This week I sat down with Aaron Levie, Co-Founder and CEO of Box. Aaron came up with the idea behind the cloud computing company as a 19 year old college student and has led the company since its inception in 2005. Today, Box does over $1B in revenue with a market cap of $4.4B, and has raised over $560 million from the likes of DFJ, Andreesen Horowitz, and Meritech Capital.

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Timestamps:

(0:00) Intro

(0:10) Excitement in AI

(6:50) Startups vs incumbents

(15:04) Pricing agents

(17:42) AI over or under hyped

(19:17) Being first to cloud

(24:55) Staying motivated

(28:29) Shifting political landscape

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Linktree: https://linktr.ee/uncappedpod

Twitter: https://x.com/jaltma

Email: [email protected]

This week I enjoyed speaking quickly with Keith Rabois, a Managing Director at Khosla Ventures and the CEO of OpenStore. At Khosla, Keith 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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We covered:

(0:00) Competing where there isn’t competition

(2:29) Traits of top decile founders

(7:16) Picking people

(9:57) Being a consigliere

(13:54) Decision making

(21:51) Acting when confident

(26:43) Advantages of a large fund

(31:06) Raising in a frothy market

(35:47) Tech and the government

(43:21) Being vocal on politics

(46:47) Valuing board members

(52:24) Former operators vs career investors

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Linktree: https://linktr.ee/uncappedpod

Twitter: https://x.com/jaltma

Email: [email protected]

This week I spoke with Shaun Maguire, a Partner at Sequoia Capital. He led their investments into SpaceX, The Boring Co, and X among others. Prior to Sequoia Shaun co-founded a cybersecurity company which was acquired for $1B and worked at DARPA. I could have happily spoken with Shaun for four hours.

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We covered:

(0:00) Speaking his mind in public

(13:38) Trust and the media

(24:27) Tech’s political flip

(29:27) Investing in hard tech vs. software

(45:27) Thinking with a beginner's mind

(52:30) Fulfillment in investing

(59:33) Investing in outlier people

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Linktree: https://linktr.ee/uncappedpod

Twitter: https://x.com/jaltma

Email: [email protected]