20VC: Softbank Managing Partner, Jeff Housenbold on How Softbank Approach Portfolio Construction, Their Optimal Investment Decision-Making Process and What Excites Softbank Most In Opportunities Today

20VC: Softbank Managing Partner, Jeff Housenbold on How Softbank Approach Portfolio Construction, Their Optimal Investment Decision-Making Process and What Excites Softbank Most In Opportunities Today

Jeff Housenbold is a Managing Partner @ Softbank Vision Fund, the leading and most influential firm in the venture space investing more than $93 billion in the businesses and technologies they believe will enable the next stage of the information revolution. To date, Jeff has backed the likes of OpenDoor, DoorDash, Wag, Clutter, Brandless and Katerra just to name a few. Prior to Softbank, Jeff spent 11 years as President and CEO @ Shutterfly, during his tenure the company enjoyed incredible growth with the growth of the team from 103 to 2,600 employees. In the past, Jeff has sat on the board of Caesers Entertainment (the world's largest casino entertainment company), Groupon and Chegg and is currently a member of the Board of Trustees of Carnegie Mellon University.

In Today's Episode You Will Learn:

1.) How Jeff made his way from being President and CEO of Shutterfly for 11 years to writing $200m-2Bn checks as Managing Partner @ Softbank Vision Fund?

2.) We have Wag on the small end and Uber on the high end, so how does Softbank think about portfolio construction and insertion point today? Blended, at what stage would Softbank like their capital to be most concentrated? Does Jeff believe that ownership is largely built on the first check or built over time?

3.) What does the internal investment-decision making process look like for Softbank? How does this decision-making process change when considering reserve allocation? How does Softbank think about and approach reserves given their later entry into companies? Given the size of check being written, what does diligence look like in the standard process for Softbank?

4.) Given the forthy pricing environment today, how does Jeff assess his own price sensitivity? Does this differ depending on the stage of entry? With many suggesting Softbank have extended the period of privatisation for companies, how does Jeff and the team think about liquidity? How does Jeff think about the future of secondaries for seed managers and angels?

5.) Question from Eric Wu @ Opendoor: How does Jeff think about and analyse the opportunity in fragmented categories? What is the bottoms up thought process to this thesis? Speaking of Opendoor, how does Jeff most like to work with the founders he backs? How does Jeff think about he allocates his time across the portfolio?

Items Mentioned In Today's Show:

Jeff's Fave Book: The Fountainhead

Jeff's Most Recent Investment: Katerra

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

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

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20VC: Benchmark Loses Another Partner | Elad Gil Raises a Monster $1.5BN Solo GP Fund | Why Apple Need a Management Overhaul | Why Google is the Best Performing Hyperscaler | Will Cursor Hit $4BN ARR & Lovable $400M ARR by EOY 2026?

20VC: Benchmark Loses Another Partner | Elad Gil Raises a Monster $1.5BN Solo GP Fund | Why Apple Need a Management Overhaul | Why Google is the Best Performing Hyperscaler | Will Cursor Hit $4BN ARR & Lovable $400M ARR by EOY 2026?

Agenda: 00:00 - Why Benchmark Is Bleeding Partners (and Why That's the New Normal) 04:57 - "I Wouldn't Leave Benchmark… Unless I Had THIS" — Jason on Brand vs Autonomy 09:01 - The Rise of the Solo GP & The Death of LP Conventional Wisdom 13:50 - The Unstoppable Force of Elad Gil & The Myth of LP Discipline 18:45 - Is Vibe Coding the New SaaS? Jason's $10K/Month Spend Reveal 26:57 - Cursor's Growth Is Insane—But Is It Sustainable? 31:44 - Will Microsoft, Google, or Amazon Win the AI Infra War? 37:42 - Is GitHub Copilot the Biggest Miss in Microsoft's History? 44:15 - Are Big Tech Incumbents Now Too Powerful to Fail? 48:00 - Apple's AI Problem: Is It Time for a Management Overhaul? 52:30 - Figma's IPO: $30B Return, Zero Hype. What Happened? 1:06:00 - Final Bets: Cursor to $4B ARR, Lovable to $400M ARR, OpenAI to $800BN?

31 Juli 1h 21min

20VC: a16z's Martin Casado on Anthropic vs OpenAI: Where Value Accrues | Cursor vs Replit vs Lovable: Who Wins and Who Loses | The One Sin in AI Investing | Why Open Source is a National Security Risk with China

20VC: a16z's Martin Casado on Anthropic vs OpenAI: Where Value Accrues | Cursor vs Replit vs Lovable: Who Wins and Who Loses | The One Sin in AI Investing | Why Open Source is a National Security Risk with China

Martin Casado is a General Partner @ a16z where he leads the firms $1.25BN infrastructure fund. At a16z, Martin has led investments in companies like Cursor, dbt Labs, and Fivetran to name a few. Before joining a16z, he co-founded Nicira, acquired by VMware for $1.26B. At VMware, he served as CTO of Networking. Widely regarded as a visionary in enterprise infrastructure, Martin has helped shape the modern cloud computing stack. Agenda: 00:00 – Analysis of Current AI Investment Landscape 04:45 – Will Anthropic Kill the AI App Layer? 09:20 – "The Oligopoly Is Coming—Just Like Cloud" 12:50 – Are AI Models Actually Terrible Venture Investments? 15:40 – Why it is BS to Put Down AI Apps for Having Temporary Revenue 21:30 – "Open Source Is a National Security Weapon—And We're Losing" 26:40 – "Have the Foundation Models of the Future All Been Founded Already" 34:30 – Why it is BS to Denigrate AI Apps for Having Low Margins 38:40 – Does AI Make 1x Engineers 10x or 10x Becomes 100x 44:10 – "We're All Dead Wrong About AI and Job Loss" 50:30 – "The Only Sin in Venture: Backing the Wrong Winner" 55:10 – What People Think They Know About Wealth But Do Not

28 Juli 1h 10min

20Product: Should We Kill the PM Role Entirely | How Does Product Design Change Most in a World of AI | How Do Monzo Build Product Today: What Works, What Does Not | Why Most Product Sucks and What Makes Truly Great Product

20Product: Should We Kill the PM Role Entirely | How Does Product Design Change Most in a World of AI | How Do Monzo Build Product Today: What Works, What Does Not | Why Most Product Sucks and What Makes Truly Great Product

Fernando Fanton is one of the most respected product leaders in Europe, having held Chief Product Officer roles at Monzo and Just Eat. He previously led product and tech at Rappi, one of Latin America's most valuable startups. Today, Fernando is the CPO @ Property Finder; one of the biggest breakout unicorns from MENA. Agenda: 00:00 – Is "having a vision" actually killing great product teams? 03:15 – Why do most products suck—and what separates the great ones? 07:20 – Should we kill the PM role entirely? Fernando says maybe. 11:45 – Is Monzo's obsession with trust more powerful than speed? 16:10 – What's the #1 reason internal tools will never replace SaaS? 21:00 – Will AI wipe out the need for designers and PMs? 26:30 – Is it arrogant for product teams to protect users from "bad" choices? 32:15 – What's the future of product when OpenAI controls the whole stack? 37:40 – What Monzo product blew up—and why no one saw it coming? 42:55 – Can a bank built on principles really become a $100B company?

27 Juli 1h 7min

20VC: Lovable Raises at $2BN & Hits $100M ARR | Is Cursor Worth $28BN at $1BN in ARR | How Do All Providers Deal with Anthropic Dependency Risk | Are Seed Funds F******: Have Mega Funds Won | Figma IPO Breakdown: Where Does it Price?

20VC: Lovable Raises at $2BN & Hits $100M ARR | Is Cursor Worth $28BN at $1BN in ARR | How Do All Providers Deal with Anthropic Dependency Risk | Are Seed Funds F******: Have Mega Funds Won | Figma IPO Breakdown: Where Does it Price?

Agenda: 00:00 – Did Jason Just Kill Replit? 03:45 – Why Claude Lies To You and Cannot Be Trusted 06:50 – You Cannot Trust Agents. Period. 10:20 – Why Windsurf Was Dead Without Claude 12:30 – Cursor vs. Lovable: What's the Better Bet? 14:40 – Should You Still Invest in Cursor at $28B? 18:05 – Would You Bet on Anthropic at $100B or OpenAI at $300B? 24:15 – Inside OpenAI's Secret Weapon: The Calvin French-Owen Memo 27:50 – Perplexity Just Crushed ChatGPT and Claude 32:15 – Will Cursor Build Their Own Models Before Anthropic Cuts Them Off? 33:20 – Figma's IPO at $16B: Outrageous or Fair Game? 41:55 – 90% of Seed Funds Are Cooked—Is Rob Go Right? 52:15 – How Often Do You Meet a Founder Who Can Return the Fund? 1:08:00 – Which Seed Fund Would You Back Today?

24 Juli 1h 21min

20VC: Scaling to $1BN+ in Revenue with No Funding: Surge AI | The Most Insane Scaling Story in Tech |

20VC: Scaling to $1BN+ in Revenue with No Funding: Surge AI | The Most Insane Scaling Story in Tech |

Edwin Chen is the Founder and CEO of Surge. Founded in 2020, Surge has scaled to $1BN+ in revenue with zero external funding. At the same time, their competitor, Scale.ai raised over $1.3BN to reach $850M ARR. Today, Surge have the world's largest model providers as customers and have just 120 employees. Agenda: 00:00 — "Everyone Else Is Just a Body Shop" — Edwin Calls Out the Whole Industry 01:05 — Why 90% of Big Tech Is Wasting Time on Useless Problems 03:45 — "I Don't Do 1-on-1s" — How Surge Kills Meetings and Still Moves 10x Faster 05:55 — Will a Single Person Build a $1B Company? 08:10 — 100x Engineers Are Real — Here's How to Spot Them 12:10 — Why Most PhDs Are Useless in AI Training 14:20 — Built to a Billion With Zero VC — Edwin Explains How and Why 17:00 — "No Sales Team, No PR, No BS" — Why Surge Stays in the Shadows 21:15 — The Real Reason AGI Might Take Until 2040 24:45 — Will Synthetic Data Kill Human Labelling? 29:00 — "Academic Benchmarks Are a Scam" 31:05 — Why the Real Bottleneck in AI Isn't Compute or Models — It's THIS 33:00 — What Every AI Company Should Be Asking (But Isn't) 35:15 — "No, I Wouldn't Sell Surge for $100B" 39:00 — Is the Application Layer Doomed? Edwin Predicts the Future of AI Startups 46:30 — Have the Leading Foundation Models Already Been Founded? 48:10 — AGI Could Be Dangerous — And Most People Are Ignoring Why 20VC: Scaling to $1BN+ in Revenue with No Funding: Surge AI | The Most Insane Scaling Story in Tech |

21 Juli 1h 6min

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 Juli 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 Juli 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 Juli 57min

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