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Your Money Guide on the Side

Tyler Gardner
Your Money Guide on the Side
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5 of 36
  • 10 Ways Investors Lose Money Without Knowing It
    Most portfolios don’t implode in one dramatic crash; they leak slowly. A percent here, a hidden fee there, and before you know it, your retirement fund has been funding someone else’s yacht. (Cough, cough...your advisor's...)In this episode, I shine a light on ten common wealth leaks that quietly drain portfolios, plus practical fixes for each one.We’ll cover:How a “tiny” 1% fee can cost you a third of your returns.Why overtrading turns your portfolio into Swiss cheese.The real silent killers: taxes, spreads, and cash drag.Why your own emotions can be more expensive than any advisor.You’ll walk away with a checklist to plug the holes, lower your costs, and keep more of your money compounding where it belongs — in your account, not Wall Street’s.👉 Think of this episode as financial plumbing: we’re finding the leaks before they flood your future. 
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  • The Only Asset Allocation Guide You’ll Ever Need
    Your portfolio’s performance isn’t about finding the next hot stock; it’s about how you slice the pie. In this episode, I break down the real math behind compounding, why losses hurt more than wins help, and three simple allocation models you can actually follow without losing sleep.We’ll cover:Why “average returns” are misleading and compounding is what matters.How diversification really works (hint: it’s not about guessing winners).Three practical allocation strategies for different levels of risk tolerance.The surprising case for the “reverse glide path” in retirement.Whether you’re cautious, balanced, or adventurous, you’ll leave with a framework to match your investments to both your spreadsheet and your stomach.And if you’ve ever wondered whether you should own more stocks, more bonds, or just more Advil to deal with it all once you retire — this episode’s for you.
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  • The Secret Art of Finding Work You Love and Funding the Life You Want | Chris Hutchins
    Guest: Chris Hutchins, host of All the HacksEpisode theme: Building wealth with meaning—how to design a career (and life) you actually want, while optimizing the money side.What we cover:Meaning > money-first: Chris didn’t start out chasing wealth; he chased options. Early jobs in consulting/banking felt misaligned (little meritocracy, lots of “performance”). That tension pushed him toward work that creates—startups, product, and eventually a podcast.From layoff to leverage: A 2008 layoff forced reinvention. He broke into tech by doing unglamorous, high-initiative work, learning in public, and obsessively networking. Key tactic: create value before you’re hired (he built a full market brief to win a BD role).Career as a cash-flow asset: Once he found work he loved, savings were easier because the job itself provided energy, purpose, and upside. That shift—liking the work—reduced the need to “buy happiness” elsewhere.Optimization without overwhelm: All the Hacks exists to find the 80/20 in money, travel, health, and life. You don’t need to become a points guru or biohacker; borrow Chris’s research and apply the simple levers.Counterintuitive insurance take: When he priced plans, the “best” (premium) plan cost ≈$24k/yr more than the “worst,” while the “worst” plan’s out-of-pocket max was less than that difference. With a real emergency fund and a strong stomach, a high-deductible plan can be rational. (Psychology is the hard part.)Prepay for joy: Pre-buying (subscriptions, passes, prepaid trips) can remove friction and guilt, increasing actual use and happiness.Know your enough: People who don’t know what money is for default to “more.” Define the life you want, price it, then fund that—not a moving target.Audience resonance: “Mini-retirements,” negotiation tactics, and insurance optimization were huge hits; even niche episodes can be life-changing for the right listener.Actionable takeawaysDesign a role you’ll keep doing. Treat your job like part of your portfolio’s fixed-income sleeve: dependable cash flow, lower stress, and compounding skills.Front-load value. Pitch with a one-pager or mini-audit tailored to the company—proof you’ll do the work.Run the insurance math (with your EF). Price premiums vs. out-of-pocket max; let your emergency fund shoulder higher deductibles if the numbers favor it.Prepay strategically. Use prepayment to align behavior with values (fitness classes, transit, annual memberships).Write money rules. E.g., “Invest 20% before lifestyle,” “Use points for intl. biz class only,” “If it saves 10+ hours/yr, buy it.”Lightning-round funBest <$100: Ultrasonic cleaner (for retainers/aligners)—tiny daily upgrade.Most overrated advice: Social-media tax “hacks” that cross legal lines.Apps he likes: A clean net-worth tracker + Copilot for spending (iOS).Guilty pleasure spend: Big annual fees on premium cards—only if the benefits net out.Find Chris: All the Hacks (weekly deep dives). A great starting point: his “Top 50 Lessons” episode.
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  • How I Invest My Own Money in 2025
    Please take a moment to complete this brief survey so I can learn more about YOU and what it is YOU want from this show! I promise, it will take no longer than 97 seconds, and it will help me continue to make the show better for you. There’s a strange YouTube genre called “What’s in My Bag?” where people pull out chapstick like it’s a state secret. This episode is basically that…except the bag is my financial life. And instead of chapstick, it’s index funds and money markets. Not sexy. Not even the flavored kind. Just the plain, unscented stick you find in your coat pocket three years later — still somehow usable.So, what’s in my financial bag? Today I’m walking you through my actual accounts: Roth IRA, taxable brokerage, SEP IRA, and yes, the glorified piggy bank that is my money market fund. I’ll explain what’s in each, why it’s there, and how I think about these buckets so you can use the same framework as a mirror for your own setup.Along the way, I’ll share how I went from aspiring Peter Lynch to preferring mental bandwidth. Why I sometimes hoard cash like a squirrel on Adderall. And why even the smug “just buy the S&P 500 and chill” crowd (myself included) still falls into the trap of trying to outsmart the market — usually by tilting toward “the next big thing” in the most boring way imaginable.Here’s what we cover:Roth IRA: My tax-free sandbox. 100% growth funds. If there’s ever a place to take swings, it’s here.Taxable brokerage: My liquid nest. Efficient, simple, with a healthy pile of cash-like funds as a psychological shock collar reminding me to actually live life.SEP IRA: My tax-bracket tamer. Boring, tax-deferred, locked away for “future Tyler.” (Poor guy.)The irony of tilts: How even with all this simplicity, I still fall into the trap of trying to beat the market with the market.The goal isn’t just to get rich. The goal is to make your portfolio so boring you forget it exists — because you’re too busy living the life it was supposed to buy you in the first place.Hope you all enjoy the show and it offers you something to think about this week!
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  • Trump vs. Obama: Whose 401(k) Made You Richer?
    Before you hit play: I’ve put a quick listener survey together for listeners. It takes less time than finding your password for your old 401(k), and it helps me shape future episodes around what you actually care about.Please take a moment to fill out this 3 minute listener survey here.This week I’m wading into a swamp I usually avoid like lukewarm gas-station sushi: money and politics. Talking about 401(k) policy across administrations feels like trying to explain cricket at Thanksgiving — half the room politely nods, the other half throws turkey legs.But here’s the thing: retirement policy matters, no matter who you love or hate in Washington. Whether you get to retire at 65 or keep working until 87 shouldn’t depend on which political team you root for.In this episode, I walk through how the Obama administration approached retirement savings (think: auto-IRAs, myRA accounts, the Fiduciary Rule) and how Trump’s team countered with their own changes (think: loosening MEPs, alternative assets in 401(k)s, and rolling back fiduciary standards).We’ll break it down into five big ideas you should care about regardless of politics:Access — Millions of Americans still don’t have a workplace retirement plan. Obama pushed for broader access through auto-IRAs, while Trump’s changes were more incremental. Access matters because participation skyrockets when saving is automatic.Simplicity vs. Shiny Objects — Obama tried to make retirement foolproof with boring products like myRA. Trump went the opposite way, pushing for private equity and alternatives inside 401(k)s. Both miss the middle.Fiduciary Rules — Obama’s Fiduciary Rule aimed to make advisors legally put your interests first. Trump’s team scrapped it. What’s left is a murky marketplace where some advisors are fiduciaries and some aren’t — and most Americans can’t tell the difference.Risk & Alternatives — Alternatives like private equity and real estate can add value — if you know what you’re doing. But without education and guardrails, they’re a chainsaw handed to someone who’s only ever used safety scissors.Education — At the end of the day, policies don’t fix behavior. Education does. Whether you’re handed training wheels (myRA) or a Ducati (alternatives), what matters is whether you know how to use them safely.My goal here isn’t to stump for anyone. I’m not campaigning (I don’t even like campaigning for Girl Scout cookies). This is about helping you understand how policy shifts could impact your money and your future.📚 At the end of the episode, I also share a book recommendation that completely changed how I think about investing: Richard Ferri’s All About Asset Allocation. If you’ve ever wanted to understand how to slice up your portfolio without losing your sanity, this is the one.👉 Listen in to learn how retirement policy really affects your wallet — and how to separate political noise from financial signal.
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About Your Money Guide on the Side

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.
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