How to Money · Friday, July 31, 2026
The hosts dismiss the investing advice 'buy low and sell high' as virtually impossible to execute successfully. They argue that trying to time the market often leads to missed gains and recommend dollar-cost averaging, emphasizing regular investing regardless of market conditions, as a more reliable strategy for long-term wealth building.
“But one of them we would say is buy low and sell high. And I feel like you hear in a down market, you hear more people talking about that, buying the dip, that kind of stuff. And again, Matt, kind of like what you said with the ten percent things, like this is kind of sort of good advice, like there's a nugget of wisdom here, but there's also the fact that this piece of advice could completely mess you up, and it's just not possible really to buy low and sell high, is what we would say.”
“Stats show year after year that even professional fund managers consistently underperform the simple strategy of buying straight up index funds. And these are people that are highly compensated, right that this is their job to attempt to outperform the market to get outside returns. But the reality is that trying to buy the dip means you're waiting on stock prices to go down, and the truth is stocks are mostly on an up into the right trajectory, right, that is the overwhelming direction that they're heading.”
“And so that's why we prefer we advocate the dollar cost averaging approach, mostly ignoring current market conditions because your cash sitting on the sidelines while you're trying to buy, the dip is experiencing opportunity costs and it's just being smacked around by inflation and today. So we would say just keep buying. Don't worry about timing the market. The key is to get your money in the market with regularity.”