Ep. 1961: Smart Enough to Know Better

Being great at running a company does not make anyone a market oracle. Don and Tom unpack the money regrets of successful CEOs—and the costly confidence that often follows success.They draw the line between business skill and investment skill, explain why financial literacy matters, and make the case for diversification over hindsight, stock-picking games, and concentrated bets.Then they turn to listener questions on catching up at 43, investing a church endowment, an underperforming robo portfolio, and where stock dividends should go near retirement.Topics03:46 CEOs, money regrets, and false confidence08:10 Financial literacy without the stock-picking game10:21 Tesla hindsight and the bets we didn’t make11:41 Asset allocation and the cost of being too conservative15:20 Business owners and concentration risk17:48 Catching up on retirement saving at 4321:22 A 60/40 church endowment with a 2.5% draw23:12 When a robo portfolio badly trails the market25:35 Dividends, bonds, and rebalancing near retirementQuestions? Comments? Click!