Your Money Guide on the Side

Ever thought about building your own index fund? It could be an enlightening experience, but it’s not without its challenges! Discover the 11 market sectors and how they impact your portfolio. Learn how benchmarks like the S&P 500 operate and their hidden efficiencies. Explore the concept of investment 'tilts' and when they might be worth considering. And while DIY funds might sound appealing, the expert insights reveal that index funds are often the smarter, hassle-free choice. Education is key, but simplicity trumps complexity!

In this insightful discussion, discover why HSAs are a hidden gem for retirement savings with triple tax benefits. Learn how the timing of claiming Social Security can dramatically impact what you owe the IRS. Explore the flexibility of donor-advised funds for generous giving, and how charitable strategies can lower your tax bracket. Uncover gifting techniques that help move wealth to the younger generation while minimizing taxes. This comprehensive toolkit empowers you to keep more of your hard-earned money as you navigate your 50s.

Explore smart tax strategies to boost your retirement in your 50s! Discover why now is the ideal time for Roth conversions. Learn the optimal order to withdraw from your accounts to maximize your funds. Find out how to avoid taxes on phantom income using ETFs and municipal bonds. Plus, turn investment losses into tax savings with smart harvesting techniques. Get ready for practical tips that could save you six figures over your lifetime!

Discover the hidden leaks draining your investment portfolio! Learn how tiny fees add up to massive losses over time, and why overtrading can turn your returns into Swiss cheese. Uncover the unnecessary costs of load fees and how to avoid them. Understand the impact of taxes, cash drag, and emotional trading decisions that can sabotage your wealth. Plus, walk away with actionable strategies to keep more money in your account and make your investment journey smoother.

Discover the art of asset allocation and why it's more crucial than finding the hottest stocks. Learn how compounding works and why average returns can be misleading. Explore the benefits of diversification with non-correlated assets to stabilize your portfolio. Dive into three practical allocation strategies tailored to different risk tolerances. Plus, uncover the surprising advantages of the reverse glide path for retirement planning. Whether you're cautious or adventurous, find a strategy that aligns with your financial goals and peace of mind.

Chris Hutchins, host of the All the Hacks podcast and a leader in product strategy, shares his journey from corporate dissatisfaction to meaningful work in startups. He discusses how a layoff prompted him to leverage his unique skills and create value before getting hired. Chris emphasizes that finding work you love can transform saving habits, making money less central to happiness. He also challenges conventional views on insurance plans, advocating for high-deductible options when paired with an emergency fund. Discover his insights on prepaying for joy and aligning wealth with purpose!

Discover the intriguing details of one investor's financial strategy. He shares his Roth IRA approach, focusing on 100% growth funds for tax-free gains. Explore his taxable brokerage, which includes liquid assets and a money market fund serving as both liquidity and a spending nudge. Delve into the SEP IRA for tax benefits and the caution against over-complicating investments with too many tilts. Ultimately, he emphasizes that money should enhance life and highlights the importance of mental bandwidth in financial decisions.

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.

Exploring the emotional side of wealth, the discussion reveals that reaching financial goals often brings unexpected feelings of emptiness. It highlights the 'Curse of the Responsible Saver,' where frugality traps individuals from enjoying their wealth. The concept of 'Deferred Joy' surfaces, illustrating the dangers of postponing happiness. Listeners hear real-life stories of retirees and high achievers grappling with identity loss. The conversation emphasizes that relationships and a sense of purpose are more crucial to fulfillment than merely financial success.

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).