June 30, 2025 • 19 mins
What if work became a choice, not a requirement?
The Early Retirement Podcast is here to help you navigate the path to financial independence, so you can retire when you want and live how you want. Whether you’re nearing retirement or just starting to plan, this podcast delivers clear, actionable insights designed to simplify your biggest financial decisions.
We focus on strategies that make a real impact—from tax planning moves that may unlock $100,000+ in lifetime savings, to investment and withdrawal strategies that align with your values and goals. It's not about chasing perfection, it's about creating a plan that gives you freedom, clarity, and peace of mind.
Because at the end of the day, early retirement isn’t just about leaving your job, it’s about building a life you don’t want to escape from.
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Advisory services are offered through Root Financial Partners, LLC, an SEC-registered investment adviser. This content is intended for informational and educational purposes only and should not be considered personalized investment, tax, or legal advice. Viewing this content does not create an advisory relationship. We do not provide tax preparation or legal services. Always consult an investment, tax or legal professional regarding your specific situation.
The strategies, case studies, and examples discussed may not be suitable for everyone. They are hypothetical and for illustrative and educational purposes only. They do not reflect actual client results and are not guarantees of future performance. All investments involve risk, including the potential loss of principal.
Comments reflect the views of individual users and do not necessarily represent the views of Root Financial. They are not verified, may not be accurate, and should not be considered testimonials or endorsements
Participation in the Retirement Planning Academy or Early Retirement Academy does not create an advisory relationship with Root Financial. These programs are educational in nature and are not a substitute for personalized financial advice. Advisory services are offered only under a written agreement with Root Financial.
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Ari Taublieb, CFP ®, MBA is the Chief Growth Officer of Root Financial Partners and a Fiduciary Financial Planner specializing in helping clients retire early with confidence.
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Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
The Early Retirement Podcast started in December of
2020.
We are now, as of thisrecording, in June of 2025.
We're nearly five years.
We're about four and a halfyears.
This is an episode where I'mgonna tell you about the history
of the show, a little bit moreabout who I am.
If you already know all of thisbecause you've been listening
for years, you don't need tolisten to this episode.
(00:22):
If you want an overview, ifyou're new awesome, I hope you
tune in, regardless If you watchmy YouTube videos or not.
Everything I talk about is forone sole goal I want you to know
the earliest time working isoptional, where you're working
because you want to, not becauseyou have to.
That is the biggest thing thatI talk about and try to come
(00:44):
across.
Now, everything I do is forthis idea that if you could
spend more time with family, oryou could spend more time
traveling or just on a newcareer, and if you're smart with
numbers, you can get more ofthat.
I mean, how cool is this?
I'm not obsessed with Rothconversions.
I'm not obsessed with acharitable trust.
I'm obsessed with the fact thatI'm not obsessed with a
(01:05):
charitable trust.
I'm obsessed with the fact that, if you use these things well,
you can get more time doing whatyou want to do.
That's why numbers are sofascinating to me.
You're all humans.
You're not robots.
I have so many differentexamples.
I've told the story of my dadmany times.
My dad saved and invested verypoorly, but he made a ton of
money.
He had a great life.
(01:26):
He paid for so many things.
I'm so grateful.
The reason I have theconfidence I do today is he paid
for so many things, so manyprivate lessons along the way.
I'm so grateful.
But my dad has concentratedstock.
He bought Monster Stock andit's done so well for him.
Stock, and it's done so wellfor him.
(01:46):
But I said, dad, do you wantthat one company to dictate how
many surf trips you take inretirement?
He's like no way.
So I should diversify.
I said don't just diversifyblindly, do it over time to
minimize tax consequences, butalso recognize that if there's
something that we're seeing thatmay make you lose sleep, for
example, every time monsterstock goes down, my dad, he has
a notification on his phone.
Okay, so his neck starts tohurt sometimes and I go dad, you
(02:09):
want your neck to hurt?
Now, that's impacting surfing.
What's the real risk of holdingthis monster stock.
It's going beyond just okay,the emotional, you know ups and
downs.
It's now taking up so much ofyour time and it's is it worth
the hassle?
What if we diversified it?
What if we did sell?
(02:32):
What if we did pay this taxbill?
Would that be worth it?
So I use my parents as examplesall the time.
I currently am a financialplanner.
I'm a certified financialplanner because my parents were
burned by four advisors Now, notburned, as in, their money was
stolen.
So burned might be the wrongword, but they had many
different advisors and myparents great at making money.
They needed good guidance.
They didn't receive good taxplanning guidance.
(02:53):
There were conflicts ofinterest.
They were sold products theyshouldn't have, in my opinion.
Now this show you're listeningto right now the early
retirement show this was not theoriginal name.
Over six years ago, I wasworking in a company called
Nuveen.
Nuveen is this big companyfocusing on tax-free income,
municipal bonds specifically.
(03:15):
So here I am, learning abouttax-free income and optimizing
taxes and all this stuff, and Ijust didn't love it because
we're only working with thesebig institutions.
I didn't find a ton of value, Ididn't feel I was making a
difference, and so I eventuallyconnected with James.
James is the founder of Root.
I was the first employee tojoin this company, root
Financial.
Now we have over 50 teammembers as of today, and we get
(03:39):
to help hundreds of clientsoptimize their finances where we
work directly with them.
Help hundreds of clientsoptimize their finances where we
work directly with them.
What's also really cool isthere are hundreds of thousands
of you and millions thatactually watch, listen to our
content every month who don'twork with Root that hopefully
still receive tremendous value.
So our way of giving back ismaking all this content for free
.
(04:00):
Now, if you're listening on thepodcast app, no ads.
If you're on YouTube, I knowthere are ads.
You can pay for YouTube Premium.
I pay personally for YouTubePremium in my life.
It is an investment.
I found that's worth making,although my fiancee says that I
should not have paid for itbecause now I watch too much
YouTube.
But beside the point, the pointof this episode is to tell you
(04:20):
this podcast specifically.
You're never going to see memake an episode.
Here's the best new credit cardof 2025, or I'm going to show
you how to travel.
Hack with these points and makesure to open a card and then
get rid of it after three monthsand then reinstall a different
card and then have yourneighbor's dog get a new card.
That is not my style.
Okay, that is not what lightsme up and I don't feel that adds
(04:42):
tremendous value.
Now there are people that talkabout those things and I'm not
saying those people are terrible.
I'm just saying what lights meup, what really moves the needle
in big ways, is helping youunderstand.
Hey, should I be maxing out my401k because I've done it for 30
years, or should I maybe onlyput enough money to get the free
match, because I love freemoney, and divert the rest to,
(05:04):
maybe, a superhero account wherenow I have more flexibility
around the funds?
Maybe I should considerretiring early because of
healthcare I normally neverwould have, but now I see with
this superhero account I canmassage my income.
Guys, these are things that canmake big differences in your
lives where, if I can give yousome actual, actionable insight,
you might be able to retirefive years earlier and if you
(05:27):
get five years earlier with yourfamily.
You can't exactly quantify thaton some spreadsheet, although
I've tried doing stuff like thatbecause I'm an Excel weirdo.
My point here.
I love what I get to do.
Many of you know my joking kindof style.
I do not do that to be annoying.
I hope my stories don't feelannoying in any capacity.
I do this because I had a mentoronce who told me, ari, if you
(05:48):
do not keep people laughing, nomatter what point you're trying
to get across, it will notmatter.
And I challenged him and I saidI don't think so.
I think if I can clearly makesure my point resonates and give
an example, they're going totake away what I need them to
take away.
And he laughed and said that'sso cute, you haven't been in the
business long enough.
And I then had him show medifferent examples and I could
(06:12):
see through different studiesthat he was showing me but also
the way he was explaining it.
I went look, I think you have apoint here and it's hard,
because I'm a human, to say I'mwrong.
I was 100% wrong.
I'm seeing him givepresentations and I thought he
was spitting out gold because Ilove this stuff.
He was saying Ari, there's aspouse who maybe never had a
(06:32):
lemonade stand, who probably hasnever heard of a 401k.
The people listening to yourpodcast, they probably love this
stuff.
They want to optimize.
That's why they're listening.
What about that spouse whotraditionally is not involved?
Are you going to make surethey're completely ignored?
How do you get them interested?
What questions could you askthem that make them feel heard
for the first time in their liferegarding their finances?
(06:53):
I went that's a powerfulquestion.
So I do different jokes.
I try to keep it entertaining.
I need to educate, because thisis what lets me sleep at night.
I will wake up and go.
There's a point I want to getacross.
If nobody hears it or nobodyleaves a comment or sends me an
email, that's okay.
I sleep better knowing youheard it.
Do I love getting to hear whenit's helpful?
(07:13):
Yes, because it helps me makedifferent types of content for
you guys.
But coming up on five years ofthis podcast, I have no
intention to stop.
I eventually want to ramp upwhat I'm doing.
I want to have more guests.
I very rarely have guests onbecause I want to do it in my
style, and when I bring a gueston, sometimes you guys have
(07:34):
shared with me.
Hey, ari, it was good, but thatperson that didn't feel like it
was my exact example.
I found it was a 30-minuteepisode that I kind of prefer
your 10 to 15-minute style.
So I'll do different versionsand test it out always.
But I would love to ramp it upRight now.
On YouTube I'm posting almostevery single day, about six days
(07:54):
a week.
As of today, I am showing youdifferent case studies.
I'm going into differentexamples on how to think about.
What are these big levers?
What if you retire and getunlucky?
You might have head trash.
Right now, head trash is one ofthese phrases I talk about
where you might think there's noway I can retire early.
I mean, healthcare is going tocost so much and my friends,
they're nowhere close toretiring, they're not even
(08:15):
talking about it.
So why on earth am I evendebating this?
Am I just being dumb?
No, you're not being dumb.
You might be really smart andthey might not be considering it
.
There's a joke within my friendgroup and at the company here,
but within the friend group mynickname is the initiator.
I'm the one that initiates.
Guys, we're taking a trip.
I just paid for it upfront.
Please pay me back.
Here's why we're going to go.
(08:36):
I miss you guys If I don't makethat action.
What happens is we don't go onthe trips.
Someone might argue okay, wellthen, your friends aren't that
good of friends or whatever.
From the outside, it could looklike that.
That's not the case.
They're just not initiators.
Someone's got to do it, and Idon't mind doing it.
Would I like it if all of ustalked more about?
Hey, let's do it as a team, ofcourse.
(08:57):
But that's not the case.
Everyone in a relationship haspros and cons, once again, in a
romantic and non-romanticrelationship.
Now, at the same time, wheneverI'm thinking about okay, how
can I deliver a certain point?
What can I do that's going tomake this resonate, I'm thinking
of analogies, I'm thinking ofstories.
I've told this one often, butand I think I even told it in
(09:18):
last week's episode but I wentto a doctor this was a long time
ago now, maybe a year and Itold the doc what you just said
there.
I think you believe it soundedgreat.
I really think you thought ithit home and it sounded good.
But I'm really sorry, I don'tknow what you just said, so
would you try again?
And I will say it thattransparently.
And then he said I'm so sorry.
Yeah, let me explain again.
(09:39):
So he starts explaining to methe lab that the pills are made
in that he wants to give me.
And I said look, I'm reallysorry, but I don't want to be
difficult here.
I don't care about the lab, Ijust need to know why I'm going
to take this pill or why I'm notgoing to take this pill, and
I'm not going to take it blindly.
So I'm not trying to bedifficult.
I don't want to be one of thoseclients, but I do want to make
sure I'm taking this, knowing Ican sleep at night.
(10:00):
So he said oh, I'm sorry, Ididn't know.
You didn't want that muchdetail.
So then he did a beautiful jobexplaining it.
I said, doc, you did it.
I'm now fully clear.
Oh, I'm taking the supplement.
That's how you should beworking with your advisor.
(10:21):
I believe if you have an advisor, you should be able to ask them
these questions and go hey, I'mreally sorry.
I know you seem excited andthat says green and not red and
I should do the green thing, butI'm just not clear on it.
We will ask a spouse who'straditionally never had any
interest in financial planningit.
We will ask a spouse who'straditionally never had any
interest in financial planningIf we force you to spend
(10:43):
$100,000 this year and if youdon't, you can't save it.
It's going to your leastfavorite political party.
What would you do?
That gets people to open up.
Okay, we try to keep itcreative here.
Some people go Ari, my spousewould have no issue spending
more money.
It's how do we save more moneyso we can retire early?
Great, different story here.
But everything I do is withthis concept of an early
retirement.
There's nothing magical aboutearly retirement.
(11:04):
Early retirement to me is areyou working because you want to
or because you have to?
As I see it, I am in an earlyretirement, yet I don't have
enough money to never work everagain.
I just love my work so much.
If you told me that I wouldhave to pay to do my job, I
would.
I love what I get to do.
Some of you go that's awesome.
(11:25):
I don't feel that way.
When can I retire?
Beautiful, hopefully.
The tax strategies I talk aboutthe big ones, guys.
I talk about tax gainharvesting.
That's how do you pay 0% intaxes when you retire early?
Many of you are not even awarethat you could create $120,000
of tax-free income.
That is an available option toyou today.
So would you rather work andmake $200,000 a year and net
(11:52):
after 401ks and insurance andtaxes.
Would you rather net let's callit 160 on that?
Or would you rather do nothingat all and generate $120,000
tax-free?
Do whatever you want?
Well, that might be moreattractive.
Now, that option is onlyavailable with a superhero
account, a reason I preach onthis once again, I don't get any
commissions on whether you useone account over another.
I just want you to make themost money.
(12:13):
So, superhero accounts I talkabout Roth conversions.
This can add hundreds ofthousands of dollars potentially
more, potentially less over thecourse of your retirement.
Many of you listening, you'vesaved really well, but you've
saved to a 401k.
You've saved to an IRA thathelps you.
Today, you get a tax deductionOver the future.
You're going to eventually haveto pay taxes on that.
(12:34):
Many of you have a lot of moneyin a single stock.
You just sold your company.
You have $12 million.
You're like, hey, should Ideploy this all at once?
What about my children?
I don't want them to inherit itand now they figure I don't
need to work hard.
I don't want to create a burden.
I also don't want to leavemoney on the table.
I don't want to be so unoptimalthat I'm actually looking back
(12:56):
at my life going, hey, whydidn't I spend more money?
So there is a balance, ofcourse, like with anything, but
this podcast is designed to helpyou understand and ensure
you're not leaving money on thetable unnecessarily.
I talk about a lot of differentstrategies healthcare insurance,
estate planning, withdrawalplanning.
(13:18):
Withdrawal planning is sounderrated.
Tax strategy I have all myanalogies.
I have my retirement boxer,where I want you to be dynamic
throughout retirement.
I talk about cauliflower.
Can we eat a little bit ofcauliflower, pay a little bit in
taxes today to avoid eating aton of cauliflower in the future
, when you're gonna want thesteak and you're gonna want the
pasta and you're gonna want thegood stuff?
How do we understand thatbalance?
(13:40):
How can we go deeper andactually understand this concept
of recreational employment?
Am I working today because Iwant to or because I have to?
This podcast is designed to helpyou retire early.
If I've helped you already inany capacity and you're watching
on YouTube, please like thisvideo and comment below what
I've helped with, because I lovegetting to hear from you guys.
(14:00):
If you're listening on thepodcast app, shoot me a note.
There's not a comment section.
You can email me at ari, atrootfinancialcom.
You can say, hey, this reallyhelped.
I'm now feeling this way.
You could say you know what.
I would love for you to go intomore detail on the tax strategy.
You used to do it more.
Now I want updated brackets.
I want to go into healthcare.
I want more examples.
(14:21):
Should I prioritize healthcaresubsidies?
Should I do Roth conversions?
What if I'm projected to leave5 million to my heirs?
What can I do Roth conversions?
What if I'm projected to leave5 million to my heirs?
What can I do to minimize that?
Or should I just not even beworrying about that?
Should I try to spend moremoney?
One of the biggest things thatyou guys have told me that I've
helped you with is I talk aboutRoth conversions a lot because a
lot of you have saved well to a401k.
(14:44):
You're not getting great taxstrategy from other aspects of
your life, from your currentadvisor, and you've learned
there's value to eating a littlecauliflower today to avoid
eating a lot in the future.
But you know what a big mistakea lot of you make is.
You create this beautiful Rothconversion strategy and you can
see if I convert to this bracketfor this amount of years and
pay taxes today.
It could yield hundreds ofthousands of tax savings in the
(15:06):
future, but you know what youshould do instead.
Yield hundreds of thousands oftax savings in the future, but
you know what you should doinstead.
You might actually enjoy yourlife more by retiring earlier,
by spending more money.
No one has ever come to me at 85going, ari, I'm just so glad I
had the best Roth conversionstrategy.
I have had people go.
I'm really glad I spent moremoney and helped my kid get that
down payment.
I'm really glad I retired fiveyears earlier because I got
(15:29):
trips that I could never getback because my health took a
big shift at 65.
Awesome, those are realpowerful stories.
So it's easy to get lost inthis.
It's easy to go.
Oh my gosh, ari, you have 300episodes on insurance and tax
and estate.
Oh my gosh, how am I going toever get through this?
Am I ever going to retire early?
No, the reason that I do thisis so people like yourselves who
(15:51):
save and invest well, reach outand find that when you find
it's time to have a partner, soyou don't have to have your
full-time job in retirementdoing this.
That's what we do here at Root.
Many of you, though, are in your30s or 40s and you want to
retire early, and I'm the weirdadvisor that says you shouldn't
pay us yet.
It doesn't make sense to, wecan't add value, it's not the
(16:12):
right time.
Keep saving and investing, butmaybe tweak some of these things
, giving you some insight, sowhen it does come time in the
future, you might find that thisis what you want to do.
I have people reach out who goAri, I love this.
When I retire, I'm going toread tax law.
This when I retire, I'm goingto read tax law.
I want to be the one runningthese projections.
And my spouse, I want them todo it too.
(16:34):
Okay, I don't hear that toooften, but there are people who
say that I say great, then don'tpay me, it would not make sense
.
Other people go no, I see thevalue because I want to spend my
time doing what I want, and Iwant to have a professional, a
third party.
I want to make sure, ifsomething happens, my spouse is
taken care of.
I want to delegate and have apartner, because I find value in
it, but it's not an all fitsone model.
(16:55):
One size fits all, should I saythe reason what makes Root Root
and me me is we're adding thistax strategy component that's so
often lost.
I cannot tell you how manytimes people have said I go ask
my advisor a tax question, theytell me to talk to my CPA.
My, you know.
I go ask my advisor a taxquestion, they tell me to talk
to my CPA.
My CPA says talk to my advisor.
My advisors has talked to myinsurance agent.
Here I am playing middleman or acoordinator role for retirement
(17:18):
.
That's not what this issupposed to look like.
You're supposed to have apartner, someone who is helping
with every step along the way soyou can enjoy what you've
worked so hard for.
Now there is an option that Italk about often in the episodes
that I record of this EarlyRetirement Academy.
That is really designed to giveyou a gut check.
There's not specificrecommendations.
(17:39):
That's a great option if youwant to go be your own advisor.
Build your own plan, run yourown scenario, see what am I on
track for.
How early could I actuallyretire?
What if it turns out?
My inflation assumption shouldbe lower.
What if it turns out?
You name it.
You can go play around.
It's a good gut check.
What it doesn't do is itdoesn't add in that layer of
(18:00):
peace of mind, of confidence, ofproactive planning.
It's not going to say, hey guys, while you're traveling, you
should have executed aconversion.
And here's the healthcaresubsidy that we're going to now
shift and, by the way, we'regoing to do a charitable
strategy because you didn't saveit, you didn't spend enough
money.
You told us you wanted to takesix trips.
You took four.
These are the real reasonspeople work with Root.
This podcast, though, isdesigned to educate you.
(18:22):
I hope it's entertaining alongthe way.
Just want to give you somebackstory on this podcast, why I
do what I do today, and I hopethat this was helpful.
I'll see you guys next week,back to our normal episodes.
Thank you all, as always, forlistening to the Early
Retirement Podcast.
I love getting to host theseshows and make different content
for you guys every single week.
(18:43):
I've not missed a single weekin years, and that is because I
love getting to do this.
Now, please be smart about this.
Before you actually execute anystrategy that you see me talk
about or hear me talk about,should I say Please talk to your
financial advisor, your taxpreparer, your estate attorney.
Please be smart about this.
None of this should beconstrued as financial advice.
(19:04):
This is for fun, educational,informational purposes only.
Once again, just quickdisclaimer here.
Guys, please be smart aboutthis.
Appreciate you listening, asalways, and you can, of course,
submit a question on my website,earlyretirementpodcastcom, if
you, of course, want me toaddress a specific case study or
topic.
I will not promise I can get toit, but I respond to every
(19:27):
single person and if I find itwill be helpful for a lot of
people, I will absolutely makean episode on it, at the very
least give you some insight.
That's it, thanks, guys.
The Early Retirement Podcast started in December of
2020.
We are now, as of thisrecording, in June of 2025.
We're nearly five years.
We're about four and a halfyears.
This is an episode where I'mgonna tell you about the history
of the show, a little bit moreabout who I am.
If you already know all of thisbecause you've been listening
for years, you don't need tolisten to this episode.
(00:22):
If you want an overview, ifyou're new awesome, I hope you
tune in, regardless If you watchmy YouTube videos or not.
Everything I talk about is forone sole goal I want you to know
the earliest time working isoptional, where you're working
because you want to, not becauseyou have to.
That is the biggest thing thatI talk about and try to come
(00:44):
across.
Now, everything I do is forthis idea that if you could
spend more time with family, oryou could spend more time
traveling or just on a newcareer, and if you're smart with
numbers, you can get more ofthat.
I mean, how cool is this?
I'm not obsessed with Rothconversions.
I'm not obsessed with acharitable trust.
I'm obsessed with the fact thatI'm not obsessed with a
(01:05):
charitable trust.
I'm obsessed with the fact that, if you use these things well,
you can get more time doing whatyou want to do.
That's why numbers are sofascinating to me.
You're all humans.
You're not robots.
I have so many differentexamples.
I've told the story of my dadmany times.
My dad saved and invested verypoorly, but he made a ton of
money.
He had a great life.
(01:26):
He paid for so many things.
I'm so grateful.
The reason I have theconfidence I do today is he paid
for so many things, so manyprivate lessons along the way.
I'm so grateful.
But my dad has concentratedstock.
He bought Monster Stock andit's done so well for him.
Stock, and it's done so wellfor him.
(01:46):
But I said, dad, do you wantthat one company to dictate how
many surf trips you take inretirement?
He's like no way.
So I should diversify.
I said don't just diversifyblindly, do it over time to
minimize tax consequences, butalso recognize that if there's
something that we're seeing thatmay make you lose sleep, for
example, every time monsterstock goes down, my dad, he has
a notification on his phone.
Okay, so his neck starts tohurt sometimes and I go dad, you
(02:09):
want your neck to hurt?
Now, that's impacting surfing.
What's the real risk of holdingthis monster stock.
It's going beyond just okay,the emotional, you know ups and
downs.
It's now taking up so much ofyour time and it's is it worth
the hassle?
What if we diversified it?
What if we did sell?
(02:32):
What if we did pay this taxbill?
Would that be worth it?
So I use my parents as examplesall the time.
I currently am a financialplanner.
I'm a certified financialplanner because my parents were
burned by four advisors Now, notburned, as in, their money was
stolen.
So burned might be the wrongword, but they had many
different advisors and myparents great at making money.
They needed good guidance.
They didn't receive good taxplanning guidance.
(02:53):
There were conflicts ofinterest.
They were sold products theyshouldn't have, in my opinion.
Now this show you're listeningto right now the early
retirement show this was not theoriginal name.
Over six years ago, I wasworking in a company called
Nuveen.
Nuveen is this big companyfocusing on tax-free income,
municipal bonds specifically.
(03:15):
So here I am, learning abouttax-free income and optimizing
taxes and all this stuff, and Ijust didn't love it because
we're only working with thesebig institutions.
I didn't find a ton of value, Ididn't feel I was making a
difference, and so I eventuallyconnected with James.
James is the founder of Root.
I was the first employee tojoin this company, root
Financial.
Now we have over 50 teammembers as of today, and we get
(03:39):
to help hundreds of clientsoptimize their finances where we
work directly with them.
Help hundreds of clientsoptimize their finances where we
work directly with them.
What's also really cool isthere are hundreds of thousands
of you and millions thatactually watch, listen to our
content every month who don'twork with Root that hopefully
still receive tremendous value.
So our way of giving back ismaking all this content for free
.
(04:00):
Now, if you're listening on thepodcast app, no ads.
If you're on YouTube, I knowthere are ads.
You can pay for YouTube Premium.
I pay personally for YouTubePremium in my life.
It is an investment.
I found that's worth making,although my fiancee says that I
should not have paid for itbecause now I watch too much
YouTube.
But beside the point, the pointof this episode is to tell you
(04:20):
this podcast specifically.
You're never going to see memake an episode.
Here's the best new credit cardof 2025, or I'm going to show
you how to travel.
Hack with these points and makesure to open a card and then
get rid of it after three monthsand then reinstall a different
card and then have yourneighbor's dog get a new card.
That is not my style.
Okay, that is not what lightsme up and I don't feel that adds
(04:42):
tremendous value.
Now there are people that talkabout those things and I'm not
saying those people are terrible.
I'm just saying what lights meup, what really moves the needle
in big ways, is helping youunderstand.
Hey, should I be maxing out my401k because I've done it for 30
years, or should I maybe onlyput enough money to get the free
match, because I love freemoney, and divert the rest to,
(05:04):
maybe, a superhero account wherenow I have more flexibility
around the funds?
Maybe I should considerretiring early because of
healthcare I normally neverwould have, but now I see with
this superhero account I canmassage my income.
Guys, these are things that canmake big differences in your
lives where, if I can give yousome actual, actionable insight,
you might be able to retirefive years earlier and if you
(05:27):
get five years earlier with yourfamily.
You can't exactly quantify thaton some spreadsheet, although
I've tried doing stuff like thatbecause I'm an Excel weirdo.
My point here.
I love what I get to do.
Many of you know my joking kindof style.
I do not do that to be annoying.
I hope my stories don't feelannoying in any capacity.
I do this because I had a mentoronce who told me, ari, if you
(05:48):
do not keep people laughing, nomatter what point you're trying
to get across, it will notmatter.
And I challenged him and I saidI don't think so.
I think if I can clearly makesure my point resonates and give
an example, they're going totake away what I need them to
take away.
And he laughed and said that'sso cute, you haven't been in the
business long enough.
And I then had him show medifferent examples and I could
(06:12):
see through different studiesthat he was showing me but also
the way he was explaining it.
I went look, I think you have apoint here and it's hard,
because I'm a human, to say I'mwrong.
I was 100% wrong.
I'm seeing him givepresentations and I thought he
was spitting out gold because Ilove this stuff.
He was saying Ari, there's aspouse who maybe never had a
(06:32):
lemonade stand, who probably hasnever heard of a 401k.
The people listening to yourpodcast, they probably love this
stuff.
They want to optimize.
That's why they're listening.
What about that spouse whotraditionally is not involved?
Are you going to make surethey're completely ignored?
How do you get them interested?
What questions could you askthem that make them feel heard
for the first time in their liferegarding their finances?
(06:53):
I went that's a powerfulquestion.
So I do different jokes.
I try to keep it entertaining.
I need to educate, because thisis what lets me sleep at night.
I will wake up and go.
There's a point I want to getacross.
If nobody hears it or nobodyleaves a comment or sends me an
email, that's okay.
I sleep better knowing youheard it.
Do I love getting to hear whenit's helpful?
(07:13):
Yes, because it helps me makedifferent types of content for
you guys.
But coming up on five years ofthis podcast, I have no
intention to stop.
I eventually want to ramp upwhat I'm doing.
I want to have more guests.
I very rarely have guests onbecause I want to do it in my
style, and when I bring a gueston, sometimes you guys have
(07:34):
shared with me.
Hey, ari, it was good, but thatperson that didn't feel like it
was my exact example.
I found it was a 30-minuteepisode that I kind of prefer
your 10 to 15-minute style.
So I'll do different versionsand test it out always.
But I would love to ramp it upRight now.
On YouTube I'm posting almostevery single day, about six days
(07:54):
a week.
As of today, I am showing youdifferent case studies.
I'm going into differentexamples on how to think about.
What are these big levers?
What if you retire and getunlucky?
You might have head trash.
Right now, head trash is one ofthese phrases I talk about
where you might think there's noway I can retire early.
I mean, healthcare is going tocost so much and my friends,
they're nowhere close toretiring, they're not even
(08:15):
talking about it.
So why on earth am I evendebating this?
Am I just being dumb?
No, you're not being dumb.
You might be really smart andthey might not be considering it
.
There's a joke within my friendgroup and at the company here,
but within the friend group mynickname is the initiator.
I'm the one that initiates.
Guys, we're taking a trip.
I just paid for it upfront.
Please pay me back.
Here's why we're going to go.
(08:36):
I miss you guys If I don't makethat action.
What happens is we don't go onthe trips.
Someone might argue okay, wellthen, your friends aren't that
good of friends or whatever.
From the outside, it could looklike that.
That's not the case.
They're just not initiators.
Someone's got to do it, and Idon't mind doing it.
Would I like it if all of ustalked more about?
Hey, let's do it as a team, ofcourse.
(08:57):
But that's not the case.
Everyone in a relationship haspros and cons, once again, in a
romantic and non-romanticrelationship.
Now, at the same time, wheneverI'm thinking about okay, how
can I deliver a certain point?
What can I do that's going tomake this resonate, I'm thinking
of analogies, I'm thinking ofstories.
I've told this one often, butand I think I even told it in
(09:18):
last week's episode but I wentto a doctor this was a long time
ago now, maybe a year and Itold the doc what you just said
there.
I think you believe it soundedgreat.
I really think you thought ithit home and it sounded good.
But I'm really sorry, I don'tknow what you just said, so
would you try again?
And I will say it thattransparently.
And then he said I'm so sorry.
Yeah, let me explain again.
(09:39):
So he starts explaining to methe lab that the pills are made
in that he wants to give me.
And I said look, I'm reallysorry, but I don't want to be
difficult here.
I don't care about the lab, Ijust need to know why I'm going
to take this pill or why I'm notgoing to take this pill, and
I'm not going to take it blindly.
So I'm not trying to bedifficult.
I don't want to be one of thoseclients, but I do want to make
sure I'm taking this, knowing Ican sleep at night.
(10:00):
So he said oh, I'm sorry, Ididn't know.
You didn't want that muchdetail.
So then he did a beautiful jobexplaining it.
I said, doc, you did it.
I'm now fully clear.
Oh, I'm taking the supplement.
That's how you should beworking with your advisor.
(10:21):
I believe if you have an advisor, you should be able to ask them
these questions and go hey, I'mreally sorry.
I know you seem excited andthat says green and not red and
I should do the green thing, butI'm just not clear on it.
We will ask a spouse who'straditionally never had any
interest in financial planningit.
We will ask a spouse who'straditionally never had any
interest in financial planningIf we force you to spend
(10:43):
$100,000 this year and if youdon't, you can't save it.
It's going to your leastfavorite political party.
What would you do?
That gets people to open up.
Okay, we try to keep itcreative here.
Some people go Ari, my spousewould have no issue spending
more money.
It's how do we save more moneyso we can retire early?
Great, different story here.
But everything I do is withthis concept of an early
retirement.
There's nothing magical aboutearly retirement.
(11:04):
Early retirement to me is areyou working because you want to
or because you have to?
As I see it, I am in an earlyretirement, yet I don't have
enough money to never work everagain.
I just love my work so much.
If you told me that I wouldhave to pay to do my job, I
would.
I love what I get to do.
Some of you go that's awesome.
(11:25):
I don't feel that way.
When can I retire?
Beautiful, hopefully.
The tax strategies I talk aboutthe big ones, guys.
I talk about tax gainharvesting.
That's how do you pay 0% intaxes when you retire early?
Many of you are not even awarethat you could create $120,000
of tax-free income.
That is an available option toyou today.
So would you rather work andmake $200,000 a year and net
(11:52):
after 401ks and insurance andtaxes.
Would you rather net let's callit 160 on that?
Or would you rather do nothingat all and generate $120,000
tax-free?
Do whatever you want?
Well, that might be moreattractive.
Now, that option is onlyavailable with a superhero
account, a reason I preach onthis once again, I don't get any
commissions on whether you useone account over another.
I just want you to make themost money.
(12:13):
So, superhero accounts I talkabout Roth conversions.
This can add hundreds ofthousands of dollars potentially
more, potentially less over thecourse of your retirement.
Many of you listening, you'vesaved really well, but you've
saved to a 401k.
You've saved to an IRA thathelps you.
Today, you get a tax deductionOver the future.
You're going to eventually haveto pay taxes on that.
(12:34):
Many of you have a lot of moneyin a single stock.
You just sold your company.
You have $12 million.
You're like, hey, should Ideploy this all at once?
What about my children?
I don't want them to inherit itand now they figure I don't
need to work hard.
I don't want to create a burden.
I also don't want to leavemoney on the table.
I don't want to be so unoptimalthat I'm actually looking back
(12:56):
at my life going, hey, whydidn't I spend more money?
So there is a balance, ofcourse, like with anything, but
this podcast is designed to helpyou understand and ensure
you're not leaving money on thetable unnecessarily.
I talk about a lot of differentstrategies healthcare insurance,
estate planning, withdrawalplanning.
(13:18):
Withdrawal planning is sounderrated.
Tax strategy I have all myanalogies.
I have my retirement boxer,where I want you to be dynamic
throughout retirement.
I talk about cauliflower.
Can we eat a little bit ofcauliflower, pay a little bit in
taxes today to avoid eating aton of cauliflower in the future
, when you're gonna want thesteak and you're gonna want the
pasta and you're gonna want thegood stuff?
How do we understand thatbalance?
(13:40):
How can we go deeper andactually understand this concept
of recreational employment?
Am I working today because Iwant to or because I have to?
This podcast is designed to helpyou retire early.
If I've helped you already inany capacity and you're watching
on YouTube, please like thisvideo and comment below what
I've helped with, because I lovegetting to hear from you guys.
(14:00):
If you're listening on thepodcast app, shoot me a note.
There's not a comment section.
You can email me at ari, atrootfinancialcom.
You can say, hey, this reallyhelped.
I'm now feeling this way.
You could say you know what.
I would love for you to go intomore detail on the tax strategy.
You used to do it more.
Now I want updated brackets.
I want to go into healthcare.
I want more examples.
(14:21):
Should I prioritize healthcaresubsidies?
Should I do Roth conversions?
What if I'm projected to leave5 million to my heirs?
What can I do Roth conversions?
What if I'm projected to leave5 million to my heirs?
What can I do to minimize that?
Or should I just not even beworrying about that?
Should I try to spend moremoney?
One of the biggest things thatyou guys have told me that I've
helped you with is I talk aboutRoth conversions a lot because a
lot of you have saved well to a401k.
(14:44):
You're not getting great taxstrategy from other aspects of
your life, from your currentadvisor, and you've learned
there's value to eating a littlecauliflower today to avoid
eating a lot in the future.
But you know what a big mistakea lot of you make is.
You create this beautiful Rothconversion strategy and you can
see if I convert to this bracketfor this amount of years and
pay taxes today.
It could yield hundreds ofthousands of tax savings in the
(15:06):
future, but you know what youshould do instead.
Yield hundreds of thousands oftax savings in the future, but
you know what you should doinstead.
You might actually enjoy yourlife more by retiring earlier,
by spending more money.
No one has ever come to me at 85going, ari, I'm just so glad I
had the best Roth conversionstrategy.
I have had people go.
I'm really glad I spent moremoney and helped my kid get that
down payment.
I'm really glad I retired fiveyears earlier because I got
(15:29):
trips that I could never getback because my health took a
big shift at 65.
Awesome, those are realpowerful stories.
So it's easy to get lost inthis.
It's easy to go.
Oh my gosh, ari, you have 300episodes on insurance and tax
and estate.
Oh my gosh, how am I going toever get through this?
Am I ever going to retire early?
No, the reason that I do thisis so people like yourselves who
(15:51):
save and invest well, reach outand find that when you find
it's time to have a partner, soyou don't have to have your
full-time job in retirementdoing this.
That's what we do here at Root.
Many of you, though, are in your30s or 40s and you want to
retire early, and I'm the weirdadvisor that says you shouldn't
pay us yet.
It doesn't make sense to, wecan't add value, it's not the
(16:12):
right time.
Keep saving and investing, butmaybe tweak some of these things
, giving you some insight, sowhen it does come time in the
future, you might find that thisis what you want to do.
I have people reach out who goAri, I love this.
When I retire, I'm going toread tax law.
This when I retire, I'm goingto read tax law.
I want to be the one runningthese projections.
And my spouse, I want them todo it too.
(16:34):
Okay, I don't hear that toooften, but there are people who
say that I say great, then don'tpay me, it would not make sense
.
Other people go no, I see thevalue because I want to spend my
time doing what I want, and Iwant to have a professional, a
third party.
I want to make sure, ifsomething happens, my spouse is
taken care of.
I want to delegate and have apartner, because I find value in
it, but it's not an all fitsone model.
(16:55):
One size fits all, should I saythe reason what makes Root Root
and me me is we're adding thistax strategy component that's so
often lost.
I cannot tell you how manytimes people have said I go ask
my advisor a tax question, theytell me to talk to my CPA.
My, you know.
I go ask my advisor a taxquestion, they tell me to talk
to my CPA.
My CPA says talk to my advisor.
My advisors has talked to myinsurance agent.
Here I am playing middleman or acoordinator role for retirement
(17:18):
.
That's not what this issupposed to look like.
You're supposed to have apartner, someone who is helping
with every step along the way soyou can enjoy what you've
worked so hard for.
Now there is an option that Italk about often in the episodes
that I record of this EarlyRetirement Academy.
That is really designed to giveyou a gut check.
There's not specificrecommendations.
(17:39):
That's a great option if youwant to go be your own advisor.
Build your own plan, run yourown scenario, see what am I on
track for.
How early could I actuallyretire?
What if it turns out?
My inflation assumption shouldbe lower.
What if it turns out?
You name it.
You can go play around.
It's a good gut check.
What it doesn't do is itdoesn't add in that layer of
(18:00):
peace of mind, of confidence, ofproactive planning.
It's not going to say, hey guys, while you're traveling, you
should have executed aconversion.
And here's the healthcaresubsidy that we're going to now
shift and, by the way, we'regoing to do a charitable
strategy because you didn't saveit, you didn't spend enough
money.
You told us you wanted to takesix trips.
You took four.
These are the real reasonspeople work with Root.
This podcast, though, isdesigned to educate you.
(18:22):
I hope it's entertaining alongthe way.
Just want to give you somebackstory on this podcast, why I
do what I do today, and I hopethat this was helpful.
I'll see you guys next week,back to our normal episodes.
Thank you all, as always, forlistening to the Early
Retirement Podcast.
I love getting to host theseshows and make different content
for you guys every single week.
(18:43):
I've not missed a single weekin years, and that is because I
love getting to do this.
Now, please be smart about this.
Before you actually execute anystrategy that you see me talk
about or hear me talk about,should I say Please talk to your
financial advisor, your taxpreparer, your estate attorney.
Please be smart about this.
None of this should beconstrued as financial advice.
(19:04):
This is for fun, educational,informational purposes only.
Once again, just quickdisclaimer here.
Guys, please be smart aboutthis.
Appreciate you listening, asalways, and you can, of course,
submit a question on my website,earlyretirementpodcastcom, if
you, of course, want me toaddress a specific case study or
topic.
I will not promise I can get toit, but I respond to every
(19:27):
single person and if I find itwill be helpful for a lot of
people, I will absolutely makean episode on it, at the very
least give you some insight.
That's it, thanks, guys.
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