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Ryan was proud. He had just bought a stock, and he wanted me to be impressed. He didn’t know much about the company, but he was sure it would make lots of money. I suspect it was really about the fun of having something to talk about.

I suggested an S&P 500 index fund. He nodded politely, and I haven’t heard from him since.

In this episode, I use Ryan’s story to talk about teaching money to young people. I explain why telling them “don’t” doesn’t work, and what to do instead. It’s a simple two-bucket approach, plus three questions that let a young person find the holes in their own thinking.

If you have a child or grandchild, or you were once a young person who bought a stock because it was exciting, this one is for you.

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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 change, so check the numbers before you act. The principles last.

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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 the SEP-IRA, Solo 401(k), 403(b), and the HSA. I also cover three mistakes that cost people more than picking the wrong account.

You don’t need to be clever. You just need to start.

Have a question or a topic you’d like me to cover? Leave me a message in Fan Mail.

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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 to get this right early.

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The safest investment in America has a government guarantee, a pen on a chain, and an interest rate of one percent. I explain what that guarantee actually promises (your dollars, not what they can buy), why an account can go up while you get poorer, and why the fear of losing money in stocks is real but aimed at the wrong target.

You don't have to get over your fear. You just have to match the money to the time. Money you need soon gets a boring, safe home. Money you won't touch for years gets a job.

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You saved for forty years. You avoided the stinkers. You bought the index fund and left it alone. Then you retired, and the fear showed up anyway: "When will I run out of money?"

In this episode, I explain why that fear hits hardest after the paychecks stop, even for people who did everything right. Nobody can tell you the date, but you can build a system that keeps you from being forced to sell in a bad market. I walk through how to give yourself a paycheck again, why a cash cushion matters, and why you should decide your bad-year rules before the bad year arrives.

You may not get certainty, but you can get shorter phone calls.

If you'd like to comment on this episode, or request a subject for a future podcast, leave me a message in Fan Mail. I read every one.

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Retirement planning doesn't need a spreadsheet with forty variables. It comes down to about five numbers, and you can work them out on the back of an envelope.

In this episode, I walk through what you spend, what's already guaranteed, and how to find your gap. I also show what waiting ten years to start saving really costs, and the one place where waiting actually pays you.

Your assignment is one envelope and about ten minutes.

If you'd like to comment on this episode, or request a subject for a future podcast, leave me a message in Fan Mail. I read every one.

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What are you actually buying? If your answer is a ticker symbol, a tip from your brother-in-law, or a stock that "used to be forty dollars," this episode is for you.

Ben Graham's idea was simple: a stock is a piece of a real business, and price is not the same thing as value. In this episode, I explain why that difference matters, how cheap stocks turn into value traps, and why the market's bad days are usually mood, not business.

I'll also tell you about a retired schoolteacher who came to my office with a highlighted newsletter and a very strong stock tip, and I'll give you the one-sentence test to use before you buy anything.

You don't have to pick stocks to think like a value investor. You just have to know what you're paying for.

Have a comment or a topic request? Leave me a message in Fan Mail. I read every one.