Secrets of Post-Exit Happiness

Summary

In 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

00:00

🚀 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.

05:01

🎓 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.

10:01

💡 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.

15:02

📈 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.

20:03

🔄 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.

25:03

🤔 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.

30:06

🧘‍♂️ 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.

35:07

💼 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.

40:09

🏠 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.

45:12

🏋️‍♂️ 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.

50:13

🤝 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.

55:15

🏡 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.

Keywords

💡Investor

An investor is someone who allocates capital with the expectation of generating a return. In the context of the video, Shane, the interviewee, had to transition from being a business operator to a good investor after selling his businesses. This shift required a different mindset and skill set, focusing on financial growth rather than day-to-day operations. The script mentions, 'I had to learn how to become a good investor,' highlighting the importance of this role in his post-business life.

💡Operator

An operator in a business context is someone who manages and oversees the day-to-day activities of a company. The term is used in the script to contrast the hands-on, active involvement in a business with the more strategic, less hands-on role of an investor. Shane mentions the difference between being a good operator and a good investor, indicating that the skills required for each are distinct and that he had to adapt after selling his businesses.

💡Nightlife Business

The nightlife business refers to commercial activities that take place during the evening and night, such as bars, nightclubs, and entertainment venues. Shane's first successful business, Junebug, was a software platform for the nightlife industry. The script discusses how Shane saw an opportunity in this sector due to outdated systems and created a platform that became the industry standard, illustrating his entrepreneurial acumen.

💡SaaS (Software as a Service)

SaaS refers to a software delivery model in which software is provided over the internet, on a subscription basis. Shane's company, Easy Texting, is described as a SaaS business in the script, highlighting its growth and profitability. The success of Easy Texting as a SaaS platform is a key part of Shane's entrepreneurial journey and his eventual transition to investing.

💡Exit

An exit in business terms refers to the strategy by which an entrepreneur or investor leaves a company, typically through a sale or initial public offering (IPO). Shane successfully 'exited' two businesses, Junebug and Easy Texting, which is a significant milestone in an entrepreneur's career. The script mentions his reflections on the process of exiting and what it means for his future.

💡Burnout

Burnout is a state of chronic stress that leads to emotional, physical, and mental exhaustion. Shane discusses experiencing burnout due to the constant stress of running his businesses. The script reflects on the impact of burnout on his decision to sell his business, 'I had just met my current wife... I wanted to have a family... it was my burnout.'

💡Delegation

Delegation is the act of assigning tasks or authority to other people. Shane talks about his attempts to delegate tasks within his business to alleviate his workload. However, he found it challenging to let go and effectively delegate, as indicated in the script, 'I tried to delegate and... I just wasn't too good at it just to be honest.'

💡Wealth Manager

A wealth manager is a professional who provides financial services to help clients grow, protect, and manage their wealth. Shane mentions finding a wealth manager who was willing to teach him about investing, which was crucial for his transition from entrepreneurship to investing. The script states, 'I found initially a wealth manager that was willing to teach me,' emphasizing the role of mentorship in his learning process.

💡Mindset Shift

A mindset shift refers to a change in one's mental attitude or perspective. Shane had to undergo a significant mindset shift from a builder's mindset to an investor's mindset. The script discusses this challenge, '...learning how to shift your mindset into an investor's mindset versus a builder's mindset is very different.'

💡Decision Making

Decision making is the process of selecting from among alternatives, often based on a set of criteria or preferences. Shane's investment in his own education by taking a decision-making course reflects his commitment to improving this skill. The script highlights this, 'I took a decision-making course during COVID... I realized that I really had no clue of how to make a good decision.'

💡Humility

Humility is the quality of being modest and not overly proud or self-assertive. Shane's realization about his own limitations in decision making and his willingness to learn from others exemplify humility. The script describes this humility lesson, 'I went into it really arrogant... and I realized that I really had no clue.'

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