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The Scariest Moments in Business as an Entrepreneur


recently when I was at Harvard Business
School with 144 other entrepreneurs who
ran very successful businesses valued
from 100 million dollars upwards of four
billion dollars there was one thing
everybody had in common when we were off
and we were talking and we were just
chatting with each other everyone had a
horror story everybody had a story of
how close they were of going out of
business but I tell you everybody I mean
everybody had a horror story or at one
point they did and they had to make a
comeback every single person I will tell
you here for you watching if you have
any aspirations of running a very
successful business one they were being
very successful as an entrepreneur
yourself you need to know that it is
guaranteed you will face some scary
moments in business and you can’t
overcome them and that is one we really
find out what you really made up on
that’s when everybody finds out what
you’re made of just so you know that
anybody that you meet that successful is
able to face those horror stories and
overcome the membe one so I’m going to
share with you a few my horror stories
and hopefully you know this will shed
some light to you to realize you’re not
alone by yourself and other people go
through this as well most of them it’ll
be a few experience about I think like
11 or 12 of them that are personally
experienced one of them will be this I
think one of these scariest things one
of these scariest things in business is
when you declare your intentions to the
world that you’re starting a business
and every you have opposition 100%
no one believes you’re going to be
successful in business why because
you’ve never run a business before why
would they believe you’re going to be
successful in business and what I call
this experience is the i-told-you-so
nightmare let me tell you what’s the
i-told-you-so nightmare I cannot tell
you how many nights I went to sleep
sleepless nights I would have nightmares
about those people that told me not to
do it and I’m facing them and they’re
telling me I told you so I told you
should have never done this I told you
this isn’t gonna work out I told you so
who those nightmares were on
bleep painful let me tell you and these
i-told-you-so faces some of them were
relatives some of them were friends some
of them were enemies who said I told you
so and I’d wake up in the middle of the
night I can’t say how many times my
entire shirt is wet I’m in bed and had
to go to bathroom and splash some cold
water on my face and I’m just like it’s
just a nightmare it’s just the
nightmares just and I’m it’s okay it’s
okay go back to sleep try going back to
sleep I can do that
let’s get to work as I’m thinking about
to go out of business because someone’s
going to tell me I told you so it’s a
very scary moment in business you will
experience many of that it’s going to
happen but it’s just a part of
imagination it’s not a reality but it’s
going to mess with you another one is
this here’s another one another one is
when you actually start partnering up
with a company I remember one time they
hired me a startup hired me they did
technology products which was like the
next up-and-coming Yahoo and they were
based out of Santa Ana they hired me to
train their salespeople and I came
through and I brought on board a hundred
salespeople that was a training in a
Southern California marketplace and I’ll
never forget on a Monday morning I’m
going there to collect all the checks to
come and do a sales rally and give these
checks away to the salespeople
and Monday morning I’m going up the
elevator with the president guy named
Ray at that time I’m going upstairs we
knock on the door he puts the key into
open the headquarters he can’t open it
janitor comes and says they pulled
everything out over the weekend I’m like
what are you talking about we open it it
was as if everything was slow-motion the
door opens like a movie tanta everything
was pulled out except the logo so wait a
minute why some everything was pulled on
every checks that was uncashed every
check that was sitting on the table to
deliver to our sales force we went to
the nearest bank
nothing could be cashed it closed down
the checking account it was done we
couldn’t get a hold of the investor we
couldn’t get a hold of the founder we
can get a hold of nobody with that
company six months went out of business
that night I had to go to Conrad’s in La
Crescenta Crescenta Valley and I had to
deliver the fact that that company went
out of business in front of a hundred
people let me tell you that drive back
from Santa Ana
Valley with traffic which is about a two
and a half hour three hour drive was a
very difficult Monday night driving I
met with them some of you may even watch
this make sharing with somebody who was
part of that meeting that was not an
easy meeting but I had that night if
there’s anything I learned that night is
I learned how to toughen up and learn to
deliver bad news and I have to make
myself you think this is bad news what’s
bad news compared to this is if you’re
in the military and if you have to go
tell somebody’s wife with two kids
saying their husband just passed away
that’s bad news yours isn’t that bad of
a news had to go and go and deliver that
news and difficult time sleeping that
night I told responsibility I felt it
was my fault etc etc but I grew from
that moment delivering bad news to
company that I went out of business
now the scary moment is when you run out
of money I want you to think about this
here
imagine you start a company what every
single pin you have everything from your
insurance policies from mutual funds
stocks cash savings you know money fund
accounts you any any money market
accounts anything you can think about
lets you see have a million dollars you
start this company six months later
you’re down to a half a million dollars
nine months later you’re down to a
hundred thousand dollars twelve months
later you down to $13,000 you literally
have nothing left every credit card has
been maxed out and you only have $13,000
left and by the end of the week all your
employees your sales reps your vendors
everybody expecting a payment from you
and if you don’t pay them they’re going
to leave you and if you do pay them
you’re at a business you don’t have
money to pay your rent food anything
what do you do do panic what do you do
at that moment see I experienced that I
experienced that in October of 2010 let
me tell you what’s very scary very very
scary and you realize what things you
need to doubt a moment like the last
thing can you just panic you need to
figure out the next steps on what to do
but that is a very scary moment of
business that could happen
and you have to still figure out a way
to get out of a situation like that
which we ended up getting out of it and
good things started happening another
thing is a scary moment is when you
start a company to start up and
you don’t speak the language of a
company you don’t speak the language of
a start-up so I remember the first time
we started our insurance company a PHP
and I have no carriers I have no
insurance company right there paper none
none of them have said yes to me every
one of them I met when I spoke to they
said no to me because they said how long
have you been around I said one week
they said no so one guy got on a call
with he finally said um yeah who are you
with let’s meet in the next two months I
said no no I’d like to meet with you
today or tomorrow I’m in LA he’s in
Chicago he says oh you’re in town I said
oh yeah he says ok if you around
tomorrow why don’t we do lunch tomorrow
tomorrow 12 o’clock
I said no problem I get a flight that
night $1200 flight to go to Chicago from
LA I go to Chicago
twelve o’clock I go to meet him this
man’s name is Garth I shake his hand we
go upstairs one hour we speak one hour
later I’m leaving I have no idea what
he’s talking about half the words he’s
asking me I don’t know a lot of the
languages that he’s asking these
questions up I’m just having a very
sincere meeting with him says here’s
what we’re going to do here’s what’s
going to happen with our business he
shakes my hand this is a multi
multi-billion dollar company he says
we’ll give you the contract let’s get
the paperwork started right there I’m
like wait a minute this is really
happening yes it is I left trying to
control my emotions on how excited I was
as if everything was expected and I go
down since I’m like oh my gosh I cannot
believe I was able to get this
appointment and close it without knowing
half the words he asked me on what it is
to run a startup because we had enough
do you have this do you have that you
have this do you have that you have this
was your general counsel legal counsel
accountant are you crude are you this
are you dad
what’s your vector everything it was it
had no idea so sometimes scary thing is
you go into a meeting that the meetings
bigger than you how do you handle
meeting like that you can experience
some of those as well next one next one
was mix one was final straw of
negotiation let me explain to what I
mean by this this is when you’re
negotiating with somebody and you do not
have the leverage over the other company
so it is August of 2011 think about this
August of 2011 we’re about to go out of
business
PHP we’re about to go out of business
August of 2011 nobody knows this
I have no carriers no carriers one of
our competitors was going around you
know defamation of character whatever
you want to call it they were trying to
do whatever they can for every single
carrier to stop representing us everyone
dropped everyone said okay we’re not
doing business with them except for one
company and it was AIG was a gentleman
named Greg I met together with Greg we
had already known each other and we
started talking
I had no leverage we’re not doing
nothing we have nothing going on at that
time and he and I sat down and we had a
long conversation together than the next
level in the next moment I flew in and
we had meetings long meetings long
meetings with AIG and by the time we
were done they said yes I had zero
leverage in that negotiation it’s the
final straw if they say no
next week we’re out of business okay
next week we’re out of business
they said yes I went back I announced it
for the first 90 days it was absolutely
terrible nothing went the right way and
eventually we ended up writing more
index universal life with AIG three four
years in row than any other company in
the world
and it turned into a very very
successful relationship but I had no
negotiation leverage when I was
negotiating with these guys at that time
next one is when a big client changes
their mind this happens in sales a lot
for me it happened early on my sales
career when I quit my job and I went in
I remember had a salesman that I made
the sales call I made the Commission was
$11,000 $11,000 at that time was a lot
of money $11,000 was a lot of money to
me because that $11,000 I was already
counting my rent my car payment my debt
my phone every single thing you can I
went back with back in the days next
hell the way next to work I was 890
dollars I’ve had to pay that off
everything I was behind so I’m counting
on this 11,000 Auto check I leave the
house I’m so excited I’m relieved
I got breathing room again I go in
excited the next day and then all of a
sudden I get a call from the client and
you know you don’t want to pick up that
call because you know exactly what is I
pick up the client’s call
they want to change their mind what
happened we just want to change our mind
what happened my cousin who does the
same thing you do
he’s with the same company or with we
didn’t know he was with the same company
would we call them for advice because we
know he was in the insurance business we
have chosen to go ride with them but but
we totally understand we know what
you’re gonna say and his cousin prepped
them on everything I was going to say
sab no come back
$11,000 was a lot of money let me tell
you it almost put me out of business was
a very very scary moment that day as
well another one is when a big player
executive salesperson staff member of
your company leaves and it’s holding the
structure of business I’ve experienced
that before in the last 15 years of
being in business I’ve experienced that
a few times and every time it’s happened
it’s been a disruption and every single
time it happens you think you won’t be
able to handle it but every single time
it’s been handled but it has happened
when it doesn’t you’re in a moment it’s
never fun to experience when you lose a
great teammate another one is a lawsuit
listen lawsuits happen a business when
you run a business you do not want to
experience four lawsuits but sometimes
loss what’s happened especially the
bigger you get them one time we
experienced a lawsuit that was a
400-page lawsuit I will never forget
this form on a page lawsuit that came in
and they sued me the company seven of my
team members they wanted to do whatever
they could to put us out of business and
I was a scary moment when FedEx brings
you box this big and you open it up and
it’s a lawsuit from a four hundred
billion dollar company let me tell you
you need to realize that at that moment
they can do every single thing they want
to put you out of business
but they can’t do anything to stop you
from working and I was the biggest edge
anybody can sue anybody but nobody can
stop you from working especially in our
country maybe some other countries they
can you cannot stop the person from
working so you need to get back to work
another one is when investor backs out
some people have a startup company and
investor one day says we no longer want
to participate with your company that
happens many times with many people when
investor pulls out when it happens you
got a pivot and it can be scary
sometimes especially if you have some
picking on money they need to be paying
people it can be scary things that can
happen at times but you got to figure
out a way to pivot with that another one
is when your partner changes their mind
I had this experience with me seven
years ago
say and this was actually good friend at
that time and we were start a business
and when we were starting a business you
know we started off and I never forget
we’re at his house four o’clock six
months we’ve been talking about this
he’s excited in the basement he’s
shaking my hand I get I give you my word
to ideal you know boy I give you my word
we’re going to do this and we’re gonna
tap that that that up no problem wake up
fired up comes in town fired up
everywhere we go is excited the night
before the night before when I talked to
him you had to change your heart and it
threw me off tremendously the night
before and it was one of the best things
that happened because I learned that at
that moment you don’t necessarily know
if everybody has the courage to go and
do something like this and this person
did not have the courage to go do
something like this and a big part of
the funds that at that time we were
counting on was going to be a 50/50
opportunity for both when he pulled out
it threw me off tremendously threw me
out tremendously
and I almost didn’t make the decision
because my decision was almost
controlled by his fear and I had if I
would have said no that means I made my
decision based on him and I can’t
control this fear she has to live with
his fears when he’s 80 years old you
know for the next 30 40 50 60 years he
has to live with the decision that he
made and even though maybe a decision
publicly where people say you made the
right decision deep down inside you know
he has to know when having access to all
the information no matter how much you
Commission’s himself he know what type
of a decision he made I moved on but
that is not an easy decision when that
happens but it will happen in business
you can’t take it personally you got to
move on it’s business these types of
things will happen in business you still
need to move on it happens in sports all
the time Westbrook Durant it happens in
sports all the time with Shaq and Kobe
it’s happened in so many different
platforms you got to be able to stand up
and still go out there and win
regardless of what takes place the last
but not least when things happen that
you can’t control I got started in the
financial industry with Morgan Stanley
do it on nine ten
excited next days 911 I can’t control
911 from happening no one wanted to
invest for three years
no one everybody i sat with oh we don’t
know how to mark its gonna do because
we’re afraid that we’re still going on
oh we don’t know what’s going to happen
to the market we’ve taken every single
penny out of a stock market we’re not
going to know what’s going to happen
with it oh we’re not going to know we’re
not investing oh we’re not doing we’re
staying cash right now when everything
was cash and I’m starving for three
years
everything was cash everything was cash
and try to figure out during that time
it’s not something I control it’s
something that was happened to market I
still stuck around and I saw 95% of my
peers who got licensed there series
seven during that time they quit they
were probably smart at that time for
doing it but I had the courage to stick
around and I didn’t want to give up
because eventually I thought something
good was going to happen and it ended up
happening so every one of these stories
I’m telling you I’m not telling you
these stories with the intentions of
scaring you this is not an intention for
me to scare you or tell you for you to
oh my gosh I don’t know if I can handle
going to becoming a sales guy for a
company or a executive or part on or an
equity on or an entrepreneur or whatever
it is not at all I just want you to know
that this is normal I know this sounds
crazy but this is normal and this is
where your defining moment happens this
is when you learn about yourself this is
when you go home at night and you kind
of experience what cold feet is all
about this is when you go home at night
and you tell yourself I made the wrong
decision I should have never done it
that person was right I told you so was
right whoever that I told you so it’s
these are the moments where you become
the person that everybody looks up and
you become the example to everybody else
or you become a statistic that allowed
fear and any of these horror type of
situations that are temporary gets you
to go out and quit and not become an
entrepreneur you’re going to have to
make that decision for yourself I won’t
have to you can have to do it the good
news is for the most part there’s a way
out for the most part there’s a way out
when you’re experiencing these types of
things that happen in business so
anyways with that being said Paul go
grab my pillow from your body I know you
got the Paula sitting there comfortably
we got an exciting project that’s coming
up for
our trip okay here we go
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stories about the scariest moments
you’ve ever had in your career please
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