Podcast Episodes
Back to SearchHow AI Accelerates Digital Enshittification
Episode 297
How AI Accelerates Digital Enshittification
Artificial Intelligence is changing the world at an incredible pace.
It can help us learn faster.
Build b…
2 months, 4 weeks ago
How VTWO VNQ and NETL Build Wealth
Episode 314
How VTWO, VNQ, and NETL Build Wealth
Trail Boss Dan Johnson breaks down three lesser-known but powerful pieces of the wealth-building puzzle: small-c…
3 months ago
The Mechanics of the Russell 2000 Index
Episode 301
The Mechanics of the Russell 2000 Index: Inside the Trail Boss Minor Leagues of the Stock Market
Imagine the minor leagues of baseball — raw, unpre…
3 months ago
Why Warren Buffett Recommends Index Funds
Episode 300
Why Warren Buffett Recommends Index Funds (The Ultimate Irony)
What if the greatest stock picker in history actively tells everyday investors not t…
3 months ago
Wait 60 days Before Trading Crypto
Episode 313
Meme Coins Explained: Hype, Humor, and High Risk
What exactly is a meme coin?
Why do some cryptocurrencies become worth billions of dollars even thou…
3 months ago
Consistent Investing Beats Midterm Election Volatility
Episode 311
Consistent Investing Beats Midterm Election Volatility
Every election cycle seems to bring the same predictions.
"The market is going to crash."
"Eve…
3 months ago
Moving Robinhood Crypto to Ryder One.
Episode 310
Moving Robinhood Crypto to Ryder One
Do you really own your cryptocurrency if it's sitting on an exchange?
Or do you simply have access to it until y…
3 months ago
Arlington World Cup Walk Zone Lodging
Episode 309
Arlington World Cup Walk Zone Lodging
What if the most valuable real estate during the 2026 FIFA World Cup isn't a luxury hotel...
It's a place withi…
3 months ago
The Life cycle of Enshittification
Episode 296
The Life Cycle of Enshittification
Why do so many great products seem to get worse over time?
Why do platforms that once put customers first graduall…
3 months ago
Arlington World Cup Lodging and Logistics
Episode 308
Arlington World Cup: Lodging, Logistics, and Opportunity
The 2026 FIFA World Cup isn't just the world's biggest sporting event.
For entrepreneurs, se…
3 months ago