Why I Buy Stocks at All Time Highs

Here are some truly helpful resources from this week's sponsors: First, the ONLY way I am able to make this much content, day in day out, is by feeling my best. Always. And that starts with my working out each morning and needing something that doesn't leave me feeling like I just ate four pounds of candy. Enter LMNT. It is literally the product designed for people like me: need the fuel, don't need the crash, game on. Check out LMNT today here. And if you're looking to start 2026 with a bang, like, a "get my act together financially once and for all" type bang, check out Facet. They continue to practice what I preach, and they provide real advice from real experts for real people. Check them out today here. And now on to this week's the show notes! Most people say they believe in long-term investing. Far fewer people actually behave like it — especially when markets are at all-time highs. In this episode, Tyler tackles one of the most common (and expensive) investing mistakes there is: sitting in cash while waiting for the “right time” to invest. The twist? That “right time” almost never shows up, and the data is brutally clear about what it costs. Despite how uncomfortable it feels, buying stocks at all-time highs has historically been a perfectly reasonable — and often superior — strategy compared to waiting on the sidelines. In this episode, Tyler walks through five reasons why staying in cash is costing you a fortune: All-time highs are normal — markets hit them far more often than most people realize Even terrible timing beats no timing — buying at the worst possible moments still outperforms sitting in cash “This time is different” almost never is, no matter how convincing the headlines sound Missing the best days destroys long-term returns, and those days often arrive during chaos Doing nothing is still a decision — and it carries real risk Along the way, Tyler breaks down decades of market history, real return data, and behavioral traps that convince smart people they’re being cautious when they’re actually sabotaging themselves. This episode isn’t about ignoring risk or investing recklessly. It’s about recognizing that waiting for certainty is just another way to lose money. Markets go up. Markets go down. But sitting in cash while hoping to outsmart two centuries of economic progress has never been a winning strategy. If you’ve ever told yourself you’re “just waiting for a pullback,” this episode is for you. And if this helped you rethink your approach — or finally get out of your own way — leaving a quick review on Apple Podcasts or Spotify genuinely helps. It helps other people find the show and keeps this whole thing moving. As always, hope this gives you something useful to think about this week.