Podcast Episodes
Back to SearchHidden Traps in Your Robinhood Account
Episode 408
AI HOST FOCUS PROMPT — Hidden Traps in Your Robinhood Account
Create a conversational, educational Trail Boss Radio episode titled “Hidden Traps in Y…
1 month, 3 weeks ago
Statistical Models for Core Satellite Crypto Portfolios
Episode 405
Trail Boss Radio: Statistical Models for Core Satellite Crypto Portfolios
Every trail needs a core and a scout. In this episode, the Trail Boss bre…
1 month, 3 weeks ago
Professional Stock Research for Your Roth IRA
Episode 397
Professional Stock Research for Your Roth IRA
What if you could research stocks for your Roth IRA using the same basic process professional investors…
1 month, 3 weeks ago
Avoid the Social Security Tax Torpedo
Episode 404
Avoid the Social Security Tax Torpedo
One extra $1,000 withdrawal. That's all it takes to accidentally hand the IRS an effective tax rate of over 40%…
1 month, 3 weeks ago
2026 Roth Rules Protect Social Security
Episode 403
2026 Roth Rules Protect Social Security
There's a quiet reason Roth accounts get called the crown jewel of retirement planning — and it has nothing t…
1 month, 3 weeks ago
Consolidate Your Scattered 401k Accounts
Episode 398
Consolidate Your Scattered 401(k) Accounts: Take Control of Your Retirement Money
What happens to your 401(k) when you change jobs?
For many people, …
1 month, 3 weeks ago
Robinhood s 3 Percent IRA Match Fine Print
Episode 399
Robinhood's 3% IRA Match — And Why Your Beneficiaries Need Attention Too
A 3% match on your IRA sounds like free money — and technically, it is. But …
1 month, 3 weeks ago
Build an Automated ETF Cash Machine
Episode 394
Build an Automated ETF Cash Machine
What if your investments could become your own automated cash register—working 24 hours a day, whether you're at …
1 month, 3 weeks ago
Avoid the 20 Percent Rollover Tax Trap
Episode 395
Avoid the 20% Rollover Tax Trap
What if one simple mistake during a retirement rollover could turn your hard-earned savings into an unnecessary tax b…
1 month, 3 weeks ago
How to Survive the Compounding Mud
Episode 393
How to Survive the Compounding Mud
Every successful investor has to make it through the Compounding Mud—that frustrating season when you're investing…
1 month, 3 weeks ago