20VC: Annie Duke on Reversible vs Irreversible Decisions, How To Evaluate Risk, The Theory of Sunk Cost in Venture & How to Optimise Both the Discussion and Quality of Investment Decisions
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Release Date: 01/11/2021
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...
info_outlineThe 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
info_outlineThe 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...
info_outlineThe 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...
info_outlineThe 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
info_outlineThe 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...
info_outlineThe 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_outlineThe Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
AGENDA: 04:22 Sequoia's Leadership Transition 09:46 Michael Burry's Big Short on Nvidia and Palantir 17:41 Gamma Raises $100M at a $2BN Valuation 32:34 Does Defensibility Exist Today When Copying is Easy 40:31 Should All Funds Be Way More Diversified 47:12 How to Run a Fundraising Process & What Not To Do 57:57 Datadog Surges 20% and Duolingo Crashes: What Happened
info_outlineThe Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Ev Randle is a General Partner @ Benchmark, one of the best funds in venture capital. In their latest fund, they have Mercor ($10BN valuation), Sierra ($10BN valuation), Firework ($4BN valuation), Legora ($2Bn valuation) and Langchain ($1.4Bn valuation). To put this in multiples on invested capital, that is a 60x, two 30x and two 20x. Before Benchmark, Ev was a Partner @ Kleiner Perkins and before Kleiner, Ev was an investor at Founders Fund and Bond. AGENDA: 05:25 Biggest Investing Lessons from Peter Thiel, Mary Meeker and Mamoon Hamid 14:36 OpenAI Will Be a $TRN Company & OpenAI or...
info_outlineThe Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Chad Peets is one of the greatest sales leaders and recruiters of the last 25 years. From 2018 to 2023, Chad was a Managing Director at Sutter Hill Ventures. Chad has worked with the world's best CEOs and CROs to build world-class go-to-market organizations. Chad is currently a member of the Board of Directors for Lacework and Luminary Cloud and on the boards of Clumio and Sigma Computing. He previously served as a board member for Astronomer, Transposit, and others. He was an early-stage investor at Snowflake, Sigma, Observe, Lacework, and Clumio. In Today's Discussion with Chad Peet's We...
info_outlineAnnie Duke is a former professional poker player and the author of National Bestseller, "Thinking in Bets" & "How To Decide". During her poker playing days, Annie was a World Series of Poker bracelet winner, the winner of the 2004 Tournament of Champions and the only woman to win the NBC National Poker Heads Up Championship. Today, Annie is also the founder of How I Decide, a non-profit that creates curricula and tools to improve decision making and critical thinking skills for under-served middle schoolers.
In Today’s Episode You Will Learn:
1.) How Annie made her way from professional poker player to National Bestselling author and coach to the world's leading investors?
2.) How does Annie evaluate the nature of risk? What is good risk vs bad risk? How does Annie think through reversible vs irreversible decisions? What is her framework? Why does Annie believe most irreversible decisions are actually reversible? How does it change your thinking?
3.) How does effective solo-decision-making differ from effective group decision-making? What decision-making biases does Annie often see venture being guilty of making? What 3 things can one do to improve the decision-making of the collective group?
4.) How does Annie think about sunk cost? How does one know when enough is enough and you have to walk away? How does this tie into Annie's thinking on portfolio theory? How does Annie think about pre-mortems? How should they be structured? What is included?
5.) How does Annie define critical thinking? What tips would Annie give to someone in really advancing their level of critical thinking? What behaviours can one implement to seek to protect critical thinking? How does this differ in team environments?
Item’s Mentioned In Today’s Episode
Annie’s Favourite Book: The Success Equation: Untangling Skill and Luck in Business, Sports, and Investing
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