#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 ?. In 2021, this trend exploded. ?? In 2022, when flying became a thing again, so did “revenge travel.” STRs accelerated even more. ??? With average daily rates skyrocketing the l ..read more

#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 iden ..read more

#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 ..read more

#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 a ..read more

#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 diligence The 4 big things to look for in disclosure packets How to eval ..read more

#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 t ..read more

#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, fou ..read more

#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 ..read more

#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 as ..read more

#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 ..read more