Your Money Guide on the Side
Business & Finance
About
Your go-to podcast for mastering money and investing. Hosted by Tyler Gardner, a trusted influencer with over 4M followers, Your Money Guide on the Side simplifies the complex, adds nuance to what seems simple, and connects you with the brightest minds in finance, investing, and business. Whether you’re just starting or leveling up, this is your one-stop resource to navigate your own finances with clarity, confidence, and a bit of fun. Let’s get you one step closer to where you need to be.
Episodes
- My Interview with Burton Malkiel (That You Will Never Hear)
This episode reconstructs a lost interview with Burton Malkiel, author of A Random Walk Down Wall Street, discussing index investing, market behavior, and the challenges of consistent investment strategies. It covers the origins of index i…
- The 0% Tax Bracket Most Retirees Walk Right Past
This episode of Your Money Guide on the Side discusses how retirees can maximize their after-tax returns by understanding the 0% tax bracket and various tax planning strategies. It covers topics such as Roth conversions, taxable brokerage…
- I Moved to Arizona for the Winter: The 5 Things Nobody Tells You About Snowbirding
Tyler shares lessons learned from spending two months in Sedona, exploring the realities of snowbirding. He discusses how these personal experiences relate to broader decisions about money, lifestyle alignment, and retirement planning.
- 5 Hard Truths About Investing From 26 Years at Motley Fool | Chris Hill
Chris Hill of Motley Fool Money joins Tyler to discuss the realities of long-term investing. They explore the importance of patience, consistency, and avoiding the distraction of hot stocks to achieve investment success.
- The $172,000 Retirement Surprise (And Exactly How to Avoid It)
This episode of Your Money Guide on the Side discusses the overlooked financial risks of long-term care, which affects about 70% of people over 65. It covers the costs, different payment methods like insurance and self-insuring, and why Me…
- Why I'm Taking Social Security at 62 (And Why the "Wait Until 70 Crowd" Might Want to Pay Attention)
In this episode of Your Money Guide on the Side, Tyler explores the factors involved in deciding when to take Social Security. He examines the math and personal considerations behind taking benefits at 62 versus waiting until age 70.
- 5 AI Prompts That Will Change How You Manage Money (And 3 Things It Still Gets Dead Wrong)
This episode explores how to use AI as a tool for financial management, focusing on decision-making, behavioral coaching, and building investment strategies. Tyler also discusses the limitations and potential risks of relying on AI for fin…
- How to Make Your Child Absurdly Wealthy for Absurdly Little
Tyler discusses strategies for parents to build wealth for their children by leveraging the power of compound interest over time. The episode reviews investment vehicles including UGMA/UTMA accounts, custodial Roth IRAs, brokerage accounts…
- How to Stop Buying a Life That Isn't Yours | Hanna Horvath, CFP®
Tyler sits down with CFP Hannah Horvath to discuss the psychological and behavioral factors influencing financial decisions. They explore how values, social pressure, and marketing impact spending habits, and why money should be viewed as…
- The Only Investing Rule You Will Ever Need
In this episode of Your Money Guide on the Side, Tyler explores the Three Bucket Framework, an investing strategy based on timeline rather than age. He explains how to structure portfolios based on when money is needed, rather than followi…
- The $2 Million Plan No Advisor Wants You to See - The Details
In this episode of Your Money Guide on the Side, host Tyler discusses the practical execution of a 90% stocks and 10% money market retirement strategy. He covers how to manage spending adjustments, rebalancing, and cash replenishment durin…
- How to Invest $5 Million (The Only 4 Portfolios You’ll Ever Need)
In this episode, Tyler discusses investment strategies for individuals with substantial assets, arguing that complexity is often unwarranted. He outlines five simple portfolio options, emphasizing fundamentals like time horizon, asset allo…
- The 3 Retirement Numbers You Actually Need
This episode of Your Money Guide on the Side discusses three practical retirement numbers: Traditional FIRE, Coast FIRE, and a minimum option for those nearing retirement. It emphasizes calculating a personal retirement number based on spe…
- 5 Ways to Invest (And Spend) $2 Million
This episode discusses retirement drawdown strategies, explaining why it
- 5 Things the Insurance Industry Doesn't Want You to Know
This episode of Your Money Guide on the Side, hosted by Tyler, offers a critical look at the insurance industry. It clarifies the purpose of insurance as protection against catastrophic loss rather than wealth building, details essential i…
- The 3-Day Workweek Blueprint: How to Buy Back 104 Days a Year | Andy Hill
Andy Hill shares insights on achieving a 3-day workweek by reshaping financial life to work 20-25 hours weekly. The discussion covers tradeoffs, marriage dynamics, and financial security, exploring realistic approaches like "Coast FIRE" an…
- The Rebalancing Lie Every Financial Advisor Tells You
This episode of Your Money Guide on the Side challenges the conventional wisdom around portfolio rebalancing. Host Tyler explains that while rebalancing is important, it is often presented as more urgent and precise than it needs to be, of…
- Why I Buy Stocks at All Time Highs
This episode of Your Money Guide on the Side discusses the pitfalls of waiting for the perfect moment to invest. Host Tyler explains why buying stocks at all-time highs is often a superior strategy to sitting in cash, highlighting that all…
- How to Save $50,000 in Taxes by Moving Your Investments to the Right Accounts
This episode discusses account placement strategy, focusing on how the location of investments significantly impacts long-term tax savings. It covers the different types of investment accounts (tax-deferred, tax-free, taxable) and provides…
- Why Men Are Terrible Investors (And Lose 1% More Than Women Every Year)
This episode of Your Money Guide on the Side delves into five lesser-known behavioral biases that negatively impact investment decisions: the Disposition Effect, Ostrich Effect, Mental Accounting, Gambler's Fallacy, and Action Bias. It exp…
- Your Brain Is Stealing $245,000 From Your Retirement (Here's How to Stop It)
This episode of Your Money Guide on the Side discusses five psychological biases that negatively impact retirement savings. It explains how overconfidence, recency bias, loss aversion, and hindsight bias can lead to poor investment decisio…
- 5 Things I Won't Do With My Money in 2026
In this episode, Tyler discusses five financial decisions he will not make in 2026, challenging common advice on mortgages, savings accounts, and investing. He emphasizes simplicity and intentionality over constant financial activity.
- The $2 Million Portfolio Plan No Advisor Wants You to See
This episode details a 90% stocks/10% money market fund investment plan for substantial portfolios, advocating for confident withdrawals of $120k-$200k annually to support lifestyle and experiences while managing market volatility with a c…
- The Best (And Worst) States to Retire To - Part 2 of 2
This episode, part two of a series, analyzes US states for retirement, focusing on effective tax rates beyond just state income tax. It highlights states like Iowa, Pennsylvania, and New Jersey as potential financial gems, while cautioning…
- The Best (And Worst) States to Retire To - Part 1 of 2
This episode of Your Money Guide on the Side, Part 1 of 2, debunks common retirement location myths by examining effective tax rates rather than just state income taxes. It highlights how certain high-tax states might be more beneficial fo…
- The Real Financial Order of Operations - Part 2 of 2
This episode, part two of a series, covers the "gray areas" of financial planning. It challenges the conventional advice of keeping six months of expenses in cash, explains the benefits of taxable brokerage accounts after maximizing retire…
- The Real Financial Order of Operations - Part 1 of 2
This episode rebuilds the financial order of operations, prioritizing self-care, then systematically tackling credit card debt, securing insurance, and maximizing retirement accounts like Roth IRA, 401(k), and HSA. The episode aims to prov…
- The DIY Investor's Guide to Building Your Own Index Fund (And Why It's a Terrible Idea)
This episode discusses the concept of building your own index fund, detailing market sectors, benchmark functionality, and the temptation of 'tilts'. It explains how to replicate the market using sector ETFs while highlighting the efficien…
- 4 Tax Moves That Can Save You 6 Figures - Part 2 of 2
This episode covers four advanced tax strategies for individuals in their 50s: leveraging HSAs as a retirement tool, understanding the tax implications of Social Security claiming age, utilizing donor-advised funds for charitable giving an…
- 4 Tax Moves That Can Save You 6 Figures - Part 1 of 2
This episode covers four key tax strategies to potentially save significant money on retirement: Roth Conversions, Withdrawal Sequencing, Tax-Efficient Investing, and Tax Loss Harvesting. These practical tips are designed to help individua…
- 10 Ways Investors Lose Money Without Knowing It
This episode of Your Money Guide on the Side details ten common ways investors unknowingly lose money, such as hidden fees, overtrading, taxes, and emotional investing. It provides actionable advice and a checklist to help investors identi…
- The Only Asset Allocation Guide You’ll Ever Need
This episode explains asset allocation, focusing on compounding and diversification over individual stock performance. It details three allocation models suitable for various risk tolerances and discusses retirement strategies like the 're…
- The Secret Art of Finding Work You Love and Funding the Life You Want | Chris Hutchins
Chris Hutchins shares insights on designing a fulfilling career and life, emphasizing meaning over money. He details his journey from a layoff to success in tech, advocating for treating jobs as cash-flow assets and optimizing finances thr…
- How I Invest My Own Money in 2025
In this episode, the host breaks down their personal investment strategy, detailing the contents of their Roth IRA, taxable brokerage, and SEP IRA accounts. They explain the rationale behind each account's holdings and how they approach th…
- Trump vs. Obama: Whose 401(k) Made You Richer?
This episode compares retirement savings policies under the Obama and Trump administrations, focusing on five key areas: access to plans, simplicity versus complex investments, fiduciary rules for advisors, the role of alternative assets,…
- What If More Money Still Doesn’t Feel Like Enough?
This episode of Your Money Guide on the Side discusses the emotional challenges that arise after achieving financial goals, such as the inability to spend saved money or postponing joy. It explores why reaching financial targets doesn't al…
- How Do I Make My Kid Filthy Rich (Without Going Broke)?
This episode of Your Money Guide on the Side discusses how to set children up for financial independence by explaining three wealth-building accounts: Custodial Brokerage Accounts, Custodial Roth IRAs, and 529 Plans. It covers funding, tax…
- How Do I Manage My Own Portfolio? 7 Steps to Start
This episode of Your Money Guide on the Side provides 7 steps to audit your investment portfolio. It covers understanding holdings, fees, accessibility, diversification, and simplifying your accounts for better financial clarity and confid…
- When Should I Take Social Security? | Taylor Sohns
This episode features Taylor Sohns, a Certified Financial Planner™, discussing Social Security basics, spousal benefits, and the impact of potential system cuts. It also covers myths about working after claiming benefits and assessing risk…
- How do I Make ChatGPT My New (Free) Financial Advisor?
This episode of Your Money Guide on the Side explores using ChatGPT as a financial thought partner. Host Tyler Gardner discusses five ways AI can help listeners clarify values, understand risk tolerance, map financial timelines, analyze ad…
- 3 Silent Wealth Killers Hiding in Fine Print | Tess Waresmith
Financial educator Tess Waresmith discusses silent wealth killers like hidden fees and provides insights on asset allocation and financial literacy. The episode aims to empower listeners to make informed investment decisions and avoid cost…
- The ONLY 6 Accounts You Will Ever Need
In this episode of Your Money Guide on the Side, Tyler outlines the six crucial financial accounts needed for wealth building, downside protection, and long-term flexibility. He explains how to use checking accounts, HYSAs, Roth IRAs, pre-…
- How to Die With Zero | Bill Perkins
Bill Perkins, author of Die With Zero, joins Your Money Guide on the Side to discuss his philosophy that experiences are the true end goal, not just accumulation of wealth. The episode explores prioritizing spending now, the concept of mem…
- 3 Reasons You’ll Never Beat the Stock Market
This episode of Your Money Guide on the Side features Tyler Gardner discussing the futility of trying to beat the stock market. Gardner explains why benchmarks like the S&P 500 are often irrelevant and how behavioral biases can negatively…
- The Secret Strategies of Billion-Dollar Portfolios | Wendy Li
Wendy Li discusses how institutional investors manage billions, comparing their strategies to individual investors. The episode covers risk management, understanding returns, long-term investing, and choosing fund managers.
- How Much Can I Spend in Retirement?
This episode of Your Money Guide on the Side re-examines the 4% retirement rule, exploring its origins and limitations. It discusses the Trinity Study, sequence of returns risk, and the importance of portfolio size and asset allocation, of…
- The Simple Path to F-You Money | JL Collins
JL Collins, author of The Simple Path to Wealth, joins Your Money Guide on the Side to discuss the true meaning of financial independence: reclaiming control and the ability to say no. The episode revisits his life philosophy, shaped by ea…
- 10 Rules of Buying a New Car Without Getting Screwed
This episode of Your Money Guide on the Side outlines 10 rules for purchasing or leasing a new car to avoid financial pitfalls. It covers strategies like when to approach a dealership, using financing effectively, and understanding depreci…
- What Men Need to Hear About Money | Mady Mills
Mady Mills joins Your Money Guide on the Side to discuss navigating personal finance, market volatility, and relationship money advice. The episode covers surviving the newsroom, making financial content accessible, and the most important…
- 3 Ways to Invest $1,000,000
This episode of Your Money Guide on the Side features three investors—Chad, Nina, and Marge—showcasing distinct strategies for investing $1 million. It explores how individual risk tolerance, time horizon, and financial goals influence por…