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Healthcare planning = retirement planning06 Jun 202301:14:21

#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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Intro/Outro: Old Bossa by Twin Musicom.

Real estate investing in short-term rentals and hotels04 Apr 202300:56:12

#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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Intro/Outro: Old Bossa by Twin Musicom.

How current economic changes impact retirement safe withdrawal rates11 Jan 202201:49:58

#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 planning
  • What new safe withdrawal rate % retirees should consider right now
  • Whether investors should potentially update their asset allocation given current macro trends
  • Whether he believes asset prices are overvalued right now
  • Alternative assets (like cryptocurrencies) and their merits / concerns
  • How much cash he believes is advisable to hold right now


Do 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!

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 Intro/Outro: Old Bossa by Twin Musicom.

REPLAY: How to set and rebalance your asset allocation efficiently27 Dec 202100:36:29

#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 underdogs
  • How to create and define your target asset allocation starting from first principles
  • How to determine your investment style and risk tolerance in an intellectually honest way
  • How to track your current allocation and analyze drift from your target
  • How to rebalance your portfolio tax-efficiently step-by-step
  • How often you should rebalance

Check it out here:

https://hackyourwealth.com/asset-allocation-rebalance-portfolio-replay


How often do you rebalance your portfolio? Let me know by leaving a comment!

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Links mentioned in this episode:

 Intro/Outro: Old Bossa by Twin Musicom.

Retirement withdrawal strategies: tax-efficient portfolio drawdowns02 Nov 202100:52:24

#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:

  1. meet all your monthly cash flow needs
  2. cushion against unexpected expenses
  3. minimize tax liability
  4. ideally help your kids / grandkids, give to charity, or leave a legacy
  5. ensure your retirement nut doesn’t run out before you do

This 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 sequence
  • How 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 withdrawals
  • How soon-to-be and current retirees can protect themselves against sequence of returns risk
  • When it makes sense to use legal tools like tax-free gifts, GRATs, etc, to reduce tax liability on retirement assets
  • Why 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 them
  • Portfolio withdrawal advice for early retirees (FIRE)

Check it out here:

https://hackyourwealth.com/retirement-withdrawal-strategies

Do 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.


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 Intro/Outro: Old Bossa by Twin Musicom.

Annuities explained: are annuities a good investment for retirement?19 Oct 202101:01:34

#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 serve
  • The 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 inflation
  • The mechanics of how to buy an annuity
  • How insurance companies that sell annuities make money
  • The different type of annuity fees you can expect, and typical all-in costs for different annuity types
  • How to vet the insurance companies that sell annuities
  • How to vet an agent and questions to ask before buying an annuity from them
  • How agents who sell annuities are compensated
  • Annuity taxes and the tax profile of annuities
  • Basic protections your annuity gets if the insurance company you bought it from goes bankrupt
  • Who annuities are best suited for, and whether annuities are a good idea for early retirees (FIRE)

Check it out here:

https://hackyourwealth.com/annuities


Have 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.

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Links mentioned in this episode:

 Intro/Outro: Old Bossa by Twin Musicom.

Taxes on stock gains: how to avoid capital gains tax on stocks05 Oct 202100:40:44

#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 to
  • Difference between short-term vs. long-term capital gains tax treatment
  • How capital gains and losses work in tandem come tax filing time
  • How to harvest capital losses and harvest capital gains
  • Current proposed legislative changes to capital gains tax rates
  • What investors may want to consider doing now before potential changes take effect

Check it out here:

https://hackyourwealth.com/capital-gains-tax-on-stocks

What other tax planning questions do you have about capital gains taxes? Let me know by leaving a comment.

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 Intro/Outro: Old Bossa by Twin Musicom.

Teaching your kids about money and financial independence21 Sep 202101:24:31

#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 low
  • Why letting your kids buy “One Special Thing” per shopping trip is an effective teaching strategy
  • Why you might want to pay your kids for jobs, but not chores…and the difference between the two
  • Why it might not be a good idea to pay your kids for getting good grades, and what you can do instead
  • Why “profit sharing” is an especially powerful strategy to teach kids about savings and frugality
  • How to create a “kid 401k” to teach your kid lasting lessons about compounding and long-term investing
  • How to incentivize your kid to contribute to a Roth IRA early on
  • How to handle the question of “how rich are we?”

Check it out here:

https://hackyourwealth.com/teaching-kids-about-money-financial-independence


What 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.

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 Intro/Outro: Old Bossa by Twin Musicom.

College student financial aid changes coming to the FAFSA application07 Sep 202100:55:17

#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 dates
  • Important changes coming to the federal financial aid process: for the FAFSA application, families with multiple college-aged kids, grandparent 529 plans, divorced parents, and more
  • Timeline and phasing of these changes coming in 2021, 2022, 2023 and beyond

Check it out here:

https://hackyourwealth.com/fafsa-federal-student-financial-aid-changes

Will 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.

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 Intro/Outro: Old Bossa by Twin Musicom.

Money lessons for kids: Tips from other personal finance influencers24 Aug 202100:11:00

#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-influencers

What strategy have YOU found to be most effective when it comes to teaching your kids about money? Let me know by leaving a comment.

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Links mentioned in this episode:

 Intro/Outro: Old Bossa by Twin Musicom.

Financial literacy for kids: how to teach your kids about money10 Aug 202101:00:12

#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 hard
  • What financially well-educated kids have in common
  • The right age to start teaching kids about money in earnest
  • The crucial money lessons kids at each maturity level should know to have healthy skills, habits, and mindsets about money
  • Robin’s core framework for teaching kids about money
  • Common mistakes parents make when teaching their kids about money, and the most effective role modeling parents can do to successfully teach their kids about money
  • How to get kids to become self-motivated to learn about money, saving, investing, and budgeting
  • How parents can create teachable moments in daily life and turn them into money lessons for their kids
  • How 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 money
  • Guidelines for paying kids an allowance or paying kids to do chores
  • How 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 brats

What 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.

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Intro/Outro: Old Bossa by Twin Musicom.

Language learning through travel immersion courses in early retirement27 Jul 202101:11:37

#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 number
  • Her asset allocation and withdrawal rate
  • Her blog’s revenue contribution (and what helped her blog get traction)
  • How Ingrid plans travel around language immersion courses
  • How she meets and connects with locals when she travels, plus her advice for solo female travelers
  • How she handles health insurance and healthcare costs as an early retiree and when she’s traveling
  • How she believes one’s emotional well being and personality change in early retirement
  • How 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 retiree
  • What Ingrid would have done differently if she could do it over again

Check it out here:

https://hackyourwealth.com/language-learning-courses-retirement-travel-immersion

Have 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!

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Intro/Outro: Old Bossa by Twin Musicom.

Health insurance for traveling early retirees22 Nov 202200:53:49

#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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Intro/Outro: Old Bossa by Twin Musicom.

How this middle income couple built a real estate portfolio of 25 doors (in expensive California!)13 Jul 202101:08:55

#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 place
  • Their 25-door real estate portfolio breakdown – what type of units, where they’re located, how many have mortgages
  • How they financed the down payments and loans for each property
  • Why they chose the neighborhoods they invest in
  • Why they self-manage, and their best tips for managing tenants effectively
  • Their views on Section 8 and how they manage Section 8 tenants
  • Why they never plan to stop investing…even though they’re 65!

Check it out here:

https://hackyourwealth.com/real-estate-investing-with-middle-class-income

Do 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.

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Links mentioned in this episode:

 Intro/Outro: Old Bossa by Twin Musicom.

How to early retire (FIRE) if your spouse isn’t on board29 Jun 202100:55:08

#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 FIRE
  • Her spouse’s main concerns when it came to early retirement
  • How 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 retirement
  • Plus: how Caroline handles healthcare / insurance as an early (pre-Medicare) retiree, her passive rental real estate portfolio breakdown and how she manages her rentals remotely

Check it out here:

https://hackyourwealth.com/retire-early-with-spouse-working

Have 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.

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Stock option and RSU tax planning15 Jun 202101:07:46

#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 each
  • Deep dive on Incentive Stock Options + AMT + AMT “refund” rules
  • How an 83(b) election works, and pros/cons of doing it
  • Key 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-planning


Do 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.

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1031 exchanges: what real estate investors need to know01 Jun 202101:10:59

#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 exchanges
  • Key criteria and deadlines + step-by-step process for executing a 1031
  • How to optimize timing your buy/sell transactions
  • Like-kind replacement property rules
  • Domestic vs. foreign property exchanges
  • What constitutes “Qualified Use” + holding period requirements
  • State tax consequences
  • Why investors can’t do 1031s themselves
  • The role of a Qualified Intermediary, how to vet one, and how much they cost
  • Tax impact of converting a 1031 property into owner-occupied housing, and vice versa
  • Common mistakes that disqualify you from a 1031
  • Proposed Biden administration changes to 1031s: likelihood of passage + actions you can take now to mitigate adverse tax impact

Check it out here:

https://hackyourwealth.com/1031-exchange

Ever done a 1031 transaction? What was your experience? Anything you would do differently next time? Let me know by leaving a comment.

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Buying tax deeds to invest in real estate at a deep discount18 May 202101:16:01

#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 investing
  • How tax deed auctions work, how they differ from other foreclosure auctions
  • The most important things to due diligence when it comes to tax deed properties, and how to due diligence them
  • The most helpful online tools for property due diligence
  • How 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 them
  • How a quiet title lawsuit works, how much it costs, and what happens if a title dispute arises
  • How tax deed auctions affect existing mortgages and liens, and how to verify the rules in your state

Check it out here:

https://hackyourwealth.com/tax-deed-investing

Have 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.

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  Intro/Outro: Old Bossa by Twin Musicom.

Is rental real estate a safer type of “yield shield”?04 May 202100:29:26

#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 allocation
  • Whether a bond tent strategy is still relevant if you have rental real estate
  • How to analyze the sequence risk crossover point after which you are guaranteed to outlive your savings
  • How 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-analysis

Do 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!

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Does a “yield shield” really protect against sequence of returns risk?20 Apr 202101:00:43

#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 strategy
  • Whether investing in dividend kings or dividend aristocrats helps to address the cons
  • The importance of looking at total return when analyzing the yield shield, and why a high dividend doesn’t translate into higher total return
  • Reasons why the yield shield can fall short (and examples where it did)
  • The right way to define success of a yield shield strategy
  • Why Karsten doesn’t fundamentally believe the yield shield does better than a plain vanilla stock index

Check it out here:

https://hackyourwealth.com/yield-shield-critique

This 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.

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  Intro/Outro: Old Bossa by Twin Musicom.

How to use a bond tent to reduce sequence of returns risk06 Apr 202100:56:32

#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 paths
  • Pros and cons of a bond tent strategy (what you gain, what you lose)
  • How to determine the optimal % peak allocation of bonds
  • How 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 risk
  • When is a bond tent NOT worth it and you should just stick with 100% equities

Check it out here:

https://hackyourwealth.com/asset-allocation

What do you think about the bond tent strategy? Let me know by leaving a comment.

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  Intro/Outro: Old Bossa by Twin Musicom.

Tax filing updates to be aware of this year (tax year 2020)23 Mar 202100:38:30

#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 checks
  • Healthcare 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 taxes
  • Education related changes (e.g., student loan payments)
  • Charitable donation changes
  • Commonly missed business deductions for self-employed / sole proprietors
  • Tax 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-filing

What 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!


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Intro/Outro: Old Bossa by Twin Musicom.

How tax lien investing works and how to buy tax lien certificates09 Mar 202101:14:36

#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 it
  • Differences between tax lien vs. tax deed investing
  • How tax lien interest rates are set + realistic rates you can expect
  • What makes an ideal tax lien investment
  • Due 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 house
  • How tax lien auctions work + winning bid strategies
  • How tax lien investment funds work + tradeoffs of investing in a fund

Check it out here:

https://hackyourwealth.com/tax-lien-investing

Have 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.

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  Intro/Outro: Old Bossa by Twin Musicom.

How a female MBA early retired at 39 (+ her advice for women pursuing FIRE)18 Oct 202201:05:35

#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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Marriage and money: why spouses fight about money, how to fight with empathy, and how to convince your spouse to FIRE23 Feb 202100:50:55

#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 money
  • Whether keeping separate money accounts is a good idea
  • How to fight about money productively, with empathy, to keep your relationship healthy and even strengthen it
  • Where spouses should learn to compromise when it comes to money and finances
  • Intentional money rituals that spouses can do to keep their relationship healthy
  • How 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-marriage

What 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.

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 Intro/Outro: Old Bossa by Twin Musicom.

How to talk about money when you’re dating09 Feb 202100:48:44

#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 values
  • Tips for asking sensitive money-related questions that don’t rub your partner the wrong way
  • How to handle it if your partner does get defensive or reacts the wrong way
  • Tips for attracting a partner who shares your financial values
  • What to do if you’ve met “the one” but have totally different mindsets and behaviors about money

Check it out here:

https://hackyourwealth.com/money-dating

How 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.

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 Intro/Outro: Old Bossa by Twin Musicom.

Asset location for non-traditional assets + considerations for early retirees02 Feb 202100:35:40

#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)
  • Currencies
  • Illiquid investments like LPs, private equity, private loans, etc
  • Speculative holdings like Bitcoin, art, collectibles
  • How asset location considerations might change for early retirees

Listen here:

https://hackyourwealth.com/asset-location-part-2

If 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.

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 Intro/Outro: Old Bossa by Twin Musicom.

What assets should you hold in each account to minimize taxes?19 Jan 202100:37:00

#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 holdings
  • Tax-exempt bonds
  • REITS
  • Physical real estate

Check it out here:

https://hackyourwealth.com/asset-location-part-1

What asset location principles are most relevant to you? Let me know by leaving a comment.

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FIRE goal setting for the new year05 Jan 202100:12:57

#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-2021

Are you setting any FIRE related goals for 2021? What are they? Let me know by leaving a comment!

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 Intro/Outro: Old Bossa by Twin Musicom.

How to FIRE with confidence, step by step08 Dec 202001:04:10

#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 confidence
  • How to project your retirement income cash flows with clarity and confidence to match those expenses
  • How to build the investment assets needed to generate that retirement income
  • The 4 main type of investment assets for funding early retirement (and their tradeoffs)
  • How to withdraw your retirement spending needs while minimizing risk
  • How certain life milestones will impact your income and expense projections
  • Tax planning in early retirement

Check it out here:

https://hackyourwealth.com/early-retirement-fire


What 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.

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 Intro/Outro: Old Bossa by Twin Musicom.

How to pick the best index fund01 Dec 202001:04:45

#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 funds
  • Step-by-step tips for evaluating an index fund: attributes, criteria, performance indicators
  • Recommended online tools to search for and filter indexes and fund options
  • How fund expense ratios work
  • Specific names (and ticker symbols) of popular index funds for: total stock market, total bond market, government bonds, real estate, all-weather portfolio

Check it out here:

https://hackyourwealth.com/best-index-funds


What are your favorite index funds, and why? Let me know by leaving a comment.

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  Intro/Outro: Old Bossa by Twin Musicom.

How to set your target asset allocation and rebalance your portfolio efficiently24 Nov 202000:36:30

#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 underdogs
  • How to create and define your target asset allocation starting from first principles
  • How to determine your investment style and risk tolerance in an intellectually honest way
  • How to track your current allocation and analyze drift from your target
  • How to rebalance your portfolio tax-efficiently step-by-step
  • How often you should rebalance

If 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-portfolio

What 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!

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 Intro/Outro: Old Bossa by Twin Musicom.

Why writing an investment policy statement will make you a better investor17 Nov 202000:17:37

#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 future
  • Why a thoughtfully written IPS will turn you into a better investor and yield higher returns
  • How to write a good IPS
  • The 3 crucial components all good investment policy statements have
  • How often you should update your IPS
  • When to reference your IPS on a day-to-day basis

Check it out here:

https://hackyourwealth.com/investment-policy-statement

If 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.

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Section 199A: how small business owners can skip 20% of their taxes10 Nov 202001:17:18

#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 overview
  • What counts as Qualified Business Income
  • Key rules and restrictions of 199A
  • Strategies for maximizing the 199A deduction
  • How 199A might alter your retirement contribution strategy
  • Special 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 owners
  • What happens to 199A after 2025

Check it out here:

https://hackyourwealth.com/section-199a

Are 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.

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Financial independence in healthcare: how a dentist built a $7M nest egg20 Sep 202200:54:40

#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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Election day special: potential tax law changes coming?03 Nov 202000:20:31

#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 199A
  • How it could impact capital gains and qualified dividends tax rates
  • How estate taxes and the step-up in basis at death could change
  • Important changes that would affect retirement account contribution deductions
  • How 1031 exchanges for real estate investors might be impacted
  • Expected changes to the corporate tax rate

Check it out here:

https://hackyourwealth.com/biden-tax-proposal

Do 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.

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How a self-directed 401k can help you beef up retirement investing, with Dmitriy Fomichenko27 Oct 202001:08:08

#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 accounts
  • The process for setting up a self-directed retirement account, and how to fund it
  • Maintenance costs associated with self-directed accounts
  • The role of the custodian / trustee / administrator for self-directed accounts
  • How 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 treated
  • Why mixing outside funds with self-directed account funds is such a big no-no, and the consequences if you do

Check it out here:

https://hackyourwealth.com/self-directed-retirement-account-401k-IRA

Are 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.

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College financial aid tips and strategies, with Ann Garcia20 Oct 202001:20:14

#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 aid
  • The overall financial aid process, timeline, and key dates
  • The role each type of aid (need-based, merit, government, and college aid) plays in a family’s financial aid strategy
  • How FAFSA works, the 4 buckets of money that must be reported, what money can be excluded
  • What federal EFC is, how it’s calculated, and how it’s used
  • What the CSS Profile is, key differences vs. FAFSA, and what money must be reported on it
  • How CSS Profile schools calculate EFC and differences vs. FAFSA methodology
  • When it might be useful to leverage a grandparent-funded 529 plan + tradeoffs
  • Student loan options and key types of loans available to students
  • Tips for negotiating / appealing your financial aid package
  • Financial strategies related to the “prior-prior” year once January of sophomore year arrives
  • Financial strategies in the years BEFORE your child applies for college financial aid to maximize aid

Check it out here:

https://hackyourwealth.com/college-financial-aid

Has 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.

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How to get into the best colleges in America, with Shirag Shemmassian13 Oct 202000:53:11

#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 colleges
  • What elite college admissions committees are looking for, and how to differentiate yourself
  • What level/degree of accomplishment you need to get in
  • What students (and parents) can do well ahead of the application year to distinguish themselves, and how far in advance to do it
  • How lower / middle income / rural / etc students with access to fewer opportunities can still differentiate themselves compellingly
  • Why your “message” and the way you deliver it is just as important as your actual accomplishments
  • The mindset students should have when writing their college essays
  • How 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 letters
  • The qualities that make a stand-out recommendation letter

Check it out here:

https://hackyourwealth.com/college-admissions

Did 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.

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Estate planning basics: wills, trusts, power of attorney, and probate06 Oct 202001:33:28

#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 plan
  • How probate works step by step, how long it takes, and how much it costs
  • At what point in your life you should write a will
  • Differences between wills and trusts
  • Legal formalities of wills and trusts
  • How wills and trusts change the probate process
  • What DIY-ers need to know before drafting their own estate planning docs
  • Special considerations for real estate investors, family business owners, professional service practice owners, and high net-worth individuals

Check it out here:

https://hackyourwealth.com/estate-planning-basics

Do 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!

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Social Security: How it works and optimal claiming strategies29 Sep 202000:59:18

#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 calculated
  • Key factors to consider when deciding what age to claim
  • Optimal claiming strategies and tradeoffs of claiming younger vs. older
  • How 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 <20 years)
  • Whether young people should count on Social Security being there in the future as they plan their retirement finances

Check it out here:

https://hackyourwealth.com/social-security-podcast

Do you factor in future expected Social Security benefits into your retirement planning? Or do you just assume it won’t exist by the time you retire? Do you think it’s better to claim younger or older? Why? Let me know by leaving a comment when you’re done.

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How to use HSAs to avoid taxes and take charge of your healthcare, with the guy who implemented the HSA law, Roy Ramthun (aka “Mr. HSA”)22 Sep 202001:12:41

#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 work
  • Tax benefits of HSAs at both federal and state level
  • The 3 main eligibility criteria for HSAs
  • Ways to fund HSA contributions
  • What health expenses are considered qualified
  • HSA bank options and factors to consider when selecting a custodian bank
  • Reimbursement rules, receipt saving tips
  • Tips for maximizing the growth of your HSA
  • What happens to your HSA when you retire or pass away

Do 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.

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How Medicare works: eligibility, enrollment, cost, and coverage options, with Danielle Roberts15 Sep 202001:17:49

#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 requirements
  • Options for expats who haven’t paid into Medicare taxes
  • What exactly Medicare covers, how each “part” works, and premium costs
  • How to determine which doctors, hospitals, clinics, and pharmacies will accept your Medicare coverage
  • How the premium surcharge (IRMAA) works if your income exceeds certain thresholds
  • All-in costs you can expect to pay for Medicare coverage
  • How the “initial enrollment period” works, including how the penalty works
  • How Medicare Advantage works + when it’s a better choice than original Medicare (tradeoffs, considerations, cost differences, network differences)
  • How Medigap works and tradeoffs and considerations
  • How expat retirees should plan for Medicare, given it generally doesn’t cover them overseas

What 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.

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11 Essential Categories of Financial Info For Family Emergency Binders08 Sep 202000:24:40

#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 binder
  • Tips on how to organize documents, PDFs, spreadsheets, and videos
  • How often to update it + tips on staying organized
  • Why it’s worth starting now, even if it takes a long time to finish

Do 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.

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How to use whole life insurance to avoid taxes and grow wealth, with Eric Brotman01 Sep 202001:04:19

#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 insurance
  • The main tax advantages of whole life
  • How whole life is used for estate planning
  • The type of securities life insurance companies invest in
  • How to choose a whole life insurance company
  • How life insurance broker commissions work (and how much they are)
  • What paid-up additions are and why they matter
  • How to borrow against your whole life policy
  • The tradeoffs of borrowing from vs. against your policy
  • How whole life can supplement social security in retirement

If 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.

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How to pay for college23 Aug 202201:15:33

#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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How to retire early with kids (and not go broke), with Michael Quan25 Aug 202001:05:28

#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 company
  • How much he had saved up on the day he retired vs. where his portfolio is at now
  • When did kids enter the picture relative to his retirement date
  • How kids impacted the family budget, including lifestyle trade-offs they made to accommodate
  • Key areas where early retirement actually brought significant savings
  • How Michael spends his days now
  • How having kids has influenced the way he thinks about wealth building

What 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.

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How personal tragedy motivated this engineer to achieve FI and retire early, with Adam Fortuna18 Aug 202000:38:08

#44: One common trait of ordinary people who accomplish extraordinary things is their ability to turn personal struggle and tragedy into resilient energy channeled toward big goals.

And one of the most challenging tragedies ordinary people commonly face is the death of an immediate family member.

This week, I talk with Adam Fortuna, an engineer who turned his mother’s untimely death into motivation to achieve financial independence and retire early – which he did at age 36 with a portfolio >$2M.

We discuss:

  • How Adam got into software development, then transitioned into product management
  • How his mother’s premature death suddenly forced him to figure out how to manage and invest assets…and why it made him realize he wanted to retire early
  • How he applied an estimation technique used in the software development industry to come up with his FIRE number
  • Why moving states cost him 6 figures in taxes
  • How his boss reacted when he pulled the trigger and gave notice
  • How his portfolio crashed 30% when he quit his job…and why that didn’t faze him
  • Why he scrutinizes trailing averages (rather than specific months) when analyzing his safe withdrawal rate
  • How he uses the 4% rule as a heuristic, but doesn’t apply it strictly
  • How he handles health insurance post-retirement
  • The simple Google spreadsheet plugin he uses to import all his financial data into Google sheets for manual number crunching

What personal life events motivated YOU to get smart about your finances? How would a windfall impact your retirement plans? Let me know by leaving a comment when you’re done.

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Intro/Outro: Old Bossa by Twin Musicom.

What a lifetime of travel taught these early retirees over 3 decades, with Billy & Akaisha Kaderli11 Aug 202001:09:32

#43: People spend way too much time scrutinizing examples of early retirees who just recently FIRE’d and not nearly enough time on early retirees who actually made it through decades of retirement.

That’s why there’s a whole cottage industry of blogs and books by recent retirees dispensing advice (and downloadable spreadsheets) on how to save a million bucks, retire to Southeast Asia, and sip mango juice all day and get cheap massages.

But there’s nothing to actually scrutinize in these examples because no one really miscalculates their nest egg so badly that they have to go back to work within a few years.

We should spend more effort analyzing examples of people who actually successfully STAYED retired for decades. (And I don’t mean folks with $10s of millions.)

That’s because the shockingly simple math to get TO early retirement is different from the shockingly un-simple math to get THROUGH early retirement.

Yet there are few and far between examples of early retirees who actually made it through decades, weathered all the ups and downs intact, lived a good and fulfilling life, and are still in good physical and financial shape.

So you can imagine how excited I was to speak with today’s guests, a senior couple who achieved precisely this.

This week, I chat with Billy and Akaisha Kaderli, a husband wife couple who early retired 3 DECADES ago in 1991 and are still going strong. With one full 30-year retirement already behind them and a nest egg that is bigger than ever, Billy and Akaisha have traveled the world across decades, lived a great life, and have tons of stories and advice to share.

We discuss:

  • Their varied career path before retirement (French chef, stock broker)
  • Why they decided to retire early long before a FIRE community existed
  • Why they decided not to tell anyone about their early retirement plans
  • Why they defined their FIRE number based on only a subset of their expenses (and which expenses those were)
  • What they invested in before there were ETFs, and how big their portfolio was on the day they retired
  • How they planned their travels via a multi-year loop over the decades, and how they chose regional “home bases” around the world
  • When they decide to travel together vs. solo
  • How large their portfolio is now 3 decades later
  • How they afforded healthcare over the decades (including emergency surgeries) with no health insurance…and without bankrupting themselves
  • How they dealt with downturns and recessions over the decades…including the one time they briefly considered going back to get a j-o-b (and why they decided against it)
  • What they would have done differently if they could do it all over again

Does Billy and Akaisha’s story change your view on what it takes to get to FIRE? What it takes to successfully live a good and full retirement life for decades? Does it influence any choices you might make in your retirement planning plans? Let me know by leaving a comment when you’re done.

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Intro/Outro: Old Bossa by Twin Musicom.

How 2 engineers quit their jobs to retire early and travel full-time, with Kristy Shen and Bryce Leung04 Aug 202001:13:07

#42: A big reason why I started HYW was to show how you can “hack systems” in large and small ways – whether related to taxes, travel, real estate, etc – to achieve FI and retire early…

…and to continue growing wealth even in retirement.

That’s probably why many readers are engineers: you likely know a thing or two about hacking / optimizing systems.

That’s also probably why there are many ex-engineers in the FIRE community.

Today’s guests, who were engineers before early retiring, were one of the first folks in the FIRE community I started following a few years ago.

So it’s a real treat to talk with Kristy Shen and Bryce Leung, millennial early retirees who quit well-paying engineering jobs to travel the world, initially, for one year…but decided – after analyzing their spend that year and realizing it cost less to travel than to live in their hometown – to do it for good. (Along the way, they also wrote a popular FIRE blog and best-selling book.)

Their story is about applying simple rules of thumb to saving and investing to build a 7-figure portfolio and retire early, then optimizing your investments efficiently to withdraw safely into perpetuity.

We discuss:

  • What motivated them to leave well-paying engineering jobs
  • How they came up with their FIRE number and what they invested in
  • Why they rebelled against conventional wisdom to buy a home
  • How they stayed focused as friends and colleagues upgraded their lifestyles…and how they eventually became the envy of peers back home
  • Why their parents objected but eventually came around (and what convinced them)
  • The moment they realized it was cheaper to travel than to stay at home
  • How big their portfolio was on the day they retired and how big it is now (after traveling over the years)
  • How they use a “yield shield” to structure their withdrawals so they never have to sell in a down-market (and how long their cash buffer will last)
  • How their mindset shifted from “traveling to consume” to “traveling to learn”
  • How they deal with loneliness when traveling for long stretches
  • How they handle health insurance after losing their universal coverage
  • How getting older and potentially starting a family may change their travel lifestyle in the future

Would you travel long-term – potentially forever – in early retirement? Do you agree with Kristy’s and Bryce’s views on homeownership? What are your reactions to their safe withdrawal strategy (yield shield)? Let me know by leaving a comment!

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Links mentioned in this episode:

Intro/Outro: Old Bossa by Twin Musicom.

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