This week I sat down with Garry Tan, President & CEO of Y Combinator. YC has funded 5,000+ startups including Airbnb, Stripe, DoorDash, Rippling, and Reddit, among others that have totaled $600B in combined valuation.

Garry is a designer, engineer, and investor in early stage startups. Previously Founder & Managing Partner of Initialized Capital, an early stage venture capital fund that was earliest in Coinbase and Instacart. Before that, Garry was a partner at Y Combinator where he invested in and directly worked with over 700 companies at the earliest stage. He previously co-founded Posterous and helped build it to a world-class website used by millions (acquired by Twitter).

Garry is a builder at heart.

We covered:

Timestamps:

(0:00) Intro

(0:25) Running YC like a founder

(6:25) Focusing on growth and prosperity

(12:40) Incredible pick rate

(14:34) Role of the Group Partner

(19:21) Lean vs fat startups

(20:53) Archetypes of special founders

(25:18) Rule changes because of AI

(33:00) YC being the “YC of hard tech”

(37:40) Community and political involvement

Linktree: https://linktr.ee/uncappedpod

Twitter: https://x.com/jaltma

Email: [email protected]

It’s always a pleasure to jam with Elad Gil, a serial entrepreneur and a startup investor. As an early leader at Google, Elad helped build the initial mobile team, before founding MixerLabs, which was acquired by Twitter. Later, he co-founded Color Health, a genetic testing company specializing in cancer detection. Over the past decade, he's backed nearly 40+ companies valued north of $1B each, including Airbnb, Coinbase, Figma, Instacart, and Stripe. He's also invested in Harvey, Mistral, Perplexity, Pika, and other leading AI startups.

Elad is also author of the High Growth Handbook and is excited to be working on his next book focused on how to scale during the zero to one phase of a startup’s journey. 

We covered:

Timestamps:

(0:00) Intro

(0:50) Shamelessness mindset

(4:16) Optimizing for market need

(5:55) Cultivating optionality

(8:29) Characteristics of people with long career arcs

(9:54) What to optimize for early in a career

(22:20) Different phases of your life

(25:20) Aspiring to do things that are useful

(26:33) Pivot points in careers

(31:16) Becoming great investors

(33:28) Getting more leverage on time

(36:57) Investing outside of AI

(40:58) Getting the theme right means more

(47:01) Elad’s new book

Linktree: https://linktr.ee/uncappedpod

Twitter: https://x.com/jaltma

Email: [email protected]

I was pumped to chat this week with Sarah Guo. Sarah is a startup investor and the founder of Conviction, an investment firm purpose-built to serve intelligent software, or "Software 3.0" companies. Some of her investments include Harvey, Mistral AI, Sierra, Cognition, HeyGen, and Cartesia, among others. Prior to 2022, she spent nearly a decade incubating and investing as a General Partner at Greylock Partners. Sarah co-hosts a podcast with Elad Gil called No Priors where they discuss the AI revolution.

We covered: 

Timestamps:

(0:00) Intro

(0:11) What a VC firm is at its core

(2:27) Compounding qualities of enduring firms

(6:44) Intentionality behind building Conviction’s brand

(13:01) Correlation or causation between brands and returns

(16:33) Shape of the current VC market

(27:15) Learnings from experience at Greylock

(32:06) Market vs founder driven

(33:55) AI conversation shifting from inputs to outputs

(36:28) More billion dollar companies than ever before

(42:44) Agency being the last human resource

(44:40) Important skills for kids to learn

Linktree: https://linktr.ee/uncappedpod

Twitter: https://x.com/jaltma

Email: [email protected]

Adam Guild is the CEO of Owner, a business he started when he was only 17. It now has tens of millions of revenue, hundreds of employees, and thousands of customers.

I’ve had the pleasure of working on his board for a few years now, and he is one of the most impressive people I’ve ever gotten to know. Working with him was a big part of what made me realize I want to do venture for the rest of my career.

He tracks his nutrition, exercise, time, and sleep to an extreme degree so he can show up to work every day as strong as possible. He goes to extreme lengths to recruit the best talent. He is equal parts hungry to learn from everyone around him, but courageous in making his own unconventional decisions.

I think he’s one of the most under-known founders right now, but I think that will soon change. 

Hope you enjoy watching this.

Timestamps:

(0:00) Intro

(0:07) Inside the mind of a young founder

(6:36) Boldly purchasing Owner’s domain

(9:34) Listening to others vs being instinctual

(14:12) Decision making as a CEO

(16:43) Fostering a culture while scaling

(18:34) High impact interview questions

(21:29) Recruiting the best talent

(29:50) Never missing an investor update

(34:16) Getting canceled on Twitter

(42:41) Startups are the Olympics of business

Linktree: https://linktr.ee/uncappedpod

Twitter: https://x.com/jaltma

Email: [email protected]

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.

(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

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.

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

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.

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

I could have happily spoken with Shaun for four hours.

Linktree: https://linktr.ee/uncappedpod

Twitter: https://x.com/jaltma

Email: [email protected]