removing CS and adding professional services? Who is then responsible for upsell?
Fri, 10 Nov 2023 - 57min
1088 - 20VC: From Leading the BBC to Leading Venture Capitalist, The Biggest Similarities and Differences Between the Best Founders and the Best Actors & The Future of Media; Legacy vs New, The Creator Economy, The Rise of TikTok and more with Danny Cohen
Danny Cohen is the President of Access Entertainment, a division of Len Blavatnik's Access Industries. Access Entertainment’s corporate investments include film and television studio A24; Europe’s fastest-growing company Tripledot Studios; creator economy leader Spotter; and a new immersive arts’ experience launched in collaboration with David Hockney and Lightroom. Before joining Access, Danny was the Director of BBC Television where he had responsibility for all of the BBC's network channels and the greenlighting and production of the BBC's drama, entertainment, comedy, arts, history, science, educational content and documentary.
In Today's Episode with Danny Cohen We Discuss:
1. From Leading the BBC to Investing for Len Blavatnik:
How did Danny make his way from leading the BBC to investing for Len @ Access? What was he most nervous about when making the transition to investing? What has been the hardest investing skill to learn?
2. Great Founders are Like Great Actors:
What are the biggest similarities in what makes the best founders and the best actors? How are the best founders different from the best actors? Why does Danny believe the risk that an actor takes is so different to the risk founders take? How does Danny feel both founders and actors can and should be managed?
3. The Future of Media:
What does Danny mean when he says he looks for "eyeballs and attention" when investing? How does legacy media respond to the threat created by social media today? How does AI change the future of content creation and distribution today? How do the strikes in Hollywood impact the future of content supply?
4. Marriage, Children and Loneliness:
Why does Danny believe that loneliness will continue to be the biggest problem we face? What are Danny's biggest pieces of advice from 17 years of happy marriage? Why did Danny decide to not have children? What did that decision-making process look like?
Wed, 08 Nov 2023 - 50min
1087 - 20VC: From $4.1BN to $142M Market Cap; Why Public Markets Have Written Allbirds Off, What Allbirds Need to Do to Get Profitable, Why Growth has Slowed and The Bull Case for Allbirds Next Five Years with Joey Zwillinger, Co-Founder @ Allbirds
Joey Zwillinger is the Co-Founder & CEO @ Allbirds, the company behind the world's most comfortable shoe. In Nov 2021, Joey took the company public and the stock soared to an all-time high of $4BN, today the company has a market cap of $137M. Prior to Allbirds, Joey spent six years at biotechnology firm, Terravia, leading its renewable chemical business, developing and selling high-performance algae-based chemicals into various industries such as CPG, personal care, and industrials.
In Today's Episode with Joey Zwillinger We Discuss:
How did Joey's wife's friendship lead to the co-founding of Allbirds? What does Joey know now that he wishes he had known at the founding moment? What does Joey believe he is running away from? What is he running towards?
2. Public Market Performance Review:
Why has Allbirds lost 97% of it's value since going public? What mistakes were made? Why has revenue declined for the first time this year? What strategic investments have Allbirds pulled back on or paused entirely? When will Allbirds be profitable?
3. The Competition:
How do Allbirds compete and catch up with On and Hoka? What strategic mistakes did Allbirds make in COVID that allowed others to take the crown? Was the movement into running and athletics a mistake for Allbirds?
4. Joey Zwillinger: The Leader and Person:
Did Joey take secondaries out during the Allbirds journey? How does Joey reflect on his own relationship to money? How has Joey dealt with the last 12 months personally? How does he manage the stress effectively?
Mon, 06 Nov 2023 - 44min
1086 - 20VC Roundtable: Why Early Stage Founders Should Not be Investing, Why Great Founders Have Low EQ, How the Structure of VC Firms Will Change, Will Founder-Led Funds Compete with Sequoia & Is Investing a Team Sport?
Jack Altman is the Founder and CEO @ Lattice, the #1 people management platform, last valued at $3BN. Jack is an investor through his founding of Jack Altman Capital where he has invested in WorkOS, NexHealth, Owner.com, Mercury and more.
Auren Hoffman is the Founder and CEO @ Safegraph, the most accurate database of global points of interest, last valued at $550M. Auren is an investor through his founding of Flex Capital where he has invested in Chime, Checkr, Coinbase, Flexport, Vercel and more.
Jason Lemkin is the Founder and CEO @ SaaStr, the world's largest SaaS community. Jason is an investor through his founding of The SaaStr Fund. In the past, Jason has invested in Pipedrive, Algolia, Salesloft, Front, GreenHouse, Owner.com, Gorgias and more.
In Today's Episode on Founder-Led Funds We Discuss:
Fri, 03 Nov 2023 - 49min
1085 - 20Product: Why You Should Not Go Into Product Management, Why the CEO is Always the CPO, How to Build the Best Product Teams & Why You Should Hire People Who Aren't In Product Already with Databricks SVP Product, David Meyer
David Meyer is the SVP Products at Databricks where he drives product strategy and execution. He previously ran Engineering and Product Management at OneLogin, where he grew the company to thousands of customers and market leadership. Before OneLogin, he cofounded UniversityNow, an accredited open university system, running Product and Engineering. Prior to that, David managed a $1 billion portfolio of business intelligence products at SAP and co-led cloud strategy. His first software journey was at Plumtree which went public before being acquired by BEA in 2005.
In Today's Episode with David Meyer We Discuss:
How did David make his way into the world of product? Why did he not want to go into it? Why does David advise everyone "do not go into product management"? What does David know now that he wishes he had known when he entered product?
2. How to be a Great Product Leader:
Why does David think most leaders suck at leading? Why is the most important thing to make your team feel seen? What can leaders do to ensure this? Why does David help his team members to find other roles outside of the company?
3. Building the Best Product Team:
How does David hire for product today? What questions does he ask? What signals does he look for? What are David's biggest hiring mistakes? How did they change his approach? What are the biggest mistakes founders make when hiring for product? Why should you hire people who are not in product today?
4. David Meyer: The Art or Science of Product:
Is product more art or science? If David were to put a number on it, what would it be? Is simple always better when it comes to product? Will AI remove the importance and focus on UI? Why are the most impressive companies business model innovations not product innovations?
Wed, 01 Nov 2023 - 1h 02min
1084 - 20VC: Should Large Crypto Funds Give Money Back to LPs | What Will the Next Generation of Crypto Funds Look Like | What Should Happen with FTX; Who Should be Held to Account | The Future of NFTs & What Happens to Opensea w/ Nick Tomaino @ 1confirmation
Nick Tomaino is the Founder and General Partner @ 1confirmation, one of the leading seed firms fueling the decentralization of the web and society. The fund started with $26M in backing from individuals including Peter Thiel and Mark Cuban and it has been reported that the firm now has over $1B in assets under management. Nick has led seed investments in OpenSea, dYdX, SuperRare, Polkadot and Cosmos among others. Prior to 1confirmation, Nick was a Principal @ Runa Capital and before that led business development and marketing at Coinbase in the early days of the company.
In Today's Episode with Nick Tomaino We Discuss:
How did Nick first come into contact with crypto and bitcoin specifically? How did getting fired from Coinbase catalyse his move into venture? What does Nick know today that he wishes he had known when he started investing?
2. The Landscape Today: Funds and SBF
Are the current generation of crypto funds too large? Should they give money back to their LPs? Will the next generation of crypto funds be smaller? Are any crypto funds able to raise right now? Why does crypto Twitter hate crypto VCs? Who are the worst VCs for pump and dump?
3. SBF & FTX: What Actually Happened, Who is to Blame, What Happens from here?
What is the biggest misconception on SBF and FTX today? Who should be held accountable? What else would Nick like to see? How should FTX change the way that LPs invest into venture managers?
4. How to Build the Best Crypto Portfolio in Venture:
How large are the funds? How does Nick determine the right size for a fund? How many investments does Nick make per fund? How do loss rates look in crypto? What have been Nick's biggest investment hits and losses? How did that impact his mindset?
5. The Future for NFTs and Opensea:
Why does Nick remain bullish on the future of NFTs? How is Nick able to remain optimistic about the future of Opensea given their volumes? Where does Nick believe the fair price for Opensea should be today? Did Nick sell their Opensea at the $13Bn round?
Mon, 30 Oct 2023 - 55min
1083 - 20VC: The Three Types of Seed Round Today, Why Seed Has Never Been More Competitive, Why Pricing Has Never Been Higher, Why Boards at Pre-Seed Can Be Helpful & How Too Much Cash Too Soon Can Harm Companies with Ed Sim, Founder @ Boldstart
Ed Sim is one of the best seed round investors in venture as the Founder and Managing Partner @ Boldstart, Ed focuses specifically on developer, infra and SaaS at pre-seed and seed round. Over the last decade, Ed has backed some of the best including Snyk, BigID, Kustomer, Front and Superhuman.
In Today's Episode on Seed Rounds We Discuss:
What are the three different types of seed round today? Has seed ever been this competitive? Will seed be unimpacted by the macro decline we are seeing? Why are growth and multi-stage funds being more active than ever in seed?
2. Too Much Cash Will Kill You!
Why does Ed believe that too much capital can kill companies at the seed round? Why does Ed believe that the best founders are not always optimising for the highest price? What are the single biggest negatives of taking a high price at the seed round? What advice does Ed have for founders who have large offers from multi-stage funds at seed?
3. Is Growth Dead?
Why does Ed disagree and suggest that growth is not dead? What do multi-stage and growth funds now what to see that they did not before? How will the growth market evolve over the next 12-18 months?
4. IPOs, AI and M&A:
What will cause the IPO windows to crack open again? Why does Ed believe that many investing in AI are simply giving money to Nvidia? Does Ed agree that 95% of the cash going into AI from venture today will go to zero? Will we see more or less M&A in the next 12 months? How did Ed evaluate the Loom acquisition by Atlassian?
Fri, 27 Oct 2023 - 47min
1082 - 20Growth: Should Startups Hire Advisors? When is the Right Time? How Much Should They Be Paid? How Should Founders Approach the Hiring Process for Advisors? What Should They Expect From Them? What are the Biggest Mistakes Made and more with Ely Lerner
Ely Lerner is an EIR at Reforge and an advisor for startups transitioning from traction to hypergrowth. Previously he was Head of Consumer Product at Chime, and before that spent an incredible 8 years at Yelp in a number of different roles including Head of Product at Eat24, and Product Leader/GM at Yelp.
In Today's Episode with Ely Lerner We Discuss:
1. Entry into Growth:
How did Ely make his way from engineering manager to growth leader? What are a couple of his single biggest takeaways from his time with Yelp and Chime? Why do employees in large companies have to have P&L ownership when innovating within the larger company they are in?
2. Advisors: What, When and How:
What are the three different types of advisors founders can work with today? When is the right time to engage with each of them? Should the advisor have had direct experience with the problem you need help with? How should these advisors be compensated; what is normal? What are 1-2 of the biggest reasons startup advisory roles do not work out?
3. Offense vs Defence: The Tricky Balance:
What is the difference between offense and defense in product strategy? What should the resource allocation be between the two? What is the right amount of offensive strategies to have on at the same time? How can leaders prevent their defensive teams from feeling like second-class citizens?
4. Ely Lerner: AMA:
Why does Ely disagree with many and suggest that horizontal products do have a core ICP? Should growth teams sit on their own or within functions in the org? What are the core reasons teams fail to ship fast? What state should your data be in when you bring in your first growth hire?
Wed, 25 Oct 2023 - 51min
1081 - 20VC: Scaling to $50M ARR in 3 Years, Scaling to $20M ARR with Just $2M Invested; The Story of PhotoRoom, Is This YC's Most Capital Efficient Company with Matthieu Rouif, Co-Founder & CEO @ PhotoRoom
Matthieu Rouif is the Co-Founder and CEO @ PhotoRoom, one of the fastest-growing YC companies having scaled to an astonishing $50M in ARR in just 3 years. Their capital efficiency is immense having scaled to $20M in ARR on just $2M of invested capital. Prior to founding PhotoRoom, Matthieu founded several start-ups, including an app for ski resorts, HeyCrowd, and Replay, a video editor which was ultimately acquired by GoPro. Whilst at GoPro, Mattheiu led all image editing products.
In Today's Episode with Matthieu Rouif We Discuss:
How did Matthieu make the move from GoPro to founding PhotoRoom? What are the big mistakes Matthieu made on prior companies that he did differently with PhotoRoom? What does Matthieu know now that he wishes he had known when he started PhotoRoom?
2. Scaling to $20M in ARR with $2M of Cash:
What allowed Matthieu and PhotoRoom to be so capital-efficient in their scaling? What are the biggest mistakes founders make when it comes to resource allocation and capital efficiency? On reflection, what did Matthieu not spend money on that he wishes they had spent money on?
3. Consumer Subscription + Photo Editing: Is it a Good Business:
What are the customer acquisition costs by channel for PhotoRoom? What are their payback periods on a per-customer basis? How can it be a good business when the churn rate annually is 30-40%? How does this space play out with Canva, Adobe, Veed, Kapwing? Who wins?
4. The Future of AI:
Who wins; incumbents or startups? What matters more; data size or model size? Will UI be more or less important in an AI-first world? Why does Matthieu believe that everyone hates command line prompts? Will we see $BN revenue companies created with just 10 people?
Mon, 23 Oct 2023 - 43min
1080 - 20VC: NEW FORMAT: Harry Stebbings on Why Seed Pricing is as High as Ever, Why Series A is the Best Place to Invest Today, Why Growth Founders Need to Reshape Expectations, Why M&A Windows Remain Shut and When Will IPO Windows Crack Open
Harry Stebbings is the Founder of 20VC, building the next great financial institution at the intersection of media and venture capital. 20VC has reached over 125M downloads in 100+ countries and has featured the likes of Doug Leone, Bill Gurley, Marc Benioff, Daniel Ek and more. On the investing side, Harry has raised over $400M and made investments in the likes of Pachama, Linear, TripleDot, Superhuman, AgentSync, Linktree, Sorare and more.
In Today's Episode We Cover:
How has what LPs look for in new manager investments changed? What type of funds will be able to raise? Which will not be able to raise? What can managers do to significantly increase their chances of raising a new fund?
2. The Seed Investing Landscape: Harder Than Ever
Why is seed pricing as high as ever? Why are multi-stage funds more active in seed than ever? How does this impact seed? How will seed change and evolve over the next 6-12 months?
3. Series A + B: The Best Place to be Investing
Why is Series A the best risk/reward insertion point when investing today? How has the competition level at Series A and B changed? What do many people not see or know about this stage of the market today?
4. Is Growth Dead: Are Growth Deals Getting Done:
What two core elements are needed if you want to raise a growth round today? How have growth round valuations been impacted over the last 12 months? To what extent do founders need to change their expectations on the price of rounds they will be able to get done today?
5. M&A and IPOs: Tough Times Ahead
Why will we see continued low levels of activity in M&A markets? What acquisitions are we seeing take place? When will the IPO window crack open? Why were Klaviyo, Instacart and Arm not enough to open the windows?
Fri, 20 Oct 2023 - 27min
1079 - 20VC: Are LPs Open For Business? What Does it Take to Raise a Fund Today? How Has What LPs Want to See in Fund Investments Changed? Why Do LP Incentive Mechanisms Need to Change? Which Funds Will be Hit Hardest with Beezer Clarkson @ Sapphire Partners
Beezer Clarkson leads Sapphire Partners‘ investments in venture funds domestically and internationally. Beezer has invested in some of the best firms of a generation including USV and Point Nine to name a few. Beezer began her career in financial services over 20 years ago at Morgan Stanley in its global infrastructure group. Prior to joining Sapphire in 2012, Beezer managed the day-to-day operations of the Draper Fisher Jurvetson Global Network, which then had $7 billion under management across 16 venture funds worldwide.
In Today's Episode with Beezer Clarkson We Discuss:
Are LPs really all closed for business? What has changed in what LPs want to see from managers they are looking to invest in? What has changed about the size and pace of new commitments for LPs? Are all LPs moving away from growth?
2. 2020-2022: Years in Review:
Are LPs frustrated by managers who reduced deployment timelines to 12-18 months? Are LPs frustrated with managers who did not take liquidity when they could have done? How does Beezer advise managers on when and how to take liquidity in their best positions? Are managers accurately marking their portfolios to their LPs today? Why does Beezer believe the incentive mechanism for LPs is broken today in many ways?
3. How To Build a Top Decile Firm:
Why does Beezer believe if you want to have the best returns, you have to have one company that returns the fund? Can you not do it with multiple half-fund returners? Is ownership core to all the best firm's top performance? Is it the size of outcome or the size of ownership that drives the best performance across the board? What does data show on how the best funds take significant risk? What are their loss ratios? What are the core tradeoffs to Beezer between scaling AUM and providing top decile returns?
4. LP Markets: The Times They are a Changing:
Does Beezer believe LPs will remain cold on large $1BN+ growth firms? Which segments of the market are hot? Which are cold? What are the most significant changes we will see in the LP markets moving forward? Is today the new normal or are we in a downturn that we will come out of?
Wed, 18 Oct 2023 - 49min
1078 - 20VC: The Two Biggest Mistakes Every Founder Makes, Why Founders Are Not Ambitious Enough Today, Why Having a Narrow Target Customer is Dangerous & The Three Possible Outcomes in Company Building with Matthew Prince, Co-Founder @ Cloudflare
Matthew Prince is the co-founder and CEO of Cloudflare, on a mission is to help build a better Internet. Matthew has scaled Cloudflare to over $1BN in revenue, $20BN in market cap, and over 3,200 employees. Today the company runs one of the world's largest networks, which spans more than 200 cities in over 100 countries. Matthew is a World Economic Forum Technology Pioneer, a member of the Council on Foreign Relations, winner of the 2011 Tech Fellow Award, and serves on the Board of Advisors for the Center for Information Technology and Privacy Law.
In Today's Episode with Matthew Prince We Discuss:
1. From Selling Fireworks to Public Company CEO:
How did Matthew first make money selling fireworks as a kid? Does Mathew believe in the trope "you have to love what you do"? What does Matthew know now that he wishes he had known when he started Cloudflare?
2. Money, Identity and Happiness:
Why does Matthew feel many of the most successful founders lose their way when they leave their companies? How does he assess Gates, Bezos and others? Does Matthew tie his own identity to Cloudflare and the success of the company? How does Matthew evaluate his own relationship to money today? How has it changed over time? How does Matthew keep score today on how he is doing? What is success to Matthew?
3. The Three Outcomes for Companies Today:
What are the three outcomes available to companies today? What is the worst and why? What are the two biggest mistakes Matthew sees founders make today? Why does Matthew know that diverse teams are more successful? What is the proof? What is Matthew's single biggest advice to founders when it comes to selecting a co-founder?
4. Focus is BS: You Have to Have Mega Ambition:
Why does Matthew believe it is BS to have a very specific target customer from the offset? What does Matthew believe are the benefits of not having an ICP in the early days? What are the biggest pieces of VC advice to founders that Matthew knows to be wrong?
Mon, 16 Oct 2023 - 54min
1077 - 20VC: Israeli Resilience From Tech and Beyond with Michael Eisenberg and Adi Levanon
Michael Eisenberg spent 15 years as a General Partner @ Benchmark working alongside Bill and the Benchmark partnership. Following Benchmark, Michael co-founded Aleph, one of the leading Israeli venture funds of the last decade with a portfolio including Lemonade, Melio and HoneyBook, just to name a couple of Aleph’s unicorns.
Adi Levanon is the Founder & Managing Partner @ Selah Ventures, a solo-GP-founded venture fund investing $500k checks into AI-based solutions that enhance financial services, healthcare organizations, fintechs, and SMBs, with a focus on founders in the US and Israelis globally.
In Today's Episode on Israeli Resilience We Discuss:
Thu, 12 Oct 2023 - 44min
1076 - 20VC Roundtable: Are IPOs Back? Is Growth Dead? What Does it Take to Raise a Growth Round Today? How Do VCs Solve The Liquidity Challenge? Will We See a Massive Resetting of Valuations? AI Hype Growth Rounds?
Deven Parekh is a Managing Director at Insight Partners, one of the leading investing franchises of the last 25 years. Deven has made more than 90 investments since joining in 2000 including in the likes of Twitter, Alibaba, JD.com, Chargebee and Automattic (WordPress) to name a few.
Woody Marshall is a General Partner @ TCV, one of the most successful growth funds of the last decade with a portfolio including the likes of Facebook, AirBnB, Spotify, LinkedIn and many more incredible companies.
Jason Lemkin is the Founder @ SaaStr one of the best-performing early-stage venture funds focused on SaaS. In the past, Jason has led investments in Algolia, Pipedrive, Salesloft, TalkDesk, and RevenueCat to name a few.
In Today's Episode We Discuss:
1. The Growth Landscape Overview:
Is growth dead? Are any growth deals getting done? How has the price changed for growth deals that are getting done? Which type of growth companies will vs will not be able to raise? What happens to all of the growth companies with $300-$500M in cash but little revenue?
2. The Great Reset: Valuations Need to Change:
Why should companies be actively resetting their valuations? What are the benefits? What will happen between VCs and LPs when there is no incentive for VCs to reset their portfolio valuations when they need to go out and raise from those same LPs? Structure is often part of these valuation resets, is structure to rounds always bad? When is it good? What type of structure is acceptable vs unacceptable?
3. Are the Public Markets Creeping Open:
Should we take comfort from ARM, Instacart and Klaviyo and assume the public markets are going to open again? If not, what will cause them to open? How should we analyze the performance of the IPOs above? Many have been negative, are they right to suggest this is not the response we wanted? Why does Woody believe, like Instacart taking a 75% discount to their last round, we should have more and more companies go public at discounts to their last private round?
4. Late Stage Growth is Dead and Revenue Multiples:
Why is late-stage growth dead? How long do we think this will last? How should we assess revenue multiples today? New normal? Same as always? How will revenue multiples look in 12 months from now? How should we analyse the large late stage growth rounds for hyped AI companies? What happens there?
Wed, 11 Oct 2023 - 50min
1075 - 20VC: Atlassian Co-Founder Scott Farquhar on The Biggest Lessons Scaling Atlassian to $50BN Market Cap; The Four Roles of the CEO, The Funding Round That Net Accel $6BN, The Regrets of Omission and Commission & The Honeymoon Cut Short
Scott Farquhar is the Co-Founder & Co-CEO @ Atlassian. Scott co-founded the company with his university friend, Mike Cannon-Brookes, in 2002 from Australia. Over an incredible 20-year journey they have grown to a market cap of $50BN today, over 11,000 staff globally and serving over 260,000 customers. Scott is also a co-founder of Skip Capital, a private investment fund with a portfolio including Figma, Snyk, Canva and more.
In Today's Episode with Scott Farquhar We Discuss:
1. The 20-Year Journey to $50BN Market Cap:
How did Scott first make his way into the world of tech and come to co-found Atlassian? What does Scott know now that he wishes he had known at the beginning? From 20 years with Mike, what is Scott's biggest advice on choosing your co-founder?
2. The Fundraising Masterclass with Atlassian:
An emergency phone call, a honeymoon cut short; how did the first funding round for Atlassian come to be? Where was the business revenue-wise at the time? Why did Scott not like the traditional fundraising process? What did he do to add game theory and ensure that they got the best deal as a company? Why did Scott choose Accel with their offer? How did Peter Fenton lose a $3BN deal with Atlassian?
3. Lessons Scaling Atlassian to $4BN in Revenue:
What does Scott believe are the 4 core roles of the CEO? Is resource allocation the most important? What are the single biggest acts of commission and omission that Scott regrets? What are the biggest lessons Scott has from shutting down Stride, their Slack competitor?
4. Scott: The Father, Husband and Philanthropist:
What does great fatherhood mean to Scott today? What is the secret to a truly successful marriage? How does Scott assess his relationship to money today? How has it changed with time? How does Scott think about bringing children up in a world of affluence and abundance?
Fun Fact: Every single 20VC episode is recorded with Riverside.FM. It is the one product that I could not live without. Try it today here (https://creators.riverside.fm/20VC) and use the code 20VC for 15% off.
Mon, 09 Oct 2023 - 53min
1074 - 20VC: Why Great Companies are Defined by How Many Things They Say No To, Why Being First Does Not Matter & Why Market Over Traction or Team is the Most Important Thing with Guillermo Rauch, Founder & CEO @ Vercel
Guillermo Rauch is the Founder and CEO @ Vercel, giving developers the frameworks, workflows, and infrastructure to build a faster, more personalized Web. To date, Guillermo has raised $312M from Accel, Bedrock, Greenoaks, GV and more. Prior to founding Vercel, Guillermo co-founded LearnBoost and Cloudup where he served the company as CTO through its acquisition by Automattic in 2013.
In Today's Episode with Guillermo Rauch We Discuss:
1. From Argentina to SF: The Boy Making Money Online:
How did Guillermo first get into computers and start making money online? Does Guillermo still believe the US and SF offers the same opportunities it did when he came? Did Guillermo feel the weight of responsibility of providing for his family at a young age?
2. Timing, Markets and Narrative Violations:
Why does Guillermo believe it does not matter being first but being right? Why does Guillermo believe the most important thing for a company is market selection? Why does Guillermo believe it is crucial that founders and companies have "narrative violations"?
3. The Future of AI:
What model will win in the future; open or closed? Where does the value accrue; startups or incumbents? How will the SaaS business model change in a world of AI?
4. Silicon Valley's Most Successful Angel You Did Not Know:
What are some of Guillermo's biggest lessons from angel investing? What is his single biggest miss? How has it changed how he thinks? What have been his biggest hits? How did they impact how he thinks about what it takes to win?
Fri, 06 Oct 2023 - 58min
1073 - 20Sales: Why the Founder Should Not Be the One to Create the Sales Playbook, Why You Should Hire a Sales Leader Before Sales Reps & Why You Should Not Hire Sales Leaders From Big Companies with Matt Rosenberg, CRO @ Grammarly
Matt Rosenberg is Grammarly’s Chief Revenue Officer and Head of Grammarly Business. He leads all B2B revenue, operations, and growth for Grammarly Business, Grammarly for Education, and Grammarly for Developers. Previously, as CRO of Compass, he took the company into the Fortune 500 and contributed to a more than eightfold increase in business growth. Prior to Compass, Matt served as Eventbrite’s CRO leading them to become the largest event platform in the world by event count.
In Today's Episode with Matt Rosenberg We Discuss:
1. From Miserable Lawyer to World Beating Sales Leader:
How did Matt make the transition from lawyer to sales leader? What does Matt know now that he wishes he had known when he started in sales? What are Matt's biggest pieces of advice for anyone who wants to make a career change and is lacking confidence?
2. The Playbook and Hiring The Team:
How does Matt define the "sales playbook"? Should the founder be the one to create and execute V1 of the playbook? Should the first sales hire be a rep or a sales leader? When is the right time to make that all-important first sales hire?
3. Discounting, Champions and Urgency:
What can sales team do to create urgency in deal cycles? What works? What does not? How does Matt approach discounting? When to do it vs when not to? What level is acceptable? What are the biggest secrets to creating champions within prospects? Why does Matt believe that deals are won and lost in prospecting?
4. Developing Great Sales Talent:
How does Matt use sales call recordings to train teams? What is his 3x3 matrix for coaching calls? What is a good reason to lose a deal vs a bad reason? How does Matt do deal reviews? What are the single biggest elements sales leaders can do to nurture sales talent? What are the biggest mistakes sales leaders make when developing talent internally?
Wed, 04 Oct 2023 - 50min
1072 - 20VC: The Services Model of Venture Capital is Broken, The Best Founders Do Need Help, The Most Important Signals to Assess When Meeting Founders & Why Kids Bring Less Happiness and More Joy with Phin Barnes @ TheGP
Phin Barnes is the Co-founder and Managing Partner of The General Partnership (TheGP), a venture capital firm that’s redefining what partnership means for founders. Previously, Phin spent over a decade at First Round Capital, where he was responsible for over 60 investments including Blue Apron, Notion, Clover Health, Gauntlet and Persona. Before First Round, he created an independent video game company and before that was an early employee at AND 1 Basketball where he helped scale the brand from $15 to $225 million in revenue and served as the Creative Director for Footwear.
In Today's Episode with Phin Barnes We Discuss:
How did Phin make his way into the world of venture having been a Creative Director at a basketball brand? What does Phin know now that he wishes he could tell himself on his first day in venture? What are 1-2 of Phin's biggest lessons from his 10 years at First Round which shapes how he invests?
2. The Venture Capital Model is Broken:
Why does Phin believe the current services model of venture is broken? Do the best founders need your help? What have been some of the biggest lessons in what the best founders want from their VCs? What happens to this generation of firms with massive support teams? Do VCs use these support teams merely to justify massive fund size scaling to LPs?
3. The Venture Landscape Today:
How can we compete in a seed landscape of $5M on $25M against large multi-stage firms? What founders types are attracted to big brands? What founder profiles are taken in by large rounds and high prices? Is Phin more or less excited about seed-stage investing now than he has been before?
4. Investing Lessons 101:
What is Phin's biggest hit? How did seeing their success impact his mindset? What is Phin's biggest loss? How did the loss impact how he views investing? Traction, team, market; how does Phin rank the three in prioritisation? What should all young people know when entering the venture landscape?
Mon, 02 Oct 2023 - 1h 01min
1071 - 20Product: Why Product Memes Are More Important Than a Product Roadmap, Why Writing is the Essential Skill for Product People, How AI Changes The Role of Product, Big Mistakes Founders Make When Hiring Product Teams with Kevin Niparko, VP Product @ Twilio
Kevin Niparko is the VP of Product @ Twilio. Kevin joined Twilio through the acquisition of Segment where he spent an incredible 8 years in numerous different roles including as Head of Product. Before entering the world of product, Kevin was a Management Associate at the world-renowned, Bridgewater Associates.
In Today's Episode with Kevin Niparko We Discuss:
1. From Bridgewater to Head of Product:
How Kevin made his way from the world of asset management and analytics to leading product teams? What are 1-2 of Kevin's biggest takeaways from his time at Bridgewater with Ray Dalio? How did the 8 year journey with Segment leading to their $3BN acquisition impact his approach to product?
2. What Makes a Great Product Person:
Does Kevin believe that product is more art or science? If he were to put a number on it? What would it be out of 100? Why does Kevin believe that all product people should learn to write? Why does Kevin believe that the best product people are generalists and not specialists? Why does Kevin think that analytics is an insanely good start for product people?
3. How to Hire the Best Product People:
How does Kevin approach the hiring process for product hires today? What are the non-obvious traits of hires he looks for? How does he test for them? Does Kevin use case studies? Where do many fall down? What do the best do?
4. Product Reviews: Good vs Great:
How often does Kevin do product reviews? Who is invited? How have product reviews changed in a world where the company is now fully remote? What is the difference between good and great product reviews? What is the single best product decision Kevin has made? What did he learn? What is the worst product decision Kevin made? How did that change his approach?
Fri, 29 Sep 2023 - 46min
1070 - 20VC: "How Being a Founder Almost Killed Me"; We Have Lied to a Generation of Founders | The Hardest Truths About Being a Founder Revealed | Why AI Co-Pilot is BS, Seat Pricing is Over & User Interfaces are Stupid with Christian Lanng
Christian Lanng is the Founder and Former CEO @ Tradeshift, a company he took from garage to unicorn raising over $900M for with a latest price of $2.7BN in 2021. Just last month, Christian stepped away from the company and is now Chairman @ Beyond Work, building a better work experience through AI native software.
In Today's Episode with Christian Lanng We Discuss:
1. Burnout: When it Hits:
How did Christian know when something was really seriously wrong? What were the signs? How did being a founder literally almost kill Christian? How was that not a wakeup moment? How does being a founder make you so out of touch with reality?
2. The Things We Are Never Told:
Why does Christian think one of the biggest crimes is the myth that everyone can be a founder? What are the single biggest things about VCs that founders are not told? Why does Christian believe fundraising is absolutely a game? What are the rules to win it? What makes the best VCs? What makes the worst VCs? Why does Christian not like to take a discount for a brand name VC?
3. The Chaos That Happens Inside a Company:
Why does Christian believe politics should not be discussed within companies? What are Christian's biggest lessons on working with friends? Why after 14 years does Christian only have 3 friends that still talk to him? How did Christian fire 50% of his leadership team and productivity not change at all? Why does Christian believe US startups are inherently better than European ones?
4. Parenting and Relationship to Money:
Does Christian regret not being a present father for his child when building Tradeshift? What are the two options as a founder you have when bringing up kids? Was Christian scared to leave Tradeshift? How does he reflect on his relationship to money?
5. AI: Co-Pilot is BS, The Future Business Model and more...
Why does Christian believe co-pilot is the last dying breathe attempt from incumbents? Why does Christian believe that per-seat pricing will die? What will replace it? Why does Christian believe that AI will negate the importance of consumer-facing brands? In what way does Christian believe that UI is total BS? How does it change over time?
Wed, 27 Sep 2023 - 1h 09min