Uncapped with Jack Altman

Uncapped #50 | Tobi Lütke from Shopify

Tobi Lütke is the co-founder of Shopify, where he has served as the company's CEO since 2008. Under his leadership, Shopify grew from an online snowboard shop in Ottawa, Canada in 2004 to the world's leading e-commerce platform, powering over 4 million merchants in more than 175 countries. The company went public in 2015 at a $1.27 billion valuation and has since grown to a market cap exceeding $100 billion. As a programmer Tobi has served on the core team of the Ruby on Rails framework and has created many popular open source libraries such as the Typo weblog engine, Liquid and Active Merchant. We discussed building Shopify over more than 20 years, what it takes to sustain a life’s work, and why founder-led companies can move faster through major technological shifts. We also talked about how AI is reshaping software, entrepreneurship, and team building. Along the way, Tobi shared his views on originality, product craftsmanship, the future of work, and why he believes AI will create far more opportunity than scarcity. --- Timestamps: (0:00) Intro (0:49) A problem worth solving (5:58) Building products people love (10:14) Why originality matters (11:47) Conformity in Silicon Valley (15:47) Founder-led companies (18:44) Shopify’s AI transition (23:52) Building with urgency (26:52) AI for small businesses (35:18) Raising the standard of living (41:11) Predicting the future with AI (48:14) Changing perception on talent (55:34) Reading and curiosity --- Links: https://x.com/tobi https://x.com/jaltma https://www.shopify.com/ https://uncappedpod.com/ --- friends@uncappedpod.com

Uncapped #49 | Kevin Hartz & Bennett Siegel from A*

Kevin Hartz and Bennett Siegel are co-founders and GPs at A*, a five year old early-stage venture capital firm with $1B in AUM. A* has invested in companies like Notion, Cape, Whop, Paraform, Simile, Krea, Mercor, Watney Robotics, Andera and others. Kevin is also the co-founder of Eventbrite (NYSE: EB) and co-founder and board member of Xoom, an online money transfer service that IPO’d in 2013 and later acquired by PayPal for $1.1B. Notable investments, primarily at the seed/early stages, include PayPal, Airbnb, Pinterest, Reddit, Anduril, and Palantir among others. Bennett was previously a partner at Coatue building out their venture capital business where he invested in earliest financing rounds for Ramp and Decagon, among other investments. We discussed how AI is reshaping venture capital, software, and startup building – from the rise of younger founders and AI researcher-led companies to the growing pressure on traditional software businesses. We also covered the changing economics of seed investing, the influx of mega funds into early-stage venture, AI rollups, robotics, and why this may become the biggest technology boom yet. --- Timestamps: (0:00) Intro (0:25) The A* Capital story (1:16) Why big funds went into seed (7:50) The mother of all bubbles (10:46) Why founders are getting younger (13:00) Mapping talent, not markets (16:31) The rise of AI researcher founders (19:16) Why seed investing is so hard (22:54) Concentration and venture returns (27:34) The AI rollup craze (31:15) AI vs traditional software (33:15) Robotics and the future of AI (35:39) What’s next for A* Capital --- Links: https://x.com/kevinhartz https://x.com/BennettSiegel https://x.com/jaltma https://www.a-star.co/ https://uncappedpod.com/ --- friends@uncappedpod.com

Uncapped #48 | Tarek Mansour from Kalshi

Tarek Mansour is the co-founder and CEO of Kalshi. Kalshi is a regulated prediction market exchange valued at $22B in 2026 where people trade on the outcomes of real-world events – things like inflation prints, Fed decisions, elections, or weather events. Instead of betting against a house, users trade against each other in a market, and prices reflect the collective probability of an outcome happening. Before starting Kalshi, Tarek worked as a quantitative trader at Goldman Sachs as a structured credit and equities analyst and at Citadel as a global macro trader. During his time at these firms, he realized a common thread: a lot of trading stemmed from an opinion on a future event. We covered the idea behind prediction markets and how they offer a more direct way to trade on beliefs about the future. The conversation follows the long, difficult path to building a regulated exchange in the U.S., from early skepticism to ultimately winning a landmark legal battle. We also discuss how these markets can improve forecasting, enable new forms of hedging, and change how information gets priced. --- Timestamps: (0:00) Intro (0:23) Kalshi’s genesis (5:05) Regulation-focused from inception (11:06) Suing the government (18:02) Gambling vs. financial markets (20:58) Defining insider trading (25:38) Incentive structure of the system (32:40) Investing vs. trading (35:31) Hedging use cases (41:38) Scaling a lean team (44:02) Defining Kalshi’s culture --- Links: https://x.com/jaltma https://x.com/mansourtarek_ https://kalshi.com/ https://uncappedpod.com/ --- friends@uncappedpod.com

Uncapped #47 | Max Mullen from Instacart

Max Mullen is the co-founder of Instacart and an active investor having invested in 100+ companies including Gumloop, Mercury, Owner among others. He also runs a founder community in San Francisco called Workshop. We discussed the full arc of building Instacart from a contrarian idea that investors rejected to a $10B consumer marketplace. Max highlighted the scrappy early days, marketplace product-market fit, and key inflection points like retailer partnerships and the Amazon–Whole Foods moment. We also explored what makes great consumer founders, why the best ideas look wrong at first, and how to build and scale in “hard mode” markets. Finally, the conversation touched on investing, decision-making frameworks, and what it takes to win in consumer over the long term. --- Timestamps: (0:00) Intro (0:36) The inception of Instacart (4:55) Finding product market fit (7:20) Landing Trader Joe’s (11:04) Big levers for growth (13:36) Operationally complex businesses (14:55) Amazon’s acquisition of Whole Foods (17:50) COVID and Instacart’s IPO (20:02) Prioritizing profitability (23:21) Avoiding temptations (24:59) The future of Instacart (25:53) Investing in consumer (28:21) Irrationally optimistic founders (29:49) B2B vs consumer founders (30:35) How to work with investors (33:38) Building Workshop --- Links: https://x.com/Max https://x.com/jaltma https://maxmullen.com/ https://uncappedpod.com/ --- friends@uncappedpod.com

Uncapped #46 | Brad Lightcap from OpenAI

Brad Lightcap serves as OpenAI's COO, overseeing its business, operations, and strategic partnerships across Research, Applied AI, and go-to-market. He also manages the OpenAI Startup Fund. Previously, Brad was part of Y Combinator Continuity and led finance and operations initiatives at Dropbox. We discussed the shift from chat-based AI to agents that can take action, and what that means for software and the broader economy. We also covered how these systems are being built and deployed, how tools like Codex are changing how work gets done, and what this next phase of AI unlocks for startups and incumbents alike. --- Timestamps: (0:00) Intro (0:39) The early days of OpenAI (3:47) A research centric culture (7:32) Post-ChatGPT chapters (11:54) Sci-Fi future or good software (15:26) AI’s impact on rural communities (18:57) Codex and coding of the future (24:04) Doing a lot of things at once (27:55) What VCs should invest in (35:43) The software sell off (38:23) Using Codex over ChatGPT (42:32) FDEs and Private Equity (44:53) Working with Sam --- Links: https://x.com/bradlightcap https://x.com/jaltma https://openai.com/ https://uncappedpod.com/ --- friends@uncappedpod.com