The Solo Founder Playbook: Railway From Side Project to $100M ARR

Startup Playbooks

The Solo Founder Playbook: Railway From Side Project to $100M ARR

8 Operating Rules From Jake Cooper With Templates to Run Your Startup the Same Way

Guillermo Flor

Oct 16, 2026

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Railway started 2026 at around $20M in ARR. It is now about to cross $100M.

It has 40 employees and

one founder

.

A $100M Series B in January, led by TQ Ventures

More than 2 million developers on the platform

$90M of its own data center hardware

No sales team until last year

Railway is a cloud where developers, and now their coding agents, deploy apps and databases without touching servers. Many developer platforms sit on top of AWS or Google Cloud and pay their prices. Railway runs on servers it bought, so its margin grows with usage.

Its founder? Jake Cooper left Uber in 2020 and set up a box of databases for his side projects. He posted it on Twitter asking who he should talk to about a job. He got zero job offers and a few angel checks.

📚 In this newsletter, we break down the 8 rules Jake uses to run Railway plus the templates to copy them in your own startup!

Inside you will find:

Why Two Co-Founders Is the Worst Number

Find out why Jake never looked for a co-founder and how he gets outvoted on purpose.

How Railway Survived Losing $500K a Month

See why he killed the free tier and brought it back only once Railway owned its hardware.

Solve the Problem Before You Look at How Stripe Did It

Learn the innovation tokens rule for deciding what to reinvent and what to buy.

Say No to 90% of Ideas With One Question: Why Now?

Copy the one-page abstract every Railway initiative needs before it reaches planning.

Do the Job Manually Before You Hire for It

Build the role spec from work you’ve already done, and see how Railway keeps its people.

The Six-Week Onboarding: Trust, Clarity, Judgment

Copy the plan that took a new hire to owning the entire edge network within a year.

Write Values That Check Each Other

See how Railway’s four values work as brakes on each other, and what one of them cost.

Move One Brick a Week, 52 Times a Year

Set up the weekly rhythm and the 36 offline hours behind Jake’s biggest decisions.

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