As always, a MASSIVE thank you to this week's sponsors! Momentous: ? ?livemomentous.com Use code Tyler for 35% off your first order! Thrive Market: ? ?thrivemarket.com/tyler $20 off your first three orders plus you?ll get a FREE $60 gift! Facet: ? ?facet.com/tyler for an exclusive $550 kickstart offer! Anthropic: ? ?claude.ai/tyler if you're looking for the best business and thought partner I have EVER had. And on to the show notes! Most financial advice focuses on optimization. This episode is about something else entirely: alignment. In this more personal episode, Tyler shares five lessons from spending two months ?snowbirding? in Sedona ? and what the experience revealed about money, time, and the life we think we want. Because sometimes the biggest financial insights don?t come from spreadsheets. They come from living differently long enough to notice what actually matters. In this episode, Tyler reflects on: Why buying back time only works if you know what to do with it The idea of a ?path dividend? ? testing lifestyles before committing to them How lifestyle upgrades quickly become your new normal (and lose their impact) Why major life changes require understanding what you?re leaving, not just gaining The illusion that a new place will create a new version of you Along the way, Tyler connects everyday moments ? cooking dinner, staying in Airbnbs, almost buying a house ? to deeper financial decisions around spending, relocation, and retirement. The core idea: Wherever you go, there you are. Money can change your environment. It doesn?t automatically change you. This episode isn?t about maximizing efficiency. It?s about building a life that actually fits ? before you build the plan to fund it. If the show?s been helpful, leaving a quick review on Apple or Spotify genuinely helps. Hope this gives you something to think about this week.

Pre-Order Tyler's First Book, Real Wealth, ??here?? & be immediately eligible for exclusive bonuses between now and December 1st! April Bonus: Free two-hour digital live event on Wednesday, May 6th from 7-9pm EDT, where Tyler will answer the most commonly asked questions and walk through what you can expect from the book! And as always, a MASSIVE thank you to this week's sponsors: LMNT just dropped a limited-time Pink Lemonade flavor ? exclusively for LMNT INSIDERs, which means you need to order the INSIDER Bundle (four boxes for the price of three) to get it. If you like your electrolytes without the sugar and your hydration without the regret, this one's for you: ? drinklmnt.com/tyler Fabric: ten minutes online, no health exam, no phone calls, a million dollars in coverage for less than a dollar a day ? and if you're young and healthy, there's no better window to lock this in than right now. ? meetfabric.com/tyler Copilot Money tracks your spending, net worth, investments, subscriptions, and savings goals in one place ? and it's the only personal finance app to win an Apple Editor's Choice Award, with a 4.8-star rating from over 25,000 reviews. ? try.copilot.money/tyler ? use code TYLER2 for two free months. And on to the show notes! Most people think investing is about finding the next big thing. The reality is much less exciting ? and far more effective. In this episode, Tyler sits down with Chris Hill, longtime host of Motley Fool Money, to talk about what actually drives long-term success in investing ? and why so many people get distracted along the way. From launching a podcast during the 2008 financial crisis to interviewing some of the biggest names in business and finance, Chris shares lessons from decades inside one of the most influential investing platforms. In this conversation, Tyler and Chris discuss: How Motley Fool Money started during a crisis ? and why simplicity won Why investors obsess over ?hot stocks? and excitement (and why that hurts returns) The importance of time in the market ? and not interrupting compounding Why the best companies are often the ones everyone already knows The balance between simple index investing vs. active stock picking Chris also reflects on what makes a great investor over time ? and it?s not intelligence or access. It?s patience. Discipline. And the ability to ignore noise when it matters most. The core idea: Investing isn?t about being clever. It?s about staying consistent long enough for compounding to do its job. If the show?s been helpful, leaving a quick review on Apple or Spotify genuinely helps. Hope this gives you something to think about this week.

Pre-Order Tyler's First Book, Real Wealth, ?here? & be immediately eligible for exclusive bonuses between now and December 1st! April Bonus: Free two-hour digital live event on Wednesday, May 6th from 7-9pm EST, where Tyler will answer the most commonly asked questions and walk through what you can expect from the book! And as always, a MASSIVE thank you to this week's sponsors: Thrive Market: Get $20 off your first three orders plus a FREE $60 gift if you order at thrivemarket.com/tyler today. Facet: find out why I have been endorsing Facet for over 18 months now by checking out ?facet.com/tyler?. They are a one-stop shop for financial planning, investment management, tax strategy, and retirement planning. And best part: it's all for one flat annual membership fee. And on to the show notes! No one wants to think about long-term care. Which is exactly why most people don?t plan for it. In this episode, Tyler tackles one of the most uncomfortable ? and most overlooked ? parts of financial planning: what happens if you live long enough to need care. Because longevity is a gift. And financially, it?s also a risk. In this episode, Tyler covers: The reality that ~70% of people over 65 will need some form of long-term care What long-term care actually means (it?s not just nursing homes) The real costs ? from home care to assisted living to memory care Why long-term care is separate from normal retirement planning The four ways to pay for it: self-insuring, Medicaid, traditional insurance, and hybrid policies Why Medicare doesn?t cover what most people think it does How to estimate your true long-term care exposure (and why it can reach seven figures) The biggest mistakes people make ? including relying on kids or ?figuring it out later? Tyler also lays out a clear, practical framework: Understand your numbers. Decide who pays. And make the decision before you need it. The core idea: A retirement plan isn?t complete until it answers one question ? what happens if care is required? Because this isn?t just a financial decision. It?s a decision that affects your spouse, your kids, and how the last chapter of your life actually plays out. If the show?s been helpful, leaving a quick review on Apple or Spotify genuinely helps. Hope this gives you something to think about this week.

Pre-Order Tyler's First Book, Real Wealth, here & be immediately eligible for exclusive bonuses between now and December 1st! As always, a MASSIVE thank you to this week's sponsors: LMNT?: regardless of who much money you have, if you're not feeling your best physically and mentally, it means very little. That's why I drink ?LMNT? daily (well, multiple times a day) to continue to be as productive as I can be after my workouts. Try ?drinklmnt.com/tyler? today and let me know what your favorite flavor is! Copilot Money?: if you are looking for one of the most well-designed money apps out there, check out ?Copilot Money? today. My friends and family continue to rave about it, and they now have all of their money needs in one place. Check out ?try.copilot.money/tyler ?today and use code TYLER2 for two free months, so you can see if it works for you! Anthropic?: I use Claude AI every single day as a thought partner and business strategist. To become more efficient and solve problems more quickly and effectively, check out ?claude.ai/tyler? today. There is no single business move I have made in the past year that has been more worthwhile and productive. And on to the show notes! When should you take Social Security? It?s one of the most debated ? and most personal ? financial decisions you?ll ever make. In this episode, Tyler makes a serious, data-backed case for taking benefits at 62 ? not as a blanket recommendation, but as a counterpoint to the conventional advice to always wait. Because this decision isn?t just math. It?s math layered on top of real life. In this episode, Tyler covers: The break-even math between taking benefits at 62, 67, and 70 Why waiting only ?wins? if you live past your late 70s or early 80s The idea that a dollar at 62 isn?t equal to a dollar at 82 How the ?go-go, slow-go, no-go? phases of retirement change how money is experienced The often-overlooked healthcare gap between 62 and 65 ? and what it can cost How the earnings test reduces (but doesn?t eliminate) benefits if you keep working Why Social Security decisions should factor in your spouse?s survivor benefit Tyler also introduces a practical framework ? six key questions ? to help you make the decision based on your own life, not a generic rule: Health. Healthcare. Work status. Income needs. Spousal impact. And how you actually want to spend your time. The core idea: This isn?t about maximizing dollars. It?s about maximizing life. For some people, waiting is the right call. For others, taking it early ? and using that money when it matters most ? may be the better decision. If the show?s been helpful, leaving a quick review on Apple or Spotify genuinely helps. Hope this gives you something to think about this week.

As always, a MASSIVE thank you to this week's sponsors: Gelt: I will forever regret not prioritizing a tax strategist early in my solopreneur journey. Don't make the same mistake I did and leave money on the table. If you are a business owner or a high net worth individual, check out Gelt today at joingelt.com/tyler. Fabric: there is a reason that term life insurance is number 4 in my financial order of operations, before an Emergency Fund, and before funding the Roth IRA. If anyone else depends on your income, cross this off your list today in ten minutes at meetfabric.com/tyler. And on to the show notes! AI isn?t replacing financial advisors. But it is getting surprisingly good at doing one of the most valuable parts of the job: stopping you from making bad decisions. In this episode, Tyler breaks down how to actually use AI as a financial tool ? not for stock picks or shortcuts, but for clarity, structure, and behavioral coaching. Because the biggest gap in investing isn?t information. It?s execution. In this episode, Tyler covers: Why most investors underperform the market ? and how behavior drives that gap How to build a complete financial snapshot for better decision-making How to use AI to uncover your real risk tolerance (not the one you think you have) How to create a simple, diversified investment strategy using structured prompts Why asset location (where you hold investments) matters more than most people realize How to stress test your plan using worst-case scenarios and Monte Carlo thinking How to use AI as a behavioral guardrail during market volatility The real risks: privacy concerns, bad prompts, and AI hallucinations The core idea: AI is a tool, not a replacement for judgment. Used well, it can help you think more clearly, avoid emotional decisions, and build a plan you actually understand. Used poorly, it can give you confident-sounding answers to the wrong questions. If you take one thing from this episode, it?s this: Better inputs lead to better decisions. And if AI helps you slow down, ask better questions, and avoid one major mistake, it?s already paid for itself. If the show?s been helpful, leaving a quick review on Apple or Spotify genuinely helps. Hope this gives you something to think about this week.

As always, a MASSIVE thank you to this week's sponsors: LMNT: regardless of who much money you have, if you're not feeling your best physically and mentally, it means very little. That's why I drink LMNT daily (well, multiple times a day) to continue to be as productive as I can be after my workouts. Try drinklmnt.com/tyler today and let me know what your favorite flavor is! Copilot Money: if you are looking for one of the most well-designed money apps out there, check out Copilot Money today. My friends and family continue to rave about it, and they now have all of their money needs in one place. Check out try.copilot.money/tyler today and use code TYLER2 for two free months, so you can see if it works for you! Facet: find out why I have been endorsing Facet for over 18 months now by checking out facet.com/tyler. They are a one-stop shop for financial planning, investment management, tax strategy, and retirement planning. And best part: it's all for one flat annual membership fee. Check out facet.com/tyler and see if they're the right fit for you! And on to the show notes! Many parents want to help their kids financially ? but often focus on the wrong things. Saving for a wedding, helping with a down payment, or paying for grad school can help in the moment. But the biggest advantage you can give a child financially is time. In this episode, Tyler breaks down how investing small amounts early in a child?s life can turn into millions thanks to compound growth ? and walks through the most practical ways parents can do it. In this episode, Tyler covers: How investing $3,000 per year for a decade could grow into millions over a lifetime The power of giving a child 20?30 extra years of compounding How UGMA/UTMA accounts work and their tax implications Why a custodial Roth IRA can create completely tax-free retirement wealth A lesser-known strategy: investing in your own brokerage account and passing assets down with a step-up in basis Why 529 plans are useful ? but often overhyped and less flexible The key takeaway: when it comes to investing for your kids, starting early matters far more than the amount you invest. Even small, consistent contributions can grow into life-changing sums over decades. If this episode helped clarify your approach to investing for your family, consider leaving a quick review on Apple Podcasts or Spotify ? it helps others find the show.

As always, a massive thanks to this week's sponsors: Anthropic: I use Claude AI every single day as a thought partner and business strategist. To become more efficient and solve problems more quickly and effectively, check out claude.ai/tyler today. Bilt: If you're not earning rewards from your biggest annual expense (rent and mortgage!), you might just be missing out. Learn more about their three new credit cards and how you can start earning rewards for your biggest expenses at joinbilt.com/tyler. Gelt: And I'll go to my grave with this one: the single biggest mistake I have made in business thus far is not prioritizing finding a tax strategist and partner before anything else. Go to joingelt.com/tyler to see if they can help your business find what it's been missing. And on to the show notes! Most financial advice assumes money decisions are rational. Spend less. Save more. Invest consistently. But in reality, our financial decisions are often driven by psychology, identity, and social pressure far more than spreadsheets. In this episode, Tyler sits down with Hannah Horvath, CFP and writer of Your Brain on Money, to explore why traditional financial advice misses the behavioral side of money ? and why understanding your values matters just as much as understanding the math. In this conversation, Tyler and Hannah discuss: Why information alone rarely changes financial behavior How social comparison shapes spending and lifestyle choices Why defining ?enough? is more psychological than financial How marketing profits from creating a sense of lack The hidden cost of hyper-convenience and digital isolation Why community and real-world connection matter more than we think The core idea: money is a tool, but if you don?t define what you actually value, it?s easy to spend your life chasing someone else?s version of success. If you?d like to explore more of Hannah?s work, you can find her newsletter Your Brain on Money, where she writes about the psychology and culture behind our financial decisions. And if the show?s been helpful, leaving a quick review on Apple or Spotify genuinely helps. Hope this gives you something to think about this week.

As always, a MASSIVE thank you to this week's partners: Fabric: if anybody relies on your income, you need to consider term life insurance asap. Check out meetfabric.com/tyler to find out the right coverage for you and your loved ones. Facet: and even though I WANT to offer you all direct advice, I can't, as I don't know you. But Facet can, and they continue to practice exactly what I preach. Check out joinfacet.com/tyler today. And on to the show notes! ?How should a 60-year-old invest?? It sounds like a reasonable question. It?s also the wrong one. In this episode, Tyler dismantles the idea that your age should determine your portfolio ? and replaces it with a framework that actually works: invest based on when you need the money, not how many birthdays you?ve had. Because two people the same age can ? and often should ? invest completely differently. Instead of age-based formulas like ?110 minus your age,? Tyler introduces a simpler system: The Three Bucket Framework Bucket 1 (0?2 years): Cash, money markets, short-term treasuries. Zero stock exposure. Bucket 2 (2?10 years): A glide path. Years until goal = % in stocks. Bucket 3 (10+ years): 100% stocks in low-cost index funds. That?s it. This episode walks through real examples ? retirees, early retirees, 30-year-olds saving for houses, 70-year-olds investing for grandkids ? to show why timeline beats age every time. Tyler also explains: Why sequence-of-returns risk matters more than age How to structure withdrawals using the bucket system Why most ?conservative by default? advice is lazy The 10 investing terms you actually need to understand How to match allocation to goals without overcomplicating it The core idea is simple: Your timeline is your allocation. Stop asking how a 60-year-old should invest. Start asking when the money will be spent. If this framework changes how you think about your portfolio, leaving a quick review on Apple or Spotify genuinely helps. Hope this gives you something to think about this week.

A special thanks to this week's sponsors: Bilt: if you are looking to level up your rewards game, time to check out how to get something back for your biggest annual expense: your rent or mortgage. Check out joinbilt.com/tyler today. Copilot Money: it's rare that I recommend apps to my friends, but when I do, it's because they're actually useful and dialed on what we need in finance. Check out try.copilot.money/tyler to see if Copilot Money is right for you. Gelt: I've said it before, and I'll say it always: if you haven't prioritized finding the right tax partner as a high net worth individual or business owner, you're prioritizing the wrong things. Check out joingelt.com/tyler today. A simple retirement plan is easy to explain. Living with it is harder. In this episode, Tyler revisits his 90% stocks / 10% money market retirement strategy ? not to defend it, but to answer the practical questions that matter: When do you cut spending? When do you increase it? How do you rebalance without overreacting? And how do you rebuild cash after a downturn without missing the recovery? This is the execution episode. In this conversation, Tyler covers: How to use guardrails to adjust spending automatically When to reduce withdrawals ? and when to raise them How often to rebalance (once a year is plenty) Why you only replenish cash after markets recover How automation keeps emotions out of the process The strategy remains intentionally simple: spend from cash during downturns, rebalance annually, and let math ? not headlines ? drive decisions. This episode isn?t about market timing. It?s about having rules in place so you don?t panic when volatility shows up. If the original 90/10 allocation made sense to you, this episode shows you how to actually stick with it. And if the show?s been helpful, leaving a quick review on Apple or Spotify genuinely helps. Hope this gives you something to think about this week.

A massive "thanks," as always, to this weeks's sponsors: Anthropic: I use Claude every hour of every day to optimize my life. If you haven't explored what Claude can do for you and your business, it's time. Check out Claude today at claude.ai/tyler LMNT: I drink LMNT before and after each workout, and I have never felt better. Mango Chili and Watermelon Salt are my go-tos, and take advantage of the sampler pack, so you can find yours today. Check out LMNT before your next workout at drinklmnt.com/tyler Facet: I continue to partner with Facet in 2026 because I have yet to find a financial planning resource more fitting and cost effective for my audience. Check them out today to see where you've been leaving money on the table. Go to facet.com/tyler to learn more. And now on to the show notes! At some point, the financial industry starts telling you that once you cross a certain number ? $5 million, $10 million ? you need something more sophisticated. In this episode, Tyler explains why that?s mostly nonsense. After his ?How to Invest $2 Million? episode, the big follow-up question was whether wealth changes the strategy. The answer: it doesn?t. The fundamentals stay the same ? time horizon, asset allocation, tax efficiency, fees, and real diversification. In this episode, Tyler breaks down five portfolio options: One fund (VTI or VOO) for maximum simplicity Two funds (stocks + bonds) for risk control Target date funds for true autopilot investing The three-fund portfolio for global diversification The five-fund ?2.0? version for small allocations to real estate, gold, or crypto None require hedge funds. None require private equity. None require paying 1% for unnecessary complexity. Tyler also explains why ?accredited investor? status often just means you?re being sold something expensive ? and why many ultra-wealthy investors still stick with index funds. This episode isn?t about leveling up your portfolio. It?s about keeping it simple ? no matter how much money you have. If the show?s been helpful, leaving a quick review on Apple or Spotify genuinely helps. Hope this gives you something to think about this week.

If you're interested in learning more about this week's partners: Copilot Money: I rarely recommend financial apps to my friends, but after suggesting that a few of my friends (all of whom work in finance) check out Copilot Money, not only did they all sign up, but they all think it's the best money app they've seen to date. So if you want to get your financial life in order, check out Copilot Money today at try.copilot.money/tyler. Gelt: My biggest business mistake to date? Waiting too long to establish a relationship with a reliable and proactive tax strategist. I left tens of thousands on the table. If your business is consistently netting over $200k, and you're lost as to next steps, you need to check out Gelt today at joingelt.com/tyler. And on to the show notes! Most retirement advice sounds confident and means almost nothing. ?Save a million.??Ten times your salary.??Seventy percent of your income." None of that tells you what you actually need. In this episode, Tyler walks through how to calculate your real retirement number ? one based on your spending, your timeline, and the kind of life you actually want. The goal isn?t motivation. It?s clarity. Instead of vague targets, Tyler breaks retirement planning into three practical numbers: Traditional FIRE ? the ?never work again? number, and why it?s too extreme for most people Coast FIRE ? the Goldilocks option that lets you save hard early and ease off later The bare minimum ? a realistic bridge for people closer to retirement who need options, not perfection Along the way, he explains why investing matters more than saving alone, why time beats contribution size, and why conservative assumptions create flexibility instead of fear. This episode isn?t about chasing a magic number. It?s about knowing what you?re building toward ? so you can stop guessing and start making decisions with confidence. If you?ve ever wondered whether you?re on track, this episode gives you a framework you can actually use. And if the show?s been helpful, leaving a quick review on Apple Podcasts or Spotify genuinely helps. Hope this gives you something to think about this week.

A massive thank you to those who make this show possible! Facet: Every January we obsess over physical health. But what about your financial health? If you're ready to actually get a plan instead of just hoping for the best, Facet pairs you with CFP® professionals who build personalized strategies for a flat fee. Head to facet.com/tyler to get $250 into your brokerage account when you invest $5,000 in your first 90 days, plus waived enrollment fees for new annual members. Fabric: If anyone relies on your paycheck, term life insurance isn't optional?it's the safety net that catches them if you're not there. Fabric by Gerber Life lets you apply online in ten minutes with no health exam, and a million dollars in coverage often costs less than a dollar a day. Head to meetfabric.com/tyler to get covered before you finish your coffee?policies issued by Western-Southern Life Assurance Company, not available in certain states, prices subject to underwriting. And now on to the show notes! Saving money for retirement gets all the attention. Spending that money intelligently is the hard part. In this episode, Tyler tackles the part of retirement no one really teaches: how to draw down your money without running out, losing sleep, or overpaying in taxes. Accumulation is mostly math and discipline. Decumulation is judgment, flexibility, and understanding tradeoffs. This is a practical walkthrough of dynamic retirement income strategies ? not rigid rules ? and why the approach your parents used probably doesn?t work anymore. In this episode, Tyler breaks down: Why retirement drawdown is harder than saving ? and why there?s no single ?right? rule The three main income strategies in retirement: selling growth assets, living off dividends, and fixed income How the 4% rule actually works ? and why it shouldn?t be followed blindly The pros and cons of dividend-focused portfolios, including tax implications When bonds, ladders, and annuities can make sense as income stabilizers Why inflation is the silent risk most retirees underestimate The most tax-efficient order to withdraw from accounts How Roth conversions, low tax brackets, and timing can save real money Along the way, Tyler explains why flexibility beats optimization, why peace of mind matters as much as returns, and why most retirees end up using a blend of all three strategies, not just one. This episode isn?t about squeezing every last dollar out of your portfolio. It?s about making your money last long enough to enjoy it ? and knowing how to adapt as markets, taxes, and life change. If you?re approaching retirement, thinking about early retirement, or just want to understand how the endgame actually works, this episode gives you a solid framework to start from. And if the show has been helpful, leaving a quick review on Apple Podcasts or Spotify genuinely helps. As always, hope this gives you something worth thinking about this week.

This week's episode is brought to you by: Facet. They provide you with access to a team of fiduciary CFP® professionals who gets paid to help you?not to sell you whole life insurance to fund their boat payment. New year, new financial plan that actually makes sense. Learn more at joinfacet.com/tyler. Copilot Money. The only finance app I've ever recommended to friends unprompted. Three finance professionals signed up, all three stuck around?which tells you everything. If you want to actually organize your money without turning it into a part-time job, check it out at try.copilot.money/tyler. Gelt. I spent six months doing everything right in my business?automated savings, proper accounting, the works?except I forgot to get a tax strategist. Rookie move. Should've been the first call, not an afterthought. If you're running a small business or a high earner, don't make my mistake. Check out joingelt.com/tyler. And on to the show notes! Most of what the insurance industry sells falls somewhere between unnecessary and borderline predatory. That?s not hyperbole. That?s the point of this episode. Here, Tyler breaks down what insurance is actually for, what you truly need, and why so many popular policies are aggressively oversold, misunderstood, or designed to benefit everyone except the person buying them. This is a blunt, behind-the-scenes look at how insurance really works ? informed by Tyler?s time inside the finance industry ? and why mixing insurance with investing is almost always a mistake. In this episode, Tyler covers: What insurance is meant to do ? protect against catastrophic loss, not build wealth The short list of insurance most people actually need Why whole life insurance is a bad deal for nearly everyone How indexed and variable life policies repackage the same problems with more complexity and fees When annuities can make sense, and when they don?t Why HSAs are one of the most powerful financial tools available, if you?re eligible Along the way, Tyler explains how commissions shape ?financial advice,? why bad products stick around, and how to spot sales tactics dressed up as planning. This episode isn?t anti-insurance. It?s about using insurance for what it?s good at ? transferring risk ? and avoiding products that pretend to be investments. And if the show has helped you avoid a mistake ? or ask better questions ? leaving a quick review on Apple Podcasts or Spotify genuinely helps. Hope this gives you something useful to think about this week.

This week's endeavor in free financial literacy for all, brought to you by: LMNT: You can have all the money in the world, but if you don't feel good physically, none of it matters. For years, I'd finish my morning workout and be foggy-headed with a headache by 1 PM?turns out I was chronically under-hydrated and needed actual electrolytes, not just water. LMNT has 1,000mg sodium, 200mg potassium, 60mg magnesium, and zero sugar that keeps me sharp all day. My routine: one during my workout, then a Sparkling LMNT around 4 PM (Mango Chili is the move). Right now they're offering a free sample pack with any purchase at drinklmnt.com/tyler. Bilt: I spent my late 20s throwing thousands at rent in Vermont while maxing out retirement accounts, feeling like I was getting nothing back. ?Bilt? fixes that by turning rent and mortgage payments into actual rewards?flights, hotels, fitness classes, or Amazon purchases. Join at ?joinbilt.com/Tyler? and make money you're already spending work harder. Facet: Every January we prioritize physical health like it's the New Year's resolution Olympics, but why don't we give our financial health that same energy? I get hundreds of messages weekly asking for personalized advice, and while I want to help, I can't responsibly address your specific situation in a podcast. That's why I partner with ?Facet?: you get dedicated CFP® professionals who build actual financial plans tailored to your life, charging a flat fee instead of a percentage of assets. Connect with Facet at ?facet.com/tyler? and start 2026 with both your health and your wealth dialed in. And on to the Show Notes! Somewhere between "retire at 30" and "work until 70," there's a middle path. Tyler talks with Andy Hill, host of Marriage, Kids and Money and author of Own Your Time, about how he and his wife reshaped their financial life to work 20?25 hours a week while staying financially secure?without winning the lottery or selling a tech company. This isn't a FIRE hype episode. It's a grounded conversation about tradeoffs, mistakes, marriage tension, and building a life that doesn't feel like a trap. Tyler and Andy discuss why extreme FIRE often breaks down in family life, how "Coast FIRE" creates a realistic middle ground, why income growth matters as much as cost-cutting, how money conversations can go wrong in marriage, and what it actually took to leave corporate work without blowing up financial security. Andy shares three concrete starting steps for anyone who feels stuck or burned out and wants to reclaim control over their time. This episode isn't about escaping work?it's about finding work you don't need to escape from. If the show has been helpful, leaving a quick review on Apple Podcasts or Spotify genuinely helps more people find it.

A massive thank you, as always, to this week's sponsors: ?Copilot Money?: Want to actually see where your money goes without judgment or manual spreadsheets? ?Copilot Money? connects all your accounts in one place, tracks subscriptions automatically (no more surprise renewals), and uses AI to categorize spending so you're not tagging transactions like a digital archaeologist. It's privacy-first (they don't sell your data), and they're an Apple Design Awards finalist. Use code TYLER at ?copilot.money? for two free months, plus 26% off your first year for new users. If you're starting 2026 wanting clarity around your finances, this is worth trying?especially for free. Gelt: If you're like me, a solopreneur or a high net worth individual, and you do NOT want to make managing your taxes a SECOND full time job, visit Gelt today and see what they can do to turn your tax strategy around in 2026 and let YOU get back to doing literally anything else. Visit joingelt.com/tyler to see if they're the right fit for you and your business. ?Fabric?: And if you have ANYONE who depends on your income, term life insurance is essential. That's why it's Step 3 in my financial order of operations, long before an emergency savings account or funding a Roth IRA. This is what will actually help the family if something happens to you. And you can get covered in ten minutes from your couch while watching Survivor. Go to ?meetfabric.com/tyler? today and get the coverage you need. And on to the show notes! Rebalancing gets treated like financial gospel. Something you must do on a strict schedule, or else you?re somehow being irresponsible with your money. In this episode, Tyler pulls that idea apart. Yes, rebalancing matters ? but it?s far less urgent, far less precise, and far less sacred than the financial industry wants you to believe. This is a practical, anxiety-reducing look at what rebalancing actually is, when it?s worth doing, and when you can probably stop worrying and go live your life. In this episode, Tyler breaks down: What rebalancing actually means, and why age-based formulas are mostly nonsense Why goals matter more than age when deciding your allocation When rebalancing barely changes outcomes ? and when it actually matters How target date funds handle rebalancing for you, and when they work well How to rebalance yourself without overthinking it, especially inside retirement accounts Why rebalancing in taxable accounts is trickier, and when paying taxes is actually the right move How to rebalance using new contributions instead of selling ? and why taxes shouldn?t paralyze you Along the way, Tyler explains why rebalancing isn?t about hitting a perfect allocation, why most people exaggerate its importance, and why alignment beats optimization every time. This episode isn?t about micromanaging your portfolio. It?s about making sure your money still reflects your goals ? and knowing when you can safely stop tinkering. If you?ve ever wondered whether you should rebalance, whether it?s worth triggering taxes, or whether you?re overthinking the whole thing ? this one?s for you. And if the show has been helpful, leaving a quick review on Apple Podcasts or Spotify genuinely helps. It helps other people find the show and keeps it going. As always, hope this gives you something useful to think about this week.

Here are some truly helpful resources from this week's sponsors: First, the ONLY way I am able to make this much content, day in day out, is by feeling my best. Always. And that starts with my working out each morning and needing something that doesn't leave me feeling like I just ate four pounds of candy. Enter LMNT. It is literally the product designed for people like me: need the fuel, don't need the crash, game on. Check out LMNT today here. And if you're looking to start 2026 with a bang, like, a "get my act together financially once and for all" type bang, check out Facet. They continue to practice what I preach, and they provide real advice from real experts for real people. Check them out today here. And now on to this week's the show notes! Most people say they believe in long-term investing. Far fewer people actually behave like it ? especially when markets are at all-time highs. In this episode, Tyler tackles one of the most common (and expensive) investing mistakes there is: sitting in cash while waiting for the ?right time? to invest. The twist? That ?right time? almost never shows up, and the data is brutally clear about what it costs. Despite how uncomfortable it feels, buying stocks at all-time highs has historically been a perfectly reasonable ? and often superior ? strategy compared to waiting on the sidelines. In this episode, Tyler walks through five reasons why staying in cash is costing you a fortune: All-time highs are normal ? markets hit them far more often than most people realize Even terrible timing beats no timing ? buying at the worst possible moments still outperforms sitting in cash ?This time is different? almost never is, no matter how convincing the headlines sound Missing the best days destroys long-term returns, and those days often arrive during chaos Doing nothing is still a decision ? and it carries real risk Along the way, Tyler breaks down decades of market history, real return data, and behavioral traps that convince smart people they?re being cautious when they?re actually sabotaging themselves. This episode isn?t about ignoring risk or investing recklessly. It?s about recognizing that waiting for certainty is just another way to lose money. Markets go up. Markets go down. But sitting in cash while hoping to outsmart two centuries of economic progress has never been a winning strategy. If you?ve ever told yourself you?re ?just waiting for a pullback,? this episode is for you. And if this helped you rethink your approach ? or finally get out of your own way ? leaving a quick review on Apple Podcasts or Spotify genuinely helps. It helps other people find the show and keeps this whole thing moving. As always, hope this gives you something useful to think about this week.

For those of you looking for more helpful resources, check out the amazing companies that make this endeavor in free financial literacy possible: 1) If you are running small business and DON'T want to make your taxes yet ANOTHER small business, check out Gelt today. They can help small business owners and high net worth individuals who are looking for strategy beyond filing. 2) And if you are tired (as I was for WAY too many years) of paying rent and feeling as if you were getting nothing in return, check out Bilt, and consider joining their renters' loyalty program. It is an amazing way to -finally- get something back after years of feeling like you're throwing money towards someone else's equity. Most people spend a lot of time obsessing over what to invest in. Very few people think seriously about where those investments should live ? and that mistake can cost you tens of thousands of dollars over a lifetime. In this episode, Tyler breaks down account placement strategy ? the unglamorous, aggressively unsexy topic that quietly determines how much of your money you actually get to keep. Because just like real estate, with investing it?s all about location, location, location. This isn?t about finding the perfect fund. It?s about putting the right investments in the right accounts. In this episode, Tyler covers: The three main types of investment accounts ? tax-deferred, tax-free, and taxable ? and what each one is actually for Why taxes matter more than most people realize, and how bad account placement creates avoidable tax bills Which investments belong in retirement accounts (and which absolutely don?t) How access and liquidity should shape where your money lives, especially if you want flexibility before retirement Why volatility feels different depending on the account, and how to use that to your psychological advantage Real-world examples showing how small placement changes can save real money over time Along the way, Tyler explains why ?max everything and figure it out later? isn?t always smart, how over-locking money can quietly limit your life choices, and why the goal isn?t tax perfection ? it?s alignment. Alignment between your accounts, your investments, your time horizon, and the life you actually want to live. This episode isn?t about optimizing every dollar with spreadsheets and IRS tables. It?s about not making preventable mistakes. Put tax-inefficient investments where they?re protected. Put volatile investments where you?re less likely to panic. Put short-term money where you can actually reach it. And stop throwing money into random accounts and hoping it works out. If this episode helped something click ? or made you realize you might want to move a few things around ? leaving a quick review on Apple Podcasts or Spotify genuinely helps. It helps other people find the show and keeps this whole project going. As always, the goal isn?t perfection. It?s getting one step closer to alignment. Hope this gives you something to think about this week.

This week's helpful resources: Fabric (term life) and Gelt (small business taxes). Term life insurance sits at step three in my financial order of operations?before your emergency fund?because if something happens to you, it becomes the emergency fund for everyone you leave behind. Get covered in ten minutes at meetfabric.com/tyler. If you're a small business owner or high net worth individual, finding the right tax partner isn't optional?it's the first domino that determines whether you keep your money or hand it to the IRS. Start with a free consultation at joingelt.com/tyler. And now back to the show(notes!) :) Most investing mistakes don?t feel like mistakes while you?re making them. They feel reasonable. Sometimes they even feel responsible. In Part 2 of this behavioral economics series, Tyler moves past the ?greatest hits? and into the deeper, quieter biases that don?t get talked about as much ? but are still quietly wrecking portfolios day after day. Think album tracks, not radio singles. If Part 1 was Madison Square Garden, this episode is the smaller venue where the real damage happens. In this episode, Tyler breaks down five lesser-known behavioral biases: The Disposition Effect ? why we sell winners too early and cling to losers too long The Ostrich Effect ? how avoiding uncomfortable information can sabotage your plan Mental Accounting ? why treating dollars differently based on where they came from is costing you real returns The Gambler?s Fallacy ? how seeing patterns in randomness leads to terrible timing The Action Bias ? why doing something often feels better than doing the right thing (which is usually nothing) Along the way, Tyler explains why these behaviors feel correct in the moment, why willpower doesn?t fix them, and why most investors don?t need better predictions ? they need better systems. Automation. Rules. Fewer decisions. Less fiddling. This episode isn?t about becoming more active or more sophisticated. It?s about accepting a hard truth: successful investing is supposed to be boring. If it?s exciting, you?re probably paying for that excitement with your returns. If this episode helped you recognize one habit you need to break ? or one urge you need to stop indulging ? leaving a quick review on Apple Podcasts or Spotify genuinely helps. It helps other people find the show and keeps this whole experiment going. Until next time, remember: the best investors aren?t the smartest. They?re the ones who do the least amount of dumb stuff.

Here are a few helpful resources from the people who support this show and keep it free for you. Always.  If you?ve ever wondered whether you?re doing ?fine? with your money or just hoping future-you figures it out, Facet sets you up with a team of expert CFP® professionals who look at your entire financial life ? not just your investments, and not just the parts that are fun to talk about at dinner parties. No commissions. No product pushing. Just real advice for one flat annual membership fee.  If you're interested in heading into 2026 with a real financial plan from real experts, check out Facet today, here. -- Most people don?t lose money because they pick terrible investments. They lose money because they?re human. In Part 1 of this two-part series on behavioral economics, Tyler walks through the five most common psychological biases that quietly, systematically sabotage investment returns ? even when you?re invested in low-cost index funds and ?doing everything right.? This episode is about the stuff that happens between your ears. The mental shortcuts. The overreactions. The stories we tell ourselves after the fact. In this episode, we cover: Why overconfidence makes investors trade more and earn less How recency bias convinces us that whatever just happened will keep happening Why we overvalue the investments we already own (even when we shouldn?t) How loss aversion turns normal market volatility into bad decisions Why hindsight bias makes the past feel obvious and the future feel predictable (it isn?t) This isn?t about being smarter than the market. It?s about building systems that protect you from your own instincts ? automation, diversification, fewer decisions, and a little less checking. If the show has helped you think differently about money ? maybe even made you laugh while doing it ? please take 30 seconds to leave a review on Apple or Spotify. It helps more than you think and keeps this whole experiment in free, digestible financial literacy alive and well.

Here are a few helpful resources, from those who continue to make this show possible for and accessible to you. Visit them today to learn more! To experience what you've been missing by paying rent without getting some amazing rewards along the way, check out how Bilt can help you, here. And if you're like me and have started a small business and don't want to make managing your taxes your SECOND business, explore Gelt today, here. There?s something oddly therapeutic about deciding what not to do with your money next year. Like a financial New Year?s resolution ? but with fewer spreadsheets and way less kale. In this episode, Tyler flips the usual ?5 things millionaires do? format on its head and shares the five things he refuses to do with his money in 2026. From why he won?t pay off his mortgage early to why high-yield savings accounts aren?t the financial flex you think they are, this episode is all about resisting motion for motion?s sake and reclaiming simplicity in a culture obsessed with doing more. You?ll learn: Why not paying off your mortgage early can actually make you money (hint: opportunity cost). Why high-yield savings accounts aren?t as ?safe? or ?smart? as they seem ? and what to use instead. The trap of saving or investing just to feel responsible, and how to reconnect your money with purpose. Why spending for the sake of deductions is just expensive procrastination (and how to stop doing it). How to keep your portfolio simple ? and why complexity almost always costs more than it earns.Tyler reminds listeners that real wealth isn?t about doing more ? it?s about doing less, better. This is your invitation to create your own ?Not To Do? list for 2026: the habits, purchases, and pressures you?re done with. If the show has helped you think differently about money ? maybe even made you laugh while doing it ? please take 30 seconds to leave a review on Apple or Spotify. It helps more than you think and keeps this whole experiment in free, digestible financial literacy alive and well.

If you?ve ever wondered how to invest $2 million?or any substantial portfolio?without losing sleep, this episode is for you. I break down a simple, historically backed approach: 90% in stocks (VOO/VTI), 10% in a money market fund (SPAXX). This allocation maximizes growth, keeps volatility manageable, and allows you to spend confidently. We challenge conventional wisdom: the 4% rule is too conservative for most retirees. With disciplined withdrawals of $120k?$200k per year, your portfolio can keep pace with inflation, fund meaningful experiences, and still grow over time. Think of it as the financial equivalent of having your cake, eating it, and watching it regenerate. We also tackle the psychology of spending: most retirees underspend, living smaller than necessary due to ?consumption gap anxiety.? Intentional withdrawals for travel, family experiences, and ?bucket list? adventures can bring more lasting happiness than accumulating wealth alone. Historical context matters: even through market crashes?2008, 2020?you can maintain your lifestyle using a 10% cash buffer. Percentages matter more than principal; the strategy scales from $500k to $20M. And if it's good enough for Buffett's estate...it's good enough for me. Key Highlights: Percentages over principal: 90/10 allocation works for nearly any portfolio size. Withdraw confidently: $120k?$200k/year supports lifestyle while portfolio grows. Spend for experiences: vacations, relationships, and quality of life matter more than hoarding. Liquidity is your friend: 10% in cash lets you ride out crashes without selling stocks. High-stakes bingo: later in retirement, increase withdrawals for ?once-in-a-lifetime? experiences. Resources and research mentioned in this episode: William Bengen, 4% Rule (1994) Michael Kitces on dynamic withdrawals Wade Pfau, Safety-First Retirement Planning Bill Perkins, Die With Zero David Blanchett, Retirement Spending Smile If this episode helps you feel more confident about using your money to live well, consider leaving a review on Apple or Spotify. Your feedback helps keep this financial literacy experiment alive. And if you're still feeling stuck and are looking for expert advice for a flat annual membership fee, check out this episode's sponsor, Facet, by going to facet.com/tyler

Not all ?no-income-tax? states are created equal?and some of the states you?ve been avoiding might actually be financial hidden gems. In this second installment of our two-part series on retirement locations, we dive deep into the numbers behind effective tax rates, deductions, and exemptions, revealing which states quietly reward retirees and which can quietly drain your life savings. Highlights from this episode include: The Unexpected Winners: Iowa, Pennsylvania, and New Jersey come out on top for tax efficiency. Yes, New Jersey can be a retirement hero under the right circumstances. The Surprising Losers: Oregon, Minnesota, Hawaii, and New Mexico might make your retirement dream feel expensive, despite gorgeous scenery or ?low-tax? branding. Marriage Matters: Married couples can save up to six percentage points in taxes?enough to turn a modest nest egg into a significantly more comfortable retirement. Why Effective Tax Rate is King: Forget slogans and state income tax lists. The only number that really matters is what you actually pay after all deductions, exemptions, and costs are considered. But beyond taxes, and this is primarily why I made this a two-parter, we explore why happiness, community, and lifestyle often matter more than the spreadsheets. Retiring in a state just because it looks cheap might save you a few dollars but cost you your sense of home. The best retirement state balances financial security with quality of life. If you enjoyed this episode, leave a review on Apple Podcasts or Spotify, or share it with a friend planning their retirement. And if you missed Part 1, we highly recommend listening to last week?s episode to get the full story on The Great Tax Mirage and why ?no state income tax? can be misleading. And if you're interested in learning more about this week's sponsors, the amazing companies who allow this free content to get to you week after week after week, check them out here: For the single best electrolytes drink I have found to drive and sustain my energy on a daily basis: drinklmnt.com/tyler And for those small business owners who are as overwhelmed as I am about learning the ins and outs of optimizing our taxes: joingelt.com/tyler

Everyone will tell you to move to Florida or Texas to retire tax-free. But the truth? Taxes are more complicated than a ?No State Income Tax? billboard. In this first part of a two-part series, we unpack The Great Tax Mirage and reveal why some so-called high-tax states like New Jersey, Pennsylvania, and Iowa may leave retirees with more money in their pocket than the sunny paradises they?re fleeing. We dive into Fidelity?s latest study modeling retirees withdrawing $100,000 a year from an IRA and show how effective tax rates?what you actually pay after exemptions and deductions?can dramatically flip conventional wisdom on its head. For example, a couple retiring in Oregon might pay close to 13% in effective taxes, while a move to Iowa could drop that number to 7.5%, potentially growing tens of thousands of dollars over a decade. We also explore the underrated power of marriage in retirement planning. Married couples filing jointly can save around six percentage points on combined federal and state taxes versus singles?enough to add tens of thousands of dollars to a nest egg over ten years. Key takeaways from this episode include: No state income tax doesn?t automatically mean you keep more money. Certain high-tax states offer exemptions and deductions that outperform so-called tax havens. Marriage can be one of the most powerful retirement tax strategies. Your effective tax rate?not the headline rate?determines what you actually keep. Planning where to retire is about life satisfaction as much as taxes. Whether you?re dreaming of beaches, cornfields, or just a comfortable, worry-free retirement, this episode will change the way you think about where your money?and your life?goes next. Part Two drops next week, where we?ll rank the best and worst states for retirees, explore the real impact of marital magic, and dig into other often-overlooked factors that matter more than taxes when choosing where to spend your golden years. If you enjoy the show, please leave a review on Apple Podcasts or Spotify and share it with a friend who?s plotting their retirement escape. It helps more than you know?and makes sure that no one accidentally retires somewhere that quietly nibbles their nest egg.

This is part two of our financial order of operations series. In part one, we covered the non-negotiables?the oxygen mask, debt payoff, insurance, and the foundation of every real financial plan. This week, we get into the gray areas. The places where conventional wisdom isn?t just outdated?it?s expensive. Here?s what we cover: 7?? The Emergency Fund MythYou?ve heard it before: ?Keep six months of expenses in cash.? The problem? That advice was built for a world where savings accounts paid double-digit interest. Today, it?s fear-based and mathematically backward. Most people will go years without a true financial emergency, and keeping $20,000 in cash for a maybe costs far more than it saves. Learn how to balance liquidity with growth without putting your future on pause. 8?? The Taxable Brokerage Account AdvantageOnce you?ve maxed your Roth IRA, captured your 401(k) match, and funded your HSA, it?s time to open a taxable brokerage account. This is your flexibility play?your bridge between today and retirement. Access your money anytime, invest in low-cost index funds, and take advantage of long-term capital gains rates that beat most income taxes. 9?? The Right Way to Think About DebtDebt isn?t moral?it?s mathematical. If your rate is above 5%, pay it off first. If it?s below 5%, investing probably wins over time. But if it?s keeping you up at night, pay it off anyway. Personal finance is personal?and peace of mind compounds, too. ? Bonus: The 20-Minute ?Tiered Pricing? HackCall your phone, internet, and streaming companies once a year. Tell them you?re considering canceling. Decline their first ?special offer,? and watch the discounts appear. It?s the modern coupon?no scissors required?and it can save you $1,000+ a year to redirect into your investments. At the end of the day, this two-part series gives you a complete, math-first roadmap for building wealth that lasts. It works whether you?re starting out or managing seven figures. And if you're interested in learning more about this week's show sponsor, Facet, check out facet.com/tyler today to learn more! ? Listen now wherever you get your podcasts.  ? Join the newsletter for weekly financial clarity (and the occasional heretical take): https://socialcapconnect.substack.com/subscribe

This week we?re tearing apart one of personal finance?s most overused frameworks: the ?financial order of operations.? You?ve heard a version of it before?pay this, save that, sacrifice now, maybe retire someday. The problem? Most of those systems were built by people who either (a) never had real financial stress, or (b) have spent too long in the Dave Ramsey cinematic universe. So, I rebuilt the order from scratch. And it actually works in the real world, whether you make $40,000 or $400,000. Here?s what we cover: 1?? Put your own oxygen mask on first.Take care of yourself before your kids. Financial stability isn?t selfish?it?s responsible. 2?? Obliterate credit card debt.The ?snowball method? is financial astrology. Attack the highest-interest balance first. 3?? Get insurance.If someone depends on your income, you need term life and long-term disability. No gimmicks. 4?? Max out your Roth IRA.It?s flexible, tax-free, and doubles as a stealth emergency fund. 5?? Grab your 401(k) match.A 50% employer match is the only free lunch on Wall Street. 6?? Max out your HSA (if you can).The triple tax advantage?deductible going in, tax-free growth, tax-free withdrawals?is unbeatable. We?ll go deeper into emergency funds, taxable brokerage accounts, and smart debt strategies in Part 2 next week. And a MASSIVE thank you to this episode's sponsor, Facet. If you are tired of paying more to an advisor simply because you make more, check out facet.com/tyler today to learn more.  ? PLUS: stick around until the end of the episode for a modern trick that helps you find the money to do all of this in under 20 minutes?without canceling Netflix or giving up your morning coffee. If this episode helps you?or if you simply enjoy hearing someone roast bad financial advice with love?please consider leaving a review on Apple or Spotify or share this with a friend who still believes paying off a $200 credit card before a $20,000 one is ?confidence building.? ? Listen now wherever you get your podcasts.  ? Join my newsletter for weekly financial philosophy that treats you like an adult: https://socialcapconnect.substack.com/subscribe

What if you could skip the index fund and build your own? In theory, you can. In practice?well, it?s a bit like building your own refrigerator. You?ll learn a lot, and maybe even get a working model, but you?ll also discover why the factory-made version is so efficient in the first place. In this episode, we dive into the peculiar urge to ?DIY? the market, and why the exercise can be incredibly educational?even if you never actually follow through. Along the way, you?ll learn: The 11 Sectors of the Market: From flashy Tech to steady Utilities, every portfolio starts with understanding the cast of characters. How Benchmarks Really Work: Why the S&P 500 is more active (and more tax-efficient) than most people realize. The Temptation of Tilts: When to add seasoning like value or small-cap, and when ego is just disguising speculation. Building Your Own Fund: How to use sector ETFs to replicate the market?and why rebalancing can become a full-time job. Keeping Costs and Ego Down: The S&P?s hidden advantages in cost and tax efficiency, and why humility may be the cheapest asset in your portfolio. The takeaway? You can build your own index fund. You might even enjoy the process. But the real lesson is what it reveals: index funds are masterpieces of design, combining diversification, tax efficiency, and ruthless discipline?all while letting you spend your time on things that matter more than spreadsheets. And if you are interested in learning more about those who support this content and make the show possible, visit facet.com/tyler today! And see why they're the only partner I've brought to you thus far as a resource.  ? If you found this episode useful (or at least more entertaining than quarterly earnings reports), please leave a review on Apple Podcasts or share it with a friend. It?s the best way to help the show grow?and keeps me from muttering about sector weights to myself in the Vermont woods.

Your 50s are a tax-planning sweet spot?a decade when smart strategies can save you tens or even hundreds of thousands over the course of retirement. In this episode, Part Two of our two-part series, we explore four advanced but practical moves to keep more of your money compounding where it belongs. Here?s what we cover in this episode: The HSA Triple Play: Why this account is the most underrated retirement tool, and how to turn it into a stealth IRA with triple tax benefits. Social Security Timing & Taxes: How your claiming age affects not just your benefit but how much the IRS quietly takes back. Charitable Giving with Donor-Advised Funds: A Costco-sized deduction now, with the ability to give on your terms for years. Plus, how Qualified Charitable Distributions can kill two birds with one IRA. Bracket Shifting by Gifting to Kids: Move money to lower tax brackets within your family?legally?while supporting education, housing, or even a responsible jet ski purchase. Together with Part One (Roth conversions, withdrawal sequencing, and tax-efficient investing), this gives you a full seven-strategy toolkit for your 50s. No gimmicks, no offshore shell games?just thoughtful planning that keeps more money in your pocket and less in Uncle Sam?s. ? If this series has been helpful, please leave a review or share it with a friend. It?s the best way to help the show grow?and it keeps me from muttering about Roth conversions to my dogs in the Vermont woods without witnesses.

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 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. Front-load value. Pitch with a one-pager or mini-audit tailored to the company?proof you?ll do the work. 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. Prepay strategically. Use prepayment to align behavior with values (fitness classes, transit, annual memberships). 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

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: 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.

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: 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 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.

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 ignore How sequence of returns risk can silently wreck your plan Why portfolio size and asset allocation matter far more than a static percentage Smarter, more dynamic strategies to adjust year-by-year If 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 [email protected]. This show is for you, and we want it to be as good as it can be.

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 Buy a New Car Without Getting Screwed? Today?s guest is someone whose work has quietly and profoundly shaped how a generation thinks about money. JL Collins is the author of The Simple Path to Wealth, a personal finance classic that has empowered hundreds of thousands to think differently about investing, independence, and freedom. In this conversation, JL and I explore the real meaning behind financial independence ? not retiring early, but reclaiming your ability to say no. We go back to the moments that shaped his life philosophy: the bold four-month leave he took just two years into his first job, the decision to convince his wife to leave her job while he wasn?t earning a paycheck, and the early desire to build what he calls FU money ? not to quit work, but to buy back control. We revisit Black Monday in 1987 and how that shaped JL?s views on market volatility, risk, and emotional discipline. He shares how a humbling mistake helped hardwire the importance of staying the course, and how index investing eventually became the core of his life?s message: simplify. We also talk about the new edition of The Simple Path to Wealth, what?s changed, what hasn?t, and how his daughter went from being the reluctant listener to co-pilot on the updated edition. This is a conversation about money, yes ? but more than that, it?s about living deliberately. JL reminds us that wealth isn?t about what we can afford ? it?s about what we no longer have to worry about. You?ll hear about: How JL built his investing philosophy through trial and error Why VTSAX and chill remains his core guidance What it means to live in a world where, eventually, everything is "free" Why simplicity is a radical act in a noisy, complex world And why, if you get the money stuff right early, you can spend the rest of your life not thinking about it at all.

And in case you missed it, check out last week's episode of Your Money Guide on the Side with Mady Mills where we answered the question, Why do Billionaires Still Panic?  Car buying has become one of the most financially dangerous consumer experiences in modern life. In today?s episode, we?re flipping the script. Whether you?re buying or leasing, trading in or paying cash, I?ll walk you through the 10 timeless rules you must follow if you want to avoid getting taken for a ride?financially and emotionally. No guilt trips. No boomer advice. Just strategy, leverage, and power dynamics decoded. And full disclosure: I love cars. I lease new ones every few years. I?m not here to shame your joy. I?m here to make sure that joy doesn?t cost you $9,000 more than it should. WHAT WE COVER: Why you should never walk into a dealership first?and what to do instead The email script that can save you thousands before you ever test drive Why ?What can you afford monthly?? is a trap?and how it costs you big The hidden revenue center called the ?finance office? (and how to say no) The floor plan secret that gives you leverage when buying in stock How to use pre-approved financing as bait to beat the dealer at their own game Real math on depreciation?and why some ?investments? are worth it anyway When leasing makes more sense than buying (and what to negotiate) How emotional timing ruins deals?and how to buy before you need to The best days of the year to buy, based on actual dealer incentives Plus, why your car purchase might be one of the biggest financial decisions of your next five years?whether you realize it or not. MENTIONED IN THIS EPISODE: Kelley Blue Book average car prices (2024): $47,000+ CFPB, NADA, JD Power, Bankrate statistics on car loans, dealer profit centers, and interest rate games How to calculate a lease ?money factor? and negotiate like a pro The difference between buying a car and buying a feeling?and why that matters JOIN THE CONVERSATION: Have a question, a rant, or a car-buying story that others need to hear? Shoot me a note at [email protected]. I read every message. And if this show is helping you feel more powerful and prepared, the best way to say thanks is with a quick review. It helps the show grow and lets me keep delivering practical, real-world financial guidance?without selling out.

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 Invest $1,000,000? She?s been on Bloomberg. The New York Times. Yahoo Finance. But Mady?s real talent? Translating the chaos of markets and money into stories that make you feel seen. In this episode, we dive into everything from surviving the 2016 election newsroom to navigating the terrifyingly personal world of money and relationships. Mady opens up about growing up around volatility ? both financial and emotional ? and how it fuels her empathy-first approach to financial journalism today. We talk about: Why everyone, even billionaires, fears losing everything How to actually make money content more fun and accessible What David Booth (yes, that billionaire) thinks you should do instead of stressing about a stock crash How her background in political reporting shaped her calm, clear-eyed view of financial chaos The most important account a woman can open (hint: it starts with ?I? and ends with freedom) And the number one piece of advice for men in relationships?you?ll just have to listen and find out! This is one of those rare conversations that gets behind the curtain of financial media and your own money story ? and leaves you feeling a little smarter, a little braver, and a lot more equipped to have the hard conversations. Interested in learning more about and/or following Mady Mills? Instagram: @madymills TikTok: @madymills

And in case you missed it, check out last week's episode of Your Money Guide on the Side with Andrew Tobias where we answer the question, What is the easiest way to become wealthy? You've hit the million-dollar mark?now what? In this episode of Your Money Guide on the Side, we tackle the deceptively simple question: how should you invest a million dollars? This isn?t about theoretical asset allocation or textbook strategies. It?s about real lives, real goals, and real risk tolerance. We meet three investors?Chad, Nina, and Marge?each at very different life stages, each with a radically different approach to putting their wealth to work: Chad Slater, the thrill-seeking ex-startup bro who wants asymmetry, optionality, and upside. His portfolio is bold, volatile, and aggressive?global equities, venture capital, and yes, crypto. Nina Ellington, the grounded creative director turned Pilates instructor who wants growth without chaos. Her diversified, resilient mix of stocks, bonds, real estate, and alternatives prioritizes balance and autonomy over adrenaline. Marge Buttersworth, the sharp, independent retiree who wants reliability and peace of mind. Her income-focused portfolio features bond ladders, dividend stocks, and high-yield cash vehicles?designed to pay her, not stress her. These are not just asset allocations. They are reflections of who these people are, what they value, and what they need their money to do for them. ? Along the way, we explore key questions: How soon will you need the money? How much risk can you stomach? Are you trying to grow, preserve, or withdraw from your portfolio? And if you stick around until the end, I share exactly how I invest my own money?no hype, no secrets?just a simple, transparent walk through my personal allocation and why I chose it. ? In this episode, you?ll learn: 3 distinct investing strategies for $1M portfolios How risk tolerance, time horizon, and goals shape allocation The truth about fees, diversification, and asset class correlation Why your neighbor?s portfolio has nothing to do with yours How to evaluate your definition of enough ? Bonus: If this episode resonates, subscribe to my free weekly newsletter for deeper dives and personal stories at tylergardner.com  ?? Disclaimer: I?m not your financial advisor?I?m your guide on the side. Everything here is for educational purposes only. Always do your own research and consider working with a fiduciary advisor who understands your unique circumstances.

And in case you missed it, check out last week's episode of Your Money Guide on the Side where we answer the question, Should I Hire a Financial Advisor? What if the only investment guide you ever needed... actually was? This week, I sit down with personal finance legend Andrew Tobias?bestselling author, Harvard Business School grad, long-time political advocate, and the brilliant mind behind The Only Investment Guide You?ll Ever Need. His book was literally the first financial text I ever read, and it remains one of the few I return to over and over again?for its timeless principles, relatable tone, and surprising humor. In this conversation, we cover: The unlikely path from Slavic literature major to bestselling financial writer Why ?don?t be boring? might be the best writing advice you?ll ever get The epic laundry list of startup investments that went very sideways (and what he learned from each) The true cost of chasing returns vs. chasing happiness Why retirement isn't a finish line?but a lifestyle with the right people His most embarrassing investing losses?and how they became his favorite teaching tools Andrew doesn?t just teach people how to manage money?he shows us how to think about it, with warmth, wit, and an honesty that?s rare in finance. ? If you?ve ever wondered what makes financial advice stick?or how to build a life rich in meaning as well as money?this episode is for you. ? Subscribe, rate, and share if it resonates. And thank you for joining me on Your Money Guide on the Side.

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 talk to Others About Money?  This might be the most common money question I get, and maybe even the most important: Should I hire a financial advisor? And right behind it: If so, how do I find a good one? In today?s episode, I?m not giving you a yes or no answer (sorry, not sorry). Instead, I?m walking you through a three-part framework to decide if you need an advisor?skill, will, and time?and then I?m sharing seven real-world filters for choosing the right one if you do. Because the truth is: Working with a financial advisor might be one of the smartest moves you?ll ever make. Or it might be an expensive, unnecessary distraction. The difference lies in what you need and who you choose. We?ll talk about: The difference between CFP®, CFA®, CPA, and the rest of the alphabet soup What being a ?fiduciary? really means (and doesn?t mean) The myth of market-beating promises (run from those) Fee models that make sense?and those that don?t Why credentials are clues, but not the whole story How investing is often more about behavior than brilliance The one question you must ask every advisor: ?How do you invest your own money?? And yes, I even compare hiring a financial advisor to dating?because, honestly, it is. This episode won?t give you a rubber-stamped answer, but it will give you something far more valuable: a lens to look through so you can make the call yourself. ? Whether you?re DIY-ing your financial life or just trying to figure out if the grass really is greener with professional help?this one?s for you. If you enjoy the show, don?t forget to subscribe, leave a review, and share it with a friend who?s wondering if they should ?talk to someone? about their money. ? And as always, you can sign up for the free newsletter at tylergardner.com for more clear, action-oriented financial education.