Jake Cooper is the Founder of Railway.

This conversation explores how AI accelerates the need for strong backend infrastructure, when to build vs buy in AI software, and why there are only two moats: solving hard problems and doing hard things.

We also unpack Railway’s bold product bets, like enabling creators to earn revenue with backend templates, building their own data centers, and not building their own AI models.

Jake also talks about their four week new hire onboarding, how they build a problem roadmap, why operators should be managers, and why you should almost never work weekends.

Thank you to Angelo Saraceno @ Railway and Erica Brescia Bacon @ Redpoint for help brainstorming topics for the conversation.

Thanks to Ramp for supporting this episode. It's the corporate card and expense management platform used by over 40,000 companies, like Shopify, CBRE and Stripe. Time is money. Save both with Ramp. Get your $250 here.

Timestamps:

(3:33) Solving the hardest problems in dev tools

(8:16) Starting with the hardest thing

(11:18) How AI accelerated the need for Railway

(12:50) Importance of backend in AI-native software

(16:52) Jake’s angel fundraise strategy

(20:51) Resisting AI for so long

(25:32) Using AI to get leverage

(29:57) Build vs buy in AI software

(33:22) When Jake knew Railway was working

(34:27) Creating infrastructure templates

(38:04) Building data centers and a cloud service

(40:27) Two moats: Hard problems and hard things

(46:25) Hitting 8-figures in revenue

(48:47) Railway’s four week onboarding

(54:25) Building a problem roadmap

(56:16) You can’t set your own culture

(1:01:58) Railway’s viral “How We Work” post

(1:08:39) Using Discord instead of Slack

(1:11:25) How hypergrowth companies mess up org design

(1:14:03) Why you shouldn’t work weekends

(1:19:45) Not betting big on AI models

(1:21:53) Lessons from Zuck, Martin Scorsese

Referenced

Railway

Careers at Railway

The Inward Draw of Capitalism

How We Work Volume 1

Volume 2

Volume 3

Volume 4

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