Every founder worries about making the wrong decision.
Wrong obsession.
The actual killer isn't bad decisions, it's the expensive mistakes you can't reverse.
Companies die when they optimize for "getting it right" instead of optimizing for "learning what's right, cheaply."
Ward Cunningham figured this out in software. Most founders still haven't figured it out in business. I watched this play out last year with a friend, SaaS company, bootstrapped profitably, decent traction. They needed to pick between two pricing models: usage-based or tiered subscriptions.
Three months of analysis.
I asked the CEO, "What's the cost of implementing both and seeing which one converts better?"
"Maybe 15K in dev work. Two weeks."
"And how much have you spent on analysis?"
He pulled up a spreadsheet. 47K in consulting fees. Hundreds of hours in internal meetings. Three months of market paralysis while competitors shipped updates.
This is the pattern that kills companies.
They were optimizing to avoid being wrong. They should've been optimizing to make being wrong cheap and reversible.
Cunningham's insights are apt than most founders realize. The constraint isn't making perfect decisions. The constraint is: can you afford to be wrong?
If you can't afford mistakes, you can't afford to learn. And if you can't learn, you definitely can't win.
The real question isn't, "What's the right pricing model?" It's, "How do I structure this so that finding out costs 15K instead of 120K in lost opportunity?"
That CEO?
We scrapped the analysis. Implemented both models as an A/B test. Had real data in three weeks. The "wrong" model revealed why customers were churning, something no survey caught.
Total cost of being wrong: 19K and two weeks. Value of learning what actually mattered: unfuckingquantifiable.
Your strategic paralysis isn't about intelligence. It's about infrastructure. If every decision feels like betting the company, you've designed your business wrong.
Try this diagnostic: List your last three "big" decisions. For each one, ask: What would've made testing both options 10x cheaper?"
If the answer is "nothing," your business model has a structural flaw.
Speed beats accuracy when you can iterate cheaply.
— Shashank