Why someone worth $120m cut themselves off from making more money

Summary

In this episode of MoneyWise, host Sam delves into the complex relationship between wealth and happiness with guest Jeff, a retired founder who, despite amassing $120 million, realized that money wasn't the key to fulfillment. Jeff shares his journey of transitioning from relentless wealth accumulation to embracing a life of purpose without the pursuit of more money. He discusses the challenges of retiring, the importance of finding joy in spending and giving away wealth, and the shift in mindset required to truly enjoy life after achieving financial success. The episode explores themes of happiness, purpose, and the paradox of success, offering insights for those contemplating life after a big financial exit.

Takeaways

• 💰 The pursuit of money and the accumulation of wealth can sometimes overshadow the true purpose of enjoying life and can lead to a sense of isolation and frustration.
• 📈 Andrew Carnegie, once the richest person alive, had a moment of realization about the true value of wealth, similar to the guest Jeff, who also chose to stop pursuing more money.
• 🚀 Jeff, worth around $120 million, made a conscious decision to stop making money actively and focus on enjoying what he had built, reflecting on the idea that money should be used for enjoyment and philanthropy.
• 💡 Jeff's early relationship with money was influenced by his hardworking father, which instilled in him a strong drive to accumulate wealth.
• 💼 Jeff's first significant business exit was attributed to luck and timing, emphasizing the importance of being in the right place at the right time in business.
• 🚁 After his first major financial success, Jeff indulged in big purchases, including a jet, which brought mixed feelings of ecstasy and frustration.
• 🧘 Jeff experienced a shift in mindset from wealth accumulation to embracing life without the pursuit of more, influenced by a Yale paper and coaching.
• 🏆 Jeff's realization that happiness is not an endpoint, but a journey, led him to focus on enjoying his wealth and giving back, rather than chasing more money.
• 🤔 Jeff's experience highlights the importance of self-reflection and understanding one's relationship with money, and the need to find fulfillment beyond financial success.
• 🌐 Jeff's story serves as a reminder that the pursuit of money can be an addiction, and that finding contentment and purpose in life is more important than the constant chase for more wealth.

Q & A

Who is the main subject of the podcast episode in the script?

The main subject of the podcast episode is Jeff, a former entrepreneur who has chosen to stop pursuing more money despite his significant wealth.

What is the comparison made between Andrew Carnegie and Jeff in the script?

Andrew Carnegie is compared to Jeff in terms of wealth, with Carnegie being like the Jeff Bezos of the 1800s. However, unlike Carnegie, who continued to pursue wealth, Jeff has chosen to stop making more money by his own accord.

What is Jeff's estimated net worth as mentioned in the script?

Jeff's estimated net worth is around $120 million, which is completely liquid because he sold his company.

What significant purchase did Jeff make after receiving his first large check from the sale of his company?

Jeff bought a jet, which cost between three and four million dollars, as one of his significant purchases after receiving his first large check.

What is the main theme or lesson that Jeff learned from his wealth accumulation?

Jeff learned that the pursuit of more wealth was getting in the way of enjoying what he built, and he realized the importance of being content with what he has rather than constantly seeking more.

What is the name of the company that Sam, the host, co-founded?

Sam, the host, co-founded a company called Hampton, which is a community for business owners to discuss topics related to wealth and its impact on life.

What advice did Jeff receive after his first big payday?

Jeff received advice to not make any major purchases in the first year after his first big payday, but he admits to not following this advice and buying a jet instead.

What is Jeff's view on the accumulation of wealth as described in the script?

Jeff views the accumulation of wealth as an addiction and refers to himself as a 'recovering money addict.' He believes that having enough money should be the focus, not the constant pursuit of more.

What is the name of the Yale paper that influenced Jeff's mindset shift?

The Yale paper that influenced Jeff's mindset shift is called 'The Entrepreneur's Epilogue and the Paradox of Success.'

What is the '3 to 4% withdrawal' rule that Jeff mentions in the script?

The '3 to 4% withdrawal' rule that Jeff mentions is a financial guideline for spending from one's investments or savings, suggesting that withdrawing this percentage annually can help ensure the longevity of one's capital.

How does Jeff define 'enough' in terms of money?

Jeff defines 'enough' as the point where the pursuit of more money does not bring additional happiness or fulfillment. For him, this was around $20 million, where he felt he had enough to live comfortably without the need to accumulate more.

Outlines

00:00

💰 The Pursuit of Money and Its Limitations

The speaker introduces the paradox of wealth addiction, using Andrew Carnegie as an example of someone who had immense wealth but chose to limit his income for philanthropic purposes. The episode's guest, Jeff, chose to stop pursuing money beyond a certain point, despite the temptation. Jeff's story is about finding contentment in wealth and the challenges of enjoying it without the constant drive for more.

05:02

🚀 From Early Exit to Serial Entrepreneur

Jeff discusses his first company exit, attributing his success to luck and timing. After the dot-com bubble burst, he struggled to find his footing but eventually founded a B2B enterprise software business. This venture was slow to take off but grew steadily, reflecting Jeff's conservative approach to business and personal finance.

10:03

💼 The Turning Point of a Lucrative Exit

A competitor's unexpected interest in Jeff's company led to a significant exit, netting Jeff a life-changing sum of money. This event marked a turning point in his life, providing financial security but also challenging his preconceived notions about what happiness and fulfillment would look like with wealth.

15:03

🛫 The Highs and Lows of Lavish Spending

With newfound wealth, Jeff indulged in extravagant purchases, including a private jet, which brought mixed feelings of joy and frustration. He learned that material possessions do not guarantee happiness and that the pursuit of more money can overshadow the enjoyment of life's simple pleasures.

20:03

🏠 Finding Contentment Beyond the Dollar

Jeff's realization that money did not equate to happiness led him to a mindset shift. He began to focus on enjoying and giving away his wealth rather than amassing it. This change was inspired by a Yale paper and a coach who helped him understand the importance of living life fully, rather than being driven by the accumulation of wealth.

25:08

📊 Redirecting Wealth Toward Simplicity and Purpose

Jeff's wealth management strategy evolved toward simplicity, favoring Vanguard index ETFs over complex investments. He also unwound his real estate holdings and reduced his portfolio's complexity. His spending habits reflect a desire for experiences and items that bring him joy, rather than mere accumulation.

30:09

🤔 Reevaluating the Metrics of Success

Jeff's story concludes with a reflection on the true metrics of success. He suggests that energy and fulfillment should replace the pursuit of wealth as life's scoreboard. His advice for others is to define what they truly want, set a timeline, and pursue it with intention, whether that involves money or a different aspect of life.

Keywords

💡Money Addiction

The term 'Money Addiction' refers to an unhealthy obsession with acquiring wealth. In the video, it is presented as one of the two things people envy in addicts, suggesting a societal preoccupation with wealth. The speaker discusses how money was not the ultimate goal but a means to enjoy life and give away, contrasting the pursuit of money with the pursuit of happiness.

💡Andrew Carnegie

Andrew Carnegie, often compared to the Jeff Bezos of the 1800s, is mentioned as an example of someone who was extremely wealthy and had a significant impact on the speaker's perspective on wealth. Carnegie's diary entry about limiting his income for benevolent purposes is contrasted with his later actions, illustrating the complex relationship between wealth and personal values.

💡Jeff

Jeff is a central figure in the video who decided to stop pursuing wealth beyond a certain point. His story is used to explore the idea that having enough money can lead to a different way of living, focusing on enjoyment and philanthropy rather than endless accumulation. Jeff's narrative exemplifies the video's theme of finding contentment beyond material wealth.

💡Pursuit of Happiness

The 'Pursuit of Happiness' is a recurring theme in the video, emphasizing the idea that happiness is not derived from wealth alone. Jeff's realization that he was not as happy as he thought he would be after achieving financial success highlights the importance of this pursuit over the mere accumulation of money.

💡Liquid Assets

Liquid assets are financial assets that can be quickly converted into cash without affecting the asset's price. In the context of the video, Jeff's liquidation of his company and the subsequent discussion about his financial decisions illustrate the concept.

Highlights

Money and sex are considered the two addictions that people envy the most.

Andrew Carnegie, like Jeff Bezos in the 1800s, aimed to limit his income to $50,000 per year for benevolent purposes but later became one of the richest people ever.

Today's guest, Jeff, chose to stop making money by his own accord, realizing he had enough and removing the pursuit of more from his life.

Jeff is worth around $120 million, entirely liquid from selling his company, and believes life wouldn't be different even if he had stopped at $20 million.

Jeff's early relationship with money was influenced by his hardworking father, who instilled a sense of money's importance.

Jeff's first business exit was attributed to luck and timing, walking away with a million dollars.

After the first exit, Jeff experienced a failed software startup and struggled to find his next path for about three years.

Jeff's second business was a B2B enterprise software company, which grew steadily with a 20-25% annual growth rate.

Jeff's company was bootstrapped almost entirely, with a significant personal investment that represented 150% of his net worth at the time.

After 14 years of growth, Jeff received an acquisition offer from a competitor, leading to a life-changing payday.

Jeff's first check after the company's sale was $21 million, which brought certainty and financial security to his family.

Jeff's pursuit of more wealth after the first check led to additional payments totaling $88 million, but it didn't feel as fulfilling as expected.

Jeff's mindset shifted after realizing that accumulating wealth didn't necessarily equate to happiness, especially after crossing the $100 million mark.

Jeff hired a coach to help him shift his mindset from joyless accumulation to embracing life without the pursuit of more.

Jeff's new focus is on enjoying his wealth and giving it away, rather than fixating on accumulating more money.

Jeff's investments are moving towards Vanguard index ETFs, simplifying his portfolio and reducing the complexity of managing finances.

Jeff's annual spending includes a significant amount on netjets for flying, highlighting his desire for comfort and avoiding the stress of commercial flights.

Jeff's wealth allows him to spend $2 million to $3 million a year without concern, as his investments and net worth continue to grow.

Jeff's advice to his younger self would be to recognize the importance of structure and purpose in life, beyond just the pursuit of money.

Jeff's life scoreboard is now based on energy rather than money, emphasizing the importance of enjoying what you do over accumulating wealth.

Transcripts

money and sex are the only two

addictions where people really Envy the

addicts I'm here to tell you it's not

all that great I'm talking about money

of course all right so one of my

favorite people to read about is Andrew

Carnegie Andrew Carnegie was basically

like the Jeff Bezos of the 1800s in

America he was one of the richest people

to ever live and it's funny because he

said something when he was 33 he wrote

this in his diary he said I proposed to

take an income no greater than $50,000

per year Beyond this I am not going to

make a scent more and I'm going to spend

the rest of my time and money on

benevolent purposes let's cast aside

business forever and what's funny is two

years later he went on and started us

deal which is what made him the richest

person ever to live or one of and so he

didn't exactly stick to that however

today's guest is someone who actually

stopped making money by his own choice

he realized that he had enough money and

despite his overwhelming instincts he

committed to removing the pursuit of

more from his life life the whole point

of the money was to enjoy it to give it

away to live life the point of the money

was not the money that's Jeff and he's

worth around $120 million totally liquid

because he sold his company but he says

that if he stopped at $20 million his

life wouldn't be any different however

Jeff is quite the spender so I bought a

jet in this week's episode of MoneyWise

we're going to learn about how Jeff

realized that he's had enough how his

pursuit of more was getting in the way

of enjoying what he built and why he

thinks it's his duty to to spend his

money and by the way unlike Andrew

Carnegie so far Jeff has actually stuck

to his plan of not wanting to make any

more money for the rest of his life and

of course we're also going to get into

all the details about how much money he

has where all the money is and how he

invested and what his monthly expenses

are and all of that transparent stuff

that MoneyWise is famous

[Music]

for I'm Sam and this is MoneyWise

there's a ton of podcast and resources

out there that teach you how to become

wealthy but there's not a lot of stuff

out there that teaches you how to deal

with all of the life changes that wealth

brings the reason I know that is I'm

co-founder of a company called Hampton

you can see it at join hampton.com it's

a community where we focus on this

entire topic it's a community of

business owners we have thousands of

business owners people who are CEOs of

companies people who founded companies

people who own companies ranging from a

million in Revenue all the way up to

hundreds of millions of Revenue people

who have publicly traded companies and

that Community is what has inspired this

podcast I'm able to see all these

conversations that people are having

behind closed doors and I thought hey

let's make a podcast out of it because a

let's be honest it's good content

marketing for Hampton so if you are a

person who owns a company check it out

join hampton.com and B this stuff is so

fascinating you can't Google the stuff

you can't really find it anywhere I

thought it'd be awesome to bring it out

in the public with MoneyWise we provide

advice by talking to real people who

have achieved some amazing things and

they are radically transparent about

their life they're radically transparent

about the numbers meaning their

portfolio their income their monthly

expenses and more importantly they're

radically transparent about all the

personal issues and problems that come

with being successful things are rarely

ever discussed and how they're trying to

solve those problems you can also listen

to the show on Amazon music or just ask

Alexa by saying Alexa play MoneyWise on

Amazon

music this episode really is about when

the pursuit of money impedes on your

Pursuit of Happiness Jeff actually

refers to this urge to accumulate wealth

as an addiction I'm a recovering money

addict but I want to set something

straight before we really get into it

not making more doesn't mean not

spending Jeff is a huge spender and

we're going to talk about that more he

may be addicted to accumulating but that

definitely doesn't mean he's hoarding

his money Jeff feels quite comfortable

with the wealth that he's created and by

the way this is something that's really

unique to him he doesn't really feel

anxiety about his money running out or

going away and this journey he's on this

dedication to enjoying his life and

resisting the urge to make more money

isn't something that he's doing alone he

actually started a group of like-minded

Founders who are going through the same

thing we'll talk more about that soon

but enough about the rambling Preamble

let's get to the good stuff starting

with Jeff's early relationship to money

my mom was uh she was a teacher and a

nurse but stayed home to raise my sister

my dad was a he was an office worker

worked super hard I think I got my

thirst for money watching my dad leave

the house at before before anybody was

up and home at 6:15 for 6:30 dinner and

then disappear to do more work so I

think that was my initial view that

money must be pretty important how old

were you when you started your first

company if you exclude going door

to-door selling when I was eight

years old let's say uh the correct

answer is 28 I had a.com in the 97

through 99 range were you doing anything

interesting before that or just like a

normal Tech job it was a normal Tech job

my career was in sales out of school I

spent seven years two different tech

companies selling Hardware and then

software and just two years after

starting its first business Jeff gets

its first exit which he attributes a lot

to luck we got lucky actually I would

attribute it to maybe being a little bit

early in a wave but also like being at a

really hot blackjack table where a lot

of people were winning but managed to

walk away with some chips which was

great but most of the people stayed in

the casino too long and gave it all back

so I I was fortunate to have escaped

that era with a few chips in my pocket

the chips he's referencing is the

million he walked away with personally

after the deal fittingly he keeps using

the casino metaphor and he did lose some

of his money shortly after I was part of

a failed software startup that was part

of my giving some chips back to the

casino I dabbled in a couple of

different businesses and tried to figure

out what was next this is post.com bust

so Tech wasn't really a thing yet and I

was virtually unemployable at that point

so took about close to three years to

get started with something new I

eventually Jeff landed the big one and

that's his company that he started which

was a b2p enterprise software business

which he describes as nothing

interesting what was the idea or signal

that you had for number two I had a

technical co-founder that I had worked

with at two previous companies you know

if there's a way to pick a technical

co-founder it's work with that person in

a company where they're revered and you

understand this is the guy could be a

girl that in this case is a guy like

this is the guy I like to say you know

when you're starting a band if you have

a choice of having 20 really

accomplished guitar players or one Eddie

Van Halen go with Eddie so I got to

start with Eddie and Eddie had an idea

for a business we were a little early

took a while to get going $10,000 of

Revenue our first year 880,000 the

second year 300,000 third year Etc so we

didn't break even for five years so it

was it was it was tough sledding to get

going we bootstrapped it almost

completely so it was his idea what was

your startup Capital how much was it

less than a million dollars I had it

$50,000 raised from some local angels I

put about the same amount in myself and

then toward the end where we could see

profitability in sight we had a line of

credit that helped us get to a cash flow

Break Even those that was five years in

and then we never lost money again not

once of your 350 what percentage of your

net worth at the time was that at the

time that I put in the 350 yeah

150% oh really so you were you were

leveraged yeah no that's a my ego is

making Mak me seem more heroic than I

really am it was a lot it was it was

what we had what does that feel like did

have kids yeah yeah three kids it's

awful honestly it's awful it's tough to

get a business going I have a rule or I

have a a law maybe it's an axum and it

says if you're lucky it'll take you

twice as long and cost double what you

projected to get halfway to your worst

case

scenario and if that happens it's okay

you know you should do it anyway but

whatever that spreadsheet says where you

have your your worst case scenario just

plan on it taking twice as long and cos

him twice as much it was rough but you

know I had the support of a loving wife

and great kids and in-laws and parents

and friends and neighbors and great

employees so it was far from one

person's heroic

Journey Jeff continued to grind and grow

the company for 14 years we grew slow

and steady from the time we started

breaking even which was a million

dollars of recurring Revenue we grew

slow and steady we tended to be about 20

25% growth and about 20% profit in

hindsight I was running it way too

conservatively oh yeah it sounds like it

but who would have known right it wasn't

obvious back then it was not I I didn't

know I talk about the idea of this slot

machine there's reels that beenin and

you have your revenue of course and you

have your gross margin which ours were

great at 90% you have your uh your

retention rate our net retention was

117% so we took really good care of our

customers but our growth rate was only

about 20 25% % you know in that slot

machine it was like jackpot jackpot

potato and throughout all of this his

personal income also gradually increased

went from not getting paid to getting

paid kind of ramen wages to making a

decent salary to making I don't remember

at the end you know I was making

hundreds of thousands of dollars a year

it was all of my wealth essentially it

was realistically 95% of my my wealth

was in the business were you trying to

save as you went or you were like this

is a recurring business or at least

there's recurring cap cash flows I can

go ahead and spend a little and live out

of my means in terms of cash flow basis

or were you still living like a

relatively normal W2 earning lifestyle I

would say our lifestyle crept into a

more luxurious one over time but there

was never a moment where I thought this

is a stone cold lock we were one bad

line of code away from Extinction at any

point in time but then at the 14e Mark

things start to

change we got a call from a competitor

and they said I want to buy the company

we want to buy the company I said I

can't believe you'd call me you'd even

bother I'm a little bit offended but as

long as we're on the phone how much were

you thinking and they told me and that

was what why were you offended I was

joking I was I was bluffing I was like

tell me about the money how much am I

worth you know they gave me a number we

hired a banker and we ran a process and

it turned out we had built a sturdy

Little House on top of some pretty

valuable ground we ended up partnering

with the private Equity Firm that I I

wanted when that first check hit it was

magic man it was it was magic like many

other money degenerates I always had a

number in mind I thought if I had 10

million I'd be square 10 million of of

liquid assets I'd be square so of course

I secretly was wishing for 20 because

that's what we do the first check was 21

million that was my check personally wow

how old were you I would have been

47 yeah 47 48 that's a lot of money so

$21 million after taxes is what like 16

yeah there's some nice exemptions there

so it was it was probably like 18 after

taxes wow wow and that must have been

life-changing it was it was absolutely

life-changing it took it brought

certainty to my family and to myself for

the first time you know we were

fortunate to be able to roll some equity

which worked out great a $21 million

check is pretty insane that's absolutely

crazy but that was just the first of

three and the next two checks were even

bigger we're going to dive deep on that

in just a second after this short ad

break so here's the thing when I got my

first big payday after selling my

company when I got that first check I

got some amazing advice which is do not

make any major purchases in the first

year so I put a lot of money aside and I

just wanted to ease into my new reality

and I think that is a great bit of

advice however Jeff didn't do that I

bought everything the first thing that

he bought I bought a Jet a jet on on 18

million yeah that's a bubbly expense

that's a bubbly expense that was my one

big thing I always had a vision when I

was sitting in economy minus

traveling to see customers that one day

I was going to earn my way out of this

nonsense and I will never again sit next

to an overweight man in a hockey jersey

eating Panda Express taking a nap on my

shoulder it's not going to happen it's

not going to happen again how much was

that that jet was uh between three and

$4 million do you finance it no paid

cash we did what everybody does we put

it in a charter pool we thought it'd be

great we thought you know it's going to

make money for us when it's not flying

totally false what's false about that

everything

is it sort of like buying like where

you're like I'm just going to buy real

estate and you're like oh now I'm a

landlord and I got to like do stuff for

it and the returns aren't 10% cash on

cash it's more like 1% because I didn't

know what I was doing and you got to do

like eight of these deals in order to

find a winner it's a lot like that

except your real estate flies and breaks

down a lot and yeah so what was it like

let me answer correctly it was a

combination of ecstasy and rage when

things went

well and the plane was flying and the

pilots were okay and the trade table

wasn't broken the Wi-Fi was working and

people were charging it was great it was

ecstasy and then when things went wrong

it was a really quick way to get

frustrated and angry that you had worked

so hard for so long to get this prize

and it was grieving you somehow you

cannot calculate head trash in a spread

sheet Sam if you think about buying a

plane you I'm going to fly this many

hours we're going to Charter this many

hours it's this much operating cost this

much fix blah blah blah put a sell in

there that says head trash and try to

assign a value to it and then probably

multiply that number by 10 it doesn't

work what did you do with the rest of

the money a lot of it got invested I sat

in cash for a while I'm a pretty

conservative investor toward the end of

the first hold period we bought a house

in Big Sky Montana I think it was about

4 million so you're down to uh from your

18 or so you're down to what 10 or 12

liquid somewhere in there I don't know

that feels lean for some reason we did

sell the plane and actually made a small

profit in a fit of good luck that came

back maybe one way is looking at it as I

traded the plan for the ski house which

made me a lot happier and made my wife a

lot happier she's a mountain girl while

Jeff is making these big purchases and

accumulating head trash he's

simultaneously continuing to grow his

company before the next two parts of his

exit we had an additional exit in 2020

and then the Final Exit in 2022 and what

were each of those payments the second

was 40 and the third was 27 where did

you notice meaningful differences in how

you felt the big change was between our

the first check after the exit and the

second check so the first check

represented I'm set for life that was in

2017 it was a $21 million check but that

was the first big step change and then

the second one was the $40 million check

where it just more than I had planned

[Music]

on so 2140 and 27 that's a total of $88

million but after all of that after

achieving more than he ever expected Ed

from his business and just completely

walking away Jeff realized that it still

didn't feel right it didn't feel like he

thought it should the thing I tell

people was my my life in retirement is

easily a 10 out of 10 but I was sure it

would be at least a 12 I thought I'd be

flying around like doing cool with

fun people every day maybe somehow this

sounds so weird but maybe somehow the

universe would treat me a little

differently since I had somehow achieved

something that I set up to do

and it's isolating in a lot of ways and

it's frustrating in a lot of ways and

this is why I've been on this journey uh

hit the wall in in summer of 22 after I

bought everything that I could think to

buy and I'm one of these odd people that

has a hard time being happy I'm really

good at preparing to be happy just for

example the you know the checks have

come in and we've got money and I've got

four houses at this point but I'm not

quite ready to be happy because fill in

the blank the Theater seating in the

beach house isn't quite right and the

Sono system isn't sinking in this house

so like soon as I get this done then I'm

going to be happy and I got all the

things done in summer of 22 and I I

wasn't

[Music]

happy like Jeff said he got caught up in

seeing his money as a way to prepare to

be happy almost like building a company

with the expectation of an exit it was

always a work in progress until it was

finally ready for that next big payout

but that big payout was never coming

happiness isn't an exit life is

happening while you're doing that

building and if you can't figure out how

to be happy during the building part

during the journey I just think it's

rare that you're going to be happy

suddenly right after the exit and like a

lot of people in this position this all

became more clear to him after hitting a

major Milestone I'll make a confession

so I crossed 100 million last year and

when I crossed that threshold guess what

happened you wanted more almost I I got

protective of it I started thinking okay

if the Market's down a little bit gosh

am I only 97 now am I am I less than

that am I oh today's a good day I'm you

know2 like this is a good day and it's

so weird you can't lose a comma losing a

comma is a big deal it's another digit

yeah we're humans we happen to operate

on a base 10 numeral system so like

there's this thing it doesn't matter man

it doesn't matter and I'm reminding

myself by by explaining it to you I

think this concept of enough this is the

if you will the corner I'm standing on

in the world is helping people who have

enough who know they have enough not go

back and do it again for more money do

you know anybody that has just like gobs

of money doesn't spend barely spends a

fraction of it and they're still

slugging it out yeah a bunch that's the

majority of people I think run your own

race everyone right but for me the whole

point of the money was to enjoy it to

give it away to live life the point of

the money was not the money rather than

fixating on accumulating more money and

succumbing to the anxxiety of its

potential loss he instead started to

focus on letting go and living more

freely he decided to prioritize enjoying

his money because to be honest he

already has more than anyone could ever

really need he hit his Mark you touched

on the point of the money running away

from you maybe when you're not chasing

it not paying attention and I know this

sounds strange but it gives me angst

that that portfolio will run away from

us and again I look at it as my

obligation to put that money to work

you are a steward of that money and as

you know if you don't fly private your

kids will why not put it in play why not

put it in use you can either spend it or

give it away while you're alive and when

you're dead you can give it away or you

can give it to the government so there's

one that I definitely don't want to do

which is die and give it to the

government don't want to ruin my kids

what I want to do is spend it to the the

best of my ability and give it away to

the best causes that I can and keep it

flowing I'm trying to not be Scrooge

McDuck sitting on this big pile of coins

and bills and not letting it go I'm not

the richest duck in the world today

because I just saled my money away

Jeff's entire mind shift it's kind of

interesting it started because of a

paper that a lot of people have heard of

and maybe read listen to this the thing

that started me down this path is a

paper from Yale I believe it's called

the entrepreneurs epilogue and the

Paradox of success I found it four years

maybe into retirement where I thought I

had this rare weird disease that I was

the only human in the world that had it

and I read it and it's was like oh my

God this is it this is the thing what's

super interesting about the shift in

Jeff's mindset this commitment to

essentially cutting himself off from

making any more income is that as we

said it doesn't coincide with cutting

back on spending I promise we're going

to get to all the details about where

his money is and what he spends it on

his portfolio all of that good stuff but

before we get to that we've got to learn

a little bit about how we got mind to

ship that drastically because it really

isn't as easy as just saying hey I'm

going to change my mind this is a

project and this is a process we're

going to get to all that in a minute but

first a quick sponsor break we'll be

right

back so how did Jeff shift his mindset

from joyless accumulation to embracing

life without the pursuit of more

impeding on his happiness I hired a

coach his name is Rick enen bro he wrote

a book called what happens when you get

what you want which is really impactful

to me he was one of the co-authors of a

Yale paper that a lot of post exit

Founders have read and really resonated

with the thing that really unlocked for

me when going through therapy was I have

all of these processes that run in my

brain and one of those processes is

accumulating rather than

exle of one of the 12 I think my

favorite one is finding something wrong

and fixing it we were in the security

business when you run a security

software company it's important to find

something that's wrong and fix it right

away makes sense now go on vacation with

that guy right check into your suite at

the Four Seasons and I'm on my hands and

knees trying to fix a little Fray in the

carpet and my wife's like hey dummy did

you see the ocean yeah and it it it

doesn't matter so you have to like

basically deprogram yourself you have to

deprogram yourself

and accumulating wealth is one of those

things that's really hard and we talk

about this in this group I have it's

just starting I've got about 20 people

that are in it and the point of the

group is to assemble people who have

said they have

enough and I don't know the wealth range

is in it probably 25 million to a couple

hundred million there're people that

need the

accountability maybe from others or

appreciate the accountability from

others that look you've got enough and

let's not waste our brain Cycles talking

about how to get more I don't want to

sit in a room with people and talk about

how much money I have and then talk

about how to get more I'd rather talk

about how to make the most use of what

I've got how to enjoy it and how to give

it away how to have replac the purpose

that I had running a

company I don't really want to make this

episode about why you shouldn't go and

build more companies even if you made a

bunch of money because while I don't

think it's true for everyone there's a

lot of people of which I think I'm in

category who find genuine happiness from

entrepreneurship and creating stuff

what's important though is that you

think about why you're doing it do you

actually enjoy it or is it just because

you feel like you need to have more more

money more clout more success maybe you

don't know how to slow down and be still

and that's the whole point of this

conversation it's why I admire Jeff

Jeff's just one person so you can take

what you will from his personal

experience but for him work was

something that never truly brought him

Joy I think I like working like I like

high school when you think back you know

you think of the good things I play

basketball man those are my closest

buddies and I miss that but do I want to

sit through history class again or try

no I I think in aggregate no I didn't

like working I was in it for the

money now look neither Jeff nor I can

give you an answer about what makes

sense for you and this is something that

you'll need to do some soul searching on

I can tell you that removing work and

the pursuit of more from your life

doesn't mean removing projects that

bring purpose in life we talked about

that in our retirement episode which you

should go back and listen to it's

awesome but focusing on Jeff while he

stopped working he still has found

purpose in new projects I've I've

created two communities my retired

founder Community where I give advice

and never invest and never ask for

anything from anyone at any stage who's

starting a company I've got a I have a

huge love for Founders and I have a

connection to Founders we tend to just

communicate on the same frequency and it

brings me energy which is my scorecard

in life so that's a project and then my

beyond the Finish Line group that we're

talking about of people who have they've

had some success they know they have

enough they're trying to figure out what

to do with their next chapter my coach

says if you can't figure out what you

want you'll just want more and I've been

in that spot before so the challenges to

figure out what you want what's your

purpose what's going to replace the

Quest for money what's going to replace

the structure that you had running a

company in retirement so Jeff is now at

the point in his life where he's

intentionally not making more money and

as I mentioned his daily of massive

purchases are mostly over I feel like I

have optimal complexity and optimal

stuff right now it's more than I need I

only have cars that I love I only have

houses that I love I don't have a great

desire to accumulate

more stuff but the guy is worth $120

million so what is he doing with all of

his money how does he have it invested

this is a lot of people's favorite part

of money wives here it

is I'm glad you asked the headline I'd

like to lead with is all of the money is

moving in a direction of Vanguard index

ETFs and anyone listening who comes into

a windfall and thinks they're going to

enjoy Angel Investing and

Advising caution and I have

conversations like this all the time

I've had 50 of these I've yet to come

across someone who says investing in a

bunch of uh or a handful of Vanguard or

similar ETFs is is a bad idea everyone

goes through the same loop I did the

same thing I did a ton of Angel

Investments and they're going to make

money it's just boring it's just you

give someone money and you don't hear

from them for five or 10 years yeah and

then you're chasing k1s and I had a 240

page tax return and to your point yeah

some of them are going to make money and

that's fine but you know if you value

your your time and energy I wouldn't

recommend it what's like the portfolio

breakdown right now if I look at it at

Mac throw at last check just using 100

as a as an example I'm about 15% in cash

I own about $15 million worth of stuff

that's two houses a couple of plane

shares and just stuff and then about 70

million that's in the market and inside

the market again we're trending toward

the ETFs the index ETFs but I own a

decent chunk of uh real estate which I'm

in the process of unwinding own a decent

amount of not a lot but some private

Equity own some crypto handful of other

things but it's all running to the ETF

end of the

[Music]

table by the way what Jeff said here

about keeping it simple for your sanity

this is something that a lot of

successful people have talked about on

MoneyWise which is they just invest in

ETFs or mutual funds A lot of times

they're not buying individual stocks or

making a ton of different Investments

it's the simplest stuff that basically

everyone has access to now let's learn

about what he's spending on I try to

work from a 3 to four % withdrawal which

puts me in a spot to it's a great spot

to spend about $2 million a year what's

the breakdown you think of expenses I

don't look at it on a monthly basis I

can tell you on the on an annual basis

my number one expense isn't an

embarrassing one but I'll tell you that

it's netjets if you don't mind me

mentioning a brand name how much is that

per year that's about 700 750,000 a year

and how many flights a year does 700 get

you that is that that's 100 hours so

they'd be like going from Scottdale to

Austin Texas twice in a month is that

worth it it's worth it to me I have

friends that have way more money than I

have that fly economy or just can't get

themselves have a hard time stepping up

to a business class or a first class

ticket personally I have a problem with

uh emotionally with with flying and I'm

listening to myself talk it's the thing

that I really wanted Sam it's like the

reason I did what I did the reason I

took the risks in my mind a lot of it

was to be able to escape taking off my

shoes

and not having a 4 o bottle of shampoo

or something it just I I just wanted to

exit that so for me for me it's worth it

all right so then about 20 to 25% of

your annual spend is going to flights

what else uh it's probably higher than

that but number two thing is probably

just general expenses I I don't track

things you know in a Quicken spreadsheet

or or anything but the credit card bill

tends to run 30 grand a month something

like that that might be buying ski

passes for the kids or taking a nice

vacation or whatever it might be

we spend about $200,000 a year on our

homes between property tax and property

managers and utilities and insurance and

the things that go wrong we spend about

$250,000 a year on three really nice

club memberships that's a really good

spend of money and then we spend gosh I

don't know maybe 50,000 a year on I

don't have healthcare insurance conge

medicine and you know Healthcare

nutrition things like that also I just

want to call out something really quick

Jeff isn't actively pursuing more money

by working on or growing businesses but

the real estate that I own today has uh

is Cash flowing real estate that brings

it about 2 million a year two and a half

million a year with the three main

projects I have and on top of that even

though he's maybe spending $3 million a

year because of his Investments because

of his net worth which is around $120

million it's still going up

significantly each year compounding

growth once you already have a lot of

money it is insane which means two

things one no wonder why he's not

concerned about losing his money he's

got it set up so nicely he's made enough

he's totally spending even if it is $3

million 100% within his means and two

you could call him out and say hey look

dude technically you are making more

money but they are investments and it's

not exactly starting a new company so

I'll give him a pass there's one thing

though that I do want to challenge jef

[Music]

on remember early earlier when he said

this I always had a number in mind I

thought if I had 10 million I'd be

square although to be fair he did follow

up with this so of course I secretly was

wishing for 20 cuz that's what we do but

then after that first check of $21

million Jeff didn't stop he kept going

and he kept earning more I bring this up

because he said something else

interesting when I was asking him about

his monthly spend could I come up with

something that I wanted to buy would I

like to own a sports team in a private

island and whatever else I don't know

maybe I think I'd rather rent it effect

I can do anything I want to do and

frankly I could do anything I wanted to

do with that original goal of 10 million

and so I did some math and if he kept

the 3% rule which is spending 3% of your

total liquid net worth that's around

$300,000 a year however Jeff's spending

like3 million a year and $300,000 that's

only 10% but 3 million is what he said

he likes to spend now and that he's

really comfortable with that so I

pressed him on it and here's what he

said if you own your house and you know

you don't have any debt or or major

obligations that's a pretty good

lifestyle that may be a little on the

low side the stress and the friction in

life comes from the gap between what you

really want and need and who you are

which For Me Maybe it's 4 500,000 a year

and what you have so when you have

nothing and you want to spend 400,000

that's painful when you have a 100

million and you're really sort of

comfortable spending 400,000 a year it's

a weird spot and I can hear the eyes

rolling in your audience and I just want

to pause and say anyone listening that

says this guy is a total ass hat

hand me the 100 million get out of the

way and let me show you how it's done to

anyone thinking that I don't blame you

CU I would have thought the exact same

thing 10 years ago but I'm telling you

it's harder than you

[Music]

think even though you say that you have

enough do you still have you know a lot

of people I've got friends that are

worth hundreds of millions and they say

it's still not enough do you still ever

have those feelings of inadequacy

compared to other ear or to this is

nothing compared to what I could have or

things like that I do not have that I

don't suffer that one I have enough

which is the perfect amount of of money

to have is there a number that you think

you crossed where it was like that that

was it yeah I think it was 20 million

honestly I think it was 20 million and

and don't get me wrong I'm I'm a money

hound and if you said hey would you like

to have an extra 100 million I I

wouldn't I wouldn't shut the door but

I'm not going to spend the mental Cycles

to pursue that next comma or that next

digit 20 million that was enough yet

he's worth 120 million I asked him if he

could return to that initial point that

initial $21 million check and offer some

advice to his younger self what would he

say first I would tell myself you're

going to go through some stuff here and

you're going to miss the structure and

the purpose that you had in your life

that you were trying to get rid of to

get to the money and the spoils which is

actually the scaffolding that was

holding up my life that was one and then

the second thing would be I would ignore

what the world tells you which is go do

it again go be an angel investor go do

nonprofit work buy a bunch of stuff play

golf every day for me it's just not

fulfilling it didn't work now I know it

can be tough to let go of that Pursuit

for the next digit that desire for more

tends to get stronger I think as you

grow your wealth but while Jeff used to

get caught up in the numbers he shifted

to a new metric for life rather than

your scoreboard being money I think the

ultimate scoreboard is energy

if you can have energy for what you're

doing most of the time life is good and

it doesn't matter if you're flying

private or or reconomy if you've got

good energy when I go to bed at night I

run this routine says like is today a

rewind day would I want to relive this

day again some point in the future or is

it a skip day where I just like you know

it was okay but I I just I'd rather not

have this day again and if you get too

many in a row where it's a skip day

you'd rather not rewind that's where I

normally for me is energy based frankly

I think that's a much better metric than

adding commas to your net worth because

look no matter how much money you make

life is still life you have this Vision

right that you're going to be jetting

around doing cool in the you know

hanging out in the winter circle of life

but it's just it's not real most people

are back at work the vacation is is

great but I mean can you eat a hot fudge

Sunday every meal for just the meal you

know eventually it's like I got to have

something else it's a challenge to

replace the thing things that you think

you want to get away from are actually

holding you

[Music]

up I love talking to Jeff not because I

really see myself in his situation as in

I actually like working he didn't I do I

think maybe my taste may change but

right now I love doing stuff I love

building I love having teens I love all

of that stuff that comes with business

and just so happens that the output is

money but what I loved about Jeff is

that he was so purposeful and present he

acknowledged this is what I want and he

went and lived his life that way I think

the takeaway here for anyone listening

whether you have a lot of money or you

don't is to sit down in a quiet room and

write out what you think you want and

put numbers on it and put a timeline on

it and go after and get it and if you're

like Jeff and you don't have to work

then your goal should be look I'm not

going to commit to anything major right

now because that doesn't make me happy

if what you want is more money and you

think that will make you happy which who

am I to say maybe it will then you

should actually say how much money do

you want how much time you going to give

yourself and what are you going to do to

get after it and you go and you do that

thing I love people who say this is my

path and I'm going to get after it I

also love talking to Jeff because

there's so much more to life than

business I find myself getting sucked

into this trap all the time of thinking

about business constantly and Jeff's

story is a good reminder that after a

certain point it's just not that

important maybe it's the number three or

fourth most important thing in life

behind family your health and a few

other things but it's just awesome to

talk to someone who's actually more

well-rounded and so I was really

inspired by Jeff to just focus on not

getting more money but to figure out how

to live a better life and so I want to

know what do you think I'm on Twitter

atth Sam par let me know what you

thought about Jeff in this episode and

of course Jeff said something

interesting he said he has a group of

Founders who he meets with that's such

an easy plug for me here I got to plug

Hampton check it out join hampton.com

if you run a business if you are the CEO

of a business if you founded a business

you guys have to check this out it's a

company that I run it's a community and

here's how it works you go to the

website you apply my partner and I we

watch 100% of the interviews from the

people who have applied and we are the

ones who are in charge of letting people

in or not letting people in because we

want it to be a super high bar with high

quality people once in you're assigned

to a group of eight people who have

similar size and types of businesses

that you have and you meet monthly with

them to have all types of discussions on

these really really sensitive topics

that you can't Google you can't find

anywhere else we also have hundreds of

events throughout the year and we have a

digital Community where you can talk to

a thousand plus other members and you

could have these types of conversations

that I'm having with guests on money WS

so check it out join hampton.com of

course I also have to give a shout out

to lower Street lower street is the firm

who I hired to make this podcast I've

said many times this podcast is a

challenge to make but what I say is it's

not actually hard for for me because

lower Street has done all of the work

from helping me find guests to producing

the podcast which means editing it and

all these complicated things that I

don't understand these guys make it so

easy they made my life so easy so if

you're a company that wants to make a

podcast check them out lower street.com

MoneyWise all right we'll see you guys

next week

[Music]