Uber's First Investor, First Round Capital's Rob Hayes on How The Deal Of The Decade Originated and Why Product Orientated VC Is The Future

Uber's First Investor, First Round Capital's Rob Hayes on How The Deal Of The Decade Originated and Why Product Orientated VC Is The Future

Rob Hayes is a partner at First Round Capital where he opened up the firm's San Francisco office. Over the past eight years, he has led investments in companies such as Mint.com (acquired by Intuit), Gnip (acquired by Twitter), Square, Uber, eero, and Planet Labs. Prior to joining First Round, Rob became the first venture investor at Omidyar Network, the investment firm started by eBay founder Pierre Omidyar. While there, he led most of the initial venture capital deals and later built and ran the technology investing group. Before that, Rob worked at Palm, where he product managed Palm OS and started the company's corporate venture fund.

In Today's Episode You Will Learn:

1.) How Rob made his move into the VC world from working with Palm in the heyday?

2.) Question From David Hornik : How did Rob's seed investment in Uber originate? What made Rob invest? Did Rob realise the potential for Uber when he invested? When did Rob realize it was going to be huge?

3.) Has the investment in Uber changed how Rob views seed investing? Talking of the Uber’s of the world, how do you ensure that you find and decide to invest in the next Uber, when it raises a seed round?

4.) In terms of deal closing, how does Rob approach that element of the deal and what was the competition and closing environment around the Uber deal?

5.) Question from Satya at Homebrew: Stepping back and looking at First Round, what has changed in FRC’s approach as the firm has grown? How does the firm think about managing generational transition?

Items Mentioned In Today's Episode:

Rob's Fave Book:

Rob's Fave Blog or Newsletter:

Rob's Most Recent Investment:

As always you can follow The Twenty Minute VC, Harry and Rob on Twitter here! If you would like to see a more colourful side to Harry with many a mojito session, you can follow him on Instagram here! How many emails do you have in your inbox right now? A hundred? A thousand? The answer is too many. But here’s the thing—even though I knew I wanted to do something about it, I didn’t know how. It’s called SaneBox. SaneBox sorts through your email and moves all of the trivial stuff into a different folder so the only messages in your inbox are the ones you actually want to see. Visit sanebox.com/20VC today and they’ll throw in an extra $20 credit on top of the two-week free trial.

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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 Syys 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 Syys 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 Elo 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 Elo 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 Elo 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 Elo 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 Elo 1h 8min

20VC: 15 Term Sheets in 7 Days and Choosing Benchmark | Harvey vs Legora: Who Wins Legal and How to Play When You Have $600M Less Funding | Are AI Models Plateauing Today | Building a 9-9-6 Culture From Stockholm with Max Junestrand

20VC: 15 Term Sheets in 7 Days and Choosing Benchmark | Harvey vs Legora: Who Wins Legal and How to Play When You Have $600M Less Funding | Are AI Models Plateauing Today | Building a 9-9-6 Culture From Stockholm with Max Junestrand

Max Junestrand is the Co-Founder and CEO @ Legora, the collaborative AI powering the next generation of lawyers. Now this is an insane story for many reasons; first, Max turned down a multi-million dollar career in gaming to build Legora. Second, he has raised from the best of the best including Benchmark and IVP. Third, he has scaled the firm with 1/6th of the capital of his closest competitor, Harvey have raised a reported $800M while Legora have raised just $120M. Agenda: 00:03 – From Pro Gamer to AI Founder: How World of Warcraft Shaped Max's Mindset 04:58 – The $5–10M Gaming Career He Walked Away From 07:55 – Are AI Models Plateauing… or Just Getting Started? 10:02 – Swarms of LLMs: The 100x Cost Bet That Could Change Legal Forever 12:00 – Partnering With the Lawyers You're "Killing" 15:00 – How He Cracked Sweden's Hardest-to-Enter Law Firm 21:45 – The $500K Coffee That Saved the Company at YC 30:00 – Closing 15 Term Sheets in 7 Days – Why Benchmark Won 36:00 – Beating a $5BN Rival With a Fraction of the Funding 53:50 – Building a Cult Culture: The 9-9-6 Mentality in Europe

15 Elo 1h 20min

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