Uncapped with Jack Altman
Conversations with people I admire about things I’m genuinely interested in.
Episodes
Uncapped #52 | Mike Volpi from Hanabi Capital
Mike Volpi is a General Partner at Hanabi Capital, with a background that spans senior operating roles and nearly two decades of investing. Mike currently sits on the boards of several innovative companies, including Scale AI, ClickHouse, Ferrari, and Confluent, where he is known as a thoughtful sounding board and a steady presence through the highs and lows of startup life.
Mike is a retired par
Uncapped #51 | Joe Lonsdale from 8VC
Joe Lonsdale is the Founder and Managing Partner at 8VC, an early-stage venture capital firm managing over $6 billion in capital. In 2003, he founded Palantir (NASDAQ:PLTR), a global software company known for its work supporting US and its allies’ defense and intelligence. Since then, he has founded over a dozen prominent companies, including Addepar, a wealth management platform helping investor
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
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 an
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 hap
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 produ
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 sof
Uncapped #45 | Ron Conway from SV Angel
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-make
Uncapped #44 | Max Junestrand from Legora
At 23, with no legal background, Max Junestrand co-founded Legora to transform how lawyers work.
Legora recently (March 2026) raised $550 million at a $5.55 billion valuation in a Series D funding round to accelerate its expansion across the United States. Over the past year, Legora has grown from 40 to 400 team members across the globe and the platform supports tens of thousands of lawyers each
Uncapped #43 | Garry Tan, Harj Taggar, and Jared Friedman from YC
In this episode, the team behind Y Combinator reflects on what has — and hasn’t — changed since the early days of YC, and how AI is reshaping what it means to be a founder. They discuss how they evaluate builders now, why execution still matters more than competition, and what YC is prioritizing as the startup landscape evolves. At its core, the mission remains the same: increase the number of gre
Uncapped #42 | Bret Taylor from Sierra
Bret Taylor is the founder and CEO of Sierra, an AI agent company transforming customer service. Bret’s legendary career includes being CTO of Meta, co-CEO of Salesforce, chairman of the board at OpenAI, co-creating both Google Maps and the Like button, and founding three companies.
We unpacked the so-called “SaaS-pocalypse” and what AI agents mean for the future of enterprise software. We talke
Uncapped #41 | The Benchmark Partnership
In this episode, the Benchmark partnership explains why they’ve resisted scale, eliminated residual economics, and built an equal partnership designed to endure. We talk about what that choice enables – for founders, for decision-making, and for practicing venture as a craft rather than a factory.
Peter Fenton is the longest-serving full-time general partner at Benchmark. Over the last two decade
Uncapped #40 | Vinod Khosla and Keith Rabois from Khosla Ventures
Vinod Khosla and Keith Rabois are Managing Directors at Khosla Ventures.
Vinod is an entrepreneur, investor and technologist. In 2004, Vinod formed Khosla Ventures to focus on both for-profit and social impact investments that have included OpenAI, Stripe, DoorDash, Commonwealth Fusion Systems and many more. Vinod previously co-founded Daisy Systems, the first significant computer-aided design s
Uncapped #39 | Daniele Perito from depthfirst
Daniele Perito is Co-founder and Executive Chairman of depthfirst, an AI-native security platform that understands your code, business logic, and infrastructure to find real vulnerabilities, slash false positives, and give developers actionable fixes in their workflow.
Daniele is also Co-founder and Board Member of Faire, where he previously served as Chief Data Officer and helped build the compa
Uncapped #38 | Ben Horowitz from a16z
Ben Horowitz is a cofounder and general partner at the venture capital firm Andreessen Horowitz, a venture capital firm that manages $60 billion in assets under management. He is also the author of the New York Times bestsellers, The Hard Thing About Hard Things and What You Do Is Who You Are.
Prior to a16z, Ben was cofounder and CEO of Opsware (formerly Loudcloud), which was acquired by Hewlett
Uncapped #37 | Saam Motamedi from Greylock Partners
Saam Motamedi is a General Partner at Greylock Partners working with enterprise software entrepreneurs at the seed and early stages who are focused on new opportunities in intelligent applications, cybersecurity, AI, and data infrastructure. In 2019 at just 26 years old, Saam became the Greylock’s youngest General Partner in its 54-year history – a remarkable achievement at an institution that had
Uncapped #36 | Pat Grady & Alfred Lin from Sequoia
Pat Grady and Alfred Lin are partners at Sequoia and were recently named as the storied firm’s new co-stewards. Alfred joined the firm in 2010, where he has led major investments into category-defining companies like Airbnb, DoorDash, and Kalshi. Pat has been a partner at the firm for nearly 19 years and has led Sequoia’s growth-stage investing since 2015, backing companies like Snowflake, OpenAI,
Uncapped #35 | Trae Stephens from Founders Fund
Trae Stephens is a Partner at Founders Fund. He is also Co-founder and Executive Chairman of Anduril, a defense tech company focused on autonomous systems, and Co-founder of Sol, a next generation wearable e-reader. Previously, Trae was an early employee at Palantir Technologies, where he led teams focused on growth in the intelligence/defense space as well as international expansion. He was also
Uncapped #34 | Mel Williams from TrueBridge
Mel Williams is a co-founder and Partner at TrueBridge Capital Partners, a fund of funds with $8 billion in AUM focused on venture capital. Since 2007, Mel’s team has backed firms like Thrive, Founders Fund, Sequoia, and Alt Capital, and powers the data behind the Forbes Midas List. Before TrueBridge, Mel co-founded UNC Management Company (UNCMC), where he worked closely with the President/CIO to
Uncapped #33 | Vlad Tenev from Robinhood
Vlad Tenev is the co-founder and CEO of Robinhood (NASDAQ: HOOD), which transformed financial services by introducing commission-free stock trading and democratizing access to the markets for millions of investors. As of Q3 2025, the company is doing $1.27 billion in revenue with 11 business lines each doing roughly $100 million.
We discuss the evolution of online brokerage platforms from Schwab
Uncapped #32 | Kyle Vogt from The Bot Company
Kyle Vogt is a serial entrepreneur and engineer often recognized as the co-founder and former CEO of Cruise, the autonomous vehicle company acquired by General Motors for $1 billion. Before Cruise, he co-founded Twitch, which transformed how people watch and share gaming online. Kyle is now building a new company at the frontier of intelligent home automation, aiming to bring advanced robotics int
Uncapped #31 | Dylan Field from Figma
Dylan Field is the co-founder and CEO of Figma, a design software company that went public in July 2025. Founded in 2012, Figma transformed how people design, prototype, and build products together. After a $20 billion acquisition attempt by Adobe collapsed in 2022 because of regulators, Dylan helped Figma rebound stronger than ever. Just three years later, Figma listed its shares at nearly $20 bi
Uncapped #30 | Alex Pall from The Chainsmokers
Alex Pall is half of the Grammy Award-winning duo The Chainsmokers. Beyond music, Alex is entrepreneur and co-founder of Mantis VC, a venture firm that invests opportunistically in early stage tech-enabled startups. Some of their investments include Alchemy, Chainguard, Kalshi, Roblox, and Rogo. We had a wide ranging conversation that broke down the creative stories behind a few of their top hits
Uncapped #29 | Thomas Laffont from Coatue
Thomas Laffont is the co-founder of Coatue, one of the world’s largest technology investment platforms active in both the public and private markets. Thomas leads the firm’s private investment platforms across early-stage and growth, and oversees their software investments across private and public markets. Coatue has partnered with some of the most enduring and impactful companies of the last two
Uncapped #28 | Roelof Botha from Sequoia
Roelof Botha joined Sequoia in 2003 and serves as the managing partner and steward. Roelof led early investments in YouTube, Instagram, Natera, and MongoDB among others. He currently sits on the board of Natera, Unity, Block (fka Square), MongoDB, Ethos, Pendulum, Airtime, and Flow Engineering. Roelof also co-led Sequoia’s backing of Elon Musk’s acquisition of Twitter (now X) in 2022. Prior to Seq
Uncapped #27 | Vince Hankes from Thrive Capital
Vince Hankes is a Partner at Thrive Capital where he’s worked on investments in OpenAI, SpaceX, Databricks, and Stripe among others. Vince invests across all stages and currently sits on the board of Airtable, Benchling, Console, Isomorphic, Lattice and Rogo. Prior to joining Thrive, Vince was an investor at Tiger Global.
We covered:
Non-consensus investing
Writing billion dollar checks
Uncapped #26 | Ali Rowghani
Ali Rowghani is the founder of First Harmonic, a go-to-market program purpose-built for seed stage founders.
Ali has had a long, distinguished career in tech. He worked with Steve Jobs and Ed Catmull at Pixar for nine years holding various roles including CFO and SVP of Strategic Planning, took Twitter from $0 in revenue through IPO as the CFO and COO, and most recently was the founding Managing
Uncapped #25 | Lulu Cheng Meservey
Lulu Cheng Meservey is the leading voice in the new age of PR and comms and is the founder of Rostra, an advisory firm helping founders go direct.
Lulu has been a trusted voice for founders like Palmer Luckey at Anduril, Eric Glyman at Ramp, and Brian Armstrong at Coinbase. She previously ran corporate affairs and communications for Activision Blizzard and was the head of comms for Substack.
L
Uncapped #24 | Balaji Srinivasan
Balaji Srinivasan is an angel investor, tech founder, and WSJ bestselling author of The Network State. He is currently the founder of The Network School, a frontier community for techno-optimists.
Formerly the CTO of Coinbase and General Partner at Andreessen Horowitz, he is an early investor in many successful tech companies, including Anduril, Perplexity, OpenSea, Alchemy, StarkWare, Dapper Lab
Uncapped #23 | Martin Casado from a16z
Martin Casado is a general partner at a16z, where he leads the firm’s $1.25 billion infrastructure practice. Martin has led investments in Cursor, dbt Labs, and Fivetran to name a few. Prior to joining a16z in 2016, he was the co-founder and CTO of Nicira, which was acquired by VMware for $1.26B. While at VMware, Martin was the SVP and GM of network and security, which he scaled to a $600 million
Uncapped #22 | Greg Rosen from BoxGroup
Greg Rosen is a Partner at BoxGroup. Greg was the first hire at BoxGroup outside of the founders, David Tisch and Adam Rothenberg. After moving to the West Coast to work with Benchmark and Bedrock, Greg rejoined BoxGroup and currently invests out of their San Francisco office. An engineer by training, Greg built iOS games in high school before dropping out of college at 19 to join Jim Pallotta's v
Uncapped #21 | Brian Armstrong from Coinbase
Brian Armstrong is the co-founder and CEO of Coinbase, a leading cryptocurrency company that provides exchange, brokerage, and custody services to 100M+ verified users in over 100 countries. Founded in 2012, Coinbase went public in 2021 on the NASDAQ under the ticker COIN and as of August 2025 has a market cap of $83 billion. Brian is also the co-founder of New Limit, a longevity biotech company o
Uncapped #20 | Guillermo Rauch from Vercel
Guillermo Rauch is the founder and CEO of Vercel, creators of v0 which is one of the most popular AI app building tools that’s helping power the online presence of companies like Porsche, Under Armour and Nintendo. In May 2024, Vercel completed a $250M Series E at a $3.25B valuation and was recently named to the Forbes Cloud 100. Originally from Argentina, Guillermo became a self-taught developer
Uncapped #19 | Dwarkesh Patel
In his early twenties, Dwarkesh Patel has become one of the leading podcasters with nearly 1 million YouTube subscribers excited to consume his deeply-researched interviews. Dwarkesh has caught the attention of influential figures such as Jeff Bezos, Noah Smith, Nat Friedman, and Tyler Cohen, who have all praised his interviews – the latter describing him as “highly rated but still underrated.” In
Uncapped #18 | Peter Fenton from Benchmark
Peter Fenton is the longest-serving full-time partner at Benchmark, a renowned venture firm known for its artisanal approach and deep alignment with founders. Over the last two decades, Peter led investments in Twitter, Yelp, Elastic, Docker, Zuora, and many others. He also achieved one of the rarest feats in venture history in 2014 when two of his investments, Hortonworks and New Relic, went publ
Uncapped #17 | Christina Cacioppo from Vanta
Christina Cacioppo is cofounder and CEO of Vanta, which is on a mission to secure the internet and protect consumer data. The trust management platform was valued at $2.5 billion in 2024 after a Series C investment led by Sequoia. Vanta went from $10M in annual recurring revenue in 2021 to $100M in 2024, while also giving us one of the best tech billboards of all time, “Compliance that doesn’t SOC
Uncapped #16 | Mamoon Hamid from Kleiner Perkins
Mamoon Hamid is a Partner at Kleiner Perkins. He has been an early investor in and served on the boards of some of the most innovative software companies of recent times including Slack, Figma, Rippling, Glean and Box. Prior to joining Kleiner Perkins, Mamoon was a Co-founder and General Partner at Social Capital. He started his venture career in 2005 at U.S. Venture Partners (USVP) where he event
Uncapped #15 | Vinod Khosla from Khosla Ventures
Vinod Khosla is an entrepreneur, investor and technologist. In 2004, Vinod formed Khosla Ventures to focus on both for-profit and social impact investments that have included OpenAI, Stripe, DoorDash, Commonwealth Fusion Systems and many more.
After graduating college, Vinod co-founded Daisy Systems, the first significant computer-aided design system for electrical engineers, which led to an IPO.
Uncapped #14 | Dan Feder from the University of Michigan
It was a pleasure to sit down with Dan Feder, Senior Managing Director with the University of Michigan Investment Office who leads the endowment’s investments in venture capital and private equity.
Prior to joining the University of Michigan, Dan was the Managing Director of Private Markets at the Washington University Investment Management Company. Dan’s career in endowment management began at
Uncapped #13 | Sam Altman from OpenAI
This was a fun one! Sam is my brother and the CEO of a small company in SF called OpenAI. I’m glad he was able to take time out of his busy schedule to give me a hard time and share his thoughts on the future of AI.
We covered:
AI discovering new science
The risk of superintelligence
What’s after reasoning
Humans needing humans
The latest with OpenAI
Meta / Scale AI news
Ple
Uncapped #12 | Marc Andreessen from a16z
Marc Andreessen is a cofounder and general partner at the venture capital firm Andreessen Horowitz, a venture capital firm that manages $45 billion in assets under management. He is an innovator and creator, one of the few to pioneer a software category used by more than a billion people and one of the few to establish multiple billion-dollar companies.
Marc co-created the highly influential Mosa
Uncapped #11 | Jordan Bramble from Antares
Jordan Bramble is the CEO of Antares, a nuclear energy company that has raised over $50M to become America’s industrial base partner for special-purpose microreactors.
Antares focuses on high-value use cases in power-constrained environments that wouldn’t be possible without nuclear power. They are developing resilient fission-based power systems for critical assets for the Department of Defense
Uncapped #10 | David Tisch from BoxGroup
This week I enjoyed riffing with David Tisch, Managing Partner of BoxGroup. BoxGroup is an NYC-based seed stage venture capital firm that has invested in over 500 seed-stage startups over the last 15 years, including Plaid, Ro, Ramp, Clay, Scopely, Warp, Cursor, PillPack, Amplitude, Flatiron Health, Stripe, Warby Parker, Harry’s, Oscar, Flexport, Classpass, Vine, GroupMe, Airtable and more. David
Uncapped #9 | Qasar Younis from Applied Intuition
I had a blast sitting down with Qasar Younis, Co-Founder and CEO of Applied Intuition, a company that’s on a mission to accelerate the world’s adoption of safe and intelligent machines. The company builds software that makes it faster, safer, and easier to bring autonomous systems to market. Last valued at $6B, Applied Intuition has raised a total of $602M since its inception in 2017 and plays a c
Uncapped #8 | Josh Kopelman from First Round Capital
It was a pleasure to sit down this week with Josh Kopelman, one of the original architects of seed stage investing who continues to re-invent what it means to operate within venture.
Josh co-founded First Round Capital, which has invested at the earliest stages in companies like Square, Uber, and Roblox. Some of Josh’s more recent investments include Notion, Pomelo Care, Loyal, and Perpay. Since
Uncapped #7 | Garry Tan from Y Combinator
This week I sat down with Garry Tan, President & CEO of Y Combinator. YC has funded 5,000+ startups including Airbnb, Stripe, DoorDash, Rippling, and Reddit, among others that have totaled $600B in combined valuation.
Garry is a designer, engineer, and investor in early stage startups. Previously Founder & Managing Partner of Initialized Capital, an early stage venture capital fund that was earl
Uncapped #6 | Elad Gil
It’s always a pleasure to jam with Elad Gil, a serial entrepreneur and a startup investor. As an early leader at Google, Elad helped build the initial mobile team, before founding MixerLabs, which was acquired by Twitter. Later, he co-founded Color Health, a genetic testing company specializing in cancer detection. Over the past decade, he's backed nearly 40+ companies valued north of $1B each, in
Uncapped #5 | Sarah Guo from Conviction
I was pumped to chat this week with Sarah Guo. Sarah is a startup investor and the founder of Conviction, an investment firm purpose-built to serve intelligent software, or "Software 3.0" companies. Some of her investments include Harvey, Mistral AI, Sierra, Cognition, HeyGen, and Cartesia, among others. Prior to 2022, she spent nearly a decade incubating and investing as a General Partner at Grey
Uncapped #4 | Adam Guild from Owner
Adam Guild is the CEO of Owner, a business he started when he was only 17. It now has tens of millions of revenue, hundreds of employees, and thousands of customers.
I’ve had the pleasure of working on his board for a few years now, and he is one of the most impressive people I’ve ever gotten to know. Working with him was a big part of what made me realize I want to do venture for the rest of my
Uncapped #3 | Aaron Levie from Box
This week I sat down with Aaron Levie, Co-Founder and CEO of Box. Aaron came up with the idea behind the cloud computing company as a 19 year old college student and has led the company since its inception in 2005. Today, Box does over $1B in revenue with a market cap of $4.4B, and has raised over $560 million from the likes of DFJ, Andreesen Horowitz, and Meritech Capital.
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Timestamps:
(0:0
Uncapped #2 | Keith Rabois from Khosla Ventures
This week I enjoyed speaking quickly with Keith Rabois, a Managing Director at Khosla Ventures and the CEO of OpenStore. At Khosla, Keith led the first institutional investments in DoorDash, Affirm, and Faire, invested early in Stripe, and co-founded Opendoor. While a General Partner at Founders Fund, he led investments in Ramp, Trade Republic, and Aven, and before that made early personal investm
Uncapped #1 | Shaun Maguire from Sequoia
This week I spoke with Shaun Maguire, a Partner at Sequoia Capital. He led their investments into SpaceX, The Boring Co, and X among others. Prior to Sequoia Shaun co-founded a cybersecurity company which was acquired for $1B and worked at DARPA. I could have happily spoken with Shaun for four hours.
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We covered:
(0:00) Speaking his mind in public
(13:38) Trust and the media
(24:27) Tech’s
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