Secrets of Post-Exit Happiness
Summary
TLDRIn this insightful interview, Shane Nean, the founder of Jun Bank and Easy Texting, shares his journey from being a nightlife entrepreneur to a successful investor and author. He discusses the challenges of transitioning from an operator to an investor, the importance of learning from mistakes, and the value of introspection and decision-making skills. Nean also reflects on his health journey, the impact of his mother's resilience, and his focus on being remembered as a good father and husband who contributed positively to society.
Takeaways
- 🎓 Shane Neuman's educational background includes studying computer science at NYU and initially pursuing a pre-med path, reflecting his early interest in medicine.
- 💡 His first entrepreneurial venture was a failed startup during the dot-com boom, which taught him valuable lessons about the tech industry and its volatility.
- 🌃 Shane's transition into the nightlife industry came from recognizing the inefficiencies in nightclub operations while picking up his girlfriend from work, leading to the creation of Junebug, a software platform for bars and nightclubs.
- 📈 Junebug's success was amplified by the addition of ticketing services, capitalizing on a market gap where smaller venues were not served by existing giants like Ticketmaster.
- 📲 The idea for EasyTexting emerged from Junebug's need to communicate with customers via text messages, which eventually became a separate, successful business due to high demand.
- 🔄 Shane's decision to sell Junebug and focus on EasyTexting was driven by the realization that EasyTexting had greater growth potential and was a 'shiny new object' compared to his long-standing commitment to Junebug.
- 💸 The sale of EasyTexting was prompted by burnout and a desire to spend more time with his new wife, reflecting a shift in life priorities after nearly two decades of non-stop work.
- 🏖 Post-exit, Shane experienced a period of adjustment, realizing the importance of not only preserving but also growing his wealth, which led him to learn investment strategies.
- 🧘 Shane's health journey included an intense focus on physical well-being, including cold plunging, weightlifting, and experimenting with various health supplements and practices.
- 🤔 The importance of introspection and learning from mistakes is highlighted by Shane's experience, emphasizing the value of personal growth and the adoption of new skills even after achieving success.
- 💡 Shane's humility and willingness to learn from experts in different fields, such as wealth management, demonstrate his adaptability and commitment to continuous improvement.
Q & A
What was the turning point for Shane Neuman that led him to become an investor?
-Shane Neuman realized he needed to learn how to become a good investor after not wanting to start another business, recognizing that being a good investor is very different from being a good operator.
What are the two businesses that Shane successfully built and exited?
-Shane successfully built and exited Junebug, a digital events powerhouse, and Easy Texting, the largest business SMS software platform in the US.
How did Shane's background in computer science influence his entrepreneurial journey?
-Shane's background in computer science provided him with the technical skills to build platforms and software solutions, which he leveraged to create Junebug and Easy Texting.
What was the initial business idea that led to the creation of Junebug?
-The initial business idea for Junebug came from Shane's observation of the inefficient pen-and-paper system used in nightclubs where his girlfriend worked, which led him to develop a platform to run nightclub and bar businesses.
What niche did Junebug fill in the market, and how did it grow the business?
-Junebug filled the niche of providing a software stack for nightclubs and bars, similar to what Toast does for restaurants, and it grew by adding ticketing services when there was no existing solution like Ticketmaster for smaller venues.
What was the inspiration behind starting Easy Texting, and how did it evolve?
-The inspiration behind Easy Texting was the realization that they had access to a lot of phone numbers and the emerging popularity of texting through devices like Blackberries. It started as an internal solution for Junebug and evolved into a standalone business due to its high demand and potential.
Why did Shane decide to sell Junebug, and what did he do with the capital from the sale?
-Shane decided to sell Junebug because he saw more potential in Easy Texting and wanted to focus on growing that business. He used the capital from the sale of Junebug to invest in Easy Texting.
What challenges did Shane face during his transition from an entrepreneur to an investor?
-Shane faced challenges such as learning to delegate, dealing with burnout, and shifting his mindset from a builder's mindset to an investor's mindset, which required a different approach and skillset.
How did Shane approach learning to become a good investor after his exit?
-Shane approached learning to become a good investor by surrounding himself with experts in various fields, learning from them, and taking small bets to learn before developing his own investment thesis.
What is the book that Shane authored, and what is its significance?
-Shane authored the book 'Nightlife: Lessons How I Conquered the Business of Partying with Tech', which shares his experiences and lessons learned from building businesses in the nightlife industry.
What advice does Shane give to new investors who have recently sold their companies?
-Shane advises new investors to find good mentors, learn from them, and not to avoid certain asset classes but rather understand them well. He also emphasizes the importance of learning from mistakes and not taking investment too seriously to the point of losing focus on other aspects of life.
Outlines
🚀 Entrepreneur to Investor: Shane's Journey
Shane reflects on his transition from operating two successful businesses to becoming a good investor, a skill he learned was very different from being a business operator. He discusses his ventures, including June bug, a digital events powerhouse, and Easy Texting, the largest business SMS software platform in the US. Shane also mentions his book 'Nightlife Lessons' and shares insights on his contentment and financial success after exiting his businesses.
🎓 From Premed to Party Tech Entrepreneur
Shane was initially on a pre-med track at NYU, but after a failed startup, he was persuaded by his roommate at Goldman Sachs to dive into the dot-com boom. He discusses the early days of his career, including a startup that was ahead of its time, which eventually failed due to the dot-com bubble burst. This experience, however, set the stage for his future entrepreneurial ventures in the nightlife industry.
💡 Identifying Opportunities in Nightlife
Shane's girlfriend worked at nightclubs, and he noticed the outdated systems used for payments. Seeing an opportunity, he developed a platform similar to Toast for nightclubs and bars, which eventually became the industry standard. The business grew significantly when they introduced ticketing, filling a gap in the market that larger companies like Ticketmaster didn't serve.
📈 Pivoting to a Tech Business and Scaling
Shane describes the growth of his nightclub software business and the strategic decision to pivot to Easy Texting when he realized the potential of text messaging as a marketing tool. He ran both businesses for a couple of years before deciding to focus on Easy Texting, which had higher growth potential. This decision was influenced by the unique challenges and experiences of operating in the nightlife industry.
🔄 The Transition from Business Operator to Investor
After selling his businesses, Shane faced the challenge of transitioning from a business operator to an investor. He discusses the importance of unlearning old habits and adopting an investor's mindset. Shane shares his initial struggles with this transition and the realization that being a good investor requires a different skill set from being a good operator.
🤔 Learning from Failures and False Starts
Shane talks about the process of learning to invest, which included making many mistakes and having false starts. He emphasizes the importance of learning from these experiences and adjusting his approach to investing. Shane also discusses the value of surrounding oneself with knowledgeable investors and learning from their expertise.
🧘♂️ Balancing Passion with Pragmatism in Investments
Shane shares his strategy for balancing his passion for venture investments with a pragmatic approach to preserving and growing his wealth. He discusses the importance of diversification and allocating time and resources to areas that are both necessary and enjoyable. Shane also talks about the role of venture investments in long-term wealth creation.
💼 The Emotional Side of Investing and Decision Making
Shane reflects on the emotional aspects of investing and the importance of making decisions without being swayed by emotions. He talks about the discipline required to avoid making impulsive decisions and the value of keeping a decision journal to review and learn from past choices.
🏠 Life After Selling a Business: Finding New Purpose
After selling his business, Shane discusses the emotional impact of no longer being part of a growing team and business. He talks about the importance of finding new purpose and meaning in life, such as focusing on family and personal growth, and how he managed the transition without succumbing to sadness or loss.
🏋️♂️ Health and Fitness as a Post-Exit Focus
Shane shares his journey into health and fitness after his business exit, including extreme measures he took to improve his health after being diagnosed with pre-diabetes. He talks about the importance of maintaining a balance and not overdoing it, as well as finding sustainable habits that contribute to long-term health.
🤝 The Importance of Reliance and Learning from Others
Shane discusses the challenges of relying on others, especially wealth managers, after being used to making decisions independently as a business owner. He talks about the humility in recognizing the expertise of others and the importance of learning from them to improve his own decision-making.
🏡 Legacy and Personal Values Post-Exit
In the final paragraph, Shane reflects on his personal values and what he hopes to be remembered for, emphasizing the importance of being a good father, husband, and contributing positively to society. He also discusses his views on legacy and the impermanence of fame and recognition.
Mindmap
Keywords
💡Investor
💡Operator
💡Nightlife Business
💡SaaS (Software as a Service)
💡Exit
💡Burnout
💡Delegation
💡Wealth Manager
💡Mindset Shift
💡Decision Making
💡Humility
Highlights
Shane Neuman's transition from business operator to investor after selling two successful businesses, Junebug and Easy Texting.
The importance of learning to become a good investor as opposed to being a good operator.
Shane's early life and education in New York, including his initial interest in medicine and computer science.
His first startup failure during the dot-com boom and the lessons learned from it.
Observing inefficiencies in nightclub operations and creating a software solution, leading to the establishment of Junebug.
The growth of Junebug through the addition of ticketing services for smaller venues.
Shane's experience dealing with the challenges and unscrupulous individuals in the nightlife industry.
The decision to sell Junebug and the opportunity to focus on Easy Texting, a business with more potential.
Easy Texting's rapid growth as a text messaging platform for businesses, filling a market gap similar to MailChimp for texting.
Shane's realization of the need to sell Easy Texting to focus on personal life and family.
His struggle with burnout and the desire to have more control over his time after selling his businesses.
The process of becoming a successful investor, including learning from mistakes and surrounding oneself with experts.
Shane's approach to balancing investments across different asset classes and focusing on venture capital.
The importance of having a financial advisor to maintain emotional stability during investment fluctuations.
His experience with health and fitness, including battling pre-diabetes and adopting a strict health regimen.
Shane's reflections on his legacy and the desire to be remembered as a good person and family man.
The value of introspection and continuous learning as part of the post-exit journey for entrepreneurs.
Transcripts
if I didn't want to start another
business I had to learn how to become a
good investor um which is diametrically
different than um being a good operator
because you tend to do a lot and the
more you do as an investor sometimes
really is SM for Shane nean he
successfully built and exited two iconic
businesses Jun bank at digital events
Powerhouse and easy texting the largest
business SMS software platform in the US
you know I had an opportunity and I kind
of said to myself like what's the magic
number that would make me happy today he
manages a substantial real estate
portfolio invested in over 50 startups
and authored the book called nightlife
lessons how I conquered the business of
partying with tech in this episode Shane
reveals the secret behind his transition
from the daily stress of running two
businesses to achieving contentment and
impress financial
[Music]
success Shane
hi Hi how are you very well and very
excited about this interview likewise
likewise so Shane when I first met you
at that boat event in Miami you came
across as a very you know solid stable
family man so I was quite uh surprised
when I later found out that you spent
most of your uh life with a strong reput
ation of a party animal and even wrote a
book called nightlife lessons about
partying in New York I spent my 20s in
New York too so I was very very curious
to to compare notes and and and read it
um but I would love you to share a
little bit with my audience um that part
of your life I'm actually a native New
Yorker I was born in New York um I was
born in Brooklyn so um uh I grew up my
entire life in New York initially queens
and then Long Island and um I went to
NYU for undergrad um and I studied I
studied computer science and I actually
went to NYU Med I was Premed right after
um so I had a you know the thought of
like going into the nightlife business
was never my aspiration I was kind of
like a nerd let's just put it that way a
little bit um a computer nerd and um and
I really just did computer science
actually as a fall back if I didn't get
into med school cuz at that time U you
know in the in the early '90s
um you know it was still like really I I
don't know how it is now but it was like
really really hard and being a doctor
was like the ultimate goal uh I'm not
sure sure if that's uh the case now but
um anyway uh I actually did a startup
before June bug um for about a year year
and a half uh that was a failed startup
my roommate was at Goldman Sachs at the
time and um he convinced me to drop out
of med school and join the do com boom
yeah uh he's like he said he said well
look I can raise all this money you know
how to program um we can make a great
team let's try and do this and um I
don't know I couldn't argue with that so
I could always go back to med school
right so anyway got my taste of
Entrepreneurship through that roller
coaster ride uh some some some people
thought some investors thought it was a
good idea to give a bunch of 22 year-
olds millions of dollars um and uh we
built basically what what you would call
Microsoft 365 now but through Citrix um
so a lot of those words that are used
now like cloud and App Store and SAS you
know just really didn't exist and like
there wasn't even really Broadband
penetration that much in the early in
the late 90s
um and
so uh you know we built a great product
that was really too early for his time
and then the do bus
happened um and we went down with the
ship uh just like many others um and I
actually had lost all my savings things
too because I had been programming on
the side and you know making money
during college and um I put my money
where my mouth was investing in the
company as well uh and then um I don't
know through a bunch of really weird
twists and turns
um uh what happened was that my girl I
moved into my my girlfriend's dorm she
was going to fit at the time to save
money um
and she was working at some nightclubs
on the side to make money and I would go
and pick her up or go with her sometimes
uh and like you know she was getting
paid at 3:00 in the morning and it was
really kind of backwards the whole there
was no there was no systems in place uh
it was all pen and
paper uh it didn't really make a lot of
sense um and I actually saw an
opportunity there so um June buug
basically built we I I I went back to
not my dorm room but her dorm room and I
was coding uh so it was like kind of uh
cliche in that in that respect and um we
built a platform for basically
nightclubs and bars like the same as
like toast does for night you know
restaurants um to run their business on
um and then that grew really we became
the defao of software stack
um That Grew into a really large
business and then it really took off
when we added ticketing um and there
were really
no sorry there were really no um like
Ticket Master was not serving smaller
venues and there was there was no event
bright you have to understand this is
like a pre- MySpace pre Facebook pre
camera phone time right um people can't
remember that time right uh but like 19
you know 2001 those things were not
really happening um
and nothing you know uh we we hit a
niche um there was a need for it it was
easy to scale because there wasn't very
many there no one was really thinking in
that in that vertical about tech and
night life and that kind of thing uh was
able to grow a really big business out
of it um and really learn
um how to get screwed in every possible
way you can never get screwed in
business because uh that's I mean you're
dealing with nightclub owners and
unscrupulous people um I can imagine a
very special kind of crowd yeah yeah uh
you know really shortsighted people hard
to convince hard to um monetize on so if
you can really crack that market um you
know they say like you know if you in
New York if you can make it there you
can make it anywhere they should change
that for like if you can make it in NTI
in New York you can make it anywhere cuz
the hustle is real um yeah and it's a
doggy dog kind of um industry for sure
um very very very
fickle so why did you decide to sell how
did that happen I was getting a little
bit older uh so I started junbug when I
was like let's say like 24 I remember
something like 23 or 24 was a few years
after med school and and the failure of
that um company I had been doing it for
about eight or nine years at that point
um and what happened was is that
actually during in
20056 uh what happened was is that we
realized that we had phone numbers for a
lot of people and we also built like a
marketing U stack where people could
send emails out and sell their tickets
and market and we realized had
everyone's phone number and there was no
way to text them uh and texting was just
really starting to kind of take off in
the United States with blackberries and
that kind of stuff and and so you know
if you can't find it you build it uh I
built it initially internally for our
company um used it it was like it was
like a silver bullet magic um cut
through all theut clutter of the Inbox
and spam and and no one was really doing
it and had crazy open rates and response
rates and um people were asking me how
did you do that how did you do that and
then I realized that that could become a
business in itself um if you can imagine
like a MailChimp or a constant contact
for texting you know just didn't didn't
exist and so we spun that out it was
called easy texting yeah and so I ran
those two for like a year or two
together um and then I realized that
easy texting had much more potential it
was a really it could become a really
really big business and and not that not
that nightlife you know not like not not
like Junebug wasn't a big business but
it was also the shiny new object I had
been doing that one for the other you
know the other one for eight years and
so we just called up our competitor and
that was always kind of nipping at our
heels and said said Hey look it's either
now or never if you've always wanted
this opportunity we're willing to sell
and then I took a lot of the the the
capital from the sale of that of Junebug
and kind of Pumped it into easy texing
and then did that for another like eight
or nine years so so you didn't take any
break in between them because you
already had the second company to run
yeah I had a successful company that was
actually making money um and so I I had
a lot of um
drive to to to build that business as
well so by the time you sold uh easy
texting it had been like 20 years of
non-stop building wasn't it almost yeah
yeah it was almost yeah yeah it was it
was like uh 19 years or something and
that's when was the first time when you
had a chance to stop and actually think
about your life wasn't it I don't think
I really thought about much else than
work to be honest uh work and then you
know I had time to kind of go out and
you know be young and party a little bit
and you know that kind of stuff but I
mean as a practical matter even though I
was in The Nightlife business I really
wasn't like going and drinking and doing
crazy stuff I mean I would go out but
like any normal person would but um I
went to the office at like 9:00 in the
morning like everyone else and I had
employees and
I might have had access to certain
things that people didn't have which was
cool from the outside for most people it
looked like you were you were partying
all day
long no because because of the industry
you were in no it's very hard to do that
and you know have a have a multi-million
dollar company with you know a lot of
employees and that kind of stuff and
well I mean I guess you can build it
like that but to maintain it you know
it'll fall apart if you don't um so
Shane um fast forward to your exit from
Easy texting why did that happen so I
think um like a lot of people uh who get
to a certain level um I was you know
always constantly under the stress of my
business um I um lived and breathed my
business um
and I had just met my current wife um I
had you know and I wanted to have a
family um I wanted to see her more uh
obviously um because it was it was
craziness like you know I'm sure just
like a lot of startup Founders you know
experience you know you're working all
hours um you know I had a team in in
Ukraine we had a whole office in Ukraine
so that time zone was different um there
are emergencies that you have to put out
um you know that that that constantly
come come up and um you know so it was
the your burnout essentially you got
tired and it was my burnout I tried to
replace myself you know and you know
take that classic
um advice and delegate and and and I
guess I just wasn't too good at it just
to be honest uh in retrospect um I tried
you know hiring people that I thought
could replace me
um it was easier said than done nobody
kind of really fit the bill and then um
I you know I I tried to delegate and you
know that that didn't work too well for
me either uh and and I had an
opportunity to sell because someone you
know I was getting approached because I
had a company that was a SAS company
that was growing you know at least 40
50% a year it had like 60 70% margins we
were profitable like no one had seen
something that yeah so um you know we
had we you know I had an opportunity and
I kind of said to myself at what
point like what's the magic number that
would make me happy essentially and I'd
be willing to kind of give this up and
like you know figure something else out
you know that that kind of thing
um and you know it happened someone was
willing to give me you know my number um
and I was going to be happy with that
and and with my decision and uh in
retrospect now um easy taxing is much
bigger than when I 10 years ago and I
would have had a much bigger company
arguably and and and many other things
but I would have never given it up
because I was able to experience so many
other things um so no
regrets no regrets no I mean like it if
you looked at it only financially it
would be regrettable um possibly um but
I got to you know move to Miami first of
all I would have never been able to do
that uh from New York uh I you know I I
had my first daughter my first child 10
years ago and I was really truly present
for her and I got to experience that um
and then you know I I really pivoted at
that point because I realized that if I
didn't want to start another business I
had to learn how to become a good
investor um which is
diametrically different yeah than um
being a good um operator right sometimes
um because you tend to do a lot and the
more you do as an investor sometimes
really is harmful um and also just kind
of learning how to shift your mindset
into an Investor's mindset versus a
builder's mindset is very different
um trying to do that yeah what helped
you in your transition because at least
to me you look like an exceptionally
successful investor and it seems you
seem to be very happy being one and
that's not necessarily very common in in
our post exit founder Community as you
know lots of people feel very miserable
yeah investing instead of building
yeah so I think there's a couple of
things first of all I think a lot of
people fall into the Trap of identifying
themselves with what they do um or their
company
um I thankfully really never had that
thing like I never like saw myself as
easy texting or I never saw myself as
June buug I saw it more of like an ends
ends to a means like it's what I did it
wasn't who I was yeah um not that I
didn't I I I liked what I did I did I
mean I liked I I loved aspects of what I
did but like as a Founder you do a lot
of [ __ ] that you really don't want to do
just to be honest and that what makes
you a good founder is like your
willingness to do things that other
people won't do right um
so uh I think you know you're looking at
something that's 10 years in the making
right so uh Poss Poss in the beginning I
I don't think you would have said the
same thing like looking at me um it was
a process for me um yeah I had to learn
I made a lot of mistakes um there were a
lot of times where I kind of had these
false starts where I thought that I
would start a new business and then I
had to kind of hold myself back and be
like wait did I re this is am I sure I
want this you know is this extra x
amount that I possibly could make going
to make me happy or you know do I value
my time um and and being able to control
my own time which I can now right for
the most part I mean you know there's
always exceptions to the rule but
um I think that uh you know it it's just
as hard as you know initially of you
know doing a startup um in terms of you
know Finding Your footing um uh and it's
it's it's a lot of a lot of
mistakes and learning from your mistakes
uh so what were what were the biggest
mistakes in terms of types of
Investments not necessarily you
know we we don't necessarily need all
the details but what for
example if I if if I just sold my
company and I would be asking you can
you please tell me what to avoid
investment wise What would you tell
me I think um what I would say is there
isn't like a particular type of
investment that I think you should avoid
I think all Investments can be all
different asset classes can be good
Investments if you know what you're
doing um I think what you really need to
do is um truly figure out figure out I
think the key is figure out who really
are who who's really good investor and
who really knows what they're talking
about who's an expert in that field and
you know learning from them um and I
think that you know if you really like
to learn um bless
you yeah yeah if you really like to
learn and you bring yourself to a place
where you know you're you're curious
about everything um and you know you can
you can become interested and I think
listen people like what they're good at
right and so once you kind of get some
small successes right under your belt
you start to like it better obviously
you don't like it when you you lose and
you know it doesn't feel good right um
but when you're winning it it feels good
and um you know some people you know all
of a sudden win and then think they're
like a genius right and they don't
realize that you know a lot of luck goes
into it too of course uh but I think
I I think instead of trying to avoid uh
certain asset classes and saying this
asset class is bad or whatever I think
the better ideas trying to surround and
by the way you know if you're in YPO or
tiger 21 or any of these other kind of
organizations um there's so many people
who've made it in all these different
industries that you can leverage um and
speak to and you know like I for me I'm
in Tiger right I'm in I'm in a few other
things as well and you know there's
there's a couple there's there's a few
guys that I met that like you know are
really crypto guys right and you know if
you ask people at different
times you know crypto could have been
the worst asset class or the best asset
class you could have been in right uh so
it all really depends on anything but
like I really you know pick their brain
I talk to them interested I learn I
maybe take small bets so I can learn um
and and that kind of thing before I kind
of come up with my own um thesis thesis
or I also think that one of the things
that I did that was um very important
that I think was a building block in My
Success was that I found initially a
wealth
manager that was willing to teach me not
just kind of like
just do it and then like I had to listen
to them they they were willing to sit
down and tell me why they were doing
certain things or why they thought
something was a good investment and
really take me through it um and you
know I did that for a few years
initially until I could feel confident
about myself being able to do that later
on and it was a it was like you know it
was a process it was a few years um but
now I do that myself and I feel
confident enough um that I can kind of
to take bats in a way that uh you know
but it sounds like it took it sounds
like it took you years to identify those
people and then learn what you needed to
learn right so oh yeah and I made a lot
of
mistakes there were a lot of of a lot of
people who I thought were
um were experts um yeah and and you know
like you know people tell you real
estate safe well I made like three or
four real estate Investments that went
to zero if you can believe that right
wow yeah because you know I was LP I got
you know I got wiped out as pref Equity
because the the and or I bought office
you know we bought office like six seven
years ago right and yeah and and um you
know it's it's going to go to zero right
um and so and then there were really
there were the real estate guys that I
did business with that like you know I
made tons of money with and they were
right right um so you you know I I think
it's
unavoidable um I think you have to kind
of uh also think of it as a
game um and and and and you know not
take it too seriously some people are
really kind of um too too focused on not
not losing and and instead of learning
um uh so that that's not to say to take
these crazy bets where you know if you
lose you know you lose everything the
idea is to you know take as many good
bets as you possibly can and you can
play a perfect poker hand and still lose
right um but you have to kind of come to
terms come to terms with that right um
so so Shane in my own experience and my
observation so far is that for most
people they first
lose quite a lot not necessarily quite
but some of their exit wealth before it
starts growing so most people expect
when they sell the company and then they
calculate what kind of rate of return
they want they expect uh that curve to
go straight up but it almost never
happens because that learning is always
costly did you find that true for
yourself as well yeah of course I went
down before I went up um and and and um
I was freaking out by the way when we
just like you know happen to me I
totally understand yeah you know and and
I think that's actually where a good
financial advisor is a big asset is more
so not telling you what to buy uh or
that or explaining it to you but kind of
keeping you emotionally in check yeah um
and not doing things that you're not
supposed to do um you know I think being
an
investor you know I mean if you look at
the best investors like a Buffett or
some of these other guys mean they're on
the Spectrum right so they don't they
don't like experience emotion like like
most people do and so they're able to
make judgment calls emotional without
emotion um and it serves them very well
in in investing um it's very hard to be
like that yeah also also you can't be a
successful entrepreneur like that
because you actually have to have lots
of P passion so other people catch that
passion from you and get energized by
you um I I totally agree with you you
most entrepreneurs if anything are very
emotional even though they learn not to
show it over time here whether it's
greed whether it's whatever it is
whether it's like just altruism or
whatever it is that they that's driving
them it's the extreme of that that makes
them successful and it's it's actually
the downfall of the investor right
so so from the Practical standpoint how
did you turn yourself into uh a Warren
Buffett type and sto being emotional I
by the way I am not nearly
not that is like really not what I am um
I I I've I I think I've done pretty well
um but I am not um listen I think like
every other entrepreneur right I'm
always hardest on myself um but I'm by
far not the best investor
um I think you know I'm constantly
learning and I still make a lot of
mistakes um but now I think I make fewer
mistakes than I did 10 years ago let's
just put it that way which I think is
just the key um uh to to being you know
a pretty decent investor
um
but look I
think I think I do a lot of things that
a lot of people don't want to do because
it it's not fun to do right uh it just
you know it's the same thing as being an
entrepreneur right like you do a lot of
things that you know like I would sweep
the floors if I had to in you know in my
in my startup there was nothing beneath
me to do um you know I I keep a decision
Journal when I make major decisions and
so and then every three months every
quarter I review the decisions and I and
it's like a giant pain in the ass to do
it takes like a long time and it's like
you know tedious and I have my own
methodology of how to do it but I use
like my note app and I go back and I and
I Rego back to even decisions that I
made years ago and I try and learn from
them so that I
can make better things or actually it
shifts my perspective sometimes because
sometimes a decision that I made may
have made a few years ago in the short
term might have the outcome of it might
have been perceived it was bad let's
just
say but it actually turned out to be
really good uh you know if if you waited
long enough right or or or vice versa it
was great in the short term but turned
out to be bad in the long term um and
that might still change too by the way
in like 5 years from now um so I think
you know doing those types of things um
it's hard to do it's a giant pain in the
ass and a lot of people will think of it
as pointless how did you get yourself
excited about about it I'm not like
excited about real estate let's just put
it that way right like I do real estate
and like I'm pretty good at it let's say
because I have a lot of experience with
it and it makes money and but I don't
like love real estate like some people
might love real estate and I don't love
stocks and bonds and I don't love you
know certain things but I really do love
Venture right and and so what I do is
you know I allocate correctly um for me
and my an uh and where I am um and I
spend like 40% of my time on stuff that
I don't love right and then I spend 60%
of my time on Venture which I love and
that that gives me the time with let's
say um really uh really smart um other
Founders startup Founders early stage
late stage Founders and I look at a lot
of different companies I read their
decks I spend time with them I call them
I invest and then I also you know helped
them along actually the book that I
wrote was a result of the so much of the
time that I spent saying the same
stories over and over to them and I the
way I structured it was you know each
chapter was a lesson that I learned
that's why it's called NTI lessons yeah
and then I kind of circled it back to
like how I use that lesson in another
company that I either did or or I
invested in or how how how I how I use
it in my um everyday investing you know
which I thought which I thought would be
helpful it's not just like kind of like
[ __ ] advice that you hear that's
like esoteric and like no one really um
things so um I I think the key is is
that you know spending doing what you
have to do right like I have to do the
other 40% because it's still very
important um I don't love it I don't
hate it but I don't love it um and and
it's a necessary thing for me to do to
be able to spend the other 60 50% of my
time doing stuff that I really love um
and I'd like to do so you basically have
the sense you you basically have the
sense of responsibility for for your
wealth and that's what drives that 40%
and then 60% of your time is no one's
gonna give a damn about your
wealth except for you trust me no wealth
advisor no one is going to really give a
damn cuz you know like you're really you
and your family or you know your whoever
else you know your your significant
other are the ones that are going to
Care the most right because it directly
affects you so um how could you not you
know you it's you have a you have a real
responsibility to make you know to
yourself to to to make that happen and
Venture Investments mostly Come From
Love or you also feel that it's a good
uh investment decision if you're in a
position where you want to grow have
long-term wealth right um You really you
really have to have a pretty good
exposure to things like venture or
Venture like asset classes um in order
to defy wealth destruction um just even
if you were able to let's say maintain
right
um I think you know a lot it's very hard
to live you know for for people to think
in Long scale time frames um but it was
it was it was funny um I actually went
you know I listened to I went to a
dinner and Michael sailor
um uh was was you know he's he's he's
like a Bitcoin maximalist um micro
strategies I don't know if you know just
a public company they own most and he he
spoke at the dinner it was actually at
his house and so he he lives here in
Miami and you know he got up in the
middle it was like 40 50 people in his
house it was a big ballroom and he's
he's like yeah um I just got my house
appraise for like $48 million and you're
like thinking to yourself why is this
guy telling me this but you know he's
like I bought it for I don't know 30
million like five years ago or six years
ago and then this house was built by a
family who came here in the 1920s and
they built this house in the house next
door for
$120,000 now the reason why I'm telling
you this is is that if they took that
$120,000 and buried it in the ground and
gave it to their
grandchildren their grandchildren right
now wouldn't even be able to buy a
square foot of my driveway with that
$120,000 and so if you think about it
that's like just two generations right
um and so you know that's not going to
happen with bonds right it's not going
to happen with treasuries it's not going
to happen with and I'm not saying you
shouldn't have some you know in my in my
opinion and by the way again I'm not
like the best investor at all but I try
and kind of emulate who I think are the
better investors which if you look at
like endowments or those types of um
people they have a really
healthy um allocation to venture right
or or or much larger uh let's just say
to venture because they're really
thinking you know 50 years out 60 years
out maybe 100 years out sometimes um and
so you know you have to get Alpha in
order to maintain wealth over time
because the the you know the value of
your money is being destroyed
up unless like Michael sailor gets his
way and like Bitcoin becomes you know
the the the the the you know the the
universal um currency and then you know
then you you can't you know inflation
would stop but um I don't know that's
that's like that's a totally different
bet Shane switching away from investing
to your personal life so sure can we go
back again to that moment when you sold
easy texting you are free from your
businesses you have a chance to stop and
think and and heal from whatever it is
you you may have hurt uh during 20 years
of
grinding how did you feel in on that day
when you sold it I felt really happy I'm
not going to lie it was amazing um I saw
a lot of money in my bank account
um I was newly married and um you know I
I um I just saw a lot of potential I saw
a lot of potential ahead ahead of me um
you know and then I would maybe say a
month later you know reality kicks in
again nothing really changed nothing's
really changed yeah um I don't know for
me I was never like um a person that
like said oh if I get this I'm going to
buy a Ferrari or I'm going to buy you
know like I was just never that person I
never really cared I mean I like nice
things don't get me wrong like yeah you
know but I'm not like doing it for that
um I think everyone likes nice things
right like you know like nice vacation
or whatever you know that that kind of
thing but like I wasn't like ever
thinking to myself I you know like I
want to buy a boat or I want to buy like
a plane or like those things would just
never were were like things of that that
were goals of mine let's just put it
that way um
but then the reality kind of really set
into me being like wait how do I not
only not lose this now right but how do
I make this last forever right um I had
a really keen understanding of that that
that would need to happen pretty quickly
because um you know all of a sudden you
know I was on payroll I stayed for like
another year let's just say but like I
wasn't getting paid anything close to
like what I was getting paid before um
and I was like oh well my income's gone
right
um so you know I'm going to either have
to work again or try and figure out a
way to make this last a really long time
and grow it um and I didn't know how I
was going to do that so that that became
another source of stress let's just say
a different s source of of course
stress the only
difference what was that it wasn't like
at all hours of the day and putting out
fires and it was a different kind of
stress that was I think for me at least
more
manageable um and didn't like you know
all consume me let's just
say um
so uh listen there's there's problems on
each side right it's just you have to
choose choose which problems you want
basically
did you feel sad that you no longer had
the team and the structure and the
famili environment and the business that
was growing was sadness part of your um
how you felt at the moment I had a uh I
had a hard like a pretty hard childhood
it wasn't not I didn't have like a bad
childhood but I had a pretty hard
childhood you know I lost my father when
I was 13 uh my mother was like
perpetually ill her entire life I we
lived a pretty comfortable life a good
life life you know like um a middle
class life kind of thing um and you know
my mom worked and I saw her kind of work
despite her illness and like if she
could make it like I could you know I
could make it kind of thing like so a
lot of people ask like who your Mentor
is or whatever uh you know was obvious
for me it was my mom because like she
was able to accomplish all a lot being
really ill her entire life
um and you know I kind of really
understood the concept of
um you know non-permanence of things
let's just let's just say yeah and and
and and and being being able to accept
change at a rapid
Pace um you know my mom was you know was
ill and in in and out of you know the
hospitals all the time and stuff like
that so things would change for me a lot
uh you know all the time and I would
make plans and like go to go away and
then I I I stop making plans because
like you know a lot of times it would
get canceled cuz I was you know in the
unknown a lot of times so the
impermanence of things kind of you know
was uh staple in my life maybe i'
learned that earlier in in life um so I
I don't know I I think you
know be for me it was it wasn't that
difficult to deal with change because I
had that a lot happen to me earlier
makes sense um yeah but like yeah listen
did I did I kind of miss it a little bit
yes I did but thankfully I had other
things that I had was like really
grateful for like I had a child and I
was having that experience and we moved
to Miami and I had that experience and
so
um you know I kind of replaced it with
things that you know occupied me
essentially yeah yeah it sounds like you
had a lot on on your hands didn't have
the luxury to feel sad right yes I think
that's actually something that I that I
got from my mom you know she never like
didn't she never was like felt sorry for
herself cuz she never had the time she
just you know pushed through right like
I think that's maybe a coping mechanism
that that a lot of people use basically
did you do anything for your health
specifically because we get quite burnt
out uh after entrepreneurial experience
and uh as you know we have lots of
common friends who go really really
extreme into biohacking or extreme
sports like really focus on on on their
health um and physical development did
that happen to you it did it did um and
I still to a degree do it um so like I
still do cold plunging I have a cold
plunge I do sauna um but then I kind of
like took it to a pretty extreme for a
few years uh when I turned 40 like seven
years ago six seven years ago um I got
diagnosed with pre-diabetes and I wasn't
even really that I wasn't obese or
anything like that it was really
shocking to be honest yeah um and going
to med school like I understood how bad
that really is um for your prognosis
let's just say of like all the bad
things that can happen to you afterwards
especially at the age of 40 it's very
young I think um so I took it really
seriously um they were like telling me
that I need to exercise more and they
wanted to put me on met foran um at that
and at that time it wasn't like kind of
known that met foran makes you live
longer yeah now it's very
trendy yeah now it's like trendy to but
like it was really scary for me at that
point I'm like I'm not going to go on on
like diabetes Med ready um so people
like micro doed out now
um but uh so I I um I found this program
called mastering diabetes which um is
like a health program with eating and
exercise um it's it's low oil like very
low oil all kinds of oil you can't
really have oil that's considered a
processed food so whole Whole
nonprocessed Foods um and um so I I went
on that and it was also vegan for a
while for like many years after that um
so that yeah that that that ended up
working and then I started doing a bunch
of weightlifting so I got a u yeah I got
a trainer that kept me
accountable um and then um you know I
did like the other things that people do
like I I got like na IV NAD but like I
don't think things work you know I did
it a bunch of
times yeah I did I did a bunch of those
things and I was like on Revol and a
bunch of these other things that just I
don't know I think I've like kind of
Whitted it down to one or two things I
take athletic greens every every day um
disclosure I'm an investor in athletic
greens but I take it every day it has a
thing uh you know has so I take that
every day and I take so it has like all
the multivitamin and probiotics in it I
take you know you know I take vitamin D
I take like a few things like that um
and then I do cold plunge and and sauna
pretty much and I work out I I I work
out I do weight weight training um but
like I I kind of like did six or seven
years of this like really extreme I got
to like 6% body fat at one point oh wow
U which was like even crazier than when
I was in high school not very
healthy I was like all my stats I had uh
continuous SCH close monitor like I did
like the whole thing right um but like
again you know it all consumed me
because I treated it like it was my
startup exactly that that's where I was
getting to because I think that's
exactly what happens to lots of people
they they focus on on their health with
the same intensity and fanatism as they
did on the business and in a way it
helps it's not bad but it's just a
curious phenomen I
find and yeah I mean years and people
get sort of lose interest burned out
they burned out of it yeah um yeah so I
don't do it as as extreme I did that I
did get burned out although thankfully I
didn't like let it all go I still work
out regularly and I do a few of the
things that I think are the most
impactful but um listen it's a it's a
fun Journey if if you like it and there
could be worse things that you do for
sure
absolutely I'm absolutely with you yeah
I I I guess I I I like to think about it
as as this momentum you know you spend
20 years going with full force somewhere
you create even bigger force and then
you just keep going with that Force
after you exit you have to send that
energy somewhere and uh sometimes people
just go crazy with investing before they
learn how to do it I made that mistake
and lots of people we know do but other
people Channel it into health and maybe
that's a big that's a better option if
you have to channel it somewhere it
should go to health probably than not a
bad thing to
do I mean if you do it overdo it on your
health it's not a bad thing for sure um
I think a lot of also um post exit
Founders let's just say post exit people
um they they have this false sense
of um thinking that just because they
had an exit that they're smart let's
just say in every other field of
everything that they do um true yeah so
that also that also um contributes to
like
this you know investing thing you know
where they where they make mistakes in
investing
um no absolutely it's like you you
mentioned you um your business would
have like 60 70% margin and of course
it's very hard then to settle for what
private bank Bankers advise you to do
there are no um there are no asset
classes really out there that you can
both control largely and have this kind
of uh return yeah you you end up taking
too much risk and just because like
let's say if you're in Tech you think
you know Tech right yeah and then you
conflate you conflate good Tech with a
good
business because those aren't
necessarily two good things right I mean
those are two two two um they're not the
same things um yeah 100% and and and I
guess you're you know yeah you're trying
to push the boundaries just like you did
as a as a as a founder and that doesn't
work out too well for you in the short
term at least with uh with with unless
you really know we we all learn these
humility lessons um there most of these
patterns and mistakes are quite
predictable if you talk to to enough
people so what would you say your main
humility lessons were so I took a
decision-making course during Co um so
if you think about it no one really kind
of like teaches you how to make good
decisions I've never taught that in
which is the most important thing we do
in life but no one teaches you 100% And
you know I went into this thing I I paid
like $11,200 for it um it's it's by this
guy named Shan Parish it's called a
knowledge project oh yeah yeah of course
yeah uh so so I listen to his podcast I
really like him a lot very smart guy um
and he has this course and I'm like you
know what I don't know let's I didn't
have much to do anyway during Co let's
just say you know and I'm like I'm going
to take this this this this thing and
whatever I went into it really arrogant
thinking that I'm a um like one of the
best decision makers out there and I
know everything about decision like what
is this guy going to teach me and I
realized that I really had no clue of
how to make a good decision and I wasn't
doing any of these things that I now do
a lot right yeah and um you know just
basic things of like even kind of like
categorizing the kind of decision that
you're making is this decision
reversible is it is it um is it really
important you know is it um you know or
you know is it binary or could there be
a third option that that solve your
problem um you know there's there's a
lot of um techniques that that you can
use um am I really finding you know do
you think about the second and third
order implications of any decision that
you might make right because you know
you might change something in something
that's working but you don't know like
you never think through what like the
implications might be that might have
adverse effects for you or or even
positive effects for you so
um anyway that that was a really you
know like kind of Moment of clarity for
me you were probably thinking how did
how did I create two super successful
companies and sold them without knowing
how to make decisions right no you you
really underestimate how much luck has
to do with it yeah it really does uh you
know I I think not that I was like like
I wasn't the worst decision maker like
of not you know but but I W but but I
certainly was not like let's say you
know a a really great one um that I was
able to do that so um I think you know I
I can tell you about like the 50 bad
decisions 50 bad Investments I made and
stuff like that or I don't even know um
you know a bunch of really stupid things
that I did in my businesses that I that
I shouldn't have done or that kind of
stuff that really kind of
you know brought me back to Earth um but
I'm curious about a post exit when you
you know had two successes you had all
the right to feel you know it all uh
then one amazing humility lesson you
just mentioned learning that you don't
even know how to make decisions I think
it's brilliant I love it I also took
took a course by Shane uh but it was on
mental models on creating mental models
I also thought it was very helpful yeah
I read his book
on they're really he's he's a I mean I I
think you know this is also
the you know this is also part of that
process
is if you can be really introspective
about yourself and and and be willing to
change that's a very good trait for any
investor and that's part of why I took
these classes and I and I was like
amenable to doing it is because I wanted
to kind
of you know making better decisions is
the same thing as like making better
investment decisions right not just like
you know your your your other decisions
that you make in your life and so I
wanted to really maximize how I did that
um and improve myself so um that you
know I think I think you know the
biggest humility thing was like I never
in my other
businesses um except for like my lawyers
and my accountants and stuff I never
really relied on
anyone let's just say um yeah and and
and so like when when it came to relying
on a wealth manager um that was a hard
thing too because
MH I don't know it's it's kind of messed
up to say but like I was like looking at
the guy I'm
like this guy's telling me what to do
and
like I just like you know I just like
sold this business and how does he know
better than I do you know what I mean
yeah of course I know exactly what you
mean Shane yeah so um I don't know you
know like I went through a bunch of
wealth managers and they probably all
thought I was a giant dick just to be
honest with you in the beginning so uh
but I had to change I had to change
because a first of all nobody would want
to deal with me and second I wanted to
learn from that person I had to bring
myself like you know bring that ego down
and be like this guy obviously knows
something that I don't know and like I
need to learn yeah or this girl or you
know I I say guy but you know I me I
mean guy or girl you know you know Shane
I've been researching the whole post
exit journey and talking to people for
13 years now and I came to to one
conclusion I'm absolutely sure of that
the root cause of all the mistakes is
just not taking that time to introspect
not doing it properly not doing it long
enough not doing it deep enough all
mistakes come from there so I'm so happy
to hear about you taking the decision-
making course and doing it actually that
explains a lot uh in terms of you now
being in a much happier place yeah I I I
appreciate that um yeah it's again it's
it's like willing to do what a lot of
people won't do right or they think
stupid um I mean it's tough it's tough
introspection is very tough especially
for people who spent most of their adult
lives um interacting with the reality
and making decisions fast and being very
action-driven and then
suddenly shifting our geese in inwards
is hard work very feels very unnatural
it's funny I listened to a podcast by
Sid Guru today I don't know if you
follow him but he's um he's really
amazing and at the end they were like
what do you
want everyone to like get from this it
was like a two-hour podcast it was live
right he was was uh giving a talk live
they're like what do you want people to
do after this and he's like well I can't
make anyone do but I want them to
realize that the only way out is from
within how do you want to be remembered
honestly just like as a good dad and
good husband um that you know made
people that other people like let's just
put it it that way uh that that you know
contribute to society and you know
people like to be around and make they
make other people feel good I mean I I I
I have no delusions that like anyone's
going to even remember me in a hundred
years from now because like I don't
remember anyone from 100 years from now
that was my ancestor so um you know it's
it's it's weird to think about it that
way but it it's actually like I don't
understand the concept of legacy and
those types of things because at the end
of the day really may maybe like now
somebody will remember you from like
Instagram or something I don't know but
even that will probably go away at some
point Jane this is so beautiful I'll let
you go so you can be a good person and a
good father oh thank you so much I
really enjoyed this thank you so much
thank you so much I loved it a lot a
great conversation great me too thank
you so much appreciate it
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