Startup Corner #7: Thinking in Bets
Lessons in Entrepreneurship from Annie Duke's book 'Thinking in Bets'
Hey friends,
I just finished reading (or re-reading for the fifth time) Thinking in Bets by Annie Duke, and I’ve got to say — it might be the most useful decision-making framework I’ve come across.
This time, I re-read the book from the perspective of entrepreneurship and tried to apply the lessons from this book to the startup life.
Not because it gives you step-by-step instructions on how to run a company (it doesn’t), but because it reshapes how you think about uncertainty, outcomes, and — most importantly — your own biases.
In this post, I want to go deep. Not just to review the book, but to unpack how these ideas apply directly to startup life — and how some of the best (and worst) decisions we’ve seen in startups can be understood through the lens of Annie’s thinking.
1. Results ≠ quality decisions — why we judge ourselves all wrong
One of the core insights in Thinking in Bets is:
“We are quick to take credit for good outcomes and blame bad luck for bad ones.”
In poker, you can make the perfect play and still lose the hand. In startups, you can build the right product, for the right market, at the right time — and still get crushed.
Think about Quibi.
Raised $1.75B, had a stellar team, big names — and flopped.
Did they make all bad decisions? Not necessarily. But they misread behavior shifts, overestimated demand, and bet too heavily on brand power.
Compare that to Instagram, which pivoted from a failed app (Burbn) to photo sharing. It wasn’t a master plan — it was a bet. A great one, with the right timing. But luck played a part too.
The lesson?
Outcomes are noisy.
We need to separate process from result — otherwise, we optimize for the wrong thing.
→ Startup takeaway: Build a habit of post-mortems even for successful outcomes. Ask: “Was it a good decision at the time, or just a lucky break?”
2. “I’m 100% sure” — the most dangerous phrase in startups
Annie warns against certainty. In poker, professionals think in probabilities, not absolutes.
In the startup world, we often glorify the “go all in” mentality. But confidence without calibration is dangerous.
Look at Theranos — conviction taken to the extreme, blinding the team to reality.
Contrast that with Slack.
Stewart Butterfield publicly admitted they weren’t sure it would work. Instead of assuming, they built Slack with a feedback-first mindset. That humility helped them iterate fast and grow sustainably.
→ Startup takeaway: Say “I think there’s a 70% chance this works” instead of “this will work.” That shift unlocks optionality and intellectual honesty.
3. The “resulting” trap — when success becomes your worst teacher
“Resulting” is when we assume a good result means we made the right decision. It’s a cognitive trap — and it’s everywhere in startup land.
Clubhouse is a good example (Remember that today?).
Explosive growth during COVID? Sure. But the team mistook momentum for product-market fit and missed critical retention signals.
Meanwhile, Coinbase took a narrow early bet on Bitcoin only, which people mocked. But over time, it created clarity, trust, and compliance advantages. Had BTC tanked, that decision would’ve been called reckless.
→ Startup takeaway: Don’t confuse traction with correctness. Success needs to be audited just as much as failure.
4. Thinking in bets is thinking in experiments
Every startup decision is a bet — a move made with incomplete information, high uncertainty, and real stakes.
The best operators frame their decisions as hypotheses.
Superhuman did this masterfully. Rahul Vohra created a quantifiable product-market fit framework, using NPS surveys and cohort analysis to refine the product before scaling.
Netflix runs hundreds of A/B tests — not because they’re uncertain, but because they assume uncertainty is normal. Their culture punishes sloppy decisions, not failed experiments.
→ Startup takeaway: Think like a scientist. Every launch, hire, or strategy is a test. Write down your assumptions and treat every move as a learnable moment.
5. Build your decision group — stop thinking alone
Annie talks about “decision pods” — groups of people who help you reason better. Think of them as intellectual co-founders for your logic.
Imagine this: a small group of founders you meet with monthly to walk through decisions before you make them.
Not therapy.
Not bragging.
Just sharpening the thinking.
The best founders I know all have something like this. It’s not formal, but it’s intentional.
→ Startup takeaway: Build your “thinking circle.” Find people who challenge your logic, not just support your vision.
Final thoughts: Poker, not perfection
Thinking in Bets isn’t a tactical startup guide. It’s something deeper: a lens for viewing uncertainty with clarity and humility.
This book reminds me that it’s okay — even wise — to say, “I don’t know, but here’s the best bet I can make with what I’ve got.”
Every big decision a founder could make — product shifts, fundraising, hiring — try to ask:
What’s the bet you’re making?
What’s the probability?
What would Annie say about how you’re reasoning here?
If you’re building, investing, or advising, Thinking in Bets is worth your time. Not to teach you what to do, but to make you 10x better at thinking through what you do.
Until next time,
— RB
Was this helpful? Let me know by replying or leaving a comment. And if you’ve read the book too — I’d love to hear what stood out to you.