20VC: The Core Lessons From Building a 150 Startup Angel Portfolio, Why Founders Who Angel Invest Have Such Strong Advantages and Why The Lean Startup Makes Less and Less Sense Today with Adrian Aoun, Founder & CEO @ Forward

20VC: The Core Lessons From Building a 150 Startup Angel Portfolio, Why Founders Who Angel Invest Have Such Strong Advantages and Why The Lean Startup Makes Less and Less Sense Today with Adrian Aoun, Founder & CEO @ Forward

Adrian Aoun is the Founder & CEO @ Forward, a health care system combining world-class doctors with advanced technology to empower patients to take control of their health. To date Adrian has raised funding from some of the true greats of the business including Marc Benioff, Eric Schmidt, Joe Lonsdale, Aaron Levie and Josh Kushner, to name a few. As a result of the incredible work at Forward, they were named to TIME's Best Inventions of 2017. Before Forward, Adrian was the head of special projects for the CEO of Google/Alphabet and Adrian arrived at Google following the acquisition of his artificial intelligence (AI) company, Wavii. Adrian is also a prolific angel with the likes of WorkRamp, Atrium, Convoy and more in his incredible portfolio.

In Today's Episode You Will Learn:

1.) How Adrian made his way from selling Wavii to running special projects for the CEO @ Google, to now changing the world of healthcare with Forward?

2.) Why does Adrian believe that ideas don't have to be inspiration based and you can follow a process to come to a startup idea? What is the framework for that process? What is it fundamental that one focuses on the problem not the solution? Post problem identification, what is the next step?

3.) Why does Adrian believe that today, the Lean Startup Methodology makes less and less sense? What leads Adrian to suggest that "regulation is not nearly as scary as people think? How does Adrian break regulation up into 3 different categories? How should investors assess and evaluate opportunities that do face regulation?

4.) What does Adrian believe are the core benefits he has received from investing in over 150 startups? What has Jason recognised with regards to the power law effect when investing? How does Adrian approach pro-rata? What has being on the other side of the table taught Adrian about good and bad actors in the world of VC?

5.) How can angels act as a check/balance on the behaviour of VCs? How does Adrian think about investor behavior in both the good and the bad times? How do the best in the business react in both situations?

Items Mentioned In Today's Show:

Adrian's Fave Book: Sapiens

As always you can follow Harry, The Twenty Minute VC and Adrian on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

We also speak about Movidiam – as brands turn to smarter ways of creating video and digital content, the Movidiam platform offers faster turnarounds whilst maintaining or improving quality. They're already working with some of the biggest, most innovative companies to help compare teams and freelancers across the global curated network of creative talent. Producers and marketers looking for the best creatives can get a shortlist from Movidiam's account managers in hours – tailored to their project's needs. Submit a brief or check out the platform at Movidiam.com.

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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

20VC: GPT5: Sam Altman's Masterplan or a Gift To Anthropic | Palantir & Shopify Crush Earnings | Monday & Datadog Perform But Hit Hard by Wall St | Should Perplexity Buy Chrome for $34.5BN |

20VC: GPT5: Sam Altman's Masterplan or a Gift To Anthropic | Palantir & Shopify Crush Earnings | Monday & Datadog Perform But Hit Hard by Wall St | Should Perplexity Buy Chrome for $34.5BN |

AGENDA: 00:04 – Was GPT-5 the Biggest AI Letdown Yet? 00:17 – Is OpenAI's Real Target Anthropic's $6B Revenue? 00:22 – Why Anthropic Might Secretly Be Worried 00:28 – The Hidden Business Strategy Behind OpenAI's "Underwhelming" Launch 00:32 – Should Perplexity Really Try to Buy Chrome for $34.5B? 00:35 – The $3B N8N Deal: Genius Bet or Bubble FOMO? 00:38 – Why Datadog's Best Quarter Ever Still Tanked the Stock 00:44 – Palantir's 50% Growth at Scale – Can It Last? Is Palantir Overpriced? 00:53 – Shopify's Ruthless Path to 91% Revenue Growth With 30% Fewer Staff 01:01 – Are Seed and Series A Valuations Now at Dangerous Highs? 01:06 – What Does The Highest Levels of Capital Concentration Mean For Early Stage Founders? 01:15 – Could Palantir Hit a $2 Trillion Market Cap by 2030?

14 Elo 1h 22min

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