Brian Chesky - AI Founder Mode - [Invest Like the Best, EP.471]

Invest Like the Best with Patrick O'Shaughnessy

Colossus

Technology, Business, Investing

4.7 • 2.5K Ratings

🗓️ 5 May 2026

⏱️ 77 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

My guest today is Brian Chesky, the co-founder and CEO of Airbnb. Our conversation traces the path from his early training as an industrial designer at RISD through the pandemic moment that forced him into founder mode. He explains why he thinks AI founder mode will demand even more attention to the details and why founders are rarely good early CEOs. He walks through his eleven-star exercise, which is a way of imagining the most absurd version of a customer experience to achieve product market fit. We also talk about what changed for him when he stopped chasing adulation and started making things for the love of making them. For the full show notes, transcript, and links to mentioned content, check out the episode page ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠. ----- Become a Colossus member to get our quarterly print magazine and private audio experience, including exclusive profiles and early access to select episodes. Subscribe at ⁠colossus.com/subscribe⁠. ----- ⁠Ramp’s⁠ mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠ramp.com/invest⁠⁠ to sign up for free and get a $250 welcome bonus. ----- Trusted by thousands of businesses, ⁠Vanta⁠ continuously monitors your security posture and streamlines audits so you can win enterprise deals and build customer trust without the traditional overhead. Invest Like the Best listeners get a special offer of $1,000 off Vanta when you go to ⁠vanta.com/invest⁠. ----- WorkOS⁠ is the infrastructure B2B and AI-native companies use to sell to enterprise. It covers everything enterprise security requires: SSO, SCIM, RBAC, Audit Logs, AI governance, and more. Trusted by 2,000+ fast-growing companies, including OpenAI, Anthropic, Cursor, and Vercel. ----- Rogo is the AI platform for finance. They're building agents for Wall Street that are trained to understand how bankers and investors actually do work: from diligence and modeling, to turning analysis into deliverables. To learn more, visit rogo.ai/invest. ----- ⁠Ridgeline⁠ has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Visit⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ridgelineapps.com⁠. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠). Timestamps: (00:00:00) Welcome to Invest Like The Best (00:02:29) Episode Intro: Brian Chesky (00:03:07) Studying Industrial Design at RISD (00:08:30) Why Founders Don't Make Good CEOs (00:09:02) Founder Mode (00:12:51) AI Founder Mode (00:14:41) The End of Pure People Managers (00:18:42) Consumer AI (00:21:45) Project Hawaii (00:25:49) Make the Problem as Small as Possible (00:29:46) Becoming a Good CEO (00:32:11) What Brian Learned From Hiroki Asai (00:36:32) The Eleven-Star Experience (00:38:48) AI and Creativity (00:41:44) Making Things for the Love of It (00:43:36) The Adulation Trap (00:46:38) The Ham Sandwich Paradox (00:52:38) Why Founder-Led Businesses Endure (00:55:14) The Person as the Atomic Unit of Airbnb (00:59:40) Disrupting Yourself With AI (01:02:11) Lessons from Bodybuilding (01:07:55) Hiring as the Most Important Job (01:09:16) Are Founders Born or Made? (01:11:04) The Motivation of an Artist (01:11:47) The Kindest Thing

Transcript

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0:00.0	Most software companies try to maximize your time on their app to juice engagement.
0:03.8	Ramp does the exact opposite.
0:05.6	Ramp understands that no one wants to spend hours chasing receipts, reviewing expense reports,
0:10.0	and checking for policy violations.
0:12.0	So they built their tools to give that time back, using AI to automate 85% of expense
0:17.1	reviews with 99% accuracy.
0:19.3	And since Ramp saves companies 5%,
0:21.5	it's no wonder that Shopify runs on Ramp,
0:23.8	Stripe runs on Ramp, and my business does too.
0:26.1	To see what happens when you eliminate the busy work,
0:28.2	check out ramp.com slash invest.
0:30.6	Felix by Rogo is a personal finance agent
0:32.9	that turns a single prompt into finished client-ready work
0:35.8	using your firm's own templates, context, and
0:37.9	standards. Send Felix an email like, take these comments and turn them for me, or update my tracker
0:42.9	with the context of these emails. Or run the ability to pay math on this buyer, and Felix sends
0:48.0	back finished PowerPoint decks, Excel models, and sourced research. Felix works the way your
0:53.0	team already does, delivering work quickly
0:54.9	and accurately around the clock. Learn more at rogo.a.i slash Felix. Open AI, cursor, anthropic,
1:01.7	perplexity, and Versel all have something in common. They all use WorkOS. And here's why. To achieve
1:07.0	enterprise adoption at scale, you have to deliver on core capabilities like SSO,
1:11.7	SCIM, Rback, and audit logs.
	...

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