20VC: The Opendoor Memo: Keith Rabois on The Origins of Opendoor from a Conversation with Peter Thiel, Why Cash is Not a Competitive Moat for Startups Today and What People Misunderstand About Black Swan Events in Real Estate and How it Impacts Opendoor
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Release Date: 09/30/2021
20VC: Inside Bending Spoons Acquisition Machine: Evernote, Eventbrite, Vimeo | How Evernote Evaluates Acquisitions and New Product Ideas | How Evernote Mastered Product Launches, User Retention and Monetisation with Federico Simionato
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Bending Spoons is the acquisition machine of the tech world. They have acquired the likes of Evernote, Vimeo, Eventbrite, Streamyard and more. However, they never open their gates to the secrets behind Evernote’s product machine. Today that changes with Federico Simionato joining 20Product. Fede has been a Product Lead at Bending Spoons for 8 years where he has led product teams at Evernote, WeTransfer and more. AGENDA: 03:02 From Dentist Games to $11BN Bending Spoons 04:54 Advice for Aspiring Product Managers 05:38 Building a Coveted Brand at Bending Spoons 07:43 Evaluating and...
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20VC: Thrive & OpenAI Partnership | Eventbrite Acquired for $500M | Databricks Raising $5BN at $134BN Valuation: Cheap or Not? | Why SaaS is Like Japan and The TAM Trap in Software
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
AGENDA: 04:20 Thrive and OpenAI Partnership 07:14 Databricks Raising $5BN at $134BN Valuation: Cheap or Not? 17:39 Eventbrite Acquired by Bending Spoons for $500M 21:39 Pagerduty’s $1BN Market Cap, Just 2x Revenue 26:59 The TAM Trap: Why SaaS Is Like Japan 37:42 Lessons from Companies Hitting $100M ARR 44:57 The Future of Labour Markets is F****** 52:10 The Importance of Compounding in Investments 56:45 The Relevance Game in Venture Capital 01:05:01 Supabase at $5BN or Lovable at $6BN: Which One?
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20VC: Scale, Surge, Turing, Mercor: Who Wins & Who Loses in Data Labelling | Is Revenue in Data Labelling Real or GMV? | Why 99% of Knowledge Work Will Go and What Happens Then? | Why SaaS is Dead in a World of AI with Jonathan Siddharth @ Turing
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Jonathan Siddharth is Founder and CEO of Turing, one of the fastest-growing AI companies advancing frontier models. Jonathan has led the company to an astonishing $300M ARR with just $225M raised and a profitable company. A Stanford-trained AI scientist, Jonathan previously helped pioneer natural language search at Powerset, which was acquired by Microsoft. AGENDA: 03:35 Data, Compute, Algorithms: What is Most Abundant? What is Lacking Most? 09:18 What Does No One Know About AI’s Data Requirements That Everyone Should? 17:05 The Biggest Challenges Enterprises Have with AI Adoption 20:38 Why...
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20Sales: John McMahon on How to Hire, Train & Retain the Best Sales Reps | How Sales Changes in a World of AI | Sales Lessons from Snowflake and MongoDB | How to Create and Drive a Sales Process with Urgency
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
John McMahon is widely regarded as one of the greatest enterprise-software sales leaders of all time. He’s the only person to have served as Chief Revenue Officer at five public software companies: PTC, GeoTel, Ariba, BladeLogic and BMC Software. He helped scale BladeLogic from a startup into a public company — ultimately leading to its ~$880M sale to BMC — and drove GeoTel into a multi-billion dollar acquisition. Today he sits on the boards of top names such as Snowflake and MongoDB, while also mentoring and influencing a who’s-who of modern SaaS sales leaders. AGENDA: 03:33 The Art...
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20VC: Anthropic Raises $30BN from Microsoft and NVIDIA | NVIDIA Core Business Threatened by TPU | Sam Altman's "War Mode" Analysed | Sierra Hits $100M ARR: Justifies $10BN Price? | Lovable Hits $200M ARR & Rumoured $6BN Round
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
AGENDA: 04:06 Anthropic's $30BN Investment from Microsoft and NVIDIA 07:01 Google vs. OpenAI: Sam Altman’s “War Mode” Memo 15:27 NVIDIA’s Customer Concentration: Bull or Bear 22:12 Is “War Mode” BS: Does Hyper-Aggressive Ever Work? 36:12 Sierra Hits $100M ARR: Justify $10BN Price? 46:14 Implementation is the Biggest Barrier to Enterprise AI Growth 01:04:04 Is LLM Search Optimisation (GEO) Selling Snake Oil? What AI is a Fraud vs Real? 01:14:27 Figma Market Cap: Is the IPO Market F****** for 2026
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20VC: Base44's Maor Shlomo on How Vibe Coding Will Kill SaaS and Salesforce | Why it is BS that Vibe Coding Platforms Do Not Have Defensibility and Bad Margins | Why He Worries About Google, Not Replit and Lovable | Why Long Anthropic, Not OpenAI?
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Maor Shlomo is the Founder and CEO of Base44, the AI building platform that Maor built from idea to $80M acquisition by Wix, in just 8 months. Today the company serves millions of users and will hit $50M ARR by the end of the year. Before Base44, Maor was the Co-Founder and CTO of Explorium. AGENDA: 00:05 – 00:10: How Vibe Coding is Going to Kill Salesforce and SaaS 00:13 – 00:15: Do Vibe Coding platforms have any defensibility? 00:22 – 00:24: I am not worried about Replit and Lovable, I am worried about Google… 00:28 – 00:29: Margins do not matter, the price of the models will go...
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20VC: Max Altman on The New Seed War: Can Anyone Compete with Sequoia and a16z | Leaving $2BN on the Table with Reddit | Lessons from Backing Rippling at $25M Post | Why Climate Tech is a Mirage and Disaster
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Max Altman is Co‑Founder & Managing Partner at Saga Ventures, a US$125 M early‑stage fund. Before Saga Max was an investor with Apollo Projects, Hydrazine Capital and Altman Capital (where he helped deploy over US$500 M) into breakout names such as Rippling and Reddit. AGENDA: 03:55 – Venture Capital Is FULL of Tourists With Single-Digit IQs 06:20 – Inside the Madness of Parker Conrad: Genius, Chaos, and WTF Emails 10:35 – The Rippling Deal That Changed Everything 12:40 – Living in Sam Altman’s Shadow: The Confession 17:30 – $200M Fund Mistakes: Max’s...
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20VC: Cursor Raises $2.3BN: Who Wins the Coding War | Peter Thiel and Softbank Sell NVIDIA: Analysed | Why Venture Capital Will Hit $1TRN and the Opening of Retail | Why Stripe and the Best Companies Will Never Go Public
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
AGENDA: 04:47 Cursor Raises $2.3BN at $29BN Valuation 11:36 What Gemini 3 Means for Lovable, Cursor and Replit 30:54 Peter Thiel and Softbank Sell NVIDIA: The Bubble Bursting? 48:54 Oracle Credit Default Swaps: The Risk is Increasing 01:07:22 Stripe Does Tender at All-Time High: Why the Best Companies Will Never IPO 01:19:18 Why Retail WIll Cause a Surge of Capital into VC Funds
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20VC: Andrew NG on The Biggest Bottlenecks in AI | How LLMs Can Be Used as a Geopolitical Weapon | Do Margins Matter in a World of AI? | Is Defensibility Dead in a World of AI? | Will AI Deliver Masa Son’s Predictions of 5% GDP Growth?
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Dr. Andrew Ng is a globally recognized leader in AI. He is Founder of , Executive Chairman of , General Partner at , Chairman and Co-Founder of . As a pioneer in machine learning Andrew has authored or co-authored over 200 research papers in machine learning, robotics and related fields. In 2023, he was named to the Time100 AI list of the most influential AI persons in the world. Agenda: 03:19 What are the Biggest Bottlenecks in AI Today? 08:51 How LLMs Can Be Used as a Geopolitical Weapon 15:48 Should AI Talent Really Be Paid Billions? 29:07 Why is the Application Layer the Most...
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20Product: How AI Changes Product Design | Does the Design Phase Become Irrelevant in a World of Vibe Coding | The Five Pillars of Truly Great Product Design with Carl Rivera, Chief Design Officer at Shopify
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Carl Rivera is the Chief Design Officer at Shopify, where he previously led both Merchant Services and the Shop App as VP of Product. Before joining Shopify through its acquisition of Tictail, Carl was the co-founder and CEO of Tictail, the “Tumblr for e-commerce,” where he built one of the most beloved design-forward commerce platforms of its era. AGENDA: 05:05 Biggest Lessons from Selling My Company to Shopify 09:55 Where Does Shopify Suck at Product: Lessons from that? 17:37 What makes Truly Great product Design: The Five Pillars 31:02 The Future of Design in an AI-Driven World 36:00 Do...
info_outlineKeith Rabois is a General Partner @ Founders Fund, one of the most successful venture firms of the last decade with home runs in the likes of SpaceX, Palantir, Stripe, Anduril, Facebook, Airbnb, Nubank and many more. As for Keith, he led the first institutional investments in DoorDash, Affirm and has also led investments in Ramp, Trade Republic, Faire and Stripe. Prior to venture, Keith had the most stellar operating career, joining PayPal when their monthly burn-rate was $6 million; Keith joined LinkedIn, Slide and Square when they had no revenue. Fun fact, five companies Keith helped build are now publicly traded with market caps >$1 Billion. Three others have been acquired for greater than $1 Billion or are publicly traded IPOs. If that was not enough, Keith is also the Co-Founder and CEO @ OpenStore, acquiring small DTC businesses.
In Today’s Episode with Keith Rabois You Will Learn:
1.) How Keith first came up with the idea for Opendoor? How a conversation with Peter Thiel led to the founding of the first iteration of the company? Why did it take Keith close to a decade to pursue the idea fully, post having the idea in 2003?
2.) The Market: What made Keith so excited to pursue Opendoor from a top-down market analysis perspective? What does Keith look for in markets he likes to invest in? How did Keith expect the market to change and evolve? What did the market do differently to how Keith thought it would behave?
3.) The Business Model: With debt being the oxygen for Opendoor, how many homes did they need to acquire before they could prove they could price homes accurately? What were Keith's lessons from the first homes they bought? What did not go to plan? Why does Keith disagree, if macro hits real estate, Opendoor's model is challenged? Why does Keith believe it is stronger then?
4.) The Team: What does Keith look for in the founding teams he backs? How does Keith detect diamonds in the rough? How can teams systematically de-risk an opportunity with their experience? With the benefit of hindsight, what would Keith have done differently with the team?
5.) The Funding: Was fundraising for Opendoor always easy? How did the seed round go down? How does Keith feel today about pre-emptive rounds where little company development has taken place? Why did Opendoor decide to SPAC? Why not a direct list? Was this the right choice? What makes for the best SPAC partner?