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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Wendy Li managed billions for New York’s top institutions — here’s what she thinks individual investors can (and should) steal from the pros.

After leading portfolios for the Met Museum, UJA-Federation, and the Mother Cabrini Health Foundation, Wendy now serves as CIO at Ivy Invest. She’s spent decades on the inside — and in this episode she’s walking us through how institutional investors actually make decisions, where regular people go wrong, and what it means to manage risk.

📚What We Discuss with Wendy:

🧠 02:17 — Institutions vs. individuals: why the ultra-wealthy play a different investing game
📉 06:28 — Risk vs. return: are you really being paid for the risk you’re taking?
📚 08:34 — Invest in what you know: learning by doing (and surviving your mistakes)
🪤 11:48 — Career course-corrections: mistakes, pivots, and staying in the game
🤝 15:28 — Trust but verify: what good investor relationships actually look like
💰 18:00 — The luxury of investing: identifying the how and the when to invest
🧾 20:32 — Portfolio allocation: managing your capital with intention
🚪 25:46 — Alternatives and access: knowing your place in a complex market
🕵️ 30:06 — Fund managers: who and how to choose
🛠️ 33:32 — Investing skills: humility, curiosity, and flexibility in the face of risk
🔍 36:58 — Where to learn: insider investment resources
🧰 42:18 — Practical takeaways: frameworks and tools you can use today

💡 What you’ll walk away with

• How institutions manage risk — and how to apply it to your own investing
• Why most retail investors misunderstand returns
• How to think long-term when markets are volatile
• What to ask before trusting a fund manager with your money
• How to approach alternatives without insider access
• The core skills every smart investor needs

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If this episode resonated with you, be sure to check out Episode 15, where Tyler breaks down the 7 steps to identifying your needs for a financial advisor.

What if the most common retirement rule was never meant to be a rule at all?

In this episode, we unpack the origins, flaws, and overlooked nuances of the 4% rule—and why it might not be the best way to plan your financial future. From its fear-based beginnings to its rigid application in a dynamic world, Tyler breaks down 5 key reasons to rethink the 4% rule altogether.

You’ll learn:

Where the 4% rule actually came from (hint: worst-case scenario thinking)

What the Trinity Study really showed—and what most people ignore

How sequence of returns risk can silently wreck your plan

Why portfolio size and asset allocation matter far more than a static percentage

Smarter, more dynamic strategies to adjust year-by-year

If you’ve ever asked, "How much can I safely spend in retirement?"—this one’s for you.

📝 Leave a review if you enjoy the episode or send your thoughts to socialcapconnect@gmail.com. This show is for you, and we want it to be as good as it can be.