Ep 23 - The 3 Reasons You’ll Never Beat the Market (And Why That’s Okay)
Mon, 07 Jul 2025
Let’s be honest: you’re not going to beat the stock market. And that’s not an insult — it’...
Ep 22 - Wendy Li - The Secret Strategies of Billion-Dollar Portfolios
Mon, 30 Jun 2025
Wendy Li managed billions for New York’s top institutions — here’s what she thinks individual ...
Ep 21 - How Much Can I Spend in Retirement? Why the 4% Rule Gets it Wrong
Mon, 23 Jun 2025
What if the most common retirement rule was never meant to be a rule at all?In this episode, we unpa...
Ep 20 - JL Collins - The Simple Path to F-You Money (And Why You Need to Ask Your Boss for a Paid Leave Today)
Mon, 16 Jun 2025
Today’s guest is someone whose work has quietly and profoundly shaped how a generation thinks abou...
Ep 19 - The 10 Rules of Not Getting Screwed When Buying or Leasing a New Car
Mon, 09 Jun 2025
Car buying has become one of the most financially dangerous consumer experiences in modern life. In ...
Ep 18 - Mady Mills - Why Billionaires Panic, What Men Need to Hear, and the One Account that Buys Your Financial Freedom
Mon, 02 Jun 2025
She’s been on Bloomberg. The New York Times. Yahoo Finance. But Mady’s real talent? Translating ...
Ep 17 - How I Would Invest $1,000,000 - 3 Approaches, 3 Stories, and 1 Question to Simplify Your Life
Mon, 26 May 2025
You've hit the million-dollar mark—now what?In this episode of Your Money Guide on the Side, ...
Ep 16 - Andrew Tobias - The Only Investment Interview You Will Ever Need (And How Money CAN Buy Happiness)
Mon, 19 May 2025
What if the only investment guide you ever needed... actually was?This week, I sit down with persona...
Ep 15 - Should You Hire a Financial Advisor? (And 7 Things to Look For If You Do)
Mon, 12 May 2025
This might be the most common money question I get, and maybe even the most important: Should I hire...
Ep 14 - Dan Brigham - On Faith, Finance, and First Principles
Mon, 05 May 2025
He paid off $100K in debt and isn’t trying to sell you a thing — meet Dan the Budget Man.In a fi...
Ep 13 - The Truth About Debt: How to Use It, Beat It, and Stop Feeling Bad About It
Mon, 28 Apr 2025
Is All Debt Bad? What the Wealthy Know That Most People Don’tDebt doesn’t have to be your enemy—...
Ep 12 - Andy Schneider - The Educator’s Guide to Money, College, and Real-World Finance
Mon, 21 Apr 2025
What happens when a former English teacher becomes a CFO—and decides to teach everyone around him ...
Ep 11 - The 3-Step Framework for Solving Any Financial Problem (That's Actually Worth Solving)
Mon, 14 Apr 2025
Have you ever said, “I’m just bad with money”?Yeah—me too. But what if the real issue isn’...
Ep 10 - Victoria Ferguson - On Money, Meaning, and Saying No to Budgets
Mon, 07 Apr 2025
What do you get when you combine a financial planner with the heart of a teacher and the boldness of...
Ep 9 - On Playing to Win (The Asymmetry of Opportunity)
Mon, 31 Mar 2025
Most people spend their lives trying not to lose. The wealthy? They play to win.In this solo episode...
Ep 8 - Jessica Inskip - On Leaving Wall Street, Fighting Misinformation, and Redefining Financial Education
Mon, 24 Mar 2025
This week on Your Money Guide on the Side, I’m joined by the incredible Jessica Inskip—one of th...
Ep 7 - Killing Sacred Cows of Personal Finance, Or, Why I (Really) Don't Love Bonds
Mon, 17 Mar 2025
Bonds have been a staple in portfolios for decades, often hailed as the “safe” investment that b...
Ep 6 - Mike Taormina - Cutting Through Crypto Noise, and a Case for Active Portfolio Management
Mon, 10 Mar 2025
Back in 2003, I met Mike Taormina at the London School of Economics, never expecting we'd stay ...
Ep 5 - Political Nonsense, the Integrity of Markets, and Broken Clocks as Great Investors
Mon, 03 Mar 2025
In this week's episode, we explore our common tendency to react emotionally to political electi...
Ep 4 - Patrick Wetherille - Managing Detractors, Working from Anywhere, and Optimizing our Finances and our Lives
Fri, 28 Feb 2025
My guest this week, Patrick Wetherille, shares a little bit about his experience with optimizing lif...
Ep 3 - TikTok "Bans," Email Musts, and Building Resilience for the Inevitable Storm
Fri, 28 Feb 2025
In this episode, I explore the power of diversifying communication channels, income streams, and the...
Ep 2 - Market Crashes, Awkward Neighbors, and Overcoming Angel's Landing
Fri, 28 Feb 2025
In this episode, I do my best to touch on the absolute musts of investing and controlling our emotio...
Ep 1 - Starting With Why
Fri, 28 Feb 2025
I am thrilled to offer a brief glimpse into the "why" behind building out the podcast. The...