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Hack Your Wealth

Hack Your Wealth

Andrew Chen

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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Top 10 Hack Your Wealth Episodes

Goodpods has curated a list of the 10 best Hack Your Wealth episodes, ranked by the number of listens and likes each episode have garnered from our listeners. If you are listening to Hack Your Wealth for the first time, there's no better place to start than with one of these standout episodes. If you are a fan of the show, vote for your favorite Hack Your Wealth episode by adding your comments to the episode page.

#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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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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#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.
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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#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.

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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#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.

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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#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.

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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#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!

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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#41: Is it crazy to quit a high-paying law firm job to take a lower-paying law job (not in a law firm)?

The majority of lawyers will say no. Because that’s what most lawyers who start their careers in law firms do! Whether it’s for better hours, better balance, less travel, whatever.

Now, is it crazy to quit being a lawyer to do something completely non-law related?

Again, most lawyers will say no – because tons of lawyers do exactly that.

But: is it crazy to quit the law to...deliver for DoorDash, shop for Instacart, be a dog walker, or recharge Lime scooters?

The first time I read today’s guest’s story, I admit I thought so. Why would you seemingly throw away a promising legal career to be a manual gig laborer, when there are plenty of folks who would dream about doing the opposite?

Then I realized two things.

  1. I should be the last person to critique this because I myself “threw away” a legal career for a totally non-law path. Granted, I didn’t do it for manual labor, but it also wasn’t conventional by any means.
  2. It’s not my place (or yours or anyone’s) to judge the career choices of others. What makes people happy is their personal decision alone, and no damn business of anyone else’s!

Interviewing today’s guest for the podcast just made that even clearer.

This week, I talk with Kevin Ha, a prolific side hustle expert, about why he quit the law to pursue a unique path to financial independence. He generates income both from his blog and through side hustles (which he often blogs about), each of which separately and independently replaced his full-time salary from his last job.

We discuss:

  • Why Kevin quit the law without a traditional FIRE portfolio already in place
  • How Kevin defines financial independence
  • Why he doesn’t view gig economy side hustles as manual labor
  • How he makes side hustles fit super efficiently around his schedule to minimize time spent
  • How he structures his daytime hours now without a traditional job
  • His technique for letting go of the “prestige trap” (notorious among lawyers), despite graduating with honors (and law review) from law school
  • Whether Kevin would have gone to law school again knowing what he knows now

Do you agree with Kevin’s philosophy on FI? Even if you would not have made the same choice, do you see merit in this path? If not, 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.

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#40: Early retirement may seem glamorous when you’re dreaming about it....

Sleeping in every day. Going jogging mid-day. Picnicking on a random Tuesday. Flying off to vacation on a moment’s notice. Wandering abroad for months at a time.

But once early retirement is actually your life, it’ll feel different. You have to be intentional about it to make sure it lives up to your expectations.

This week, I invited Anita Dhake – a lawyer turned early retiree who’s retirement plan has shifted over time – to share her story about retiring from the law at 33 to travel the world, what she’s learned along the way, and why she no longer travels full-time.

We discuss:

  • Why she walked away from a high-powered law firm career after graduating from an elite law school
  • What motivated her to retire early, and how she came up with her FIRE number
  • How she tackled student debt at the same time
  • How much she had in the bank on the day she FIRE’d...and how much she has now
  • How retiring early actually made health insurance easier
  • How many countries she’s traveled to since retiring, and why long-term travel is so difficult compared to vacation travel
  • Why she ultimately stopped long-term traveling and what she’s doing now instead

Did anything in Anita’s story surprise you? Do you agree with her view on long-term travel? Would you do anything differently? Let me know by leaving a comment when you’re done.

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

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

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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#39: Everyone knows the cost of college is cray. 😖

It can create serious retirement speed bumps for parents...

...and it only gets worse with every passing year. 📈

But for students and parents who are super on top of their 💩, there is a real path – through scholarships and fellowships – to make the cost of college (and grad school) FREE.

Not only that, if you’re really good and write superb applications, you can even get PAID to attend.

They say, “There’s tons of free money out there for college; you just have to know where to look.”

Well, so...where’s all that free money? And how can you get it?

This week, I talk in-depth with Shirag Shemmassian, PhD, about the exact tips and tactics you need to win scholarships hand over fist, so that you can attend college and grad school for free...or even get paid to attend.

Shirag is a university admissions expert and founder of Shemmassian Academic Consulting, where he has helped students win admission to every elite college in the country.

As someone who himself won over $200k in scholarships, Shirag’s insights are pure gold, so for you neurotic parents out there, this is an episode you won’t want to miss.

What you’ll learn:

  • The biggest myths and misconceptions when it comes to winning scholarships
  • The 4 key places to find scholarships and the pros and cons of each
  • How to write a superb scholarship application (and do it super efficiently again and again)
  • How to ask for standout recommendation letters
  • How the game up-levels (and differs) for the most prestigious and competitive scholarships in the world (Coca-Cola, Gates, Goldwater, Rhodes, Marshall, Soros, Fulbright, Truman)
  • How to prepare for interviews with these scholarship selection committees

What tips / advice resonate most? If you’re a parent of a successful scholarship student, what other tips did you find effective for winning scholarships? Let me know by leaving a comment when you’re done.

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

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

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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#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.
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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FAQ

How many episodes does Hack Your Wealth have?

Hack Your Wealth currently has 95 episodes available.

What topics does Hack Your Wealth cover?

The podcast is about Financial Independence, Career, Real Estate, Entrepreneurship, Investing, Family, Podcasts, Fire and Business.

What is the most popular episode on Hack Your Wealth?

The episode title 'Social Security: How it works and optimal claiming strategies' is the most popular.

What is the average episode length on Hack Your Wealth?

The average episode length on Hack Your Wealth is 52 minutes.

How often are episodes of Hack Your Wealth released?

Episodes of Hack Your Wealth are typically released every 7 days.

When was the first episode of Hack Your Wealth?

The first episode of Hack Your Wealth was released on Oct 30, 2019.

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