Railway started the year at $20M ARR. It’s now ~$100M. Solo founder. Fully remote. Only ~40 people. The one trait that explains why Railway is breaking all the rules: “It’s almost like cheating on your homework when you go and look at somebody else’s solution. If this is how Stripe does this or this is how Cursor does this, I don’t want to hear about it.” Jake Cooper (@justjake). Founder and CEO of @Railway. Knuckle Up ↓ -- In this conversation with Jake Cooper: 00:00 Who is Jake Cooper? 02:54 How did Railway survive losing $500K a month? 06:01 What made Railway’s growth chart go vertical? 09:45 Why won’t Jake look at how other companies solve problems? 14:34 Is two the worst number of co-founders? 20:04 How does a 40-person team hit $100M in ARR? 22:41 Why does Railway say no to 90% of ideas? 28:55 How do you compete for talent against the AI labs? 32:25 What does a technical interview look like after Opus 4.5? 35:34 Trust, clarity, judgment: how does Railway’s six-week onboarding work? 44:59 What does HARD stand for, and which value costs the most? 48:49 Why does Jake go dark from Friday night to Sunday? 54:54 What breaks first in a world with 10,000x more software? 59:49 Where does Railway play in two years? 1:01:37 How has Jake had to grow as a CEO? 1:09:29 Is burnout just an input-output mismatch? 1:12:27 Why does Jake think most startup advice is overrated?