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.

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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!

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.

And in case you missed it, check out last week's episode of Your Money Guide on the Side where we answered the question How Much Does a Financial Advisor Actually Cost?

What if your smartest financial sidekick never sleeps, never judges, and doesn’t charge 1% AUM?

In this episode of Your Money Guide on the Side, Tyler Gardner explores how to use ChatGPT—not as your stock-picking guru, but as your emotionally-stable, algorithmic thought partner. One that can help you think better about money, values, timelines, and fees—without selling you a whole life policy disguised as “peace of mind.”

We break it down into five key ways AI can help you think more clearly, not just calculate faster:

🧭 Clarify Your Values
Ask ChatGPT: “What do I actually want money to do for me?” Spoiler: “Retire early and drink wine in Italy” is not a core value—it’s a Pinterest board. Let AI help you write a personal money mission statement and filter out everyone else’s goals.

🧠 Understand Your Risk Profile
Forget the nonsense quizzes (“If the market drops 20%, do you: A) Buy more, B) Cry in the tub...”). ChatGPT can simulate scenarios, unpack your financial behavior, and help you discover if you’re actually more golden retriever than honey badger when volatility hits.

📆 Map Your Timeline
Your life isn’t one big finish line. It’s a winding trail with sabbaticals, pivots, slow travel years, and expensive hobbies you haven’t picked yet. Use AI to draft your financial timeline and test your plan against reality—before your knees give out.

💸 Analyze Your Fees
The 1% “small” fee isn’t small when you compound it for 30 years. ChatGPT can help you unpack your advisor agreement or prospectus, run cost projections, and tell you whether you’re paying for advice—or just someone else’s lake house.

📊 Review Your Portfolio
Paste in your holdings and let AI review your diversification, concentration, expense ratios, and risk alignment. You may find out your “balanced” portfolio is just three tech stocks in a trench coat.

🔍 Bonus: Ask it to roleplay your 65-year-old self reviewing your current plan. You might learn what your future self wishes you’d done while you still have time to do it.

Bottom Line:
This isn’t about replacing all humans with robots. It’s about using sharper tools to ask better questions:

– What do I value?
 – What’s my actual risk tolerance?
 – When do I want money to matter?
 – What am I really paying?
 – Is my current strategy aligned with who I want to become?

If AI can help you do that without judgment, jargon, or sales tactics—why not use it?

So go ahead. Paste your plan. Ask the “dumb” question. And remember: the smartest people in the room aren’t the ones with all the answers—they’re the ones still curious enough to keep asking.

If this episode made you laugh, think, or recheck your advisor’s fee schedule—leave a review on Apple Podcasts or send it to a friend still paying 1.75% and calling it “normal.”

And in case you missed it, check out last week's episode of Your Money Guide on the Side where we answered the question, What Accounts do I Actually Need?

Tess Waresmith is a financial educator, speaker, and investor known for helping people reach financial independence with simple investing. She’s the founder of Wealth With Tess, where she helps women build wealth and confidence through investing. Tess has been featured by CNBC, Business Insider, and Fox 5 NY, and is a self-made millionaire focused on helping others avoid the mistakes that cost her… well let’s not go there.

📚 What We Discuss with Tess Waresmith:

🔍 03:15 — Early mistakes and financial wake-up calls — who should handle your money?
 💸 06:40 — Millions lost in fees — how hidden costs quietly eat your future
 📈 08:15 — “It’s not that hard” — building confidence by learning the basics
 🧠 10:00 — Asset allocation 101 — understanding fiduciary duty and financial jargon
 🧾 13:00 — Learned money scripts and access to real financial literacy
 ⚖️ 15:00 — Avoiding absolutes — why personal finance isn’t one-size-fits-all
 ⏳ 17:20 — The time investment of investing — and why it’s worth it
 🚫 20:00 — Breaking up with your advisor — navigating the money manager minefield
 🚩 25:55 — Red flags in your fees — questions to ask and answers to expect
 🤫 29:00 — Your ignorance is someone’s profit — staying sharp in a noisy market
 🎓 30:30 — $50K of financial education in 4 minutes — a crash course curriculum
 ⚡ 35:30 — Lightning round! — quickfire investing truths and final thoughts

💡 What You’ll Walk Away With

• How to spot hidden fees that quietly drain your portfolio
• The confidence to make financial decisions without outsourcing everything
• What to ask before trusting someone with your money
• A basic framework for asset allocation and fiduciary responsibility
• Why there's no single “right” way to invest
• Tools for becoming an informed investor, even if you’re starting from scratch

🧾 Resources

• Tess’s website: www.wealthwithtess.com
• Financial independence mini-course: www.wealthwithtess.com/fi
• Follow Tess on Instagram: @wealthwithtess
• Featured on:
  • CNBC
  • Business Insider
  • Fox 5 NY

If 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: one practical idea, once a week, zero fluff — www.tylergardner.com/newsletters.

Check out episode 23 with Bill Perkins — a hedge fund manager and author of Die With Zero, who explains why the best return on investment might be spending your money now on experiences that 

And in case you missed it, check out last week's episode of Your Money Guide on the Side where Bill Perkins and I answered the question, How Do I Die With Zero? 

In this solo episode, Tyler breaks down the only six financial accounts you’ll ever truly need—and more importantly, how to actually use them. Whether you’re just getting started or managing a more complex portfolio, this is your streamlined, nonsense-free guide to designing a system that works.

No more chasing every new fintech app or wondering if you’re missing something. If you’ve ever felt overwhelmed by the alphabet soup of financial tools, Tyler’s here to cut through the noise and give you a clear path forward. These six accounts are enough to build wealth, protect your downside, and create long-term flexibility. And anything beyond them? Likely just extra complexity disguised as “optimization.”

What You’ll Learn:

• Why a regular checking account should be boring—and how to keep it that way
• How to think about a High-Yield Savings Account (HYSA): the “glovebox” for your cash—not your investment engine
• The power of a Roth IRA—and how it’s often misunderstood
• Why a pre-tax IRA or 401(k) still matters, even if retirement feels far away
• The secret weapon of the wealthy: the HSA (Health Savings Account) and how to use it for more than doctor’s visits
• How a taxable brokerage account unlocks true flexibility—and why you might want to use it before maxing everything else

Plus:

• A better metaphor than “bucket strategy”
• Why most emergencies aren’t emergencies at all (and what that means for where your cash lives)
• The order Tyler recommends for prioritizing contributions
• When not to use these accounts (because yes, even the Roth IRA can be misused)

Whether you're 25 and just opening your first Roth, or 55 and wondering how to consolidate accounts, this episode gives you a timeless roadmap to simplify your finances without oversimplifying your life. As always, Tyler brings the clarity, the nuance, and just enough humor to make talking about tax-advantaged accounts… well, weirdly fun.

And in case you missed it, check out last week's episode of Your Money Guide on the Side where we answered the question, How do I beat the stock market? 

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

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

You can also join thousands of other investing-minded folks by subscribing to the newsletter: www.tylergardner.com

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.

And in case you missed it, check out last week's episode of Your Money Guide on the Side where we answered the question, What do Billion Dollar Portfolios Look Like?

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.

 📬 Subscribe to the newsletter for 3 financial insights every Sunday
 📲 Follow Tyler on IG/TikTok: @socialcapofficial
 📈 Want to support the show? A quick review or share goes a long way.

And in case you missed it, check out last week's episode of Your Money Guide on the Side where we answer the question, How Much Can I Spend in Retirement? 

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.