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1:38:44ENDavid Tisch and Terrence Rohan on Seed Investing, Conviction and Founder RelationshipsGast: David Tisch, Terrence Rohan · Moderation: Harry StebbingsTwo seed investors discuss price, group decisions, follow-on capital and the limits of investor influence—and disagree on signaling.
58:00ENRyan Akkina on MIT’s Venture Portfolio and Direct Co-InvestingGast: Ryan Akkina · Moderation: Harry StebbingsThe MIT investment team member discusses manager selection, liquidity, co-investment structures and the long feedback loop in venture capital.
1:17:39ENAdam Fisher on Small Markets, Founder Partnerships and Venture ExitsGast: Adam Fisher · Moderation: Harry StebbingsThe Bessemer investor explains why he favors less crowded opportunities, how he thinks about follow-on capital and what he has learned from exits.
1:15:48ENKeith Rabois on Returning to Khosla Ventures and Investing at SeedGast: Keith Rabois · Moderation: Harry StebbingsThe investor compares partnership styles, explains his approach to price and follow-on capital, and reflects on exits and founder relationships.
1:22:17ENPeter Lacaillade on Selecting Managers, Co-Investment and LiquidityGast: Peter Lacaillade · Moderation: Harry StebbingsThe SCS Financial investor explains his barbell portfolio, how he diligences managers and why liquidity decisions deserve more attention.
1:03:42ENDominik Richter on Building HelloFresh and Choosing a Path to LiquidityGast: Dominik Richter · Moderation: Harry StebbingsThe HelloFresh founder discusses operational complexity, capital allocation, venture funding and the trade-offs of an early IPO.
1:16:45ENNick Tomaino on Crypto Investing, FTX and the NFT DebateGast: Nick Tomaino · Moderation: Harry StebbingsThe 1confirmation founder discusses fund discipline, token incentives, OpenSea and the limits of conviction in a 2023 conversation.
1:00:35ENBeezer Clarkson on LP Liquidity, Venture Returns and Fund IncentivesGast: Beezer Clarkson · Moderation: Harry StebbingsThe Sapphire Partners investor explains how LPs assess managers, fund size and distributions during a difficult 2023 fundraising market.
1:13:49ENMarcelo Claure and Shu Nyatta on Building Bicycle Capital in Latin AmericaGast: Marcelo Claure, Shu Nyatta · Moderation: Harry StebbingsThe former SoftBank partners discuss a proposed growth fund, regional liquidity and lessons from missed opportunities and investment mistakes.
1:05:26ENStephane Kurgan on Scaling King, Making Decisions and Building TrustGast: Stephane Kurgan · Moderation: Harry StebbingsThe former King COO explains how he approaches data, communication, hiring and the difficult choices that come with rapid growth.
1:07:41ENRob Go on Raising Venture Funds and Building LP RelationshipsGast: Rob Go · Moderation: Harry StebbingsThe NextView co-founder explains fund construction, anchor investors, fundraising follow-up and the trade-offs in seed investing.
1:07:30ENAdam Besvinick on Pre-Seed Investing and Raising a Small FundGast: Adam Besvinick · Moderation: Harry StebbingsThe Looking Glass Capital founder explains fund construction, LP relationships, thematic investing and a volatile fundraising market.
1:29:33ENNico Wittenborn on Consumer Subscriptions and Solo InvestingGast: Nico Wittenborn · Moderation: Harry StebbingsThe Adjacent founder discusses retention, acquisition, fund construction and how evolving trends shape early-stage bets.
56:43ENVince Hankes on Thrive’s OpenAI Investment and AI CompetitionGast: Vince Hankes · Moderation: Harry StebbingsThe Thrive partner explains his investment reasoning, the risks of rapid technology shifts and lessons from missed opportunities.
1:23:23ENTobi Lütke on Learning, Creative Constraints and Leading ShopifyGast: Tobi Lütke · Moderation: Harry StebbingsThe Shopify CEO explains how he updates his mental models, why constraints can help teams create and how he weighs remote work against proximity.
48:44ENDara Khosrowshahi on Leading Uber, Marketplace Trade-offs and Learning from MistakesGast: Dara Khosrowshahi · Moderation: Harry StebbingsUber’s CEO discusses the move from Expedia, the company’s bets on delivery and acquisitions, and why reversible decisions deserve a different pace.
55:48ENMike Maples on SVB, Crisis Planning and Investing Through UncertaintyGast: Mike Maples · Moderation: Harry StebbingsThe Floodgate co-founder draws lessons from the 2023 bank failure for founders, then discusses AI risk, fund pacing and returns.
1:06:55ENBill Ackman on Investment Mistakes, the SVB Crisis and Economic PolicyGast: Bill Ackman · Moderation: Harry StebbingsThe Pershing Square founder discusses Netflix, position sizing and his 2023 proposals for bank deposits, alongside his views on inequality and tax.
1:02:29ENOphelia Brown on Building Blossom and Investing in European StartupsGast: Ophelia Brown · Moderation: Harry StebbingsThe Blossom Capital founder explains her concentrated Series A strategy, fundraising lessons and views on the European venture market in 2023.
52:43ENJackie Reses and Kris Dickson on the SVB Failure and Depositor ConfidenceGast: Jackie Reses, Kris Dickson · Moderation: Harry StebbingsDuring the March 2023 crisis, two Lead Bank executives explain the bank run, resolution possibilities and the questions facing depositors.
51:40ENHunter Somerville on Venture Secondaries, Liquidity and LP DecisionsGast: Hunter Somerville · Moderation: Harry StebbingsThe StepStone partner explains secondary structures, discounts and allocation pressures in a 2023 venture market with limited liquidity.
1:10:33ENDavid Tisch on Seed Fund Math, Valuations and Founder–Investor AlignmentGast: David Tisch · Moderation: Harry StebbingsThe BoxGroup investor debates small checks, reserves and fundraising trade-offs with Harry Stebbings, and explains why he favors a flexible seed strategy.
42:16ENJoey Levin on Investing, Simplicity and Leading Through a Market ResetGast: Joey Levin · Moderation: Harry StebbingsThe IAC CEO discusses valuation, SPACs, company values and persistence in a February 2023 conversation.
58:33ENSteve Pagliuca on Investing, Sports Ownership and the Chelsea BidGast: Steve Pagliuca · Moderation: Harry StebbingsThe Bain Capital investor and Celtics co-owner discusses long-term growth, team culture and his group’s unsuccessful Chelsea bid.
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