“Don’t go public without understanding your go-to-market.”

Jeff Lawson reflects on Twilio’s go-to-market mistakes, including how the company generated hundreds of millions in revenue with just 7 sales reps.

He also shares how AI is changing the economics of software and why he’s betting on fusion energy instead of entering the AI startup race.

Guest: Jeff Lawson, co-founder and former CEO of Twilio, and co-founder and CEO of Inertia

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At Vercel, 91% of support volume is already resolved by an agent.

After spending a decade at Google and another at Stripe, Jeanne Grosser shares how AI is changing the way Vercel goes to market.

She also talks about the founder relationship as a “professional marriage,” what she looks for in a company she can stay at for a decade, and why she believes every pixel on the internet could eventually be built on Vercel.

Guest: Jeanne Grosser, COO of Vercel

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How do you keep up when you go from 50 to 500 employees in a year?

Jesse Zhang shares how Decagon scaled that quickly, from hiring ahead of demand to keeping the company connected as the team grows.

He also explains why the zero-to-one phase is so different from scaling, and how Decagon found its way out of the idea maze in just three weeks.

Guest: Jesse Zhang, Co-founder and CEO, Decagon

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AI could be bigger than electricity.

Anastasios Angelopoulos is seeing that shift firsthand, with Arena ranking 500+ models and tracking roughly 10 new releases every week.

On Grit, he explains why there may never be one dominant AI model and why the API layer may be less sticky than people think.

Guest: Anastasios Angelopoulos, Co-Founder and CEO of Arena

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What kind of founder walks away from a multi-billion-dollar fintech company to start building rockets?

Baiju Bhatt, co-founder of Robinhood, joins Joubin Mirzadegan to talk about life after one of the most consequential companies in modern finance, and why he's now betting on Cowboy Space Corporation, an orbital infrastructure company building AI data centers that ride to space inside its own rockets.

"I still have that dog in me," he says.

Baiju opens up about building alone for the first time in 15 years and what he learned about product-market fit while scaling Robinhood through its most chaotic years.

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"Our mission is to make it easier for everybody to experience the world."

From the dot-com crash to AI, Glenn Fogel has spent nearly three decades helping Booking Holdings evolve through every major technology shift while staying true to that mission.

He also shares with Joubin Mirzadegan why "you're always selling," and how Booking is using AI to amplify what every employee can accomplish.

Guest: Glenn Fogel, CEO of Booking Holdings

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"The answer to every problem is a model."

Parag Agrawal shares the ideas behind Parallel: products that continuously learn, and teams designed around versatile problem solvers.

He also shares why he built an AI agent for himself, and why AI's biggest opportunity is expanding what people can achieve.

Guest: Parag Agrawal, founder and CEO of Parallel, and former CEO of Twitter

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"There's 20 fires going on at every moment in the office and you have enough water to put out four."

Mark Roberge shares what it takes to build and scale a company, from finding product-market fit to knowing when it's time to grow.

He also shares the framework behind his new book, The Science of Selling, and why founders should scale based on their own data, not another company's success.

Guest: Mark Roberge, Founding CRO of HubSpot, HBS Professor, and Co-Founder at Stage 2 Capital

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