Uncapped | Benchmark Breakfast

Kevin Hartz and Bennett Siegel are co-founders and GPs at A*, a five year old early-stage venture capital firm with $1B in AUM. A* has invested in companies like Notion, Cape, Whop, Paraform, Simile, Krea, Mercor, Watney Robotics, Andera and others.

Kevin is also the co-founder of Eventbrite (NYSE: EB) and co-founder and board member of Xoom, an online money transfer service that IPO’d in 2013 and later acquired by PayPal for $1.1B. Notable investments, primarily at the seed/early stages, include PayPal, Airbnb, Pinterest, Reddit, Anduril, and Palantir among others. Bennett was previously a partner at Coatue building out their venture capital business where he invested in earliest financing rounds for Ramp and Decagon, among other investments.

We discussed how AI is reshaping venture capital, software, and startup building – from the rise of younger founders and AI researcher-led companies to the growing pressure on traditional software businesses. We also covered the changing economics of seed investing, the influx of mega funds into early-stage venture, AI rollups, robotics, and why this may become the biggest technology boom yet.

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Timestamps:

(0:00) Intro

(0:25) The A* Capital story

(1:16) Why big funds went into seed

(7:50) The mother of all bubbles

(10:46) Why founders are getting younger

(13:00) Mapping talent, not markets

(16:31) The rise of AI researcher founders

(19:16) Why seed investing is so hard

(22:54) Concentration and venture returns

(27:34) The AI rollup craze

(31:15) AI vs traditional software

(33:15) Robotics and the future of AI

(35:39) What’s next for A* Capital

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Links:

https://x.com/kevinhartz

https://x.com/BennettSiegel

https://x.com/jaltma

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

https://uncappedpod.com/

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[email protected]

Tarek Mansour is the co-founder and CEO of Kalshi.

Kalshi is a regulated prediction market exchange valued at $22B in 2026 where people trade on the outcomes of real-world events – things like inflation prints, Fed decisions, elections, or weather events. Instead of betting against a house, users trade against each other in a market, and prices reflect the collective probability of an outcome happening.

Before starting Kalshi, Tarek worked as a quantitative trader at Goldman Sachs as a structured credit and equities analyst and at Citadel as a global macro trader. During his time at these firms, he realized a common thread: a lot of trading stemmed from an opinion on a future event.

We covered the idea behind prediction markets and how they offer a more direct way to trade on beliefs about the future. The conversation follows the long, difficult path to building a regulated exchange in the U.S., from early skepticism to ultimately winning a landmark legal battle. We also discuss how these markets can improve forecasting, enable new forms of hedging, and change how information gets priced.

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Timestamps:

(0:00) Intro

(0:23) Kalshi’s genesis

(5:05) Regulation-focused from inception

(11:06) Suing the government

(18:02) Gambling vs. financial markets

(20:58) Defining insider trading

(25:38) Incentive structure of the system

(32:40) Investing vs. trading

(35:31) Hedging use cases

(41:38) Scaling a lean team

(44:02) Defining Kalshi’s culture

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Links:

https://x.com/jaltma

https://x.com/mansourtarek_

https://kalshi.com/

https://uncappedpod.com/

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[email protected]

Max Mullen is the co-founder of Instacart and an active investor having invested in 100+ companies including Gumloop, Mercury, Owner among others. He also runs a founder community in San Francisco called Workshop.

We discussed the full arc of building Instacart from a contrarian idea that investors rejected to a $10B consumer marketplace. Max highlighted the scrappy early days, marketplace product-market fit, and key inflection points like retailer partnerships and the Amazon–Whole Foods moment. We also explored what makes great consumer founders, why the best ideas look wrong at first, and how to build and scale in “hard mode” markets. Finally, the conversation touched on investing, decision-making frameworks, and what it takes to win in consumer over the long term.

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Timestamps:

(0:00) Intro

(0:36) The inception of Instacart

(4:55) Finding product market fit

(7:20) Landing Trader Joe’s

(11:04) Big levers for growth

(13:36) Operationally complex businesses

(14:55) Amazon’s acquisition of Whole Foods

(17:50) COVID and Instacart’s IPO

(20:02) Prioritizing profitability

(23:21) Avoiding temptations

(24:59) The future of Instacart

(25:53) Investing in consumer

(28:21) Irrationally optimistic founders

(29:49) B2B vs consumer founders

(30:35) How to work with investors

(33:38) Building Workshop

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Links:

https://x.com/Max

https://x.com/jaltma

https://maxmullen.com/

https://uncappedpod.com/

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[email protected]

Brad Lightcap serves as OpenAI's COO, overseeing its business, operations, and strategic partnerships across Research, Applied AI, and go-to-market. He also manages the OpenAI Startup Fund. Previously, Brad was part of Y Combinator Continuity and led finance and operations initiatives at Dropbox.

We discussed the shift from chat-based AI to agents that can take action, and what that means for software and the broader economy. We also covered how these systems are being built and deployed, how tools like Codex are changing how work gets done, and what this next phase of AI unlocks for startups and incumbents alike.

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Timestamps:

(0:00) Intro

(0:39) The early days of OpenAI

(3:47) A research centric culture

(7:32) Post-ChatGPT chapters

(11:54) Sci-Fi future or good software

(15:26) AI’s impact on rural communities

(18:57) Codex and coding of the future

(24:04) Doing a lot of things at once

(27:55) What VCs should invest in

(35:43) The software sell off

(38:23) Using Codex over ChatGPT

(42:32) FDEs and Private Equity

(44:53) Working with Sam

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Links:

https://x.com/bradlightcap

https://x.com/jaltma

https://openai.com/

https://uncappedpod.com/

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[email protected]

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

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

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Timestamps:

(0:00) Intro

(1:50) From semiconductors to AI

(8:39) Two investments that changed everything

(11:46) Nonpassive angel investing

(14:57) Becoming a relationship broker

(18:00) Building authentic relationships

(24:48) Going deep with OpenAI and Airbnb

(29:19) Fighting for founders

(31:39) Remarkable returns at seed

(33:20) The state wealth tax

(37:17) Tech and politics

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Links:

https://x.com/RonConway

https://x.com/jaltma

https://svangel.com/

https://uncappedpod.com/

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[email protected]

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.

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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"

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Links:

https://x.com/MaxJunestrand

https://x.com/chetanp

https://x.com/jaltma

https://legora.com/

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https://uncappedpod.com/

[email protected]

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.

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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

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Links:

https://x.com/snowmaker

https://x.com/harjtaggar

https://x.com/garrytan

https://x.com/jaltma

https://www.ycombinator.com/

https://uncappedpod.com/

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[email protected]

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.

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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

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Links:

https://x.com/btaylor

https://x.com/jaltma

https://uncappedpod.com/

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Email: [email protected]

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.

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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

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Links:

https://x.com/peterfenton

https://x.com/ericvishria

https://x.com/chetanp

https://x.com/EverettRandle

https://x.com/jaltma

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https://uncappedpod.substack.com/

Email: [email protected]

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.

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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

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More on Vinod:

https://x.com/vkhosla

https://www.khoslaventures.com/team/vinod-khosla

More on Keith:

https://x.com/rabois

https://www.khoslaventures.com/team/keith-rabois

More on Jack:

https://www.altcap.com/

https://x.com/jaltma

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https://linktr.ee/uncappedpod

Email: [email protected]