May 13, 2025 • 29 mins
What do addiction recovery, international web hosting, youth boxing, and AI-powered solopreneurship have in common? Ken Cox.
In this raw and inspiring episode, Ken shares how hitting rock bottom sparked a complete life overhaul—from buying a boxing gym to launching tech ventures that run on AI. If you're stuck overthinking, this episode might just be the wake-up call you need. Let's get to work.
Being a solopreneur is awesome but it’s not easy. It's hard to get noticed. Most business advice is for bigger companies, and you're all alone...until now. LifeStarr's SoloSuite Intro gives you free education, community, and tools to build a thriving one-person business. So, if you are lacking direction, having a hard time generating leads, or are having trouble keeping up with everything you have to do, or even just lonely running a company of one, be sure to check out LifeStarr Intro!
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Episode Transcript
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Carly Ries (00:00):
You're about to meet a solopreneur who rebuilt his
(00:03):
life from the ground up. In thisepisode, Ken Cox shares how a
diagnosis, a boxing gym, and arelentless drive to get to work
pulled it from addiction andpropelled him into tech
innovation. In this episode, Kendrops gold for anyone feeling
stuck, overwhelmed, or ready tofinally make the leap into
solopreneurship. If you've everdoubted your next move, this
(00:25):
episode will light a fire.You're listening to the Aspiring
Solopreneur, the podcast forthose just taking the bold step
or even just thinking abouttaking that step into the world
of solo entrepreneurship.
My name is Carly Ries, and mycohost Joe Rando and I are your
guides to navigating this crazybut awesome journey as a company
(00:46):
of one. We take pride in beingpart of LifeStarr, a digital hub
dedicated to all aspects ofsolopreneurship that has
empowered and educated countlesssolopreneurs looking to build a
business that resonates withtheir life's ambitions. We help
people work to live, not live towork. And if you're looking for
a get rich quick scheme, this isnot the show for you. So if
(01:07):
you're eager to gain valuableinsights from industry experts
on running a business the rightway the first time around or
want to learn from the misstepsof solopreneurs who've paved the
way before you, then stickaround.
We've got your back becauseflying solo in business doesn't
mean you're alone. Ken, it's sofunny because we've been talking
offline for the past fewminutes, and I feel like we
(01:28):
should have pressed recordbefore we actually hit record
because I have just already soenjoyed chatting with you. You
are just a ray of sunshine. Youhave the best shirt on that
reflects that as well. And we'rejust so thrilled to have you on
the show.
Thank you for coming today.
Ken Cox (01:42):
Thank you for having me, Carly. I appreciate it. You
too, Joe.
Carly Ries (01:45):
Yeah. And I wanna just dive right in because I'm
so intrigued by your story. Youhave a journey from addiction
recovery to tech innovation. AndI think it's just incredible. So
are you able to share that storyand discuss kinda what mindset
shifts helped you go frombasically rock bottom to running
multiple businesses?
Ken Cox (02:04):
Yeah. So I've always run multiple businesses. And
quite honestly I used drugs andalcohol as a crutch to help me
for a very very long time. AndI've had to do a whole
transition to learn how to sella completely different way. Like
do business a completelydifferent way because before you
know I could turn happy hoursinto business on a regular
(02:26):
basis, right?
And I realized that that waswell, my doctors, the judges, my
wife, they all realized that Ihad a problem way before I ever
did. And I had to overcome that.but back about ten years ago I
was diagnosed with liverdisease, alcohol related liver
(02:48):
disease. And the doctor saidquit drinking or you've got
about two years. And so I had tofind a process to do that and
quite honestly I was really,really mad about it for a long
time. And struggled to quit fora very long time until I had a
couple of epiphanies.
But those epiphanies camebecause the first thing that I
(03:08):
did when I decided to quitdrinking, take it seriously, was
I found a boxing gym and Istarted going there regularly.
Being in business my entire lifeand running small businesses and
large businesses, it became veryobvious to me that this business
was not going to last very long.So I reached out to the owner,
I'm like, hey, you need to letme buy this gym so it stays here
because if I don't have the gymthat I like, then I'm gonna die.
(03:32):
So I bought that gym from him.Grew that business on the side
while I was still running RiverCity and very very challenging
time for the company as a wholeand for myself at the same time.
I just lost my predecessor, mymentor Steve, and I was going
through all this other medicalissues that I had. But through
(03:55):
this journey, we started a youthboxing team and I became a youth
boxing coach. And one thing thatthe trigger moment for me is
when I realized that I had totreat coming out of addiction
like like I was coaching myselfto change my mindset of who I
was and change who I identifiedwith. And that was the entire,
(04:17):
the crux of the book ReclaimSobriety was changing who you
identify as is a huge step inany direction you wanna go. So
if you wanna quit drinking,wanna become an entrepreneur,
you wanna do any of thosethings, start identifying as
what you wanna be and do thethings that that person would
do, and that's what you willbecome.
Carly Ries (04:37):
That is wild. So you said you could turn any happy
hour, any night out into abusiness meeting. What do you do
instead now for your businessmeetings, and how do you keep
those relationships going in anew environment?
Ken Cox (04:51):
Well, lot more challenging today for business
as a whole, I think. Not only,you know, can I not go to the
bar and meet new clients and dothe happy hours and do the
networking and be the life ofthe party, right? I can still
try to be the life of the party,right? I can wear a fancy shirt,
I can put on a smile and I canshake hands and meet people. But
(05:13):
you know, I did a lot ofinternational business prior to
not drinking.
And I just don't do that kind ofbusiness any longer.
I transitioned. I like to do alot of business with small and
medium sized businesses, owneroperator businesses, and
implement services that have areally great value for that
(05:34):
company at a really affordableprice. And I think that that has
been the part of the turningstone for me of transitioning to
the type of sales that I didbefore, to the type of sales
that I'm doing now. It's abigger grind, and you know I'm
not swinging for the fencesnearly as much as I used to.
But that also might be age.
Carly Ries (05:57):
There you go. Well, Ken, what I find so fascinating
about you is you keep saying,oh, I've been running all these
businesses. I used to dointernational businesses and all
this, and it sounds like youhave a gazillion businesses. So
you're an entrepreneur, you havethe entrepreneurial spirit, and
you call yourself unemployable.And I'm curious what that means.
And at what point in your careeryou went from corporate and
(06:20):
decided not only am I goingsolo, but I'm never gonna be
employed again.
Ken Cox (06:26):
It was a long journey. I started my first company at
the age of 14 doing vendingmachines. I sold my first
company, video productioncompany at the age of 19 and I
went to work for them. When Iwas going through school and I'm
super fortunate and a derelictin so many ways, right? My mom
(06:48):
was working at WashingtonUniversity so I got free
tuition. I graduated frombroadcast center and then I
transferred to WashingtonUniversity, which is an amazing
Ivy League school. Ended updropping out of there and
transferring to Webster. While Iwas at WashU, was working there.
That was my last kind of bigcorporate job where I was not a
piece of the company, right?From there I went and I traveled
(07:12):
the country with musicians,being stage manager.
In 1999 I started, I left theentertainment industry, film and
video, and I went into IT.Specifically, for a couple days
I was doing DSL sales. If youremember DSLs in '99, we were
(07:33):
the first to market. Fastestgrowing company in the country.
I was just an employee at thetime.
And I took the job until I gotmy next entertainment gig. That
was literally it. I didn't wantto go to Japan with the tour
that I was on. So I told my bossI guess, to find me another tour
that's in The United States.During that process, I got a
(07:54):
chance to move into the webhosting world.
Because I went to WashU, I knewHTML in '99, I knew FTP, I knew
all these things. And I can tellyou a quick little story if you
like to hear it on how thetransition went and where I fell
in love with web hosting. I'msitting in an office taking
calls selling DSL right. It'sbasically order taking. Somebody
(08:17):
walks in the office and like whoknows how to FTP and I raise my
hand.
And at the time if you canimagine you know, my hair was
maybe two or three inches longand spiky and was probably
yellow or purple or some crazycolor. And I raised my hand
like, oh I know how to do that.And like, follow me. So we
walked down the hall and aswe're walking down the hall more
(08:37):
suits show up and they'rewalking with us and we get to
this other office and they'relike, okay, we need these files
up on this server. So like, noproblem.
And at the time it was aMacintosh. So I downloaded Fetch
and transferred the files. Like,not a big deal at all in my
head. And that website wasMasterCard.com.
But I was uploading. And mymentor, I didn't know him at the
(09:02):
time but he became my mentorvery quickly, looked at me and
he says you now are in the webhosting department. And now I
get huge clients. Like the veryfirst client I used was
MasterCard. And I had WonderBread was my very next big
client.
So working on Twinkies.com andfound myself in the lawsuit. If
you wanna Google theTwinkies.org lawsuit. It was a
(09:26):
big debacle for a very longtime. And I fell in love with
that world. And I startedhelping small businesses and big
businesses build the websitesand help with their operations.
And it was crazy chaotic. But byFebruary the world was changing
drastically really reallyquickly. Got super rich with
(09:46):
stocks and then super poorinstantly because the stock
market crashed. Right? And I gotin some trouble with the IRS.
So I picked up a job bartendingat night while I was doing all
this other stuff to try to payoff some debt. And one day my
predecessor Steve, the guy thatbrought me into the web hosting
department walks into the barthat I was working at and says,
hey we're starting a web hostingcompany. I said I'm in. I'm like
(10:10):
what do you need?
And so we started the webhosting company and that's where
I learned internationalbusiness. Because I couldn't get
customers in The United Statesbecause of my non compete that I
currently had with the companythat I was working for. So
started writing articles,sending them out all over the
world. Very first customer wegot was a company called IU
(10:31):
Kuwait. It was like a KuwaitiNapster. And it was really cool
and I just fell in love withthat kind of dodge and weave.
The company that I was workingfor at the time was going under.
And we had the opportunity tobuy all the web hosting
customers that the company thatI worked for was hosting. And we
(10:55):
raised the money and executedthat and that was kind of the
birth of Posturion for you know,we started and within six months
we were over a million revenuewith that one acquisition.
Joe Rando (11:07):
And what year was that? When was that?
Ken Cox (11:10):
That was, we started Hosteering in February, mid '2
thousand.
Joe Rando (11:14):
So post crash but not much post crash.
Ken Cox (11:18):
Correct. Post the VC crash but the services still
needed to be served, right? Sothey weren't fake services but
they were definitely acquired.The customer acquisition cost
was outstanding and theoperational cost was
outstanding.
I've always been really goodwith operations and I've been
able to cut through a lot ofthis crap really quickly.
(11:39):
Growing up as a dyslexic kid,always on a keyboard because
that's how I got to turn myhomework in. Loved technology so
I knew Linux just kind oforganically. I knew how to
manage through Linux and work oncomputers. So I was a natural
fit to run the operations forthe company.
Carly Ries (11:57):
So the thing that I'm also getting from this is
you had a lot of experiencebefore you flew solo. And for
people that are wanting tobecome solopreneurs and they're
listening, but they haven'tquite make the jump, look at
everything you're doing rightnow as education for when you
actually jump intosolopreneurship. It sounds like
you had some incredibleexperiences that really set you
(12:21):
up. So people that are kindagetting antsy and aren't quite
making that leap, I guess, wouldyou agree like your turn will
come, but just look ateverything you're doing right
now as a building block to makethat leap?
Ken Cox (12:33):
Yeah. I mean you know we all have these ideas of how
we want it to unfold. And it'snot gonna unfold that way. So
you know, just start moving,start setting things up, And
then look for the opportunities.Constantly looking for
opportunities that you canexecute on.
And you'll find opportunitiesthat you can't, that you're not
(12:53):
gonna be able to execute on forone of a thousand different
reasons. Generally finance oroperations capability, right?
Those are the two kind of bighurdles in the world. But I mean
both of those hurdles aregetting way smaller by the
minute with AI and technology.Like those hurdles to get
started are really getting low.
(13:15):
And I've always told people,look at your current job to see
if you can buy pieces of therevenue. Or buy some revenue
right out of the gate to kind ofget yourself stable and sturdy.
That works really great forservice based business. You know
other solopreneurs, common likecoaches and physical fitness
people, they gotta build theirown infrastructure and their own
(13:39):
client base. It's much harder tobuy that book.
Joe Rando (13:42):
You know, one of the things of your story that I
think is really, reallyimportant is the the FTP, which
stands for file transferprotocol. So you're basically
sending files from a computer upto the Internet, if you will. In
those days, it wasn't the cloud,but and to you, you were like,
this is easy. And yet there werea whole bunch of people in the
room that were, thinking youwere working magic. And I think
(14:05):
that's somethingsolopreneurs need to think about
is the fact that things that areeasy to you, that are obvious to
you, that you clearly think arejust, you know, nothing can be
really powerful for somebodythat doesn't know what you know.
Ken Cox (14:19):
Absolutely. And knowing how to do something that
somebody else doesn't know howto do is always a very valuable
valuable asset. Now AI is hereand anybody can know how to do
almost anything within a coupleof mouse clicks and a couple of
phrases they type in. But beingable to execute on that is what
it's all about
Carly Ries (14:41):
Yeah. Absolutely. Well, being able to execute,
you're talking about like justtaking everything and just doing
it. So suffice to say, let's getto work.
Is that your mantra? have youhad that mantra forever? Did
that start with the gym when youpurchased it? Where did that
come from and how can you applyit to solopreneurs who are kind
(15:04):
of stuck overthinking instead ofjust doing it?
Ken Cox (15:08):
So I'll tell you the story where get to work comes
from. my lawyer is an older man.I'm gonna say late seventies,
early eighties. And he loves totalk because he loves to run up
the bill. And every single timehe'd call me, we would sit and
we'd have these conversationsand he loves boxing and he's
(15:33):
a pretty high up there attorney.
We would talk for a while andI've learned so much from this
man. But at the end of everyconversation he'd say, alright
Ken get back to work. And I'mlike okay. And it was so funny
that every time I got off thephone with him I realized man
(15:53):
I'm really productive for aboutforty five minutes because
somebody just said okay can getback to work. And I would just
do it.
And I'm like man that's prettypowerful. So how can I make that
my own and just get to work? Andwhat I realized is that just
saying simple phrases to peoplehelps them, helps me do, take
that action. Right? So get towork became my hashtag.
Carly Ries (16:16):
Want that so much. And I think it's so funny,
you're right. It's a quicksentence but can be so
motivational for people that arejust kinda stuck in a rut.
Ken Cox (16:24):
Yes.
Carly Ries (16:25):
So Ken, my other question is that you say that
anything can be a businessbasically. So I'm curious, what
is the wildest or mostunconventional idea you've seen
someone turn into a profitablebusiness?
Ken Cox (16:41):
I have a friend that that started Hempster. And he
did this is pre THC being legalin most countries or most states
in the country. And he was a bigfan and he started just making
these little boxes and andputting different items in
there, and then shipping themout. Now where it becomes
(17:03):
brilliant is he was trying tofigure out how to make that more
profitable. And so he found out,Are you familiar with rolling
papers?
Mhmm. And he realized that mostrolling papers in the world were
made by slave labor. And flewoverseas and did a whole lot of
(17:25):
research. Ended up creating hisown rolling paper manufacturing
company. And removed all thesepeople from basically slave
labor.
Started paying them good wagesand now was one of the largest
rolling paper manufacturers inthe world. This is over the last
ten years right? Sounconventional as you look at an
(17:46):
industry like that you think manthere's no way I could get into
that at all. But you know hecreated a really good customer
base that would use that productprior to starting the
manufacturing.
And then started themanufacturing and kept going.
Some of the other businessesthat I really love today, and I
think that this is really moreimportant than anything right
(18:08):
now, are the service basedbusinesses in local communities.
I think they're so important.The dog waste pickup companies,
the trash removal companies, thepower washing companies. All of
these businesses forsolopreneurs that they can get
started with very low overhead,provide a very valuable service
(18:31):
in their community, hireanywhere between two and twenty
different employees to kind ofexecute on all these different
jobs to do.
And the beautiful thing now isthat the tech is here to support
them at a price that is wildlyaffordable. You know so it's no
longer that they gotta do stuffon spreadsheets and just quick
book invoices. They can have alot of automations and things
(18:51):
like that today. And just have areally really cool life. And I
love what the kids are doingwith art today.
Like making creative stuff andselling it. The spin art with
different team logos on it andstuff like that, think is so
creative and fun that I thinkyou know, it's a beautiful world
(19:13):
for the future. And podcastingis probably one of the biggest
that's happened over the pastfive or ten years that I think
the maturity of podcasting isgetting so much better that
people are able to start apodcast and make a make a living
off of a podcast with just acouple people.
Carly Ries (19:34):
Yeah. It's wild. I agree. You can really turn
anything you're passionate aboutinto business if you really
think through it.
But one thing I wanted to pickyour brain about is you said
you're really good withoperations and kind of building
systems and everything. So I'mcurious about this ten day to
change everything strategy thatyou have. what is that exactly
and how can you apply it tosolopreneurs?
Ken Cox (19:56):
So ten days to change everything. We're getting ready
to launch and I think it's gonnabe out before this episode comes
out. What we did, and it'schanged quite a bit while we're
building it, is we have 10custom GPTs created that were
given with the program and we'reteaching people how to use those
(20:17):
GPTs. They're chat GPTs butthey're custom GPTs starting
with business foundation. How towrite my business plan.
How to write my marketing plan.How to write my brand kit,
right? And a GPT that's designedfor those functionalities.
There's another GPT that's allabout legal business stuff. How
do I get my LLC form?
(20:38):
Should I do LLC or S Corp? Youknow all of those questions. And
we just walked through ten daysof, I'm assuming that a lot of
solopreneurs and businessoperators have been through at
least one or two differentcourses on how to start a
company, right? And they're all,and I've been through hundreds,
(21:00):
they're all about the same,right? There's a process that
you go through.
So we created ten days that helpyou use AI to create all of
those processes for you.
Carly Ries (21:10):
Oh wow. And that's yeah. For solopreneurs, that's
invaluable. And this isn't yourfirst rodeo with technology. You
I mean, obviously you were justtalking about it, but InLink is
also one of your businesses.
Ken Cox (21:21):
Yes.
Joe Rando (21:21):
It's filled with a plethora of tools.
Carly Ries (21:24):
So in your opinion, AI aside, what is one tool you
think solopreneurs should havestarted using yesterday that
they may not be using today?
Ken Cox (21:34):
Without AI?
Carly Ries (21:36):
Well I guess you can use AI. Don't use Chat GPT.
Ken Cox (21:38):
AI employees I think are, what we're telling most
businesses right now especiallythe solopreneur, main street
America, brick and mortarcompanies. If you have a front
desk role today, somebodyanswering the phone, sending
emails, sending text messagesand I'm gonna use the
eightytwenty rule but it'sreally probably like 99/1 . 99%
(22:01):
of those phone calls, textmessages and emails are the same
answer. Here's the form tocancel. Here's the form to put
you on hold.
Here's the form to get booked toyour next appointment. Right?
All of those things and AI doesa wonderful job today of picking
up the phone and answering allthose questions. Sending them
text messages. Answering youremails, sending them back.
(22:24):
So InLink's big movement isteaching people how to create AI
employees, but also in a mannerwhere they understand that those
AI employees still need to bemanaged, right? So this is the
staff that we believe should bereplaced by your transient
staff. Your college kids thatare coming home for the summer
(22:47):
And not saying you shouldn'thire them, but you should hire
them to manage your AI employeesand oversee them and spot check
those calls and spot check thoseGoogle reviews that they're
answering and spot check theemails that responding to.
Because like any employee, an AIemployee can get off the scope.
(23:08):
Specifically if they go off ascope and that off scope task
gets reinforced multiple times.
You know, you can have an AIthat thinks it's Spanish if it's
English speaking kind of thing.So it needs to be managed and
watched. But they work twentyfour hours a day, seven days a
week. They don't take vacationand the correcting their
(23:32):
behavior is a non emotionalevent.
Carly Ries (23:34):
Interesting. Yeah. Well, and just so that we're
clear on terminology, because alot of times in this show we
just say contractors becausethey're people that don't hire
employees. So like potato potatoin this Right. But just for
consistency purposes.
Ken Cox (23:48):
Yes. But we've all been on the phone with one client and
the phone's ringing and thatphone has, that call has to go
to voicemail. And today itdoesn't. It could be picked up
by an AI employee or we'reworking with a client, right?
The chiropractor or the HVACtech is you know literally
spinning wrenches servicingtheir client and the phone's
(24:10):
ringing.
I think the stats somewhere on60% of calls to small businesses
go unanswered. Right? And everyone of those unanswered calls is
a potentially missedopportunity. And then not even
the extra added benefit is thatyou never have to answer a spam
call again. Yeah.
Because your AI employee's gonnajust get rid of that really
(24:30):
quickly.
Carly Ries (24:31):
It's so weird just living in the wild wild west.
I mean, ChatGPT, I meanmainstream usage of it just came
out just over a year ago. Right?I was trying to think of when
people really started using it.
Ken Cox (24:48):
when GPT three five came out, I instantly knew that
it was different. And I signedup MIT has a really nice
program. It's a I think it'ssixteen weeks and it's AI for
business. And it's not even anhour after GPT 3.5 was
introduced to me was I signed upfor that course and went through
(25:11):
it. AI is changing, going tochange everything that we do.
AI, coupled with robotics, youknow, don't think the world even
understands where we're gonna bewith robotics in five years.
Joe Rando (25:26):
Have you seen the newest bots in Dynamics humanoid
robots?
Ken Cox (25:30):
Yeah. It's crazy. I have now robots that are mowing
my lawn and snow plowing mylots.
Carly Ries (25:38):
Are you serious?
Ken Cox (25:39):
Absolutely.
Already. And they're doing aphenomenal job. The robotics
coupled with AI is a juggernautof performance that is so
profound that the world's goingto change. I'm not sure exactly
(26:01):
where we're gonna end up in thiswhole world. I know that you
know the laborers and the unionsare really trying to hold on to
where they're at.
But humans are gonna lose thisbattle for labor. Robots and AI
are gonna take it.
Carly Ries (26:17):
You guys, I think I need a nap. My brain just
exploded. Oy. Well, we could godown this rabbit hole all day
and have not only an entireepisode on it, an entire new
podcast to talk about it? Andthe robots can do the podcast
for us.
Ken Cox (26:33):
And they are.
Carly Ries (26:35):
I know.
Ken Cox (26:37):
Like, you're probably following somebody on TikTok
that doesn't exist.
Carly Ries (26:42):
I know. You guys, I have a confession. I am also a
robot. So we've been interactingwith AI this entire
conversation.
Ken Cox (26:51):
How would we know?
Carly Ries (26:52):
Exactly. You wouldn't Ken, this has been such
a treat. You're a joy to talkto. We ask all of our guests
this question. What is yourfavorite quote about success?
Ken Cox (27:02):
Don't let yesterday take up too much of today. And
that's Will Rogers.
Carly Ries (27:07):
Oh. I like it. Very cool.
Joe Rando (27:11):
We haven't had that one yet.
Carly Ries (27:12):
Yeah. It is.
Ken Cox (27:13):
Cool. But Will Rogers is pretty old. Yeah.
Carly Ries (27:19):
Well Ken, you have so much going on. Where can
people find you if you wannalearn more as well as learn more
about the ten day challenge?
Ken Cox (27:27):
Yeah. You wanna know more about the ten day challenge
or join our AI workshop onTuesdays, just go to Inlink.com.
That's inlink.com. You wannaknow more about me and my
shenanigans just KenCox.com
Joe Rando (27:40):
And a question, did I hear something about a book?
Ken Cox (27:43):
Reclaim Sobriety is my book. Super proud of it. It's
one of the things that I'm mostproud of in my existence today.
It's been adopted.
We got it. It's in every libraryin The United Kingdom's prison
system. As a mindset shiftinghelper or assistant. So, yeah.
(28:05):
It's a ton of fun.
That's awesome.
Carly Ries (28:08):
So check that out too. Well, Ken, thank you so
much for coming on the showtoday. Listeners, thank you so
much for tuning in today. Asalways, please leave that five
star review. We would love it ifyou would subscribe on your
favorite podcast platform, andplease share this episode with a
friend.
A lot of people need to behearing this information or be
terrified of AI and roboticsthat are coming our way our way.
(28:29):
But we will see you next time onthe Aspiring Solopreneur. And,
Ken, let's get to work. You maybe going solo in business, but
that doesn't mean you're alone.In fact, millions of people are
in your shoes, running a oneperson business and figuring it
out as they go.
So why not connect with them andlearn from each other's
successes and failures? AtLifeStarr, we're creating a one
(28:51):
person business community whereyou can go to meet and get
advice from other solopreneurs.Be sure to join in on the
conversations atcommunity.lifestarr.com.
You're about to meet a solopreneur who rebuilt his
(00:03):
life from the ground up. In thisepisode, Ken Cox shares how a
diagnosis, a boxing gym, and arelentless drive to get to work
pulled it from addiction andpropelled him into tech
innovation. In this episode, Kendrops gold for anyone feeling
stuck, overwhelmed, or ready tofinally make the leap into
solopreneurship. If you've everdoubted your next move, this
(00:25):
episode will light a fire.You're listening to the Aspiring
Solopreneur, the podcast forthose just taking the bold step
or even just thinking abouttaking that step into the world
of solo entrepreneurship.
My name is Carly Ries, and mycohost Joe Rando and I are your
guides to navigating this crazybut awesome journey as a company
(00:46):
of one. We take pride in beingpart of LifeStarr, a digital hub
dedicated to all aspects ofsolopreneurship that has
empowered and educated countlesssolopreneurs looking to build a
business that resonates withtheir life's ambitions. We help
people work to live, not live towork. And if you're looking for
a get rich quick scheme, this isnot the show for you. So if
(01:07):
you're eager to gain valuableinsights from industry experts
on running a business the rightway the first time around or
want to learn from the misstepsof solopreneurs who've paved the
way before you, then stickaround.
We've got your back becauseflying solo in business doesn't
mean you're alone. Ken, it's sofunny because we've been talking
offline for the past fewminutes, and I feel like we
(01:28):
should have pressed recordbefore we actually hit record
because I have just already soenjoyed chatting with you. You
are just a ray of sunshine. Youhave the best shirt on that
reflects that as well. And we'rejust so thrilled to have you on
the show.
Thank you for coming today.
Ken Cox (01:42):
Thank you for having me, Carly. I appreciate it. You
too, Joe.
Carly Ries (01:45):
Yeah. And I wanna just dive right in because I'm
so intrigued by your story. Youhave a journey from addiction
recovery to tech innovation. AndI think it's just incredible. So
are you able to share that storyand discuss kinda what mindset
shifts helped you go frombasically rock bottom to running
multiple businesses?
Ken Cox (02:04):
Yeah. So I've always run multiple businesses. And
quite honestly I used drugs andalcohol as a crutch to help me
for a very very long time. AndI've had to do a whole
transition to learn how to sella completely different way. Like
do business a completelydifferent way because before you
know I could turn happy hoursinto business on a regular
(02:26):
basis, right?
And I realized that that waswell, my doctors, the judges, my
wife, they all realized that Ihad a problem way before I ever
did. And I had to overcome that.but back about ten years ago I
was diagnosed with liverdisease, alcohol related liver
(02:48):
disease. And the doctor saidquit drinking or you've got
about two years. And so I had tofind a process to do that and
quite honestly I was really,really mad about it for a long
time. And struggled to quit fora very long time until I had a
couple of epiphanies.
But those epiphanies camebecause the first thing that I
(03:08):
did when I decided to quitdrinking, take it seriously, was
I found a boxing gym and Istarted going there regularly.
Being in business my entire lifeand running small businesses and
large businesses, it became veryobvious to me that this business
was not going to last very long.So I reached out to the owner,
I'm like, hey, you need to letme buy this gym so it stays here
because if I don't have the gymthat I like, then I'm gonna die.
(03:32):
So I bought that gym from him.Grew that business on the side
while I was still running RiverCity and very very challenging
time for the company as a wholeand for myself at the same time.
I just lost my predecessor, mymentor Steve, and I was going
through all this other medicalissues that I had. But through
(03:55):
this journey, we started a youthboxing team and I became a youth
boxing coach. And one thing thatthe trigger moment for me is
when I realized that I had totreat coming out of addiction
like like I was coaching myselfto change my mindset of who I
was and change who I identifiedwith. And that was the entire,
(04:17):
the crux of the book ReclaimSobriety was changing who you
identify as is a huge step inany direction you wanna go. So
if you wanna quit drinking,wanna become an entrepreneur,
you wanna do any of thosethings, start identifying as
what you wanna be and do thethings that that person would
do, and that's what you willbecome.
Carly Ries (04:37):
That is wild. So you said you could turn any happy
hour, any night out into abusiness meeting. What do you do
instead now for your businessmeetings, and how do you keep
those relationships going in anew environment?
Ken Cox (04:51):
Well, lot more challenging today for business
as a whole, I think. Not only,you know, can I not go to the
bar and meet new clients and dothe happy hours and do the
networking and be the life ofthe party, right? I can still
try to be the life of the party,right? I can wear a fancy shirt,
I can put on a smile and I canshake hands and meet people. But
(05:13):
you know, I did a lot ofinternational business prior to
not drinking.
And I just don't do that kind ofbusiness any longer.
I transitioned. I like to do alot of business with small and
medium sized businesses, owneroperator businesses, and
implement services that have areally great value for that
(05:34):
company at a really affordableprice. And I think that that has
been the part of the turningstone for me of transitioning to
the type of sales that I didbefore, to the type of sales
that I'm doing now. It's abigger grind, and you know I'm
not swinging for the fencesnearly as much as I used to.
But that also might be age.
Carly Ries (05:57):
There you go. Well, Ken, what I find so fascinating
about you is you keep saying,oh, I've been running all these
businesses. I used to dointernational businesses and all
this, and it sounds like youhave a gazillion businesses. So
you're an entrepreneur, you havethe entrepreneurial spirit, and
you call yourself unemployable.And I'm curious what that means.
And at what point in your careeryou went from corporate and
(06:20):
decided not only am I goingsolo, but I'm never gonna be
employed again.
Ken Cox (06:26):
It was a long journey. I started my first company at
the age of 14 doing vendingmachines. I sold my first
company, video productioncompany at the age of 19 and I
went to work for them. When Iwas going through school and I'm
super fortunate and a derelictin so many ways, right? My mom
(06:48):
was working at WashingtonUniversity so I got free
tuition. I graduated frombroadcast center and then I
transferred to WashingtonUniversity, which is an amazing
Ivy League school. Ended updropping out of there and
transferring to Webster. While Iwas at WashU, was working there.
That was my last kind of bigcorporate job where I was not a
piece of the company, right?From there I went and I traveled
(07:12):
the country with musicians,being stage manager.
In 1999 I started, I left theentertainment industry, film and
video, and I went into IT.Specifically, for a couple days
I was doing DSL sales. If youremember DSLs in '99, we were
(07:33):
the first to market. Fastestgrowing company in the country.
I was just an employee at thetime.
And I took the job until I gotmy next entertainment gig. That
was literally it. I didn't wantto go to Japan with the tour
that I was on. So I told my bossI guess, to find me another tour
that's in The United States.During that process, I got a
(07:54):
chance to move into the webhosting world.
Because I went to WashU, I knewHTML in '99, I knew FTP, I knew
all these things. And I can tellyou a quick little story if you
like to hear it on how thetransition went and where I fell
in love with web hosting. I'msitting in an office taking
calls selling DSL right. It'sbasically order taking. Somebody
(08:17):
walks in the office and like whoknows how to FTP and I raise my
hand.
And at the time if you canimagine you know, my hair was
maybe two or three inches longand spiky and was probably
yellow or purple or some crazycolor. And I raised my hand
like, oh I know how to do that.And like, follow me. So we
walked down the hall and aswe're walking down the hall more
(08:37):
suits show up and they'rewalking with us and we get to
this other office and they'relike, okay, we need these files
up on this server. So like, noproblem.
And at the time it was aMacintosh. So I downloaded Fetch
and transferred the files. Like,not a big deal at all in my
head. And that website wasMasterCard.com.
But I was uploading. And mymentor, I didn't know him at the
(09:02):
time but he became my mentorvery quickly, looked at me and
he says you now are in the webhosting department. And now I
get huge clients. Like the veryfirst client I used was
MasterCard. And I had WonderBread was my very next big
client.
So working on Twinkies.com andfound myself in the lawsuit. If
you wanna Google theTwinkies.org lawsuit. It was a
(09:26):
big debacle for a very longtime. And I fell in love with
that world. And I startedhelping small businesses and big
businesses build the websitesand help with their operations.
And it was crazy chaotic. But byFebruary the world was changing
drastically really reallyquickly. Got super rich with
(09:46):
stocks and then super poorinstantly because the stock
market crashed. Right? And I gotin some trouble with the IRS.
So I picked up a job bartendingat night while I was doing all
this other stuff to try to payoff some debt. And one day my
predecessor Steve, the guy thatbrought me into the web hosting
department walks into the barthat I was working at and says,
hey we're starting a web hostingcompany. I said I'm in. I'm like
(10:10):
what do you need?
And so we started the webhosting company and that's where
I learned internationalbusiness. Because I couldn't get
customers in The United Statesbecause of my non compete that I
currently had with the companythat I was working for. So
started writing articles,sending them out all over the
world. Very first customer wegot was a company called IU
(10:31):
Kuwait. It was like a KuwaitiNapster. And it was really cool
and I just fell in love withthat kind of dodge and weave.
The company that I was workingfor at the time was going under.
And we had the opportunity tobuy all the web hosting
customers that the company thatI worked for was hosting. And we
(10:55):
raised the money and executedthat and that was kind of the
birth of Posturion for you know,we started and within six months
we were over a million revenuewith that one acquisition.
Joe Rando (11:07):
And what year was that? When was that?
Ken Cox (11:10):
That was, we started Hosteering in February, mid '2
thousand.
Joe Rando (11:14):
So post crash but not much post crash.
Ken Cox (11:18):
Correct. Post the VC crash but the services still
needed to be served, right? Sothey weren't fake services but
they were definitely acquired.The customer acquisition cost
was outstanding and theoperational cost was
outstanding.
I've always been really goodwith operations and I've been
able to cut through a lot ofthis crap really quickly.
(11:39):
Growing up as a dyslexic kid,always on a keyboard because
that's how I got to turn myhomework in. Loved technology so
I knew Linux just kind oforganically. I knew how to
manage through Linux and work oncomputers. So I was a natural
fit to run the operations forthe company.
Carly Ries (11:57):
So the thing that I'm also getting from this is
you had a lot of experiencebefore you flew solo. And for
people that are wanting tobecome solopreneurs and they're
listening, but they haven'tquite make the jump, look at
everything you're doing rightnow as education for when you
actually jump intosolopreneurship. It sounds like
you had some incredibleexperiences that really set you
(12:21):
up. So people that are kindagetting antsy and aren't quite
making that leap, I guess, wouldyou agree like your turn will
come, but just look ateverything you're doing right
now as a building block to makethat leap?
Ken Cox (12:33):
Yeah. I mean you know we all have these ideas of how
we want it to unfold. And it'snot gonna unfold that way. So
you know, just start moving,start setting things up, And
then look for the opportunities.Constantly looking for
opportunities that you canexecute on.
And you'll find opportunitiesthat you can't, that you're not
(12:53):
gonna be able to execute on forone of a thousand different
reasons. Generally finance oroperations capability, right?
Those are the two kind of bighurdles in the world. But I mean
both of those hurdles aregetting way smaller by the
minute with AI and technology.Like those hurdles to get
started are really getting low.
(13:15):
And I've always told people,look at your current job to see
if you can buy pieces of therevenue. Or buy some revenue
right out of the gate to kind ofget yourself stable and sturdy.
That works really great forservice based business. You know
other solopreneurs, common likecoaches and physical fitness
people, they gotta build theirown infrastructure and their own
(13:39):
client base. It's much harder tobuy that book.
Joe Rando (13:42):
You know, one of the things of your story that I
think is really, reallyimportant is the the FTP, which
stands for file transferprotocol. So you're basically
sending files from a computer upto the Internet, if you will. In
those days, it wasn't the cloud,but and to you, you were like,
this is easy. And yet there werea whole bunch of people in the
room that were, thinking youwere working magic. And I think
(14:05):
that's somethingsolopreneurs need to think about
is the fact that things that areeasy to you, that are obvious to
you, that you clearly think arejust, you know, nothing can be
really powerful for somebodythat doesn't know what you know.
Ken Cox (14:19):
Absolutely. And knowing how to do something that
somebody else doesn't know howto do is always a very valuable
valuable asset. Now AI is hereand anybody can know how to do
almost anything within a coupleof mouse clicks and a couple of
phrases they type in. But beingable to execute on that is what
it's all about
Carly Ries (14:41):
Yeah. Absolutely. Well, being able to execute,
you're talking about like justtaking everything and just doing
it. So suffice to say, let's getto work.
Is that your mantra? have youhad that mantra forever? Did
that start with the gym when youpurchased it? Where did that
come from and how can you applyit to solopreneurs who are kind
(15:04):
of stuck overthinking instead ofjust doing it?
Ken Cox (15:08):
So I'll tell you the story where get to work comes
from. my lawyer is an older man.I'm gonna say late seventies,
early eighties. And he loves totalk because he loves to run up
the bill. And every single timehe'd call me, we would sit and
we'd have these conversationsand he loves boxing and he's
(15:33):
a pretty high up there attorney.
We would talk for a while andI've learned so much from this
man. But at the end of everyconversation he'd say, alright
Ken get back to work. And I'mlike okay. And it was so funny
that every time I got off thephone with him I realized man
(15:53):
I'm really productive for aboutforty five minutes because
somebody just said okay can getback to work. And I would just
do it.
And I'm like man that's prettypowerful. So how can I make that
my own and just get to work? Andwhat I realized is that just
saying simple phrases to peoplehelps them, helps me do, take
that action. Right? So get towork became my hashtag.
Carly Ries (16:16):
Want that so much. And I think it's so funny,
you're right. It's a quicksentence but can be so
motivational for people that arejust kinda stuck in a rut.
Ken Cox (16:24):
Yes.
Carly Ries (16:25):
So Ken, my other question is that you say that
anything can be a businessbasically. So I'm curious, what
is the wildest or mostunconventional idea you've seen
someone turn into a profitablebusiness?
Ken Cox (16:41):
I have a friend that that started Hempster. And he
did this is pre THC being legalin most countries or most states
in the country. And he was a bigfan and he started just making
these little boxes and andputting different items in
there, and then shipping themout. Now where it becomes
(17:03):
brilliant is he was trying tofigure out how to make that more
profitable. And so he found out,Are you familiar with rolling
papers?
Mhmm. And he realized that mostrolling papers in the world were
made by slave labor. And flewoverseas and did a whole lot of
(17:25):
research. Ended up creating hisown rolling paper manufacturing
company. And removed all thesepeople from basically slave
labor.
Started paying them good wagesand now was one of the largest
rolling paper manufacturers inthe world. This is over the last
ten years right? Sounconventional as you look at an
(17:46):
industry like that you think manthere's no way I could get into
that at all. But you know hecreated a really good customer
base that would use that productprior to starting the
manufacturing.
And then started themanufacturing and kept going.
Some of the other businessesthat I really love today, and I
think that this is really moreimportant than anything right
(18:08):
now, are the service basedbusinesses in local communities.
I think they're so important.The dog waste pickup companies,
the trash removal companies, thepower washing companies. All of
these businesses forsolopreneurs that they can get
started with very low overhead,provide a very valuable service
(18:31):
in their community, hireanywhere between two and twenty
different employees to kind ofexecute on all these different
jobs to do.
And the beautiful thing now isthat the tech is here to support
them at a price that is wildlyaffordable. You know so it's no
longer that they gotta do stuffon spreadsheets and just quick
book invoices. They can have alot of automations and things
(18:51):
like that today. And just have areally really cool life. And I
love what the kids are doingwith art today.
Like making creative stuff andselling it. The spin art with
different team logos on it andstuff like that, think is so
creative and fun that I thinkyou know, it's a beautiful world
(19:13):
for the future. And podcastingis probably one of the biggest
that's happened over the pastfive or ten years that I think
the maturity of podcasting isgetting so much better that
people are able to start apodcast and make a make a living
off of a podcast with just acouple people.
Carly Ries (19:34):
Yeah. It's wild. I agree. You can really turn
anything you're passionate aboutinto business if you really
think through it.
But one thing I wanted to pickyour brain about is you said
you're really good withoperations and kind of building
systems and everything. So I'mcurious about this ten day to
change everything strategy thatyou have. what is that exactly
and how can you apply it tosolopreneurs?
Ken Cox (19:56):
So ten days to change everything. We're getting ready
to launch and I think it's gonnabe out before this episode comes
out. What we did, and it'schanged quite a bit while we're
building it, is we have 10custom GPTs created that were
given with the program and we'reteaching people how to use those
(20:17):
GPTs. They're chat GPTs butthey're custom GPTs starting
with business foundation. How towrite my business plan.
How to write my marketing plan.How to write my brand kit,
right? And a GPT that's designedfor those functionalities.
There's another GPT that's allabout legal business stuff. How
do I get my LLC form?
(20:38):
Should I do LLC or S Corp? Youknow all of those questions. And
we just walked through ten daysof, I'm assuming that a lot of
solopreneurs and businessoperators have been through at
least one or two differentcourses on how to start a
company, right? And they're all,and I've been through hundreds,
(21:00):
they're all about the same,right? There's a process that
you go through.
So we created ten days that helpyou use AI to create all of
those processes for you.
Carly Ries (21:10):
Oh wow. And that's yeah. For solopreneurs, that's
invaluable. And this isn't yourfirst rodeo with technology. You
I mean, obviously you were justtalking about it, but InLink is
also one of your businesses.
Ken Cox (21:21):
Yes.
Joe Rando (21:21):
It's filled with a plethora of tools.
Carly Ries (21:24):
So in your opinion, AI aside, what is one tool you
think solopreneurs should havestarted using yesterday that
they may not be using today?
Ken Cox (21:34):
Without AI?
Carly Ries (21:36):
Well I guess you can use AI. Don't use Chat GPT.
Ken Cox (21:38):
AI employees I think are, what we're telling most
businesses right now especiallythe solopreneur, main street
America, brick and mortarcompanies. If you have a front
desk role today, somebodyanswering the phone, sending
emails, sending text messagesand I'm gonna use the
eightytwenty rule but it'sreally probably like 99/1 . 99%
(22:01):
of those phone calls, textmessages and emails are the same
answer. Here's the form tocancel. Here's the form to put
you on hold.
Here's the form to get booked toyour next appointment. Right?
All of those things and AI doesa wonderful job today of picking
up the phone and answering allthose questions. Sending them
text messages. Answering youremails, sending them back.
(22:24):
So InLink's big movement isteaching people how to create AI
employees, but also in a mannerwhere they understand that those
AI employees still need to bemanaged, right? So this is the
staff that we believe should bereplaced by your transient
staff. Your college kids thatare coming home for the summer
(22:47):
And not saying you shouldn'thire them, but you should hire
them to manage your AI employeesand oversee them and spot check
those calls and spot check thoseGoogle reviews that they're
answering and spot check theemails that responding to.
Because like any employee, an AIemployee can get off the scope.
(23:08):
Specifically if they go off ascope and that off scope task
gets reinforced multiple times.
You know, you can have an AIthat thinks it's Spanish if it's
English speaking kind of thing.So it needs to be managed and
watched. But they work twentyfour hours a day, seven days a
week. They don't take vacationand the correcting their
(23:32):
behavior is a non emotionalevent.
Carly Ries (23:34):
Interesting. Yeah. Well, and just so that we're
clear on terminology, because alot of times in this show we
just say contractors becausethey're people that don't hire
employees. So like potato potatoin this Right. But just for
consistency purposes.
Ken Cox (23:48):
Yes. But we've all been on the phone with one client and
the phone's ringing and thatphone has, that call has to go
to voicemail. And today itdoesn't. It could be picked up
by an AI employee or we'reworking with a client, right?
The chiropractor or the HVACtech is you know literally
spinning wrenches servicingtheir client and the phone's
(24:10):
ringing.
I think the stats somewhere on60% of calls to small businesses
go unanswered. Right? And everyone of those unanswered calls is
a potentially missedopportunity. And then not even
the extra added benefit is thatyou never have to answer a spam
call again. Yeah.
Because your AI employee's gonnajust get rid of that really
(24:30):
quickly.
Carly Ries (24:31):
It's so weird just living in the wild wild west.
I mean, ChatGPT, I meanmainstream usage of it just came
out just over a year ago. Right?I was trying to think of when
people really started using it.
Ken Cox (24:48):
when GPT three five came out, I instantly knew that
it was different. And I signedup MIT has a really nice
program. It's a I think it'ssixteen weeks and it's AI for
business. And it's not even anhour after GPT 3.5 was
introduced to me was I signed upfor that course and went through
(25:11):
it. AI is changing, going tochange everything that we do.
AI, coupled with robotics, youknow, don't think the world even
understands where we're gonna bewith robotics in five years.
Joe Rando (25:26):
Have you seen the newest bots in Dynamics humanoid
robots?
Ken Cox (25:30):
Yeah. It's crazy. I have now robots that are mowing
my lawn and snow plowing mylots.
Carly Ries (25:38):
Are you serious?
Ken Cox (25:39):
Absolutely.
Already. And they're doing aphenomenal job. The robotics
coupled with AI is a juggernautof performance that is so
profound that the world's goingto change. I'm not sure exactly
(26:01):
where we're gonna end up in thiswhole world. I know that you
know the laborers and the unionsare really trying to hold on to
where they're at.
But humans are gonna lose thisbattle for labor. Robots and AI
are gonna take it.
Carly Ries (26:17):
You guys, I think I need a nap. My brain just
exploded. Oy. Well, we could godown this rabbit hole all day
and have not only an entireepisode on it, an entire new
podcast to talk about it? Andthe robots can do the podcast
for us.
Ken Cox (26:33):
And they are.
Carly Ries (26:35):
I know.
Ken Cox (26:37):
Like, you're probably following somebody on TikTok
that doesn't exist.
Carly Ries (26:42):
I know. You guys, I have a confession. I am also a
robot. So we've been interactingwith AI this entire
conversation.
Ken Cox (26:51):
How would we know?
Carly Ries (26:52):
Exactly. You wouldn't Ken, this has been such
a treat. You're a joy to talkto. We ask all of our guests
this question. What is yourfavorite quote about success?
Ken Cox (27:02):
Don't let yesterday take up too much of today. And
that's Will Rogers.
Carly Ries (27:07):
Oh. I like it. Very cool.
Joe Rando (27:11):
We haven't had that one yet.
Carly Ries (27:12):
Yeah. It is.
Ken Cox (27:13):
Cool. But Will Rogers is pretty old. Yeah.
Carly Ries (27:19):
Well Ken, you have so much going on. Where can
people find you if you wannalearn more as well as learn more
about the ten day challenge?
Ken Cox (27:27):
Yeah. You wanna know more about the ten day challenge
or join our AI workshop onTuesdays, just go to Inlink.com.
That's inlink.com. You wannaknow more about me and my
shenanigans just KenCox.com
Joe Rando (27:40):
And a question, did I hear something about a book?
Ken Cox (27:43):
Reclaim Sobriety is my book. Super proud of it. It's
one of the things that I'm mostproud of in my existence today.
It's been adopted.
We got it. It's in every libraryin The United Kingdom's prison
system. As a mindset shiftinghelper or assistant. So, yeah.
(28:05):
It's a ton of fun.
That's awesome.
Carly Ries (28:08):
So check that out too. Well, Ken, thank you so
much for coming on the showtoday. Listeners, thank you so
much for tuning in today. Asalways, please leave that five
star review. We would love it ifyou would subscribe on your
favorite podcast platform, andplease share this episode with a
friend.
A lot of people need to behearing this information or be
terrified of AI and roboticsthat are coming our way our way.
(28:29):
But we will see you next time onthe Aspiring Solopreneur. And,
Ken, let's get to work. You maybe going solo in business, but
that doesn't mean you're alone.In fact, millions of people are
in your shoes, running a oneperson business and figuring it
out as they go.
So why not connect with them andlearn from each other's
successes and failures? AtLifeStarr, we're creating a one
(28:51):
person business community whereyou can go to meet and get
advice from other solopreneurs.Be sure to join in on the
conversations atcommunity.lifestarr.com.
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