20VC: First Round's Josh Kopelman on Why Price Is Both An Art and A Science, Why Ownership Must Be Built on First Check and The Negative Consequences of Attribution in Venture

20VC: First Round's Josh Kopelman on Why Price Is Both An Art and A Science, Why Ownership Must Be Built on First Check and The Negative Consequences of Attribution in Venture

Josh Kopelman is Founder & Partner @ First Round, one of the world's leading seed funds with a portfolio including the likes of Uber, Warby Parker, Flatiron Health, Square, HotelTonight, GOAT and more incredible companies. As for Josh, he founded First Round in 2004 to reinvent seed stage investing. Since he has invested in over 200 startups and been ranked 4th in Forbes Midas List and named one of the top ten 'angel investors' in the US by Newsweek magazine. Josh has previously sat on the boards of Flatiron Health, Clover Health, AppNexus and more.

In Today's Episode You Will Learn:

1.) How Josh made his way into the wonderful world of venture from angel investing and what the inspiration behind the founding of First Round was?

2.) How does Josh think about price sensitivity today? What were his learnings from being priced out of the seed round for Twitter and Dropbox? How has Josh seen his relationship to price change over time? How did witnessing the boom and bust both as operator and investor affect his investing mentality today?

3.) How does Josh and First Round think about reserve allocation? How has their thinking changed and evolved over time? Does Josh believe that ownership is fundamentally built on first check? What does the investment decision-making process look like for reserves? In terms of allocation, how does Josh think about time allocation across portfolio? Spend it with the winners, they return the fund or the strugglers and save cents on the dollar?

4.) Josh has spent over 3,000 hours on boards, what have been some of the biggest inflection points that have changed the way he thinks about being a good board member? How has he seen his style and approach change over time? What advice would Josh give to an individual that has just gained their first institutional board seat?

5.) Why does Josh believe that we fundamentally neglect "the pick" today in startup world? Why does Josh believe a high degree of startup mortality begins at the pick (idea) stage? How do the very best founders aproach this stage? How should these founders approach picking their investors? What should they look for? What should they be wary of?

6.) Why does Josh want to be known as a better picker of partners than investments? How has Josh thought about the building ou of the first round partnership over time? If there was anything he would have done differently, what would it be? Why does Josh fundamentally disagree with attribution? How does Josh think about generational transition? What are the steps required to do it well?

Items Mentioned In Today's Show:

Josh's Fave Book: Thinking in Bets: Making Smarter Decisions When You Don't Have All the Facts

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20Growth: Meta CMO Alex Schultz on How All Founders Have to Change Their Marketing Playbook in a World of AI | Is AI Plateauing, What it Means if China Wins the AI Race and Why Zuck is a Generational Leader

20Growth: Meta CMO Alex Schultz on How All Founders Have to Change Their Marketing Playbook in a World of AI | Is AI Plateauing, What it Means if China Wins the AI Race and Why Zuck is a Generational Leader

Alex Schultz is the Chief Marketing Officer and VP of Analytics at Meta, where he has spent nearly two decades shaping the company's growth and marketing strategy. He has been instrumental in scaling Facebook, Instagram, and WhatsApp to billions of users worldwide. Alex is is also the author of Click Here: The New Rules of Marketing, the definitive guide to modern growth — available now on Amazon. AGENDA: 00:00 – Is All Marketing Actually Performance Marketing? 04:00 – When Did Facebook Have the Wrong North Star? What Did They Learn? 16:00 – Will AI Create Companies Run by Just ONE Person? 27:00 – Is AI About to Hit the Biggest Plateau Since Self-Driving Cars? 30:00 – Is China Secretly Winning the Global AI Arms Race? 38:00 – Does AI Kill Content or Supercharge It? 44:00 – Why Brand Marketing Is Harder (and More Important) Than You Think 47:00 – Will Glasses Replace Phones Forever? 51:00 – What Would Alex Do If He Were Sundar at Google Today? 59:00 – What is the Greatest Strength and the Greatest Weakness of Zuck?

5 Sep 1h 10min

20VC: Anthropic Raises $13BN | Why Canva Will Not Direct List | OpenAI Buys Statsig for $1.1BN All Stock | Lovable Raising at $4BN + Vercel at $9BN: Justified or Not | Quarterly Results from SNOW, Mongo, ZOOM and more

20VC: Anthropic Raises $13BN | Why Canva Will Not Direct List | OpenAI Buys Statsig for $1.1BN All Stock | Lovable Raising at $4BN + Vercel at $9BN: Justified or Not | Quarterly Results from SNOW, Mongo, ZOOM and more

Agenda: 04:00 – Anthropic Raises $13BN: The Analysis? 19:00 – Is Zuck's $14BN Scale bet the biggest blunder in AI? 27:00 – Lovable Raising at $4BN and Vercel at $9BN: Justified or Madness? 36:00 – Quarterly Results for Snowflake, Mongo, Okta, Zoom Skyrocket: Is B2B SaaS back from the dead? 48:00 – Is Jensen Huang right there will be $4TRN in AI gains? 57:00 – Will AI wipe out SaaS margins with 10% GPU taxes? Or is Notion the exception? Items Mentioned in Today's Episode: Try NEXOS.AI for yourself with a 14-day free trial: https://nexos.ai/20vc

4 Sep 1h 14min

20VC: Cohere Founder on How Cohere Compete with OpenAI and Anthropic $BNs | Why Counties Should Fund Their Own Models & the Need for Model Sovereignty | How Sam Altman Has Done a Disservice to AI with Nick Frosst

20VC: Cohere Founder on How Cohere Compete with OpenAI and Anthropic $BNs | Why Counties Should Fund Their Own Models & the Need for Model Sovereignty | How Sam Altman Has Done a Disservice to AI with Nick Frosst

Nick Frosst is a Canadian AI researcher and entrepreneur, best known as co-founder of Cohere, the enterprise-focused LLM. Cohere has raised over $900 million, most recently a $500 million round, bringing its valuation to $6.8 billion. Under his leadership, Cohere hit $100M in ARR. Prior to founding Cohere, Nick was a researcher at Google Brain and a protégé of Geoffrey Hinton. AGENDA: 00:00 – Biggest lessons from Geoff Hinton at Google Brain? 02:10 – Did Google completely sleep at the wheel and miss ChatGPT? 05:45 – Is data or compute the real bottleneck in AI's future? 07:20 – Does GPT5 Prove That Scaling Laws are BS? 13:30 – Are AI benchmarks just total BS? 17:00 – Would Cohere spend $5M on a single AI researcher? 19:40 – What is nonsense in AI that everyone is talking about? 25:30 – What is no one talking about in AI that everyone should be talking about? 33:00 – How do Cohere compete with OpenAI and Anthropic's billions? 44:30 – Why does being American actually hurt tech companies today? 45:10 – Should countries fund their own models? Is model sovereignty the future? 52:00 – Why has Sam Altman actually done a disservice to AI?

1 Sep 1h 7min

20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi

20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi

Jason James is the Co-Founder of Tezi and one of the leading product minds in the valley. Prior to Tezi, Jason was the VP Product at Instacart and before that was Head of Product and Design at Thumbtack. AGENDA: 00:00 Product lessons scaling Instacart to $40B – what really moves the needle 02:15 Why "quick optimizations" won't build billion-dollar products 04:30 MVPs are dead? How AI is reshaping product development 07:00 Do startups even need PMs anymore in the age of AI? 11:30 The biggest product mistake Jason made building Tezi 16:30 Why most hiring managers fail at recruiting 20:00 The resume trap: how to spot if someone was just "on the elevator up" 26:00 The three roles founders always end up firing 28:00 Are most CPOs actually terrible? 36:30 The myth of startup "culture" – why growth is the only thing that matters 43:00 Did DoorDash actually beat Instacart? The inside take 48:00 Fundraising secrets founders never realize until it's too late

29 Aug 53min

20VC: Anthropic's $10BN Round | Klarna's IPO Broken Down | Inside a16z's 72 Deal Seed Investment Machine | Martin Casado: Is Consensus Investing the Only Game | Why Satya is Chatting S*** on SaaS Apps Disappearing featuring Marc Benioff

20VC: Anthropic's $10BN Round | Klarna's IPO Broken Down | Inside a16z's 72 Deal Seed Investment Machine | Martin Casado: Is Consensus Investing the Only Game | Why Satya is Chatting S*** on SaaS Apps Disappearing featuring Marc Benioff

AGENDA: ​​00:00 – Marc Benioff vs Snowflake, Databricks & Palantir: Who Wins the Data Cloud War? 05:10 – Does Benioff Feel The Need to Buy AI Talent Like Zuck Is? 09:00 – What Salesforce has Learned From Palantir on Forward Deployed Engineers? 18:00 – Will SaaS apps disappear in an AI world? Why Satya is Chatting S*** 23:40 – Are SDRs really screwed by AI… or just evolving? 26:10 – Benioff on Who Wins: OpenAI or Anthropic? 30:00 – Nat Friedman reports to Alex Wang: Genius move or career downgrade? 34:00 – Anthropic's $10B round: Have we hit peak AI hype? 47:00 – Klarna's wild ride: From $45B to $6B to IPO at $15B 55:00 – Inside a16z's seed machine: 72 bets vs Sequoia's 27 57:45 – Martìn Casado: Is consensus investing dangerous—or the only game? 01:05:00 – The big lesson: consensus, contrarian, and why investing is harder than ever

28 Aug 1h 11min

20VC: Do Margins Matter in AI? | Is Defensibility Gone For Good? | Is Vertical SaaS Dead in a World of AI | What SaaS Rules Are BS and No Longer Apply in a World of AI | The Future of Venture: Why Chanel vs Walmart is BS with Byron Deeter

20VC: Do Margins Matter in AI? | Is Defensibility Gone For Good? | Is Vertical SaaS Dead in a World of AI | What SaaS Rules Are BS and No Longer Apply in a World of AI | The Future of Venture: Why Chanel vs Walmart is BS with Byron Deeter

Byron Deeter is a Partner at Bessemer Venture Partners, and one of the most renowned SaaS investors. Byron has led 19 unicorn investments, including IPO successes like ServiceTitan, Procore, Twilio, Box, Gainsight, Intercom, DocuSign, SendGrid. His portfolio includes eight companies that have gone public. Insane. Agenda: 00:00 – Why are the stakes in AI higher than ever before? 05:20 – Is defensibility in AI gone for good? 07:40 – Do margins even matter when backing the next Anthropic or Perplexity? 09:50 – How does Byron think about future dilution when investing in AI today? 12:10 – With 40% of venture money going to 10 deals, is there any point investing elsewhere? 13:40 – Is vertical SaaS dead? Is there any point when the large players can own it? 18:00 – Will AI shift from the tech budget to the human labor budget and unlock trillions? 21:10 – Are we entering the era of billion-dollar businesses built by 10 people? 25:20 – Is treble-treble-double-double now too slow for AI companies? 33:10 – In today's AI gold rush, is it better to scream the loudest or just build the best product? 41:10 – What specific growth rates are best in class, good and not good enough today? 55:00 – Is venture now just a game of scale — Chanel vs. Walmart?

25 Aug 1h 21min

20VC: Databricks at $100BN | Chamath's SPAC Revival: Peak Mania? | OpenAI Staff Cash Out Billions & Sam Altman Will Spend Trillions | CoreWeave's $11B Debt Bet & Nubank's $2.5B Profit Shocker

20VC: Databricks at $100BN | Chamath's SPAC Revival: Peak Mania? | OpenAI Staff Cash Out Billions & Sam Altman Will Spend Trillions | CoreWeave's $11B Debt Bet & Nubank's $2.5B Profit Shocker

Agenda: 00:00 – Databricks hits $100B: Bubble or just the beginning? 03:15 – Is Databricks actually undervalued at 25x revenue? 07:40 – Are we on the verge of the biggest IPO wave ever? 11:30 – Can Andreessen's Databricks bet return $30B+? 18:10 – Who really gets rich when mega-unicorns IPO? 19:30 – Is the return of Chamath's SPACs the ultimate bubble signal? 28:00 – Should OpenAI staff be cashing out billions in secondaries? 33:30 – Founder raises $130M… then walks away. Is this the new normal? 36:30 – Nubank's $2.5B profit: The best FinTech in the world? 48:00 – On Running at $15B: Can consumer brands still be VC-backed rockets? 52:00 – CoreWeave takes on $11B in debt: smart bet or ticking time bomb? 1:11:00 – Will AI spend really hit trillions—or is it all hype?

21 Aug 1h 27min

20VC: Lovable CEO Anton Osika on $120M in ARR in 7 Months | The Honest Truth About Defensibility and Unit Economics for AI Startups | The State of Foundation Models: Long Grok, Short OpenAI, Why | Replit vs Lovable vs Bolt: What Happens

20VC: Lovable CEO Anton Osika on $120M in ARR in 7 Months | The Honest Truth About Defensibility and Unit Economics for AI Startups | The State of Foundation Models: Long Grok, Short OpenAI, Why | Replit vs Lovable vs Bolt: What Happens

Anton Osika is the Co-Founder and CEO @ Lovable, the fastest growing company on the planet. In just 7 months, they have scaled from $0 to $120M in ARR. They have raised over $200M in funding from some of the best including Accel, Creandum and 20VC. Their latest round priced the company at a whopping $2BN. Agenda for Today: 00:00 – Is AI an Arms Race… Or Just a Talent War? 03:45 – How Does Anton Compete with Zuck's $100M Packages for Talent 07:30 – Founder Mode vs. Structure: Can Chaos Scale? 10:15 – The Brutal Truth About Defensibility in AI Startups 13:20 – Unit Economics: Are AI Companies Doomed to Bleed Cash? 17:00 – GPT-5: Game-Changer or Overhyped Disappointment? 20:10 – How Lovable Hit $100M ARR in Just 7 Months? 25:15 – Replit, Figma, Bolt: Which Competitor is the Best? 30:00 – The Security Bombshells No One Talks About 36:40 – Should Anyone Still Study Computer Science? 40:30 – Work-Life Balance Is Dead: Inside Anton's 10x Culture 56:00 – OpenAI, Anthropic, or Grok: Who Wins the AI Wars?

18 Aug 1h 8min

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