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 […]
Category: Episodes
#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 […]
#726: Q&A: She Has $884K Saved — So Why Can’t She Retire?
What happens when you look at a $862,000 portfolio and realize early retirement might actually be out of reach?
When a mountain of ticker symbols, account balances, and unexpected life updates come hitting you all at once, your money plan can quickly start to look like a complete mess.
#725: What Most Families Get Wrong About Passing Down Wealth, with Andrea Baumann Lustig
When it comes to our money, the things we feel most certain about are often the exact blind spots that quietly derail our long-term plans.
We hold onto financial beliefs as if they’re religion or politics, rarely checking if they actually serve our long-term legacy goals.
Veteran […]
#724: Why Does Every Good Idea Die in a Meeting? – with HBS Prof Linda Hill and Jason Wild
What does it actually take to build a business that can routinely innovate without imploding?
Most of what we are taught about traditional, top-down leadership is completely wrong when it comes to driving innovation.
True innovation isn’t about having a single visionary leader who commands a room—it’s about creating […]
