Uncapped with Jack Altman

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

Tue, 12 May 2026 09:00:00 -0000

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

Wed, 29 Apr 2026 09:00:00 -0000

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

Thu, 16 Apr 2026 16:00:00 -0000

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

Wed, 01 Apr 2026 09:00:00 -0000

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

Uncapped #45 | Ron Conway from SV Angel

Wed, 25 Mar 2026 09:00:00 -0000

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.

---

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

---

Links:

https://x.com/RonConway

https://x.com/jaltma

https://svangel.com/

https://uncappedpod.com/

---

friends@uncappedpod.com

Uncapped #44 | Max Junestrand from Legora

Thu, 12 Mar 2026 09:00:00 -0000

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 day across 800 customers in more than 50 markets.

Max shares the story of building Legora, what it really means to build AI-native software from day one, why legal work is uniquely suited for AI, and how a small team from Stockholm convinced some of the world’s largest law firms to change how they work.

---

Timestamps:

(0:00) Intro

(0:31) Legora's origin story

(9:05) Building an AI-native company

(18:16) No sacred cows, the models will be amazing

(27:36) Winning pilots and global expansion

(36:43) Starting in Europe

(47:15) Stockholm culture and "blodsmak"

---

Links:

https://x.com/MaxJunestrand

https://x.com/chetanp

https://x.com/jaltma

https://legora.com/

---

https://uncappedpod.com/

friends@uncappedpod.com

Uncapped #43 | Garry Tan, Harj Taggar, and Jared Friedman from YC

Tue, 03 Mar 2026 10:00:00 -0000

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 great startups in the world.

Garry Tan is president and CEO of Y Combinator and a group partner. He was a partner at Y Combinator from 2011 to 2015, where he built key parts of the YC experience for founders including Bookface and the Demo Day website. Garry is the co-founder of Initialized Capital and Posterous (YC S08), a blog platform acquired by Twitter, and prior to that, he was an early designer and engineering manager at Palantir.

Harj Taggar is a Managing Partner at YC. Of the 1,000+ companies Harj has advised while at YC, 5 have gone public. He was previously founder and CEO of Triplebyte (YC S15) and Auctomatic (YC W07), which was acquired by Live Current Media in 2008. He first joined YC as a partner in 2010, leaving in 2014 to start Triplebyte and rejoining in 2020.

Jared Friedman is a Managing Partner at YC. Jared has advised more than 20 YC unicorns while at YC. He was co-founder of Scribd, which was funded by Y Combinator in 2006 and grew to be one of the top 100 sites on the web. Jared previously worked at a pioneering AI company.

---

Timestamps:

(0:00) Intro

(0:18) The YC product

(5:05) AI and the new builder

(13:01) Pivots and upcoming trends

(22:26) Making something people want

(24:50) What’s in store for SaaS

(33:02) Capital in the age of AI

(36:28) The human capacity for desire

(42:18) Building in America

(44:29) Fixing San Francisco

(47:58) Scaling YC

---

Links:

https://x.com/snowmaker

https://x.com/harjtaggar

https://x.com/garrytan

https://x.com/jaltma

https://www.ycombinator.com/

https://uncappedpod.com/

---

friends@uncappedpod.com

Uncapped #42 | Bret Taylor from Sierra

Thu, 19 Feb 2026 10:00:00 -0000

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 talked through the shift from systems of record to autonomous agents, outcome-based pricing, platform transitions, Codex and the transformation of software engineering, and who is structurally positioned to win in the next era of AI.

---

Timestamps:

(0:00) Intro

(0:20) The SaaS-pocalypse and systems of record

(12:34) Sierra's competitive landscape

(17:05) Outcomes-based pricing

(24:22) The rapid evolution of AI support technology

(28:21) Young founders vs. experienced founders

(34:12) Beyond support: The full customer lifecycle

(38:47) Codex and the future of software engineering

(51:49) OpenAI and advertising

(54:59) How to run a board

---

Links:

https://x.com/btaylor

https://x.com/jaltma

https://uncappedpod.com/

---

Email: friends@uncappedpod.com

Uncapped #41 | The Benchmark Partnership

Wed, 04 Feb 2026 10:00:00 -0000

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 decades, Peter led investments in Twitter, Yelp, Elastic, Docker, Zuora, and many others. More recent investments include Sierra, Ollama, ClickHouse, and Airtable. Peter has been on the Forbes Midas list 18 years in a row.

Eric Vishria is a general partner at Benchmark. Eric led investments in Confluent and Amplitude, both of which IPO’ed in 2021. He is also an investor and board member at Cerebras Systems, Benchling, Contentful, among others. Most recent investments include Fireworks, Quilter, and Greptile. Before joining Benchmark, Eric was the co-founder and CEO of a social web browser company called Rockmelt, which was sold to Yahoo.

Chetan Puttagunta is a general partner at Benchmark. Eric is an investor and actively involved with Elastic (which IPO’ed in 2018), Legora, Manus, LangChain, Airbyte, Cursor, Reducto, Numeral, and the list of great companies goes on. Noteworthy exits include MuleSoft, which was acquired for $6.5B by Salesforce and Acquia, which was acquired for $1B in 2019. Prior to Benchmark, Chetan was a general partner at NEA for seven years.

Ev Randle is the newest general partner at Benchmark. Prior to joining the firm, Ev invested in Anthropic, Chainguard, Databricks, Flock Safety, and SpaceX, among others as a partner at Kleiner Perkins. Through his experience at Founders Fund and with personal capital, Ev also has invested in Rippling, Ramp, Wave, Faire, Figma, among others.

---

Timestamps:

(0:00) Intro

(0:18) Becoming more rare to stay small

(4:58) Activities that degrade with scale

(9:08) The principles of Benchmark

(14:07) Contributing as much as you take out

(18:37) Doing the right, hard-to-sell things

(23:31) Benchmark’s relationship with founders

(31:29) What makes a quality investor

(36:15) Cultivating different tastes in founders

(39:56) Spotting special people

(46:06) Consensus vs non-consensus bets

(47:50) Investing in founders, then AI

(53:06) Founder centricity matters more than ever

---

Links:

https://x.com/peterfenton

https://x.com/ericvishria

https://x.com/chetanp

https://x.com/EverettRandle

https://x.com/jaltma

---

https://uncappedpod.substack.com/

Email: friends@uncappedpod.com

Uncapped #40 | Vinod Khosla and Keith Rabois from Khosla Ventures

Wed, 21 Jan 2026 17:26:00 -0000

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 system for electrical engineers, which led to an IPO. He later went on to co-found Sun Microsystems in 1982, serving as its first chairman and CEO. After joining Kleiner Perkins Caulfield and Byers (KPCB), Vinod incubated the idea for Juniper Networks to take on Cisco System’s dominance of the router market.

Keith is also currently the CEO of OpenStore and 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 investments in YouTube, Airbnb, Palantir, Lyft, Udemy, and Eventbrite. Keith started his career in leadership roles at PayPal and LinkedIn before becoming COO of Square.

---

Timestamps:

(0:00) Intro

(0:58) The working relationship

(4:26) Pie chart on what’s discussed

(7:11) Ethos of investors today vs yesterday

(10:42) Comparing FF and KV

(12:46) What makes a great founder

(22:56) Alpha in today’s market

(30:05) Themes within AI

(38:23) AI companies built differently

(46:23) Excitement outside of AI

(53:12) Politically active on X

(58:24) Evolution of political leanings

---

More on Jack:

https://www.altcap.com/

https://x.com/jaltma

---

https://linktr.ee/uncappedpod

Email: friends@uncappedpod.com

Uncapped #39 | Daniele Perito from depthfirst

Wed, 14 Jan 2026 15:23:00 -0000

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 company’s data, risk, and analytics foundations from the early days to a multi-billion dollar valuation. Before co-founding Faire, Daniele worked at Square and was on the founding team of Cash App, where he focused on security, fraud, and risk systems supporting products used by millions of merchants and consumers.

We covered:

Inception stories from Faire and Cash App
The ultimate truth seeking machine
Building superhuman attackers with AI
Who wins over time: attackers vs defenders
Why security feels like its own world

---

Timestamps:

(0:00) Intro

(0:40) The founding Faire insight

(4:34) Operational rigor of marketplace businesses

(10:39) Starting a company now vs in 2017

(12:01) The inception story of Cash App

(16:22) depthfirst’s mission

(18:08) AI security landscape

(26:10) Security is a fantasy world

(31:15) Building superhuman attackers for defense

(38:27) Roles of humans and AI in security

(39:14) Platform vs pipeline businesses

---

More on Jack:

https://www.altcap.com/

https://x.com/jaltma

---

https://linktr.ee/uncappedpod

Email: friends@uncappedpod.com

Uncapped #38 | Ben Horowitz from a16z

Fri, 09 Jan 2026 13:00:00 -0000

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-Packard for $1.6 billion in 2007. Earlier, he was vice president and general manager of America Online’s E-commerce Platform division, where he oversaw development of the company’s flagship Shop@AOL service. Ben also ran several product divisions at Netscape.

Ben serves on the board of Anyscale, Databricks, Mayvenn, NationBuilder, Navan, and UnitedMasters.

We covered:

Marc and Ben’s relationship as co-founders
Operating a venture firm like a CEO of a company
Why scale is important and not for everyone
The evolution of media

---

Timestamps:

(0:00) Intro

(0:30) Marc and Ben’s relationship

(6:10) Structuring the firm to attract great talent

(10:28) Difference between execs and GPs

(14:51) Firm-wide guiding principles

(16:43) Scaling GPs vs small teams who concentrate

(20:11) Why scale is so important in venture

(23:45) What platform services work and don’t work

(26:58) Ben’s view on board seats

(34:56) The evolution of media

(44:44) Laws of physics for fund sizes

(48:28) Winning is more impactful than picking

(52:15) Defending why venture doesn’t scale

(55:00) Hiring ex founders and CEOs

---

More on Jack:

https://www.altcap.com/

https://x.com/jaltma

---

https://linktr.ee/uncappedpod

Email: friends@uncappedpod.com

Uncapped #37 | Saam Motamedi from Greylock Partners

Tue, 16 Dec 2025 10:00:00 -0000

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 backed Airbnb, AppDynamics, Coinbase, Discord, Figma, Instagram, LinkedIn, among others.

Saam’s portfolio spans 14+ companies with collective valuations exceeding $10 billion. Abnormal Security, which Greylock incubated in its offices in 2018 with Saam as founding investor, grew into a multi-billion-dollar email security powerhouse. Cresta, where he led the Series A in 2019, became the leading generative AI platform for contact centers. Snorkel AI, Braintrust, Orb, and a portfolio of other infrastructure companies position Saam at the center of AI's business model transformation.

We covered:

Durable components to great firms
Inside look at how Greylock operates
Cracking the code on incubations
Alpha in today’s venture strategies

---

Timestamps:

(0:00) Intro

(1:32) Greylock turning 60 this year

(4:11) What’s persisted since 1965

(8:59) Apprenticeship

(11:34) What's durable in venture

(16:29) Greylock’s ethos

(19:33) Incentive misalignments

(24:44) Breadth vs depth in venture

(29:28) Managing the team on inputs

(34:00) Why incubations are so hard

(43:22) Finding alpha

(52:38) Greylock’s approach to portfolio services

(59:18) Assessing wild revenue ramps

(1:08:10) Horizontal vs vertical SaaS

(1:11:34) Friendships and work

(1:16:26) Saam's biological age

---

More on Jack:

https://www.altcap.com/

https://x.com/jaltma

---

https://linktr.ee/uncappedpod

Email: friends@uncappedpod.com

Uncapped #36 | Pat Grady & Alfred Lin from Sequoia

Tue, 09 Dec 2025 10:00:00 -0000

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, and Harvey. In this episode, we unpack how Sequoia actually works: their partnership model, how they pick outliers, and what stewardship means inside one of the most respected firms in venture capital.

Some highlights:

Consensus doesn’t matter, conviction does
Freedom within frameworks: see, pick, win, help, harvest
Mid-funnel decisions are the most important
The two fears that lead to bad decisions
To do this business well, you need courage

---

Timestamps:

(0:00) Intro

(1:01) Initial mindset as stewards

(4:30) The business of outliers

(6:27) Managing the inputs in venture

(12:11) Sourcing coverage goals

(17:57) Seeing the right companies

(22:36) Proprietary map of talent

(24:39) The impact of great engineers

(29:06) Picking winners with conviction

(36:26) Coaching asymmetry into picking

(43:16) Mentoring younger investors

(46:45) Frameworks on picking

(53:20) What it takes to win

(58:32) How to onboard with a founder

(1:02:59) Proudest board seats

(1:06:12) 2026 in the new roles

---

More on Jack:

https://www.altcap.com/

https://x.com/jaltma

---

https://linktr.ee/uncappedpod

Email: friends@uncappedpod.com

Uncapped #35 | Trae Stephens from Founders Fund

Wed, 03 Dec 2025 10:00:00 -0000

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 an integral part of the product team, leading the design and strategy for new product offerings.

Prior to Palantir, Trae worked as a computational linguist building enterprise solutions to Arabic/Persian name matching and data enrichment within the United States Intelligence community. He began his career working in the office of then Congressman Rob Portman and in the Political Affairs Office at the Embassy of Afghanistan in Washington, D.C. immediately following the installation of Hamid Karzai’s transitional government.

We covered:

Hard tech and the future of warfare
AI morality and “good quests”
How Anduril scales manufacturing
Founders Fund’s investing philosophy
Contrarianism and concentration
The ethics of autonomy and national defense

---

Timestamps:

(0:00) Intro

(0:35) Choosing good quests in the AI era

(7:35) Ethics behind solving certain problems

(11:29) Working with regulators

(16:54) What’s left to prove at Anduril

(18:32) Anduril, SpaceX, and Tesla at scale

(22:30) The future of warfare

(24:48) Juggling Anduril and Founders Fund

(29:07) A system that rewards going deep

(31:21) What’s made Founders Fund great

(37:30) The king-making strategy in VC

(40:26) Concentrating in the winners

(43:55) Where there’s alpha in the market

(47:22) Theological revival in traditional faith

---

More on Jack:

https://www.altcap.com/

https://x.com/jaltma

---

https://linktr.ee/uncappedpod

Email: friends@uncappedpod.com

Uncapped #34 | Mel Williams from TrueBridge

Tue, 25 Nov 2025 10:00:00 -0000

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 manage over $2 billion of endowment capital for the University of North Carolina.

We covered:

Investing in frothy markets
Doubling down on winners
Seed vs multi-stage
Picking managers

---

Timestamps:

(0:00) Intro

(1:10) AI valuations and a frothy market

(4:35) Long term market risks

(7:18) Should VC funds keep getting bigger?

(9:37) 10% of the market is the signal

(14:08) Venture math debate

(18:05) Characteristics of great investors

(20:46) The case for seed stage firms

(23:09) Picking managers

(24:59) Big wins and big misses

(30:12) It’s hard to kill a good brand

(33:06) Building a concentrated portfolio

(36:53) Advice to young LPs

---

More on Jack:

https://www.altcap.com/

https://x.com/jaltma

---

https://linktr.ee/uncappedpod

Email: friends@uncappedpod.com

Uncapped #33 | Vlad Tenev from Robinhood

Thu, 20 Nov 2025 10:00:00 -0000

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 to E-Trade to now Robinhood. Vlad delves into the launch of Robinhood, the impact of the global financial crisis, and how mobile and high-frequency trading have transformed finance. The conversation explores the rise and success of prediction markets, the importance of engaging younger generations, and how AI is enhancing the future of trading.

---

Timestamps:

(0:00) Intro

(00:27) History of online brokers

(4:15) The rise of Robinhood

(9:15) Changing sentiment among generations

(14:18) Incentive alignment with customers

(18:47) The emergence of prediction markets

(25:50) Economic value vs entertainment

(28:26) Growing degree of risk taking

(35:21) Tokenization and private markets

(39:33) The impact of AI on Robinhood

(43:35) What excites Vlad about AI

(46:59) Reflections on being a founder

---

More on Jack:

https://www.altcap.com/

https://x.com/jaltma

---

https://linktr.ee/uncappedpod

Email: friends@uncappedpod.com

Uncapped #32 | Kyle Vogt from The Bot Company

Wed, 12 Nov 2025 10:00:00 -0000

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 into everyday life.

A few highlights:

Labs beginning to see their ChatGPT moment
Most robots will be specialized, not humanoids
Robots will be cooking steaks in less than 5 yrs
Indefinitely operating with less than 100 people
Running a marathon on every continent in 81+ hrs

---

Timestamps:

(0:00) Introduction

(0:34) Why robotics is suddenly booming

(1:48) AI unlocking the next wave

(3:31) Special-purpose vs generalized

(5:32) Designing robots people actually use

(9:00) Building for scale, impact, and affordability

(12:17) The myth of the humanoid robot

(15:04) Trust, safety, and privacy in your home

(17:51) The data powering robotics intelligence

(21:01) Why Kyle keeps starting hard companies

(22:32) The 100-person rule and elite teams

(26:10) How to move fast and actually ship

(27:28) What home robotics will do first

(35:05) Home security applications

(37:07) Robots should elevate our standard of living

(38:41) Lessons from Tesla vs Waymo

(41:08) Thoughts on when to sell the company

(42:41) Running marathons on every continent

---

More on Jack:

https://www.altcap.com/

https://x.com/jaltma

---

https://linktr.ee/uncappedpod

Email: friends@uncappedpod.com

Uncapped #31 | Dylan Field from Figma

Wed, 05 Nov 2025 10:00:00 -0000

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 billion and its stock price more than tripled on its first trading day.

A few highlights:

Expanding a sleepy market
Merging of designers and product roles
Counter-narrative to polarizing CEOs
If models get better, we have to
Remembering Brat Summer

---

Timestamps:

(0:00) Intro

(0:37) The first 5 years of Figma

(5:14) Slow build vs AI gold rush

(13:01) The role of the human designer

(18:55) Small companies with $1B in revenue

(21:28) Expanding a sleepy market

(27:49) Leading with empathy as CEO

(32:51) Connecting with young people

(41:37) Getting stronger despite Adobe

(48:43) AI impacting Figma’s roadmap

(52:02) Final bastion of human designers

---

More on Jack:

https://www.altcap.com/

https://x.com/jaltma

---

https://linktr.ee/uncappedpod

Email: friends@uncappedpod.com

Uncapped #30 | Alex Pall from The Chainsmokers

Wed, 29 Oct 2025 09:00:00 -0000

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 including “Closer,” “Something Just Like This,” and “Don’t Let Me Down.” We also explored the creative process at the highest level and how Alex’s experience in music influences the way he approaches venture investing.

---

Timestamps:

(0:00) Intro

(1:04) Stories behind the songs

(4:58) Coldplay collaboration

(9:57) Creating Closer

(13:25) Dependencies vs creative fuel

(18:09) Letting songs be promiscuous

(19:45) How “Don’t Let Me Down” happened

(22:57) Art vs playing the favorites

(26:18) Balancing music and business

(29:49) Albums telling stories

(35:42) Tension behind growth as an artist

(39:28) Inspiration drives creativity

(41:20) AIs impact on music

(44:34) Outlier talent

(47:22) Building a venture firm

(54:46) Experiencing elite circles

(1:01:17) Importance of momentum

---

More on Jack:

https://www.altcap.com/

https://x.com/jaltma

---

https://linktr.ee/uncappedpod

Email: friends@uncappedpod.com

Uncapped #29 | Thomas Laffont from Coatue

Wed, 22 Oct 2025 09:00:00 -0000

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 decades, including Applied Intuition, Canva, Databricks, Figma and Rippling. Thomas began his career at the Creative Arts Agency, where he represented artists in film and television.

A few highlights:

The system of record being over
Wanting to be a founder’s second call
Investing with a wide aperture
Tom Cruise validating star quality
Working with family

---

Timestamps:

(0:00) Intro

(0:25) Making sense of the current cycle

(5:31) Investing from inception through IPO

(10:36) Depreciation of the system of record

(14:04) Value beyond databases

(18:46) Winning strategies in venture

(23:43) Operating at early-stage

(28:56) Navigating investing conflicts

(34:29) Wide aperture lens of investing

(36:45) Star quality being a reality

(40:30) Firm strategy and decision making

(48:25) Everything that’s great about golf

(54:34) Working with family

(57:20) Advice to young professionals

---

More on Jack:

https://www.altcap.com/

https://x.com/jaltma

---

https://linktr.ee/uncappedpod

Email: friends@uncappedpod.com

Uncapped #28 | Roelof Botha from Sequoia

Wed, 15 Oct 2025 09:00:00 -0000

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 Sequoia, Roelof was the CFO of PayPal and led the company’s IPO at the age of 28, and later through its acquisition by eBay.

We covered:

Paranoia that drives success
Venture not being an asset class
Full contact conversations
Cost being the secret to Silicon Valley
The next trillion dollar markets

---

Timestamps:

(0:00) Intro

(0:52) Becoming the steward

(5:16) Keeping healthy paranoia

(9:26) Drivers of joy as a leader

(11:17) Current venture playing field

(13:38) Venture is not an asset class

(18:50) Advice to new managers

(19:47) Decision making at Sequoia

(30:11) Investing across stages

(37:12) Component of cost

(46:57) Conflicting investments

(50:48) The next trillion dollar markets

(59:30) Team building

---

More on Jack:

https://www.altcap.com/

https://x.com/jaltma

---

https://linktr.ee/uncappedpod

Email: friends@uncappedpod.com

---

This episode is presented for informational purposes only and does not constitute investment advice or an offer to sell, or a solicitation of an offer to buy, any securities. The discussion herein similarly does not constitute a solicitation with respect to any Sequoia fund or an offer of investment advisory services. Investments identified herein are discussed solely for illustrative purposes and there is no guarantee that current or future investments of Sequoia will be similar in quality or kind.

Uncapped #27 | Vince Hankes from Thrive Capital

Wed, 08 Oct 2025 09:00:00 -0000

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
Buying Carvana at the bottom
The value of compounding
What matters most to Thrive

---

Timestamps:

(0:00) Intro

(0:50) The evolution of Thrive

(4:22) Instagram, Github, and Stripe

(7:57) Qualitative, then quantitative

(9:39) Writing massive checks

(16:48) Winning strategies in venture

(25:58) Buying Carvana at the bottom

(32:50) Managing conflicts

(36:13) AI’s impact on the market

(42:25) East meets West Coast investors

(45:19) Vertical specific workspaces

(49:53) Scale and timing of robotics

(51:31) OpenAI vs everything else

(55:59) What matters most for Thrive

---

More on Jack:

https://www.altcap.com/

https://x.com/jaltma

---

https://linktr.ee/uncappedpod

Email: friends@uncappedpod.com

---

This episode is presented for informational purposes only and does not constitute investment advice or an offer to sell, or a solicitation of an offer to buy, any securities. The discussion herein similarly does not constitute a solicitation with respect to any Thrive fund or an offer of investment advisory services. Investments identified herein are discussed solely for illustrative purposes and there is no guarantee that current or future investments of Thrive will be similar in quality or kind.

Uncapped #26 | Ali Rowghani

Wed, 01 Oct 2025 09:00:00 -0000

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 Director of Y Combinator’s Continuity Fund where he led investments in DoorDash, Stripe, Coinbase, Zapier, among many others. Ali has also invested as an early angel in several breakout AI companies, including Mercor, Decagon, and Cursor. He’s seen the arc from inception to IPO many times and recognizes what separates winning startups from the pack.

We covered:

Pixar’s golden age
Exceptional leadership
Working with Steve Jobs
Twitter going from $0 to $2B
Operating beliefs in venture

---

Timestamps:

(0:00) Intro

(0:53) Pixar’s miracle factory

(6:28) Working with Steve Jobs

(13:23) Ed Catmull and John Lasseter

(16:28) Crazy years at Twitter

(18:30) Getting monetization right

(19:56) Learnings in hindsight

(22:37) Elon Musk observations

(24:03) Beginning of YC’s growth fund

(29:31) Between pre and post traction

(33:23) The second job of a CEO

(34:35) First Harmonic

(35:31) Beliefs in venture

---

More on Jack:

https://www.altcap.com/

https://x.com/jaltma

---

Link to Ali’s referenced blog post:

https://www.ycombinator.com/library/3k-the-second-job-of-a-startup-ceo

---

https://linktr.ee/uncappedpod

Email: friends@uncappedpod.com

Uncapped #25 | Lulu Cheng Meservey

Wed, 24 Sep 2025 09:00:00 -0000

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.

Lulu writes an acclaimed newsletter called Flack, where she proposes her new playbook for communications and shares tactical advice for how to help win over the people who matter, without wasting time or inducing cringe.

A few memorable moments:

Aura is code for good communicator
People like to have assumptions for the level of celebration you deserve
The correct version of this company has him in it
Words that mean the same thing aren’t perceived the same way
Comms is the last thing to be uniquely human

---

Timestamps:

(0:00) Intro

(0:50) Comms having a moment

(3:43) Breaking through the noise

(6:30) What makes a great story

(9:58) Creating story arcs

(17:29) Flow and stock

(20:29) All press is good press

(23:25) Leaning into authenticity

(28:10) Word choice

(35:09) Impact on recruiting

(42:48) The business of comms

(45:48) Comms predictions

(48:18) Tech & media relationship

---

More on Jack:

https://www.altcap.com/

https://x.com/jaltma

---

https://linktr.ee/uncappedpod

Email: friends@uncappedpod.com

Uncapped #24 | Balaji Srinivasan

Thu, 18 Sep 2025 20:11:00 -0000

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 Labs, Benchling, and Polymarket to name a few. Balaji also led the launch of USDC as Coinbase CTO, and was an early investor in many important crypto protocols including Bitcoin, Ethereum, and Solana among others.

In this conversation, we discuss the evolving political landscape, emphasizing the disruptions caused by technology and the internet. Balaji outlines the four factions in the current political climate: the internet, Blue America, Red America, and China. We also explore the implications of tariffs, the rise of AI, and the future of network states.

---

Timestamps:

(0:00) Intro

(0:19) The Network School

(1:24) Mapping the political landscape

(3:38) Tech and the media

(6:19) China and the trade war

(11:32) Tariffs and economic strategy

(24:30) Global economic shifts

(27:41) Rise of the global anti-woke coalition

(31:11) Unholy alliances that might form

(37:18) Class warfare instead of race warfare

(41:21) The answer may not be in America

(46:56) The Network State

---

More on Jack:

https://x.com/jaltma

https://www.altcap.com/

---

https://linktr.ee/uncappedpod

Email: friends@uncappedpod.com

Uncapped #23 | Martin Casado from a16z

Wed, 03 Sep 2025 09:00:00 -0000

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 run-rate business. Martin started his career at Lawrence Livermore National Laboratory where he worked on large-scale simulations for the Department of Defense before moving over to work with the intelligence community on networking and cybersecurity.

We covered:

What necessitates specialization
The conflicts dynamic
Infra vs app companies
Importance of open source
The only sin in VC

---

Timestamps:

(0:00) Intro

(0:27) Importance of media for VC

(3:50) Evolution of a16z

(7:00) Specialization

(10:32) Value of distribution

(13:16) Staying power in infra

(19:49) The conflicts dynamic

(26:32) State of play in AI

(30:48) The future of coding

(34:58) Significance of open source

(39:48) Marc Andreessen’s leadership

(44:02) The only sin in VC

(48:37) Scaling a lot of board seats

---

More on Jack:

https://www.altcap.com/

https://x.com/jaltma

---

https://linktr.ee/uncappedpod

Email: friends@uncappedpod.com

Uncapped #22 | Greg Rosen from BoxGroup

Wed, 20 Aug 2025 09:00:00 -0000

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 venture fund in New York City.

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.

We covered:

Being collaborative at scale
Avoiding adverse selection
Getting to a yes instead of no
Venture calendar audits
Running the right strategy

---

Timestamps:

(0:00) Intro

(0:47) The collaborative venture model

(5:47) Adverse selection vs coverage

(11:59) How to see a ton of companies

(14:44) Getting to founders early

(21:10) Helping teammates get to a yes

(23:25) Why there aren’t more BoxGroups

(27:57) What’s learnable about picking

(31:46) Calendar auditing

(34:39) Focusing on where you’re outlier

(37:25) Depth vs breadth of network

(41:03) The future of code

(44:00) Brain computers

---

More on Jack:

https://www.altcap.com/

https://x.com/jaltma

---

https://linktr.ee/uncappedpod

Email: friends@uncappedpod.com

Uncapped #21 | Brian Armstrong from Coinbase

Wed, 13 Aug 2025 09:00:00 -0000

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 on a mission to significantly extend human lifespan that recently raised a $130M Series B led by Kleiner Perkins and angels including John and Patrick Collison, Elad Gil, and Joshua Kushner, among others.

We covered:

Working with the government
When to jump to the hot new thing
Choosing what frontiers to prioritize
The inner game of being contrarian

---

Timestamps:

(0:00) Intro

(0:26) Becoming the everything chain

(4:20) Story behind the GENIUS Act

(5:33) Working with regulators

(10:45) The future of crypto and the government

(17:10) When to jump to the hot new thing

(23:03) Choosing what frontiers to prioritize

(29:59) Brain-computer interface tech

(34:48) Inside the mind of a contrarian

(43:52) Creating a sustainable lifestyle

---

More on Jack:

https://www.altcap.com/

https://x.com/jaltma

---

https://linktr.ee/uncappedpod

Email: friends@uncappedpod.com

Uncapped #20 | Guillermo Rauch from Vercel

Wed, 06 Aug 2025 09:00:00 -0000

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 at the age of ten, and has been a passionate contributor to the open-source community ever since. He is the mind behind foundational JavaScript frameworks like Next.js and Socket.io, and has built tools that power some of the internet’s most innovative products, including Midjourney, Grok, and Notion.

We covered:

Vercel’s early insights
State of affairs for codegen
Implications of AI for developers
Skills of the future
Product building taste

---

Timestamps:

(0:00) Intro

(0:28) Prequel to Vercel

(4:32) Vercel’s early insights

(8:13) State of affairs for codegen

(17:18) Codegen evolution

(19:37) Perceived vs realized productivity

(27:53) Fault attribution

(31:56) Internet being a house of cards

(35:33) When codegen will be exceptional

(40:18) What kids should be learning

(47:42) Chasing the dragon vs listening to customers

(50:46) The next internet

(51:58) Reverse engineering success

(55:50) Making it work as a dad and CEO

(58:14) Taste in building product

---

More on Jack:

https://www.altcap.com/

https://x.com/jaltma

---

https://linktr.ee/uncappedpod

Email: friends@uncappedpod.com

Uncapped #19 | Dwarkesh Patel

Wed, 30 Jul 2025 09:00:00 -0000

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 2024, he was included in TIME’s 100 most influential people in AI alongside the likes of Ilya Sutskever, Andrew Yao, and Albert Gu. Dwarkesh’s interviews span far beyond AI, his North Star being his curiosity and preparation.

We covered:

Digital minds leading huge companies
AI making us smarter vs rotting our brain
His approach to learning as his job
Best in class interview preparation

---

Timestamps:

(0:00) Intro

(0:23) Skepticism around the timing of AGI

(6:07) Confidence in AI researchers

(7:17) Future utility of superintelligence

(11:23) Impact of scaling digital minds

(15:41) Driven by increases in compute

(17:17) Is AI making us smarter?

(21:03) AI’s impact on biology

(23:54) Interests outside of AI

(26:18) Chronology of his interests

(31:10) His approach to learning

(33:43) New thinking on human evolution

(40:44) Learning and the media

(45:52) Podcasting success

(48:53) Best in class interview preparation

---

More on Jack:

https://www.altcap.com/

https://x.com/jaltma

---

https://linktr.ee/uncappedpod

Email: friends@uncappedpod.com

Uncapped #18 | Peter Fenton from Benchmark

Wed, 23 Jul 2025 09:00:00 -0000

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 public on the same day. More recent investments include Sierra, Ollama, ClickHouse, and Airtable. Peter is considered one of the most successful tech investors of our time and is an incredible person to learn from.

We covered:

Darwinism and Silicon Valley
Who wins as a result of AI
Embracing things that don’t scale
Sourcing and winning motions
Being a great board member

---

Timestamps:

(0:00) Intro

(0:23) Darwinism and Silicon Valley

(5:38) Silicon Valley vs everywhere else

(12:09) Highly adaptive ecosystems

(19:40) Who wins with AI

(26:22) Applying Darwinism to venture

(36:54) North Stars in venture

(42:22) Embracing things that don’t scale

(49:51) A young person’s game

(57:10) Sourcing methodologies

(1:07:50) Convincing founders to choose you

(1:10:56) Not a winner-take-all game

(1:13:35) Being a great board member

---

Uncapped #17 | Christina Cacioppo from Vanta

Wed, 16 Jul 2025 09:00:00 -0000

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 2 much.” Before founding Vanta in 2018, Christina was an investor at Union Square Ventures and helped bring Dropbox Paper to market as a product manager.

We covered:

Operating in a competitive market
Fundraising frameworks
Recruiting as you scale
What should be AI-ified internally
The inner game of being a founder

---

Timestamps:

(0:00) Intro

(0:25) Staying under the radar

(3:29) No referees in capitalism

(5:20) Shipping velocity

(6:43) Mindset on competition

(8:09) Structuring a GTM approach

(10:25) Fundraising strategies

(16:36) VCs being “helpful”

(21:57) Recruiting as you scale

(28:33) Adapting to the AI era

(32:09) What should be AI-ified

(38:18) Mental game of being a founder

---

Uncapped #16 | Mamoon Hamid from Kleiner Perkins

Wed, 09 Jul 2025 09:00:00 -0000

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 eventually became Partner. Mamoon came to Silicon Valley in 1997 to join Xilinx, a Kleiner Perkins company, where he spent six years, initially as an engineer and later in product and marketing roles.

We covered:

Comparing innovation cycles
AI’s $60 trillion opportunity
The future of robotics
Reigniting a storied firm
Investing in Box, Slack, and Figma

---

Timestamps:

(0:00) Intro

(0:29) The dot-com bubble

(7:12) Web 2.0 and cloud

(16:03) Early days of mobile

(17:51) AI’s $60 trillion opportunity

(21:48) Where to invest in AI

(28:39) The future of robotics

(32:35) Reigniting a storied firm

(41:36) Growing vs recruiting talent

(46:42) Win rate aspirations

(49:16) Investing in Box, Slack, and Figma

(54:36) Assessing founders

(57:14) Kleiner Perkins’ strategy

(1:00:52) Family and faith

---

Uncapped #15 | Vinod Khosla from Khosla Ventures

Tue, 01 Jul 2025 09:00:00 -0000

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. He later went on to co-found Sun Microsystems in 1982, serving as its first chairman and CEO. After joining Kleiner Perkins Caulfield and Byers (KPCB), Vinod intubated the idea for Juniper Networks to take on Cisco System’s dominance of the router market, a company that would give KPCB a 2,500x return on its early investment.

Vinod is driven by the belief that technology is a positive force multiplier to accelerate societal reinvention in food, health, climate, energy transportation, education, housing finance, media, retail and entertainment for billions around the globe. His greatest passion lies in being a mentor to entrepreneurs who are building companies to tackle society’s largest challenges.

We covered:

Uncanny ability to predict the future
AI generating a new era of abundance
Future of energy, transportation and medicine
Increasing the consequence of success
Khosla’s approach to venture
Instigating change

---

Timestamps:

(0:00) Intro

(0:26) Craziness of the current cycle

(5:54) Predictions of the future

(9:35) Role of humans with AI

(16:20) Potential AI dystopia

(23:18) Investing in OpenAI

(33:21) Robotics being next

(39:53) Incumbents not innovating

(42:29) Mindset around risk

(44:14) Bull case for energy

(50:22) New transportation

(54:18) Future of medicine

(1:03:00) A different type of enjoyment

(1:05:40) Approaches to venture

(1:12:13) Khosla’s operating principles

(1:16:17) Staying energized

---

Linktree: https://linktr.ee/uncappedpod

Twitter: https://x.com/jaltma

Email: friends@uncappedpod.com

Uncapped #14 | Dan Feder from the University of Michigan

Tue, 24 Jun 2025 09:00:00 -0000

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 the Princeton University Investment Company where he led the development of Princeton’s global private equity and venture capital portfolio. Dan has also served as the Managing Director of Private Markets for the Sequoia Capital Heritage Fund (an endowment-style investment fund sponsored by Sequoia Capital) and as a Senior Investment Manager in the endowment services area at TIAA-CREF.

We covered:

Endowment portfolio construction
Incentive structures in LP land
Backing conflicting strategies
UMich’s framework to investing
Picking individuals vs firms

---

Timestamps:

(0:00) Intro

(0:40) Becoming an endowment manager

(2:59) Constructing an endowment’s portfolio

(9:10) Risk-based investing vs uncertainty

(13:07) Incentive structures in LP land

(16:28) Team construction

(22:26) Backing strategies that are at odds

(26:06) Why LPs invest in venture

(27:38) UMich framework to investing

(32:29) Picking individuals vs firms

(36:40) Big vs small funds

(40:48) How to pick fund managers

(45:41) Herd mentality in LP land

---

Linktree: https://linktr.ee/uncappedpod

Twitter: https://x.com/jaltma

Email: friends@uncappedpod.com

Uncapped #13 | Sam Altman from OpenAI

Tue, 17 Jun 2025 19:46:00 -0000

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
Plenty of brotherly banter

---

Timestamps:

(0:00) Intro

(0:48) AI discovering new science

(5:40) Humanoids are the future

(8:27) A world with superintelligence

(11:20) Medium-term predictions

(15:37) Potential OpenAI apparatus

(19:01) Supply chain implications

(21:51) Meta / Scale AI news

(29:04) Personal reflections

---

Linktree: https://linktr.ee/uncappedpod

Twitter: https://x.com/jaltma

Email: friends@uncappedpod.com

Uncapped #12 | Marc Andreessen from a16z

Wed, 11 Jun 2025 09:00:00 -0000

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 Mosaic internet browser and co-founded Netscape, which later sold to AOL for $4.2 billion. He also co-founded Loudcloud, which as Opsware, sold to Hewlett-Packard for $1.6 billion. He later served on the board of Hewlett-Packard from 2008 to 2018.

Marc serves on the board of the following Andreessen Horowitz portfolio companies: Applied Intuition, Carta, Coinbase, Dialpad, Flow, Golden, Honor, OpenGov, Samsara, Simple Things, and TipTop Labs. He is also on the board of Meta.

We covered:

Evolution of the venture playbook
Small vs large funds
Current AI landscape
Politics and Silicon Valley
Tech and the media

A few highlights:

Optimizing for the maximum amount of power
Conflicts being the reason a16z isn’t even larger
The middle is dead; you’re either Gucci or Walmart
Only 8 companies in the S&P 500 are innovating
We’ve lived in an era of intense preference falsification
AI and machines making the ultimate decision

---

Timestamps:

(0:00) Intro

(0:27) Evolution of the venture playbook

(15:54) Small vs large funds

(29:10) Becoming a top tier firm

(35:33) Limiting factors to building big companies

(40:11) Investing in AI

(50:02) Developing investors

(59:06) AI going wrong

(1:09:20) Politics and Silicon Valley

(1:11:39) Tech and the media

(1:23:22) Preference falsification

(1:31:10) Career advice

(1:34:07) Huberman “beef”

(1:38:21) Question from X

---

Uncapped #11 | Jordan Bramble from Antares

Thu, 29 May 2025 09:00:00 -0000

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 on earth and in space. Unlike grid-scale reactors, these use cases primarily favor kilowatt-scale systems. This focus on non-commodity energy applications with smaller scale reactors will enable Antares to develop its first deployments on faster timelines with less research and development and capitalization risk. Antares also partners with commercial companies in extractive industries, edge computing, and space power, in turn bringing the benefits of commercial scale back to the DOD.

We covered:

History of nuclear
Demand for nuclear
Small modular reactors
Government collaboration
Building in hard tech
Scaling nuclear reactors

A few highlights:

First nuclear reactor built under UChicago’s football field
A nuclear powered airplane that could fly indefinitely
Net zero not being possible without nuclear
Powering the AI demand for data centers
The Golden Dome and lasers in space
Working back from the mission effect
Interdisciplinary problems attracting talent

---

Timestamps:

(0:00) Intro

(0:22) History of nuclear

(6:50) Radical decline in development

(10:51) Current appetite for funding

(20:53) Small modular reactors

(30:11) Selling to defense

(34:30) LA becoming a hard tech hub

(37:13) Fostering a culture in hard tech

(43:42) How to scale nuclear reactors

---

Uncapped #10 | David Tisch from BoxGroup

Thu, 22 May 2025 09:00:00 -0000

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 is the Chairman of GoodDog, a marketplace to find pets online. He is the co-founder of TechStars NYC and serves on the board of Friends of Hudson River Park.

We covered:

Scaling something deemed unscalable
Art of being collaborative
Taste not being teachable
VC help being overrated
Building a NYC brand

---

Timestamps:

(0:00) Intro

(0:27) Scaling a collaborative fund

(8:23) Stack ranking portfolios

(11:29) Investing at seed

(17:29) Hiring for taste

(22:30) The art of being collaborative

(29:03) VC help is overrated

(41:38) Why VCs pass on companies

(48:11) Building a brand in NYC

(55:02) North Stars in early-stage investing

---

Linktree: https://linktr.ee/uncappedpod

Twitter: https://x.com/jaltma

Email: friends@uncappedpod.com

Uncapped #9 | Qasar Younis from Applied Intuition

Thu, 15 May 2025 09:00:00 -0000

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 critical role in both the commercial and defense sectors.

Previously, Qasar was a Partner and COO of Y Combinator, the renowned startup accelerator that has invested in companies like Airbnb, Coinbase, Cruise, DoorDash, Stripe, among others. Prior to Y Combinator, Qasar founded a technology firm, which was later acquired by Google, and worked as an automotive engineer at General Motors and Bosch. Younis has a bachelor’s degree in mechanical engineering from Kettering University (formerly known as General Motors Institute) and an MBA from Harvard Business School.

We covered:

Radical pragmatism
Roots of the automotive industry
Complexities of being dual use
Fostering an intrinsically contrarian culture
Evolving with your work

---

Timestamps:

(0:00) Intro

(0:31) Psychology of starting a company

(17:04) Love for the automotive industry

(22:54) Autonomous vehicle landscape

(25:45) Deep partnership with customers

(28:49) Complexities of being dual use

(34:44) Culture being intrinsically contrarian

(40:01) Gen AI and humanoid robotics

(42:28) More noise than signal in investing

(44:14) Evolving with your work

(47:43) Companies working is a state in time

---

Linktree: https://linktr.ee/uncappedpod

Twitter: https://x.com/jaltma

Email: friends@uncappedpod.com

Uncapped #8 | Josh Kopelman from First Round Capital

Thu, 01 May 2025 09:00:00 -0000

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 First Round’s inception in 2004, Josh has invested in 500+ startups and has frequently made the Forbes “Midas List” which ranks the top 100 tech investors.

Josh has been a founder three times (four if you include founding First Round). In 1992, while in college, he co-founded Infonautics Corporation – and took it public on NASDAQ in 1996. Josh co-founded Half.com in 1999 and led it to become one of the largest sellers of used books, movies and music in the world. Half.com was acquired by eBay in 2000, where Josh remained for three years. In late 2003, Josh helped to found TurnTide, an anti-spam company that created the world’s first anti-spam router. TurnTide was acquired by Symantec just six months later.

We covered:

His “Venture Arrogance Score”
The role of relevance in venture
Making money in disequilibrium
Overlooking margin superiority
Decision-making as a product

---

Timestamps:

(0:00) Intro

(0:25) Current landscape

(4:39) Venture Arrogance Score

(10:49) Comparing fund models

(14:24) The role of relevance in venture

(21:03) Small funds vs large funds

(26:36) Making money in disequilibrium

(33:57) Overlooking margin superiority

(43:17) First Round’s strategy

(49:02) Operating like a company

(56:49) Future of First Round

---

Linktree: https://linktr.ee/uncappedpod

Twitter: https://x.com/jaltma

Email: friends@uncappedpod.com

Uncapped #7 | Garry Tan from Y Combinator

Thu, 17 Apr 2025 09:00:00 -0000

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 earliest in Coinbase and Instacart. Before that, Garry was a partner at Y Combinator where he invested in and directly worked with over 700 companies at the earliest stage. He previously co-founded Posterous and helped build it to a world-class website used by millions (acquired by Twitter).

Garry is a builder at heart.

We covered:

Running YC like a founder
Advice for founders
Picking winners
What changes because of AI
YC being the “YC of hard tech”
Public service

---

Timestamps:

(0:00) Intro

(0:25) Running YC like a founder

(6:25) Focusing on growth and prosperity

(12:40) Incredible pick rate

(14:34) Role of the Group Partner

(19:21) Lean vs fat startups

(20:53) Archetypes of special founders

(25:18) Rule changes because of AI

(33:00) YC being the “YC of hard tech”

(37:40) Community and political involvement

---

Linktree: https://linktr.ee/uncappedpod

Twitter: https://x.com/jaltma

Email: friends@uncappedpod.com

Uncapped #6 | Elad Gil

Thu, 10 Apr 2025 09:00:00 -0000

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, including Airbnb, Coinbase, Figma, Instacart, and Stripe. He's also invested in Harvey, Mistral, Perplexity, Pika, and other leading AI startups.

Elad is also author of the High Growth Handbook and is excited to be working on his next book focused on how to scale during the zero to one phase of a startup’s journey.

We covered:

Optimizing for market need and optionality
Recipes for long career arcs
Getting more leverage on time
Investing outside of AI
Value in getting the theme right

---

Timestamps:

(0:00) Intro

(0:50) Shamelessness mindset

(4:16) Optimizing for market need

(5:55) Cultivating optionality

(8:29) Characteristics of people with long career arcs

(9:54) What to optimize for early in a career

(22:20) Different phases of your life

(25:20) Aspiring to do things that are useful

(26:33) Pivot points in careers

(31:16) Becoming great investors

(33:28) Getting more leverage on time

(36:57) Investing outside of AI

(40:58) Getting the theme right means more

(47:01) Elad’s new book

---

Linktree: https://linktr.ee/uncappedpod

Twitter: https://x.com/jaltma

Email: friends@uncappedpod.com

Uncapped #5 | Sarah Guo from Conviction

Thu, 03 Apr 2025 09:00:00 -0000

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 Greylock Partners. Sarah co-hosts a podcast with Elad Gil called No Priors where they discuss the AI revolution.

We covered:

Compounding qualities of enduring firms
Brand building in the current market
Taking risk by having an opinion
Learnings from her time at Greylock
AI discourse compared to previous cycles

---

Timestamps:

(0:00) Intro

(0:11) What a VC firm is at its core

(2:27) Compounding qualities of enduring firms

(6:44) Intentionality behind building Conviction’s brand

(13:01) Correlation or causation between brands and returns

(16:33) Shape of the current VC market

(27:15) Learnings from experience at Greylock

(32:06) Market vs founder driven

(33:55) AI conversation shifting from inputs to outputs

(36:28) More billion dollar companies than ever before

(42:44) Agency being the last human resource

(44:40) Important skills for kids to learn

---

Linktree: https://linktr.ee/uncappedpod

Twitter: https://x.com/jaltma

Email: friends@uncappedpod.com

Uncapped #4 | Adam Guild from Owner

Tue, 01 Apr 2025 09:00:00 -0000

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 career.

He tracks his nutrition, exercise, time, and sleep to an extreme degree so he can show up to work every day as strong as possible. He goes to extreme lengths to recruit the best talent. He is equal parts hungry to learn from everyone around him, but courageous in making his own unconventional decisions.

I think he’s one of the most under-known founders right now, but I think that will soon change.

Hope you enjoy watching this.

---

Timestamps:

(0:00) Intro

(0:07) Inside the mind of a young founder

(6:36) Boldly purchasing Owner’s domain

(9:34) Listening to others vs being instinctual

(14:12) Decision making as a CEO

(16:43) Fostering a culture while scaling

(18:34) High impact interview questions

(21:29) Recruiting the best talent

(29:50) Never missing an investor update

(34:16) Getting canceled on Twitter

(42:41) Startups are the Olympics of business

---

Linktree: https://linktr.ee/uncappedpod

Twitter: https://x.com/jaltma

Email: friends@uncappedpod.com

Uncapped #3 | Aaron Levie from Box

Tue, 25 Mar 2025 09:00:00 -0000

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.

---

Timestamps:

(0:00) Intro

(0:10) Excitement in AI

(6:50) Startups vs incumbents

(15:04) Pricing agents

(17:42) AI over or under hyped

(19:17) Being first to cloud

(24:55) Staying motivated

(28:29) Shifting political landscape

---

Linktree: https://linktr.ee/uncappedpod

Twitter: https://x.com/jaltma

Email: friends@uncappedpod.com

Uncapped #2 | Keith Rabois from Khosla Ventures

Thu, 20 Mar 2025 09:00:00 -0000

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 investments in YouTube, Airbnb, Palantir, Lyft, Udemy, and Eventbrite. Keith started his career in leadership roles at PayPal and LinkedIn before becoming COO of Square.

---

We covered:

(0:00) Competing where there isn’t competition

(2:29) Traits of top decile founders

(7:16) Picking people

(9:57) Being a consigliere

(13:54) Decision making

(21:51) Acting when confident

(26:43) Advantages of a large fund

(31:06) Raising in a frothy market

(35:47) Tech and the government

(43:21) Being vocal on politics

(46:47) Valuing board members

(52:24) Former operators vs career investors

---

Linktree: https://linktr.ee/uncappedpod

Twitter: https://x.com/jaltma

Email: friends@uncappedpod.com

Uncapped #1 | Shaun Maguire from Sequoia

Thu, 13 Mar 2025 09:00:00 -0000

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.

---

We covered:

(0:00) Speaking his mind in public

(13:38) Trust and the media

(24:27) Tech’s political flip

(29:27) Investing in hard tech vs. software

(45:27) Thinking with a beginner's mind

(52:30) Fulfillment in investing

(59:33) Investing in outlier people

---

Linktree: https://linktr.ee/uncappedpod

Twitter: https://x.com/jaltma

Email: friends@uncappedpod.com