Taxes in your 50s may not be cocktail party conversation, but they can make or break your retirement plan. In this episode, I kick off a two-part series on the smartest tax moves to make once the kids are (hopefully) off your payroll and you’re staring down retirement.

In Part One, we cover four essential strategies:

• Roth Conversions: Why your 50s and early 60s may be the perfect window to pay taxes on your terms, not Uncle Sam’s.
• Withdrawal Sequencing: The order in which you raid your taxable, pretax, and Roth accounts can extend your portfolio by years.
• Tax-Efficient Investing: How to avoid paying tax on “phantom income” by using ETFs, low-turnover funds, and muni bonds.
• Tax Loss Harvesting: Turning portfolio lemons into lemonade by using losses to offset gains and shrink your tax bill.

Think of this episode as a tax tune-up: no jargon—just practical strategies that can save you tens or even hundreds of thousands over your lifetime.

And this is only Part One. Next week, we’ll cover the HSA triple play, Social Security timing, and two bonus strategies for the charitably inclined and family-minded.

👉 Subscribe so you don’t miss Part Two, and if you’re finding these episodes helpful, consider leaving a quick review. It helps more people discover the show — and keeps me from muttering about Roth IRAs to my dogs in the Vermont woods entirely in vain.

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. 

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.

Guest: Chris Hutchins, host of All the Hacks

Episode 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 takeaways

1. Design 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.
   
   
2. Front-load value. Pitch with a one-pager or mini-audit tailored to the company—proof you’ll do the work.
   
   
3. 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.
   
   
4. Prepay strategically. Use prepayment to align behavior with values (fitness classes, transit, annual memberships).
   
   
5. 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 fun

• Best <$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.

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!

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:

1. 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.
2. 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.
3. 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.
4. 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.
5. 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.

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.

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:

1. 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.
2. 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.
3. 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).

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.

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 With

• How to assess your own social security timing with math — not fear
• What to know about spousal and survivor benefits before you make a move
• How 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 for
• Why risk tolerance isn’t just a form — and how to think about your own appetite for volatility
• A clearer understanding of the real debate between passive and active investing

🧾 Resources Mentioned

• Life Goal Wealth Advisors → www.lifegoalinvestments.com
• Taylor on Instagram → @lifegoalinvestments
• Social Security calculator → www.ssa.gov/benefits/retirement/estimator.html
• CFP Board → www.letsmakeaplan.org

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

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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.