Startup Operating Principles

After three and a half years, this is a compliment of sorts to Operating well – what I learned at Stripe.

Decision making

1. Sense of urgency: why can’t we do this today? Never do anything you could do today tomorrow, or anything next week you could do today. Amp it up!

2. No snacking: only work on the big stuff. The hard part of focus is saying no to the things you want to do. Also see the LNO framework.

3. Counterintuitively, to get to the big stuff, you need to be in the details. It’s important to be data driven, but we only can understand what is going on if you look line-by-line at data. Go look at 50 last calls/deals/cases. It is never a waste of time.

4. Delete before you optimize

   1. Question every requirement

   2. Delete - remove everything you can

   3. Only then simplify and optimize

5. Outside in: don’t get stuck in our internal view. For every change, pretend you are a customer (think specifically about who that customer is - 73 year old woman from Palm Springs calling about her husband’s unexpected passing - and what assumptions they have).

6. Steel threads: build the thinnest thing end to end first, then reinforce.

Communication

1. Write before you talk. Writing creates clarity and alignment while preserving context.

2. Close the loop. Don’t leave threads hanging. A lack of update is still an update.

3. Show your work. Even if it’s early or messy, visibility beats silence.

4. Don’t hand off ambiguity. Ask the next question, suggest a path forward, or take a first pass.

5. Assume context gaps, not intent gaps. Be generous in how you interpret; be direct in how you clarify.

8. Send messages anytime - let recipients manage themselves. Everyone manages their own time and boundaries.

9. Ask for No, not Yes. If it’s in scope, low risk, or you’re likely right—don’t wait. Inform with when you plan to move ahead without their input.

9. Use the Minto Pyramid to organize your ideas