I’ve spent 50 years on Wall Street learning about investing, investors, and money. Some of those lessons were easy. Others cost me money. A few changed the way I invested for the rest of my life.
On these broadcasts, I’ll talk about investing, inflation, markets, money, and the mistakes investors make. No complicated formulas and no Wall Street hype — just the lessons I’ve picked up along the way.
Send us Fan Mail You don’t spend what your investments earn. You spend what’s left after the IRS takes its share. In this episode, I walk through the tax problem most investors never think about until April. I explain why waiting a few extra weeks to sell can save real money, how you can owe tax on a fund you never sold, and what to do with your losses. Then I get to retirement, where Social Security and required withdrawals can raise your tax bill in ways most people don’t expect. Tax rules ...
24 Oct 2026
Where Do I Put It. Choosing the Right Retirement Account
Send us Fan Mail Where do you put your retirement money: Traditional IRA, Roth IRA, 401(k), or something else? Most people get stuck on this and do nothing, which is the most expensive choice of all. In this episode, I explain why the order matters more than the account. I start with the one deal no investment can beat, the employer match, then walk through the Traditional versus Roth decision (it’s a tax bet), when an IRA beats your 401(k), and the accounts you may not know about, including ...
17 Oct 2026
Why Most People Retire Poor
Send us Fan Mail Most people don’t retire poor because of the market. They retire poor because of a few small habits that never felt like mistakes at the time. In this episode, I go through five of them: the raise that disappears, the 401(k) cash-out when you change jobs, the permanent car payment, debt that follows you into retirement, and the open checkbook for grown children. I also share one simple rule that keeps all five from happening to you. Nobody offers a retirement loan, so it pays...
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