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Your Money Guide on the Side

Why I Buy Stocks at All Time Highs

Your Money Guide on the Side

Tyler Gardner

Business, Education, Entrepreneurship, Investing, How To

4.92.4K Ratings

🗓️ 5 January 2026

⏱️ 34 minutes

🧾️ Download transcript

Summary

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.

Transcript

Click on a timestamp to play from that location

0:00.0

The lesson here isn't don't buy individual stocks. The lesson is don't convince yourself,

0:04.6

you know something about timing the market when you don't. Because the moment you start believing

0:09.4

you're smarter than the collective wisdom of millions of investors around the world, all of whom

0:14.4

have access to the same information, if not more than you do, you're setting yourself up to fail.

0:19.8

This time is different is the most expensive lie you will

0:23.0

ever tell yourself. Hello, friends. This is Tyler Gardner, welcoming you to another episode

0:30.6

of your Money Guide on the Side, where it is my job to simplify what seems complex, add nuance to what

0:36.9

seems simple, and learn from and

0:39.1

alongside some of the brightest minds in money, finance, and investing. So let's get started

0:44.4

and get you one step closer to where you need to be. Hello, everyone, and welcome back to your

0:50.4

money guide on the side. I'm Tyler, and if you're new here, this is the show where we talk about money, investing, and why I'll never leave the beautiful state of Vermont for the one and only reason that they don't allow billboards on the interstate. And if you haven't driven from Massachusetts over the border of Vermont and instantly have gone, wow, something's different here than you're missing out, and that's the best advice I've got for you this week. Today's episode has a title that's going to make some of you immediately

1:16.2

skip to the next podcast in your queue, why I buy stocks at all-time highs. I can already hear

1:22.4

the comments. There's a reason this guy's not a financial advisor anymore. He clearly doesn't

1:27.0

understand markets.

1:28.3

Someone tell him the crash is coming.

1:30.3

And someone tell him that it's all about time in the markets, not timing the markets.

1:34.3

Yeah, I agree with some of what I just mocked.

1:37.3

And here's the thing.

1:38.3

I might not know where markets are going, as none of us do,

1:41.3

but I do appreciate looking at where they've been throughout history

1:46.0

and sharing as many fun takeaways as I can with you so you can officially, and always,

1:51.0

choose your own adventure.

...

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