20VC: Construct Your Fundraising Process To Get 3 Term Sheets in 36 Hours, Why Slow and Steady Can Be Best For Startups & Why All Startups Must Know Their Zero Cash Day with Nathan Wenzel, Founder & CEO @ SimpleLegal

20VC: Construct Your Fundraising Process To Get 3 Term Sheets in 36 Hours, Why Slow and Steady Can Be Best For Startups & Why All Startups Must Know Their Zero Cash Day with Nathan Wenzel, Founder & CEO @ SimpleLegal

Nathan Wenzel is the Founder & CEO @ SimpleLegal, the startup that helps legal operations reduce legal spend and improve operational efficiency. They recently raised their $10m Series A led by leading SaaS investors, Emergence Capital with participation from our favourites in the team at Susa Ventures and Rincon Venture Partners. As for Nathan, prior to founding SimpleLegal he spent time in consulting and as a Partner @ BI analytics firm, Edge Solutions.

In Today’s Episode You Will Learn:

1.) How Nathan made his way from consulting to BI analytics to founding one of SaaS's hottest "overnight successes" in SimpleLegal?

2.) Why does Nathan advocate for the slow and steady approach in startups? What type of business does this make sense for? Does this not go contra the traditional theory of move fast and break things?

3.) Nathan has said before that "most bay area millennials have not seen market corrections". How does Nathan's experience seeing these corrections affect his running of SimpleLegal? Why does Nathan think we have an impending market correction to come?

4.) Why must founders always know the day that they will become profitable? How does that change the way they operate and strategise the running of the business? Why is it also crucial for them to know their zero cash day?

5.) What did John really look for in his investors? What questions should founders ask potential investors pre-investment? How would John look to improve his fundraising process for the Series B?

Items Mentioned In Today’s Show:

Nathan’s Fave Book: Only The Paranoid Survive by Andy Grove

Nathan’s Fave Blog: SaaStr

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

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

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20VC: Cognition CEO Scott Wu on Acquiring Windsurf: The Process, The Deal, The Rationale | Did Google Overlook a Goldmine in the Core Asset and Did Founders Leave a Sinking Ship | How Cursor and Cognition Deal with Ever Increasing Reliance on Anthropic

20VC: Cognition CEO Scott Wu on Acquiring Windsurf: The Process, The Deal, The Rationale | Did Google Overlook a Goldmine in the Core Asset and Did Founders Leave a Sinking Ship | How Cursor and Cognition Deal with Ever Increasing Reliance on Anthropic

Scott Wu is the co-founder and CEO of Cognition, the company behind Devin, the world’s first AI software engineer. On Friday last week they pulled off the acquisition of the year, acquiring Windsurf, following their licensing agreement with Google. Previously a world-class competitive programmer, he was a gold medalist at the International Olympiad in Informatics and a member of the U.S. Math and Physics Olympiad teams. Before Cognition, he was a founding engineer at Scale AI, helping shape the early AI infrastructure stack. AGENDA: 00:00 – Why are founders walking away instead of going down with the ship? 01:05 – How did Cognition pull off the $220M Windsurf deal in just 72 hours? 04:45 – What really happened behind closed doors the weekend Windsurf was acquired? 07:15 – Did Google overlook a goldmine in the Windsurf team and IP? 09:00 – Who are the 100 people that secretly shape the future of AI? 12:30 – Can application startups ever gain leverage over foundation model giants like Anthropic? 14:15 – Is coding about to be replaced by simply describing what you want? 17:30 – 50% of new code is AI-written. Where does that go next? 20:45 – “We’ve gone from 0 to $80M ARR in 6 months. Quietly.” 25:00 – Are IDEs and agents just the training wheels for the real future of software engineering? 28:20 – If you could only back one—OpenAI or Anthropic—who’s the better bet? 30:00 – Why has Cognition kept its insane growth a secret… until now?

18 Jul 48min

20VC: Windsurf x Google x Cognition: Full Breakdown: Who Made Money, Who Did Not | Lovable vs Replit: Will These Be $100BN Businesses | Why Elon Could Beat Sam Altman with the New Grok | Why Every S&P 500 Company Will Buy Bitcoin?

20VC: Windsurf x Google x Cognition: Full Breakdown: Who Made Money, Who Did Not | Lovable vs Replit: Will These Be $100BN Businesses | Why Elon Could Beat Sam Altman with the New Grok | Why Every S&P 500 Company Will Buy Bitcoin?

Agenda: 00:00 Windsurf was dead—then this deal changed everything 05:00 The Windsurf x Google x Cognition saga explained 09:00 The OpenAI deal collapsed—what really happened 15:00 FTC rules forced a brutal deal structure—who lost? 17:00 The investors’ returns: who actually made money? 21:30 Will Google’s corp dev team get fired over this? 23:00 Cognition’s genius $220M acquisition of Windsurf: Most brilliant Deal of the Year 26:00 The biggest recruiting flex in Silicon Valley this year 35:00 “Roll your own SaaS” is complete nonsense 38:00 Lovable vs Cursor vs Replit: who wins the coding war? 41:00 Why Lovable could be the ChatGPT of builders 44:00 Will these vibe-coded apps become durable businesses? 48:00 The shocking churn rates hidden inside AI SaaS 55:00 Are these $2B valuations actually... cheap? 56:30 Grok just destroyed GPT-4 in benchmarks—WTF?! 01:01:00 Why Grok might overtake OpenAI in the next 12 months 01:11:00 Meta just invested $3.5B in Ray-Bans—WTF? 01:12:30 Should every S&P 500 company buy Bitcoin now? 01:15:00 Will Meta kill open source? What happens to Llama 5?

17 Jul 1h 21min

20VC: Vlad Tenev on Robinhood’s $85BN Resurgence | Tokenizing SpaceX & OpenAI | Building Nine Revenue Lines Over $100M | Why Crypto Will Be Robinhood's Biggest Revenue Line | Why Stablecoins Will Replace Banking Rails

20VC: Vlad Tenev on Robinhood’s $85BN Resurgence | Tokenizing SpaceX & OpenAI | Building Nine Revenue Lines Over $100M | Why Crypto Will Be Robinhood's Biggest Revenue Line | Why Stablecoins Will Replace Banking Rails

Vlad Tenev is the Founder and CEO of Robinhood, the greatest story on Wall St of the last decade. In the previous 18 months, Robinhood has increased its net revenue by 58% to nearly $3B; a $500M loss in 2023 turned into a $1.1B profit in 2024. Robinhood’s stock is up roughly 4x, lifting their market cap to north of $80B. Today, Robinhood has nine lines of business that do over $100M in revenue.  Agenda:  00:00 – “Tokenization Is The Biggest Innovation in Finance” 03:28 – How Robinhood 4x’d Its Market Cap in 8 Months 06:40 – AI Writes 50% of All Net New Code at Robinhood 10:02 – Why Robinhood Built a Secret ChatGPT for Support 12:11 – The One Customer Type That Transformed the Business 15:29 – “CoreWeave Is Retail’s Way Into AI” — The Meme Stock Defense 18:05 – Inside Robinhood’s Tokenized Private Shares Product 21:23 – “Capital as a Service” — Vlad’s Wild Vision for Startup Fundraising 24:10 – The $100M Revenue Line Vlad Wishes He Could Kill 26:45 – Robinhood Is Building... Cash Delivery Trucks?! 29:55 – “We Were Shipping Nothing”: Vlad on the 2020–2022 Culture Crisis 33:20 – What Line of Business Will Be the Biggest For Vlad in 5 Years Time 35:11 – The One Competitor Vlad Actually Respects 36:55 – From Men’s Health to Japanese Toilets: Vlad’s Weirdest Quickfire Yet 38:40 – “I Was in the Dumps”: What 2022 Taught Vlad About Resilience 40:00 – Where Robinhood Is Headed: The Next Decade of Financial Infrastructure

14 Jul 57min

20Growth: The Death of Growth Teams? | How Hubspot Use AI to Triple Email Conversion | The Future of AI SEO | Why Prompt Engineering is the New Coding | What Every CMO Needs to Know About AI in 2025

20Growth: The Death of Growth Teams? | How Hubspot Use AI to Triple Email Conversion | The Future of AI SEO | Why Prompt Engineering is the New Coding | What Every CMO Needs to Know About AI in 2025

Kieran Flanagan is the CMO at HubSpot, where he’s led the transformation of their growth strategy from SEO-led to multi-channel and AI-powered. Formerly SVP of Marketing, he helped scale HubSpot’s user base to millions and revenue past $2B. Before HubSpot, he drove breakout growth at Marketo and Salesforce. Kieran is one of the most respected voices in SaaS marketing and a pioneer in growth-driven content strategy. Agenda: 00:03 – The Death of Growth Teams? Kieran's Wild Prediction 06:44 – AI Innovation Pods: The New Org Structure for Startups 10:18 – Email Personalization That Tripled Conversions 13:21 – From Software Budget to Labor Budget: The Shift is Happening 16:35 – The Big Lie: Why Autonomous Agents Still Suck 19:24 – The Secret Sauce Behind HubSpot’s Email AI Stack 21:44 – Segment-Based Marketing Is Dead. Enter Micro Audiences. 24:15 – Content Collapse: Why Google Organic Is Getting Torched 30:52 – The Future of AI SEO: 1 Product, 100 Pages, Infinite Prompts 33:16 – Memory = Moat: Why ChatGPT Is Becoming Unbeatable 35:46 – Prompt Engineering is the New Coding: Here's How to Win 41:03 – The Death of the Middle Manager Marketer 46:17 – OpenAI vs. Anthropic: Kieran’s $400M Bet 48:00 – Europe Is Falling Behind: The Harsh Truth on Regulation 52:39 – CMO Playbook 2025: Micro-Audiences, Creator-Led, AI at Scale

11 Jul 1h 15min

20VC: Daniel Gross and Nat Friedman: Acquired by Meta | OpenAI’s SBC Bombshell: More Stock Comp Than Revenue | Privat Equity is Back: Olo Bought for $2BN | Microsoft Lays Off 9,000 People: Is This Just the Start | Will Sequoia Part with Shaun Maguire

20VC: Daniel Gross and Nat Friedman: Acquired by Meta | OpenAI’s SBC Bombshell: More Stock Comp Than Revenue | Privat Equity is Back: Olo Bought for $2BN | Microsoft Lays Off 9,000 People: Is This Just the Start | Will Sequoia Part with Shaun Maguire

Agenda: [00:00] The AI Talent Crisis No One’s Ready For [03:00] Daniel Gross and Nat Friedman: Why Two Legendary VCs Walked Away From $1B to Join Meta [12:00] Meta’s AI Talent Magnet: Will It Actually Work? [15:00] Cursor Is Breaking the Market: Can Anyone Compete? [18:30] OpenAI’s SBC Bombshell: More Stock Comp Than Revenue [22:00] CoreWeave’s Power Play: Buying Their Landlords [26:00] Is Circle Next to Go Shopping with Meme Equity? [28:00] PE Is Back: The Olo Take-Private Explained [35:00] Why Triple, Triple, Double, Double Is No Longer Sexy [41:00] QSBS Hack: The Billionaire’s Tax Loophole You’re Missing [48:00] Microsoft’s AI Layoffs: Salespeople Are Dead, Long Live Engineers [50:00] “If You Need a Week to Learn AI, You Should Be Fired” [53:00] Will Sequoia’s Sean Maguire Be Pushed Out? Place Your Bets [57:00] Will There Be a Recession in 2025? Jason Bets $75K It’s a No [1:00:00] Is Linda Yaccarino Still CEO of X by Year-End? [1:03:00] Circle and CoreWeave’s Meme Rally: Real or Mirage?

10 Jul 1h 7min

20VC: Scott Galloway on Are Billionaires Happy & The Impact of Money on Psychology and Self-Worth | Becoming a Better Father & Husband | Why We Should Drink More and Not Work From Home | The Tinder Effect & How it Makes Young Men Radical

20VC: Scott Galloway on Are Billionaires Happy & The Impact of Money on Psychology and Self-Worth | Becoming a Better Father & Husband | Why We Should Drink More and Not Work From Home | The Tinder Effect & How it Makes Young Men Radical

Scott Galloway is a Professor of Marketing at NYU Stern, where he’s taught for over two decades. He’s the founder of several successful companies, including L2 (acquired by Gartner for over $150M), Red Envelope, and Prophet. He’s a New York Times bestselling author of four books on business and tech, and co-hosts the award-winning Pivot podcast. Galloway also serves on the boards of The New York Times Company and Panera, and his public talks have been viewed tens of millions of times globally. In Today’s Episode We Discuss: 02:00 – How to Win in a New Economy of AI 06:00 – Should We Break Up Big Tech? 08:00 – Why Young People Have a Right to Be Angry? 11:00 – Why the Tax Code Is Rigged Against the Young 13:00 – Tax Changes That Would Make Young People Rich Again 17:00 – The Tinder Effect: Why Men Are Angry 20:00 – The Loneliness Epidemic in Men 23:00 – Remote Work & The Case for Alcohol 26:00 – Why Richer Families are Happier Families 30:00 – The Truth About Kids and Career 34:00 – Are Billionaires Happy? 38:00 – Becoming a Better Son, Father, Partner 46:00 – Behind the Persona: Who Scott Galloway Really Is

7 Jul 1h 10min

20VC: Figma's IPO: The Full Breakdown | Index Returns $3.5BN on Two Deals | Why Melio's $2.5BN Acquisition is "Discouraging" | Asana's New CEO and the Great Founder Exodus | Oracle's $30BN AI Deal and What it Means for Incumbents

20VC: Figma's IPO: The Full Breakdown | Index Returns $3.5BN on Two Deals | Why Melio's $2.5BN Acquisition is "Discouraging" | Asana's New CEO and the Great Founder Exodus | Oracle's $30BN AI Deal and What it Means for Incumbents

AGENDA: 00:00 – $400B in AI CapEx: Rational Investment or Madness? 05:00 – Figma's IPO: Rule of 80, $1.5B in cash, 40% margins. Unreal. 08:00 – Adobe Screwed the Deal—Should They Have Just Bought Canva? 16:00 – Pay-to-Play Deals: Heroic Hail Mary or Guaranteed Write-Off? 21:30 – How Index Is Returning $3.5B on 2 Deals 24:00 – Melio’s $2.5B Exit: Insane Growth… So Why Did They Sell?! 35:00 – Massive Penthouses and the Death of Focus: AI Founders Beware 39:00 – Chime, Anthropic, Menlo & The Art of Selling LPs the Future 41:00 – Couchbase Acquired: PE Buyers Are Back… Or Are They? 44:00 – Why No One’s Buying These 9-Figure SaaS Zombies 48:00 – If You Didn’t Grow from AI By June 30, You’re Already Dead 53:00 – Superhuman vs The AI-Natives: Who Wins the Replatforming War? 54:30 – Oracle's $30B AI Deal: Larry Did It Before You Even Started 56:00 – Scale Is Dead. Long Live Surge. The AI Data War Gets Bloody. 01:01:00 – Asana CEO Move & the Great Founder Exodus of 2025 01:06:00 – Will Cluely’s Founder Be a Billionaire by 2029? Place Your Bets

3 Jul 1h 11min

20VC: Inside KKR's Monster $8BN European Fund | The $500M Turkey Gamble That Went Wrong | Do Andreessen & General Catalyst Scare KKR? | Will AI Kill the PE Model? | Can The PE Model Survive without IPOs and Where is the Liquidity with Philip Freise

20VC: Inside KKR's Monster $8BN European Fund | The $500M Turkey Gamble That Went Wrong | Do Andreessen & General Catalyst Scare KKR? | Will AI Kill the PE Model? | Can The PE Model Survive without IPOs and Where is the Liquidity with Philip Freise

Philipp Freise is Co-Head of European Private Equity at KKR, where he manages the largest private fund in Europe with $8BN in the latest fund. Philip has led KKR's investments in FGS Global, Superstruct, Axel Springer SE, BMG Rights Management, Fotolia, GetYourGuide, GfK SE, Leonine, Mediawan SAS, Scout24 Switzerland and Trainline. Previously, Philip worked at McKinsey & Company in and co-founded Berlin-based VC firm Venturepark, Europe's first pan-European incubator. Agenda: 00:00 – "We Lost $500M in Turkey. Here’s Why We’ll Never Do It Again." 01:40 – Inside Europe’s Biggest PE Fund: $8B of Pure Firepower 03:55 – The $100M Dot-Com Failure That Changed My Career 06:45 – Why Picking the Wrong VC Will Destroy Your Company 10:20 – KKR’s $500M COVID Gamble: Genius or Insane? 12:35 – Why We Ignored the Market & Deployed 40% of Our Fund 15:55 – KKR’s Ruthless Portfolio Discipline: Love Doesn’t Matter 17:10 – Do Power Laws Apply in PE? Freise Destroys the Myth 18:45 – The Truth About Capital Intensity in the Age of AI 20:10 – Can AI Kill the PE Model? Here’s What Philipp Says 26:00 – The Secret to Great Investment Decisions at KKR 32:40 – Why There’s a $3T Liquidity Time Bomb in Venture 34:25 – The Death of IPOs? How KKR Exits Without Going Public 40:05 – Will KKR Europe Hit $20B? Freise's Bold Prediction 43:45 – Helsing, Space, and Defense: The New Age of DeepTech Bets 45:30 – Tariffs, China, and the Future of the German Car Empire 47:00 – Freise vs. Bitcoin: Will USD Still Rule in 10 Years? 48:15 – 4 Global Shocks Happening Right Now That You Need to Know 51:30 – KKR Missed Spotify AND Alibaba?! The Painful Stories 53:00 – Do Andreessen & General Catalyst Scare KKR? Freise Responds 54:30 – The One Metric That Will Define KKR’s Next Decade

30 Jun 1h 1min

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