Podcast Episodes
Back to SearchOwn Your Business and the Cash Register
Episode 273
Own Your Business and the Cash Register: Digital Sovereignty for Side Hustles
Stop renting your business on someone else’s platform. In this powerful…
3 months, 1 week ago
Retirees as Sovereign Digital Operators
Episode 272
Morningstar June 2026 Best Dividend Stocks: Moats vs. Traps
High headline yields look tempting — but they often hide serious risks. In this detailed …
3 months, 1 week ago
Break Generational Cycles with Dividend Stocks
Episode 269
Break Generational Cycles with Dividend Stocks: The PeeWee League Strategy
What if the key to breaking your family’s cycle of living paycheck to pa…
3 months, 1 week ago
How VOOV Compounds Your Lunch Money
Episode 267
How VOOV Compounds Your Lunch Money: The Tortoise vs. Hare Strategy
What if your lunch money could quietly build wealth while you sleep — even when f…
3 months, 1 week ago
Build Wealth with $25 a Week
Episode 268
Build Wealth with $25 a Week: The Grandfather’s Porch Talk on Long-Term Discipline
Imagine sitting on the back porch with your grandfather on a qui…
3 months, 1 week ago
Why 778 Dividend Yields are Traps
Episode 266
Why 7-8% Dividend Yields Are Traps
If a dividend yield of 7% or 8% sounds too good to be true — it usually is.
In this episode of Trail Boss Radio,…
3 months, 1 week ago
Stop Paying Rent to Digital Landlords
Episode 265
Stop Paying Rent to Digital Landlords
Every time you build your audience on
someone else's platform — every post,
every follower, every video, ever…
3 months, 1 week ago
The Trail Boss Investment Operating System
Episode 264
The Trail Boss Investment Operating System
What if investing worked more like baseball?
In this episode of Trail Boss Radio, we introduce The Trail B…
3 months, 1 week ago
Building a Digital Empire After 65
Episode 262
Become a Stakeholder for Just Five Dollars: The First Step to Ownership
What’s really stopping you from investing? Most people say “I don’t have enou…
3 months, 1 week ago
Become a Stakeholder for Five Dollars
Episode 261
Become a Stakeholder for Just Five Dollars: The First Step to Ownership
What’s really stopping you from investing? Most people say “I don’t have enou…
3 months, 1 week ago