The Pete the Planner® Show

Affluent Americans just raised their retirement target 26% in one year, to $2.6 million - and most actual millionaires still don't feel wealthy. Pete and Damian dig into what Americans say they need, why the goalpost keeps moving, and what people say actually makes them feel rich (hint: it isn't just money). Plus the $185,500 health bill nobody budgets for, what Social Security's 2034 deadline really means, and the results of our LinkedIn poll.

What if you could spend your stock-market gains without selling your stocks? This week, Pete and Damian unpack the "buy, borrow, die" strategy: how wealthy investors turn portfolios into spending money, why banks love the arrangement, and what happens when the market stops cooperating. Is it smart planning, a rich person's cheat code, or a very expensive way to discover that debt is still debt?

What if the purpose of some of your money is to buy fewer financial worries? This week, Pete, Dame, and Kristen explore annuities through one central idea: you can pay an insurance company to take on certain risks. We’ll explain the basics, compare the types and costs, and weigh the tradeoffs of exchanging flexibility and growth potential for greater certainty.

Your house has gone up in value. Your checking account hasn’t. Now a company is offering you cash from your home equity—with no monthly payments. Home Equity Investments promise access to housing wealth without another monthly bill. But what do you surrender in exchange, and where will the money come from when it’s time to settle up? Pete, Dame, and Kristen examine how these agreements work, what the numbers can look like, and whether turning home equity into spending money solves a financial p

Traditional retirement advice has encouraged investors to gradually reduce risk as they approach retirement. But with retirements potentially lasting 30 years or longer, inflation threatening purchasing power, and retirees increasingly responsible for generating their own income, is that advice still appropriate?

“We’ll pay for college” is easy to say when your kid is wearing diapers. What happens when they pick a private school, change majors, or need a fifth year? This week, we tackle three listener questions about how much to save, where parents can draw the line, and what to do when a college promise threatens retirement.