Uncapped #42 | Bret Taylor from Sierra

More from Uncapped with Jack Altman All episodes →

1. 

   16 Apr 2026 · 35 min

   Uncapped #47 | Max Mullen from Instacart

   Max Mullen is the co-founder of Instacart and an active investor having invested in 100+ companies including Gumloop, Mercury, Owner among others. He also runs a founder community in San Francisco called Workshop. We discussed the full arc of building Instacart from a contrarian idea that investors rejected to a $10B consumer marketplace. Max highlighted the scrappy early days, marketplace product-market fit, and key inflection points like retailer partnerships and the Amazon–Whole Foods moment. We also explored what makes great consumer founders, why the best ideas look wrong at first, and…

2. 

   1 Apr 2026 · 50 min

   Uncapped #46 | Brad Lightcap from OpenAI

   Brad Lightcap serves as OpenAI's COO, overseeing its business, operations, and strategic partnerships across Research, Applied AI, and go-to-market. He also manages the OpenAI Startup Fund. Previously, Brad was part of Y Combinator Continuity and led finance and operations initiatives at Dropbox. We discussed the shift from chat-based AI to agents that can take action, and what that means for software and the broader economy. We also covered how these systems are being built and deployed, how tools like Codex are changing how work gets done, and what this next phase of AI unlocks for…

3. 

   25 Mar 2026 · 41 min

   Uncapped #45 | Ron Conway from SV Angel

   Ron Conway is the Founder and a Managing Partner of SV Angel. He has been an active angel investor since the mid-90s and has received wide recognition for his role in the tech ecosystem. He has been included on Vanity Fair’s 100 most influential people in the Information Age, awarded Best Angel at the TechCrunch Crunchies Awards, and has been named on Forbes Magazine's Midas list of top “deal-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…

4. 

   12 Mar 2026 · 50 min

   Uncapped #44 | Max Junestrand from Legora

   At 23, with no legal background, Max Junestrand co-founded Legora to transform how lawyers work. Legora recently (March 2026) raised $550 million at a $5.55 billion valuation in a Series D funding round to accelerate its expansion across the United States. Over the past year, Legora has grown from 40 to 400 team members across the globe and the platform supports tens of thousands of lawyers each 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…

5. 

   3 Mar 2026 · 59 min

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

   In this episode, the team behind Y Combinator reflects on what has — and hasn’t — changed since the early days of YC, and how AI is reshaping what it means to be a founder. They discuss how they evaluate builders now, why execution still matters more than competition, and what YC is prioritizing as the startup landscape evolves. At its core, the mission remains the same: increase the number of 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…

6. 

   4 Feb 2026 · 57 min

   Uncapped #41 | The Benchmark Partnership

   In this episode, the Benchmark partnership explains why they’ve resisted scale, eliminated residual economics, and built an equal partnership designed to endure. We talk about what that choice enables – for founders, for decision-making, and for practicing venture as a craft rather than a factory. Peter Fenton is the longest-serving full-time general partner at Benchmark. Over the last two 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…

7. 

   21 Jan 2026 · 1 hr 5 min

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

   Vinod Khosla and Keith Rabois are Managing Directors at Khosla Ventures. Vinod is an entrepreneur, investor and technologist. In 2004, Vinod formed Khosla Ventures to focus on both for-profit and social impact investments that have included OpenAI, Stripe, DoorDash, Commonwealth Fusion Systems and many more. Vinod previously co-founded Daisy Systems, the first significant computer-aided design 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…

8. 

   14 Jan 2026 · 45 min

   Uncapped #39 | Daniele Perito from depthfirst

   Daniele Perito is Co-founder and Executive Chairman of depthfirst, an AI-native security platform that understands your code, business logic, and infrastructure to find real vulnerabilities, slash false positives, and give developers actionable fixes in their workflow. Daniele is also Co-founder and Board Member of Faire, where he previously served as Chief Data Officer and helped build the 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…

9. 

   9 Jan 2026 · 58 min

   Uncapped #38 | Ben Horowitz from a16z

   Ben Horowitz is a cofounder and general partner at the venture capital firm Andreessen Horowitz, a venture capital firm that manages $60 billion in assets under management. He is also the author of the New York Times bestsellers, The Hard Thing About Hard Things and What You Do Is Who You Are. Prior to a16z, Ben was cofounder and CEO of Opsware (formerly Loudcloud), which was acquired by Hewlett-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…

10. 

    16 Dec 2025 · 1 hr 23 min

    Uncapped #37 | Saam Motamedi from Greylock Partners

    Saam Motamedi is a General Partner at Greylock Partners working with enterprise software entrepreneurs at the seed and early stages who are focused on new opportunities in intelligent applications, cybersecurity, AI, and data infrastructure. In 2019 at just 26 years old, Saam became the Greylock’s youngest General Partner in its 54-year history – a remarkable achievement at an institution that had backed Airbnb, AppDynamics, Coinbase, Discord, Figma, Instagram, LinkedIn, among others. Saam’s portfolio spans 14+ companies with collective valuations exceeding $10 billion. Abnormal Security,…