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Your Money Guide on the Side

Your Money Guide on the Side

By: Tyler Gardner
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About this listen

Your go-to podcast for mastering money and investing. Hosted by Tyler Gardner, a trusted influencer with over 2.5M 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.

© 2025 Your Money Guide on the Side
Economics Leadership Management & Leadership Personal Finance
Episodes
  • Ep 21 - How Much Can I Spend in Retirement? Why the 4% Rule Gets it Wrong
    Jun 23 2025

    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.

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    27 mins
  • Ep 20 - JL Collins - The Simple Path to F-You Money (And Why You Need to Ask Your Boss for a Paid Leave Today)
    Jun 16 2025

    Today’s guest is someone whose work has quietly and profoundly shaped how a generation thinks about money. JL Collins is the author of The Simple Path to Wealth, a personal finance classic that has empowered hundreds of thousands to think differently about investing, independence, and freedom.

    In this conversation, JL and I explore the real meaning behind financial independence — not retiring early, but reclaiming your ability to say no. We go back to the moments that shaped his life philosophy: the bold four-month leave he took just two years into his first job, the decision to convince his wife to leave her job while he wasn’t earning a paycheck, and the early desire to build what he calls FU money — not to quit work, but to buy back control.

    We revisit Black Monday in 1987 and how that shaped JL’s views on market volatility, risk, and emotional discipline. He shares how a humbling mistake helped hardwire the importance of staying the course, and how index investing eventually became the core of his life’s message: simplify.

    We also talk about the new edition of The Simple Path to Wealth, what’s changed, what hasn’t, and how his daughter went from being the reluctant listener to co-pilot on the updated edition.

    This is a conversation about money, yes — but more than that, it’s about living deliberately. JL reminds us that wealth isn’t about what we can afford — it’s about what we no longer have to worry about.

    You’ll hear about:

    • How JL built his investing philosophy through trial and error
    • Why VTSAX and chill remains his core guidance
    • What it means to live in a world where, eventually, everything is "free"
    • Why simplicity is a radical act in a noisy, complex world

    And why, if you get the money stuff right early, you can spend the rest of your life not thinking about it at all.

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    46 mins
  • Ep 19 - The 10 Rules of Not Getting Screwed When Buying or Leasing a New Car
    Jun 9 2025

    Car buying has become one of the most financially dangerous consumer experiences in modern life. In today’s episode, we’re flipping the script.

    Whether you’re buying or leasing, trading in or paying cash, I’ll walk you through the 10 timeless rules you must follow if you want to avoid getting taken for a ride—financially and emotionally. No guilt trips. No boomer advice. Just strategy, leverage, and power dynamics decoded.

    And full disclosure: I love cars. I lease new ones every few years. I’m not here to shame your joy. I’m here to make sure that joy doesn’t cost you $9,000 more than it should.

    WHAT WE COVER:

    • Why you should never walk into a dealership first—and what to do instead
    • The email script that can save you thousands before you ever test drive
    • Why “What can you afford monthly?” is a trap—and how it costs you big
    • The hidden revenue center called the “finance office” (and how to say no)
    • The floor plan secret that gives you leverage when buying in stock
    • How to use pre-approved financing as bait to beat the dealer at their own game
    • Real math on depreciation—and why some “investments” are worth it anyway
    • When leasing makes more sense than buying (and what to negotiate)
    • How emotional timing ruins deals—and how to buy before you need to
    • The best days of the year to buy, based on actual dealer incentives

    Plus, why your car purchase might be one of the biggest financial decisions of your next five years—whether you realize it or not.

    MENTIONED IN THIS EPISODE:

    • Kelley Blue Book average car prices (2024): $47,000+
    • CFPB, NADA, JD Power, Bankrate statistics on car loans, dealer profit centers, and interest rate games
    • How to calculate a lease “money factor” and negotiate like a pro
    • The difference between buying a car and buying a feeling—and why that matters

    JOIN THE CONVERSATION:
    Have a question, a rant, or a car-buying story that others need to hear? Shoot me a note at socialcapconnect@gmail.com. I read every message.

    And if this show is helping you feel more powerful and prepared, the best way to say thanks is with a quick review. It helps the show grow and lets me keep delivering practical, real-world financial guidance—without selling out.

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    34 mins
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