Money School Podcast
1) The Ultimate Investing Advantage Is…Boredom w/ Irwin Boris
Most investors never question the structure they're investing in. They accept tight assumptions, back-end-heavy returns, and illiquidity as the price of access, assuming the payout will arrive before ...Show More
2) How to Stop Carrying Real Estate Risk and Still Make Money w/ Scott Jelinek
Most investors never question the hierarchy they're operating in. They borrow money, take on operational risk, manage tenants, absorb volatility, and send a large portion of every payment upstream to ...Show More
3) Either/Or Investing Is Destroying Your Wealth w/ Caleb Guilliams
One of the biggest mistakes in personal finance is how quickly conversations turn into either/or debates. Invest or insure, trust the market, or play defense. Something is a scam, or it's the answer. ...Show More
4) Money Has Feelings: Why Wealthy People Still Feel Miserable w/ Shannon Ryan
Many people who work hard to build and protect their wealth assume that once they "make it," everything will finally feel good, secure, calm, and settled. But most people don't discover the truth unti...Show More
5) Mistakes That Take Wealthy People Out in a Downturn w/ Arthur Hood
When people think about economic downturns, they usually assume the damage happens at the bottom. What rarely gets talked about is how many wealthy people lose everything — not because they didn't hav...Show More
6) The Trucker Financial Trap and How to Escape It w/ Dexter Holiday
For a lot of truckers, you can make great money hauling loads across the country, but it comes with a catch: the wheels have to keep turning for the money to keep coming in. There's no automatic runw...Show More
7) What Most Entrepreneurs Get Wrong About Selling Their Business w/ Gregory Kovsky
When entrepreneurs think about selling a business, they picture a clean formula: EBITDA × multiple, a "strategic buyer," and a smooth six-month process that ends with a big wire hitting their account....Show More
What Most Entrepreneurs Get Wrong About Selling Their Business w/ Gregory Kovsky
39:01 | Dec 4th, 2025
8) The Smartest Money Move You've Never Considered w/ Dr. Jeff Seibert
When people think about wealth-building, they picture stock charts, IRR calculators, and "smart" portfolios engineered by advisors. What they never picture is a dentist quietly building long-term weal...Show More
9) How to Escape the Debt Cycle the Banks Want You Trapped In w/ Harrison George and Christy Vann
For most people, debt isn't a mistake; it's just life. The mortgage, the car loan, and the credit cards are what everyone does. Making the minimum payments feels normal, but that actually keeps people...Show More
10) Non-Food Franchises: A Shortcut to Entrepreneurship, Wealth & Tax Benefits w/ Jon Ostenson
When people hear "franchise", they immediately picture a drive-through window and a fryer in the back. That narrow view hides one of the most accessible and profitable paths to business ownership toda...Show More