Investing isn’t a game, and treating it like one can quietly sabotage your future. This episode dismantles the idea of “trying out” investments or advisors the way Wall Street has trained people to do for decades. Don and Tom argue that real financial advice starts with planning, not products, and that a true fiduciary focuses on taxes, portfolio design, and long-term goals — not beating markets or selling what’s hot. Listener questions tackle portfolio overlap inside a 401(k), when simplicity beats customization, the reality behind so-called “Trump accounts” for children, and how to evaluate companies like Corbridge Financial in teacher retirement plans. The show wraps with a reality check on World Cup ticket pricing that somehow makes active management look affordable by comparison. 0:04 Why “trying out” investments makes no more sense than test-driving surgery 1:26 The danger of treating investing like a game 2:29 How Wall Street gamified investing for nearly a century 3:45 What good advisors don’t promise 4:10 Fiduciary planning versus transactional sales 5:14 Marketing narratives vs. real financial planning 6:55 Why big advisory firms spend fortunes on persuasion 7:48 Hot returns, sexy funds, and why chasing them fails 8:35 Investing to win vs. investing to reach a goal 9:56 Accepting market reality instead of competing with billionaires 11:27 Product versus planning — the core distinction 12:09 Listener question: fixing portfolio overlap inside a 401(k) 14:34 Why simpler portfolios usually work better 15:09 Using target-date funds to eliminate overlap and rebalancing headaches 16:19 What “Trump accounts” actually are — and what they aren’t 18:39 Comparing Trump accounts to 529 plans 21:38 Corbridge Financial: when it’s fine and when it’s a trap 23:01 Appreciating listeners everywhere (yes, even Portland) 24:40 World Cup ticket prices that defy financial gravity Learn more about your ad choices. Visit megaphone.fm/adchoices