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Update frequency:
weekly
Average audio length:
11 minutes
English
United States
24 episodes
since June 8, 2026
episodic

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“No, let’s plan around 10%. That’s what I’m going to assume.” I typed that into ChatGPT. I was preparing for a presentation to real estate agents and I’d asked whether investing $2,000 a month for 15 years at a 10% return would let a hypothetical agent retire on $8,000 a month. Its first answer was…

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If you had $4 million in assets, no debt, and $70,000 a year of truly passive income, would you feel financially free? Maybe not as much as you’d think. ... So I’m asking you: what decision have you been making because money told you to... that you’d make differently if the Benjamins didn’t get a v…
I was 21 the first time I was told I talked too much for how young I was. Then, 22 the second time. Two different leaders, two different rooms, months apart. Both said almost the exact same sentence. I found out later they’d talked about me in between ... the first had used that exact phrase with t…
I wanted to be president of the United States. Not in the vague, anything’s-possible way kids get coached into saying ... I actually believed it, the way you believe things before anyone’s gotten around to telling you no. I’m still that kid some years. Brandon and I set genuinely lofty goals every …
Most people build a safety net for one kind of phone call: the lawsuit, the client who walks, the equipment that dies on a Tuesday. That’s not wrong ... it’s just half the story. A reserve funded above the bare minimum isn’t only defense. It’s optionality. It’s what lets you say yes to the good pho…
We were a small coffee shop making less than a thousand dollars a day, some days a lot less. Compared to Starbucks, we sucked. That wasn’t a throwaway line. It was actually what we told our team, out loud, at our third anniversary staff dinner. We handed out awards, ate cake, and then Brandon said …
I’m not much of a bettor. As a kid, I made small bets and lost almost every one, until I just stopped making them. I remember losing one and having to walk about a mile over it. Nothing terrible ever came from any bet I lost. I just don’t like giving something up when I have no real control over ho…
“So far, so good” is the sentence people say right up until the test arrives. Nothing going wrong feels like proof the system works. It’s actually just proof the crisis hasn’t hit yet. If you haven’t had someone look at everything you own side-by-side, what would it take for you to actually do th…
In October 2004, Brandon hosted a bonfire that almost burned a house down. That’s the night we met. I grew up in the country. I love a bonfire. I went. I was dating someone else at the time, so when Brandon started calling afterward, I didn’t answer. We ran into each other again months later, and t…
Mary Poppins was my favorite movie as a kid. I loved her the way kids love a good babysitter ... fun, a little magic, doesn’t yell. I understand her better every year I get older. She never flattered the Banks children or told Mr. Banks what he wanted to hear. She gave whichever medicine each of th…
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