Talking Real Money - Investing Talk

Smart Enough to Know Better

Don McDonald. Tom Cock

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0:00 | 30:11

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.

Topics
03:46 CEOs, money regrets, and false confidence
08:10 Financial literacy without the stock-picking game
10:21 Tesla hindsight and the bets we didn’t make
11:41 Asset allocation and the cost of being too conservative
15:20 Business owners and concentration risk
17:48 Catching up on retirement saving at 43
21:22 A 60/40 church endowment with a 2.5% draw
23:12 When a robo portfolio badly trails the market
25:35 Dividends, bonds, and rebalancing near retirement

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