Rob Basso - The Exit Plan

When history major turned business titan Rob Basso wrapped his resume in a sandwich to score job interviews, little did he know it was just the appetizer for an extraordinary entrepreneurial feast. Journey with us as Rob recounts his flavorful tales of launching ventures, the emotional weight of selling them, and the fulfilling yet challenging dance of work-life balance. His candid anecdotes serve up a hearty meal for thought on how unconventional strategies and a dash of creativity can be the secret sauce to a successful life and career.

Embark on a rollercoaster ride through the high stakes of business deals with an entrepreneur who has navigated both the adrenaline rush of signing deals and the bittersweet moments that follow. Rob opens the vault to his experiences with selling companies and the introspective aftermath, sharing the personal impacts and the insights on strategic negotiations. Meanwhile, we take the scenic route around topics like private jet ownership, the perception of wealth, and grounding oneself in the face of luxury's lure.

Lastly, Rob's narrative isn't confined to boardrooms—it strides into the nuances of raising a family amidst affluence and the evolving dynamics of entrepreneurship across generations. We travel through the emotional landscapes of an entrepreneur's life post-exit, the pertinence of work-life harmony, and the empowering leap from corporate chains to the freedom of entrepreneurship. It's a dialogue that stretches beyond the horizon of business, offering panoramic views of the human experiences that shape our individual and collective journeys.

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Episode Transcript

Speaker 1 (00:01):
Alright, rob Basso, are you okay with being recorded
on a podcast?
Absolutely, oh shit, there goesthat liability.
This is, I Took a Hike.
I'm your host, darren Mass,founder of Business Therapy
Group and Parktime WildernessPhilosopher.
Here we step out of theboardrooms and home offices and
into the great outdoors wherethe hustle of entrepreneurship

(00:21):
meets the rustle of nature.
In this episode, we take theenergetic path alongside an
entrepreneurial achiever withRob Basso.
Our topics include the hustleof a true go-getter, the
creative CV strategies for thatfirst real-world job, the
emotional highs and lows aftermultiple successful exits, plane

(00:43):
ownership and the value of apurposeful life.
We are filled with energy,descending alongside a vibrant,
successful leader, and I Took aHike with Rob Basso.
This episode is sponsored byDeFi Supplements.

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will defi your expectations.
Alright.
So, rob Basso who are you?

Speaker 2 (01:43):
That is a good question, and why do you start
with the difficult ones?

Speaker 1 (01:47):
Well, because if they were easy, then this wouldn't
be fun.

Speaker 2 (01:49):
Well, first off, I'm a dad.
I've got two kids my son, nick23, and my daughter, skyler's 20
.
They both live down in Tampaand they're loving life.
My son's working on hisprofessional career.
My daughter took a little breakfrom school and figuring her
world out, and I'm just excitedto know that they're doing well
and trying to be happy,productive citizens of this
world.

Speaker 1 (02:09):
That's good.
It's hard to be a dad, right.

Speaker 2 (02:12):
It's harder than I thought it would be.
To be quite honest with you,you always have the best
intentions, you have kids and atthe end of the day, you get
some of it right, you get a lotof it wrong and most of the time
they survive pretty well.
As far as professionally, it'sjust a very interesting story,
just like probably a lot of theentrepreneurs.
I was a history education major.

(02:32):
I went to Hofstra Universityand everybody's like you were a
history major and you ended uprunning businesses and building
them and selling them.
I'm like, yeah, and they wonder, well, what was your training?
How did you do that?
And at the end of the day, Ilearned how to communicate.
I learned how to get my pointacross, and this is synced,
clear fashion and that's what Ifound is mostly what runs good
businesses is that greatcommunication with your clients

(02:53):
and your staff.

Speaker 1 (02:54):
That's right.
And do you finish up all yourstories by saying the rest is
all history?

Speaker 2 (02:58):
No, did I say that?

Speaker 1 (03:01):
No, it would be true, you could have that one.
All right.
So you were a history major,and I think this is pretty true
for most people out there.
They don't end up working inthe major that they studied.
I think I might be the onlyperson going to school for
telecom and then going totelecom, but here I am
interviewing you on a trail.

Speaker 2 (03:18):
But that is the beauty of this world that we
live in, and there is no setpath.
Listen, if you were choosing tobe an accountant or an attorney
or a doctor, a lot of timesthose folks continue down that
path.
But I could have just as manyfriends who became lawyers and
never practiced a day in theirlife and just use the skills
that they learned in law schooland they used it in their next
career.

Speaker 1 (03:36):
All right, so you did not go into history.
Where did you go?
I did not.

Speaker 2 (03:40):
I did not know what I wanted to do and I was working
in a deli in an office buildingbecause I needed to pay rent.
My dad was good enough to payfor my college, but when college
was over, that was it.
I basically got a couple monthsand I was completely cut off
and I looked back and I was noteven mad at that.
I knew that that was the way itwas supposed to be.
So I was struggling, livingwith probably five friends in a

(04:00):
really shitty house somewhere inLong Island in a bad
neighborhood and working in thisdeli.
And it was in an officebuilding.
So people kept coming down.
I said you know, all thesepeople go to work every day.
What do they do?
So I wrapped my resume in allof the sandwiches yeah, you did
it.

Speaker 1 (04:15):
I can still picture it.

Speaker 2 (04:15):
Yes, I did, no you did it and I didn't know what I
was doing.
I said I could literallypicture them pushing the mustard
aside.
No, you did it, I did.
Wait.
You printed out your resume andwrapped it in the sandwiches
along with the rest of theirmeal and I must have got four or
five different job interviews.
That could be the mostingenious.
Maybe if your listeners hearthis, they'll start doing it and
they'll get jobs out of college.
All right, I'm flabbergasted.

(04:36):
That's ingenious.
Well, I didn't know it at thetime.
I was desperate to be quitefrank with you and I said how am
I going to meet these people?
And you know, I had the dirtywhite apron on for making their
lunches and I got a bunch ofinterviews there and I almost
had a pick of which jobs I wantin marketing or sales.
So this one awesome woman shegave me this job and two weeks

(04:57):
before I was supposed to startshe came down and I saw the look
on her face and I knew beforeshe said a word we had budget
cuts, I can't hire you.
So even at that young age Ithink I knew it was very
difficult to go back to theother few that I got offers.
By the way, your choice numbertwo, it's just so.
I didn't Okay, what was the roleit was in the marketing
department.
It was like a junior associate,low level beginner rep in their

(05:18):
marketing department.

Speaker 1 (05:19):
So you were a history major working at a deli in an
office building Wrapping your asthe kids say CV.
We've gone backwards it's now aCV In ham sandwiches.
That's an interesting role.

Speaker 2 (05:34):
Well, it gets more interesting, though, because I
didn't remember I didn't takethe job because she, she
couldn't offer to me because Ihad budget cuts.
So three weeks go by, I tookanother part time job, but she
called me out of the blue andsaid my husband owns and
operates a payroll and humanresources company.
Now, to be quite frank, Ididn't even know what that was
because I'd always been paid incash Really didn't know from
taxes at that particular momentSorry if the IRS is listening at

(05:54):
that point in my career, mylife, it wasn't a thing.
And then I said, okay, I'llinterview with them.
And then I interviewed withthem and that's how I got
started in the industry that Ispent 25 years in.
And what industry was this?
I was in the payroll business.
So I owned a payroll companycalled Advantage Payroll
Services for 20 years and we didpayroll and HR.
You've probably heard ofcompanies like Paychecks and ADP

(06:15):
.
We were direct competitors ofthese huge multi-billion dollar
giants in the New York region.
And how?

Speaker 1 (06:22):
many clients did you have Almost 4,000.

Speaker 2 (06:24):
Wow.

Speaker 1 (06:26):
How did you get your clients?

Speaker 2 (06:28):
Mostly by doing.
What we're doing now is havingconversations and part of the
challenge when you're a smallguy going up against the big
dogs especially when you'retalking about online marketing
or Google AdWords or things likethat they were buying up all
the really and making it almostunaffordable for the little guy
to do any kind of pay-per-clickback in the day.
So we had to do it theold-fashioned way and go and
make relationships.

(06:48):
So what we did was we maderelationships with CPAs,
accountants and financialadvisors and became
indispensable to them byconnecting other types of
business to the things that wedid and when they used us, we
act as the hub of their entirebusiness process and we became
invaluable and we were very goodat it, fortunately, and I hired

(07:09):
really good people to do thingsthat I sucked at.

Speaker 1 (07:13):
So many important themes here, so one you
essentially became a connector,a relationship builder between
CPAs and I'm sure there weresome back-and-forth referral
relationships.

Speaker 2 (07:20):
There was the best of what we could.
But you know the funny thingabout that is they always wanted
it to be that way the CPAs andthe attorneys Because I did so
much business with other CPAsand attorneys it was very
difficult for us to do that.
So what we tried to do with, wetried to lead with the fact
that we're just going to makeyou look good.
Yes, our price is a littlebetter, but I never sold on
price, I sold on value.
Yes, which I'm sure in yourworld was sometimes challenging,

(07:42):
because Telcom is a verycompetitive industry and it was
a lot price-driven, if Iremember correctly.

Speaker 1 (07:48):
Yes, you're right, but we would sell on value,
because when everyone else isselling on price, there's always
someone willing to be cheaperand cheaper.
If you're not cheap enough,then eventually quality suffers.
So I learned at an early age toalways sell quality over
quantity and always sell qualityover pricing, because as a
small company, if you're solelyfocused on being the cheapest,

(08:09):
you're not going to have enoughmargin to grow.
You won't grow your processes,you won't be able to hire the
right people.
We're the best people that youcan afford, the best equipment,
the best this or that, andtherefore that will hurt you a
lot.

Speaker 2 (08:20):
We did little things, darren.
Like, yeah, we had clientnumbers because we had so many
clients, but generally when theycalled we went by their company
name.
They really knew who they werespeaking with and at the end of
the day there was some enddecision maker they could get
ahold of me.
Now, when you get that manyclients, I could not speak to
every client, even if I wantedto, but the ones that were
significant enough that therewas a big enough issue, I never
worried about getting on thephone, and I think that's a big

(08:41):
challenge.
Nowadays, people hide behindtheir email and their texts and
think that that's sufficient.

Speaker 1 (08:45):
Believe it or not, it's okay.
Now it's about instantmessaging.

Speaker 2 (08:49):
The answer has been 37 seconds.
It does make it morechallenging for, I think, the
younger generation, becausepeople's expectations are
different.

Speaker 1 (08:56):
And look at this view Wow.

Speaker 2 (08:58):
And we did that in like 25 minutes.
Wow, this must be the highestpoint in New Jersey.
New Jersey's flat is aboard.
No, there's a high one.
We're not done yet.
Yeah, we're not done yet.

Speaker 1 (09:05):
And there is a place called High Point.
I believe it's 2800 feetelevation, which is the highest
point.
Wow, this is perfect.
Northern New Jersey, and I havehiked it before.
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Tell me what it was like whenyou had your first signed

(09:49):
contract in the payroll business.
How did that feel like?

Speaker 2 (09:53):
I remember it pretty clearly too.
And here's the thing In my mindI knew that I was going to get
30 more that quarter and I justknew it.
I just really felt that.
And it might sound like crazytalk, but the truth is I signed
that first one, and now it'sdifferent.
So when I signed that first one, I was like when am I getting
my next?
It wasn't, oh my god.

(10:13):
Amazing job, rob.
You started this business.
You've never met these peoplebefore.
They signed this contract andthey let you in their bank
account Like who would do that?

Speaker 1 (10:19):
There was no celebratory.

Speaker 2 (10:20):
No, I was 22 years old and it's like no, what's
next?
How am I going to pay the bills?
So now I have to say, aftermany years, I do celebrate the
small wins and probably by thetime I was in my mid to late 30s
, I started celebrating a littlemore, because otherwise, if
you're on that constant drive,you never feel satisfied with
your life or what you have orwhere you've been.
And it did take me a while, butI don't even want to say that

(10:42):
I'm there yet, darren, but I'mgetting there.
Listen, when I started figuringout what I wanted to do after,
I sold my businesses so thefirst big one I sold was an 18.
And I built another one quickly.
The first one I sold to apublic company.
The second one, I also sold toa public company.
And then I was like what am Igoing to do with myself?
And I had all these things.
I'll do this, I'll do that.
The truth is, I didn't knowwhat I wanted to do.

(11:03):
How old were you?
It was 2018.
I'm 51 now.
So Congratulations, yeah, thankyou.
You don't look a day over 51.

Speaker 1 (11:10):
That's so sweet.
So how old were you when yousold the first company?
48.
48.
Was it a good exit?

Speaker 2 (11:18):
It was life altering.
Life altering, you know.
Yeah, don't have to work everagain if I don't choose to, and
could do what I want when I want.
I've also determined thateverybody's number is different,
so others would say, oh, thatwas a really good exit, but jeez
, I need triple that.
And here's my answer to thatGood for you, and I don't care
what you want or need.
I know what my life needs to be, so I'm very happy with what it

(11:39):
was.

Speaker 1 (11:40):
All right.
So first exit was great.
It was to a public company Verycreative.
That's a great question.
Can you say the company or not?

Speaker 2 (11:45):
Yeah, it's a company called Paychex.

Speaker 1 (11:46):
Oh yeah, I heard of them.

Speaker 2 (11:47):
I licensed a piece of software that helped me run the
business.
They bought that software in2012.

Speaker 1 (11:54):
Is that how they discovered you?

Speaker 2 (11:55):
Well, no, not quite.
It was like getting hit and hitwith the brick, because we
assumed that was the beginningof the end, because they would
either be pilfering it, raisingour prices, pushing us out of
business, because they wantedthe market, and most of that
actually did transpire.

Speaker 1 (12:08):
You and I just to pause in for a second.
You and I think very much alike, because the company I sold my
telecoms to, windstream, boughtup all of my competitors, who
were also my vendors, and Ithought the same way, which is
why we had to sell the companybefore it's time.
I knew that they would figureout a way to gouge or pilfer.

Speaker 2 (12:26):
So I was in the same boat, but here's maybe a modest
difference.
I was ready anyway, so thestars aligned where I was ready.
I had done it for a long time.
I wanted to do other things andI knew that was coming, and the
multiples in that industry wereeither at an all-time high or
close to an all-time high.
So I knew that if it wasn't now, I could be in a struggling
situation three years, and Ididn't want to do that.

(12:46):
So we negotiated the deal,which was an incredibly
challenging situation, becausethese public companies don't do
things the way you and I mightdo them, as you probably well
know negotiating with Windstream, and unfortunately, they all
say stuff to your face in theboardroom.
By the way, that's cactus.

Speaker 1 (13:02):
Oh wow, that's prickly pear cactus Really Up
here yeah.

Speaker 2 (13:08):
How is that possible?
I don't know.
Are you sure that's what thatis?
That definitely is.
I think it actually is.
I don't know.

Speaker 1 (13:12):
I'm not touching it, but Listen, I don't know why,
I'm just shocked.
How is there prickly pearcactus up here?
Oh, that looks pretty cool.
The cold of New York and NewJersey.

Speaker 2 (13:20):
It looks a little Sorry.

Speaker 1 (13:21):
ADHD moment.
There we go, let's get backSquirrel, squirrel.
It's funny.
That was the joke in my office,me too.

Speaker 2 (13:27):
You and every successful entrepreneur that I
know Squirrel.
So you know they said things andthen the negotiation right to
your face and then they'd comeback the next day and be like I
never said that.
Yeah, you know, basically youknow that was their tactic to
negotiate, but at the end of theday I ended up negotiating a
deal for myself and a bunch ofother people that licensed this
particular piece of software andwe all exited around 100

(13:49):
million bucks Wow and Wait, thatwas your exit.
No, no, I wish it was.
Mine was a very significantlyhealthy share, because I was the
biggest, you know, licensor.
Wait a second, guys, Hold on,Look at the city.
Oh yeah, that is an amazingview.
I've never seen that before.

Speaker 1 (14:03):
Someone else at a squirrel moment?
Wow, wow.

Speaker 2 (14:06):
Yeah, all right.
So you know they made itdifficult, but at the end the
deal closed and it was anall-cast deal, no holdback, no
provision for losses.
No holdback, they just wrote acheck for a wired rate of money.

Speaker 1 (14:24):
I should say, and for those not in the know, the
holdback period is the amount orpercentage of the sale, usually
between 10 and 20%, that thebuyer will hold back in the
event that the seller has somesort of catastrophic loss in
customers revenue Something wasnot coming to fruition that was
promised or earned, ornegligence in reporting et

(14:46):
cetera.
Yep, typically, the holdback isgone.
It never goes, or rarely, ifever, goes to the seller.
To the seller, yeah.

Speaker 2 (14:53):
Well, that was my second deal.
The second deal didn't go atquite as planned but, you know,
at the end of the day, these,you know these, these other
individuals trusted me to helpnegotiate the deal, you know,
with Paychecks.
And it's not just because I wasthe largest licensor of this
particular piece of software.
I just think that they, theytrusted me and they knew that I
had strong capabilities and Ihad their help.
I didn't do it all on my own.
I was the, the person in chargeand the final say.

(15:16):
But at the end we all had toagree on the number and I had to
do some internal selling to getthem, some folks, to agree.

Speaker 1 (15:22):
So you were the consummate salesperson, and that
is also the making of a verysuccessful, hustle-minded Long
Islander.

Speaker 2 (15:31):
Yeah, yeah, I guess you're probably right, and I
have friends that areoperationally-minded, that also
have successful businesses, butthen they hire great sales.
Yes, you know.
So they figured out a wayaround that.

Speaker 1 (15:39):
There's one really it's very challenging and I
don't want to say it'simpossible, but it's very
challenging to be both theoperations-minded person and the
sales-minded person.

Speaker 2 (15:46):
I was okay at the operations Like left brain,
right brain, yeah, I mean, likeI said, I think I ran a really
good operation.
But my vice president ofoperations was my old boss at
the first payroll company Iworked at and she came with me
which was mind-boggling, likeshe left this good, cushy job to
go with a 22-year-old kid LikeI still can't believe this day.
She worked for me the entiretime I had the business.
Of course she saw something, Iguess.

Speaker 1 (16:05):
Of course I still can't believe it, but she did.
I mean, I think everyone hikingalong with us can hear it.
You have this swag about you,this hustle, this grit, and if
we all collectively think backto our greatest bosses, our
greatest managers or leaders,they all have had that.
They've all embodied thatquality Someone who could talk
the talk.
Now, if you pair that withdoing the right thing, right For

(16:25):
your people, and caring aboutthem and nurturing them and not
being a jackass in business,then people will follow you.
Because what?

Speaker 2 (16:31):
are they doing?

Speaker 1 (16:32):
They're aligning their success with yours.

Speaker 2 (16:34):
Do you have this feeling too?
Sometimes, though, I don't wantto use the word imposter
syndrome about myself, butsometimes I still feel like do I
still have it?
Yes, can I still do this?
And why are people listening tome?

Speaker 1 (16:44):
Well, welcome to the episode of.
I took a hike where it's everysingle one where I say why are
people listening to me?

Speaker 2 (16:49):
Yeah, but yet they do .
And you get up every day stillwondering that.
But I honestly think if we feltanother way, we'd have this
horrible arrogance aboutourselves.
Yeah, they keep you in check,but, by the way, people do.
I know plenty of people thatprobably nobody should be
listening to, because I thinktheir advice is stupid and
they're stupid and they justhave this supreme confidence and
it's like I don't even knowwhere that comes from, because
you suck, you won't see me onthe private jet with my

(17:11):
champagne with a bunch of girlsand you're like you're not going
to see that on my social media.
First off, I don't do that, butsecondarily, it's just.
I just think it's disturbing.
But people do it and peoplefollow it because they want to
be like that for whatever reason.
And then they realize when theyget there it's like that's not
what it's really, like you knowwhat I mean.

Speaker 1 (17:25):
I agree with you.
I've never wanted to own aplane.
I've wanted to be on a plane.
Oh, I did.
I had a jet for a few years.

Speaker 2 (17:30):
That's actually the truth, but I didn't have
champagne and girls and allkinds of nonsense.
Having your own private planeis pretty fucking awesome.
It was a little expensive inthe.

Speaker 1 (17:37):
Everett event.
Well, what kind of plane was it?
It was a Lear 55.
That's a real jet.
Oh, it was a real jet.

Speaker 2 (17:42):
No, no, it was a real jet and I flew my friends all
over the place and we all had anamazing time.
But you didn't see that on mysocial media.
I'm telling you that here, butthe reality is you want to know
about me, so I'm telling youabout my life, but that's a
piece of private life for themost part.
And my friends would go onvacation.
I'd get everybody there andthey'd put the bill for
everything else.
It was not a fair financialtrade off, but it's what they

(18:02):
could do and it was awesome.
We had the best time.
We went to go see one of myfriends worked for one of the
owners of the Milwaukee Bucks.
I flew everybody out to a Bucksgame.
We got a tour of the wholestadium.
We got to meet the players, thepresident of the club.
Yeah, we could have done thaton a commercial plane, but it's
a shitload of funer flying inyour own.

Speaker 1 (18:17):
So I leased it out.
But I leased it out though.
So I think many people do that.
They buy it, they expense it ona business and then they lease
it out for a profit center.

Speaker 2 (18:25):
Plus the tax situation 100% of it was
depreciable year one.
So whatever you paid for it, ifyour income was big that year
you paid half.

Speaker 1 (18:32):
Oh really, yeah, oh yeah, oh, that's pretty nice,
yeah, so we made a wrong turn.
The trail is actually overthere, so here we come down.

Speaker 2 (18:38):
We could probably make it up that way.
It's up to you guys Up this way, right.

Speaker 1 (18:43):
So what is it like owning a private jet?

Speaker 2 (18:46):
You know, it's just like you see on TV.
Here's the man.
I was literally talking to myfriends yesterday.
He's like man.
I need to find more friendsthat have private jets, I was
like yeah, well, I'm sure you do.

Speaker 1 (18:55):
Well, I understand the importance Now.
I worked for a company wherethe CEO did the same thing, had
a private jet on the company,leased it out on this person,
Right Yay.
But that was the downfall ofthe company because the people
then saw it as an arrogant move.

Speaker 2 (19:11):
This was after I sold the company, so there was
nobody that I cared about foryou.
I would not have done it whileI owned the company.
I would not have.

Speaker 1 (19:16):
So here's the thing, though, is you have to
understand the importance Now.
This CEO needed to be in eightdifferent places in one day.

Speaker 2 (19:23):
Well then, it was a necessary thing.

Speaker 1 (19:24):
So if you actually break it down, in that sense it
makes sense, because we all knowthe struggles of going to an
airport.
You're in for a solid two hoursplus Listen you drive up.
You can't do that if you haveto be in three or four different
cities in one night.

Speaker 2 (19:34):
It's just like you see, you drive up, pull your car
up, they take your stuff outand you get on the plane and you
go and you're never late.

Speaker 1 (19:39):
It's your plane, they're going to wait for you.

Speaker 2 (19:40):
It doesn't matter.
That's right.
But financially, mathematically, it wasn't worth it, unless you
are committed to understandthat it is going to cost way
more than you think it's goingto cost.
And you have to have that costappreciation, enjoyment factor.

Speaker 1 (19:54):
Well, the deal is not to be worth it for you to
support flying to all the places.

Speaker 2 (19:57):
It was for four years and then it wasn't.
And I'm like, ok, I had my fun.
Does it get old after a while?
No, it never gets old, really,I never even hear the thing.
I never even been on a privatejet before I bought it.
So the brokers, like mostpeople, fly private for a while.
I'm like is there anything badabout it?
He's like well, I guess I seeyour point, but the point is I
don't miss it.
It was a phase of my life.
I don't need to ever have itagain.
What did the cost look like?

(20:17):
Well, the plane probably was $3million bucks and it probably
cost a million and a half toupkeep every year.
Ok, plus staff.
Well, I had two pilots, that'sinclusive and then I leased it
out and made back probably themajority of it.
It still cost me probably aquarter of a million a year.
So I mean, if you have a decentamount of money, it is not

(20:37):
incredibly painful, but if itwas your last penny, I highly
don't recommend it.
No, and listen, at the end ofthe day, I'm getting my pilot's
license right now.
I should have it in about threeweeks and I'll rent for a while
and then I'll buy a share inthis little prop plane that I
want, and then my goal in threeyears is to be able to fly this
little single engine jet I havemy eye on.
But that's not about theswankiness, it's about the
accomplishment.
I hope I never read about youin the news.

(21:00):
I hope not either.
But starting the business,though, there was a part that I
think would might be interesting, because I didn't just get into
business.
I had some folks that believedin me when I was trying to
license this piece of software.
In fact, they wanted me to workfor them and open up the Long
Island office.
And I said I don't want to workfor you, I want my own business

(21:20):
.
They're like well, we're notgoing to do that.
You can work for us or there'sno deal.
So I made the deal, but it wascontingent on the fact that they
would allow me to buy thelicense to the software back if
I had certain metrics.
They never thought I was goingto do it, and I did.
And then I had to pay $50,000for the business that I bought
back from them, not even a yearlater.

(21:40):
No way, yeah.
And they weren't bent about it.
They knew they had to stick toit.
Wait, wait, wait.

Speaker 1 (21:45):
So you have a Barstool Sports Dave Portnoy
situation here.
Probably You're the originalDave Portnoy.

Speaker 2 (21:49):
Oh, maybe I'm a little older than him.
You know the story right.
I know parts of it.
I don't know the whole story.

Speaker 1 (21:53):
He sold Barstool Sports for like I don't know
what was it, guys, fact, checkme.
$500, $800 million Good forDave, something like that, and
they basically gave it back tohim for free Because they
couldn't figure out how to runit.
Right, the PEs couldn't figureout how to run it.
It was nothing without him, andthe only thing he had to do is
agree that if he is going tosell it, the PE firm has the
first right of refusal toparticipate in the deal.

Speaker 2 (22:13):
Oh, he'd be fine with that.
What did he care about that?
Probably the end of the day.

Speaker 1 (22:16):
Well, he's now worth between $500 to a billion
dollars and he said I'm neverselling this again.
Yeah, but he gets to live it.
This is great.

Speaker 2 (22:22):
Good for him.

Speaker 1 (22:23):
You got to free half a billion dollars.

Speaker 2 (22:26):
I mean, you know, there's just that story alone
and just watching BarstoolSports just come to be, it's
just mind-boggling, it really is.

Speaker 1 (22:33):
Political aside, his hustle and grit is admirable.
I agree Because, much like you,nobody can stop you.

Speaker 2 (22:39):
You know.
But the thing is, you believeand this is what I think, I
think it's this false narrativethat it can be you, and I'm not
trying to dash people's hopesand dreams.
But you know, it's like yousaid, it's like me being Michael
Jordan.
It's just, I can have thatbasketball in my hand all day,
every day, and it's never goingto happen.
It would have never happenedfor me.

Speaker 1 (22:54):
Michael Jordan was Michael Jordan because there are
certain genetic gifts that makeyou just better with whatever
you have your mindset.
That's true.

Speaker 2 (23:00):
And you know, I saw something on Steph Curry, who's
obviously one of the King ofThree Pointers, and I think they
said he shoots 500 baskets aday, a day.

Speaker 1 (23:08):
A day.
So that is just a constant.
You need to constantly be at itand you know there's no other
thought about it.
But that's also dangerous too,Because how many other Steph
Currys have been out there thathave had their hopes and dreams
smashed because they dedicatedsolely to one thing?

Speaker 2 (23:24):
I think I'm more realistic with my kids and you
know, the funny thing is, Idon't know.
I don't remember a time wherethey had an outward, maybe when
they were very little, theywould make comments like that.
But you know, in general I thinkI've been a very realistic
individual, but I think the hardpart that I'm finding with my
kids now is they've lived a lifethat I did not live.
Yes, and that's what I said, Ican't relate to my kids.

(23:45):
My kids are wealthy, yeah Well,and it's a little weird for me,
and you know when they have acertain attitude about something
or they're very grateful andthey're very hardworking.
But I just think they're prettyclear now there's no
expectation that they're goingto get anything other than my
support and they need to do iton their own.
And my son has found that outin the last few years and he not

(24:07):
only is fine with it, he wantsit.
He wants to be able to show meand himself that he can succeed
on his own.
And yes, maybe later on, afterthey're more established and
whatever, I will share more ofthe stuff or the things that
we've accumulated as a family,but I don't see how it does them
any good right now Talk to meabout running a business.

Speaker 1 (24:25):
What were your biggest challenges?

Speaker 2 (24:28):
I think one of the biggest challenges was keeping
myself in check and knowing whento be the good boss and
understanding and have theproper attitude, know when to be
really tough and make yourpoint known, and I think that
balancing act is really hard,that combination of loving and

(24:49):
hugging and supporting to.
You know, I don't want to usethe word reprimand, but be
difficult to the point wheresomeone's not going to make it
on your team.
They self-select and they leavebefore they get fired.
And that might seem harsh butit's worked for me and I think
it's worked for a lot of otherentrepreneurs.
You have to have the right skinthickness, I think, to work for

(25:09):
most entrepreneurs, because weare a little erratic.

Speaker 1 (25:13):
Well, it's part of the job.
You're working on 50 differentthings at any given time.
What was one of the mostdifficult days running a
business?

Speaker 2 (25:22):
Probably one of the times when it was Superstorms.
Stand to stand in the New Yorkarea.
For those that are listening,from Wyoming we had a big storm
here a bunch of years ago and itwasn't quite a hurricane but
wreaked havoc in Long Island Ithink they couldn't?

Speaker 1 (25:36):
Oh, is it?
The insurance companies wantedto list it as a hurricane For
some scandalous, nefariousreason for not paying out.

Speaker 2 (25:44):
All of that happened, all of the above, I'm sure how
New York we lost.
This was a building I owned andwe lost power, I don't know.
So there's multiple phases ofpower lines coming in there and
we lost one of the phases comingoff the line.
So only half the outlets worked, and we didn't know which ones.
Myself, everybody, wasscurrying around trying to get
power to things.
Half of our equipment worked.
We couldn't plug everything in,and this was before.

(26:05):
I had a new modern buildingthat I bought a generator in,
and you have these visions oflosing all your clients by not
being able to do the job.
Oh, if you can't run payroll,well, we didn't pay.

Speaker 1 (26:15):
There's pitchforks coming at you.

Speaker 2 (26:17):
Tens of thousands, 100,000 people not getting paid
when they probably needed themost because of this storm.
And we did it and we gotthrough it.
But, conversely, one of myproudest days was 9-11, when
they closed all the bridges andwe drove all the payrolls for
our city clients to the edge ofthe bridges to pick up their
actual checks.
Believe it or not, most peoplestill like a live check,

(26:39):
depending on the industrythey're in.
They don't like direct depositwhatever.

Speaker 1 (26:43):
But you know you did it, but you had a duty to do
that I think we did.
No, that's one of those wherefailure isn't an option.
You have a duty to do that.
So I suffered through HurricaneSandy or sorry, not Hurricane,
whatever we're calling it.
I faced that Hundreds of myclients were out of business.
They were out of service.
What means out of business?
At that moment I could relateto that.

(27:03):
That was one of the toughestmoments.
I remember getting on my bike.
I lived on the Upper West Side.
I got on my bike, dodge treesand debris, got downtown to Wall
Street where our office wasWent to work Right, and you
probably didn't think twiceabout it either.
No, not even a thought.
It's the hero, it's the fightor flight, it's the engage when
called to action.

(27:23):
No is not an option, you justdo it, but in a way that became
one of the best times of mycareer and my understanding of
what a real CEO shoulddemonstrate.
Yep.

Speaker 2 (27:37):
And your staff watched it.
They might not have saidanything, but they knew what was
happening.

Speaker 1 (27:40):
No, they said it Because when you have to reflect
on those moments, when the dustsettles, you have to say, wow,
that was rough.
That was tough.
Nobody gave an excuse.
We were all hands on deck.
I'm proud of everyone and samething it's a bit of advice for
anyone who works for a companywhich is everyone Tell your CEO
they're doing a good job whenthey deserve it, because
everyone needs a pat on the back.

Speaker 2 (28:01):
I guess, to follow up your first question, the
hardest emotional day was theday after I sold the first
business in 2018.
Why is that?
Because it was this culminationof my entire career and it was
over in an instant and the moneydidn't make me feel any better.
You would think it would, andeverybody assumes it would.
At that moment it didn't.
I was quite depressed for awhile.

(28:22):
It's like wow, ok, I got somenumbers and some zeros behind it
Digital zeros.

Speaker 1 (28:28):
Yeah.

Speaker 2 (28:29):
But that's even a whole other thing.
It's like it's not a thing youcould touch or feel, it's just
whatever.

Speaker 1 (28:32):
But for me it was very difficult.
The intangible that you weretold is your life's purpose.

Speaker 2 (28:36):
Yeah, which I think after, and some of your
listeners might not be at thatpoint yet and hopefully they
will be after listening to yourstage advice, but the truth is I
like what you did there, buddy,you like that.

Speaker 1 (28:45):
That was cute.

Speaker 2 (28:46):
But you don't know until you're actually in that
situation and everybody says, oh, that's bullshit, the money you
should be happy, and it's not.
If you really think about thehuman condition, that's not what
it is.
So that was really a hard dayand my wife was like why are you
upset?
Well, I'm not going to get tosee the people that I work with
for 20 years on a daily basisever again.
So I was losing that communityin a heartbeat and I thought it

(29:07):
was really difficult.

Speaker 1 (29:08):
Did you feel like you betrayed your employees?

Speaker 2 (29:11):
Yeah, in a way I thought about that quite a bit,
but mostly that was weeks ormonths afterwards and I had
private conversations with folksBecause the day that I made the
announcement was a day that thetransaction took place.

Speaker 1 (29:25):
There was just the way it gets done.
There's the gear in theheadlights.
What do you mean by that?
How could you do this to?

Speaker 2 (29:29):
me.
I might assure everybodythey're going to have a job.
They're like we don't believeyou, we don't believe the new
people, and it's like peoplewere crying.
It was very difficult.
Did you come through?

Speaker 1 (29:37):
with your promise of everyone being employed.

Speaker 2 (29:38):
Every single one of them not only got employed, some
of them made more money.

Speaker 1 (29:41):
My man audible high five.
Yeah, let me tell you, oh, thatwas a good one, that was a good
one, that was, that was healthyit was very important to me,
but there was no way I couldknow for sure that the buyer
would actually do it.

Speaker 2 (29:50):
The only thing I had going for me was that we had
such a low attrition rate ofclients.
Why would they get rid of thesepeople?

Speaker 1 (29:56):
And you know what they didn't.
There are the whys right.
Synergization of lots of thingsincreases profitability and a
buyer, strategically, could wantthe most profitability.

Speaker 2 (30:05):
Some of them got better money because these big
public companies have thesepaydans and scales.
They might have been paid wellfor my world, but then all of a
sudden they get this $10,000increase and they were fairly
modest paid people, Tina, whohad worked for me for 20 years
like Rob, this is the best thingthat ever happened.
I'm going to miss you, but youknow I just got a huge raise and
I was like oh, good for you,and we still talk to this day.

Speaker 1 (30:23):
Yeah, so that's amazing.
So you and I are very alike,right?
Does that happen a lot on your?

Speaker 2 (30:29):
show, or does that not happen as often as you would
think?
Which part that people that youinvite on the show are alike,
or sometimes they're wildlydifferent?

Speaker 1 (30:35):
There's something alike about successful achievers
, right?
It's a mindset, it's thathealth, mind body connection.
It's the doing the right thingfor the right people.
I wouldn't invite you on a showcalled I took a hike if I
didn't want to spend timelearning from you, right?
And the people who I like arenot the ones flashing the
diamond rings, they're the onesthat actually give a shit about

(30:55):
their people, because that's howI built my career.

Speaker 2 (30:57):
I left my diamond rings in the car just so you
didn't see them.

Speaker 1 (30:59):
Oh, that's good, just so you know, you did come to a
waypoint.
Your car might not be there.
It's my wife's car.
She'll be pissed.
That's cool, not my problem.
See you.
By the way, I got jokes, I cantell.
I can tell I'm also a punchykid from Long Island.
So let's get back, because thisis a subject you are really
meandering, aren't we?

(31:20):
It's ADHD and whatever.
I got a joke about the drumside I triedomen to.
Let's get back to how we relate.
The show is all aboutdepression, a massive depression
.
After exit, depression beunspoken.
So talk to me about that.
What did that road feel like?

Speaker 2 (31:35):
You know, I think originally I felt like I
shouldn't feel like this.
I felt that I was almost mad atmyself for not being elated and
not realizing that this couldbe possible, even though people
told me it could be possible.
So I think I felt a littleangry with myself, like this is
stupid, Rob, why do you feelthis way?
And then, after weeks andmonths of really trying to

(31:57):
unpack the last 25 years of mylife, it made it a heck of a lot
easier.
But I understood why.
I was upset and it's kind ofwhat we briefly touched on
earlier that my world had justcompletely got blown up and the
things that I thought, my entireidentity was wrapped up in my
business world and even myfamily, I don't want to say took
a backseat, because that's nottrue.

(32:17):
It was different and I didn'tsee myself as that.
I was this entrepreneur,business, people that people
looked up to, and then, withoutthat business, what was I?
And even multiple years later,I still miss it.
I still miss that game.
I hustle in a very differentway now and I'm being OK with it
, but it's very hard to put intowords, even though at the

(32:39):
beginning of the show I said Icould be clear and succinct and
get my point across.
This is really hard becauseit's really deep seated in your
brain about who you are and whatyou think is important in this
world.
And that's what I spent thelast few years doing trying to
figure out what is reallyimportant to me and what am I
going to do with the next decadeof my life that's going to make
me feel important to the worldand fulfilled for myself not
even for other people for myself, what would you say the number

(33:01):
one, the biggest trait that youmust embody as an entrepreneur
that is poised for success.
I would say, the ability to dowhat seemed like benign things
over and over again, so theeasier.
Put your stick to it in thisyear.
Just your undying labor of loveto do things that most other
people disdain, to get where youwant to go and have that
ability to do the repetitiouswork like a bodybuilder or a

(33:24):
weightlifter would, to get upevery day and do those reps.
Because I look back at mycareer and I probably was not
good at a lot of things, but Ijust literally kept cranking it
out consistently on a dailybasis, year after year, even
when I didn't want to do it.
And I think if you don't havethat trait, it is very difficult
to be successful in nearlyanything, would you agree?

Speaker 1 (33:44):
entrepreneurial traits.
Business acumen is wildlyuniversal, oh, absolutely.

Speaker 2 (33:48):
Yeah, no, I completely agree, and there are
a million examples from my life,and I'm sure yours, which back
that up.
I don't care what the businessis, that's how I'm able to do my
business coaching.
So I went back and I gotcertified to be a certified
business coach and I've got avery nice client base where I'm
helping on a weekly basis and Idon't know specifically anything
about their industries but it'snot urgent.

(34:09):
I actually went on.
A new client said well, you'venever worked in this industry,
how could you possibly help me?
And I love that question.
I had an answer but, to bequite frank, I didn't give him
this long drawn out answer.
It was very brief and I got tothe point and said this is why
and he hired me.
So I believe that someonethat's run businesses and been

(34:30):
successful or even moderatelysuccessful can walk into
somebody else's business prettyquickly and assess the
challenges, issues and problemsthey might be having and outside
of math and human emotions,facial expressions, businesses.

Speaker 1 (34:45):
among the most universal languages, p&l is a
P&L.

Speaker 2 (34:48):
That's exactly right.

Speaker 1 (34:48):
Profit loss, top funnel, bottom funnel, it's all
universal.
You're right, you might notknow specific industry details,
but that's where we askquestions, lots of questions on
your normal discovery call right, that's right.

Speaker 2 (35:01):
I still enjoy those.
It's still fun.

Speaker 1 (35:03):
What would you tell somebody who is maybe your son's
age says I want to be abusiness owner one day.
I'm an aspiring entrepreneur orCEO.

Speaker 2 (35:11):
And you know, fortunately I've got a chance to
like Stony Brook University inHofstra.
They asked me to speak to thebusiness school, so I've had
these opportunities and the funpart is, you know, you get to
really listen to what they wantto do and most of the time I
tell them I said, just beprepared that it's going to be
harder than you ever imaginedand it's not for everyone.

Speaker 1 (35:30):
Not forever.

Speaker 2 (35:31):
And you know they look at me like that's insane.
Of course I'm going to do this.
I said good for you.
I said but it's OK if it turnsout not to be, you know, and
kind of like we were talkingabout before.
It is not for everybody for amillion reasons, which would
take a whole other show.
But the simple fact is I don'twant to dash people's hopes and
dreams like you talked aboutwith your daughter.
You were being realistic and Ithink if I was doing my job
right for these young buddingprofessionals to tell them what

(35:54):
I really feel, not the hopes anddreams story that their parents
tell them.

Speaker 1 (35:57):
Do you think kids these days are soft?

Speaker 2 (36:01):
That's a loaded question.
Do you want me never to be ableto hire a 25-year-old?

Speaker 1 (36:05):
anymore.
I've got you about two milesinto this trail with 40 minutes
to go.
So now the good question iscoming up.
The answer is the short.
You eat the spicy hot wing.
Just to shut me up for a fewminutes.

Speaker 2 (36:16):
The short answer is I don't know that soft is the
right word.
Only because I don't want to bederogatory, not because I'm
afraid to say it, but becausetheir world is just very
different than mine and yourswas.
And I think it's no differentbetween the millennials and then
you know, obviously I'm a Gen X, and then you've got
millennials and the Gen Z andall the other.
They've grown up in a vastlydifferent world than we did and
I think their vision of theworld is so different that we

(36:38):
don't have a choice but to dealwith the fact that they're wired
completely different.
Trying to make them what we areor what we want to be is not
nearly impossible.
I think it's impossible,impossible.
So to say that they're soft, Iwould say that they don't have
the same realistic vision of howthe world works that we
probably did at the same age.
Do you think that's a goodthing?

(36:59):
No, I don't necessarily thinkit's a good thing.
I think it's a much harderthing for them to.
They're going to get hit in thehead a lot harder than we were,
even with the reality of life,and I think most of them will
change their tune when theyrealize it's not what they
thought it was going to be.

Speaker 1 (37:10):
I remember this conversation back.
I'm a Gen X as well, I think bylike very short period time.

Speaker 2 (37:14):
Oh, I'm dead in there .

Speaker 1 (37:16):
I was born in May of 80.
So I remember hiring my firstmillennial and then I remember
the whole talk was howmillennials they don't want to
work, they expect to be the vicepresident from day one, making
vice president salary.
Blah, blah, blah, yada yada.
I didn't buy any of thatbullshit, although I did
regurgitate some of the sayingsjust to fit in Right.

Speaker 2 (37:36):
That's what good entrepreneurs do with chameleon.

Speaker 1 (37:38):
But I didn't buy it.
I enjoyed it.
I'm hiring millennials becauseI liked that mentality, just
like you and I.
Everything was possible, right,you didn't want to work for
authority because you wanted tobe the authority.
You didn't trust morons, right,and that's kind of what they
were saying.
But it is interesting how, whenyou speak to millennials today,
some of them refer tothemselves as geriatric

(37:59):
millennials.

Speaker 2 (37:59):
That's because they don't want to be associated with
the millennials.

Speaker 1 (38:02):
Yes, because they actually turned out to be of the
same cut as we did in Gen X.
It just took them a little bitlonger to get there, you, don't
think the greatest generationcomplained about Gen Xers, of
course they did.

Speaker 2 (38:12):
This is also just what it is.
Listen, I hired a millennial.
That was literally just likeyou said.
I did this one project.
Well, I want to raise.
I'm like you've been here sixweeks.

Speaker 1 (38:20):
You just started doing it.

Speaker 2 (38:21):
You're lucky to have a pencil and then they quit
because probably their parenttold them you can't take that.
You did that project, whichblows my mind.
But then my assistant,christine, who was a millennial
because the hardest workingperson, one of the hardest
working people I've ever met.
So it's dangerous asstereotyping.
Well, that goes with anything.
That's why, when you asked methat question, I tried to answer
it carefully about theirsoftness.
Because not because I didn'twant to hurt anybody's feelings,

(38:42):
but because I didn't want tosound like a typical Gen Xer
that just moaned about theyounger generation that
everybody does.
Truth be told, I like hurtingpeople's feelings.
Yeah, that's what your kidstold me.
They were texting me saying mydaddy hurts my feelings.
No, I'm going to let that sitfor a second.

Speaker 1 (38:58):
Let's give it a brief moment.
We lost Apollo.
It's a brief moment of support.
Okay, apollo Creed.

Speaker 2 (39:07):
Oh right, oh I'm sorry.
You lost me for a hot second.
There I'm like yes, CarlWeathers did pass away.
I did hear that.
Yes, Apollo, my 88.
I lost you for a second.

Speaker 1 (39:15):
I caught up quick.
Okay, so I like strategicallyhurting feelings.
I don't thrive on it, butthere's some time that you need
to tell somebody, strategicallyyou can't do something.
Oh, I agree Because that if youare the right person, you will
have a fire lit under your buttas vengeance or prove me

(39:37):
wrongedness that will propel youto drive forward, just to do
the exact opposite.
I think that happened with meon multiple occasions.

Speaker 2 (39:45):
I think that is a great point and a great story,
and I was, when you werethinking, hurt somebody's
feelings.
I didn't know what to expectfrom your story, but I think
I've done that.
But I think I've done that andnot realized that I wouldn't
have told it the same way.
You know me.
That's just saying being verydirect.
You didn't do this.
Well, if things need to change,blah, blah, blah, you know yeah
, I've hurt somebody's feelings,but I never thought of it that
way.

Speaker 1 (40:03):
Well, live in a world today where we have the
illusion of feelings iseverything.
Everyone is inclusive, I'msorry.
Not everyone's a winner.
No, that's entirely true, noteveryone's a winner, and that's
okay, because not every one ofyou.

Speaker 2 (40:13):
I'm not a good bowler .
You don't want me on yourbowling team.

Speaker 1 (40:15):
Oh man, I was going to play your bowling next.

Speaker 2 (40:17):
You know so.

Speaker 1 (40:18):
I'm not good at that, yeah, but you're admitting it.
You are understanding yourweaknesses.
But if I asked you to gobowling, I took a bowl.
Would you do it?
Of course, there you go.
You're willing to try it.

Speaker 2 (40:27):
I took a bowl.
Wait a minute.
What are we talking about?
Are we still talking aboutNaked?
Rob understands that one.
Just don't call the way I betyou, if you called it I took a
bowl or I took a bong, you mightget triple your listeners.

Speaker 1 (40:39):
So yeah, or I might get some portafilter business.
There's so many facets to thisone, but no, it's when it comes
to feelings.
I think another marker of areally strong leader is someone
that is willing to just come outand say or have difficult
conversations An employee is notdoing the work that they should
.
Having that conversation rightaway in private, criticized in
private, right, Facing that andnot being afraid to hurt

(41:02):
feelings but boost that personup at the same time.

Speaker 2 (41:05):
I agree, but you know so, like my daughter.

Speaker 1 (41:07):
Realistically, you're not going to be the first
female MLB.
You're not practicing everysingle day and I don't see you
doing everything about baseball,right?
So, yes, play baseball.
I will support you, I'll throwand I'll pitch to you.
Absolutely, we'll put you onthe team, absolutely.
But when it comes to focusingyour life not happening, we're
going to find something else.

Speaker 2 (41:27):
You said something about calling out in private and
not in public.
I agree, except sometimes inthe sales meetings where you
couldn't really you couldn'thelp but there'd be a
competition in the room, withyour sales team sitting there in
your meetings and Competitions.
Well, that's calling out,whether you did it or not, or
they did it by their own lack ofability or effort.

(41:47):
That's the simple reality isthat when you're in sales
specifically, the numbers don'tlie.
You could be the nicest personin the world and everybody could
love you, and even the referralsources or your clients could
love you.
You sell two deals and yourgoals are 10 every month, or
whatever it is.
You're not going to be employedvery long.
That's right.

Speaker 1 (42:05):
Getting warm.
Now we are on the final stretch, probably about a half hour or
so, going on how we make it Nice.

Speaker 2 (42:13):
This is a perfect leisurely walk.
That's kind of a joke.
It wasn't leisurely, no.

Speaker 1 (42:16):
I was breathing heavy while I was talking.

Speaker 2 (42:17):
I was doing most of the talking while we were going
uphill.
I think you planned that yeahdon't give away some drinks.

Speaker 1 (42:22):
Tune in every Tuesday for a new episode of I took a
hike, posted by me, darren Mass.
So let's jump back intobusiness.
You said you had sold a secondbusiness.
Yeah, was that the businessthat you acquired back for
$50,000?

Speaker 2 (42:34):
No, no, no, that was the beginning of the career.
That was the one that I boughtat the beginning, was the one
that I sold in 2018, the big one.
So while I was negotiating thedeal to sell my first business,
I had realized what was going onand I wanted some soft landing,
so I peeled some of the clientsoff and moved them to a
different operating system inthat same industry.

(42:55):
Now I know what you're thinkingand the rest of your listeners
are thinking.
Well, why would the buyer ofyour original business allow you
to do that and allow you tocontinue to stay in business?
You must be a clairvoyantbecause I was thinking that,
yeah, this is not my first rodeo.
And the truth is, I'd love tosay that I was such an amazing
negotiator that I negotiatedthem to say well, this is what

(43:16):
it is.
You want my business, I gotanother one that does exactly
what I'm doing.
Too bad for you, let me do it.
It's not quite what happened,but at the end they agreed and
they let me stay in businesswith my other business, directly
competing with the one I justsold, and I don't think that
happens often, if that's ever,it happens incredibly
infrequently.
Well, this is what I thinkhappened at the end of the day.
I think they realized that atsome point they'll buy that one,
as long as I couldn't stealthose clients back, which I

(43:38):
wouldn't do anyway because it'snot ethical, you know, all right
, you're just pipeline for ouracquisitions.
That's what I think they neversaid it, but they let me do it.

Speaker 1 (43:47):
On the way it's future proofing.
You've already done it onceYou've created the successful
venture that they wanted toacquire, and I'm sure they're
not idiots, right.
They're working in Fortune 500land on purpose.

Speaker 2 (43:57):
Right Now there are $3 billion.
They might be Fortune 100.
I don't know where they're at.

Speaker 1 (44:00):
Yeah, they're pretty big.

Speaker 2 (44:01):
But then the second one.
So I had some clients and Ibuilt that and then I really
realized I'm like it was muchsmaller but still significant
enough.
And another public company Ireached out to.
This looks like a great dealand they said we want you to
come run our sales department.
So I took a job.
That's a whole story, but Itook the job running this other

(44:22):
public company sales department.
Did you enjoy?

Speaker 1 (44:24):
taking a job.

Speaker 2 (44:26):
Ha, ha, ha ha.
Listen my friend said you won'tlast a month.
Here's the thing.
I lasted nine months at a sheerwill.
It didn't work.
I left.
I'm still under an NDA.
I can't talk about myexperience there.
When I can, I will, but you canonly imagine what transpired

(44:46):
and why I left.
But I have to tell you I have atremendous amount of new
understanding of people thatwork for corporations and why
and how they get in a setsituation that I will never,
ever do again.

Speaker 1 (45:00):
That I can completely relate to.
It's a different world.
But it is also the main reasonwhy most of the business owners
are exited within a certainperiod of consultancy time
Because it is very hard totransition from being your boss
and doing things your own way.
In fact, when I was working forFortune 500, several executives

(45:22):
and board members had said tome on numerous occasions well,
it seems like we should be moreentrepreneurial.
And that was basically likethem saying bless your heart, ha
ha ha, it's funny.

Speaker 2 (45:32):
You just said bless your heart, because I was
literally talking.
Now that I live in the South,that's like a thing you say when
you're like yourself.
I did not know that.
No one's actually said that tome other than this conversation,
but I didn't know what thatactually meant when somebody
said it.

Speaker 1 (45:45):
Yeah, it's like a very sarcastic.
You don't know what you'retalking about.
Good way to shut you up andsound nice.

Speaker 2 (45:50):
Well, just in general , people that do what we do, and
then it's like a New Yorkerhigh five minus four.
They get asked when you take theposition or whatever and this
is just generic.
We're going to let you do this.
We're hiring you for yourskills, we want you to transform
, and then they don't let you doanything that you talked about
when they hired you.
So it's like that story isplayed out a million times in
the corporate culture, in thecorporate world.
Fortunately, you and I andhopefully soon to be a lot of

(46:13):
your listeners or some of themthat are already in our boat
don't have to make thosedecisions to work for these
companies that don't reallyappreciate them.

Speaker 1 (46:19):
Yeah, I mean.
It's a choice.
We have lots of choices in thisworld.
Now I'm in the camp.
If you follow me on LinkedIn,lots of my posts talk about get
out and do something on your own.
If you're sitting at your deskstaring at your glass trophies,
wondering why life is wrong anddepressing, then go make a
change.
More so than ever, we all havethe power to start a business.
Become a 1099 for the very samecompany we work for.

(46:41):
Do something on your own,create.

Speaker 2 (46:44):
What do you think about the whole just gig economy
in general?
Quit your corporate job andhave three different jobs.
I do this.
I'm a carpenter and I also knitfor a living and I also consult
on acquisitions.
Like people do stuff like that.
You're OK with that.

Speaker 1 (46:59):
Yeah, I love it.
Well, it's a little different,though.
I think the scenario you justposed you're describing someone
who has to work to feed theirfamily.

Speaker 2 (47:06):
Right, I talk about regular, everyday people that
want to go out on their own.

Speaker 1 (47:09):
If you have three different industries and jobs,
then you're clearly doing thisbecause of a financial scenario
in your life.
Well, what do you think about?

Speaker 2 (47:16):
people that you meet out at events and they give you
one card.
I sell mortgages, oh, and Ialso work for the sales
organization, oh and I also dothis.

Speaker 1 (47:22):
That bothers me actually, Because how can you be
an expert?
You're not concentrated.

Speaker 2 (47:24):
I built my whole career on being an expert in a
particular field and that's howI built my reputation.
And I find that when you'recorrupted and you have multiple
things going on and they saythey're really awesome at all
these things, it just can't be,unless you're a savant.
It just can't be.
So I don't trust them to doanything if they don't do the
one thing really well.

Speaker 1 (47:40):
So I am with you on that.
I love the fact that themessage is create something of
your own, become a solopreneur.
I think you and I will probablyagree on this.
But we'll see.
Having employees is daunting,challenging.
It's an emotional ride.
Your bad employee's bad day isyour bad day.
It is the toughest challengethat every employer has to deal

(48:00):
with and face.
It is hard to motivate people,especially when they're in a
funk, and it could be a companykiller.
It's a risk to have employees.
Yes, it is.
I think you could de-risk veryeasily by being a solopreneur.
Some of us have the capabilityof having a conversation with
our boss, manager, businessowner and saying hey, listen, I
want to do this on my own.
Are you okay if I leave?

(48:21):
Take the risk off of your plate, mr Business Owner, hire me
back as a 1099 consultant.
I'll give you a similar amountof hours, but now it's under my
time.
Huh, right, that's a greatmessage for a business owner.
You're de-risking Now.
Obviously it's not so black andwhite, right.
Right, there's some challengesthere.
Some business owners want tohave that employee, they want to
have that control, or feel likethey have the control, control,

(48:41):
the drug Right.
And then others, um, hold onreal quick Drow.
We're going this way, I guess.

Speaker 2 (48:47):
Oh, I will tell you that Others, others would be
okay with that because it isde-risking the business, but you
do lose that exact scenariohappened with me, and it at
several times, and one time itworked out swimmingly well and
he went off and did his ownthing and eventually left
completely and started his owndirect competitor.
But we worked out such a nicearrangement in a financial
situation where nobody got hurt.
It was good for him and nowhe's got a very successful

(49:09):
business on his own and I feltgreat about it.
We're still buddies now.
Another time it didn't work sowell, um, but same as employment
Right Right.
So your employee's shitty day isyour shitty day, yeah.

Speaker 1 (49:18):
But your vendor's shitty day doesn't have to be
yours.
That's right, that's exactlyright.
Right, but there is that aspect.
That's a pretty straightforwardcase.
And then there's the other casewhere it's you're just in a
dead-end industry.
You're not happy, you want todo something else.
I think, more so than ever, youcan create your own personal
brand strategy and turn it intosomething if you have that
desire.

Speaker 2 (49:38):
I mean, you know, I look back at all the personal
branding that I've done and thepersonal marketing between the
you know speaking engagementswhere I created this little show
, back before the internet waseven barely doing any of this
stuff.
It was just called BASALONbusiness and I went out and
fixed businesses and now youcan't turn on the TV without
seeing a business fix at show.
Listen, the production qualitywas okay.
It was okay, but I tried, andwhat I would do is I'd have a

(49:59):
lunch called Working Lunch withRob.
I'd show the little sevenminute episode, we'd talk about
current events and I'd get ahundred people to show up.
So I was it had nothing to dowith my payroll business Zero.
It had to do with theexcellence in business.

Speaker 1 (50:10):
Excellent business.

Speaker 2 (50:10):
Yeah, I love that and that's what I've tried to build
my career around, because Ididn't want to get pigeonholed
as the guy that owns a payrollcompany, because what does that
even mean?
You?

Speaker 1 (50:17):
know.
So yeah, no, I'm with you.
It shows more talent from youand it also is a great marketing
tool for clients.
Right, Absolutely.

Speaker 2 (50:25):
I interviewed my clients.
By the way, you know, theyloved the attention that they
got.
Well, clients today.

Speaker 1 (50:31):
Let's look at today the gig economy.
Right, let's go back to thattopic.
Today more than ever, yourpersonal brand as a CEO is your
stock to closing the deal, toattracting clients.
When I was doing marketing forthe telecom company, the
marketing people would say,darren, no one gives a shit
about you or the CEO of atelecom company.
They care about what thecompany will do for the customer

(50:52):
, for them.
Today, it's almost the opposite.
Today, people are buying.
If they align with you, theylike you.
Because the realization is whydo I want to make that clown
rich?

Speaker 2 (51:03):
Well, especially with what I'm doing now and how your
career has progressed and we'redoing some similar things, some
different things I would notget a client unless they aligned
with me and saw that I had animage that fit their world, that
believed that I could do.
Even if they've never met mepersonally, they'll go and look
at all the stuff out there,that's, and if it doesn't fit
their world, they're not goingto hire me.

Speaker 1 (51:21):
That is exactly correct.

Speaker 2 (51:23):
So when you tell clients you need to have a
better social media presence oryou need to have, and they look
at you like you're a deer in theheadlight.
You know it's not about.
You know, are they going toclick on that one Instagram post
and hire you or buy you?

Speaker 1 (51:35):
That's I'm not talking about Instagram, I'm
talking about LinkedIn.
Well, LinkedIn is the mostimportant, critical networking
tool that has ever existed, andif you're not on it right,
you're not going to put it likethis.
If you were hiring for asalesperson, they were applying
for the job and their interviewwas going very good.
You now do a background checkbecause it's worth it.
If you found that thatindividual that just tried to

(51:57):
sell you on hiring them had 77connections and never posted a
thing on LinkedIn, wouldn't thatnot track?

Speaker 2 (52:04):
100%, and I think what most employers do is
they're not supposed to takecertain things into account, but
they do.
I don't care what the law isand what they're supposed to do
I mean, who's not going to lookat their LinkedIn page and so
forth and you know.
That's just what people do.
You do a particularly good jobat it.
I have half as many connectionsand followers that you do on
LinkedIn.
You don't put in the time, thenI don't and I freely admit, and

(52:25):
there's a number of reasons whyI don't but the reality is just
like we talked about earlier.
You're getting the play and theconnectivity and what you want
out of it because you arededicating the time, energy and
effort, and I'm sure there'ssome days where you just don't
feel like doing it and you'redoing it.

Speaker 1 (52:39):
There's a lot of days I don't feel like.
So it's interesting, it's likeeverything else.
It's the dopamine rush.
You know, I'll have a post, dovery well, and it's all day.
I'm on there until my wifemakes a comment to me and she
goes I didn't see you all day.
What do you mean?
I hung out with you all day.
No, you're in the same room.
Yes, you weren't with us.
You were present, but youweren't present.

Speaker 2 (52:57):
See, what's a little different, darren, is I am not
going to do that this timearound and I'm not judging you
at all.
I just I'm trying to do thisdifferently.
I'm putting the effort in thatI think I need to do to get the
return that I need for what Iwant.
Your needs and wants areprobably different than mine,
which is typical.
That's just people havedifferent needs of want.
I want to be as well aspromotion, but I want to be as

(53:18):
busy as I want to be, but I alsodon't know that I want to have
30 people working for me againright now.
Or you know, I like the pacethat I have now and it also
allows me to say I want thatclient.
Oh, I don't want that one.
Yes, like I'm not.

Speaker 1 (53:29):
I'm not vibing with them, I'm not doing that.
So now you have earned theright to put up that big poster
that says I became a businessowner to only do the things I
wanted to do.
Now, that was before, but nowyeah.

Speaker 2 (53:41):
Right now.
But I mean, listen, I thinkthere's a.
There's a, there's a happymedium for someone who has like,
because you're supposed to havea personal brand.
I think I know we're talkingabout entrepreneurs and business
owners, but for those that arelistening, that work for a
company and maybe thinking aboutgoing on on their own or never
go out on their own, they stillneed to have a personal brand
within their own organizationand people forget that.
I have friends that work forthese big companies.

(54:02):
They don't exist in the worldyet they have these jobs and
they get paid.
Well, nobody knows who they are, nobody knows where it's like.
I think it's bizarre.

Speaker 1 (54:09):
Yeah Well, having having come from the industry
that has massive layoffsconstantly, it's a routine thing
.
There are so many people thatwork their lives off.
They've been at that companyfor X amount of years 10 years,
20 years and they don't havethat personal brand and they
don't have that direction afterthe layoff.
Yep, you've dedicated.
You know it's like you knowthat age old's factory worker.
I've been here forever and nowthere's no factory.

(54:30):
What do I do?
We are literally on the finalstretch.

Speaker 2 (54:33):
You have made it.

Speaker 1 (54:34):
We did, we did you went up a mountain, down.
We did.
This is a cool little bridge.
Wow, what a beautiful.
Yeah, this is actually glacial,this bridge.
Is it really?

Speaker 2 (54:40):
Yeah this bridge was deposited by a glacier.
Let me get one on our camerawith me and you.

Speaker 1 (54:45):
So how would you say your journey has been along this
trail.

Speaker 2 (54:47):
I'm a little out of breath, which is good, so I got
some good exercise.
Seriously, I enjoy theconversation because you don't
get a chance to have this longof a conversation with most
people about the things that youcare about, about the things
rattling around in your brainthat either people might want to
hear or might not want to hear,but you want to talk about and
I, for me, bouncing interestingconcepts and off off of people

(55:08):
that are like-minded but havetheir own perspective on things,
is probably incredibly valuableto anybody listening to this,
whether they agree with me,agree with you, don't agree with
either of us, that's, to me,the interesting part, and they
can still enjoy the conversationbecause they're going to get
something out of it.
Whether they buy into whatwe're talking about or not is
almost irrelevant.

Speaker 1 (55:26):
So, rob Basso, thank you for taking this journey with
me on this episode of I Took aHike Appreciate you having me
down, it was a great afternoon.
Another audible high five comeon.

Speaker 2 (55:34):
Good one.

Speaker 1 (55:35):
Next time on, I Took a Hike.
We finally put the Netflixdebate to bed.
When we journey alongside thelast CEO blockbuster, jim Keys.