Hack Your Wealth

#95: The biggest concern many would-be retirees have, at least in the US, is the cost of healthcare.Not only is healthcare more expensive in the US than in every other industrialized country. There's also no national health insurance system to control costs or standardize care quality…unless you're a senior or very poor (or both).In fact, were it not for worries about healthcare, there would undoubtedly be way more US retirees out there today. The average retirement age would drop noticeably.Because no less than your retirement security is at stake, healthcare financial planning is retirement planning.That's why I invited Bo Bowen to the podcast today to share his unique perspective on healthcare financial planning in retirement. Bo is both a healthcare practitioner (pharmacist) and a certified financial advisor who has specialized in advising on healthcare financial planning and retirement health insurance. His dual background gives him unique insight into the way healthcare financial planning is crucial for retirement security.We discuss:The biggest challenges retirees face when it comes to healthcare planningWhat retirees should think carefully about when it comes to health insurance in retirementHow those considerations change depending on your retirement ageChecklist for choosing the right health insurance plan if you're retiring soonCommon mistakes retirees make when planning for post-retirement healthcareWhen self-insuring might be your best choice in retirementHow medical tourism can play an important role in retirement healthcareWhat retirees should know about buying health insurance on ACA marketplace exchangesCheck it out here:https://hackyourwealth.com/health-insurance-retirement-planningIf you've already retired, what do you do for health insurance? Knowing what you know now, what (if anything) would you do differently in terms of healthcare planning in the years before retiring?If you have NOT retired yet, how big of a factor is healthcare and health insurance to your decision of when to retire?Let me know by leaving a comment.Don't miss an episode, hit that subscribe button...If you liked this episode, be sure to subscribe so you don't miss any upcoming episodes!Apple PodcastsOvercastSpotifyStitcherI need your help, please leave a listener review :)If you liked this episode, would you please leave a quick review on Apple Podcasts? It'd mean the world to me and your review also helps others find my podcast, too!Related links:https://www.healthinsurance.orghttps://www.healthcarebluebook.comhttps://www.medibid.comhttps://www.linkedin.com/in/bo-bowen-1b64341a6Schedule a private 1:1 consultation with meHYW private Facebook communityIntro/Outro: Old Bossa by Twin Musicom.

#94: Real estate investing changed a lot the last couple years, but one asset class consistently punched above its weight: short-term rentals, a.k.a., STRs, e.g., Airbnbs.In 2020, when people couldn't go on vacation by hopping on a plane to Europe, South America, or Asia, they got in their cars and drove to national parks and mountain / beach / lake towns. Short-term rentals, often seen as safer than hotels, were on

#93: Early retirees often fill their early years in retirement with lots of travel. There is even a vibrant community of nomadic early retirees who travel long-term.But what do you do about health insurance, especially if you're American? Unlike in most other industrialized countries that have universal health insurance, American health insurance is generally tied to your employer, at least before you're old enough to qualify for Medicare. That means if you don't have a job, you generally don't have health insurance. For early retirees, that's a problem.What are the health insurance options for early retirees, especially those who plan to travel significantly in retirement?This week, I chat about early retirement health insurance options with Tracy Winters, Director of Individual Insurance at Good Neighbor Insurance, an Arizona-based health insurance brokerage that specializes in health insurance consulting for long-term travelers, expats, and traveling early retirees.We discuss:The big picture for how traveling early retirees should think about their health insurance optionsWhen it makes sense to simply self-insureTracy's observations on which countries offer both high-quality and affordable healthcareTracy's health insurance recommendations for early retirees who wish to travel abroad 100% vs. 90% vs. 50% vs. 25% of the timeACA marketplace health insurance options to consider for early retireesHow Medicare coverage is impacted when you travel long-termWhen it's worth repatriating to the US vs. staying in-country to get medical care, plus what kind of insurance plans provide repatriation servicesCheck it out here:https://hackyourwealth.com/health-insurance-retirement-travelIf you're early retired, what do you do for health insurance?How do you handle health insurance when traveling as an early retiree?If you're planning to early retire in the future, how important is health insurance coverage to your decision of timing when to early retiree?Let me know by leaving a comment.Don't miss an episode, hit that subscribe button...If you liked this episode, be sure to subscribe so you don't miss any upcoming episodes!Apple PodcastsOvercastSpotifyStitcherI need your help, please leave a listener review :)If you liked this episode, would you please leave a quick review on Apple Podcasts? It'd mean the world to me and your review also helps others find my podcast, too!Related links:About Tracy WintersSchedule a private 1:1 consultation with meHYW private Facebook communityIntro/Outro: Old Bossa by Twin Musicom.

#92: Most FIRE stories are of men. A lot seem to be of ex-software engineers (on blogs anyway). It's rare to see profiles of early retired women, especially single women who retired early from ambitious careers.Also, most FIRE stories focus on strategies for things like accumulating enough assets to FIRE. Investment selection. Portfolio allocation. Safe withdrawal rates. Sequence risk.These are important topics for sure. I've covered many of them on HYW. But they are also very much about the mechanics.It's rare to hear how early retirees grapple with stuff like: loss of professional identity, building a new non-career identity, finding purpose, fulfillment, and community as an early retiree; or dating and companionship in early retirement.This week, I chat with Kim (last name withheld at her request) about her journey from MBA to corporate career to early retirement at 39 and her life and identity now 5 years post-FIRE. We discuss some of these rarely mentioned topics, as well as what it's been like so far in early retirement as a single woman.We talk about:Kim's career path before early retirementHow she came up with her FIRE numberHer numbers: earning/income trajectory from MBA graduation to early retirement, spending level during her career & now in retirementHer asset allocation + tactics she uses for managing, rebalancing, risk mitigation, and withdrawing from her portfolioFactors she considered in terms of spouse/family vs. early retirementAdvice on dating and companionship in early retirementWhat she learned about finding a new non-career identity, purpose, and fulfillment in early retirementHow Kim spends her days now & how she's found community as an early retireeHer advice for other young women who are interested in FIRECheck it out here:https://hackyourwealth.com/retire-early-women-business-career-professionalKnow any other interesting unmarried women who are pursuing or achieved FIRE? I'd be interested in potentially interviewing them for the podcast. Let me know by leaving a comment.Don't miss an episode, hit that subscribe button...If you liked this episode, be sure to subscribe so you don't miss any upcoming episodes!Apple PodcastsOvercastSpotifyStitcherI need your help, please leave a listener review :)If you liked this episode, would you please leave a quick review on Apple Podcasts? It'd mean the world to me and your review also helps others find my podcast, too!Related links:Schedule a private 1:1 consultation with meHYW private Facebook communityIntro/Outro: Old Bossa by Twin Musicom.

#91: It's no secret that many healthcare professionals earn lots of money. So, you might think it's relatively easy for them to achieve financial independence and retire early (or at least step back from demanding clinical hours).Aaaand….you'd be right about that!Sure, earning healthcare money is not a requirement for FIRE. But if you do, you certainly have more options…even if you also have large expenses (like kids).This week, I talk with Dr. G (anonymized, his request), a dentist with two kids in the midwest who built a $7 million nest egg before stepping back from clinical practice. He explains the actions he took to build his wealth…and what he's doing now.We discuss:His career path as a dentistNet worth after finishing dental schoolAge when he broke even and when he reached FIHow much he earned right out of dental school, when he broke even, when he reached FI, plus how much he earns passively nowSpending level over the years, plus how much he spends post-FIAsset allocation breakdownMain actions he took that had the biggest impact on net worthHis thought process on stepping back from clinical work with two young kids still in towFIRE tips for people with kidsCheck it out here:https://hackyourwealth.com/dentist-financial-independence-retire-earlyWhat type of FIRE profiles (career path, earning level, family/kid status, etc) do you want to hear more about? Let me know by leaving a comment.Don't miss an episode, hit that subscribe button...If you liked this episode, be sure to subscribe so you don't miss any upcoming episodes!Apple PodcastsOvercastSpotifyStitcherI need your help, please leave a listener review :)If you liked this episode, would you please leave a quick review on Apple Podcasts? It'd mean the world to me and your review also helps others find my podcast, too!Related links:Schedule a private 1:1 consultation with meHYW private Facebook communityIntro/Outro: Old Bossa by Twin Musicom.

#90: It's back to school season, and that means it's also the time of year for high school seniors to start agonizing over college applications.Applying to college is an anxiety-filled rite of passage for high school seniors, but it's often just as anxiety-inducing for parents who bang their heads on how to pay for it.That's because paying for college is, for many families, the biggest single expense they'll have for their child. It's also often the second biggest life expense a family will incur, right behind buying a home. Paying for college is like buying a Tesla Model Y and giving it away. Every year, for four years.So this week, I chat with my friend Ann Garcia about how to pay for college. She just wrote a new book on this topic, which we discuss in detail, along with important new updates to the federal financial aid process (FAFSA) + key things to know about 529 plan rules.We discuss:Why Ann decided to write this book now, what makes it differentThe mind-boggling cost of college today; forecasted cost in 15 yearsWhy college costs so much now, what's driven up the cost in recent decadesGoals that colleges are trying to accomplish with their financial aid awardsThings parents should do to prepare their child and finances for the cost of college from birth to high schoolWhy it's important for your child to do the official campus tour for colleges they're interested inRecent key changes and updates to the FAFSA processDifference between 529 savings plans vs. pre-paid tuition plans vs. Private College 529Mechanics of 529s: roll-over-ability, qualified expenses, taxes & penalties for non-qualified expenses, how scholarships are handled, changing beneficiariesCheck it out here:https://hackyourwealth.com/how-to-pay-for-collegeHave you been through (or will soon go through) the college financial aid process? What's been the most confusing or frustrating aspect? Let me know by leaving a comment.Don't miss an episode, hit that subscribe button...If you liked this episode, be sure to subscribe so you don't miss any upcoming episodes!Apple PodcastsSpotifyI need your help, please leave a listener review :)If you liked this episode, would you please leave a quick review on Apple Podcasts? It'd mean the world to me and your review also helps others find my podcast, too!Related links:Book: How to Pay for College: A complete financial plan for funding your child's educationOnline course: The College Financial Plan Masterclass - 20% discount exclusively for HYW subscribers (use code: HYW20)TheCollegeFinancialLady.com529 college savings plans: rules, tax benefits, & qualified expenses (HYW026)College financial aid tips and strategies, with Ann Garcia (HYW053)College student financial aid changes coming to the FAFSA application (HYW079)Schedule a private 1:1 consult with meHYW private FB communityIntro/Outro: Old Bossa by Twin Mus

#89: Summer is fast approaching, and that's traditionally when home-buying season ramps up.This week, I share insights on how to conduct due diligence when you're looking to buy a home. Whether you're buying a primary residence or investing in rental real estate, rigorous due diligence is critical to ensuring you get a good property at a reasonable price. In this episode, I explain my entire process for thoroughly analyzing a property before writing an offer.You learn:10 key things to look for when doing pre-tour due diligenceThe 4 big things to look for in disclosure packetsHow to evaluate the history of previous remodels, structural changes, or additions to the house done by prior ownersSpecial tips for buying a condo – how to analyze HOA records, financials, rules, and CC&RsMy 12-point checklist on what to look for when touring a home in personCheck it out here:https://hackyourwealth.com/real-estate-due-diligenceIf you've bought a home before, what are the most important due diligence items you look for? Let me know by leaving a comment.Don't miss an episode, hit that subscribe button...If you liked this episode, be sure to subscribe so you don't miss any upcoming episodes!Apple PodcastsOvercastSpotifyStitcherI need your help, please leave a listener review :)If you liked this episode, would you please leave a quick review on Apple Podcasts? It'd mean the world to me and your review also helps others find my podcast, too!Related links:Battle-tested home remodeling tips for saving serious money and getting the most from your contractorsHow to find and vet good home remodeling contractors like a bossHow to write an offer to purchase a house (that stands out and wins)How to do a residential property inspection step by step: What smart real estate investors look forHow to research real estate markets: The single best resource you needAvoiding capital gains tax on real estate: how the home sale exclusion worksThe True Benefit of Homeownership (why buying has paid off over renting, even in a million dollar market)Schedule a private 1:1 consultation with meHYW private Facebook communityIntro/Outro: Old Bossa by Twin Musicom.

#88: Have you maxed out your backdoor + mega backdoor Roth conversions yet?For high earners, direct contributions to a Roth IRA, and tax-deductible contributions to a traditional IRA, are limited by income thresholds.But ALL taxpayers – even high earners – can still invest money into a Roth via backdoor Roth conversion. And if your employer's 401k has the right plan features, you can turbo-charge your Roth conversions another 7x by doing the “mega backdoor” Roth conversion.What the heck do these mean? And how exactly do you do them?This week, I share what these concepts are, tips for how to execute them successfully, and what you need to know about your employer 401k to turbo-charge your Roth conversions.I explain:The difference between a backdoor Roth vs. mega backdoor RothHow to execute each one + tips to ensure no tax liability when you convertWhat plan features your employer 401k must have to do a mega backdoor RothWorkaround if your employer 401k does NOT allow in-plan Roth conversions, but DOES allow after-tax contributions (yes, you can still move that money into Roth)How recent proposed legislative changes would curtail the backdoor Roth strategy, and whether you need to worry about itA note about doing mega backdoor Roth conversions via Solo 401k.Check it out here:https://hackyourwealth.com/mega-backdoor-rothHave you done a backdoor or mega backdoor Roth conversion before? If you've decided not to, what dissuaded you? Let me know by leaving a comment.Don't miss an episode, hit that subscribe button...If you liked this episode, be sure to subscribe so you don't miss any upcoming episodes!Apple PodcastsOvercastSpotifyStitcherI need your help, please leave a listener review :)If you liked this episode, would you please leave a quick review on Apple Podcasts? It'd mean the world to me and your review also helps others find my podcast, too!Related links:Traditional vs. Roth? How to double-dip on the tax benefits of BOTHWhat is a Solo 401k? And Why It Beats All Other Retirement AccountsEverything you need to know about 401Ks (HYW003)IRAs, Roth IRAs, and how to get the tax benefits of BOTH (HYW004)Schedule a private 1:1 consultation with meHYW private Facebook communityIntro/Outro: Old Bossa by Twin Musicom.

#87: Remote work and digital nomadism have always been of particular interest to folks in the FIRE community.After the pandemic, remote work was suddenly thrust upon the entire knowledge workforce. And after two long pandemic years, the possibility that remote work for many professions will persist and become long-term viable options is tantalizingly close.What is the state of remote work right now? Where is the future of remote work headed? What jobs are most in-demand for remote work, and how much can you get paid for them?This week, I deep dive on these questions with Sharon Koifman, founder of DistantJob, a remote-only recruiting agency that helps companies find full-time remote employees around the world.We discuss:How Sharon became an advocate for remote work and got into remote recruitingHow the pandemic changed norms around remote workWhat types of jobs are most in-demand for remote work right nowWhat types of jobs still have not embraced remote workSkills and qualities employers look for when hiring remote employees (profile of an ideal candidate)Compensation: what remote employees can earn for certain roles (including pay range - min and max)How companies adjust compensation for remote employeesHow companies can promote strong, healthy remote work culturesCheck it out here:https://hackyourwealth.com/future-of-remote-workAnd now, I'm super curious…. Are you a remote worker or digital nomad? Trying to be? Wish to be? If so, what type of work do you do?If you work remotely for a company, was your compensation adjusted when you switched to remote?What's the biggest benefit vs. challenge you have experienced as a remote worker? How do you build (and keep) strong connections to people in your company/organization?Does being able to be remote change your FIRE plans, timeline, or philosophy at all?Let me know by leaving a comment!Don't miss an episode, hit that subscribe button...If you liked this episode, be sure to subscribe so you don't miss any upcoming episodes!Apple PodcastsOvercastSpotifyStitcherI need your help, please leave a listener review :)If you liked this episode, would you please leave a quick review on Apple Podcasts? It'd mean the world to me and your review also helps others find my podcast, too!Related links:DistantJobSurviving Remote Work: How to Thrive as a Leader and Entrepreneur in the Remote AgeSchedule a private 1:1 consultation with meHYW private Facebook communityIntro/Outro: Old Bossa by Twin Musicom.

#86: Pretty much everyone in the FIRE community has heard of the 4% rule.It is the starting safe withdrawal rate number for a 30-year retirement horizon that was proposed a few decades ago by retirement researchers.And it has attained near pop culture status in the FIRE community because it's such a simple mental shortcut to answer the question: “how much can I safely withdraw from my portfolio each year in retirement and have high confidence that I'll be financially secure for the rest of my life?”This is easily the most important question for ANY retiree, and especially early retirees. So, it's no wonder this topic is so intensely discussed in the FIRE community.More than a few early retirees and FIRE bloggers swear by the 4% rule and have plunged into their own retirement using this withdrawal rate expecting that it will carry them through for the rest of their lives.But when you ask the quants – the economists with the PhDs – there is broad agreement that the 4% rule no longer works most of the time.But why not?This week, I invited the renowned retirement economist Wade Pfau, PhD/CFA, who is Co-Director of the American College Center for Retirement Income, to share insight on why the 4% rule no longer works in today's environment. He suggests an alternate safe withdrawal rate number that may be better suited for today's retirees.We discuss:Why Dr. Pfau thinks the 4% rule is flawed today + how the world has changed since the 4% rule was first proposedPfau's recommended safe withdrawal rate number for the current environment (including assumed asset allocation)How Pfau thinks safe withdrawal rate planning will differ for early retireesPfau's thoughts on asset allocation in the current environment of rising interest rates, high inflation, and high asset valuationsWhat Pfau personally projects as his assumed real rate of return on stocks for his own portfolioHow annuities can play a crucial role in your retirement portfolio depending on your investor risk profile and desired stock allocationPfau's framework of 4 retirement styles + optimal asset allocation for eachCheck it out here:https://hackyourwealth.com/4-percent-ruleWhat do you think your safe withdrawal rate number is? And what asset allocation do you assume for that? Let me know by leaving a comment.Don't miss an episode, hit that subscribe button...If you liked this episode,  subscribe so you don't miss any upcoming episodes!Apple PodcastsOvercastI need your help, please leave a listener review :)If you liked this episode, would you leave a quick review on Apple Podcasts? It'd mean the world to me and your review also helps others find my podcast, too!Links mentioned in this episode:Wade PfauRetirement Planning GuidebookSafety-First Retirement Planning: An Integrated Approach for a Worry-Free RetirementHow Much Can I Spend in Retirement?Reverse Mortgages: How to Use Reverse Mortgages to Secure Your RetirementSchedule a 1:1 consultation with meHYW private Facebook community Intro/Outro: Old Bossa by Twin Musicom.

#85: Recently I've really started to notice the impact of inflation on daily spending. Have you?At first, it was just 1-2 things. Then it was a handful. Now it seems like everything is noticeably more expensive. (Assuming it's even in stock in the first place.)Gas. Groceries. Takeout. Toiletries. Utilities. Car maintenance. Healthcare/supplies. Pre-school. Appliances.Everything seems to cost more and you just can't buy as much with the same budget anymore.This got me wondering about how recent macroeconomic changes over the last 6 months might impact retirement safe withdrawal rates and asset allocations.The macro changes I'm referring to are: Inflation at a 40-year high. Stock valuations doubling since their pandemic lows. Interest rates that are scheduled to increase a minimum of 3 times this year.In these times, what should investors and retirees be doing to defend their portfolio values and retirement security?This week, I asked my friend Karsten Jeske (aka “Big ERN”) to help us make sense of all that is going on right now in terms of macro trends…and what it all means for safe withdrawal rates and asset allocation. We had a wide-ranging, nearly 2-hour(!) discussion full of insights and tips that you won't want to miss.We discuss:Major recent macroeconomic changes that (early) retirees may want to factor into their retirement planningWhat new safe withdrawal rate % retirees should consider right nowWhether investors should potentially update their asset allocation given current macro trendsWhether he believes asset prices are overvalued right nowAlternative assets (like cryptocurrencies) and their merits / concernsHow much cash he believes is advisable to hold right nowDo you plan to make changes to your asset allocation or safe withdrawal rate in light of recent macroeconomic changes? Let me know by leaving a comment!Don't miss an episode, hit that subscribe button...If you liked this episode,  subscribe so you don't miss any upcoming episodes!Apple PodcastsOvercastSpotifyI need your help, please leave a listener review :)If you liked this episode, would you leave a quick review on Apple Podcasts? It'd mean the world to me and your review also helps others find my podcast, too!Links mentioned in this episode:Karsten's Safe Withdrawal Rate SeriesKarsten's Google Sheet DIY Withdrawal Rate ToolboxKarsten's post on Preferred StocksThe shockingly un-simple math behind safe withdrawal rates (HYW035)How to use a bond tent to reduce sequence of returns risk (HYW068)Does the “yield shield” protect against sequence risk? (HYW069)Is rental real estate a safer type of “yield shield”? (HYW070)Schedule a 1:1 consult with meHYW Facebook community Intro/Outro: Old Bossa by Twin Musicom.

#84: Today's episode is about an important end-of-year planning topic: asset allocation and portfolio rebalancing.Many otherwise smart investors set their portfolio once, but then fail to rigorously monitor their asset allocation and rebalance regularly.Whether due to inertia or hassle, this inaction is costly. It results in lower returns and greater risk as your asset allocation drifts…bad for wealth-building.How do you set your target asset allocation optimally and rigorously? And how do you rebalance tax-efficiently?This week, I show you how to set your target asset allocation to match your risk profile and investment goals. I share how to track your asset allocation to see how much it has drifted from your target allocation. And I explain step-by-step how to tax-efficiently rebalance.If asset allocation and rebalancing feel like a mystery or chore, then don't miss today's episode. I'll show you how to do it systematically, efficiently, and rigorously…all in 1 hour or less per year.What you'll learn:Why it's prudent to sell your winning investments and rebalance toward your underdogsHow to create and define your target asset allocation starting from first principlesHow to determine your investment style and risk tolerance in an intellectually honest wayHow to track your current allocation and analyze drift from your targetHow to rebalance your portfolio tax-efficiently step-by-stepHow often you should rebalanceCheck it out here:https://hackyourwealth.com/asset-allocation-rebalance-portfolio-replayHow often do you rebalance your portfolio? Let me know by leaving a comment!Don't miss an episode, hit that subscribe button...If you liked this episode, be sure to subscribe so you don't miss any upcoming episodes!Apple PodcastsOvercastSpotifyStitcherI need your help, please leave a listener review :)If you liked this episode, would you please leave a quick review on Apple Podcasts? It'd mean the world to me and your review also helps others find my podcast, too!Links mentioned in this episode:Download my FREE spreadsheet to track your current vs. target asset allocationMy 4×4 FIRE framework for creating and protecting wealth (HYW002)Schedule a private 1:1 consultation with meHYW private Facebook community Intro/Outro: Old Bossa by Twin Musicom.

#83: You've worked hard all your life. At retirement, it's time to kick back and relax, right?Not so fast.You still have to get THROUGH retirement.That means knowing how to draw down your portfolio to:meet all your monthly cash flow needscushion against unexpected expensesminimize tax liabilityideally help your kids / grandkids, give to charity, or leave a legacyensure your retirement nut doesn't run out before you doThis is very challenging because you have to forecast things you simply can't know with certainty. Inflation rates. Market returns. Sequence risk. Tax rates. Your health condition and anticipated healthcare needs.So, how can retirees plan their retirement portfolio withdrawals to actually enjoy retirement and not worry about running out of money?This week, I sit down with Steve Parrish, Co-Director of the Center for Retirement Income at The American College of Financial Services, to talk about tax-efficient portfolio withdrawal strategies in retirement.We discuss:Key principles retirees should understand when deciding which assets to draw down and in what sequenceHow those principles change when you have alternate monthly income sources (like rental real estate, pension, etc)Why your wealth bracket determines what is the most tax-efficient sequence of portfolio withdrawalsHow soon-to-be and current retirees can protect themselves against sequence of returns riskWhen it makes sense to use legal tools like tax-free gifts, GRATs, etc, to reduce tax liability on retirement assetsWhy you might want to pay taxes now to do annual Roth conversions to ratchet down your IRA/401ks and the ticking tax time bomb attached to themPortfolio withdrawal advice for early retirees (FIRE)Check it out here:https://hackyourwealth.com/retirement-withdrawal-strategiesDo you worry about running out of money in retirement? If so, what is the biggest reason why – not saving enough, spending too fast, market tanks during retirement, something else? Let me know by leaving a comment.Don't miss an episode, hit that subscribe button...If you liked this episode, be sure to subscribe so you don't miss any upcoming episodes!Apple PodcastsOvercastSpotifyI need your help, please leave a listener review :)If you liked this episode, would you leave a quick review on Apple Podcasts? It'd mean the world to me and your review helps others find my podcast, too!Links mentioned in this episode:Steve ParrishThe shockingly un-simple math behind safe withdrawal rates (HYW035)How to FIRE with confidence, step by step (HYW060)How to use a bond tent to reduce sequence risk (HYW068)How long will your retirement savings last?Schedule a private 1:1 consultationHYW Facebook community Intro/Outro: Old Bossa by Twin Musicom.

#82: Are annuities a good investment for retirement?With $250 billion in sales each year, and $2.5 trillion in retirement annuity assets under contract, annuities comprise a huge slice of US retirement assets.Understanding annuities – whether annuities are right for you, and how annuities fit into your retirement strategy – can get complicated given all the annuity options out there and the extreme uncertainty in today's markets.So this week, I sat down with Stan Haithcock, aka “Stan The Annuity Man,” to deep dive on annuities. We chat about how annuities work, why annuities are not investments (in the portfolio sense), and why there is no such thing as “best annuities.”We discuss:What annuities are and what purpose they serveThe different types of annuity options (immediate annuity, deferred annuity, fixed annuity, variable annuity, indexed annuity, multi-year guaranteed annuity, life annuity)How annuities account for inflationThe mechanics of how to buy an annuityHow insurance companies that sell annuities make moneyThe different type of annuity fees you can expect, and typical all-in costs for different annuity typesHow to vet the insurance companies that sell annuitiesHow to vet an agent and questions to ask before buying an annuity from themHow agents who sell annuities are compensatedAnnuity taxes and the tax profile of annuitiesBasic protections your annuity gets if the insurance company you bought it from goes bankruptWho annuities are best suited for, and whether annuities are a good idea for early retirees (FIRE)Check it out here:https://hackyourwealth.com/annuitiesHave you purchased any annuities before, either for yourself or a family member? What kind of annuity did you buy, and why? Let me know by leaving a comment.Don't miss an episode, hit that subscribe button...If you liked this episode, be sure to subscribe so you don't miss any upcoming episodes!Apple PodcastsOvercastSpotifyStitcherI need your help, please leave a listener review :)If you liked this episode, would you please leave a quick review on Apple Podcasts? It'd mean the world to me and your review also helps others find my podcast, too!Links mentioned in this episode:The Annuity ManNational Organization of Life & Health Insurance Guaranty AssociationsSocial Security: How it works and optimal claiming strategies (HYW050)How Medicare works: eligibility, enrollment, cost, and coverage options (HYW048)How Social Security Works: The Ultimate Guide For LaypersonsRetirement withdrawal calculator: How long will your savings last in retirement?Schedule a private 1:1 consultation with meHYW private Facebook community Intro/Outro: Old Bossa by Twin Musicom.

#81: With the market rallying like crazy this past year, you might have significant capital gains on stocks right now.Now might be a good time for some of you investors to harvest some capital gains. Maybe you're looking to buy a house. Or maybe you just want to rebalance your investments.But when you sell stock, you pay taxes on the sale.And capital gains taxes can get complex because the effective tax rate you pay when you sell stock depends on whether there are long-term vs. short-term capital gains, whether there are any long-term vs. short-term losses, what your marginal tax rate is, and even whether you are required to pay the Medicare Surcharge Tax.That's why this week I invited CFA Scott Stratton to explain the intricacies of how capital gains taxes work. We discuss key rules and strategies you need to know to do thoughtful capital gains tax planning. If you want to learn how to minimize capital gains taxes, then don't miss this episode.You'll learn:What types of assets capital gains taxes apply toDifference between short-term vs. long-term capital gains tax treatmentHow capital gains and losses work in tandem come tax filing timeHow to harvest capital losses and harvest capital gainsCurrent proposed legislative changes to capital gains tax ratesWhat investors may want to consider doing now before potential changes take effectCheck it out here:https://hackyourwealth.com/capital-gains-tax-on-stocksWhat other tax planning questions do you have about capital gains taxes? Let me know by leaving a comment.Don't miss an episode, hit that subscribe button...If you liked this episode, be sure to subscribe so you don't miss any upcoming episodes!Apple PodcastsOvercastSpotifyStitcherI need your help, please leave a listener review :)If you liked this episode, would you please leave a quick review on Apple Podcasts? It'd mean the world to me and your review also helps others find my podcast, too!Links mentioned in this episode:Good Life Wealth ManagementTax Loss Harvesting: Rules and Strategies with Bob Dockendorff (HYW022)How to take a year off, earn 6 figures, harvest capital gains, do Roth conversions…and pay zero taxes on it allHow to earn 6 figures and legally pay zero taxes (updated for 2020) (HYW021)Avoiding capital gains tax on real estate: how the home sale exclusion worksHow the Home Sale Capital Gains Tax Exclusion Works (HYW033)Schedule a private 1:1 consultation with meHYW private Facebook community Intro/Outro: Old Bossa by Twin Musicom.

#80: Teaching kids about money isn't easy, but it's crucial if you want to boot them off your payroll after they graduate from school.But while financial literacy is good, helping your kids build the mindset and momentum to achieve financial independence is even better.It requires that they internalize (and value) aggressive saving, investing, and compounding…not just living within their means.That's why I was so excited to chat this week with Doug Nordman and Carol Pittner, father and daughter co-authors of a new book on how to teach next-generation financial independence.We discuss:Why it's important to let kids make their own financial choices (and mistakes) when the stakes are lowWhy letting your kids buy “One Special Thing” per shopping trip is an effective teaching strategyWhy you might want to pay your kids for jobs, but not chores…and the difference between the twoWhy it might not be a good idea to pay your kids for getting good grades, and what you can do insteadWhy “profit sharing” is an especially powerful strategy to teach kids about savings and frugalityHow to create a “kid 401k” to teach your kid lasting lessons about compounding and long-term investingHow to incentivize your kid to contribute to a Roth IRA early onHow to handle the question of “how rich are we?”Check it out here:https://hackyourwealth.com/teaching-kids-about-money-financial-independenceWhat strategies do you use to teach your kids about saving, investing, and compounding? How are you helping them learn about financial independence, if at all? Let me know by leaving a comment.Don't miss an episode, hit that subscribe button...If you liked this episode, be sure to subscribe so you don't miss any upcoming episodes!Apple PodcastsOvercastSpotifyStitcherI need your help, please leave a listener review :)If you liked this episode, would you please leave a quick review on Apple Podcasts? It'd mean the world to me and your review also helps others find my podcast, too!Links mentioned in this episode:Raising Your Money-Savvy Family For Next Generation Financial IndependenceThe Military GuidechildFIREFinancial literacy for kids: how to teach your kids about money (HYW077)9 Crucial Money Lessons Your Kids Must Learn to Succeed as Adults (HYW027)How to financially prepare for starting a family with Kevin Mahoney (HYW038)The best parenting guidance I've learned for raising successful childrenSchedule a private 1:1 consultation with meHYW private Facebook community Intro/Outro: Old Bossa by Twin Musicom.

#79: This one's for you parents who have kids in college or soon going to college…In the COVID relief stimulus bill that passed at the end of 2020, there was a big chunk about federal student financial aid.New rules are bringing significant changes to college financial aid. This week, I deep dive with my friend Ann Garcia, aka The College Financial Lady, on what these changes are and how they will impact you and your family.We discuss:Overview of the federal student financial aid application process, including key datesImportant changes coming to the federal financial aid process: for the FAFSA application, families with multiple college-aged kids, grandparent 529 plans, divorced parents, and moreTimeline and phasing of these changes coming in 2021, 2022, 2023 and beyondCheck it out here:https://hackyourwealth.com/fafsa-federal-student-financial-aid-changesWill you be applying for college financial aid over the next few years? What one thing brings you the biggest worry when it comes to college financial aid? Let me know by leaving a comment.Don't miss an episode, hit that subscribe button...If you liked this episode, be sure to subscribe so you don't miss any upcoming episodes!Apple PodcastsOvercastSpotifyStitcherI need your help, please leave a listener review :)If you liked this episode, would you please leave a quick review on Apple Podcasts? It'd mean the world to me and your review also helps others find my podcast, too!Links mentioned in this episode:The College Financial LadyCollege financial aid tips and strategies, with Ann Garcia (HYW053)529 college savings plans: rules, tax benefits, & qualified expenses (HYW026)College financial aid strategies to optimize your assets, income & EFC (HYW025)Schedule a private 1:1 consultation with meHYW private Facebook community Intro/Outro: Old Bossa by Twin Musicom.

#78: For this episode, I polled other influencers in the personal finance community to ask for their best tip on teaching money lessons to kids.I had four different personal finance influencers weigh in – a range of bloggers, podcasters, authors, and community admins. All of them are parents themselves.I asked each person to answer one simple question:“When it comes to teaching your kids about money, what single method or strategy have you personally found to be most effective?”Check out their collective tips here:https://hackyourwealth.com/money-lessons-for-kids-tips-from-personal-finance-influencersWhat strategy have YOU found to be most effective when it comes to teaching your kids about money? Let me know by leaving a comment. Don't miss an episode, hit that subscribe button...If you liked this episode, be sure to subscribe so you don't miss any upcoming episodes!Apple PodcastsOvercastSpotifyStitcherI need your help, please leave a listener review :)If you liked this episode, would you please leave a quick review on Apple Podcasts? It'd mean the world to me and your review also helps others find my podcast, too!Links mentioned in this episode:Couple Money Podcast, Thriving Families FB groupRaising Your Money-Savvy Family For Next Generation Financial IndependenceKateHorrell.comPersonal Finance for U.S. Military Service Members and Families FB groupHer Dinero Matters podcastFinancial literacy for kids: how to teach your kids about money (HYW077)9 Crucial Money Lessons Your Kids Must Learn to Succeed as Adults (HYW027)How to financially prepare for starting a family with Kevin Mahoney (HYW038)Hey, rich people. Wealth management includes telling your kids how rich you are.The best parenting guidance I've learned for raising successful childrenHow to motivate your kid to win the national spelling bee (and excel in life)Schedule a private 1:1 consultation with meHYW private Facebook community Intro/Outro: Old Bossa by Twin Musicom.

#77: Teaching financial literacy for kids may seem like a tall order…when considering that financial literacy even for adults is a national deficiency.But teaching kids about money is crucial if you want your kids to grow up financially responsible and independent.As a parent, you will have a strong vested interest in it, because if you fail at it you'll eventually pay the consequences (literally), e.g., if your adult kid can't support themselves and move out of the house.And early retirement? You can probably kiss that goodbye if your kid is financially reckless.So, instilling good financial education for your kids is a wise investment…maybe even the wisest investment.This week, I spoke with Robin Taub, author of the book “The Wisest Investment,” about how to instill financial literacy for children. We discuss strategies, role modeling, and techniques for teaching personal finance and money lessons to your kids.What you'll learn:Why teaching kids about money is hardWhat financially well-educated kids have in commonThe right age to start teaching kids about money in earnestThe crucial money lessons kids at each maturity level should know to have healthy skills, habits, and mindsets about moneyRobin's core framework for teaching kids about moneyCommon mistakes parents make when teaching their kids about money, and the most effective role modeling parents can do to successfully teach their kids about moneyHow to get kids to become self-motivated to learn about money, saving, investing, and budgetingHow parents can create teachable moments in daily life and turn them into money lessons for their kidsHow to answer awkward questions like “how rich are we” and “how much money does our family make”How parents can help teach their kids to embrace impulse control and delayed gratification when it comes to moneyGuidelines for paying kids an allowance or paying kids to do choresHow to teach kids about budgeting (and when it's age appropriate)For affluent families: how to make sure your kids don't take money for granted or become spoiled entitled bratsWhat methods have you found to be effective when it comes to teaching your kids about money? If your kids are self-motivated to learn about personal finance – earning, budgeting, saving, investing – how did you get them to be self-motivated? Let me know by leaving a comment.Don't miss an episode, hit that subscribe button...If you liked this episode, be sure to subscribe so you don't miss any upcoming episodes!Apple PodcastsOvercastSpotifyI need your help, please leave a listener review :)If you liked this episode, would you please leave a quick review on Apple Podcasts? It'd mean the world to me and your review also helps others find my podcast, too!Related links:The Wisest Investment: Teaching Your Kids to Be Responsible, Independent and Money-Smart for LifeRobin Taub9 Crucial Money Lessons Your Kids Must Learn to Succeed as Adults (HYW027)Schedule a private 1:1 consultation with meHYW private Facebook communityIntro/Outro: Old Bossa by Twin Musicom.

#76: Retiring early to travel the world is a common goal for FIRE aspirants.But full-time travel can lose appeal quickly. Churches and temples quickly start to look the same. Gardens and palaces quickly look the same.When you're responsible for creating all the structure to your day – every day for weeks and months on end – it gets exhausting and can feel purposeless.But what if you could design early retirement travel around language learning?By enrolling in language immersion courses at local language schools in countries you travel to, you not only learn how to communicate conversationally with locals. You also get structured and even vibrant exposure to local culture, food, people, and activities because being situated in a school or university environment creates that exposure and structure for you naturally.This week, I invited Ingrid, a software engineer turned early retiree and successful travel blogger, to share about her early retirement experience pursuing language learning through travel immersion courses. Making language learning the focus of early retirement has brought joy and purpose and structure to her travel experiences.We discuss:How Ingrid came up with and built strong confidence in her FIRE numberHer asset allocation and withdrawal rateHer blog's revenue contribution (and what helped her blog get traction)How Ingrid plans travel around language immersion coursesHow she meets and connects with locals when she travels, plus her advice for solo female travelersHow she handles health insurance and healthcare costs as an early retiree and when she's travelingHow she believes one's emotional well being and personality change in early retirementHow she contemplated family and children alongside her early retirement plan, why she decided against having a family, and her thoughts on loneliness, dating, and companionship as an early retireeWhat Ingrid would have done differently if she could do it over againCheck it out here:https://hackyourwealth.com/language-learning-courses-retirement-travel-immersionHave you ever studied abroad or taken a language immersion course in another country? What do you think about the notion of pursuing language learning through travel immersion courses in early retirement? Let me know by leaving a comment!Don't miss an episode, hit that subscribe button...If you liked this episode, subscribe so you don't miss any upcoming episodes!Apple PodcastsOvercastSpotifyI need your help, please leave a listener review :)If you liked this episode, would you please leave a review on Apple Podcasts? It'd mean the world to me and your review also helps others find my podcast, too!Links mentioned in this episode:Second-Half TravelsFirecalcCouchsurfingSquaremouthNomad CruiseRemote YearWiFi TribeSchedule a 1:1 consult with meHYW FB communityIntro/Outro: Old Bossa by Twin Musicom.

#75: Real estate investing might seem like something only wealthy people can do.It's expensive, down payments can be high, and you may feel you don't have enough income to afford it.Maybe you think: “I can't even afford a house to LIVE in…how would I afford a house to invest in?”But the plain truth is: there are lots of average Joes who do it…and who build a lot of wealth from it!Today's podcast guest is one such (inspiring) example.John and Rosalina Steiner reached out to me (after following the podcast!) to share their real estate investing story. I found it compelling and wanted to share their insights and wisdom with you, too. Hope you enjoy listening to their story as much as I did!We chat about:How and why the Steiners started investing in real estate in the first placeTheir 25-door real estate portfolio breakdown – what type of units, where they're located, how many have mortgagesHow they financed the down payments and loans for each propertyWhy they chose the neighborhoods they invest inWhy they self-manage, and their best tips for managing tenants effectivelyTheir views on Section 8 and how they manage Section 8 tenantsWhy they never plan to stop investing…even though they're 65!Check it out here:https://hackyourwealth.com/real-estate-investing-with-middle-class-incomeDo you wish to invest in real estate but feel like you don't know how to get started? What's the biggest factor you think holding you back? Let me know by leaving a comment.Don't miss an episode, hit that subscribe button...If you liked this episode, be sure to subscribe so you don't miss any upcoming episodes!Apple PodcastsOvercastSpotifyStitcherI need your help, please leave a listener review :)If you liked this episode, would you please leave a quick review on Apple Podcasts? It'd mean the world to me and your review also helps others find my podcast, too!Links mentioned in this episode:John & Rosalina SteinerMultifamily real estate investing: how to build a $175M portfolio in 7 years with Andrew Campbell (HYW029)Schedule a private 1:1 consultation with meHYW private Facebook community Intro/Outro: Old Bossa by Twin Musicom.

#74: This week, I chat with Caroline Ceniza-Levine, a career coach now early retired, whose own spouse wasn't on board with early retirement for many years before she finally convinced him to get on the FIRE train.We talk about tips and advice for how to convince your spouse about early retirement – and all it entails...We discuss:Caroline's own path to FIRE – from music, to strategy consulting, to corporate, to coaching, to FIREHer spouse's main concerns when it came to early retirementHow she got her spouse on board, what she would have done differently, and her advice for others who are struggling to convince their partner about early retirementPlus: how Caroline handles healthcare / insurance as an early (pre-Medicare) retiree, her passive rental real estate portfolio breakdown and how she manages her rentals remotelyCheck it out here:https://hackyourwealth.com/retire-early-with-spouse-workingHave you ever been at odds with your spouse about early retirement? What were their main concerns? Were you able to change their mind – how? Let me know by leaving a comment.Don't miss an episode, hit that subscribe button...If you liked this episode, be sure to subscribe so you don't miss any upcoming episodes!Apple PodcastsOvercastSpotifyStitcherI need your help, please leave a listener review :)If you liked this episode, would you please leave a quick review on Apple Podcasts? It'd mean the world to me and your review also helps others find my podcast, too!Links mentioned in this episode:Costa Rica FIREMoney issues in marriage: why spouses fight about money, how to fight with empathy, and how to convince your spouse to FIRE (HYW065)Schedule a private 1:1 consultation with meHYW private Facebook community   Intro/Outro: Old Bossa by Twin Musicom.

#73: One big reason the tech industry attracts a lot of talent: you get partly compensated in stock, and if you're early enough at a company that IPOs, your stock options or RSUs can make you a millionaire multiple times over when the company goes public.Google created >1000 millionaires at IPO. Facebook too. Microsoft has created >10k millionaires. Amazon probably even more.But with stock compensation, your taxes can quickly get complicated. You need thoughtful tax planning to make sure you don't pay more in taxes than needed. As with other types of income, what matters isn't what you earn – it's what you keep.So this week, I spoke with Shane Mason, whose CPA firm specializes in advising entrepreneurs and tech workers, to share tips and strategies on stock option and RSU tax planning.We discuss:The different types of stock-based compensation and tax regime applicable to eachDeep dive on Incentive Stock Options + AMT + AMT “refund” rulesHow an 83(b) election works, and pros/cons of doing itKey tax planning strategies applicable to stock compensation (e.g. timing strategies, optimizing tax buckets)Check it out here:https://hackyourwealth.com/stock-option-rsu-tax-planningDo you earn stock-based compensation? What tax planning best practices have you followed? What do you want to know more about when it comes to stock tax planning? Let me know by leaving a comment.Don't miss an episode, hit that subscribe button...If you liked this episode, be sure to subscribe so you don't miss any upcoming episodes!Apple PodcastsOvercastSpotifyStitcherI need your help, please leave a listener review :)If you liked this episode, would you please leave a quick review on Apple Podcasts? It'd mean the world to me and your review also helps others find my podcast, too!Links mentioned in this episode:Brooklyn FISchedule a private 1:1 consultation with meHYW private Facebook community Intro/Outro: Old Bossa by Twin Musicom.

#72: This week, I invited Bill Exeter to teach us about 1031 exchanges. He is the CEO of Exeter 1031 Exchange Services and has been doing 1031s for nearly four decades.You might know at a high level that a 1031 exchange means deferring real estate capital gains taxes. But the details are important to avoid dumb mistakes that will disqualify you.We discuss:Different types of 1031 exchangesKey criteria and deadlines + step-by-step process for executing a 1031How to optimize timing your buy/sell transactionsLike-kind replacement property rulesDomestic vs. foreign property exchangesWhat constitutes “Qualified Use” + holding period requirementsState tax consequencesWhy investors can’t do 1031s themselvesThe role of a Qualified Intermediary, how to vet one, and how much they costTax impact of converting a 1031 property into owner-occupied housing, and vice versaCommon mistakes that disqualify you from a 1031Proposed Biden administration changes to 1031s: likelihood of passage + actions you can take now to mitigate adverse tax impactCheck it out here:https://hackyourwealth.com/1031-exchangeEver done a 1031 transaction? What was your experience? Anything you would do differently next time? Let me know by leaving a comment.Don't miss an episode, hit that subscribe button...If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!Apple PodcastsOvercastSpotifyStitcherI need your help, please leave a listener review :)If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!Links mentioned in this episode:Exeter Group1031taxreform.comHow to avoid capital gains taxes when selling your houseHow the Home Sale Capital Gains Tax Exclusion Works (HYW033)Schedule a private 1:1 consultation with meHYW private Facebook community   Intro/Outro: Old Bossa by Twin Musicom.

#71: Tax deed auctions provide an opportunity to buy tax-delinquent properties at a discount, wipe away existing liens and mortgages, and earn sizable profits in the process.This week, I invited my friend Phil Kessler back to the podcast to teach us how this unique type of real estate investing works.If you’ve ever wondered how tax deed auctions work, how to win them, and how to due diligence this type of real estate, then don’t miss this insight-packed episode.What you’ll learn:How tax deed investing differs from tax lien investingHow tax deed auctions work, how they differ from other foreclosure auctionsThe most important things to due diligence when it comes to tax deed properties, and how to due diligence themThe most helpful online tools for property due diligenceHow to buy tax delinquent properties BEFORE they go to auction (and avoid competing against scores of other bidders)How redemption periods work, and which states have themHow a quiet title lawsuit works, how much it costs, and what happens if a title dispute arisesHow tax deed auctions affect existing mortgages and liens, and how to verify the rules in your stateCheck it out here:https://hackyourwealth.com/tax-deed-investingHave you ever bid in a real estate auction? What was your experience? What other questions do you have about tax deed investing that weren’t covered here? Let me know by leaving a comment.Don't miss an episode, hit that subscribe button...If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!Apple PodcastsOvercastSpotifyStitcherI need your help, please leave a listener review :)If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!Links mentioned in this episode:propertyonion.comThe Deed FeedVelocity REOsRealAuction.comGrant Street GroupCivicSourceAAR AuctionGovEaseHow tax lien investing works and how to buy tax lien certificates (HYW066)Real estate investing through house auctions and hard money lending with Ethan Gao (HYW032)Schedule a private 1:1 consultation with meHYW private Facebook community  Intro/Outro: Old Bossa by Twin Musicom.

#70: Last time, we talked about the pros and cons of the “yield shield” and the impassioned views on both sides of that debate.But what if you sidestep that entirely and generate your dividend yield through rental real estate instead?Unlike stock dividends, which can be cut by company management, rents are arguably way more stable. Plus, real estate can be leveraged with a mortgage to juice a higher capital return.Separately, regardless of which strategy you use, how should retirees think about the “crossover” point beyond which sequence risk effectively disappears?This week, in the final part of our 3-part series on asset allocation, we talk again with Karsten Jeske, CFA, about both these topics.We discuss:How rental real estate can change your optimal asset allocationWhether a bond tent strategy is still relevant if you have rental real estateHow to analyze the sequence risk crossover point after which you are guaranteed to outlive your savingsHow to visualize the relationship between “how much nest egg is left” vs. “how much retirement is left,” and how to know when you’re really “out of the woods”Check it out here:https://hackyourwealth.com/sequence-risk-analysisDo you think rental real estate is a more effective “yield shield” vs. dividend stocks? Would you change your asset allocation with rental real estate? How will you know when you’ve crossed the sequence risk “crossover” point?Let me know by leaving a comment!Don't miss an episode, hit that subscribe button...If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!Apple PodcastsOvercastSpotifyStitcherI need your help, please leave a listener review :)If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!Links mentioned in this episode:ERN's "When Can We Stop Worrying about Sequence Risk?"Asset allocation: Does the “yield shield” really protect against sequence of returns risk? (HYW069)Asset allocation: How to use a bond tent to reduce sequence of returns risk (HYW068)The shockingly un-simple math behind retirement safe withdrawal rates (Part 1) (HYW035)The shockingly un-simple math behind retirement safe withdrawal rates (Part 2) (HYW036)Schedule a private 1:1 consultation with meHYW private Facebook community  Intro/Outro: Old Bossa by Twin Musicom.

#69: Last time we talked about using a “bond tent” strategy to reduce sequence risk in the years just before and just after retirement.In FIRE communities, an alternate strategy that has become popular is the “yield shield.”A yield shield strategy involves holding primarily investments that pay a high dividend yield.The theory is: if the investment pays a dividend yield of 3-4% that might be all you need to cover your safe withdrawal rate. If you don’t ever have to touch the principal, sequence risk might disappear entirely.But is it really that simple?This week, in part 2 of our 3-part series on asset allocation, we continue our discussion with Karsten Jeske, CFA, about the pros and cons of a yield shield strategy. We start by wrapping up our glide path discussion from last week, then dive into a critique of the yield shield.We discuss:How early retirees with kids should plan for key expense milestones during retirement that traditional retirees have already dealt with (college, buying a home, etc)Pros and cons of a yield shield strategyWhether investing in dividend kings or dividend aristocrats helps to address the consThe importance of looking at total return when analyzing the yield shield, and why a high dividend doesn’t translate into higher total returnReasons why the yield shield can fall short (and examples where it did)The right way to define success of a yield shield strategyWhy Karsten doesn’t fundamentally believe the yield shield does better than a plain vanilla stock indexCheck it out here:https://hackyourwealth.com/yield-shield-critiqueThis yield shield critique has been very controversial in FIRE communities. Are you persuaded by it? Or do you believe the yield shield performs better? Why or why not? Let me know by leaving a comment.Don't miss an episode, hit that subscribe button...If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!Apple PodcastsOvercastSpotifyStitcherI need your help, please leave a listener review :)If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!Links mentioned in this episode:Dividend ETFs: VYM, NOBL, SDY, DVYERN's Yield Shield critiqueERN's critique of the dividends-only approachAsset allocation: How to use a bond tent to reduce sequence of returns risk (HYW068)The shockingly un-simple math behind retirement safe withdrawal rates (Part 1) (HYW035)The shockingly un-simple math behind retirement safe withdrawal rates (Part 2) (HYW036)Schedule a private 1:1 consultation with meHYW private Facebook community  Intro/Outro: Old Bossa by Twin Musicom.

#68: This week, in part 1 of a 3-part series on asset allocation, I talk with Karsten Jeske, CFA, about how to implement bond/equity glide paths, both leading into retirement and in the initial years after retirement.Getting your asset allocation right, and shrewdly changing its composition in the years just before and just after retirement is one of the most impactful things you can do to offset sequence of returns risk.If you want to understand how to do this effectively, don’t miss today’s episode!We discuss:The intuition behind bond tents and equity glide pathsPros and cons of a bond tent strategy (what you gain, what you lose)How to determine the optimal % peak allocation of bondsHow long you should optimally stretch each glide path over (and why each side probably should be different durations)When is a longer vs. shorter glide path better in terms of returns and riskWhen is a bond tent NOT worth it and you should just stick with 100% equitiesCheck it out here:https://hackyourwealth.com/asset-allocationWhat do you think about the bond tent strategy? Let me know by leaving a comment.Don't miss an episode, hit that subscribe button...If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!Apple PodcastsOvercastSpotifyStitcherI need your help, please leave a listener review :)If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!Links mentioned in this episode:ERN's cashflow modeling spreadsheetERN's posts on glidepaths: part 1, part 2The shockingly un-simple math behind retirement safe withdrawal rates (Part 1) (HYW035)The shockingly un-simple math behind retirement safe withdrawal rates (Part 2) (HYW036)Schedule a private 1:1 consultation with meHYW private Facebook community  Intro/Outro: Old Bossa by Twin Musicom.

#67: Given how big of a shock the events of 2020 were for just about everyone on the planet, what changes to the tax rules happened as a result?This week I invited Katelynn Minott, CPA and managing partner at Bright!Tax, to share key tax filing updates to be aware of when you file your tax returns this year.What you’ll learn:Tax treatment of CARES Act stimulus checksHealthcare related tax updates (e.g., qualified medical expense deductions)Updates to retirement plan rules (e.g., contributions, withdrawals, inherited IRAs)Tips for reducing investment income taxesEducation related changes (e.g., student loan payments)Charitable donation changesCommonly missed business deductions for self-employed / sole proprietorsTax issues and updates applicable to remote workers (e.g., state tax residency rules, foreign earned income exclusion for expats)Check it out here:https://hackyourwealth.com/2020-tax-filingWhat other 2020 tax filing questions do you have? Let me know by leaving a comment and, if there are enough, I’ll send them to Katelynn for feedback!Don't miss an episode, hit that subscribe button...If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!Apple PodcastsOvercastSpotifyStitcherI need your help, please leave a listener review :)If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!Links mentioned in this episode:Bright!TaxSchedule a private 1:1 consultation with meHYW private Facebook communityIntro/Outro: Old Bossa by Twin Musicom.

#66: Investing in tax liens may sound scary and complicated. But as you’ll see from today’s podcast interview, with a little bit of research upfront, it can be as easy as buying toilet paper on Amazon. And the capital required to invest can be as little as a couple hundred bucks, making it a low-risk way (compared to buy-and-hold real estate) to try a new investing strategy.This week, I deep dive on tax lien investing with Phil Kessler, a prolific tax lien investor who has extensively researched the tax lien investing laws of multiple states. He also creates a lot of educational content about tax lien and tax deed investing online.We discuss:How tax lien investing works + how to make money from itDifferences between tax lien vs. tax deed investingHow tax lien interest rates are set + realistic rates you can expectWhat makes an ideal tax lien investmentDue diligence checklist for analyzing tax lien deals (and how it differs from typical real estate investing due diligence)Tips and tricks for evaluating physical property condition, environmental risks, etc, when you can’t access the houseHow tax lien auctions work + winning bid strategiesHow tax lien investment funds work + tradeoffs of investing in a fundCheck it out here:https://hackyourwealth.com/tax-lien-investingHave you ever invested in tax liens? What’s been your experience? What other questions do you have about it? Let me know by leaving a comment.Don't miss an episode, hit that subscribe button...If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!Apple PodcastsOvercastSpotifyStitcherI need your help, please leave a listener review :)If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!Links mentioned in this episode: Nationwide Environmental Title Research (directory of public records websites)Velocity REOs (drive to any property, take 10-15 photos for you)National Association of Counties (find tax sale info on county treasurer site)National Tax Lien AssociationRealAuction.comGrant Street Grouppropertyonion.comSchedule a private 1:1 consultation with meHYW private Facebook community Intro/Outro: Old Bossa by Twin Musicom.

#65: Last time we talked about money issues when dating.But dating isn’t the end game (for most).As the schoolyard song goes: “First comes love, then comes marriage…”…And money matters, if anything, get amplified once you’re married.It’s why money problems are the top or second leading cause of failed marriages (read: divorce) depending on which study you read…and it’s always a contributing factor even if it isn’t the straw that breaks the camel’s back.So this week, I continue my conversation with Megan McCoy and Ed Coambs, two leading marriage therapists who specialize in financial therapy and conflict, to discuss how money matters get more complex after marriage…and what spouses can do about it to preserve and strengthen their relationship.We discuss:The most common reasons and triggers why couples fight about moneyWhether keeping separate money accounts is a good ideaHow to fight about money productively, with empathy, to keep your relationship healthy and even strengthen itWhere spouses should learn to compromise when it comes to money and financesIntentional money rituals that spouses can do to keep their relationship healthyHow to get your spouse on board with early retirement (and the financial sacrifices required to do it)Check it out here:https://hackyourwealth.com/money-marriageWhat is the most important thing young married couples should know about handling money issues together? Do you think keeping separate money accounts is a good idea? What’s your best advice for fighting about money with your spouse, with empathy? Let me know by leaving a comment.Don't miss an episode, hit that subscribe button...If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!Apple PodcastsOvercastSpotifyStitcherI need your help, please leave a listener review :)If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!Links mentioned in this episode:Ed Coambs’ Healthy Love & MoneyMegan McCoy, Ph.D., LMFTMoney Scripts article; Klontz Money Script InventoryPrepare Enrich workbook for couplesDew, J., & Dakin, J. (2011). Financial Disagreements and Marital Conflict Tactics. Journal of Financial Therapy, 2 (1) 7Love Sense: The Revolutionary New Science of Romantic RelationshipsHealing Your Attachment Wounds: How to Create Deep and Lasting Intimate RelationshipsHYW private Facebook community Intro/Outro: Old Bossa by Twin Musicom.

#64: How do you have difficult conversations about money when you’re dating? What words should you use? What do you do if the conversations go south?This week, I invited Megan McCoy and Ed Coambs, two leading couples therapists who specialize in financial therapy and conflict, to share insights about how to talk about money matters when you’re dating.We discuss:Questions to ask (and behaviors to observe) early in a relationship to learn your partner’s financial valuesTips for asking sensitive money-related questions that don’t rub your partner the wrong wayHow to handle it if your partner does get defensive or reacts the wrong wayTips for attracting a partner who shares your financial valuesWhat to do if you’ve met “the one” but have totally different mindsets and behaviors about moneyCheck it out here:https://hackyourwealth.com/money-datingHow have you approached talking about money when dating? What tips and best practices have worked for you? What advice do you have for other couples? Let me know by leaving a comment.Don't miss an episode, hit that subscribe button...If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!Apple PodcastsOvercastSpotifyStitcherI need your help, please leave a listener review :)If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!Links mentioned in this episode:Ed Coambs’ Healthy Love & MoneyEd Coambs’ Charlotte Couples CounselingMegan McCoy, Ph.D., LMFTMoney Scripts article; Klontz Money Script InventoryBrad Klontz’s How Clients’ Money Scripts Predict Their Financial BehaviorsPrepare Enrich workbook for couplesDew, J., & Dakin, J. (2011). Financial Disagreements and Marital Conflict Tactics. Journal of Financial Therapy, 2 (1) 7Love Sense: The Revolutionary New Science of Romantic RelationshipsHealing Your Attachment Wounds: How to Create Deep and Lasting Intimate RelationshipsHYW private Facebook community Intro/Outro: Old Bossa by Twin Musicom.

#63: Last time, we talked about general asset location principles, plus best practices for major asset classes like stocks, bonds, and real estate.But what about non-traditional asset classes?Also, if you’re planning to early retire, should your asset location considerations change at all…given that you generally cannot touch your tax-advantaged accounts until you’re nearly 60?This week, we continue our discussion with Jonathan Duong, CFA, about both these topics as they relate to tax-efficient asset location.We discuss:Commodities (gold, oil)CurrenciesIlliquid investments like LPs, private equity, private loans, etcSpeculative holdings like Bitcoin, art, collectiblesHow asset location considerations might change for early retireesListen here:https://hackyourwealth.com/asset-location-part-2If you’re thinking about early retirement, what is your asset location plan? What are you holding in your taxable vs. tax-advantaged accounts? Let me know by leaving a comment.Don't miss an episode, hit that subscribe button...If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!Apple PodcastsOvercastSpotifyStitcherI need your help, please leave a listener review :)If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!Links mentioned in this episode:Wealth EngineersFinancial planning software: eMoney, Advyzon, CovisumAsset location: What assets should you hold in each account to minimize taxes? (HYW062)How to set your target asset allocation and rebalance your portfolio efficiently (HYW058)Schedule a private 1:1 consultation with meHYW private Facebook community Intro/Outro: Old Bossa by Twin Musicom.

#62: It might seem obvious that the best performing car isn’t just a function of the car itself…but also WHERE you’re driving it.Ferraris vs. Hummers will perform best in very different environments.When it comes to asset management, a similar thing is true.A few episodes back, I did a 3-part series on asset allocation. However, asset allocation is only part of the puzzle to optimizing your portfolio.To maximize total after-tax returns, WHERE you hold your assets is just as important as WHAT assets you hold.Asset allocation is WHAT you hold.Asset location is WHERE you hold it.You have to make sure you drive the Ferrari vs. the Hummer on appropriate terrains.Asset location strategy is about holding the right asset classes in the right accounts bearing the right tax profile.The goal is to minimize taxes on the way in, minimize tax drag while you invest, and minimize tax liability upon withdrawal.How do you do this?This week, I talk with Jonathan Duong, CFA, about how to manage your asset location to be as tax-efficient as possible. (This is part 1 of a 2-part discussion.)In addition to best practices and general principles, we discuss optimal asset location for:Stock holdings (both indexes and individual stocks, both dividend and non-dividend paying)Non-tax exempt bond holdingsTax-exempt bondsREITSPhysical real estateCheck it out here:https://hackyourwealth.com/asset-location-part-1What asset location principles are most relevant to you? Let me know by leaving a comment.Don't miss an episode, hit that subscribe button...If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!Apple PodcastsOvercastSpotifyStitcherI need your help, please leave a listener review :)If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!Links mentioned in this episode:Wealth EngineersFinancial planning software: eMoney, Advyzon, CovisumHow to set your target asset allocation and rebalance your portfolio efficiently (HYW058)Schedule a private 1:1 consultation with meHYW private Facebook community Intro/Outro: Old Bossa by Twin Musicom.

#61: All right champs – new year!That means a fresh opportunity for goal setting to transform your financial situation this year.To kick off the new year, I recorded a short episode this week about goal setting, mindset, and behaviors to help you make big strides toward your FIRE goals in 2021.I also invited a couple other leaders in the FIRE community to share their best advice when it comes to financial goal setting for people who are serious about pursuing FIRE.Check it out here:https://hackyourwealth.com/new-year-goals-2021Are you setting any FIRE related goals for 2021? What are they? Let me know by leaving a comment!Don't miss an episode, hit that subscribe button...If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!Apple PodcastsOvercastSpotifyStitcherI need your help, please leave a listener review :)If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!Links mentioned in this episode:The exact spreadsheet I use to analyze income, expenses, and net wealthSchedule a private 1:1 consultation with meHYW private Facebook community Intro/Outro: Old Bossa by Twin Musicom.

#60: Over the past year, I’ve done various podcast episodes about early retirement. I’ve also had numerous guests share their FIRE stories.But what about the tactical steps for how to FIRE?Many FIRE blogs talk a bit too high-level and not enough about the mechanics of how to do it, step by step.So in today’s episode, I share tactics and best practices I’ve observed on how to retire early. With confidence and assurance. With hard numbers and analysis. With a proper weighing of risks and tradeoffs.If FIRE is a goal for you, then be sure to listen closely for key insights on how to do it effectively.What you’ll learn:How to project your early retirement cash flow needs / expenses with clarity and confidenceHow to project your retirement income cash flows with clarity and confidence to match those expensesHow to build the investment assets needed to generate that retirement incomeThe 4 main type of investment assets for funding early retirement (and their tradeoffs)How to withdraw your retirement spending needs while minimizing riskHow certain life milestones will impact your income and expense projectionsTax planning in early retirementCheck it out here:https://hackyourwealth.com/early-retirement-fireWhat tips from today’s episode do you agree with / not agree with? What questions of yours about FIRE did I not answer? Let me know by leaving a comment.Don't miss an episode, hit that subscribe button...If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!Apple PodcastsOvercastSpotifyStitcherI need your help, please leave a listener review :)If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!Links mentioned in this episode:The exact spreadsheet I use to analyze my income, expenses, and net wealthHow to set your target asset allocation and rebalance your portfolio efficiently (HYW058)Download my FREE spreadsheet to track your current vs. target asset allocationRetirement withdrawal calculator: How long will your savings last in retirement?My 4×4 FIRE framework for creating and protecting wealth (HYW002)Schedule a private 1:1 consultation with meHYW private Facebook community Intro/Outro: Old Bossa by Twin Musicom.

#59: It’s hard to consistently beat the market as an investor…but it takes zero effort to match the market.Picking good index funds lets you match the market for near-zero cost.And matching the market produces some pretty good results. If you had invested – and held – $100k (and not a dime more) in a plain vanilla S&P 500 index fund in January 1990, today it would be worth over $1M.That’s 10x growth in 3 decades, or +7.7% annualized returns.That’s despite a 1990 recession, 2000-2002 dot com bust, 2008 financial crisis, and 2020 coronavirus.And all for zero effort.I dunno about you, but index fund investing sounds richer and a lot more laid back than active stock picking (which almost uniformly results in lower returns anyway).The key is picking good funds. What’s the best way to do this?This week, I talk with Jonathan Duong, CFA, founder of Wealth Engineers, a wealth management consultancy, about how to pick the best index funds to invest in.We discuss:Key differences between mutual funds vs. ETFs; between tracking, passive, and active fundsStep-by-step tips for evaluating an index fund: attributes, criteria, performance indicatorsRecommended online tools to search for and filter indexes and fund optionsHow fund expense ratios workSpecific names (and ticker symbols) of popular index funds for: total stock market, total bond market, government bonds, real estate, all-weather portfolioCheck it out here:https://hackyourwealth.com/best-index-fundsWhat are your favorite index funds, and why? Let me know by leaving a comment.Don't miss an episode, hit that subscribe button...If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!Apple PodcastsOvercastSpotifyStitcherI need your help, please leave a listener review :)If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!Resources mentioned in this episode:Wealth EngineersETF.comMorningstarETFdbETF ReplayMSCIThe CRSP IndexesUS total stock market: International stocks: Dividend-focused stocks: US investment grade bonds: US government and municipal bonds: International investment grade bonds: Real estate: Total market / all weather portfolio:Schedule a private 1:1 consultation with meHYW private Facebook community Intro/Outro: Old Bossa by Twin Musicom.

#58: How to set your target asset allocation can feel like a mystery. How do you do it rigorously? How do you know what’s optimal?Rebalancing can also feel like a chore. Where do you start? How do you make sure you’re doing it rigorously and tax-efficiently?This week, I show you how to set your target asset allocation tailored to your investment and risk profile. I share how to track your allocation over time and analyze drift from your target allocation. And I explain how to tax-efficiently rebalance back to your target allocation step-by-step.If asset allocation and portfolio rebalancing feels like a mystery, chore, or headache, then don’t miss this episode because it will teach you how to do it rigorously and with no guesswork.What you’ll learn:Why it’s prudent to sell your winning investments and rebalance toward your underdogsHow to create and define your target asset allocation starting from first principlesHow to determine your investment style and risk tolerance in an intellectually honest wayHow to track your current allocation and analyze drift from your targetHow to rebalance your portfolio tax-efficiently step-by-stepHow often you should rebalanceIf you really learn the principles taught in today’s episode, you’ll be able to rebalance your portfolio and ensure your asset allocation stays closely aligned with your investment goals (yielding higher returns and lower risk).…And you can do it in 1 hour or less per year.Check it out here:https://hackyourwealth.com/asset-allocation-rebalance-portfolioWhat is YOUR target asset allocation? How often do you rebalance? Any rebalancing strategies you use that I didn’t cover? What questions do you have about asset allocation and rebalancing? Let me know by leaving a comment!Don't miss an episode, hit that subscribe button...If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!Apple PodcastsOvercastSpotifyStitcherI need your help, please leave a listener review :)If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!Links mentioned in this episode:Download my FREE spreadsheet to track your current vs. target asset allocationMy 4×4 FIRE framework for creating and protecting wealth (HYW002)HYW private Facebook community Intro/Outro: Old Bossa by Twin Musicom.

#57: When it comes to investment management, it is crucial to write down your investing goals/plan in order to stay disciplined as an investor and get the returns you need with the least amount of risk possible.The way to do this is by writing an investment policy statement.This week, I explain about investment policy statements: what they are, why they’re important, and how to write a good one.What you’ll learn:What an investment policy statement is and why it’s important to your financial futureWhy a thoughtfully written IPS will turn you into a better investor and yield higher returnsHow to write a good IPSThe 3 crucial components all good investment policy statements haveHow often you should update your IPSWhen to reference your IPS on a day-to-day basisCheck it out here:https://hackyourwealth.com/investment-policy-statementIf you have an IPS, what are the key sections in it? When and how often do you reference your IPS? Let me know by leaving a comment.Don't miss an episode, hit that subscribe button...If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!Apple PodcastsOvercastSpotifyStitcherI need your help, please leave a listener review :)If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!Links mentioned in this episode:Schedule a private 1:1 consultation with meHYW private Facebook community Intro/Outro: Old Bossa by Twin Musicom.

#56: This week, I invited CPA Steve Nelson, whose tax blog I’ve followed for years, to chat with us about the details of how Section 199A works and the restrictions around it.199A created a huge new tax break for small business owners, partnerships, real estate investors, and contractors. But there was a lot of uncertainty initially due to seeming ambiguities and loopholes in 199A without clear guidance/regulations to address them.Now, two years later, a lot has become clearer.We discuss:Section 199A overviewWhat counts as Qualified Business IncomeKey rules and restrictions of 199AStrategies for maximizing the 199A deductionHow 199A might alter your retirement contribution strategySpecial considerations for real estate investors (including why a 1031 exchange may no longer make sense with 199A)Special considerations for professional service partnerships (law, medicine, accounting, etc)Special considerations for freelancers and online business ownersWhat happens to 199A after 2025Check it out here:https://hackyourwealth.com/section-199aAre you currently able to avail Section 199A? If so, how has it changed your business operations and/or financial planning considerations, if at all? Let me know by leaving a comment.Don't miss an episode, hit that subscribe button...If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!Apple PodcastsOvercastSpotifyStitcherI need your help, please leave a listener review :)If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!Links mentioned in this episode:Evergreen Small Business blogHow the final Trump tax bill affects you: analysis for early retireesHYW private Facebook community Intro/Outro: Old Bossa by Twin Musicom.

#55: This week, I explain 6 key areas where there may be significant tax code changes under a Biden administration – including how these changes may impact your personal financial planning and what actions you can take to prepare for them.What you’ll learn:How Biden’s proposal would impact income tax rates, deductions, and Section 199AHow it could impact capital gains and qualified dividends tax ratesHow estate taxes and the step-up in basis at death could changeImportant changes that would affect retirement account contribution deductionsHow 1031 exchanges for real estate investors might be impactedExpected changes to the corporate tax rateCheck it out here:https://hackyourwealth.com/biden-tax-proposalDo you plan to make changes to your portfolio or personal finances in anticipation of tax law changes under a new administration? Let me know by leaving a comment.Don't miss an episode, hit that subscribe button...If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!Apple PodcastsOvercastSpotifyStitcherI need your help, please leave a listener review :)If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!Links mentioned in this episode:How the final Trump tax bill affects you: analysis for early retireesHYW private Facebook community Intro/Outro: Old Bossa by Twin Musicom.

#54: In all my prior jobs except the current one, I can now say in hindsight that my 401k sucked.It only offered 10-15 fund options…which is like being forced to shop for weekly groceries in a gas station mini-mart when you know that Kroger is on the other side of the street.Their fund expense ratios were mediocre, even for the passive funds. You couldn’t beef up pre-tax money with additional after-tax money. There was no mega-backdoor Roth conversion option.These are really easy ways for companies to create value for employees via 401k plans. Why they are so often deficient when it comes to these things, I’m sure I don’t know.Luckily, there is a way you can take greater control over your 401k money (or IRA for that matter) to invest more freely and build wealth.It’s called a self-directed retirement account.This week, I chat with Dmitriy Fomichenko, a financial planner who specializes in using self-directed retirement accounts “with checkbook control” to beef up your investing and retirement planning strategy.What you’ll learn:What is a self-directed retirement account, the different types that exist, key risks, and how they differ from traditional retirement accountsThe process for setting up a self-directed retirement account, and how to fund itMaintenance costs associated with self-directed accountsThe role of the custodian / trustee / administrator for self-directed accountsHow to access your self-directed account funds to invest (and key differences here between 401k vs. IRA versions)What kind of assets you can invest in with a self-directed account, and how income and expenses generated by those investments are treatedWhy mixing outside funds with self-directed account funds is such a big no-no, and the consequences if you doCheck it out here:https://hackyourwealth.com/self-directed-retirement-account-401k-IRAAre you satisfied with your 401k? Why or why not? Does a self-directed account sound appealing? Why or why not? Let me know by leaving a comment when you’re done.Don't miss an episode, hit that subscribe button...If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!Apple PodcastsOvercastSpotifyStitcherI need your help, please leave a listener review :)If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!Links mentioned in this episode:Sense Financial free consultationList of non-recourse lendersEverything you need to know about 401Ks (HYW003)IRAs, Roth IRAs, and how to get the tax benefits of BOTH (HYW004)18 real estate investors share what they wish they knew at college graduationHYW private Facebook communityIntro/Outro: Old Bossa by Twin Musicom.

#53: No matter how you cut it, the cost of college these days is pretty crushing.And getting into your top choice college is well and good and all, but it doesn’t matter much unless you can afford to attend!How can parents and families afford college (potentially for multiple kids) without ravaging their retirement savings?This week, I invited my friend Ann Garcia, aka the “College Financial Lady,” back to the podcast to explain the intricacies of how college financial aid works. She shares insights and wisdom on how to plan for the cost of college, the different types of aid available, and strategies for maximizing financial aid.We discuss:A big picture framework thinking about college financial aidThe overall financial aid process, timeline, and key datesThe role each type of aid (need-based, merit, government, and college aid) plays in a family’s financial aid strategyHow FAFSA works, the 4 buckets of money that must be reported, what money can be excludedWhat federal EFC is, how it’s calculated, and how it’s usedWhat the CSS Profile is, key differences vs. FAFSA, and what money must be reported on itHow CSS Profile schools calculate EFC and differences vs. FAFSA methodologyWhen it might be useful to leverage a grandparent-funded 529 plan + tradeoffsStudent loan options and key types of loans available to studentsTips for negotiating / appealing your financial aid packageFinancial strategies related to the “prior-prior” year once January of sophomore year arrivesFinancial strategies in the years BEFORE your child applies for college financial aid to maximize aidCheck it out here:https://hackyourwealth.com/college-financial-aidHas your child (or children) attended college with financial aid? What surprised you about the financial aid process? What do you wish you had known that you know now? What other questions do you have about financial aid? Let me know by leaving a comment when you’re done.Don't miss an episode, hit that subscribe button...If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!Apple PodcastsOvercastSpotifyStitcherI need your help, please leave a listener review :)If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!Links mentioned in this episode:The College Financial LadyCollege DataFederal housing multiplier index for financial aid529 college savings plans: rules, tax benefits, & qualified expenses (HYW026)College financial aid strategies to optimize your assets, income & EFC (HYW025)HYW private Facebook community Intro/Outro: Old Bossa by Twin Musicom.

#52: The competition for admissions to the most elite colleges in America (think Ivy League, US News top 10) is fiercer than ever.That’s because top colleges provide the best academic opportunities. Resources. Career opportunities. Pathways to elite grad schools. Student and alumni communities (where you’ll forge lifelong connections, friendships, potentially even meet your spouse). Not to mention, you’ll have a powerful brand associated with you for life.How can students and parents without special connections distinguish themselves amidst a sea of qualified applicants?This week, I chat again with my friend Shirag Shemmassian, a college admissions expert who has coached thousands of students to successful admission at elite colleges, about the mindsets and accomplishments you really need to win admission to the most elite colleges.We discuss:Biggest myths and misconceptions when it comes to getting into elite collegesWhat elite college admissions committees are looking for, and how to differentiate yourselfWhat level/degree of accomplishment you need to get inWhat students (and parents) can do well ahead of the application year to distinguish themselves, and how far in advance to do itHow lower / middle income / rural / etc students with access to fewer opportunities can still differentiate themselves compellinglyWhy your “message” and the way you deliver it is just as important as your actual accomplishmentsThe mindset students should have when writing their college essaysHow to pick an essay topic and write it compellingly (even if you’re not a great writer)Who should write your recommendation letters, and how to build genuine relationships with recommenders that blossom into great lettersThe qualities that make a stand-out recommendation letterCheck it out here:https://hackyourwealth.com/college-admissionsDid you attend (or send your kid to) an elite college? What do you think principally contributed to your / their admissions success? What would you have done differently if you could do it over? Let me know by leaving a comment when you’re done.NOTE: Apologies in advance we had some audio problems in the second half of the interview, so some parts may sound choppy. However, all key points should still be clear. I’ve also cleaned up the transcript (at the link above) to fill in missing words / phrases, so check that out if you’re struggling to understand any key points.Don't miss an episode, hit that subscribe button...If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!Apple PodcastsI need your help, please leave a listener review :)If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!Links mentioned in this episode:Shirag's guide to getting into top collegesShirag's successful college essay examplesShirag's tips on writing the common app essayHow to attend any college for free, with Shirag Shemmassian, PhD (HYW039)HYW private Facebook communityIntro/Outro: Old Bossa by Twin Musicom.

#51: Despite the pain (and cost) that not having an estate plan will cause your heirs, fully two-thirds of Americans don’t even have so much as a will if they got hit by a bus.There are many reasons why people fail to create an estate plan. None are good.So for this week’s podcast, I invited Spiro Verras, a Florida estate planning attorney, to share key things you need to know about creating a proper estate plan.We discuss:Elements of a good estate planHow probate works step by step, how long it takes, and how much it costsAt what point in your life you should write a willDifferences between wills and trustsLegal formalities of wills and trustsHow wills and trusts change the probate processWhat DIY-ers need to know before drafting their own estate planning docsSpecial considerations for real estate investors, family business owners, professional service practice owners, and high net-worth individualsCheck it out here:https://hackyourwealth.com/estate-planning-basicsDo you have a will or trust? What about a medical directive or power of attorney agreement? Have you ever been through the probate process? What was it like for you? Let me know by leaving a comment!Don't miss an episode, hit that subscribe button...If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!Apple PodcastsOvercastSpotifyStitcherI need your help, please leave a listener review :)If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!Links mentioned in this episode:Verras LawHow to write a willHow to set up a revocable living trust (with sample trust document)HYW private Facebook community Intro/Outro: Old Bossa by Twin Musicom.

#50: Social Security is crucial to American retirement. 1 in 5 Americans and 1 in 4 families depend on it. That’s 65M people who will collect $1 trillion in Social Security benefits in 2020.I said, $1 trillion.With this massive of an entitlement program, it serves you well to understand how it works in gory detail so you can maximize your benefits. Sound good?(If you’re a youngster, don’t glaze your eyes over…you may think Social Security is not relevant to you anytime soon, but what you do now impacts how much you collect in the future. So listen up – your retired self will thank you….)This week, I invited Jim Blair to come share the goods on how Social Security works. Jim is a Social Security expert who spent 35 years at the Social Security Administration advising on benefits and claims, so he knows a thing or two about it.We discuss:How Social Security benefits are calculatedKey factors to consider when deciding what age to claimOptimal claiming strategies and tradeoffs of claiming younger vs. olderHow spousal, divorced, and survivor benefits work (and how they impact your claiming strategy)When Social Security is subject to taxes (and how much)What is likely to happen to Social Security when its assets go to zero (in

#49: The Health Savings Account is an incredible tool to take greater control over your healthcare. It is the most tax-efficient investment account on the planet.So, if you’re eligible for it and not at least considering how to take advantage of it, you’re missing out.In this week’s podcast, I deep dive on HSAs with Roy Ramthun. Roy is a nationally-recognized HSA expert, because he led the Treasury Department’s implementation of HSAs when they were signed into law in 2003, and then he served as a White House healthcare policy advisor.I thought I already knew a lot about HSAs, but I still learned new things from Roy.We discuss:How Roy got the nickname “Mr. HSA”Why HSAs are so special and how they workTax benefits of HSAs at both federal and state levelThe 3 main eligibility criteria for HSAsWays to fund HSA contributionsWhat health expenses are considered qualifiedHSA bank options and factors to consider when selecting a custodian bankReimbursement rules, receipt saving tipsTips for maximizing the growth of your HSAWhat happens to your HSA when you retire or pass awayDo you have an HSA? What kind of health expenses have you been able to save on using an HSA? Any follow up questions for Roy? (He’s offered to help answer them.) Let me know by posting a comment on the show notes page.Don't miss an episode, hit that subscribe button...If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!Apple PodcastsSpotifyGoogle PodcastsStitcherI need your help, please leave a listener review :)If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!Links mentioned in this episode:HSA Consulting ServicesHealth Savings Accounts: Contribution Limits, Eligibility Rules, BenefitsHYW private Facebook communityIntro/Outro: Old Bossa by Twin Musicom.

#48: Seniors often enter retirement (a) thinking Medicare is free, and (b) not at ALL clear how the details work – rules, restrictions, limitations, costs.But it’s most certainly not free: your portion of costs could be unlimited and bankrupt you. And, like other healthcare matters in the US, “how it works” gets complicated fast!How can seniors (and their loved ones, like you) make sense of it all?This week, I talk with Danielle Kunkle Roberts, a nationally-recognized expert on Medicare insurance, about how to evaluate, navigate, calculate, and decide on the best configuration of Medicare coverage for you and your family. If health insurance “peace of mind” is important to you in your elder years, this is an action-packed episode you do not want to miss.What you’ll learn:Medicare eligibility requirementsOptions for expats who haven’t paid into Medicare taxesWhat exactly Medicare covers, how each “part” works, and premium costsHow to determine which doctors, hospitals, clinics, and pharmacies will accept your Medicare coverageHow the premium surcharge (IRMAA) works if your income exceeds certain thresholdsAll-in costs you can expect to pay for Medicare coverageHow the “initial enrollment period” works, including how the penalty worksHow Medicare Advantage works + when it’s a better choice than original Medicare (tradeoffs, considerations, cost differences, network differences)How Medigap works and tradeoffs and considerationsHow expat retirees should plan for Medicare, given it generally doesn’t cover them overseasWhat other questions do you have about Medicare? If you’re looking into Medicare for yourself or a loved one, are you leaning toward original Medicare or Advantage? Why? Let me know by leaving a comment right now.Don’t miss an episode, hit that subscribe button…If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!Apple PodcastsOvercastSpotifyStitcherI need your help, please leave a listener review If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!Links mentioned in this episode:Boomer Benefits websiteBoomer Benefits Book: 10 Costly Medicare Mistakes You Can’t Afford to MakeBoomer Benefits private Facebook groupBoomer Benefits YouTube video: Will Medicare Cover My Procedure?Medicare.gov: What Medicare CoversMedicare.gov: Find & compare doctorsMedicare.gov: Medicare plan finder toolCPT codes & ICD 10 codes: How medical billing & insurance claims work (HYW020)HYW private Facebook community Intro/Outro: Old Bossa by Twin Musicom.

#47: In this week’s podcast, I explain how to create a family emergency binder using 11 essential categories of info to make it easy for loved ones to understand your finances and figure out what you have, what you owe, and what you’re owed.What you’ll learn:11 essential types of info to include in your binderTips on how to organize documents, PDFs, spreadsheets, and videosHow often to update it + tips on staying organizedWhy it’s worth starting now, even if it takes a long time to finishDo you have a family emergency binder? What other info do you think belongs in it? Let me know by leaving a comment when you’re done.Don’t miss an episode, hit that subscribe button…If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!Apple PodcastsSpotifyGoogle PodcastsStitcherI need your help, please leave a listener review If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!Links mentioned in this episode:Free downloadable checklist: 11 Essential Categories of Financial Info For Family Emergency Binders16 essential estate planning checklist topics to protect your family and give you peace of mind (HYW009)HYW private Facebook communityIntro/Outro: Old Bossa by Twin Musicom.

#46: Most people know what life insurance is. But they tend to think of it as term life: fixed payments for 20-30 years that pay out a death benefit if you die before the term is up (while paying nothing if you outlive it).There’s another type of life insurance called permanent life insurance. It never expires. The most common type is whole life insurance.Whole life insurance can get very complicated, so I invited a financial planning veteran with extensive experience in it (not affiliated with any insurance company) to share insight on how it works.This week, I talk with Eric Brotman, CEO of BFG Financial Advisors, a wealth management consultancy, about the intricacies of whole life insurance: who it’s best suited for, its tax and estate planning benefits, and how to use it for investing purposes.What you’ll learn:How a policy his parents bought for him at 14 which he inherited at 24 got him hooked on whole life insuranceThe main tax advantages of whole lifeHow whole life is used for estate planningThe type of securities life insurance companies invest inHow to choose a whole life insurance companyHow life insurance broker commissions work (and how much they are)What paid-up additions are and why they matterHow to borrow against your whole life policyThe tradeoffs of borrowing from vs. against your policyHow whole life can supplement social security in retirementIf you have whole life insurance, are you satisfied with it? Why or why not? If you borrow against your life insurance to invest in other assets, what do you invest in? Let me know by leaving a comment.Don't miss an episode, hit that subscribe button...If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!Apple PodcastsSpotifyGoogle PodcastsStitcherI need your help, please leave a listener review :)If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!Links mentioned in this episode:Brotman Financial Groupwww.lowtaxbook.comDon't Retire...Graduate PodcastHYW private Facebook community Intro/Outro: Old Bossa by Twin Musicom.

#45: Early retirement must be executed differently, and very intentionally, with kids. There are no easy, silver-bullet solutions.I think about this topic often. And, ever since my kiddo popped out a few years ago, I’ve made real changes to my financial planning in response – from building larger, stronger passive income streams to doing very detailed financial analysis of kid costs that, in turn, have influenced our planning decisions.This week, I invited to the podcast Michael Quan, an early retiree (now blogger) with 2 kids who founded and ran an IT services company for a decade before selling it (and not for “FU money” btw) and retiring. I ask about Michael’s mindset, actions, and challenges he faced when early retiring with kids.We discuss:How the financial crisis motivated Michael to start his own companyHow much he had saved up on the day he retired vs. where his portfolio is at nowWhen did kids enter the picture relative to his retirement dateHow kids impacted the family budget, including lifestyle trade-offs they made to accommodateKey areas where early retirement actually brought significant savingsHow Michael spends his days nowHow having kids has influenced the way he thinks about wealth buildingWhat resonated with you from Michael’s story? What seemed less relevant to your own situation? Let me know by leaving a comment when you’re done.Also: I want to bring on more guests who have FIRE’d with kids.Michael’s is one story, and hopefully you got good nuggets of insight from it, but it’s not the only story. If you know a good potential guest (early retiree family with unique story), tell me about them. I’d love to reach out.Don't miss an episode, hit that subscribe button...If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!Apple PodcastsSpotifyGoogle PodcastsStitcherI need your help, please leave a listener review :)If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!Links mentioned in this episode:Financially AlertBreakthrough Millionaire PodcastThe FIRE Planner bookHYW private Facebook communityIntro/Outro: Old Bossa by Twin Musicom.