Most early-stage decisions are not made. They are survived.
[Stand-in opening: swap in a real decision from your last 30 days, in your own words.]
Here is something I have stopped pretending about. When I look back at the decisions that shaped my startup, almost none of them came from a clean analysis. They came from a deadline, a tired Tuesday, or a co-founder conversation that ran twenty minutes long.
And then I did the worse thing. I reopened decisions that were already made, because reopening felt like diligence. It was not. It was avoidance with a better name.
If you are early-stage, you do not have a decision-making problem. You have a cost-of-being-wrong problem, and most of us never price it. This issue is about pricing it.
Slack: the decision was to stop, not to start
In 2012, Stewart Butterfield's team shut down Glitch, the online game they had spent years building. They kept the internal chat tool they had built along the way. That tool became Slack.
The lesson is not "pivot more." Look at what made the decision survivable: the team already had a working asset in hand, and the game's numbers were telling them the truth every week. Being wrong was costly, but being slow to find out was the bigger risk, and they cut that short.
For an early-stage founder, the takeaway is smaller and more useful. The best decisions are often the ones where you shorten the time until reality answers back.
Quibi: what happens when money removes the feedback loop
Quibi launched in April 2020 after raising roughly $1.75 billion, and shut down about six months later. Plenty of post-mortems blame timing or the pandemic. The decision-making story is quieter.
With that much capital, the company could make enormous bets before any customer had a chance to say no. Every big call (content budget, format, pricing) was made on conviction, and the market answered only after the money was spent.
You probably do not have $1.75 billion. But you may have its smaller cousin: a six-month plan that never checks in with a real user.
The Cost-of-Wrong Test
Before any real decision, ask two questions and answer them in one line each.
How much does it cost if I am wrong? Count money, months, and relationships.
How fast will I find out? Days, weeks, or only after it is too late to change.
Those two answers tell you how much deciding effort the call deserves.
Cost if wrong | Time to find out | What to do |
|---|---|---|
Low | Fast | Decide today. Do not hold a meeting about it. |
Low | Slow | Decide this week, then set a date to check the result. |
High | Fast | Run the smallest real test first, then decide. |
High | Slow | Slow down. Buy information before you commit. |
Most founders spend their longest deliberation on the top row, where it buys the least. The bottom row is where the thinking time belongs.
Try it this week (10 minutes)
Write down every open decision on your plate. Aim for five to eight.
Next to each, write the two answers: cost if wrong, time to find out.
Place each one in the table above.
Close the top-row decisions today. Pick a check-in date for the second row.
For the bottom-row decisions, write down one piece of information that would change your mind, and go get it.
If a decision you already made keeps coming back, ask one more question: what new fact is reopening it? If there is none, it stays closed.
Before you go
Most of the work of an early-stage founder is deciding what deserves your thinking time and what does not. Price the mistake first, then spend your effort accordingly.
Reply to this email with the one decision you are stuck on right now. I read every reply, and the best ones may shape a future issue.