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The Peel with Turner Novak

Solving the Hardest Problems in Dev Tools | Jake Cooper, Founder of Railway

The Peel with Turner Novak

Turner Novak

Technology

4.611 Ratings

🗓️ 18 July 2025

⏱️ 88 minutes

🧾️ Download transcript

Summary

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


Follow Jake

Twitter

LinkedIn

Substack


Follow Turner

Twitter

LinkedIn


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Transcript

Click on a timestamp to play from that location

0:00.0

there's only two moats. Hard problems, doing hard things. We want to make it as cheap as possible in both time and money, saving a ton of time to go in and spit up these things and then only paying for what you actually use when you're going and doing that. We want you to spend as little time as possible on the kind of configuration, drudge work, et cetera, so that you can actually go out and build the thing you actually wanted to go out and do, right? Like, we won't start a business to go and learn about answer or Kubernetes or any of this,

0:23.8

this other thing, but current generation of software, if you want to start a business that will actually kind of like scale for you, you do have to go and learn these things, right? Unless you use, you know, the tools that we were building so that you can actually spend all the time working on the actual problem that you started your business to solve. Welcome to the Peel. I'm your host, Turner Novak, founder of Banana Capital.

0:42.5

Today's guest is Jake Cooper, founder of Railway. We make all of that stuff that you would need to

0:47.0

potentially retain somebody to go and manage those things. You can just do it yourself.

0:51.2

Jake has grown Railway to mid-eight figures in revenue, and our conversation gets into how

0:54.8

they solve the hardest problems in dev tools and the importance of back-end infrastructure

0:59.2

in AI-native software.

1:00.8

In the age of AI, there's a very, very material risk of being out executed by your competitors

1:06.0

because they are moving so quickly.

1:08.0

Railway has made a bunch of creative and bold product bets, like enabling

1:11.2

users to create templates, earning a revenue share when other people use them, and building

1:15.0

their own data centers and cloud service. We want to be as quick as possible, and Racking

1:20.1

Rones allows us to move even closer to that kind of like metal. We talked about how Railway fully

1:25.0

ramps new hires in four weeks. Everybody joins a startup to be told what to do.

1:29.8

They join a startup to work on hard problems.

1:32.3

Using Discord instead of Slack, what hypergrowth companies get wrong on org design?

1:36.3

It's really, really important to have operators be also managers.

1:40.3

And why you shouldn't always work on the weekend.

1:42.3

Horsepower gets you a lot of the way, but at a certain point, you need to refine your technique.

1:49.1

And if you're working all the time, you don't really have a space to figure out where you've essentially lost time.

1:54.8

A quick thank you to Angelo at Railway and Erica at Redpoint for helping brainstorm topics for Jake.

1:59.3

A reminder, I publish two episodes of The Peel every week exploring the world's greatest startup stories just like this one.

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