Is Future Planning Ruining Your Future?

What if your financial advisor told you to spend your money now?
To give away your inheritance early?
To go on more vacations?
To prioritize experience over investment?

What if they told you the only inflation-protected asset is experience?

Bill Perkins is a hedge fund manager, poker player, and author of the bestseller Die With Zero. On this week’s episode, he breaks down why money is just a means — and experience is the end.

📚 What We Discuss with Bill Perkins:

🛤️ 02:40 — Early revelations and going the non-traditional route
💡 05:10 — Borrowing from your poor self to give to your rich self
📆 07:35 — “What experiences belong when?” — and why delayed gratification can go too far
🤔 10:25 — What money can really buy — fulfillment vs. accumulation
🎢 12:22 — Staple experiences worth the cost — collecting memories that stick
🧠 13:35 — Memory dividends — the one return no market crash can erase
👵 15:40 — Retirement planning — running out of money vs. running out of time
🧘 17:50 — Letting go — why overplanning for the future can wreck the present
🕰️ 20:25 — “Life is now, life is urgent” — estate planning and missed chances
🏛️ 23:20 — When should inheritance be inherited? Challenging default thinking
🎯 26:15 — Hindsight and financial regret — is gold-plated better than good enough?
📖 28:20 — Learning from the past to make the most of what’s next
💸 29:20 — What is your time worth? The hidden cost of chasing more income

💡 What You’ll Walk Away With

• Why deferring joy is often just fear in disguise
• A new way to think about saving, giving, and legacy
• How to measure value through memory, not money
• A framework for spending intentionally at different life stages
• How to plan for the end of life without missing the middle

🧾 Resources Mentioned

• Die With Zero by Bill Perkins → https://a.co/d/9KKHOzT
• Your Money or Your Life by Vicki Robin and Joe Dominguez → https://yourmoneyoryourlife.com

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If you enjoyed this, check out episode 22 with Wendy Li — a former endowment CIO who managed billions for New York’s top institutions and shared how institutional investors evaluate risk, choose fund managers, and build resilient portfolios.

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

If you're game to support the show, leaving a quick review really helps — even one sentence goes a long way!

You can also join thousands of others investment minded individuals in subscribing to my newsletter here.

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.