Thinking in Bets: Annie Duke on Making Smarter Decisions When You Don't Have All the Facts - Greatest Hits! (SB1837)

The Stacking Benjamins Show

Joe Saul-Sehy and Josh ‘OG’ Bannerman, CFP

Personal Finance, Financial Planning, Education, Retirement, Investing, Cfp, Business, Money

4.4 • 2K Ratings

🗓️ 4 May 2026

⏱️ 67 minutes

🔗️ Recording | iTunes | RSS

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Summary

What if the reason your investment decisions feel so hard isn't the market -- it's how you're wired to think about outcomes? Annie Duke spent years as a professional poker player winning over $4 million in tournaments, then devoted the next chapter of her career to understanding why smart people consistently make bad decisions. The answer has nothing to do with intelligence and everything to do with how we confuse results with quality. She brings the full framework down to the basement today.

What You'll Walk Away With

Why certainty is the enemy of good decision making -- and the mindset shift that makes uncertainty feel like an advantage instead of a threat
The Pete Carroll problem: how tying the outcome of a decision to the quality of the decision is quietly wrecking how you evaluate your investments
Why being smarter actually makes this bias worse -- and how intelligent people spin data to confirm what they already believe more effectively than anyone else
The difference between wanting to be right and wanting to be accurate -- and why that single distinction changes everything about how you process new information
How to hold your beliefs as "works in progress" rather than positions to defend -- and why that opens you up to information that actually improves your decisions
Why the stock market's short-term volatility is almost never the signal investors treat it as -- and what a 40-year Berkshire Hathaway chart actually tells you
The poker table parallel to long-term investing -- and why you can make all the right moves and still lose, which means a bad outcome never proves a bad decision
What the Philly Special play reveals about how we reward boldness only when it works -- and what that tells you about how you judge your own financial choices
A listener question on market-cap weighted index funds -- why the s and p is built the way it is and what you'd actually need to do to weight it differently
The best personal finance and business books the crew is reading right now -- including picks from OG that go well beyond the usual recommendations

Why This Matters Now

For Stackers in their 40s watching a volatile market and second-guessing decisions that were perfectly sound six months ago, this episode is a direct intervention. The temptation to call a good decision bad because the market moved against you -- or to abandon a long-term strategy because of a short-term result -- is exactly the bias Annie Duke has spent her career studying. The framework she brings today doesn't just apply to poker. It applies to every financial decision you'll make for the rest of your life.

From the Basement

Annie Duke joins Joe and OG to walk through the decision-making framework behind her book Thinking in Bets -- including the Super Bowl story that reframes how most people evaluate every financial move they've ever made. The headline segment tackles parents spending six figures on kids' extracurriculars and what the trade-off actually looks like for retirement savings. Doug arrives with poker-themed trivia about the all-time tournament earnings leader, gets it mostly right, and declares victory anyway. Whether the basement poker tournament ended in anyone's favor is a matter of some dispute.

Resources Mentioned

Thinking in Bets by Annie Duke -- available wherever books are sold
Annie Duke's website and weekly newsletter -- annieduke.com
Annie Duke on Twitter -- @AnniedDuke
The Truth About Money by Ric Edelman -- recommended by Joe
Set for Life by Scott Trench -- recommended by Joe
Broke Millennial by Erin Lowry -- recommended by Joe
How to Be a Financial Grownup by Bobbi Rebell -- recommended by Joe
The Behavior Gap and The One-Page Financial Plan by Carl Richards -- recommended by OG
Fooling Some of the People All of the Time by David Einhorn -- recommended by OG
Built to Sell by John Warrillow -- recommended by OG
The E-Myth by Michael Gerber -- recommended by Joe
The Goal by Eliyahu Goldratt -- recommended by Joe
Stacking Benjamins Community -- stackingbenjamins.com/basement

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Transcript

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0:00.0	Hey there, Stackers. Happy Monday. And on today's episode, we are featuring the one and only
0:06.6	Annie Duke, former poker champion. She also had a couple great books a few years back,
0:13.6	thinking in bets was one of them. And the important thing about Annie is that she talks about
0:19.2	how to make smarter decisions when you don't have all the facts,
0:22.2	which is where poker really meets investing and living, isn't it? It's every money decision
0:28.8	you've ever made, like investing as, well, like not just investing, but buying a house, changing jobs jobs how well is that going to go helping your
0:41.7	kids deciding whether doug should be allowed near the nacho cheese machine none of those
0:47.4	come with perfect information and that's why i think this episode is so important in fact
0:53.3	that is not only the only thing that's
0:56.3	important about this. Here's the funny thing, Stackers. I would love for you to tell me if this
1:02.8	still holds up because the reason I'm playing this for you is because I think it does hold up.
1:08.3	This episode originally, Annie came here in 2018, which sadly feels like she was just here,
1:15.4	like many of our superstar mentors that we normally feature on Wednesday, but this week
1:20.6	on Monday.
1:21.7	But another piece is we used to do the headlines before Annie, so you're going to hear a couple
1:25.4	of headlines first.
1:27.0	And I want you to listen
1:28.1	closely to these headlines because we talk about mortgage rates feeling high and we then the the
1:36.0	piece that we're going to bring up talks about how mortgage rates felt high you know why because they
1:43.6	was because they were flirting with 5%.
1:47.8	Remember that? People nervous because rates weren't 3% anymore. So fast forward to now and 5%
1:55.4	sounds like something you'd frame, right, and hang over the fireplace. We weren't making
	...

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