Your Money Guide on the Side

• 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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• What If More Money Still Doesn’t Feel Like Enough?

  What if the biggest financial surprise in your life isn’t running out of money—but realizing that “having enough” doesn’t feel anything like you thought it would?In this episode, I explore the hidden side of wealth: the regrets, letdowns, and quiet disappointments that often surface after you’ve hit your financial goals. From savers who can’t spend, to retirees who waited too long for joy, to high achievers who retired from something but not to something, we unpack why reaching your number doesn’t always equal fulfillment.You’ll hear stories of real people—clients who built millions but treated their brokerage accounts like haunted attics, retirees who postponed joy until it slipped away, and professionals who reached “the dream” only to ask, “now what?” Along the way, we’ll look at surprising research, like why nearly 60% of retirees withdraw less than their required minimum distribution (not from strategy, but from fear), and why the average healthy retirement window is far shorter than most financial plans assume.This isn’t about blowing your 401(k) on a yacht or regretting you didn’t buy Apple stock in the 90s. It’s about the emotional hangover of achieving your goals and realizing you never practiced enjoying the wealth you worked so hard to build.In this episode, we’ll cover:The Curse of the Responsible Saver: why some people can’t spend even when they can afford to.Deferred Joy: the arrival fallacy that keeps people waiting for happiness until it’s too late.Retired From, Not To: how lack of purpose, not lack of money, creates regret.Emergency Spending Accounts: a counter-intuitive way to practice joy with your money now.Redefining “Enough”: why true wealth is measured in stories, not spreadsheets.If you’ve ever wondered what life looks like after hitting your financial goals, or worried that the “someday” you’re saving for may not look the way you hope, this conversation is for you.Because wealth is more than a balance sheet. It’s about spending money—and time—with intention, before it’s too late.👉 If this resonates, subscribe to my free weekly newsletter at tylergardner.com for three takeaways from each episode. And if you enjoy the show, please leave a review on Apple Podcasts or share this episode with a friend—it means the world to me and helps the show grow.

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• How Do I Make My Kid Filthy Rich (Without Going Broke)?

  In case you missed it, check out last week's episode of Your Money Guide on the Side that answers the question How Do I Manage My Own Investments?This Week...Your kid thinks money comes from your phone. Or maybe a magical debit card named Mom. Taxes? Rent? The economics of movie popcorn? Foreign concepts.This episode isn’t about turning your child into a trust fund caricature. It’s about giving them the tools, education, and compounding head start so they have choices—whether that’s taking a sabbatical, starting a business, or saying no to a job that requires a lanyard.We cover three powerful accounts that can build real wealth for your kids:Custodial Brokerage Account – Flexible, market-based investing for minors without requiring earned income. Learn how to fund it, why capital gains can be lower for them, and the pros and cons—including the day they legally take control.Custodial Roth IRA – The most misunderstood (and misused) account in personal finance. If your child has legitimate earned income, this is a way to turn summer job money into lifelong tax-free growth. I’ll walk through the IRS rules, documentation, and why the math borders on magical.529 Plan – A tax-advantaged education savings plan that’s more flexible than you think. We’ll cover state tax deductions, changing beneficiaries, and the new $35,000 rollover option to a Roth IRA.You’ll also hear the traps to avoid (FAFSA penalties, overfunding, and the NFT-buying eighteen-year-old problem), plus how to make sure these tools become teaching moments—not just bank accounts.The goal isn’t to make them rich for the sake of it—it’s to give them freedom, flexibility, and the ability to choose their own path without being shackled to debt or bad jobs.Listen now to learn how to set your kid up for financial independence (and keep them nice about it).

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• How Do I Manage My Own Portfolio? 7 Steps to Start

  In case you missed it, check out last week's episode of Your Money Guide on the Side where we answered the question: When Should I take Social Security?This week on Your Money Guide on the Side, we’re tackling one of the questions I used to get more than any other—right after “Should I buy gold?” and “Is my advisor secretly bad at this?”We’re talking about how to vet your own portfolio. Not how to invest—that’s for another episode. This is about taking the pulse of your current investments and asking: Does this still make sense for my life?You’ll walk away with 7 practical steps to audit your own portfolio, whether you DIY, use an advisor, or have a Frankenstein’s monster of accounts stitched together from every job you’ve ever had. We’ll walk through questions like:Do you understand what you own—or is it the Donkle McFlonkerton Growth Fund?Can you see all your accounts in one place—or are they scattered like mustard packets in your fridge?Are your fees reasonable—or are you quietly tipping a deli worker $18 to assemble your own sandwich?Can you access your money when you actually need it?Is your portfolio accidentally built for a version of you who can stomach rollercoaster markets…but actually can’t?Are you diversified—or just holding Apple stock four different ways under four different fund names?And finally: Is it simple enough to forget about?Because believe it or not, that’s the goal. Not to beat the market, but to build something so clean, boring, and well-designed that it just hums along in the background—freeing up your brain for better things. Like your family. Or your dog. Or binge-watching season three of Is It Cake? without guilt.🎯 This episode is for you if:You’ve got multiple accounts and no idea what’s inside them.You’re unsure what you’re paying in fees—or if those fees are fair.You want clarity, simplicity, and confidence in your investments, without learning Latin.You suspect your portfolio is more complicated than it needs to be.You want a clear, evergreen checklist to revisit any time your finances feel murky.Quick Favor? If this show has been helpful, I’d be grateful if you’d leave a review on Apple Podcasts or share it with someone who might need a financial tune-up. Every episode is built to be evergreen—so whether you’re listening today or in 2035 while AI dogs are walking themselves, my goal is for it to still make sense, still help, and still cut through the noise.Thanks for being here.Let’s run the sanity check.

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• When Should I Take Social Security? | Taylor Sohns

  In case you missed it, check out last week's episode of Your Money Guide on the Side answered the question: How do I Make ChatGPT My New Financial Advisor?How secure is your future benefit and what should you actually do about it?Taylor Sohns is a Certified Financial Planner™ and co-founder of Life Goal Wealth Advisors. Before starting his own firm, Taylor spent over a decade inside some of Wall Street’s biggest investment shops — the ones that build the ETFs, mutual funds, and hedge funds you’ve probably been pitched. Now he works on the other side of the table, helping everyday investors align their portfolios with their real-world goals.📚 What We Discuss with Taylor Sohns:🧮 02:30 — “Coming back to the math” — social security basics 📊 05:20 — The cumulative payout — monthly benefit vs. break-even point ❤️ 08:15 — Spousal benefits — why your timing affects more than just you 📉 11:50 — Social security cuts — what to consider beyond just “take it early” 💼 15:55 — Working after you start social security — common myths 📅 18:00 — Who should wait, who shouldn’t — the role of base rates and earning history 🧠 22:20 — Investment management = behavior management — risk, emotion, and real-life planning 🎯 26:15 — How risk tolerance is actually measured — and how firms get it wrong 📺 29:00 — Reactive news and robust markets — longterm vision ⚖️ 33:30 — Passive vs. active investing — ETFs, experience and exposure. 🔀 37:00 — Is there a middle ground? When active management makes sense💡 What You’ll Walk Away WithHow to assess your own social security timing with math — not fearWhat to know about spousal and survivor benefits before you make a moveHow potential cuts to the system could affect your plan (and what not to panic about)What it really means to “work while claiming” — and who that works forWhy risk tolerance isn’t just a form — and how to think about your own appetite for volatilityA clearer understanding of the real debate between passive and active investing🧾 Resources MentionedLife Goal Wealth Advisors → www.lifegoalinvestments.comTaylor on Instagram → @lifegoalinvestmentsSocial Security calculator → www.ssa.gov/benefits/retirement/estimator.htmlCFP Board → www.letsmakeaplan.orgIf you're still game to support the show, leaving a quick review really helps — even one sentence goes a long way!You can also join thousands of other investing-minded folks by subscribing to the newsletter:https://socialcapconnect.substack.com/Check out episode 26 with Tess Waresmith — a financial educator who shares the costly investing mistakes she made in her 20s, how to vet financial advisors, and why your ignorance is often someone else’s profit.

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