The Railway OS: Saying No to 90% of Ideas and Finding Step Changes in Stillness
Key points
Key takeaways from the Knuckle Up with Nakul interview with Railway founder and CEO Jake Cooper (October 2026):
An accidental company. After leaving Uber in 2020, Cooper assembled a box of databases for his own side projects, kept coming back to it, and posted it on Twitter asking who he could talk to about a job working on it. He received no job offers — just a few angel checks — and the side project became Railway, today a cloud platform used by millions of developers, run by roughly 40 people and closing in on $100 million in annual revenue.
Surviving a $500K monthly burn. In the free-tier era Railway lost around $500K a month and at one point faced runway measured in single-digit months. Cooper cut the free tier off, spent two to three years building out Railway's own bare-metal data centres — a software company now owning about $90 million of its own hardware — and only then brought free usage back on top of a paid foundation that is growing rapidly.
Compounding, brick by brick. The vertical growth chart was not one change but several inflections: free-tier-spiked growth, roughly a year in the trough after free users were pulled, then compounding from around late 2022. Cooper's internal motto, borrowed from an old friend at Robinhood, is "brick by brick" — move the company's biggest problem forward every week, 52 weeks a year.
Saying no to 90%. Railway says no to about nine in ten internally proposed ideas — no conferences, no side projects — until a particular thing becomes inevitable, at which point the whole organisation commits and says yes. The Jim Collins hedgehog principle underpins it: do only what you can be the best in the world at.
Solving the problem before reading the playbook. Cooper treats looking at how Stripe or Cursor solved a problem as "cheating on your homework" — it pollutes his own thinking — so Railway forms its own answer first and checks others' approaches only as a last resort, spending its "innovation tokens" (a concept he credits to Tailscale) carefully. For go-to-market inspiration he does track companies such as Ramp and reverse-engineer which of their moves fit.
Solo founder, remote team, generous comp. Cooper never did "co-founder dating" and argues two is the worst number of co-founders; being the sole response-holder means he is the last person who picks up the phone. The company is fully remote to pull the best people from every facet of the world, and compensation is revisited roughly every quarter — "never be stingy with talent."
Ownership, values and no AI slop. A six-week onboarding built on trust, clarity and judgment turns new hires into owners, and the culture is spelled out as HARD (Honourable, Accelerating, Reliable, Direct). Cooper insists the team does not use AI to draft the memos it shares internally — nobody should have to read something "you have slopped out and pushed onto somebody else."
Stillness over 996. Cooper goes dark from Friday night to Sunday afternoon, arguing that 996 buys at most 20% more cycles while stillness is where step-change ideas emerge. He believes most startup advice is overrated because "you have to plot your own journey."
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