20 lessons from Shopify CEO Tobi Lütke

Sources: Acquired FM (Sep 2025), David Senra's Founders #350, Tobi's public memos.

1->Shopify started because he wanted to sell snowboards online and everything out there sucked. He built a tool for himself and the market pulled it out of him.

2-> If your old work doesn't embarrass you, you haven't grown. The gap between then and now is your progress.

3->A company is a socially acceptable excuse to go all in on one thing. Call your obsession a company and suddenly it's a job.

4->Books are cheat codes. His words. You can absorb someone's entire career in a few hours.

5->Find a rival, not a competitor. Competition makes you copy. Rivalry pushes you to your own peak.

6->When a core assumption changes, throw out every plan built on top of it. When COVID hit he reviewed every project and killed 60%.

7->He has a personal eval system for AI. A folder of prompts with expected results he runs against every new model. Basically unit tests for AI.

8->AI usage isn't optional at Shopify. His 2025 memo: teams must show AI can't do the job before asking for more headcount. It's in performance reviews now.

9->He tried cosplaying as a "normal CEO" after going public. Wore suits, followed the playbook. It flopped. Things improved when he went back to thinking like an engineer.

10->To fight sunk cost he pretends he's a corporate raider who just bought his own failing company. He literally writes hit pieces on his own past decisions.

11->Good tools raise the floor. Great tools raise the floor without lowering the ceiling. Most abstractions fail this.

12->You don't need to predict the future, just live slightly ahead of everyone else. He runs day-one iOS betas on his only phone. As a public company CEO.

13->Most companies stick high-agency founders in skunkworks to keep them quiet. He did the opposite and put them in charge of the biggest teams.

14->Subtraction is harder than addition. He considers the SpaceX Raptor engine a masterpiece because it was made great by removing things.

15->Replace "here's what you should do" with "for example." His co-founder Daniel suggested it. Completely changes how feedback lands.

16->Building in Ottawa instead of SF was a feature. He calls what happens in the Valley "cultural entropy." Everyone hops between the same companies and ends up thinking the same.

17->When the stock dropped 80% from its COVID peak he felt relief. The 70x revenue multiple felt fake. His job is building the company, not managing a stock price.

18->Think of yourself as the entrepreneur of your own work. Your skills are the product. Employment is a subscription a company buys from you.

19->You can't tell who has high agency until things go wrong. He looks for how people reacted minute by minute when stuff went sideways.

20->We're in the golden age and nobody notices. The Turing Test passed with zero fanfare. He thinks people will study this era like we study the Roman Republic.