Greg Rosen is a Partner at BoxGroup. Greg was the first hire at BoxGroup outside of the founders, David Tisch and Adam Rothenberg. After moving to the West Coast to work with Benchmark and Bedrock, Greg rejoined BoxGroup and currently invests out of their San Francisco office. An engineer by training, Greg built iOS games in high school before dropping out of college at 19 to join Jim Pallotta's venture fund in New York City.

BoxGroup is an NYC-based seed stage venture capital firm that has invested in over 500 seed-stage startups over the last 15 years, including Plaid, Ro, Ramp, Clay, Scopely, Warp, Cursor, PillPack, Amplitude, Flatiron Health, Stripe, Warby Parker, Harry’s, Oscar, Flexport, Classpass, Vine, GroupMe, Airtable and more.

We covered:

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Timestamps:

(0:00) Intro

(0:47) The collaborative venture model

(5:47) Adverse selection vs coverage

(11:59) How to see a ton of companies

(14:44) Getting to founders early

(21:10) Helping teammates get to a yes

(23:25) Why there aren’t more BoxGroups

(27:57) What’s learnable about picking

(31:46) Calendar auditing

(34:39) Focusing on where you’re outlier

(37:25) Depth vs breadth of network

(41:03) The future of code

(44:00) Brain computers

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More on Greg:

https://www.boxgroup.com/

https://x.com/grosen

More on Jack:

https://www.altcap.com/

https://x.com/jaltma

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https://linktr.ee/uncappedpod

Email: [email protected]

Brian Armstrong is the co-founder and CEO of Coinbase, a leading cryptocurrency company that provides exchange, brokerage, and custody services to 100M+ verified users in over 100 countries. Founded in 2012, Coinbase went public in 2021 on the NASDAQ under the ticker COIN and as of August 2025 has a market cap of $83 billion. Brian is also the co-founder of New Limit, a longevity biotech company on a mission to significantly extend human lifespan that recently raised a $130M Series B led by Kleiner Perkins and angels including John and Patrick Collison, Elad Gil, and Joshua Kushner, among others.

We covered:

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Timestamps:

(0:00) Intro

(0:26) Becoming the everything chain

(4:20) Story behind the GENIUS Act

(5:33) Working with regulators

(10:45) The future of crypto and the government

(17:10) When to jump to the hot new thing

(23:03) Choosing what frontiers to prioritize

(29:59) Brain-computer interface tech

(34:48) Inside the mind of a contrarian

(43:52) Creating a sustainable lifestyle

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More on Brian:

https://www.coinbase.com/

https://www.newlimit.com/

https://x.com/brian_armstrong

More on Jack:

https://www.altcap.com/

https://x.com/jaltma

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https://linktr.ee/uncappedpod

Email: [email protected]

Guillermo Rauch is the founder and CEO of Vercel, creators of v0 which is one of the most popular AI app building tools that’s helping power the online presence of companies like Porsche, Under Armour and Nintendo. In May 2024, Vercel completed a $250M Series E at a $3.25B valuation and was recently named to the Forbes Cloud 100. Originally from Argentina, Guillermo became a self-taught developer at the age of ten, and has been a passionate contributor to the open-source community ever since. He is the mind behind foundational JavaScript frameworks like Next.js and Socket.io, and has built tools that power some of the internet’s most innovative products, including Midjourney, Grok, and Notion.

We covered:

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Timestamps:

(0:00) Intro

(0:28) Prequel to Vercel

(4:32) Vercel’s early insights

(8:13) State of affairs for codegen

(17:18) Codegen evolution

(19:37) Perceived vs realized productivity

(27:53) Fault attribution

(31:56) Internet being a house of cards

(35:33) When codegen will be exceptional

(40:18) What kids should be learning

(47:42) Chasing the dragon vs listening to customers

(50:46) The next internet

(51:58) Reverse engineering success

(55:50) Making it work as a dad and CEO

(58:14) Taste in building product

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More on Guillermo:

https://vercel.com/

https://x.com/rauchg

More on Jack:

https://www.altcap.com/

https://x.com/jaltma

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https://linktr.ee/uncappedpod

Email: [email protected]

In his early twenties, Dwarkesh Patel has become one of the leading podcasters with nearly 1 million YouTube subscribers excited to consume his deeply-researched interviews. Dwarkesh has caught the attention of influential figures such as Jeff Bezos, Noah Smith, Nat Friedman, and Tyler Cohen, who have all praised his interviews – the latter describing him as “highly rated but still underrated.” In 2024, he was included in TIME’s 100 most influential people in AI alongside the likes of Ilya Sutskever, Andrew Yao, and Albert Gu. Dwarkesh’s interviews span far beyond AI, his North Star being his curiosity and preparation. 

We covered:

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Timestamps:

(0:00) Intro

(0:23) Skepticism around the timing of AGI

(6:07) Confidence in AI researchers

(7:17) Future utility of superintelligence

(11:23) Impact of scaling digital minds

(15:41) Driven by increases in compute

(17:17) Is AI making us smarter?

(21:03) AI’s impact on biology

(23:54) Interests outside of AI

(26:18) Chronology of his interests

(31:10) His approach to learning

(33:43) New thinking on human evolution

(40:44) Learning and the media

(45:52) Podcasting success

(48:53) Best in class interview preparation

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More on Dwarkesh:

https://www.dwarkesh.com/

https://x.com/dwarkesh_sp

More on Jack:

https://www.altcap.com/

https://x.com/jaltma

---

https://linktr.ee/uncappedpod

Email: [email protected]

Peter Fenton is the longest-serving full-time partner at Benchmark, a renowned venture firm known for its artisanal approach and deep alignment with founders. Over the last two decades, Peter led investments in Twitter, Yelp, Elastic, Docker, Zuora, and many others. He also achieved one of the rarest feats in venture history in 2014 when two of his investments, Hortonworks and New Relic, went public on the same day. More recent investments include Sierra, Ollama, ClickHouse, and Airtable. Peter is considered one of the most successful tech investors of our time and is an incredible person to learn from.

We covered:

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Timestamps:

(0:00) Intro

(0:23) Darwinism and Silicon Valley

(5:38) Silicon Valley vs everywhere else

(12:09) Highly adaptive ecosystems

(19:40) Who wins with AI

(26:22) Applying Darwinism to venture

(36:54) North Stars in venture

(42:22) Embracing things that don’t scale

(49:51) A young person’s game

(57:10) Sourcing methodologies

(1:07:50) Convincing founders to choose you

(1:10:56) Not a winner-take-all game

(1:13:35) Being a great board member

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More on Benchmark and Peter:

https://www.benchmark.com/

https://x.com/peterfenton

More on Alt Capital and Jack:

https://www.altcap.com/

https://x.com/jaltma

---

https://linktr.ee/uncappedpod

Email: [email protected]

Christina Cacioppo is cofounder and CEO of Vanta, which is on a mission to secure the internet and protect consumer data. The trust management platform was valued at $2.5 billion in 2024 after a Series C investment led by Sequoia. Vanta went from $10M in annual recurring revenue in 2021 to $100M in 2024, while also giving us one of the best tech billboards of all time, “Compliance that doesn’t SOC 2 much.” Before founding Vanta in 2018, Christina was an investor at Union Square Ventures and helped bring Dropbox Paper to market as a product manager.

We covered:

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Timestamps:

(0:00) Intro

(0:25) Staying under the radar

(3:29) No referees in capitalism

(5:20) Shipping velocity

(6:43) Mindset on competition

(8:09) Structuring a GTM approach

(10:25) Fundraising strategies

(16:36) VCs being “helpful”

(21:57) Recruiting as you scale

(28:33) Adapting to the AI era

(32:09) What should be AI-ified

(38:18) Mental game of being a founder

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More on Vanta and Christina:

https://www.vanta.com/

https://x.com/christinacaci

More on Alt Capital and Jack:

https://www.altcap.com/

https://x.com/jaltma

---

https://linktr.ee/uncappedpod

Email: [email protected]

Mamoon Hamid is a Partner at Kleiner Perkins. He has been an early investor in and served on the boards of some of the most innovative software companies of recent times including Slack, Figma, Rippling, Glean and Box. Prior to joining Kleiner Perkins, Mamoon was a Co-founder and General Partner at Social Capital. He started his venture career in 2005 at U.S. Venture Partners (USVP) where he eventually became Partner. Mamoon came to Silicon Valley in 1997 to join Xilinx, a Kleiner Perkins company, where he spent six years, initially as an engineer and later in product and marketing roles.

We covered:

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Timestamps:

(0:00) Intro

(0:29) The dot-com bubble

(7:12) Web 2.0 and cloud

(16:03) Early days of mobile

(17:51) AI’s $60 trillion opportunity

(21:48) Where to invest in AI

(28:39) The future of robotics

(32:35) Reigniting a storied firm

(41:36) Growing vs recruiting talent

(46:42) Win rate aspirations

(49:16) Investing in Box, Slack, and Figma

(54:36) Assessing founders

(57:14) Kleiner Perkins’ strategy

(1:00:52) Family and faith

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More on Kleiner Perkins and Mamoon:

https://www.kleinerperkins.com/

https://x.com/mamoonha

More on Alt Capital and Jack:

https://www.altcap.com/

https://x.com/jaltma

---

https://linktr.ee/uncappedpod

Email: [email protected]

Vinod Khosla 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.

After graduating college, Vinod 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 intubated the idea for Juniper Networks to take on Cisco System’s dominance of the router market, a company that would give KPCB a 2,500x return on its early investment.

Vinod is driven by the belief that technology is a positive force multiplier to accelerate societal reinvention in food, health, climate, energy transportation, education, housing finance, media, retail and entertainment for billions around the globe. His greatest passion lies in being a mentor to entrepreneurs who are building companies to tackle society’s largest challenges.

We covered:

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Timestamps:

(0:00) Intro

(0:26) Craziness of the current cycle

(5:54) Predictions of the future

(9:35) Role of humans with AI

(16:20) Potential AI dystopia

(23:18) Investing in OpenAI

(33:21) Robotics being next

(39:53) Incumbents not innovating

(42:29) Mindset around risk

(44:14) Bull case for energy

(50:22) New transportation

(54:18) Future of medicine

(1:03:00) A different type of enjoyment

(1:05:40) Approaches to venture

(1:12:13) Khosla’s operating principles

(1:16:17) Staying energized

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Linktree: https://linktr.ee/uncappedpod

Twitter: https://x.com/jaltma

Email: [email protected]

It was a pleasure to sit down with Dan Feder, Senior Managing Director with the University of Michigan Investment Office who leads the endowment’s investments in venture capital and private equity.

Prior to joining the University of Michigan, Dan was the Managing Director of Private Markets at the Washington University Investment Management Company. Dan’s career in endowment management began at the Princeton University Investment Company where he led the development of Princeton’s global private equity and venture capital portfolio. Dan has also served as the Managing Director of Private Markets for the Sequoia Capital Heritage Fund (an endowment-style investment fund sponsored by Sequoia Capital) and as a Senior Investment Manager in the endowment services area at TIAA-CREF.

We covered:

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Timestamps:

(0:00) Intro

(0:40) Becoming an endowment manager

(2:59) Constructing an endowment’s portfolio

(9:10) Risk-based investing vs uncertainty

(13:07) Incentive structures in LP land

(16:28) Team construction

(22:26) Backing strategies that are at odds

(26:06) Why LPs invest in venture

(27:38) UMich framework to investing

(32:29) Picking individuals vs firms

(36:40) Big vs small funds

(40:48) How to pick fund managers

(45:41) Herd mentality in LP land

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Linktree: https://linktr.ee/uncappedpod

Twitter: https://x.com/jaltma

Email: [email protected]

This was a fun one! Sam is my brother and the CEO of a small company in SF called OpenAI. I’m glad he was able to take time out of his busy schedule to give me a hard time and share his thoughts on the future of AI.

We covered:

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Timestamps:

(0:00) Intro

(0:48) AI discovering new science

(5:40) Humanoids are the future

(8:27) A world with superintelligence

(11:20) Medium-term predictions

(15:37) Potential OpenAI apparatus

(19:01) Supply chain implications

(21:51) Meta / Scale AI news

(29:04) Personal reflections

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Linktree: https://linktr.ee/uncappedpod

Twitter: https://x.com/jaltma

Email: [email protected]