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Hack Your Wealth

Hack Your Wealth

Andrew Chen

Business
Business
Education

Frequency: 1 episode/14d. Total Eps: 95

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As a lawyer / engineer / MBA, how can you achieve FIRE (financial independence, retire early) rapidly to quit the rat race, pursue your passions, and live life on your own terms? Andrew Chen – founder of the Hack Your Wealth Blog and lawyer, financial expert (CFA graduate), and tech industry veteran – shows you strategies and tactics to (1) earn, (2) save, (3) invest, and (4) protect as a high earner so that you can build massive wealth and create a portfolio that’s a FIRE machine. Through solo lessons, expert interviews, and side hustle profiles, you’ll learn about tax strategies, retirement account optimization, asset allocation & rebalancing, passive income (real estate investing, side hustling, online business, digital nomading), family finances (e.g., strategizing college education costs), travel hacking, estate planning, and career transitions. Andrew podcasts about the big picture concepts, then adds step-by-step implementation guides downloadable from the Hack Your Wealth website to help you FIRE strategically, methodically, and rapidly.
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Healthcare planning = retirement planning

Episode 95

mardi 6 juin 2023 • Duration 01:14:21

#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 hotels

Episode 94

mardi 4 avril 2023 • Duration 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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Related links:

Intro/Outro: Old Bossa by Twin Musicom.

How current economic changes impact retirement safe withdrawal rates

Episode 85

mardi 11 janvier 2022 • Duration 01:49:58

#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!

Don't miss an episode, hit that subscribe button...

If you liked this episode,  subscribe so you don’t miss any upcoming episodes!

I need your help, please leave a listener review :)

If you liked this episode, would you leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

 Intro/Outro: Old Bossa by Twin Musicom.

REPLAY: How to set and rebalance your asset allocation efficiently

Episode 84

lundi 27 décembre 2021 • Duration 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!

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

 Intro/Outro: Old Bossa by Twin Musicom.

Retirement withdrawal strategies: tax-efficient portfolio drawdowns

Episode 83

mardi 2 novembre 2021 • Duration 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.


Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

I need your help, please leave a listener review :)

If you liked this episode, would you leave a quick review on Apple Podcasts? It’d mean the world to me and your review helps others find my podcast, too!

Links mentioned in this episode:

 Intro/Outro: Old Bossa by Twin Musicom.

Annuities explained: are annuities a good investment for retirement?

Episode 82

mardi 19 octobre 2021 • Duration 01:01:34

#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.

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

 Intro/Outro: Old Bossa by Twin Musicom.

Taxes on stock gains: how to avoid capital gains tax on stocks

Episode 81

mardi 5 octobre 2021 • Duration 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.

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

 Intro/Outro: Old Bossa by Twin Musicom.

Teaching your kids about money and financial independence

Episode 80

mardi 21 septembre 2021 • Duration 01:24:31

#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.

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

 Intro/Outro: Old Bossa by Twin Musicom.

College student financial aid changes coming to the FAFSA application

Episode 79

mardi 7 septembre 2021 • Duration 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.

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

 Intro/Outro: Old Bossa by Twin Musicom.

Money lessons for kids: Tips from other personal finance influencers

Episode 78

mardi 24 août 2021 • Duration 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.

 Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

 Intro/Outro: Old Bossa by Twin Musicom.

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