Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
All right, welcome to
another Small Business Pivots.
Today we have a special guestfrom around the world and, as I
say week to week, only thebusiness owner can say their
name and their business, likethe business owner.
So introduce yourself whereyou're from and your business.
Speaker 2 (00:15):
We're an advisory and
venture capital firm for tech
companies and we areheadquartered in the Granite
State, which is New Hampshire.
Speaker 1 (00:30):
We're about an hour
north of the city of Austin
Fantastic, so you're just alittle ways from our
headquarters in Oklahoma City,but you said you'd been here and
you've got some stories on theIE and all kinds of things.
So, listeners, you might wantto buckle up as we introduce the
show and we will be right back.
Listeners, you might want tobuckle up as we introduce the
show and we will be right back.
Welcome to Small BusinessPivots, a podcast produced for
(00:51):
small business owners.
I'm your host, michael Morrison, founder and CEO of BOSS, where
we make business ownershipsimplified for success.
Our business is helping yoursgrow.
Boss offers business loans withbusiness coaching support.
Apply in minutes and getapproved and funded in as little
as 24 to 48 hours atbusinessownershipsimplifiedcom.
(01:16):
All right, welcome back toSmall Business Pivots.
How do you think we're going tohelp our listeners today?
Speaker 2 (01:25):
Yeah, I think it's an
exciting time for small
business.
You know, I think there'sincredible momentum in the kind
of business climate, especiallyin America here with the latest
election results andinauguration, there seems to be
a lot of excitement for both themain street entrepreneur and
the world I work in is moretechnology startups, uh, and you
(01:48):
know where I think we're allhoping for more funding and you
know, lower interest rates anduh, just continue to continue
consumer spending, uh, and thatbenefits all of us.
So, you know, excited to talktoday about, uh, yeah, the life
of an entrepreneur and howthere's no straight line, right,
michael?
to success in these businesses.
Speaker 1 (02:09):
Yeah, and just to
kind of give a timeline, I think
it's important because we didjust have the inauguration at
the time of this recording, twodays ago, and just yesterday our
new president announced a veryrobust AI tech.
So I think this is going to beinteresting to see what we talk
(02:31):
about today and, just in amatter of a year, how things are
different.
So let's go ahead and getstarted first with.
I know for a lot of businessowners, they relate to people
that they can kind of connectwith.
So what was your upbringing?
I know a lot of people have adifferent upbringing, but that
way we kind of get a place andsense of where you are today.
Speaker 2 (02:52):
Yeah, I think it's
going to be quite relevant for
the audience.
I grew up here in New Hampshire, small town, new Hampshire.
I think the population of thestate is just north of a million
, the whole state.
I think the population of thestate is just north of a million
, the whole state and the cityand town I grew up in.
You know 150 or so thousandpeople combined, so you could
kind of get a little perspectiveHour north of Boston.
(03:14):
I grew up in a small business.
My parents were entrepreneurs,my grandparents were
entrepreneurs, generation one ofthat small business was it
actually an athletic footwearmanufacturing business?
Um, that made athletic footwearuh, long before the days at
nike and, you know, reebok andunder armor?
Speaker 1 (03:34):
um, business started
in 1940s I didn't think there
was anything other than nike andreebok and I know isn't it
weird to think I actually askedthat all the time?
Speaker 2 (03:43):
I'm like was it like
a big brand and it's like you
know it.
Isn't it weird to think Iactually ask that all the time?
I'm like was it like a bigbrand?
And it's like you know, itwasn't like your shoes were
branded, you know.
Back then it was like that'swhat Nike innovated and it's
like oh, um, and the name ofthat um was actually called
Indian head shoe manufacturingcompany and um, many, many
listeners might've even hadbecause they have like ice
skates and um.
Still on ebay today I can findold shoes and football cleats
(04:05):
and soccer cleats it's amazingshoes it's really cool.
Um, yeah, and that business ranfor about uh through into the
70s and my father actuallymarried in and he was a shoe
salesman and ended up buildingthe outlet store for the
manufacturer.
And then when the, themanufacturing business shut down
at retirement age, at Gen one,my dad turned that for the next
(04:28):
45 years into a main streetsporting good retail and team
outfitter.
So they did like uniforms,equipment for the high schools,
little leagues, pop Warner teams, colleges locally, and that's
where myself and my fourbrothers I'm one of five uh sons
(04:49):
to my parents, don and gail I'mthe middle, which is so obvious
at the end of this podcast, butI'm the middle um, I'm in your
camp.
I'm the middle child middlechild or podcast hosted guests.
It sounds like, uh, but youknow, I grew up, you know, in
the, in the, you know mainstreet.
You know small business.
You know and this is days again, before big box stores there
(05:13):
was no dicks or models, or youknow or internet.
You know where you buy a gloveon Amazon.
You went into the local mom andpop shop and got fitted for
your shoes and your glove andyour and your equipment for
sport, and so that's where weall learn business and I always
say, growing up in a smallbusiness, you learn business
fundamentals really, really well.
(05:35):
And it's funny to be in techwhere so much funding goes into
it and companies lose money tobuild big businesses.
It's so backwards from ifyou're a Main Street
entrepreneur, you need to makemore money than you spend and
you need to make a profit to goon vacation.
It's just a different vibe.
But what my parents did reallywell and I carry this forward to
(05:59):
my career is they reallyvertically integrated their
businesses.
They bought the real estate,they had the retail store, but
then they had the team sales andthen they ended up launching a
screen printing and embroiderybusiness that would do the
uniforms and the hats and thenthey ended up building an arena
(06:20):
not as big as your Oklahoma CityThunder project, but there's an
arena here for 10,000 peoplethat they built across the
streets and then they didparking.
And that's the life of anentrepreneur, right?
It's like to capitalize on yourbrand, your community, your
footprint, and my parents taughtus that really well along the
(06:40):
way in our lives, really wellalong the way in our lives.
Speaker 1 (06:42):
What would you say
for those parents that are
entrepreneurs?
What would you say was probablythe biggest thing you learned
from your parents being anentrepreneur?
Just so they have?
Speaker 2 (06:55):
something to hand
down to their kids.
Yeah, I mean, one of the thingsabout entrepreneurship that I
fell in love with is, like it'sthe kind of like stick it to the
man, like the not working foranyone else.
You know mindset, you know likeI ended up.
I'll tell this more in a fewminutes but I ended up building
a tech business that we sold toOracle, and independently
(07:16):
building the tech business wasvery different than working
after the acquisition for Oracle, which was at the time a couple
hundred thousand employees, um,and so it was kind of that
independent spirit and sort oflike control of your own destiny
.
Um, and like that to me waslike, even if it was hard, right
, and even my dad always had toanswer calls on weekends and
(07:36):
nights and go in if the burglaralarm went off or there was a
leak in the roof or whatever,like it was that kind of
ultimate accountability.
Speaker 1 (07:45):
Um, in that
independence, that like really
stuck with me and led to myentrepreneurial career in
technology that's interestingbecause my kids one is in his
mid-20s fixing to be, and that'swhat he strives to do is the
freedom of not having to answeryeah.
Speaker 2 (08:06):
I think it's and the
thing I would say to any young
you know, getting into theircareer is also like you got to
find the hooks in your work withthe passion, because like it's
one thing to have the freedom,but imagine you have the freedom
.
It's something you don't evenlike to do, like you really need
to, like want to get up everyday.
Like I can remember my dad.
He'd make it home for dinnerevery single night and all of
(08:31):
our sports.
He never missed them, but hedid go into the office every day
at like 6am, you know, and youknow he was gone right, he was
out really early in the morningbecause he he had to make those
trade-offs and sacrifice.
Well, if he didn't like love thebusiness and love working in
sports and selling coaches andathletic directors and he grew
up as an athlete and he's in theHall of Fame of the city of
Manchester and he loves thatenvironment, then yeah, it would
(08:54):
have stunk if he was doingsomething he didn't love, even
if he had the freedom.
So it's probably balancingthose two things.
And too often people wake up 20years into their career and
they're like even you know, andthey're saying I don't like what
I do Like it sucks, like I youknow, and then you're making
like a career pivot but it'slike, oh man, you're going to
throw out two decades ofexperience Like that's kind of
that's there's no, no, no line,perfect.
Speaker 1 (09:16):
But you know you want
to, at least try to to make, so
it's not like you reallylearned anything along the way.
Speaker 2 (09:24):
So that's, that's a
good point of the pivots.
Like you know, there's pivotsthat are like just iterative
evolutions versus there's like acomplete 180 shift.
And I, you know, I always tryto tell people, like, as you're
evolving, like, think of it asiterative steps, don't think of
it as like something brand new.
Um, you know, so all thosethings Michael led me to, led me
(09:47):
to, um, you know, uh, my mycollege.
I went to undergrad businessschool, I, I played actually
college football division twoand I, um, really early on, when
I got there, I realized Iwasn't going to the NFL.
You know, it just took took abit for that to register.
Um, and so, right in school, Istarted to get internships.
I got very lucky to getinternships for very small
(10:09):
technology companies.
This was early 2000s.
Some really great founders sawmy energy and interest and
ambition and work ethic.
One of those first internshipsled to a seven-year run where I
stayed through college all theway to a few years out of school
, actually moved me toCalifornia and it was a software
(10:31):
business in the education space.
They sold software to prepschools, the K-12, private
schools, boarding schools andeven moved me to California.
That's actually what brought meto Oklahoma City several times
and I just fell in love as Iclimbed the ladder and kind of
sales and marketing functions,which is my background.
I just fell in love with, youknow, evangelizing, doing deals
(10:54):
with solving customer problemsand, you know, making a debt
right and whatever industry orsector I was going to go into,
and so you know it's been aninteresting.
That was all very foundationalstuff for me.
Speaker 1 (11:07):
Quick question and
that is you know, we all think
of Silicon Valley kind of as thehub of tech and of course,
where I'm at we have hub isreally up and coming.
It's probably one of the topthree industries now in our city
, austin is.
Texas is getting real bigFlorida.
There's some other states.
Do you still think I mean, thisis your opinion only Do you
(11:30):
think, having been there, do youthink that's an advantage?
Do you think you really learneda lot more?
Or do you think it's reallyexpanding across the country?
Because I know that we have alot of listeners in the tech
space and they're probablywondering the same thing of are
we really as good as thosecompanies or that talent out
there?
Speaker 2 (11:47):
Well, I mean, I'm
wildly biased here, and I
believe you can build a greatcompany anywhere, even in
technology, and I believe,especially in this day and age,
with remote work and offshoredevelopment and Zoom that we're
on now, I think it's all just aheck of a lot easier than it was
20 years ago to build a goodcompany anywhere.
(12:08):
But I'll tell you what.
I lived out in California, andI moved home to become a chief
revenue officer of a very earlystage technology and
infrastructure company, and itwas back in my hometown, and
many people said I was an idiotto move back from California to
New Hampshire to expand upon mytechnology career, and we took
that company from 15 people to500 and up to 100 million in
(12:31):
revenue, and we sold thatcompany to Oracle, and then
Larry Ellison, who justannounced the AI initiative
yesterday, with OpenAI andSoftBank that you were referring
to in the beginning of theprogram.
So I think now, in the year2025, you could build a tech
company anywhere.
There is a concentration ofcompanies and there is a
(12:52):
concentration of talent inSilicon Valley, though, and in
New York City and in other majortech markets, and there's good
and bad to that.
Right, there's good in that big, big companies can find the
talent they need.
There's bad in that smallcompanies have to overpay for
talent if they are in thoseareas right.
So it's why you're actuallyeven seeing a lot of companies
(13:13):
create different hubs andoffices and remote setups and
all that around the country.
But you know, I obviously amwildly biased, having built a
successful tech career and nowmy advisory at Venture Capital
Firm in Manchester, newHampshire.
It's not like the hotbed of VCor the hotbed of tech, but we
advise and invest in startupsall over the world, including in
(13:34):
Silicon Valley.
So I think people should liveand work where they want to live
and work.
I think they should if that'sbecause they yearn for their own
community or to be close tofamily, or they like the culture
in one area or the other, theweather, you name it.
People should have that choiceand they should be able to build
good and successful careers indoing that.
Speaker 1 (13:56):
Appreciate you
sharing, because I just know of
someone last year that moved toCalifornia because they thought
there was probably moreopportunities, more skill sets
that they could learn andeverything.
So that's and plus theentrepreneurs.
Speaker 2 (14:08):
Yeah, and, by the way
, maybe there are, but there are
also way more competition.
So good luck with that right,exactly.
And the company I moved back toNew Hampshire for is a company
called Dine.
We specialize.
It was called the domain namesystem, but it was like
technical infrastructure behindyour websites.
It was called the domain namesystem, but it was like
technical infrastructure behindyour websites.
And our biggest clients in theworld were all based in Silicon
(14:29):
Valley the Twitters, theNetflixes, the Salesforce, the
Workdays right.
So I spent the majority of mycareer also in Silicon Valley
and you know, you come to findout that.
You know you both put yourpants on the same way, you put
your shoes on the same way andyou know even a lot of people in
Silicon Valley, by the way,went to schools in the East
(14:51):
coast.
You know, with the publicschool, private school, right.
So it's just, it's just, it'sjust, they just.
Silicon Valley has a headstartfrom the beginnings of like
Hewlett Packard and companies in1960s who just sort of like,
created these big trees thatdrop seedlings down over decades
.
I think a lot of otherecosystems are going to emerge
(15:13):
around that.
I think that's a good thing.
I also am of the belief thatevery company should be a tech
company or technology enabled insome way.
That's the world we live in.
Certainly that's how it'smoving with AI.
How does AI help augment yourorganization and your role and
make you more efficient and moreexceptional?
I think all these things makethe proximity just a bit
(15:37):
different.
Speaker 1 (15:40):
Great advice and
insights for all those
questioning their talent level.
Yourbusinessyorkie, you have avery interesting story on that,
so let's start there.
Speaker 2 (15:54):
Yeah, well, I gave
you a little bit, so you had
asked when we had met prior tothe recording.
The ie and IE stands forinvestment enterprise, but the
ie is intentional.
As I mentioned, my last companywe sold at, oracle, was a
domain name system provider, sowe helped do internet routing
for companies in four countries,and so one of our main clients
(16:19):
was actually the country ofIreland and the domain name
registry of IEDR, which is ie,and we spent a lot of time over
there.
Actually, back to the pointwe're making around Silicon
Valley, many Silicon Valleycompanies were actually hiring
their technical infrastructuretalent in Dublin, ireland, and
(16:41):
building pods in there as theirentry to Europe and EMEA.
I spent an incredible amount oftime because those were the
buyers of our services at Dimefor domain name management in
Dublin, and so I just grew anaffinity to it and originally I
actually launched Yorkie as mypersonal angel investing
(17:02):
advising website, my blog.
It was a personal thing while Iwas working my day job, and
when we went to launch the firm,we had this vision that
startups need a one-stopresource hub for services and
support and infrastructure andcapital, and that we thought we
could build that firm.
(17:23):
Think of us like a modernMcKinsey, a modern Bain.
That was our vision and as wesat around and talked about it,
we realized that there was greattraffic and great portfolio and
great content already at Yorkie.
And we decided and myco-founders, it wasn't my idea,
I swear to God they decided, hey, you know what, let's just run
(17:43):
with what you've already got andbuild a brand around it.
And we've been off and runningand this is about.
We've been at this for aboutfive years.
York IE's core operatingbusiness provides what we call
advisory as a service totechnology companies.
We have resources to supportyou across research and
(18:04):
development think softwaredevelopment, mobile app
development, more technicalservices.
We have go-to-market servicesto help you with messaging,
positioning, content, pr, thosetypes of things.
And then we also have GNAservices to help with financial
planning, financial modeling,bookkeeping, tax, those types of
things.
And we've technology-enabled,we're experts in all the
(18:24):
technology stacks across R&D,go-to-market and G&A.
And we have a massive team inIndia.
So York IE is globally about200 people.
We have about 35 or so here inNew Hampshire in our
headquarters, but then we haveabout 170 in India where I'm
actually heading in the nextweek to visit.
So it's all full-time employeesglobally.
(18:46):
So it's all full-time employeesglobally.
It's all our own captive IP,proprietary data and tools and
our own teams that really becomean extension of the startups
and technology companies we workwith.
And then we also have aninvestment fund.
We're a venture capital firm.
We invest in early-stage B2Bsoftware businesses.
That's our thesis.
Saas is what it's called thesoftware-as-a-service
(19:07):
subscription business model.
That's where we focus, and wehave 60 portfolio companies and
we've deployed around $60million in these companies.
So we have a really biginvestment base and a really
awesome and exciting group ofcompanies that we support.
Speaker 1 (19:23):
What triggered you to
take?
You're listening to SmallBusiness Pivots.
This podcast is produced by mycompany, boss.
Our business is helping yoursgrow.
Boss offers business loans withbusiness coaching support.
Apply in minutes and getapproved and funded in as little
as 24 to 48 hours atbusinessownershipsimplifiedcom.
(19:46):
If you're enjoying this podcast, don't forget to hit the
subscribe button and share it aswell.
Now let's get back to ourspecial guest what triggered you
to take the leap of faith intoentrepreneurship?
I know you were raised in theentrepreneurial world, but for a
lot of listeners they're like Igot this great idea of
(20:07):
listeners.
Speaker 2 (20:08):
They're like I got
this great idea but I like my
paycheck.
Yeah, you know, with me it waskind of DNA and you know it was
pretty organic.
You know I was really youngwhen I joined startups Right,
and you know as much as I tooksome risks to join them.
I was at an age where, you know, I didn't have a family yet, I
didn't have a mortgage.
I had fluidity and flexibilityin my life.
(20:29):
I could take some risks.
I could not just chase thepaycheck but also chase the
experience and the opportunityand see where it went.
I was fortunate to join greatcompanies with great
entrepreneurs and founders.
In my company, dine that wescaled and sold to Oracle, I was
just really fortunate that itwas a complementary parts fit.
(20:49):
The founders were engineers,they were very technical.
They didn't have a sales andmarketing business growth guy.
I was able to come in and buildall those teams and systems and
processes and organizations andbe entrepreneurial in a very
entrepreneurial environment.
That led me to launch a bunchof other companies investments
(21:11):
companies and real estatecompanies and other things.
We even launched a shoe brandcalled York athletics to to
honor the family.
And so we have all thesedifferent businesses and then
really it was kind of after myexit, which was a life-changing
financial event for myself andfuture generations, that I sit
there and really reflect on like, yeah, I'm in my mid thirties
(21:31):
at the time, what am I going todo the next?
You know, I don't know nexthalf of my life, right?
And and I and I kind of lookedin the mirror and I was like you
know, if there is a way for meto build a startup of my own
that could help other startups,um, and invest in other startups
and be this community that cankind of, like you know, help
(21:52):
others achieve the mountaintop,whatever that might be right,
whether that's financialindependence, whether that's
some big exit someday to a bigtech business, it doesn't matter
, everything in between.
I just wanted to kind of go seewhat I could do and build that.
I also didn't like in my worldyou know a lot of people who are
successful exits just becomeventure capitalists and that
(22:13):
just seemed kind of boring to me.
You know I didn't want to justshow up at the board meetings
and, you know, govern businessesI do that too, don't get me
wrong.
But I wanted to still have abusiness of my own that I was
trying to grow and scale andhire teams and, you know, really
try to inspire.
So for me it was organic phasesand steps and you know,
obviously an exit or a financialevent makes it easier to take
(22:36):
risk, you know relatively.
But you know I'm going for itright.
I mean I kind of like there's agreat line in the movie
Rounders about like you can'tlose what you don't put in the
middle but can't win much either.
You know it's like a great mattdamon, uh, john malkovich movie
and yeah, that's some likelines like that.
I always kind of whispered my inmy ears, you know, and I'm like
(22:58):
, all right, let's keep, let'skeep at it right what advice
would you offer tech peopletrying to build something?
Speaker 1 (23:08):
Because I'm sure
there's more than a dozen or so
people trying to come up withthe next big software, probably
like a million billion peoplelike everybody's got a great
idea.
So what would you say?
Is that you've learned being inthat space?
What, what, some insights youcould offer.
Speaker 2 (23:26):
Yeah, I mean, it
really just comes down to the
exit, the business building,execution.
You know, I think everybody'sgot an idea.
Like you said, I got 50 ideasin my brain but if you can't go
all in and you know, buildorganizations and teams around
you to go execute on those ideas, it's just an idea Right.
And you know, when we meet astartup who has a good idea, we
(23:47):
call it the market-in approachto company building, and what I
find a lot of times is ideasthat come from especially
engineering technology.
Founders tend to be like I knowI can build it.
Ideas, not the market needsthis.
And here's how I competitivelydifferentiate this idea from
anyone else who might try tobuild it.
So that's like the market-inapproach.
(24:07):
It's like studying your market,looking at competitors, looking
at comparators, looking at thelegacy players, looking at the
innovators, understanding howyou can carve your unique path,
your wedge, into the market thatyou can then scale upon.
So that's the challenge In tech.
It's like no one builds it.
No one attempts to build asmall tech company.
(24:28):
You're not trying to build atech company.
That's like a small business.
The reason people build techcompanies is to build something
big, and I think that's like a.
Really you don't really knowwhat you're signing up for when
you get into that.
Same thing with raising venturecapital.
If you're going to raiseoutside money, even if it's
angel money or bank debt money,you just need to know what
you're signing up for.
And when you raise venturecapital, you're actually selling
(24:51):
a little bit of your company toa partner.
They own a piece of it, so youreally need to know what you're
getting into when you'rebuilding it.
I wish I had a magic formula.
We make a lot of investments,we advise a lot of startups.
Sometimes the ones I think aregoing to be the biggest end up
flopping, Sometimes the ones Iquestion become the biggest
right.
All you can kind of do in theworld I play in is try to help
(25:14):
steward as many along aspossible.
Clearly, when you're anentrepreneur doing your own
thing, though, you're making abet on one, and what I remind
people many times is when youstart a startup or you join a
startup, you're betting onyourself just as much as you are
the startup, and you knowthat's a test of resolve, of
persistence, of salesmanship, offollow through.
(25:36):
There's a lot that kind of goesinto it that you know it's not
easy, it's not for the faint ofheart.
Speaker 1 (25:43):
Yeah, no, it's not.
Well, I have some question.
For probably more of yourservice-based businesses, this
is applicable because in yourworld, technology changes on a
dime, and so, for instance, therecent guest we just had now,
this was a long time ago, butthey had this bright idea in the
90s.
(26:03):
They built the software.
They got a humongous clientthinking they were set for life,
and then the internet camearound, you know.
So their software wasirrelevant now, and so in the
tech world that you're in, thatprobably happens every day.
So how?
But in the kind of theservice-based world we have a
little bit more notice, if youwill.
Speaker 2 (26:25):
So how do?
Speaker 1 (26:26):
you?
How do you move quickly to knowwhere those pivots are?
Speaker 2 (26:32):
It's a great point.
I think what's interesting forus is on the investments
business, we only do tech andsoftware and SaaS.
On our advisory business, wesort of work with any company
who wants to grow or who wantsto be more technology-led or
implement technology.
It doesn't mean they need tobecome a technology company, but
even services businesses aretrying to figure out how to
(26:52):
better leverage tech to dobetter service delivery or make
themselves more scalable orreach a larger audience.
So I think you're right about alittle bit more lead time, but
at the end of the day, if you'reupscale, it's harder to pivot
or iterate.
If you're smaller, it should beeasier to pivot or iterate, and
that's kind of the dichotomy.
(27:14):
I see is like you know, when Iworked at an Oracle, it was very
slow moving right, even thoughit had all the resources in the
world.
Getting anything done orreinventing yourself was near,
damn near, impossible, right?
When you're a small company andyou're a small team, um, your
ability to sort of adapt or dieis is right, staring you in the
face every day, right?
(27:35):
So I think it's just likerealizing that the nature of the
smaller business that we mayall operate in is is not precise
and and you can't be so um, sopig-headed to believe that the
idea you had at Formation is thesame thing you're executing on
in five years or ten years orthree years.
(27:56):
I just think in tech thatiterateness is almost a little
bit more like week-to-week orday-to-day or month-to-month or
whatever.
We're in more service-orientedor other more established
industries it might be like,yeah, six months or a year to
adapt, or three years to adapt,or you know um, but, but, but
(28:16):
again, there's also like likebig adaption, you know of like,
of like existential issue, andthen there's a lot of micro.
I always say it's like itstarts like a lot of death by a
thousand paper cuts, right, it'slike it's like even if, even if
something great happens, youknow there's always a lot of bad
stuff going on beneath thesurface.
You know so um it it again,it's just more of the the.
(28:39):
Where I see people fail inentrepreneurship is when they
don't go in with that asbaseline, right, when they when
naively or ignorantly, or maybethey had a great career in
corporate world and they want togo off on their own and be a
consultant or start a localbusiness.
And it's not all sunshine andrainbows everywhere.
(29:00):
A lot of times, when someoneworks in a big corporate, they
have no clue what's going on inHR and accounting or in legal
these are things that aredisjointed and not connected to
them.
Or in a small business,everything's your problem,
especially as a CEO, as you know.
That's the type of stuff I liketo think about.
I do think entrepreneurship isa DNA thing too.
(29:24):
I'm not saying you can't teachit or you can't learn and become
better at it, but you, youreally got a deep down in your
core.
You know the amount of peopleI've seen go really early into
startups or start their ownstartups or join a small
business or quit their job towatch a brewery and then hate it
.
Um, you know, in the end it'skind of like if you look at
their like personality, dynamicand their you know resolve and,
(29:47):
like some of these like you heargrit, grit.
Some of these things you thinkabout when you think about an
entrepreneur, regardless of type, some people just don't have it
.
Sometimes you need to go do itto figure out if you have it or
not.
Other times, you and I, michael, can look at them and go, eh,
it's going to be tough.
I worked with a lot of people atOracle, for example, when I got
(30:08):
acquired there, who were likeenamored by you know young
entrepreneurial guy.
I ended up being the GM of ourbusiness unit at Oracle.
Our group grew to 8,000 people,you know, and a lot of these
people who worked there 35 yearswould come talk to me and we'd
trade notes on career and Iwould like walk out of those
meetings.
I'm like like how could youstay here this long?
We used to call them corporatesurvivors.
(30:29):
It was almost like a reality TVshow or something.
It's like wait a second, you'vehad 17 jobs in 30 years, all in
different divisions anddepartments and levels and comp
and all this stuff.
It's just all about protectingyour compensation, protecting
your stock you were given orearning.
(30:50):
This is a different ballgame instartups, right?
Speaker 1 (30:53):
Yeah Well, you make a
great point, because I know a
lot of small business owners orstartups.
They think if I just get thisbusiness to this level, my life
will be set.
And one of our past guests onthe podcast he said let me tell
you the difference, cause he'sgot a, you know, $500 million
(31:14):
company.
He said let me tell you thedifference between when I
started and now.
He said when I started it waslike writing a sea dew and you
can zip and zag and you're notgoing to do much harm.
You might tip over, crash inthe water.
You try to make those turns ona yacht.
you've got casualties, you'vegot major damage and A you can't
(31:35):
even do that.
Like you were saying, an oracleis like moving like a.
Speaker 2 (31:39):
An oracle, I would
equate to like a, like an ocean
liner with that, you know, right, like yeah, that doesn't turn
at all.
It doesn't turn at all, like youknow, and and sure, like on the
ocean liner and the crate inthe back, like maybe there's
some movement.
But, like you know, it's toughto turn the whole thing Right
(31:59):
and that's going to take adecade or two, two decades,
right, the Oracle cloud has beena two decade thing and it's
starting to pay off right Bigtime.
But you know it's a verydifferent environment and I
think that's really importantfor people to just recognize as
they're thinking about careerpaths.
Speaker 1 (32:15):
Absolutely, because I
always say we don't know what
we don't know as entrepreneurs,and until you've been there, you
don't know.
So I'm just sharing that.
Speaker 2 (32:32):
For those that think
there is no magical level that
you're going to get to, that allyour problems go away and your
life is set, unless you sell itfor a billion dollars.
And then yeah, but I would tellyou, even like having lived in
a small family business, havingworked in small startups, having
worked in mid-sized startups,having worked in large startups,
having sold my company to oneof the top 50 corporations on
the planet with the top fiverichest guy at the helm, there's
problems at all of them.
They're all actually hard.
Every one of them is very hard.
(32:54):
It's just a different level ofhard and there's a different
level of context and there's adifferent level of perspective
you need to have at each of them.
Then sitting on this side ofthe table is both now an outside
advisor, consultant and boardmember of many startups.
There's different contexts,there's different stages,
there's different perspectivesand they're all hard.
I think what happens too oftenis people just pattern, map the
(33:18):
different stages or they try torun the same playbooks or
templates or give the sameadvice.
One thing that's hard about apodcast interview when you get
asked about advice, you have tobe pretty generic.
They don't know the situationor context of the listener.
If I was sitting one-on-one,I'd be like tell me more, learn,
learn, learn.
If I were you, I would thinkabout the next phase of your
(33:41):
evolution and growth.
I'm sure you deal with this allthe time.
It's not like you can just givethe same advice to the same
five companies, and also youalso don't even know the
philosophies or ambitions oraspirations of the people
running them right.
So it's a unique challenge, Ithink, in our world to coach and
guide when everybody's verydifferent.
Speaker 1 (34:05):
What is a pivot that
you would not do, or do again,
or wish you would have donealong the way?
Speaker 2 (34:13):
Jeez, I don't know.
I mean, I think, in scalingdine, you know that was a really
interesting time.
Um, we, you know, we, we endedup raising a bunch of money by
the end of that company forprivate equity and growth equity
.
And you know, I think there waslike a window of time where,
like you know, we, we, if weplayed our cards right, it made
some interesting productdevelopment decisions, some
(34:34):
different M and a decisionscould have been an independent
company that went public on itsown.
And then, you know, again, it'sisn't this funny perspective.
I'm giving like we sold for$600 million and I'm acting like
could have, could have beenbetter.
But literally there was a fewyears in there where I was like
man, if we made this productdecision or we bought this
company, or we have evolved fromdeep domain infrastructure to
(34:56):
cybersecurity, our path aheadcould have been very different.
But then again, I look back atthe context.
These are easy things withhindsight.
We were all really young.
It was like a wild ride.
It was high stress, high, highanxiety.
Like you know, I could barelybreathe on the end of that
journey, you know, just wantingso bad to see it culminate in a
life-changing event, which itdid, um.
(35:18):
But you look back sometimes andyou're like I played this a
little different, play this alittle different.
It could have been different,um, but that's a.
That's a good problem to have.
That's a big pivot, pivot,that's a first world problem,
all those terminologies.
But again, I've seen it allalong the day.
I could have given my dad advicethat he should have gone more
digital, he should havefranchised, he should have built
the website.
He could have been the next Dix.
(35:39):
But then he talked to my dadand he's like I wasn't going to
mess with a good thing.
He's like I was incrediblysuccessful.
I was able to be a smallbusiness owner.
I supported five sons.
I sent you all through college.
I used to always ask him whydidn't you want any of us to go
to school and come back and workhere and help you build this
and scale this thing and bringin technology and all that he's
(36:00):
like?
Well, first of all number one,I didn't work my ass off to send
you everywhere to come back anddo this here.
Number two, I didn't work myass off to send you everywhere
to come back and do this here.
Number two I'm not taking a paycut to hire you.
So you know that's the way it is, and I used to, over the years,
always try to bring softwareinto the for inventory
management or for, you know,credit card processing or right,
and he'd be like, get out ofhere, I have my way of doing it,
(36:21):
I have my systems, like.
So again, that's what I meanabout the context, right, like
he could have tried to go bigwith it and it could have
imploded and ruined a good thing, right?
So I think all these things arevery relative.
Someone said to me when I wasvery young that success is
relative, and I think that's areally, really important lens
for everyone listening to thinkabout, like, what's relative
(36:42):
success to you and what are youplaying for?
And that's going to bedifferent for everybody.
Speaker 1 (36:48):
So your company York,
who is this for?
In other words, like sizeindustry.
I know you said tech, but yeahon the advisory services
business.
Speaker 2 (36:58):
It's really any
company who's looking to take
the next level, to grow, who'slooking to technology enable
their business.
So they want to build an app,internally or externally,
whether they need help withmarketing or finance or R and D.
We have service capability forall that.
You know, our biggest companyclients probably doing a couple
hundred million in revenueSmallest is a brand new idea.
Who wants to build the nextgreat app?
(37:19):
Right?
So it really does fiteverywhere in between.
But it's definitely like a moreof a tech centric, growth
centric, centric, ideal customer.
We actually partner with a lotof other venture capital firms,
private equity firms, banks, lawfirms who have portfolios of
companies who could use help inoperating their business, and
that's where we come in andsupport them.
(37:40):
And then anyone listening who'sbuilding a SaaS business, a B2B
software business that's wherewe are a seed stage, pre-seed
stage investor, so we're a trueinvestor.
It's usually companies havefound some initial traction or
looking for a little bit ofearly growth capital to take it
to the next level, but they wantthat capital amount just to be
dumb money.
With all respect, they want toactually help and resources and
(38:04):
people have been there done thatto support them, and that's
what our 200 plus personinfrastructure can help provide.
Speaker 1 (38:10):
I know we've just
barely touched the surface of
what you do and your experience.
How can people follow youdirectly or get in touch with
you to learn more?
Speaker 2 (38:22):
Yeah, that's great.
I'm across all social channelsat K York 20.
That's my old football number.
I've had that since AOL,instant messenger and like 93.
So you can find us everywherewe're very accessible.
I'm all over LinkedIn.
(38:48):
You know you might have to muteme, you know, because I'm
always putting out, you know,opining on the state of affairs
in our world, right, so but Ireally appreciate you having me,
Michael, it's been fun.
Speaker 1 (38:59):
My pleasure.
Well, I will say thank you forthe throwback, because I'm not
kidding you and you may havedone this to some other people I
forgot when I was a kid that wehad to go to a local store to
get the numbers ironed on ourjerseys, get our shoes fitted.
I forgot all about that becauseI've been so used to Amazon and
(39:19):
Dick's and Academy and allthese other stores, but it got
so busy at that one store.
You had to make an appointment,your team had to have an
appointment, you had to go inbetween 2 and 4 on a Tuesday or
something or you weren't gettingyour jersey in time.
I forgot all about that.
Speaker 2 (39:35):
Imagine the visceral
reaction I have now when I have
to go buy one of my three kids'sporting equipment.
I just had to get lacrosse gear.
My middle child wants to playlacrosse this year and so I had
to buy him all this gear.
And you know, it kills me thatI can't just go to Indian Head,
my dad's old store, and do itwith that personal touch, where
(39:56):
they actually know what they'retalking about.
They could fit you up and sizeyou up and make sure you buy the
right equipment for yourperformance level.
And you know I have to go kindof like through the commodity
factory of Dick's to pick it allup.
Speaker 1 (40:08):
Right it's just it is
.
It's a different world, butyou're right.
Speaker 2 (40:15):
A lot of a lot of
these things are a kind of
flashback and it's actually wedo a lot of work in other like
vertical industries that arelike building software for a
specific vertical, and so we geta lot of this throwback to like
, oh, that's how it's done, penand paper, or like in person,
like no digital experience, youknow, like so we, we we get this
a lot in my world.
Speaker 1 (40:33):
I bet.
Well, I always end with aquestion, and that is if you're
in a room full of businessowners all sizes, different
industries what's a somethingyou could offer to all of them
that's applicable?
So it could be a quote, a book,some insight, something you
learned along the way.
Speaker 2 (40:50):
Yeah.
So one thing I always talkabout is in college I actually
had in one of my classes youcould get a guaranteed A if you
brought in a notable guestspeaker to class.
So you get three big projectsfor the semester and you get one
A if you bring in a guestspeaker.
So I brought in the founder andCEO of Total Gym.
(41:11):
Remember that, with ChristieBrinkley and Chuck Norris, it
was like the infomercial.
He was a college teammate ofmine's father and he came in and
he told this amazing storyabout what made him successful
and it was all around honesty,passion and persistence.
And I remember just back thenthinking to myself like he just
had this great way of speakingbecause like he, he was almost
like like an accidental success.
(41:33):
He was like a bodybuilder whowanted to come out, who injured
himself in his back and hewanted to come up with a, a way
to um have like low resistance,um, working out.
That didn't wasn't like heavy,heavy, uh, you know dead weight,
you, you know working out.
And it always stuck with meAlways be honest, always be
persistent, always be passionate, you know, I think that's what
(41:56):
separates.
Speaker 1 (41:58):
Yeah, that's great
advice.
Well, you've been a wealth ofinformation and a blessing to
many.
I appreciate you, Kyle, forsharing with our audience today
and wish you continued success.
Speaker 2 (42:08):
You as well.
Thanks for having me.
Speaker 1 (42:10):
My pleasure.
Thank you for listening toSmall Business Pivots.
This podcast is created andproduced by my company, boss.
Our business is growing yours.
Boss, offers flexible businessloans with business coaching
support.
Business loans with businesscoaching support Apply in
minutes and get approved andfunded in as little as 24 to 48
(42:30):
hours atbusinessownershipsimplifiedcom.
If you're enjoying this podcast, don't forget to hit the
subscribe button and share it aswell.
If you need help growing yourbusiness, email me at michael at
michaeldmorrisoncom.
We'll see you next time onSmall Business Pivots.