Podcast Episodes
Back to SearchBreak 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…
1 month, 3 weeks 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…
1 month, 3 weeks 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…
1 month, 3 weeks 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,…
1 month, 3 weeks 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…
1 month, 3 weeks 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…
1 month, 3 weeks 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…
1 month, 3 weeks 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…
1 month, 3 weeks ago
From Drive-Through Customer to Company Owner
Episode 260
From Drive-Thru Customer to Company Owner: The Lunch Money Shift
What if the money you already spend every week at drive-thrus, coffee shops, and gas…
1 month, 3 weeks ago
Thirteen Principles for Podcasts and Portfolios
Episode 259
The Thirteen Principles for Podcasts and Portfolios: Blueprint Meets Garden
What happens when a rigid business blueprint designed for digital indepen…
1 month, 3 weeks ago