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: a16z Raises $10BN in New Funds | Mercor Raises $350M at a $10BN Valuation | OpenAI Restructuring: Who Wins and Who Loses | Why IRR is a BS Metric and Three Ways to Win in VC Today

20VC: a16z Raises $10BN in New Funds | Mercor Raises $350M at a $10BN Valuation | OpenAI Restructuring: Who Wins and Who Loses | Why IRR is a BS Metric and Three Ways to Win in VC Today

AGENDA: 05:17 OpenAI's Restructuring: Winners and Losers 17:17 Andreessen Horowitz's Raise $10BN in New Funds 26:38 Mercor Raises $350M at a $10BN Valuation 43:08 Spray and Pray: Does it Work: Data Breakdown 47:04 The Role of Option Checks Venture Capital 48:36 The Three Ways to Win in VC Today 54:26 Why IRR is a BS Metric and What Matters More 01:08:47 Amazon's Struggles: How Do They Return to Greatness in AI

30 Loka 1h 24min

20VC: Sequoia's David Cahn on The Winners and Losers in AI | The $0-$100M Revenue Club: Is Triple, Triple, Double, Double Dead? | The Future of Defence: Who Wins and Who Loses | How to Analyse Margins and Growth Rates in a World of AI

20VC: Sequoia's David Cahn on The Winners and Losers in AI | The $0-$100M Revenue Club: Is Triple, Triple, Double, Double Dead? | The Future of Defence: Who Wins and Who Loses | How to Analyse Margins and Growth Rates in a World of AI

David Cahn is a Partner at Sequoia Capital and one of the world's leading AI investors. At Sequoia David has led investments in Clay, Juicebox, Sesame, Kela, Stark, etc.. Before Sequoia, David was a General Partner @ Coatue where he led investments in Notion and Hugging Face. AGENDA: 00:00 We Are in an AI Bubble 05:04 Why Building Physical Data Centres is a Moat 13:58 Winners and Losers in a World of AI 19:13 The Role of Big Tech and Monopolies 23:37 Breaking Down Circular Deals in AI: The Truth No One Sees? 38:19 Why Kingmaking is BS and VCs Do Not Make or Break Companies 41:30 The Importance of Margins in AI Investments 43:41 The Required Growth Rates in AI to Get Funded by Sequoia 45:30 The $0-$100M Revenue Club: Is Triple, Triple, Double, Double Dead? 51:53 Why the Most Important Hire for Startups Today is 23 Year Olds 01:01:19 The Future of Defence: Who Wins and Who Loses 01:10:15 Quickfire: Biggest Miss, Parenting Advice, Doug Leone Advice

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20Growth: How to Build a Paid Marketing Machine: ROAS (Return on Ad Spend) 101 | The Rise of User Generated Content and How to Use It | TikTok Ads: Expectations vs. Reality | Hiring for Growth: When and Who with Sandy Diao

Sandy Diao is one of the most exceptional growth leaders of the last decade. Sandy has scaled products to over 200M+ users and led growth teams at Descript, Meta and Pinterest. She is also a prolific writer all on things growth here.  AGENDA:  03:59 Biggest Growth Lessons from Pinterest 08:01 What is a Good vs a Bad Growth Hypothesis 11:11 Common Mistakes in Growth Strategies 14:57 Channel Fit: When You Have It & What To Do 25:43 Return on Ad Spend (ROAS) 101: How to Build a Paid Marketing Machine 30:08 How to Do SEO and Long-Term Growth Investments 33:22 Doubling Down on Successful Channels 36:31 The Unchanging Foundations of SEO 37:52 Generative AI Engines vs. Traditional Search Engines 41:12 Paid Marketing Channels: What's Overrated? 43:42 The Rise of User-Generated Content (UGC) 46:34 TikTok Ads: Expectations vs. Reality 49:55 Brand Marketing: What is Real vs What is BS? 53:33 The Importance of Feature Launches 01:01:50 Hiring for Growth: When and Who? 01:08:55 Quick Fire Round: Onboarding, Notifications, and Growth Channels

24 Loka 1h 16min

20VC: Why VC Today is Worse Than 2021 | Why Vertical SaaS is a Bad Investment Today | Why We Are Deluding Ourselves on Growth Expectations | Revolut Raises $3BN at a $75BN Valuation | Benchmark Adds Their Newest General Partner

20VC: Why VC Today is Worse Than 2021 | Why Vertical SaaS is a Bad Investment Today | Why We Are Deluding Ourselves on Growth Expectations | Revolut Raises $3BN at a $75BN Valuation | Benchmark Adds Their Newest General Partner

AGENDA: 04:50 Benchmark's New Partner: Everett Randall 10:19 Revolut Raises $3BN at a $75BN Valuation: Another Loss for Public Markets? 28:39 Why Today is as Bad as the Hype of COVID in 2021 32:10 Why Vertical SaaS is a Bad VC Investment Today 36:14 Why Everyone Investing in Legal SaaS Will Lose Money 44:16 Why King Making is More Real Than Ever 55:23 Why Your Smallest Customers Need to Pay $10K Minimum 01:01:37 Why VC is a S*** Asset Class 01:09:29 Why Today is Harder Than It Has Ever Been in VC 01:25:18 Closing Thoughts and Reflections

23 Loka 1h 28min

20VC: Deel CEO Alex Bouaziz on Raising $300M+ at a $17BN Valuation | Deel vs Rippling: WTF is Going On | Management Lessons from Ben Horowitz and Nik Storonsky | Deel's M&A Playbook: Lessons from 13 Acquisitions: What Works & What Doesn't

20VC: Deel CEO Alex Bouaziz on Raising $300M+ at a $17BN Valuation | Deel vs Rippling: WTF is Going On | Management Lessons from Ben Horowitz and Nik Storonsky | Deel's M&A Playbook: Lessons from 13 Acquisitions: What Works & What Doesn't

Alex Bouaziz is the Co-Founder and CEO @ Deel, the $17BN global payroll juggernaut that just last week announced their latest $300M fundraise led by Ribbit, a16z and Coatue. Deel has been on the most insane journey, they do $1BN+ in ARR, they just had their first $100M revenue month and they have been profitable for over 3 years. AGENDA: 03:38 Announcing $300M Fundraise at a $17BN Valuation 06:24 Rippling vs Deel: WTF is Going On? Where is the Lawsuit? 14:01 Why 1-1s Are BS and Leaders Should Stop Doing Them 17:31 Do Rich Leaders Make Better Leaders 28:33 Biggest Lesson from Ben Horowitz? Why Most CMOs Are Bad? 34:48 Lessons from Nik @ Revolut and Why Companies Need to Make Their Own Software 42:23 Deel's Acquisition Playbook: Lessons from 13 Acquisitions 45:17 How to Price Acquisitions? How to Align Incentives with Founders? 55:45 Deel is Profitable and Growing Fast: When is the IPO? 01:01:35 Best Acquisition Ever + Worst Ever: What Did We Learn?

22 Loka 1h 15min

20VC: The Startup Adding $1M ARR Every Week | Competing Against OpenAI's Codex and Claude Code: Who Wins | Why Gemini is Failing and GPT-5 Is Winning | Do Margins Matter in a World of AI | The Ugly Truth About AI Coding with Zach Lloyd, Warp

20VC: The Startup Adding $1M ARR Every Week | Competing Against OpenAI's Codex and Claude Code: Who Wins | Why Gemini is Failing and GPT-5 Is Winning | Do Margins Matter in a World of AI | The Ugly Truth About AI Coding with Zach Lloyd, Warp

Zach Lloyd is the Founder and CEO of Warp, the next-generation developer terminal reinventing how engineers build and collaborate. Warp has raised over $70M from top-tier investors including Sequoia Capital, GV, Dylan Field, and Elad Gil. Before founding Warp, Zach was Principal Engineer at Google, where he led development of Google Docs, and later served as CTO at Time. He's one of the most respected engineering minds redefining the future of developer tools. AGENDA: 04:14 Biggest Product Lessons from Rewriting Google Sheets 07:10 Why I Would Short Google: Leadership and AI Strategy 09:55 Comparing AI Models: GPT, Claude, and Gemini: Who Wins and Loses 17:04 Do Margins Matter in AI? 24:57 Adding $1M in ARR Every Week: Is Triple, Triple, Double, Double Dead? 33:58 How to Build Defensibility in a World of AI? 43:05 OpenAI vs Anthropic: Who Wins and Why? 44:25 Biggest Fundraising Lessons Raising from Sequoia, Elad Gil and GV 50:56 Why Sequoia are the Best VC 53:51 What Every Founder Gets Wrong in Fundraising 01:01:30 Quick Fire Questions and Final Thoughts

17 Loka 1h 13min

20VC: $3.5BN - The Price Zuck Paid for Thinking Machines Co-Founder | Goldman Sachs Acquires Industry Ventures for $665M | Softbank Borrows $5BN Against ARM Holding to Invest More Into OpenAI

20VC: $3.5BN - The Price Zuck Paid for Thinking Machines Co-Founder | Goldman Sachs Acquires Industry Ventures for $665M | Softbank Borrows $5BN Against ARM Holding to Invest More Into OpenAI

AGENDA: 03:44 Rory Is So Old He Worked with Arthur Rock!!! 07:28 Goldman Sachs Acquires Industry Ventures for $665M 16:37 Thinking Machines Co-Founder Raises $2BN and Then Leaves for Meta 29:36 SoftBank Goes for $5BN Leverage Against ARM Stock To Buy More OpenAI 39:35 More Data Centres Than Offices: Are We In a Bubble 43:28 Where is the Alpha in Venture in 2025 51:48 What 90% of Managers Get Wrong About Portfolio Management

16 Loka 1h 19min

20VC: Atlassian CEO on Why Everything is Overvalued & Are We in an AI Bubble | Do Margins Matter & Does Defensibility Exist in an AI World | Is Per Seat Pricing Dead & The Future of Vibe Coding with Mike Cannon-Brookes

20VC: Atlassian CEO on Why Everything is Overvalued & Are We in an AI Bubble | Do Margins Matter & Does Defensibility Exist in an AI World | Is Per Seat Pricing Dead & The Future of Vibe Coding with Mike Cannon-Brookes

Mike Cannon-Brookes is the Co-Founder and Co-CEO of Atlassian, the $50BN software giant behind products like Jira, Confluence, and Trello. Since founding the company in 2002, he has scaled it to over 300,000 customers globally, generating more than $5BN in annual revenue. Atlassian now employs over 10,000 people across 13 countries and is one of the most successful bootstrapped-to-IPO stories in tech history. Mike is also a leading climate investor and co-owner of several major sports teams. AGENDA: 00:00 Why Unreasonable Men Win in Startups 07:22 How to Make Co-CEOs Work 13:22 Are We in an AI Bubble? Is Everything Overvalued? 26:46 The Future of Software Development: More or Less Devs 32:53 Do Margins Matter in a World of AI 34:02 The Future of Vibe Coding… 36:35 Does Defensibility Exist in a World of AI 42:09 Is Per Seat Pricing Dead in a World of AI 49:01 The Founder Journey and Leadership 54:28 Quick Fire Round: Parenting Advice, Relationship to Money

13 Loka 1h 3min

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