Your Money Guide on the Side
Your Money Guide on the Side
Podcast Description
Your go-to podcast for mastering money and investing. Hosted by Tyler Gardner, a trusted influencer with over 2M followers, Your Money Guide on the Side simplifies the complex, adds nuance to what seems simple, and connects you with the brightest minds in finance, investing, and business. Whether you’re just starting or leveling up, this is your one-stop resource to navigate your own finances with clarity, confidence, and a bit of fun. Let’s get you one step closer to where you need to be.
Podcast Insights
Content Themes
The podcast covers financial literacy, investment strategies, emotional resilience in investing, and optimizing personal finances, with episodes like Political Nonsense exploring the impact of political events on market behavior and TikTok Bans discussing the importance of diversifying income streams. The show emphasizes long-term investing principles and emotional awareness to navigate market volatility.

Your go-to podcast for mastering money and investing. Hosted by Tyler Gardner, a trusted influencer with over 3M followers, Your Money Guide on the Side simplifies the complex, adds nuance to what seems simple, and connects you with the brightest minds in finance, investing, and business. Whether you’re just starting or leveling up, this is your one-stop resource to navigate your own finances with clarity, confidence, and a bit of fun. Let’s get you one step closer to where you need to be.
Here are some truly helpful resources from this week’s sponsors:
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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.

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