Uncapped with Jack Altman

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.

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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

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Links:

https://x.com/kevinhartz

https://x.com/BennettSiegel

https://x.com/jaltma

https://www.a-star.co/

https://uncappedpod.com/

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[email protected]

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.

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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

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Links:

https://x.com/jaltma

https://x.com/mansourtarek_

https://kalshi.com/

https://uncappedpod.com/

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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.

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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

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Links:

https://x.com/Max

https://x.com/jaltma

https://maxmullen.com/

https://uncappedpod.com/

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[email protected]

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.

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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

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Links:

https://x.com/bradlightcap

https://x.com/jaltma

https://openai.com/

https://uncappedpod.com/

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[email protected]

Ron Conway is the Founder and a Managing Partner of SV Angel. He has been an active angel investor since the mid-90s and has received wide recognition for his role in the tech ecosystem. He has been included on Vanity Fair’s 100 most influential people in the Information Age, awarded Best Angel at the TechCrunch Crunchies Awards, and has been named on Forbes Magazine's Midas list of top “deal-makers” since 2011. Prior to founding SV Angel, Ron was with National Semiconductor Corporation in marketing positions (1973-1979), Altos Computer Systems as a co-founder, President, and CEO (1979-1990), taking the company public on Nasdaq in 1982.

Ron reflects on decades of investing, from semiconductors to AI, and what it really means to be an “all in” partner to founders. He shares how relationships compound into an unfair advantage, why the best investors show up at inflection points, and how being willing to fight, whether in boardrooms or Washington, can change outcomes.

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Timestamps:

(0:00) Intro

(1:50) From semiconductors to AI

(8:39) Two investments that changed everything

(11:46) Nonpassive angel investing

(14:57) Becoming a relationship broker

(18:00) Building authentic relationships

(24:48) Going deep with OpenAI and Airbnb

(29:19) Fighting for founders

(31:39) Remarkable returns at seed

(33:20) The state wealth tax

(37:17) Tech and politics

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Links:

https://x.com/RonConway

https://x.com/jaltma

https://svangel.com/

https://uncappedpod.com/

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[email protected]