Uncapped with Jack Altman

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:

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

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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:

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

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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:

Durable components to great firms

Inside look at how Greylock operates

Cracking the code on incubations

Alpha in today’s venture strategies

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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:

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

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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]