Grit

Latest Episodes:

Inside the AI Startup Making Customer Support 65% Cheaper Sep 21, 2026

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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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The AI Race Has a Leaderboard | Arena CEO Anastasios Angelopoulos Sep 07, 2026

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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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Data Centers in Orbit by 2028: Baiju Bhatt on His Plans After Robinhood Aug 24, 2026

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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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Booking.com CEO on AI and the Future of Travel Aug 10, 2026

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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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Ex-Twitter CEO on Why AI Needs a New Internet | Parag Agrawal Jul 27, 2026

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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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The Sales Framework Every Founder Needs | Mark Roberge Jul 13, 2026

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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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Airwallex's Jack Zhang on Fintech, Failure, and Growth Jun 29, 2026

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In 2020, Airwallex lost nearly half its revenue overnight. Today it's worth $11 billion.

Jack Zhang reflects on the decisions that kept the company alive, raising capital during uncertainty, and leading through its toughest chapter.

This episode is a candid look at why Jack chose to keep building, even when a $1.2 billion acquisition was on the table.

Guest: Jack Zhang, founder and CEO, Airwallex

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Why 80% of the Fortune 100 Chose Qualtrics | Ryan Smith Jun 15, 2026

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AI may change software overnight, but company building still takes time.

Ryan Smith explains why, despite the pace of AI, “the race is going to be way longer than anyone thinks.”

He reflects on Qualtrics surviving multiple market cycles and ultimately being acquired by SAP for $8 billion days before going public.

Guest: Ryan Smith, co-founder Qualtrics

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What It Takes to Build Software for 171,000+ Restaurants | Aman Narang Jun 01, 2026

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Great software companies often come from understanding pain points at a very deep level.

On Grit, Aman Narang shares how Toast built trust with 171,000+ restaurant operators by helping restaurants manage everything from payments and online orders to staff scheduling and daily operations.

He also reflects on lessons around product-market fit and scaling a company before it’s fully ready.

Guest: Aman Narang, co-founder and CEO, Toast

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What It Takes to Build a Generational Company | Anduril’s Trae Stephens May 18, 2026

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Founder quality becomes more important as startups become easier to build.

Trae Stephens, co-founder of Anduril and partner at Founders Fund, has spent years backing founders with strong conviction, including most recently at Roadrunner.

He shares why too much capital too early can hurt startups, and why the best companies are built by teams with complementary strengths.

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