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Uncapped | Benchmark Breakfast

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Conversations with people we admire about things we’re genuinely interested in. Uncapped and Benchmark Breakfast live here.

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  • 24 episodes
  • fortnightly
  • Avg 55 min
  • English

Episodes 24

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  • January 14 · 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 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 Daniele: https://depthfirst.com/ https://www.linkedin.com/in/danieleperito/ More on Jack: https://www.altcap.com/ https://x.com/jaltma --- https://linktr.ee/uncappedpod Email: friends@uncappedpod.com

  • January 9 · 57 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 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 Ben: https://a16z.com/ https://a16z.simplecast.com/ https://x.com/bhorowitz More on Jack: https://www.altcap.com/ https://x.com/jaltma --- https://linktr.ee/uncappedpod Email: friends@uncappedpod.com

  • Dec 16, 2025 · 1 hr 22 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, 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 Saam: https://greylock.com/ https://x.com/saammotamedi More on Jack: https://www.altcap.com/ https://x.com/jaltma --- https://linktr.ee/uncappedpod Email: friends@uncappedpod.com

  • Dec 9, 2025 · 1 hr 9 min

    Uncapped #36 | Pat Grady & Alfred Lin from Sequoia

    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 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 --- https://linktr.ee/uncappedpod Email: friends@uncappedpod.com

Showing 21–24 of 24 episodes