Thinking in Bets: What Poker Taught Us About Making Better Business Decisions
Hosts: Aaron Levine (Luxury Group Insurance Agency) and Tom Mirabella (Wingman Planning)
Book: Thinking in Bets: Making Smarter Decisions When You Don’t Have All the Facts by Annie Duke
Why this book, why now
In our third Book Club episode, we dug into Annie Duke’s playbook for making smarter choices when you never have perfect information. Annie’s background as a professional poker player turned decision strategist gives this topic real teeth. Business is rarely a clean equation. It is much closer to poker than chess, which means uncertainty, incomplete information, and probabilities are always in the mix.
We both listened on Audible and loved how approachable the ideas are. Annie’s frameworks help you pull emotion out of decisions, separate luck from skill, and turn every outcome into useful feedback.
Poker vs. Chess as a business metaphor
Chess is open information. Every piece is visible. If you blunder, you can precisely map the move that failed. Poker is different. You can make the best possible decision with the hand you see and still lose the pot because you do not control the unseen cards or your opponent’s behavior.
That makes poker a better mirror for real business:
You can prepare perfectly and still lose the deal on the one-yard line.
Competitors, timing, budgets, and hidden constraints are the unknown cards.
Strategy matters, yet outcomes remain probabilistic, not guaranteed.
Embracing “I’m not sure”
One of the most liberating takeaways is normalizing uncertainty. Saying “I’m not sure” is not weakness. It is an honest snapshot of your current knowledge. That honesty unlocks better research, better collaboration, and better choices.
We talked about how school often trains you to always have the answer. Real life rewards accuracy over speed. Telling a prospect “I need to run the numbers” can feel uncomfortable in the moment, but it prevents snap quotes and bad fits later.
Avoid the trap of “resulting”
Annie calls it “resulting” when we judge the quality of a decision purely by the outcome. Bad outcome does not automatically mean bad decision. Good outcome does not automatically mean good decision. Sometimes you made a great decision and variance bit you. Sometimes you made a poor decision and luck bailed you out.
The fix is to evaluate the process that led to the choice:
What options did we consider?
What data did we have?
How did we estimate probabilities and risks?
What assumptions were we leaning on?
Do that consistently and the wins stack up over time, even if any single hand goes sideways.
Build a decision feedback loop
Poker players make dozens of decisions per hour and then review them away from the table. That cadence is a model for teams.
What it looks like for us:
Debrief major calls, proposals, and creative choices, even when they succeed.
Capture the signal while it is fresh. Note the context, not just the headline.
Ask, “What would we change next time,” not “Who is to blame.”
Small upgrades to the process compound. Over a quarter, you feel it in smoother pitches, tighter pricing ranges, and fewer surprises.
Decision pods: your mini board of directors
Annie recommends small, trusted groups to stress-test your thinking. We like calling them decision pods. The rules are simple:
Share the context and your draft decision.
Invite candid critique, not cheerleading.
Reward people for proving you wrong early, which is cheaper than being wrong late.
External eyes cut through internal bias, especially when your team naturally wants to support the boss. Give your pod permission to be blunt.
Read the table in sales
Selling has tells just like poker:
Prospects throw out a number to anchor you.
Body language shifts when you hit a sore point, like an ad budget that feels high.
Silence after a question can signal they are protecting hidden constraints.
The goal is not to “call them out.” It is to re-ask, reframe, and surface the real hand. Sometimes you will realize you are not the right fit, which is a win because you avoided a bad match.
Words shape decisions
We circled a simple language upgrade that changes outcomes. It is rarely “spend.” It is “invest.” Insurance is investing in the ability to recover. Marketing is investing in acquisition and brand. The word is not a trick. It is a truer description of what is happening over time.
The 10-10-10 check
A quick tool we love: ask how a decision will feel in 10 minutes, 10 months, and 10 years.
Ten minutes tests your emotional impulse.
Ten months asks about medium-term consequences once the dust settles.
Ten years puts the choice in the context of your reputation and compounding results.
This simple lens cools hot takes and highlights second-order effects.
Separate luck from skill
Outcomes blend both. The discipline is to keep score on the part you control.
Skill: research, preparation, pricing logic, creative process, follow-through.
Luck: timing, budget shifts, a surprise competitor, a prospect’s internal politics.
Track the inputs you own. Accept the rest without spiraling. That keeps morale high and momentum steady.
Practical ways to apply this week
Write before you decide. One paragraph that states the goal, options, assumptions, and probabilities.
Rate your confidence. “70% likely” is better than “pretty sure.” It nudges you to find the 30% risk.
Schedule debriefs. Win or lose, review big decisions for five minutes while details are fresh.
Start a decision pod. Three to five sharp peers who will challenge you with no sugar-coating.
Ban “resulting.” In meetings, correct it when someone declares a decision “good” only because it worked.
Reframe the ask. Replace “quote me now” with “here is the range and what would tighten it.”
Use the 10-10-10 rule. Especially for pricing, hiring, and long-term commitments.
A favorite line to keep handy
“What makes a great decision is not that it has a great outcome. A great decision is the result of a good process.”
Put that on the wall. It changes how a team talks about wins and losses and it makes improvement feel achievable.
Final thoughts
Thinking in Bets is a field guide for anyone who operates under uncertainty, which is everyone in business. Treat choices like wagers. Get honest about what you know and what you do not. Tighten your process, gather feedback, and let the probabilities work over time.
If this topic resonates, give the episode a listen and share it with a teammate. Better yet, have your team read the book and run a 30-minute debrief together. Decisions are the one thing every role has in common. Getting just a little better at them pays off everywhere.
This podcast episode was filmed at Wingman Planning in Belmar.
