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]

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:

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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

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More on Daniele:

https://depthfirst.com/

https://www.linkedin.com/in/danieleperito/

More on Jack:

https://www.altcap.com/

https://x.com/jaltma

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https://linktr.ee/uncappedpod

Email: [email protected]

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:

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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

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More on Ben:

https://a16z.com/

https://a16z.simplecast.com/

https://x.com/bhorowitz

More on Jack:

https://www.altcap.com/

https://x.com/jaltma

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https://linktr.ee/uncappedpod

Email: [email protected]

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:

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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

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More on Saam:

https://greylock.com/

https://x.com/saammotamedi

More on Jack:

https://www.altcap.com/

https://x.com/jaltma

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https://linktr.ee/uncappedpod

Email: [email protected]

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:

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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

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More on Pat & Alfred:

https://sequoiacap.com/

https://x.com/gradypb

https://x.com/Alfred_Lin

More on Jack:

https://www.altcap.com/

https://x.com/jaltma

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https://linktr.ee/uncappedpod

Email: [email protected]

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:

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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

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More on Trae:

https://foundersfund.com/

https://x.com/traestephens

More on Jack:

https://www.altcap.com/

https://x.com/jaltma

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https://linktr.ee/uncappedpod

Email: [email protected]

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:

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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

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More on Mel:

https://truebridgecapital.com/

https://truebridgecapital.com/team/mel-williams/

More on Jack:

https://www.altcap.com/

https://x.com/jaltma

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https://linktr.ee/uncappedpod

Email: [email protected]

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.

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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

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More on Vlad:

https://robinhood.com/us/en/

https://x.com/vladtenev

More on Jack:

https://www.altcap.com/

https://x.com/jaltma

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https://linktr.ee/uncappedpod

Email: [email protected]

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:

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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

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More on Kyle:

https://www.bot.co/

https://x.com/kvogt

More on Jack:

https://www.altcap.com/

https://x.com/jaltma

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https://linktr.ee/uncappedpod

Email: [email protected]