“Joe, how much did you spend on your wedding?”
That’s how this episode kicks off, and it sets up the theme running through everything else.
Joe and I help a couple figure out if their plan to retire together in […]
Category: Episodes
#735: He Tried 30+ Side Hustles Before 3 Actually Paid Off, with Cody Berman
Cody Berman was 19 when he learned about financial independence, and 25 when he reached it.
There’s no trust fund here, no lucky exit. Just a brutal train commute, over 30 side hustles, and a gap between what he earned and what he spent that […]
#734: Q&A: Her Brother Owns 3 Houses — Is That Why We Have a ‘Housing Shortage’?
Is there really a housing shortage — or do we just have a lot of wealthy people buying up all the good stuff?
That’s the question kicking off this episode.
Joe and I also help a woman simplify a $1.5 million portfolio she’s managing on her own for the first time.
And we help a […]
#733: The Hidden Math Behind Every Venture Capital Fund, with former Wharton Prof. David Bell
Would you trust someone with your money if the “interview” for the job was a fifty-page pitch deck and a decade-long commitment?
That’s essentially what happens every time someone becomes a limited partner in a venture capital fund.
I sat […]
#732: Why The Customers Nobody Wants Are the Best Ones to Sell To, with David Bell
Why can’t you buy Vegemite in Philadelphia — and what does that have to do with building a wildly profitable online brand?
There are invisible forces shaping what you buy. Where you live. Who’s around you. What your local stores do — […]
#731: Is AI Making You Dumber? With Lorraine Marchand
IQ scores have been sliding since 1970, and Lorraine Marchand thinks AI is quietly speeding that up.
She’s also in the middle of building an agentic AI board of directors for her own company — one she jokes could someday vote to fire her.
Lorraine teaches […]
#730: Q&A: We Have $1.5 Million. Can We Stop Now?
What does it actually mean to have “enough” — and how do you know when it’s time to stop optimizing and start living?
This week’s questions all circle the same tension: how do you keep building financial security without losing the years you’re supposedly securing it for?
[…]
#729: First Friday: Jobs Are Cooling, Prices Are Climbing, and NYC is Freezing the Rent
Why did New York City just freeze rent for a million apartments — and who’s actually going to pay for it?
This month’s economic landscape is anything but simple: a job market that’s cooling faster than expected, a brand-new Fed chair rewriting the rulebook, and a policy […]
#728: Q&A: What $2.4 Million at 37 Actually Looks Like (It’s Not What You Think)
What happens when a sudden $850,000 inheritance turns into eight different account balances, three rental properties, and one very big decision about your future?
When grief, real estate, and a six-figure windfall collide all at once, the fastest way to make an expensive mistake is to rush […]
#727: Hope Isn’t a Feeling. It’s a Skill. – with Dr. Julia Garcia
What if the biggest thing standing between you and your financial goals isn’t your income, your debt, or the housing market — but your own brain?
Dr. Julia Garcia is a psychologist, behavioral researcher, and author of The Five Habits of Hope — and she’s spent years studying why […]
