June 21, 2025 • 37 mins
Cut The Tie Podcast
Episode 273
What happens after you’ve won the game—money, exits, prestige—and still feel like something’s missing? In this episode of Cut The Tie, Thomas Helfrich sits down with Gregory Shepard, a 12-time founder and serial entrepreneur, to talk about redefining success, embracing neurodiversity, and cutting ties with the systems that keep us playing small.
Gregory shares how growing up neurodivergent, surviving trauma, and building multiple businesses led him to question the traditional narrative of success. This conversation dives deep into the power of acceptance, the myth of the lone genius, and the frameworks Gregory uses to help founders thrive—with both business outcomes and personal peace.
About Gregory Shepard
Gregory is a 12-time startup founder, angel investor, and creator of Startup Science—a platform that helps early-stage companies avoid the common pitfalls that lead to failure. Diagnosed with autism and dyslexia, Gregory has turned his neurodivergence into a superpower, using structured thinking and systems design to help entrepreneurs achieve more with less chaos. His mission: to make entrepreneurship more accessible, inclusive, and effective.
In this episode, Thomas and Gregory Discuss:
- Redefining success beyond money and exits
Gregory opens up about how achieving traditional startup success left him feeling empty—and how he's learned to define winning on his own terms. - Living with neurodivergence as a strength
With autism and dyslexia, Gregory explains how structure, frameworks, and clarity became his tools for managing complexity and thriving in chaos. - The impact of childhood trauma on entrepreneurship
He discusses how unresolved trauma shaped his early drive and why healing that trauma helped him become a better founder and person. - Why most startups fail—and how to prevent it
Gregory breaks down his 4-stage model from Startup Science to help founders build smarter, validate ideas faster, and avoid avoidable failure.
Key Takeaways:
- Achievement doesn’t equal fulfillment
Success on paper means nothing if you're still fighting inner battles. True peace starts with knowing yourself. - Structure sets you free
For neurodiverse thinkers, systems and frameworks aren’t limiting—they’re the keys to creativity and control. - Your past isn’t your prison
Trauma may shape your story, but healing lets you rewrite it. Growth comes from facing, not ignoring, the hard stuff. - Startup failure is preventable
Most early-stage companies fail for avoidable reasons. With the right model, you can outlearn, outlast, and outbuild the odds. - Burnout is not a badge of honor
Rest, reflection, and alignment aren’t luxuries—they’re requirements for building something that truly matters.
Connect with Gregory Shepard:
🌐 Website: gregoryshepard.com
🌐 Startup Science: startupscience.io
💼 LinkedIn: Gregory Shepard
Connect with Thomas Helfrich:
🐦 Twitter: @thelfrich
📘 Facebook Group: Cut the Tie
💼 LinkedIn: Thomas He
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Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
Welcome to the Cut the Tie podcast.
Hi, I'm your host, ThomasHelfrich.
I'm on a mission to help youcut the tie to whatever it is
holding you back from success.
As I always say, you need todefine that success yourself,
otherwise you're chasing someoneelse's dream.
Today, I am joined by MrGregory Shepard.
Gregory, how are you?
Speaker 2 (00:18):
Thank you for having me.
I really appreciate it.
I'm honored to be on your show.
I appreciate it so much.
Speaker 1 (00:24):
Well, I appreciate you being here as well.
We were having a briefdiscussion about coffee Today.
I may mumble, I just feel likemine's broken.
So if you hear a mumble and youtruly don't have a clue what I
said, just answer whatever youwant.
Speaker 2 (00:38):
Just however you like .
Speaker 1 (00:39):
I believe cats could be blue if you mixed them right.
Okay, that's fair.
All right, Gregory, let's do it.
Introduce yourself and what itis you do.
Speaker 2 (00:48):
My name is Gregory Shepard.
I have two websitesGregoryShepardcom and
StartupScienceio.
I am a 12-time entrepreneur 12startups, 12 exits, four private
equity awards for transactionsbetween $250 million and a
billion.
I'm the author of the StartupLife Cycle, a book based off of
(01:08):
five years of research onfounder failure and success.
I do a lot of speaking, tedTalk, I'm a Fulbright scholar
basically a lot of differentthings.
Sorry, I hate talking aboutmyself.
I feel like I have to do it allday.
Speaker 1 (01:25):
You know what?
It's only going to get worsebecause we're going to we're
going to peel some onions of you.
It's going to be great.
Okay, you're ready for thepauses of uncomfortable people?
Here we go, hey.
So before we dive in a littlebit to what you're doing, give
some the one link.
How many people, like, go intolike a two-minute rant?
(01:51):
I'm like and that link wasGregoryShepardcom Go stalk him
while he's speaking Okay, 12exits, that's a lot, and there's
a lot of books on these topics.
So I always kind of ask thislike unique identifier question.
But you know why?
Why you?
Why?
Why should they read your book?
Speaker 2 (02:15):
work with you.
I think I'm unique in that Icame from nothing and I've built
and sold 12.
So that's a really rare trackrecord, and the book is based
off of five years of research onfounder success and failure.
So I mean, I spent a half amillion dollars.
There was a couple hundredthousand case studies, thousands
of interviews.
It took five years with fivepeople to get the data.
Then I took all of that dataand found out that one of the
(02:40):
biggest problems based off ofall the research was that
founders didn't understand thelife cycle.
They thought that a round offunding was a phase, but that's
something that happens during aphase, but that's not the phase
itself.
So there's two things you needto know when you're starting
your company where you are andwhere you're going.
It's like a GPS.
So I wanted to do is to write abook that was the GPS, so they
(03:04):
understood where they're goingand what they're going to
experience along that path,hopefully preparing them and, by
doing that, offsetting thereasons why they fail.
Speaker 1 (03:17):
I love metaphors In that analogy, funding is no more
than a fuel stop you would justprepare where it is so you
don't run out of gas no morethan a fuel stop, you would just
prepare where it is.
Speaker 2 (03:25):
You don't run out of gas.
Yeah, that's part of thejourney, right, you have to.
Well, you have to if you'regoing on a road trip.
Right, you have to know whereyou're going to stop for fuel
and how long it's going to takefor you to get there, how much
it's going to cost.
When you're going to eat, whenyou're going to go to the
restroom, when you're going tostay the night time you're going
to start in the morning.
I mean, you have a whole planfor your journey, right?
Well, most entrepreneurs in myresearch didn't even know where
(03:50):
they were or where they weregoing, let alone planning a
journey.
So it's no wonder that a lot ofthem fail.
Right?
If you started a road trip andyou didn't have your destination
in the world of startups,that's your exit strategy.
If you don't have yourdestination when you world of
startups, that's your exitstrategy.
If you don't have yourdestination when you start, how
are you ever supposed to getthere?
You're going to run out ofmoney, time, energy during that
(04:15):
process before you even getthere.
Speaker 1 (04:19):
As a founder myself, that is very true, because
sometimes you're just so excitednot to be working for somebody.
Then you do raise a little bitof money and you realize I
probably raised oneone-hundredth of what I needed
to.
Yeah, You're like, ah, Becausecash flow, that's an important
piece If you really want rapidgrowth.
You're going to have toleverage, You're going to have
(04:41):
to get money in that's not yoursunless you're just
independently wealthy.
Yeah, you got to do somethingright.
You got to grow a cash registeror bring it in through.
You know there's some kind ofinvestment vehicle.
So, talking about your journeya little bit, though, but before
you do, I want you to definesuccess for yourself.
What is currently thatdefinition?
Speaker 2 (04:59):
Currently, my success is based off of helping
entrepreneurs succeed.
That is my life's mission now.
I mean, I've spent a lot oftime helping myself and now my
life is dedicated to helpingothers.
Speaker 1 (05:15):
I like that.
So you're measuring yoursuccess by the impact you're
having on others right now.
Speaker 2 (05:20):
Right.
Either social environmentalimpact innovation impact Right.
Either social environmentalimpact innovation impact right.
So if you look at the world,going back all the way to the
industrial revolution, even backto Henry Ford, et cetera
innovation is what drives ourplanet.
It drives everything, right,and that all comes from startups
(05:41):
.
Corporates don't innovate, theybuy innovation, right.
So, if you think about it, ifyou're helping founders this is
why this is my focus by helpingfounders, not only are you
helping those people that needfinancial equality why would
they be a founder if they werealready financially independent?
You're not seeing that, right.
You're seeing people who aretrying to make something happen
(06:03):
for themselves and their family.
So then you're helping withsocial equality, right.
Well, most of the technologythat you see now is technology
oriented towards changing things.
Right, it's either upgradingthe current technology, stacks
people using, etc.
But the big revolution istechnology impact into the
(06:26):
industrial revolution.
So they call it industrialinnovation or industrial
revolutionary technology, andthis is basically going back to
the industrial revolution andrebuilding everything that was
built before.
It's the biggest transformation.
Industrial transformation is thebiggest thing there is right
(06:46):
now.
Right.
So it happened with roboticsand now AI is stepping up on the
top side of it, and the two arecoming together to transform
things.
So this is like helping outwith the planet, right, because
part of the impact that we'remaking on the planet is making
it harder for us to live here,and that is reduced drastically
by industrial transformation viastartups, right?
(07:09):
So, from my perspective, if I'mhelping startups, I'm helping
out with the environment, I'mhelping out with social, I'm
helping out with innovation andI'm helping out with people,
right?
And so, to me, having my focusbe helping startups and those
that are helping startups isindirectly helping in all those
other capacities, and that's whyit's my life mission.
Speaker 1 (07:33):
I don't think the earth cares what we do to help
it, because it took a meteor andhere we are.
I mean it's like, yeah, I hitmy meteor.
Speaker 2 (07:41):
Yeah, it's not a matter of the earth is going to
be here, it's a matter of we'regoing to be here.
Speaker 1 (07:44):
Yeah, the earth doesn't care what we.
It will correct us, don't worry, we will.
If that was a human, the earthwas a human and eventually we
just get annoyed with the dirton its hands.
It's.
I'm just gonna shake a sleeve,hold my hair and get a haircut
and wash off and we'll see whathappens next.
Doesn't care I always.
Speaker 2 (08:03):
I always think of it like, like you know, when your
dog gets out of a out of waterand it shakes and it shakes off
the water, I always feel likethe earth is one day going to
get fed up with us and just belike all right, that's it, tired
of swimming.
Speaker 1 (08:15):
Yeah, you know, along your journey, tell me a little
bit about it and it and whatthat big, the biggest, maybe
metaphoric tie that you've had acut to find success today.
Speaker 2 (08:28):
I think that oftentimes people are like you
know what are the keys?
Like how can you just give methe hack right?
How do you do what you do?
You know how do I do all thesestartups and all these things
that I do?
How is that even possible foran individual to do?
And I say, first of all, thereare five things that you need to
(08:49):
be successful.
I call it a handful becausethere's five fingers in your
hand right Focus, drive,enthusiasm, discipline and
optimism.
I think if you have thosethings, then things like
organization, time managementthey fall under discipline,
right, and things likemotivation fall under drive and
enthusiasm is contagious and youcan't build anything without
(09:12):
having focus.
So I call it the handful ofthings you have.
So first thing I tell people isI'm like you need focus, drive,
enthusiasm, discipline andoptimism.
You need to like, get thosethings and attach to them and
make it part of your daily life.
And then the second thing is todig into those is time
management and organization.
I think time management andorganization are very linked
(09:35):
together.
If you're organized, you'reautomatically going to save time
.
Therefore, you have timemanagement.
The reason why they're separateis because time management
includes prioritization anddelegation right.
So I use tools like theEisenhower impact over effort
and urgent versus important formy priority metrics, and then I
(09:56):
use tools like the RACI, whichis responsible, accountable,
informed and consulted for mydelegation metrics.
And those are the things that Iuse and that's that's sort of
like real, real important keys,I think, for success.
So that's your hack.
Speaker 1 (10:14):
Like when you, when you, you know from the actual,
though, like kind of thing thatwas holding you back in life.
What's something that you'vehad to deal with to to overcome
yourself, Like this've had todeal with to to overcome
yourself.
Like this, I had to stop doingthis or I had to start doing
this, like everyone's got one.
What's your?
Speaker 2 (10:31):
yeah, I mean, I have autism and level five dyslexia,
so I read at like a fourth gradelevel, right and and like I
can't even read menus.
I have special tools to help meread menus.
Overcoming that before AI wasimmensely difficult.
It took me, you know, fiveminutes to write an email, even
(10:56):
a short email, because I have tohave the machine read it.
I have to dictate to themachine and then read to them
and then have it read it to meand then dictate and change it
and go back and forth, you know.
And now with AI, it's amazing.
But I think that's one of themajor things.
And the other thing had to dowith just and this is something
for all entrepreneurs isself-doubt and imposter syndrome
.
Right, like when you'rebuilding a business and
(11:19):
sometimes, if you're disrupting,you feel like you're standing
out there all by yourself.
Right, there's, there's nobodyelse out there but you and
you're, and you're like am I theonly one that sees this?
Apparently, I am.
Am I crazy?
Is this actually a goodbusiness?
What you know?
Why am I?
You know, I don't, nobody elseis out here, and it's you know.
You feel like you're standingin a desert and you're trying to
(11:40):
build a city and there's nomaterials, there's nothing.
So overcoming that self-doubtis a fundamental thing to
overcome, and it's not somethingyou overcome once.
It's something you overcome allday, every day oh yeah and I'm
just the oh good, no, no, you goahead.
No, no, no, you go ahead, okay.
(12:03):
And the other thing is thisimposter syndrome.
Like I mean, I speak at thesebig events in front of hundreds
of people, I've written books,I've been a chairman for
congressional candidates, I'vemet barack obama twice, I've
built all these businesses andsold them.
I've done all these thingsright and I still have imposter
syndrome.
Like I mean a hundred percent,like even on this podcast, I'm
(12:25):
like you know, am I worthinterviewing?
You know, like why?
Why do people want to even hearwhat I have to say?
So it is a really big deal andit happens to everybody.
It's not silo to you, listener.
A self-doubt and impostersyndrome happen to anybody that
is an entrepreneur.
And if it doesn't happen to you, then you're arrogant.
(12:46):
And if you're arrogant, youneed to step back and evaluate
you know, I was one of the samething.
Speaker 1 (12:52):
Am I going to really interview this guy?
And then now I've met you, I'mlike I'm surprised he's on this
podcast.
I'm so happy you flipped thescript on me.
Now I got the imposter syndrome.
How'd you do?
I don't even know what to donow at myself.
12 exits I can't.
I can't get, like you know, 12.
Um, just maybe a kind of asidebar.
(13:13):
Like you know lots of differenttypes of businesses.
Are you rinse and repeating thesame models?
Speaker 2 (13:19):
I mean, the startup life cycle is the method I use,
right, but the concept, the idea, is the art.
I always tell people this.
I'm like the idea is the art,but the execution of the
business itself is actually ascience.
And if you look up thedefinition of science, it
definitely explains the processof building the business after
(13:39):
you have the art, which is thevision in the first place.
Right, and there's two types offounders.
There's visionaries and subjectmatter experts.
And visionaries think from thetop down, from the outside in,
and subject matters expertsthink from the bottom up, inside
out.
Experts think from the bottomup, inside out, right?
(13:59):
So there's one of them islooking at something and saying,
oh, this is a disaster,somebody needs to do something
about it, and then they dosomething about it.
That's the subject matterexpert.
A visionary is looking at anentire system and they're saying
, oh, this whole thing is broken.
And then they work with subjectmatter experts.
So co-founders and foundersusually are good pairs, with one
being a visionary and one beinga subject matter expert.
(14:19):
So if you look at Steve Jobs,if you look at Bill Gates, they
all had subject matter expertsunderneath them and they were
the visionary.
And so you know, like Wozniakwas.
So I think that it's.
It's the the.
The fundamental thing for me islooking at problems as
(14:40):
opportunities, and I'll give youthe way I think about this.
Imagine a still pond.
The water is completely still,there's no water moving, and you
throw a rock at the center ofthat pond.
You get those rings that arecat happen.
So the rock would be adisruption.
So AI, the phone, the iPhone,the internet, robotics these
(15:02):
things are disruptions, right.
So the rock hits.
The first rings that appear arethe biggest opportunity, the
biggest rings, but there's notvery many of them because the
rings are really small at thatpoint.
But as that disruption is timedout, you know, over time you
start to see the ring spread outand those rings on the outer
(15:23):
side there's way moreopportunities.
They're not as big, but there'sway more opportunities.
I don't focus on the disruptionand I don't focus on the initial
rings.
I focus on what's on theoutside of that.
Why do I do that?
Well, there's this story ofLevi Strauss and everybody's
like oh, levi, levi, right, butnobody remembers the gold miners
(15:45):
.
What Levi did is he sold jeansto the gold miners, because the
gold miners needed pants to wearwhen they were gold mining.
Guess who was more successfulthe gold miners or the guy who's
selling the jeans right, or thepickaxe?
Either one Exactly, you get thepoint right.
So, basically, what I like todo is I consider the original
(16:08):
disruptors the people with thepickaxe and the gold pans, and
the need of jeans and et cetera,and the gold pans and the need
of jeans and et cetera and thenI look for things that I can
market to those people becausethey are the original
aggregators of the concepts, ofthe art, of the idea, right.
So that's sort of like my trick.
Speaker 1 (16:28):
I mean, there's no I'm glad to ask because we're a
marketing agency like my companythat focuses on primary
LinkedIn lead gen and, as I lookat it, we've pivoted more and
more to helping marketingagencies build a lead gen
company for themselves becausebecause that helps lots more
people, very focused, becausewe've done it.
(16:49):
So we're like why don't we justhelp other marketing agencies
do it right and for them?
Speaker 2 (16:54):
that's like a beautiful model, like if you the
train.
The trainer model is, I think,much better, because people want
that stuff in house.
It's too important, right?
So if you're teaching them howto do it in house, that is a way
better.
You're selling intellectualproperty as a much better
business model than sellingexecution.
Speaker 1 (17:13):
Well, and and so what we've found right and I think
this is really relevant and it'scalled instantly relevant
Didn't mean to put the pun inthere, but it's very relevant to
kind of, what I face, and I seelots of people face, is that we
have a couple of really niceclients that pay a good amount
of money for the really goodservices we do.
But we couldn't have gotten thatand we couldn't have trained
other marketing agencies unlesswe'd done it first.
(17:34):
And so we're about four yearsinto that journey and I'm like,
yeah, I don't, I'm 49.
I don't think I want to bedoing this 10 years from now.
I think I want to move thismodel to train the trainer.
But the next piece of that isbut who is it?
You know like, who do you nichedown to?
Because if you make it, evenfor coaches and marketing
agencies and consultants, you'renot selling anybody at that
(17:54):
point, right.
And so it's like you got tofigure out who can afford it,
who wants to do it, who wants topay for it, and and then you
know, show how to do it or whitelabel it with them or something
.
Speaker 2 (18:03):
so very important, and that's where I'm at right
now.
Speaker 1 (18:08):
Some of it's like who should I sell that training to?
Speaker 2 (18:11):
yeah, I mean, I'll tell you what I would do in your
situation.
Number Number one I would learnagentic AI, because agentic AI
can actually.
It's like having a team.
So what we did, as an example,is that there's a manager
believe it or not, there's an AImanager, a boss, and then the
AI boss has a bunch of employeesand each one of those AI
(18:34):
employees execute what the bosssets, but they delegate certain
pieces of it to a different AI,and so what you have is you have
a whole marketing team andthese little agents are telling
you know, one is telling thenext one what to do, which is
telling the next one what to doand how to do it.
Execute and bring it back tothe boss.
Right, this structure building,this is not something that you
(18:58):
can template.
You basically need to buildthis.
You can template the generalflow, but you got to go in and
modify it every single time.
If I was a marketing agentright now, I would be selling
not just the strategy ofmarketing itself, but I would be
selling, and not just theimplementation of the AI
(19:19):
marketing team, but the wholething.
Right, I would say we're goingto come in and, at the end of
the day.
The outcome is you're going tohave an automated, you know,
cold outreach LinkedIn campaignwhere it's generating unique
emails for every single prospect.
Blah, blah, blah, blah, blah.
Right, Like that's how I wouldbuild it.
And then I would sell theknowledge and I would also sell
(19:41):
the software execution, Becausewhere you're essentially selling
them is a full marketing teamguided by your expertise.
You know, that's what I need.
Speaker 1 (19:52):
It's actually very similar.
Just, I know we're kind of on atangent, but that is similar to
what we do, but it's actuallyvery similar.
Just, I know we're kind of on atangent, but that is similar to
what we do.
So we do show them amethodology, no matter what
technology exists, of process tofollow.
So you have a repetitive piecethat keeps the human in the
front and assisted by an AItechnology in the back, because
it's freaking amazing, that'samazing Because right now, ai to
AI agents aren't there.
(20:13):
Now, what I mean by that is, atsome point I'll have an AI agent
that filters all the things Imay or may not need and
occasionally I'll tell hey,listen, I kind of need help with
SEO.
It will go talk to other AIagents and say I think I found
two or three that may fit yourbill.
Do you want to meet with theowner?
That will happen and then allthe sales stuff will be done
through your AI's interactionsand stuff and the provability of
it and the verification, thepoint being within a journey.
(20:36):
I guess my point of this so I'mgoing to come back up is not
that.
You know, sometimes I get freecoaching on these things, guys.
It's just how it works.
Anyway, is that occasionally youhave to look at your own model,
because where you start, oftenfor a lot of founders in the
first, is they start with a jobthey've created for themselves
just so they can escape whateverthey came from to make money.
I did it.
Almost 95% of, not more ofentrepreneurs I met have created
(20:59):
a job for themselves.
What I think happens and whatyou're describing in the startup
cycle is um, the life cycle isto take that step, to be not
just in a job at a company youcan actually sell an asset and
to do that.
That's a process, that's afunction, that there's things
you need to do beyond the jobyou created for yourself.
Speaker 2 (21:16):
Yeah, fair enough, yeah, a hundred percent.
Like if you're, there'slifestyle businesses, which is
something where you're trying tosupport yourself, and growth
businesses, which are businessesthat you're trying to sell.
Right, and you usually raisemoney for growth businesses
because investors want theirmoney back, so you have to sell
it.
So what I specialize in are thegrowth businesses, and growth
(21:37):
businesses all have certainthings in common.
They all go through the samelife cycle and they all have the
same core drivers, so that'sgrowth margin and retention.
And growth margin and retentionare accountable by different
functional areas, and differentfunctional areas have different
key performance indicators.
And that is the same.
(21:58):
Whether you're building acompany that's selling agentic
software or you're building aCRM or whatever it is, it's
always the same and that's thepattern that's reoccurring.
And the reason why I've been sosuccessful is because I've
recognized this pattern,documented it and got really
good at following the pattern,and it works every single time.
If you just follow it, it worksevery single time.
(22:20):
The part it doesn't do is theidea.
Right, you have to have theidea, but outside of that, it
follows the system.
Same thing with what you do,right, somebody's like I want to
sell a widget and then you puttogether a process that sells
widgets the widget itself theyhave to bring to you, but the
system that you use is the sameregardless, right?
(22:41):
So that's what the book isabout.
That's basically.
Speaker 1 (22:46):
I'm definitely going to read it now that I have an
author that I can call and saywhat the hell did you mean by?
And I can throw this section.
Speaker 2 (22:52):
It's actually you know what I did.
I have an AI agent on mywebsite and it's trained on the
book and you can ask it anythingabout the book that you want
and it's just like talking to me.
It's amazing.
Speaker 1 (23:04):
You know it's funny with our own like kind of three
step or three kind of phase,nine step system that I have,
I'm like how could I get youknow AI, this, where this
becomes something that's uh, youinteract with an AI or some
form of an LLM, and so I'll takethat one offline with you what
your thoughts would be for that,because I think that becomes a
sellable asset that even you canembed strategy into the actual.
The IP could be in the strategythat sits behind the prompts,
(23:28):
right?
So you're going to give aninformation and the strategy
that you've given it is the IPthat you don't share.
So I'll take that one offlinewith you.
I want to move forward with you, though, so to learn more about
you.
This is awesome.
I'm so glad that I interviewedyou.
I was like man, am I sure aboutthis guy?
He may have imposter syndrome,and now we get free insult.
You know this is fantastic,thank you.
We're going to go longer, justbecause it's helpful to me and
(23:51):
it's my show.
Fuck, let's do it.
I can say one comment Dowhatever you want.
It's your show.
You can do whatever you want.
On your last day I found out aswell at work.
My kids said what if you didthis?
Like well, you could dowhatever you want on your last
day at work.
Guys, whatever you want.
Speaker 2 (24:05):
It's true.
It's true.
What are you most grateful for?
The same thing that I was, thatI absolutely hated about myself
or about, you know, the, the,the things I was born with, and
(24:28):
that is that, you know, myautism and my dyslexia have
really enabled me to see theworld and things completely
differently, and so, as a resultof that, it's it's it's just
drastically changed everything,right, like, I mean, it's just
like the way I see the world andthe and these things that I
think up and and all of thatstuff, it's all, it's all part
(24:52):
of the, the same, the way Ithink.
So, even though it's beenreally a struggle, like a
mountain of struggle, to getwhere I am, that struggle itself
has given me a lot of strength.
You know, if you think aboutstruggle overall, that's
evolution, right?
Plants that struggle survive.
(25:13):
Animals that struggle survive.
Over time they evolve.
So this has caused me to evolveinto a better person.
That's, you know, much betterat doing these things than I
would have been had it been easyfor me.
Speaker 1 (25:25):
So that's what I'm most grateful for was my
struggle it also gives youempathy that that would not be
there for others If you don'thave struggle.
It's hard to give empathy forsomething else, right, yeah,
you're kicking ass.
Hey, listen, there's a lot ofpeople who don't have dyslexia
(25:45):
that also read at a fourth gradelevel, just to be fair.
Speaker 2 (25:49):
That's true, there are a lot of I know, and I used
to think that I was alone.
And then I started to lookaround and talk to people and
they're like, yeah, I can't readvery well either or spell very
well, and I'm like oh okay, I'mnot alone.
Speaker 1 (26:02):
You know I always look for little comedy bits and
you're like you could be likehey, I used to cuss about it and
yell in front of that group andI'm just not gonna be let back
into the.
No, nothing.
Speaker 2 (26:19):
No, I mean, I think that I think that I was just
thinking about what.
I was just thinking about whathe said, and I was like you know
when, when I was young,anything that made me follow a
traditional learning path wasjust impossible.
But any, any area where theyallowed me to determine my own
(26:41):
learning path, I was reallysuccessful.
So I was thinking about, youknow, writing the book and what
I've done in business, andthat's creating the future
instead of using a future that'salready been created for you.
So maybe that's one of thereasons why you know I've been
successful with what I do isbecause I'm used to creating a
(27:02):
future instead of living in afuture that's created for me
I've been listening on theeducation piece for sure.
Speaker 1 (27:11):
You're a gen xer, right at least.
So we're talking not the mostaccommodating educational path
back.
You're like, really, what doyou know about?
Like I don't, but I assure youthat the kids are so amazing
inspiration.
Let me ask you a question.
If you could go back in time,though, at any point, when would
(27:32):
you go back and what would youdo differently?
Speaker 2 (27:36):
I would go back to COVID and I would um, I, I would
have taken advantage of youknow, whenever there's a
downswing in a market, there'san upswing around the corner.
Sometimes you got to wait forit, but it always happens, right
.
So, and it's the same thingwith life, right?
We all have peaks and valleys,and COVID was like a.
(28:01):
It was during the rise of ofeverything.
Everything was going up.
Covid happened and interruptedit.
It just continued after COVID,but it was built up because it
missed that rise.
So if you think about a, a riseover time, you know things are
going up over time and then allof a sudden it stops.
(28:21):
It just sort of paused it andit built up.
And then, all of that time thatwas paused, all came in in the
following two years, right,which created a artificial boom,
which created an economyscenario right, where it was
like everybody just held up andall the investors were like,
okay, we, we all have this loosepowder.
(28:42):
We got to go deploy this moneythat they were afraid to deploy
during COVID.
They deployed it, which overbloated the market, valuations
went way higher than they couldhave and that created a
fundamental problem in themarket.
If I had thought about this alittle bit more.
Instead of just reacting to thefact that we had the problem
which is what I did with myportfolio companies and my
(29:04):
company I was like I was likeholy smokes, we got to survive
because we don't know how longthis is going to happen I would
have been thinking about whathappens after this is over, and
that's what I would have changed.
I would have started thinkingabout what happens when this is
over instead of dealing withwhat's happening now.
I think it was short term,short sighted from a visionary
(29:25):
perspective.
Speaker 1 (29:27):
I wouldn't have worn a mask.
That's what I would have gonewith.
I just, yeah, Just breathe itin.
Let me do this.
You know I've said this a fewtimes in shows.
One of the funniest answersI've ever had to that question
is the guy goes I wish I wouldhave ordered a black coffee
instead of a latte today.
He's like but I'm gonna correct.
Speaker 2 (29:48):
I'm gonna correct that right after the show yeah,
that would be one of the bigthings I would change, I think I
think that's one of the reallyreally big things, uh.
And then I think the otherthing that I would change is
when I sold, so one of thecompanies I sold went to, sold
to eBay and was a rather largetransaction.
(30:10):
It's all over the internet youcan find it.
Um, and after that I boughtlike some supercars, you know, I
went through like Bentleys,ferraris, mclarens, lamborghinis
.
I would never have done thatagain.
That was the stupidest childishthing I have uh done.
I would.
If I look back on it, I wouldnot do that.
Speaker 1 (30:29):
It was just, um, you know which of those ones were
the were the most disappointing?
Speaker 2 (30:34):
the mclaren, really yeah, because I don't know if
you've ever gotten in and out ofit, but it's got one of those
doors that open up sideways uplike this, and it's like getting
into a bathtub.
So getting in nobody looks cool.
Getting in and out of a McLaren, it is extremely tough to get
in and out of this thing Onceyou're in.
It's also really small andreally bumpy and you're sitting
(30:57):
in like this bathtub thing.
I don't know, I just it wasjust not a nice car to drive.
Now a Bentley, on the otherhand, is amazing to drive, but
you know the now I just drive anold truck and you know cause?
I don't care.
Speaker 1 (31:11):
Well, it's funny, I don't have anywhere near your
wealth.
But I will tell you.
Uh, my next.
I am not a car guy.
Like you know, I I've beenrocking a paid-off minivan since
the day I got it in 2013.
Speaker 2 (31:20):
Nice man.
See, that's what I'm talkingabout.
That's cool.
Speaker 1 (31:24):
Over 200,000 miles.
I keep sinking about 5K into itto keep it alive because I got
a 15-year-old about to drive andI'm like I am keeping this car
for you guys.
You have three kids.
If I can get all three kids inthat car without dying or
killing the car, I haveaccomplished amazing feats.
But my next car will be a 50000 mile deep jeep.
Let me see, I will get they.
Look, because I've had one.
(31:45):
I loved it.
I don't know why I got rid ofit.
These four doors, I used tomake fun of them.
Now I'm kind of like I get it,it's yeah, I'm gonna get one and
it's gonna have a lot of mileson it.
Why?
Because they all look thegoddamn same after a while and I
don't even care.
I just want to have a fun carplus, I don't even care anymore.
Speaker 2 (32:01):
Like I, I have a 2016 dodge truck, right, and I love
this truck and, yeah, it's a rambefore it's a good year to ram
for the screw the engines upyeah, it's a bio diesel.
Um, you know so it uses regulardiesel bios.
It's a really.
It didn't?
Speaker 1 (32:19):
they only made 1500 of them um, um, wow, that's a
cool truck, that's, that's one.
That's one's going to be aroundfor a while.
Speaker 2 (32:26):
Yeah, it's really, really cool and I'm glad I have
it and I like it.
It makes me happy.
I like that.
It's old, I really do.
And when I was driving nicecars, all the time I always felt
like I was making other peoplefeel badly about their lives and
that affected me really.
You know, you look at somebodywho's working really hard and
they have an old car and theylook at you and you're in this,
(32:49):
you know $250,000 car, and youjust feel like a dick.
You know you just feel like adick and I just didn't want to
do that anymore.
And now I drive around witheverybody else and you know it's
.
I'm not making anybody feel bad.
Speaker 1 (33:03):
I love the fact that I can cut off any car and
they're going to get out of myway.
Maybe your truck You're like ah, he's worse.
So if you have a den or two ina car, people you can really
especially Teslas, cause theyrecognize that and they
immediately stop.
By the way, if you have a Tesla, you can always cut it off.
It will stop for them.
If I see a Tesla, I porch itbecause I know they'll pull back
(33:26):
for me.
Speaker 2 (33:26):
Well, nowadays, also with Elon Musk, everybody hates
their Teslas, so it's funny.
Speaker 1 (33:33):
Is he being aggressive or does he just know
my car?
Yeah, if I know you like yourcar more than mine, I can get in
front of you or take a turn infront of you for sure.
That's his gaming right there.
That's gamification.
All right, if there was aquestion I should have asked you
today, and I didn't, what wouldthat question have been?
Speaker 2 (33:50):
Ooh, wow, I've never been asked that.
That's a really good question.
Speaker 1 (33:55):
I pride myself on being in a fantastic hostess.
Speaker 2 (33:58):
I would say that what was the best decision I've ever
made.
Speaker 1 (34:02):
And how would you answer that?
Speaker 2 (34:03):
In, not in personal, because that's my wife right,
but in in business.
What was the best decision Iever made?
I think the best decision Iever made was to sell to eBay so
that one company DBA I mean my11th one.
I sold to eBay.
11th one I sold to eBay.
(34:25):
Um, and it was a huge, hugedeal.
And I went in and I uh ended upworking, working there and and,
uh, I was the chief strategyofficer and then I was the chief
technology officer for the.
You know, it's a lot, it's along process, but we went in and
it was all eBay enterprisemarketing solutions and then all
of that got bought out intothis separate company and then
we ended up selling off a bunchof these companies and then we
(34:47):
ended up buying another one ofmy companies and merging all
these things together and thenselling that three times.
That was a hell of a ride and,yeah, I was at the center of the
whole thing.
It was amazing, it was anincredible experience and a hell
of a ride and that wasdefinitely the best business
(35:07):
decision I've ever made.
Speaker 1 (35:09):
That's awesome.
I love that.
I imagine the night before thechecks about to hit, you're like
get in there, get in there dude, I could tell you this that the
night the wire came in.
Speaker 2 (35:24):
So the wire came in.
I'm looking on my phone and Isee it and I go to bed.
Right, I smoke a joint and thenI go to bed.
I'm just like so happy.
I wake up in the middle of thenight sweating with this
nightmare, that the chat, thatit was all a dream and it wasn't
real.
And I kept waking up, checkingmy phone and looking at the bank
balance, like over and over andover and over again.
You know doing this and Iremember it so clearly, going,
(35:45):
oh my god, because I would wakeup sweating like it was all a
horrible, like it was just adream and it was, you know, and
it wasn't real.
And then, and I mean you knowthat first day, that first week,
I would say, after you sell acompany is euphoric, uh, and
you're you.
It's hard to believe that ithappened.
You know you're sitting there.
I can't, it's hard to believethat it actually happened,
(36:08):
especially the big ones, the bigones.
You're just like, oh my God, Ican't believe.
I pulled this off.
This was like some vapor ideain my head, and then I turned it
into a business that peoplepaid millions for right Lots of
millions and you're sittingthere going.
I can't believe I pulled thisoff.
It's you know, it's amazing,and every time I do it I feel
(36:29):
the same way.
Speaker 1 (36:32):
Listen, and if your playbook's that book, I'm
reading it.
It's that simple.
Speaker 2 (36:36):
Yeah, you should read it.
It's pretty good.
It took me four years to writeit.
I will definitely do that.
Speaker 1 (36:39):
Uh, be uh the startup life cycle is the name of it.
It's pretty good.
It took me four years to writeit.
I will definitely do that.
B the startup life cycle is thename of it.
We'll put a link in the shownotes for sure.
Gregory, thank you so much forcoming on today.
I love it, thank you.
Thank you for your time andenergy.
I really appreciate it.
It's on me Listen.
(37:00):
Before, like I said, I wasn'tsure, but now I'm 100% sure.
I'm glad I interviewed you,gregory.
Thank you so much.
Hey, listen, go toGregoryShepherd with 1pcom and,
if you made it, this part in theshow, thank you so much for
listening and being a part ofour journey.
If this was your first timehere, I hope you come back.
But everyone listening, get outthere, go, cut a tie to
something holding you back.
Let nothing stop you, but firstdefine.
Welcome to the Cut the Tie podcast.
Hi, I'm your host, ThomasHelfrich.
I'm on a mission to help youcut the tie to whatever it is
holding you back from success.
As I always say, you need todefine that success yourself,
otherwise you're chasing someoneelse's dream.
Today, I am joined by MrGregory Shepard.
Gregory, how are you?
Speaker 2 (00:18):
Thank you for having me.
I really appreciate it.
I'm honored to be on your show.
I appreciate it so much.
Speaker 1 (00:24):
Well, I appreciate you being here as well.
We were having a briefdiscussion about coffee Today.
I may mumble, I just feel likemine's broken.
So if you hear a mumble and youtruly don't have a clue what I
said, just answer whatever youwant.
Speaker 2 (00:38):
Just however you like .
Speaker 1 (00:39):
I believe cats could be blue if you mixed them right.
Okay, that's fair.
All right, Gregory, let's do it.
Introduce yourself and what itis you do.
Speaker 2 (00:48):
My name is Gregory Shepard.
I have two websitesGregoryShepardcom and
StartupScienceio.
I am a 12-time entrepreneur 12startups, 12 exits, four private
equity awards for transactionsbetween $250 million and a
billion.
I'm the author of the StartupLife Cycle, a book based off of
(01:08):
five years of research onfounder failure and success.
I do a lot of speaking, tedTalk, I'm a Fulbright scholar
basically a lot of differentthings.
Sorry, I hate talking aboutmyself.
I feel like I have to do it allday.
Speaker 1 (01:25):
You know what?
It's only going to get worsebecause we're going to we're
going to peel some onions of you.
It's going to be great.
Okay, you're ready for thepauses of uncomfortable people?
Here we go, hey.
So before we dive in a littlebit to what you're doing, give
some the one link.
How many people, like, go intolike a two-minute rant?
(01:51):
I'm like and that link wasGregoryShepardcom Go stalk him
while he's speaking Okay, 12exits, that's a lot, and there's
a lot of books on these topics.
So I always kind of ask thislike unique identifier question.
But you know why?
Why you?
Why?
Why should they read your book?
Speaker 2 (02:15):
work with you.
I think I'm unique in that Icame from nothing and I've built
and sold 12.
So that's a really rare trackrecord, and the book is based
off of five years of research onfounder success and failure.
So I mean, I spent a half amillion dollars.
There was a couple hundredthousand case studies, thousands
of interviews.
It took five years with fivepeople to get the data.
Then I took all of that dataand found out that one of the
(02:40):
biggest problems based off ofall the research was that
founders didn't understand thelife cycle.
They thought that a round offunding was a phase, but that's
something that happens during aphase, but that's not the phase
itself.
So there's two things you needto know when you're starting
your company where you are andwhere you're going.
It's like a GPS.
So I wanted to do is to write abook that was the GPS, so they
(03:04):
understood where they're goingand what they're going to
experience along that path,hopefully preparing them and, by
doing that, offsetting thereasons why they fail.
Speaker 1 (03:17):
I love metaphors In that analogy, funding is no more
than a fuel stop you would justprepare where it is so you
don't run out of gas no morethan a fuel stop, you would just
prepare where it is.
Speaker 2 (03:25):
You don't run out of gas.
Yeah, that's part of thejourney, right, you have to.
Well, you have to if you'regoing on a road trip.
Right, you have to know whereyou're going to stop for fuel
and how long it's going to takefor you to get there, how much
it's going to cost.
When you're going to eat, whenyou're going to go to the
restroom, when you're going tostay the night time you're going
to start in the morning.
I mean, you have a whole planfor your journey, right?
Well, most entrepreneurs in myresearch didn't even know where
(03:50):
they were or where they weregoing, let alone planning a
journey.
So it's no wonder that a lot ofthem fail.
Right?
If you started a road trip andyou didn't have your destination
in the world of startups,that's your exit strategy.
If you don't have yourdestination when you world of
startups, that's your exitstrategy.
If you don't have yourdestination when you start, how
are you ever supposed to getthere?
You're going to run out ofmoney, time, energy during that
(04:15):
process before you even getthere.
Speaker 1 (04:19):
As a founder myself, that is very true, because
sometimes you're just so excitednot to be working for somebody.
Then you do raise a little bitof money and you realize I
probably raised oneone-hundredth of what I needed
to.
Yeah, You're like, ah, Becausecash flow, that's an important
piece If you really want rapidgrowth.
You're going to have toleverage, You're going to have
(04:41):
to get money in that's not yoursunless you're just
independently wealthy.
Yeah, you got to do somethingright.
You got to grow a cash registeror bring it in through.
You know there's some kind ofinvestment vehicle.
So, talking about your journeya little bit, though, but before
you do, I want you to definesuccess for yourself.
What is currently thatdefinition?
Speaker 2 (04:59):
Currently, my success is based off of helping
entrepreneurs succeed.
That is my life's mission now.
I mean, I've spent a lot oftime helping myself and now my
life is dedicated to helpingothers.
Speaker 1 (05:15):
I like that.
So you're measuring yoursuccess by the impact you're
having on others right now.
Speaker 2 (05:20):
Right.
Either social environmentalimpact innovation impact Right.
Either social environmentalimpact innovation impact right.
So if you look at the world,going back all the way to the
industrial revolution, even backto Henry Ford, et cetera
innovation is what drives ourplanet.
It drives everything, right,and that all comes from startups
(05:41):
.
Corporates don't innovate, theybuy innovation, right.
So, if you think about it, ifyou're helping founders this is
why this is my focus by helpingfounders, not only are you
helping those people that needfinancial equality why would
they be a founder if they werealready financially independent?
You're not seeing that, right.
You're seeing people who aretrying to make something happen
(06:03):
for themselves and their family.
So then you're helping withsocial equality, right.
Well, most of the technologythat you see now is technology
oriented towards changing things.
Right, it's either upgradingthe current technology, stacks
people using, etc.
But the big revolution istechnology impact into the
(06:26):
industrial revolution.
So they call it industrialinnovation or industrial
revolutionary technology, andthis is basically going back to
the industrial revolution andrebuilding everything that was
built before.
It's the biggest transformation.
Industrial transformation is thebiggest thing there is right
(06:46):
now.
Right.
So it happened with roboticsand now AI is stepping up on the
top side of it, and the two arecoming together to transform
things.
So this is like helping outwith the planet, right, because
part of the impact that we'remaking on the planet is making
it harder for us to live here,and that is reduced drastically
by industrial transformation viastartups, right?
(07:09):
So, from my perspective, if I'mhelping startups, I'm helping
out with the environment, I'mhelping out with social, I'm
helping out with innovation andI'm helping out with people,
right?
And so, to me, having my focusbe helping startups and those
that are helping startups isindirectly helping in all those
other capacities, and that's whyit's my life mission.
Speaker 1 (07:33):
I don't think the earth cares what we do to help
it, because it took a meteor andhere we are.
I mean it's like, yeah, I hitmy meteor.
Speaker 2 (07:41):
Yeah, it's not a matter of the earth is going to
be here, it's a matter of we'regoing to be here.
Speaker 1 (07:44):
Yeah, the earth doesn't care what we.
It will correct us, don't worry, we will.
If that was a human, the earthwas a human and eventually we
just get annoyed with the dirton its hands.
It's.
I'm just gonna shake a sleeve,hold my hair and get a haircut
and wash off and we'll see whathappens next.
Doesn't care I always.
Speaker 2 (08:03):
I always think of it like, like you know, when your
dog gets out of a out of waterand it shakes and it shakes off
the water, I always feel likethe earth is one day going to
get fed up with us and just belike all right, that's it, tired
of swimming.
Speaker 1 (08:15):
Yeah, you know, along your journey, tell me a little
bit about it and it and whatthat big, the biggest, maybe
metaphoric tie that you've had acut to find success today.
Speaker 2 (08:28):
I think that oftentimes people are like you
know what are the keys?
Like how can you just give methe hack right?
How do you do what you do?
You know how do I do all thesestartups and all these things
that I do?
How is that even possible foran individual to do?
And I say, first of all, thereare five things that you need to
(08:49):
be successful.
I call it a handful becausethere's five fingers in your
hand right Focus, drive,enthusiasm, discipline and
optimism.
I think if you have thosethings, then things like
organization, time managementthey fall under discipline,
right, and things likemotivation fall under drive and
enthusiasm is contagious and youcan't build anything without
(09:12):
having focus.
So I call it the handful ofthings you have.
So first thing I tell people isI'm like you need focus, drive,
enthusiasm, discipline andoptimism.
You need to like, get thosethings and attach to them and
make it part of your daily life.
And then the second thing is todig into those is time
management and organization.
I think time management andorganization are very linked
(09:35):
together.
If you're organized, you'reautomatically going to save time
.
Therefore, you have timemanagement.
The reason why they're separateis because time management
includes prioritization anddelegation right.
So I use tools like theEisenhower impact over effort
and urgent versus important formy priority metrics, and then I
(09:56):
use tools like the RACI, whichis responsible, accountable,
informed and consulted for mydelegation metrics.
And those are the things that Iuse and that's that's sort of
like real, real important keys,I think, for success.
So that's your hack.
Speaker 1 (10:14):
Like when you, when you, you know from the actual,
though, like kind of thing thatwas holding you back in life.
What's something that you'vehad to deal with to to overcome
yourself, Like this've had todeal with to to overcome
yourself.
Like this, I had to stop doingthis or I had to start doing
this, like everyone's got one.
What's your?
Speaker 2 (10:31):
yeah, I mean, I have autism and level five dyslexia,
so I read at like a fourth gradelevel, right and and like I
can't even read menus.
I have special tools to help meread menus.
Overcoming that before AI wasimmensely difficult.
It took me, you know, fiveminutes to write an email, even
(10:56):
a short email, because I have tohave the machine read it.
I have to dictate to themachine and then read to them
and then have it read it to meand then dictate and change it
and go back and forth, you know.
And now with AI, it's amazing.
But I think that's one of themajor things.
And the other thing had to dowith just and this is something
for all entrepreneurs isself-doubt and imposter syndrome
.
Right, like when you'rebuilding a business and
(11:19):
sometimes, if you're disrupting,you feel like you're standing
out there all by yourself.
Right, there's, there's nobodyelse out there but you and
you're, and you're like am I theonly one that sees this?
Apparently, I am.
Am I crazy?
Is this actually a goodbusiness?
What you know?
Why am I?
You know, I don't, nobody elseis out here, and it's you know.
You feel like you're standingin a desert and you're trying to
(11:40):
build a city and there's nomaterials, there's nothing.
So overcoming that self-doubtis a fundamental thing to
overcome, and it's not somethingyou overcome once.
It's something you overcome allday, every day oh yeah and I'm
just the oh good, no, no, you goahead.
No, no, no, you go ahead, okay.
(12:03):
And the other thing is thisimposter syndrome.
Like I mean, I speak at thesebig events in front of hundreds
of people, I've written books,I've been a chairman for
congressional candidates, I'vemet barack obama twice, I've
built all these businesses andsold them.
I've done all these thingsright and I still have imposter
syndrome.
Like I mean a hundred percent,like even on this podcast, I'm
(12:25):
like you know, am I worthinterviewing?
You know, like why?
Why do people want to even hearwhat I have to say?
So it is a really big deal andit happens to everybody.
It's not silo to you, listener.
A self-doubt and impostersyndrome happen to anybody that
is an entrepreneur.
And if it doesn't happen to you, then you're arrogant.
(12:46):
And if you're arrogant, youneed to step back and evaluate
you know, I was one of the samething.
Speaker 1 (12:52):
Am I going to really interview this guy?
And then now I've met you, I'mlike I'm surprised he's on this
podcast.
I'm so happy you flipped thescript on me.
Now I got the imposter syndrome.
How'd you do?
I don't even know what to donow at myself.
12 exits I can't.
I can't get, like you know, 12.
Um, just maybe a kind of asidebar.
(13:13):
Like you know lots of differenttypes of businesses.
Are you rinse and repeating thesame models?
Speaker 2 (13:19):
I mean, the startup life cycle is the method I use,
right, but the concept, the idea, is the art.
I always tell people this.
I'm like the idea is the art,but the execution of the
business itself is actually ascience.
And if you look up thedefinition of science, it
definitely explains the processof building the business after
(13:39):
you have the art, which is thevision in the first place.
Right, and there's two types offounders.
There's visionaries and subjectmatter experts.
And visionaries think from thetop down, from the outside in,
and subject matters expertsthink from the bottom up, inside
out.
Experts think from the bottomup, inside out, right?
(13:59):
So there's one of them islooking at something and saying,
oh, this is a disaster,somebody needs to do something
about it, and then they dosomething about it.
That's the subject matterexpert.
A visionary is looking at anentire system and they're saying
, oh, this whole thing is broken.
And then they work with subjectmatter experts.
So co-founders and foundersusually are good pairs, with one
being a visionary and one beinga subject matter expert.
(14:19):
So if you look at Steve Jobs,if you look at Bill Gates, they
all had subject matter expertsunderneath them and they were
the visionary.
And so you know, like Wozniakwas.
So I think that it's.
It's the the.
The fundamental thing for me islooking at problems as
(14:40):
opportunities, and I'll give youthe way I think about this.
Imagine a still pond.
The water is completely still,there's no water moving, and you
throw a rock at the center ofthat pond.
You get those rings that arecat happen.
So the rock would be adisruption.
So AI, the phone, the iPhone,the internet, robotics these
(15:02):
things are disruptions, right.
So the rock hits.
The first rings that appear arethe biggest opportunity, the
biggest rings, but there's notvery many of them because the
rings are really small at thatpoint.
But as that disruption is timedout, you know, over time you
start to see the ring spread outand those rings on the outer
(15:23):
side there's way moreopportunities.
They're not as big, but there'sway more opportunities.
I don't focus on the disruptionand I don't focus on the initial
rings.
I focus on what's on theoutside of that.
Why do I do that?
Well, there's this story ofLevi Strauss and everybody's
like oh, levi, levi, right, butnobody remembers the gold miners
(15:45):
.
What Levi did is he sold jeansto the gold miners, because the
gold miners needed pants to wearwhen they were gold mining.
Guess who was more successfulthe gold miners or the guy who's
selling the jeans right, or thepickaxe?
Either one Exactly, you get thepoint right.
So, basically, what I like todo is I consider the original
(16:08):
disruptors the people with thepickaxe and the gold pans, and
the need of jeans and et cetera,and the gold pans and the need
of jeans and et cetera and thenI look for things that I can
market to those people becausethey are the original
aggregators of the concepts, ofthe art, of the idea, right.
So that's sort of like my trick.
Speaker 1 (16:28):
I mean, there's no I'm glad to ask because we're a
marketing agency like my companythat focuses on primary
LinkedIn lead gen and, as I lookat it, we've pivoted more and
more to helping marketingagencies build a lead gen
company for themselves becausebecause that helps lots more
people, very focused, becausewe've done it.
(16:49):
So we're like why don't we justhelp other marketing agencies
do it right and for them?
Speaker 2 (16:54):
that's like a beautiful model, like if you the
train.
The trainer model is, I think,much better, because people want
that stuff in house.
It's too important, right?
So if you're teaching them howto do it in house, that is a way
better.
You're selling intellectualproperty as a much better
business model than sellingexecution.
Speaker 1 (17:13):
Well, and and so what we've found right and I think
this is really relevant and it'scalled instantly relevant
Didn't mean to put the pun inthere, but it's very relevant to
kind of, what I face, and I seelots of people face, is that we
have a couple of really niceclients that pay a good amount
of money for the really goodservices we do.
But we couldn't have gotten thatand we couldn't have trained
other marketing agencies unlesswe'd done it first.
(17:34):
And so we're about four yearsinto that journey and I'm like,
yeah, I don't, I'm 49.
I don't think I want to bedoing this 10 years from now.
I think I want to move thismodel to train the trainer.
But the next piece of that isbut who is it?
You know like, who do you nichedown to?
Because if you make it, evenfor coaches and marketing
agencies and consultants, you'renot selling anybody at that
(17:54):
point, right.
And so it's like you got tofigure out who can afford it,
who wants to do it, who wants topay for it, and and then you
know, show how to do it or whitelabel it with them or something
.
Speaker 2 (18:03):
so very important, and that's where I'm at right
now.
Speaker 1 (18:08):
Some of it's like who should I sell that training to?
Speaker 2 (18:11):
yeah, I mean, I'll tell you what I would do in your
situation.
Number Number one I would learnagentic AI, because agentic AI
can actually.
It's like having a team.
So what we did, as an example,is that there's a manager
believe it or not, there's an AImanager, a boss, and then the
AI boss has a bunch of employeesand each one of those AI
(18:34):
employees execute what the bosssets, but they delegate certain
pieces of it to a different AI,and so what you have is you have
a whole marketing team andthese little agents are telling
you know, one is telling thenext one what to do, which is
telling the next one what to doand how to do it.
Execute and bring it back tothe boss.
Right, this structure building,this is not something that you
(18:58):
can template.
You basically need to buildthis.
You can template the generalflow, but you got to go in and
modify it every single time.
If I was a marketing agentright now, I would be selling
not just the strategy ofmarketing itself, but I would be
selling, and not just theimplementation of the AI
(19:19):
marketing team, but the wholething.
Right, I would say we're goingto come in and, at the end of
the day.
The outcome is you're going tohave an automated, you know,
cold outreach LinkedIn campaignwhere it's generating unique
emails for every single prospect.
Blah, blah, blah, blah, blah.
Right, Like that's how I wouldbuild it.
And then I would sell theknowledge and I would also sell
(19:41):
the software execution, Becausewhere you're essentially selling
them is a full marketing teamguided by your expertise.
You know, that's what I need.
Speaker 1 (19:52):
It's actually very similar.
Just, I know we're kind of on atangent, but that is similar to
what we do, but it's actuallyvery similar.
Just, I know we're kind of on atangent, but that is similar to
what we do.
So we do show them amethodology, no matter what
technology exists, of process tofollow.
So you have a repetitive piecethat keeps the human in the
front and assisted by an AItechnology in the back, because
it's freaking amazing, that'samazing Because right now, ai to
AI agents aren't there.
(20:13):
Now, what I mean by that is, atsome point I'll have an AI agent
that filters all the things Imay or may not need and
occasionally I'll tell hey,listen, I kind of need help with
SEO.
It will go talk to other AIagents and say I think I found
two or three that may fit yourbill.
Do you want to meet with theowner?
That will happen and then allthe sales stuff will be done
through your AI's interactionsand stuff and the provability of
it and the verification, thepoint being within a journey.
(20:36):
I guess my point of this so I'mgoing to come back up is not
that.
You know, sometimes I get freecoaching on these things, guys.
It's just how it works.
Anyway, is that occasionally youhave to look at your own model,
because where you start, oftenfor a lot of founders in the
first, is they start with a jobthey've created for themselves
just so they can escape whateverthey came from to make money.
I did it.
Almost 95% of, not more ofentrepreneurs I met have created
(20:59):
a job for themselves.
What I think happens and whatyou're describing in the startup
cycle is um, the life cycle isto take that step, to be not
just in a job at a company youcan actually sell an asset and
to do that.
That's a process, that's afunction, that there's things
you need to do beyond the jobyou created for yourself.
Speaker 2 (21:16):
Yeah, fair enough, yeah, a hundred percent.
Like if you're, there'slifestyle businesses, which is
something where you're trying tosupport yourself, and growth
businesses, which are businessesthat you're trying to sell.
Right, and you usually raisemoney for growth businesses
because investors want theirmoney back, so you have to sell
it.
So what I specialize in are thegrowth businesses, and growth
(21:37):
businesses all have certainthings in common.
They all go through the samelife cycle and they all have the
same core drivers, so that'sgrowth margin and retention.
And growth margin and retentionare accountable by different
functional areas, and differentfunctional areas have different
key performance indicators.
And that is the same.
(21:58):
Whether you're building acompany that's selling agentic
software or you're building aCRM or whatever it is, it's
always the same and that's thepattern that's reoccurring.
And the reason why I've been sosuccessful is because I've
recognized this pattern,documented it and got really
good at following the pattern,and it works every single time.
If you just follow it, it worksevery single time.
(22:20):
The part it doesn't do is theidea.
Right, you have to have theidea, but outside of that, it
follows the system.
Same thing with what you do,right, somebody's like I want to
sell a widget and then you puttogether a process that sells
widgets the widget itself theyhave to bring to you, but the
system that you use is the sameregardless, right?
(22:41):
So that's what the book isabout.
That's basically.
Speaker 1 (22:46):
I'm definitely going to read it now that I have an
author that I can call and saywhat the hell did you mean by?
And I can throw this section.
Speaker 2 (22:52):
It's actually you know what I did.
I have an AI agent on mywebsite and it's trained on the
book and you can ask it anythingabout the book that you want
and it's just like talking to me.
It's amazing.
Speaker 1 (23:04):
You know it's funny with our own like kind of three
step or three kind of phase,nine step system that I have,
I'm like how could I get youknow AI, this, where this
becomes something that's uh, youinteract with an AI or some
form of an LLM, and so I'll takethat one offline with you what
your thoughts would be for that,because I think that becomes a
sellable asset that even you canembed strategy into the actual.
The IP could be in the strategythat sits behind the prompts,
(23:28):
right?
So you're going to give aninformation and the strategy
that you've given it is the IPthat you don't share.
So I'll take that one offlinewith you.
I want to move forward with you, though, so to learn more about
you.
This is awesome.
I'm so glad that I interviewedyou.
I was like man, am I sure aboutthis guy?
He may have imposter syndrome,and now we get free insult.
You know this is fantastic,thank you.
We're going to go longer, justbecause it's helpful to me and
(23:51):
it's my show.
Fuck, let's do it.
I can say one comment Dowhatever you want.
It's your show.
You can do whatever you want.
On your last day I found out aswell at work.
My kids said what if you didthis?
Like well, you could dowhatever you want on your last
day at work.
Guys, whatever you want.
Speaker 2 (24:05):
It's true.
It's true.
What are you most grateful for?
The same thing that I was, thatI absolutely hated about myself
or about, you know, the, the,the things I was born with, and
(24:28):
that is that, you know, myautism and my dyslexia have
really enabled me to see theworld and things completely
differently, and so, as a resultof that, it's it's it's just
drastically changed everything,right, like, I mean, it's just
like the way I see the world andthe and these things that I
think up and and all of thatstuff, it's all, it's all part
(24:52):
of the, the same, the way Ithink.
So, even though it's beenreally a struggle, like a
mountain of struggle, to getwhere I am, that struggle itself
has given me a lot of strength.
You know, if you think aboutstruggle overall, that's
evolution, right?
Plants that struggle survive.
(25:13):
Animals that struggle survive.
Over time they evolve.
So this has caused me to evolveinto a better person.
That's, you know, much betterat doing these things than I
would have been had it been easyfor me.
Speaker 1 (25:25):
So that's what I'm most grateful for was my
struggle it also gives youempathy that that would not be
there for others If you don'thave struggle.
It's hard to give empathy forsomething else, right, yeah,
you're kicking ass.
Hey, listen, there's a lot ofpeople who don't have dyslexia
(25:45):
that also read at a fourth gradelevel, just to be fair.
Speaker 2 (25:49):
That's true, there are a lot of I know, and I used
to think that I was alone.
And then I started to lookaround and talk to people and
they're like, yeah, I can't readvery well either or spell very
well, and I'm like oh okay, I'mnot alone.
Speaker 1 (26:02):
You know I always look for little comedy bits and
you're like you could be likehey, I used to cuss about it and
yell in front of that group andI'm just not gonna be let back
into the.
No, nothing.
Speaker 2 (26:19):
No, I mean, I think that I think that I was just
thinking about what.
I was just thinking about whathe said, and I was like you know
when, when I was young,anything that made me follow a
traditional learning path wasjust impossible.
But any, any area where theyallowed me to determine my own
(26:41):
learning path, I was reallysuccessful.
So I was thinking about, youknow, writing the book and what
I've done in business, andthat's creating the future
instead of using a future that'salready been created for you.
So maybe that's one of thereasons why you know I've been
successful with what I do isbecause I'm used to creating a
(27:02):
future instead of living in afuture that's created for me
I've been listening on theeducation piece for sure.
Speaker 1 (27:11):
You're a gen xer, right at least.
So we're talking not the mostaccommodating educational path
back.
You're like, really, what doyou know about?
Like I don't, but I assure youthat the kids are so amazing
inspiration.
Let me ask you a question.
If you could go back in time,though, at any point, when would
(27:32):
you go back and what would youdo differently?
Speaker 2 (27:36):
I would go back to COVID and I would um, I, I would
have taken advantage of youknow, whenever there's a
downswing in a market, there'san upswing around the corner.
Sometimes you got to wait forit, but it always happens, right
.
So, and it's the same thingwith life, right?
We all have peaks and valleys,and COVID was like a.
(28:01):
It was during the rise of ofeverything.
Everything was going up.
Covid happened and interruptedit.
It just continued after COVID,but it was built up because it
missed that rise.
So if you think about a, a riseover time, you know things are
going up over time and then allof a sudden it stops.
(28:21):
It just sort of paused it andit built up.
And then, all of that time thatwas paused, all came in in the
following two years, right,which created a artificial boom,
which created an economyscenario right, where it was
like everybody just held up andall the investors were like,
okay, we, we all have this loosepowder.
(28:42):
We got to go deploy this moneythat they were afraid to deploy
during COVID.
They deployed it, which overbloated the market, valuations
went way higher than they couldhave and that created a
fundamental problem in themarket.
If I had thought about this alittle bit more.
Instead of just reacting to thefact that we had the problem
which is what I did with myportfolio companies and my
(29:04):
company I was like I was likeholy smokes, we got to survive
because we don't know how longthis is going to happen I would
have been thinking about whathappens after this is over, and
that's what I would have changed.
I would have started thinkingabout what happens when this is
over instead of dealing withwhat's happening now.
I think it was short term,short sighted from a visionary
(29:25):
perspective.
Speaker 1 (29:27):
I wouldn't have worn a mask.
That's what I would have gonewith.
I just, yeah, Just breathe itin.
Let me do this.
You know I've said this a fewtimes in shows.
One of the funniest answersI've ever had to that question
is the guy goes I wish I wouldhave ordered a black coffee
instead of a latte today.
He's like but I'm gonna correct.
Speaker 2 (29:48):
I'm gonna correct that right after the show yeah,
that would be one of the bigthings I would change, I think I
think that's one of the reallyreally big things, uh.
And then I think the otherthing that I would change is
when I sold, so one of thecompanies I sold went to, sold
to eBay and was a rather largetransaction.
(30:10):
It's all over the internet youcan find it.
Um, and after that I boughtlike some supercars, you know, I
went through like Bentleys,ferraris, mclarens, lamborghinis
.
I would never have done thatagain.
That was the stupidest childishthing I have uh done.
I would.
If I look back on it, I wouldnot do that.
Speaker 1 (30:29):
It was just, um, you know which of those ones were
the were the most disappointing?
Speaker 2 (30:34):
the mclaren, really yeah, because I don't know if
you've ever gotten in and out ofit, but it's got one of those
doors that open up sideways uplike this, and it's like getting
into a bathtub.
So getting in nobody looks cool.
Getting in and out of a McLaren, it is extremely tough to get
in and out of this thing Onceyou're in.
It's also really small andreally bumpy and you're sitting
(30:57):
in like this bathtub thing.
I don't know, I just it wasjust not a nice car to drive.
Now a Bentley, on the otherhand, is amazing to drive, but
you know the now I just drive anold truck and you know cause?
I don't care.
Speaker 1 (31:11):
Well, it's funny, I don't have anywhere near your
wealth.
But I will tell you.
Uh, my next.
I am not a car guy.
Like you know, I I've beenrocking a paid-off minivan since
the day I got it in 2013.
Speaker 2 (31:20):
Nice man.
See, that's what I'm talkingabout.
That's cool.
Speaker 1 (31:24):
Over 200,000 miles.
I keep sinking about 5K into itto keep it alive because I got
a 15-year-old about to drive andI'm like I am keeping this car
for you guys.
You have three kids.
If I can get all three kids inthat car without dying or
killing the car, I haveaccomplished amazing feats.
But my next car will be a 50000 mile deep jeep.
Let me see, I will get they.
Look, because I've had one.
(31:45):
I loved it.
I don't know why I got rid ofit.
These four doors, I used tomake fun of them.
Now I'm kind of like I get it,it's yeah, I'm gonna get one and
it's gonna have a lot of mileson it.
Why?
Because they all look thegoddamn same after a while and I
don't even care.
I just want to have a fun carplus, I don't even care anymore.
Speaker 2 (32:01):
Like I, I have a 2016 dodge truck, right, and I love
this truck and, yeah, it's a rambefore it's a good year to ram
for the screw the engines upyeah, it's a bio diesel.
Um, you know so it uses regulardiesel bios.
It's a really.
It didn't?
Speaker 1 (32:19):
they only made 1500 of them um, um, wow, that's a
cool truck, that's, that's one.
That's one's going to be aroundfor a while.
Speaker 2 (32:26):
Yeah, it's really, really cool and I'm glad I have
it and I like it.
It makes me happy.
I like that.
It's old, I really do.
And when I was driving nicecars, all the time I always felt
like I was making other peoplefeel badly about their lives and
that affected me really.
You know, you look at somebodywho's working really hard and
they have an old car and theylook at you and you're in this,
(32:49):
you know $250,000 car, and youjust feel like a dick.
You know you just feel like adick and I just didn't want to
do that anymore.
And now I drive around witheverybody else and you know it's
.
I'm not making anybody feel bad.
Speaker 1 (33:03):
I love the fact that I can cut off any car and
they're going to get out of myway.
Maybe your truck You're like ah, he's worse.
So if you have a den or two ina car, people you can really
especially Teslas, cause theyrecognize that and they
immediately stop.
By the way, if you have a Tesla, you can always cut it off.
It will stop for them.
If I see a Tesla, I porch itbecause I know they'll pull back
(33:26):
for me.
Speaker 2 (33:26):
Well, nowadays, also with Elon Musk, everybody hates
their Teslas, so it's funny.
Speaker 1 (33:33):
Is he being aggressive or does he just know
my car?
Yeah, if I know you like yourcar more than mine, I can get in
front of you or take a turn infront of you for sure.
That's his gaming right there.
That's gamification.
All right, if there was aquestion I should have asked you
today, and I didn't, what wouldthat question have been?
Speaker 2 (33:50):
Ooh, wow, I've never been asked that.
That's a really good question.
Speaker 1 (33:55):
I pride myself on being in a fantastic hostess.
Speaker 2 (33:58):
I would say that what was the best decision I've ever
made.
Speaker 1 (34:02):
And how would you answer that?
Speaker 2 (34:03):
In, not in personal, because that's my wife right,
but in in business.
What was the best decision Iever made?
I think the best decision Iever made was to sell to eBay so
that one company DBA I mean my11th one.
I sold to eBay.
11th one I sold to eBay.
(34:25):
Um, and it was a huge, hugedeal.
And I went in and I uh ended upworking, working there and and,
uh, I was the chief strategyofficer and then I was the chief
technology officer for the.
You know, it's a lot, it's along process, but we went in and
it was all eBay enterprisemarketing solutions and then all
of that got bought out intothis separate company and then
we ended up selling off a bunchof these companies and then we
(34:47):
ended up buying another one ofmy companies and merging all
these things together and thenselling that three times.
That was a hell of a ride and,yeah, I was at the center of the
whole thing.
It was amazing, it was anincredible experience and a hell
of a ride and that wasdefinitely the best business
(35:07):
decision I've ever made.
Speaker 1 (35:09):
That's awesome.
I love that.
I imagine the night before thechecks about to hit, you're like
get in there, get in there dude, I could tell you this that the
night the wire came in.
Speaker 2 (35:24):
So the wire came in.
I'm looking on my phone and Isee it and I go to bed.
Right, I smoke a joint and thenI go to bed.
I'm just like so happy.
I wake up in the middle of thenight sweating with this
nightmare, that the chat, thatit was all a dream and it wasn't
real.
And I kept waking up, checkingmy phone and looking at the bank
balance, like over and over andover and over again.
You know doing this and Iremember it so clearly, going,
(35:45):
oh my god, because I would wakeup sweating like it was all a
horrible, like it was just adream and it was, you know, and
it wasn't real.
And then, and I mean you knowthat first day, that first week,
I would say, after you sell acompany is euphoric, uh, and
you're you.
It's hard to believe that ithappened.
You know you're sitting there.
I can't, it's hard to believethat it actually happened,
(36:08):
especially the big ones, the bigones.
You're just like, oh my God, Ican't believe.
I pulled this off.
This was like some vapor ideain my head, and then I turned it
into a business that peoplepaid millions for right Lots of
millions and you're sittingthere going.
I can't believe I pulled thisoff.
It's you know, it's amazing,and every time I do it I feel
(36:29):
the same way.
Speaker 1 (36:32):
Listen, and if your playbook's that book, I'm
reading it.
It's that simple.
Speaker 2 (36:36):
Yeah, you should read it.
It's pretty good.
It took me four years to writeit.
I will definitely do that.
Speaker 1 (36:39):
Uh, be uh the startup life cycle is the name of it.
It's pretty good.
It took me four years to writeit.
I will definitely do that.
B the startup life cycle is thename of it.
We'll put a link in the shownotes for sure.
Gregory, thank you so much forcoming on today.
I love it, thank you.
Thank you for your time andenergy.
I really appreciate it.
It's on me Listen.
(37:00):
Before, like I said, I wasn'tsure, but now I'm 100% sure.
I'm glad I interviewed you,gregory.
Thank you so much.
Hey, listen, go toGregoryShepherd with 1pcom and,
if you made it, this part in theshow, thank you so much for
listening and being a part ofour journey.
If this was your first timehere, I hope you come back.
But everyone listening, get outthere, go, cut a tie to
something holding you back.
Let nothing stop you, but firstdefine.
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Welcome to Bookmarked by Reese’s Book Club — the podcast where great stories, bold women, and irresistible conversations collide! Hosted by award-winning journalist Danielle Robay, each week new episodes balance thoughtful literary insight with the fervor of buzzy book trends, pop culture and more. Bookmarked brings together celebrities, tastemakers, influencers and authors from Reese's Book Club and beyond to share stories that transcend the page. Pull up a chair. You’re not just listening — you’re part of the conversation.
On Purpose with Jay Shetty
I’m Jay Shetty host of On Purpose the worlds #1 Mental Health podcast and I’m so grateful you found us. I started this podcast 5 years ago to invite you into conversations and workshops that are designed to help make you happier, healthier and more healed. I believe that when you (yes you) feel seen, heard and understood you’re able to deal with relationship struggles, work challenges and life’s ups and downs with more ease and grace. I interview experts, celebrities, thought leaders and athletes so that we can grow our mindset, build better habits and uncover a side of them we’ve never seen before. New episodes every Monday and Friday. Your support means the world to me and I don’t take it for granted — click the follow button and leave a review to help us spread the love with On Purpose. I can’t wait for you to listen to your first or 500th episode!
Dateline NBC
Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com