Your Money Guide on the Side 3 Reasons You’ll Never Beat the Stock Market
And in case you missed it, check out last week's episode of Your Money Guide on the Side where we answered the question, What do Billion Dollar Portfolios Look Like?
Let’s be honest: you’re not going to beat the stock market. And that’s not an insult — it’s a liberation. In this episode of Your Money Guide on the Side, Tyler Gardner unpacks one of the most misunderstood goals in investing: trying to “win” against the market.
Drawing on decades of investing experience (and more than a few Peloton mistakes), Tyler explains why comparing yourself to the S&P 500 is often irrelevant, how hedge funds and high-frequency traders have rigged the game against retail investors, and most importantly, why even when you do win, you often lose.
We explore:
- The real origin of the “beat the market” mindset — and why it was never about helping you
- Why the S&P 500 isn’t a fair benchmark for most people
- Market efficiency theory explained without Greek letters (but with plenty of sarcasm)
- Behavioral biases that will ruin your returns: overconfidence, recency bias, loss aversion, confirmation bias, and more
- How even the pros struggle — and why surviving your own brain is the real edge
- When paying a 1% advisor fee might actually be a bargain
- Why boring, automated, diversified investing is the best strategy no one wants to hear about
Whether you're new to investing or already deep in the weeds of candlestick charts and YouTube stock tips, this episode will reframe what success really looks like. Because real wealth isn’t built by outsmarting others — it’s built by staying in the game.
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