#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 planning
• What retirees should think carefully about when it comes to health insurance in retirement
• How those considerations change depending on your retirement age
• Checklist for choosing the right health insurance plan if you’re retiring soon
• Common mistakes retirees make when planning for post-retirement healthcare
• When self-insuring might be your best choice in retirement
• How medical tourism can play an important role in retirement healthcare
• What retirees should know about buying health insurance on ACA marketplace exchanges

Check it out here:

https://hackyourwealth.com/health-insurance-retirement-planning

If 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.

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Related links:

• https://www.healthinsurance.org
• https://www.healthcarebluebook.com
• https://www.medibid.com
• https://www.linkedin.com/in/bo-bowen-1b64341a6
• Schedule a private 1:1 consultation with me
• HYW private Facebook community

Intro/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 🔥.

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 last couple years, hordes of real estate investors snapped up homes to turn them into Airbnbs, trying to chase yield.

Now the market is super saturated, with daily rates even contracting in places, and there’s tons of new short-term rental inventory (over half of Airbnb listings added since 2020).

So how can you stand out as an STR real estate investor in the current climate?

In this episode, I interview Diya Liu, a seasoned short-term rental investor who scaled from zero to 9 STRs in one year, netting $100k annual profit, and then quit her BigLaw job to do short-term rental real estate investing full-time. She currently owns three hotels and a dozen STRs.

We discuss:

• Diya’s RE portfolio breakdown - STRs vs. hotels
• Her step-by-step analysis process for screening potential STR vs. hotel deals
• How she analyzes local STR regulations in a market
• Key interior design principles she implements for her STRs
• Marketing strategies to help your STR stand out
• Automation strategies for your STRs - using VAs, messaging guests, etc
• How she met her investment partners and how they split up work

​Check it out here:

​https://hackyourwealth.com/short-term-rental-hotel-investing​

​Are you an STR investor? If so, how have bookings changed in the last 1-2 years? Do you see over-saturation in listings inventory in your area? Are you trying out any different strategies this year? Let me know by leaving a comment.

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Related links:

• https://www.instagram.com/diyaesq
• https://www.facebook.com/groups/AirbnbProfessional
• Schedule a private 1:1 consultation with me
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

#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 options
• When it makes sense to simply self-insure
• Tracy’s observations on which countries offer both high-quality and affordable healthcare
• Tracy’s health insurance recommendations for early retirees who wish to travel abroad 100% vs. 90% vs. 50% vs. 25% of the time
• ACA marketplace health insurance options to consider for early retirees
• How Medicare coverage is impacted when you travel long-term
• When it’s worth repatriating to the US vs. staying in-country to get medical care, plus what kind of insurance plans provide repatriation services

Check it out here:

https://hackyourwealth.com/health-insurance-retirement-travel

If 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.

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Related links:

• About Tracy Winters
• Schedule a private 1:1 consultation with me
• HYW private Facebook community

Intro/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 retirement
• How she came up with her FIRE number
• Her numbers: earning/income trajectory from MBA graduation to early retirement, spending level during her career & now in retirement
• Her asset allocation + tactics she uses for managing, rebalancing, risk mitigation, and withdrawing from her portfolio
• Factors she considered in terms of spouse/family vs. early retirement
• Advice on dating and companionship in early retirement
• What she learned about finding a new non-career identity, purpose, and fulfillment in early retirement
• How Kim spends her days now & how she’s found community as an early retiree
• Her advice for other young women who are interested in FIRE

Check it out here:

https://hackyourwealth.com/retire-early-women-business-career-professional

Know 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.

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Intro/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 dentist
• Net worth after finishing dental school
• Age when he broke even and when he reached FI
• How much he earned right out of dental school, when he broke even, when he reached FI, plus how much he earns passively now
• Spending level over the years, plus how much he spends post-FI
• Asset allocation breakdown
• Main actions he took that had the biggest impact on net worth
• His thought process on stepping back from clinical work with two young kids still in tow
• FIRE tips for people with kids

Check it out here:

https://hackyourwealth.com/dentist-financial-independence-retire-early

What 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.

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Related links:

• Schedule a private 1:1 consultation with me
• HYW private Facebook community

Intro/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 different
• The mind-boggling cost of college today; forecasted cost in 15 years
• Why college costs so much now, what’s driven up the cost in recent decades
• Goals that colleges are trying to accomplish with their financial aid awards
• Things parents should do to prepare their child and finances for the cost of college from birth to high school
• Why it’s important for your child to do the official campus tour for colleges they’re interested in
• Recent key changes and updates to the FAFSA process
• Difference between 529 savings plans vs. pre-paid tuition plans vs. Private College 529
• Mechanics of 529s: roll-over-ability, qualified expenses, taxes & penalties for non-qualified expenses, how scholarships are handled, changing beneficiaries

Check it out here:

https://hackyourwealth.com/how-to-pay-for-college

Have 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.

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Related links:

• Book: How to Pay for College: A complete financial plan for funding your child's education
• Online course: The College Financial Plan Masterclass - 20% discount exclusively for HYW subscribers (use code: HYW20)
• TheCollegeFinancialLady.com
• 529 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 me
• HYW private FB community

Intro/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 diligence
• The 4 big things to look for in disclosure packets
• How to evaluate the history of previous remodels, structural changes, or additions to the house done by prior owners
• Special tips for buying a condo – how to analyze HOA records, financials, rules, and CC&Rs
• My 12-point checklist on what to look for when touring a home in person

Check it out here:

https://hackyourwealth.com/real-estate-due-diligence

If you’ve bought a home before, what are the most important due diligence items you look for? Let me know by leaving a comment.

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Related links:

• Battle-tested home remodeling tips for saving serious money and getting the most from your contractors
• How to find and vet good home remodeling contractors like a boss
• How 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 for
• How to research real estate markets: The single best resource you need
• Avoiding capital gains tax on real estate: how the home sale exclusion works
• The True Benefit of Homeownership (why buying has paid off over renting, even in a million dollar market)
• Schedule a private 1:1 consultation with me
• HYW private Facebook community

Intro/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 Roth
• How to execute each one + tips to ensure no tax liability when you convert
• What plan features your employer 401k must have to do a mega backdoor Roth
• Workaround 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 it
• A note about doing mega backdoor Roth conversions via Solo 401k.

Check it out here:

https://hackyourwealth.com/mega-backdoor-roth

Have 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.

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Related links:

• Traditional vs. Roth? How to double-dip on the tax benefits of BOTH
• What is a Solo 401k? And Why It Beats All Other Retirement Accounts
• Everything 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 me
• HYW private Facebook community

Intro/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 recruiting
• How the pandemic changed norms around remote work
• What types of jobs are most in-demand for remote work right now
• What types of jobs still have not embraced remote work
• Skills 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 employees
• How companies can promote strong, healthy remote work cultures

Check it out here:

https://hackyourwealth.com/future-of-remote-work

And 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!

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• DistantJob
• Surviving Remote Work: How to Thrive as a Leader and Entrepreneur in the Remote Age
• Schedule a private 1:1 consultation with me
• HYW private Facebook community

Intro/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 proposed
• Pfau’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 retirees
• Pfau’s thoughts on asset allocation in the current environment of rising interest rates, high inflation, and high asset valuations
• What Pfau personally projects as his assumed real rate of return on stocks for his own portfolio
• How annuities can play a crucial role in your retirement portfolio depending on your investor risk profile and desired stock allocation
• Pfau’s framework of 4 retirement styles + optimal asset allocation for each

Check it out here:

https://hackyourwealth.com/4-percent-rule

What 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.

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Links mentioned in this episode:

• Wade Pfau
• Retirement Planning Guidebook
• Safety-First Retirement Planning: An Integrated Approach for a Worry-Free Retirement
• How Much Can I Spend in Retirement?
• Reverse Mortgages: How to Use Reverse Mortgages to Secure Your Retirement
• Schedule a 1:1 consultation with me
• HYW private Facebook community

 Intro/Outro: Old Bossa by Twin Musicom.