Your Money Guide on the Side

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).

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 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.

Explore how ChatGPT can be your free financial ally, enhancing your money decisions. Discover how to clarify your values and create a personal mission statement. Learn to understand your risk profile without the usual nonsense quizzes. Chart a financial timeline that accommodates your unique life path, including sabbaticals and hobbies. Finally, uncover the true cost of fees and how to navigate your advisor agreements. With AI, make smarter financial choices without the pressure of traditional advising.

In this lively discussion, financial educator Tess Waresmith, founder of Wealth With Tess, focuses on empowering women through investing. She shares her own financial missteps and highlights how hidden fees can silently siphon off wealth. Tess emphasizes the necessity of financial literacy, urging listeners to question conventional advice. Her frank take on the investment landscape encourages confidence and self-advocacy, while providing quick tips to spot red flags in financial services. Tune in for a crash course so you can take charge of your financial future!

Discover the six essential financial accounts that can simplify your wealth management. Learn why a boring checking account is key, how to use a High-Yield Savings Account as your cash glovebox, and the often-overlooked power of Roth IRAs. Uncover the secret of HSAs beyond just healthcare, and see how a taxable brokerage account offers true flexibility. Gain insights on prioritizing contributions and navigate financial emergencies with clarity, all while avoiding unnecessary complexity in your financial tools.

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 WithWhy deferring joy is often just fear in disguiseA new way to think about saving, giving, and legacyHow to measure value through memory, not moneyA framework for spending intentionally at different life stagesHow to plan for the end of life without missing the middle🧾 Resources MentionedDie With Zero by Bill Perkins → https://a.co/d/9KKHOzTYour Money or Your Life by Vicki Robin and Joe Dominguez → https://yourmoneyoryourlife.comIf 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.comIf 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 youWhy the S&P 500 isn’t a fair benchmark for most peopleMarket 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 moreHow even the pros struggle — and why surviving your own brain is the real edgeWhen paying a 1% advisor fee might actually be a bargainWhy boring, automated, diversified investing is the best strategy no one wants to hear aboutWhether 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 withHow institutions manage risk — and how to apply it to your own investingWhy most retail investors misunderstand returnsHow to think long-term when markets are volatileWhat to ask before trusting a fund manager with your moneyHow to approach alternatives without insider accessThe core skills every smart investor needsIf 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.

And in case you missed it, check out last week's episode of Your Money Guide on the Side with JL Collins where we answer the question, How do I get F-You Money? 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 ignoreHow sequence of returns risk can silently wreck your planWhy portfolio size and asset allocation matter far more than a static percentageSmarter, more dynamic strategies to adjust year-by-yearIf 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.