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Mark explores the minds of visionary entrepreneurs who refuse to limit themselves to a single venture to learn how these trailblazers manage risks, innovate across industries, and turn ideas into impact.
Whether you’re scaling your first business or juggling several, this podcast is your ultimate guide to thriving as a parallel entrepreneur.
speed to market is critical
we we know that every single day
whether you're bootstrapping or whether um
you're that AI company
trying to beat someone to the market
to be able to establish you know
brand dominance you gotta get there fast right
so we're all racing very quickly
welcome to the Parallel Entrepreneur
this is a special series on innovation
supported by Relationalary
Marketing and the Chase Studios
recorded at the Greater Nashville Technology Council
Innovation Summit
I'm joined today by guest host Johnny Anderson
he's the entrepreneur in residence
at the Nashville Entrepreneur Center
sit back and join us for this special edition of
Having Authentic Conversations with People That Care
building a strong
entrepreneurial city doesn't happen by accident
it requires systems that actually work
Dakota Simpson is the Chief Program Officer
at Nashville's Entrepreneur Center
where he leads five accelerators
supporting founders at every stage
his work sits at the intersection of entrepreneurship
economic development and community impact
Dakota is on a mission to nourish
entrepreneurial spirit in Nashville
what makes Dakota's perspective unique
is how he thinks beyond individual companies
he spent his career working in government
nonprofit and cross sector environments aligning people
programs and incentives so that people can flourish
in our conversation we explore
why entrepreneurial ecosystems
must be intentionally designed
not just enthusiastically supported
and how building the right systems
makes founder impact more sustainable
let's just dive right into this conversation
what does innovation mean
and then specifically what does it mean to national
I think everyone's answer to what does innovation mean
um varies because it's a very ambiguous term for for me
it's
it doesn't necessarily imply creating something new
I think it means doing something in a new way um
I'm I'm a big fan of economic development
and let's call it continuums of care
so I don't think we should ever innovate in a vacuum
so for me Nashville innovation
what that means is
are we connecting the dots across multiple
disparate organizations in a meaningful way
that drives impactful change in our city so
that's a lot of hoopla
so let's let's run with a tangible example right yeah
I'm not sure that's hoopla
what's a meaningful way to define that
yeah yeah yeah
so I think for instance
like let's let's run through a founder's uh continuum
so let's say um
we've got a founder that's interested in the healthcare
industry so they start a healthcare company
that reduces friction within the healthcare sector
we could say our jobs done
they've started that company
and they've got a business plan
it's vetted seems viable
we've connected with them with some advisors great
but then what right
they may need a chief technology officer
or they may need to uh
contract out with software developers
then we may introduce
them to the National Technology Council
to really kind of run with that continuum
and continue fostering that um
startup and then from there it shouldn't stop either
we should hand them off to the local
chamber of commerce and make sure they're getting
connected into the broader eco ecosystem
and making sure uh
they're landing clients and assisting HCA
and then who knows
it's almost like a feedback loop
it's innovating reducing friction in a meaningful way
that in the aggregate
is more impactful than the invention
or service that's been produced
it's a tangible
ripple effect across our entire community
so all these um
reflections of success and alignment
how how would you describe something that's frustrating
what's frustrating now
that's really interesting Mark
I don't know if I've been asked that lately
what is frustrating
I mean if you want me to be candid
it's it's frustrating trying to keep up with the uh
the energy we've seen but it's
it's frustrating in a good way
the the entrepreneurial energy we've seen post pandemic
the explosion of entrepreneurial rates
I mean it's through the roof and
and really what's incredible about the data
we were just looking at this last week is um
it's not went down so
you know what you would expect pre pandemic
or what I would have hypothesized is oh
a lot of people go remote
they may have excess time on their hands
they may um
become you know
unhappy with their employers
and they may launch their initiatives
okay that spikes up
everything goes back to normal and
you know then they return back to work
but guess what happened it didn't go back to normal
right we still have a lot of remote work
we still have a lot of people that are innovating
a lot of people still frustrated with their employers
and we know adversity births entrepreneurship
a lot of the time so
it's been fascinating to watch that
those entrepreneurial rates maintain
and at the National Entrepreneur Center
we graduated 118 founders last year
the year before that it was about 90
This year we're on track to graduate 200+ founders
like we're getting ready to double the impact
we have as an organization
and that's a credit to Sam Davidson
our leadership our board
and all these people that are working
hard behind the scenes but candidly
it's also a credit to you know
your everyday person that's deciding hey
I wanna take my future and put that in my own hands
and I'm gonna be brave
enough to go out there and launch a business
so what's frustrating me at the moment is
there's all of these amazing entrepreneurs
and there's so many incredible ways to serve them
but we're trying to balance like
you know breadth
but also depth of services
because we wanna serve them all
but we also wanna serve them all effectively
and that's something new for us
as we've seen this energy and explosion in the city
um I have a theory that uh
there's entrepreneurship
there are people that we recognize as serial
entrepreneurs one after another and
and I've been working on a thesis
and a research project and
and exploring the identity of a parallel
entrepreneurship experience
more than one company at the same time
and in that exploration I've noticed some trends
I'm curious
if you're seeing any trends here in Nashville
related to the average age of the entrepreneur
what's the demographic looking like
and how has that changed uh
in your experience and I'll share what my theory is
but I wanna hear what your experience is
this the do old guys have a chance question
I like that question do you and I have a chance
yeah no
I mean I
I would share well
first off Johnny
of course you've got a chance um yeah
no I
I would share that um
typically we we see we're serving um
founders of all ages um
and from all demographics
but I mean it's
it's true if
if you look at the trends and something we're seeing
especially as we talk about perspective
collaborations with um
Metro National Public Schools or Belmont University
Vanderbilt is um
the entrepreneurial um
participation by the younger generation
Gen Z specifically is through the roof
uh I believe it like last glance
one out of every two um
Gen Zers state that you know
they're interested in starting a company
and almost that many actually do in some form
now it's it's not companies like
you know um
i i say we might think that implies i'm i'm y'all's age
but just to be honest
i've got an old soul so maybe i can kind of relate
but you know
we're not talking about starting healthcare companies
we're talking about you know
we might be operating a TikTok or you know
we might be monetizing video games or you know
it may actually be some more hands on stuff
we see that and that's
providing those individuals with revenue and money
and and that is a business well
and I'm seeing it as micro SAS services sure
I'm seeing it as uh
AI problem solving for one specific thing
they really understand and it
they just set it and forget it and it runs off yeah
it's a subscription
I'm seeing people excited about simple things like a
simple like running a food truck sure
I mean but I my but my theory
I think it's being reinforced by this observation
I think the younger you are
the more likely you are to emerge into entrepreneurship
as a parallel entrepreneur
you've got one two
three four things going this whole side hustle culture
the the independent contractor perspective that
that a lot of people bring
and maybe
I'm not saying that starting a healthcare company
that's gonna become something
the next big anchor in town is
is not not possible I'm just observing this uh
more more explosive more creative
more deeply niche entrepreneur at a younger age
with technical skills um
really putting a some
some dynamite in in
uh in the entrepreneurial path
I think yeah
I mean and hey it
it makes a lot of sense
like if you really dive a little bit deeper right
is they they grew up in that environment that's
that's a skill that you know
we had to train ourselves on
but that was acquired by extension of
you know their
their environment right
so that's that's something that's kind of ingrained
in that population I mean
if you think about it I
I remember when um
growing up I was
I was raised by three incredible strong women
and one of them was my great aunt
I remember she had a Blackberry
iPhones didn't even exist right
so it's a whole different ballpark
whenever you've actually
grown up with those innovations
around you and you've been
Learned how to use them play with them
test them from a young age
but I'll I'll also share probably equally important
if not more important is um
the barrier to entry is way lower when you're younger
you know I started a company whenever I was 16 um
doing djing and event planning and running out venues
well guess what
it's a lot easier to do that
when you're not paying rent every month right
it's a lot easier to do that
when you have excess time on your hands because yeah
of course
you go to school and of course you've got homework
but you don't have all of the responsibilities of life
that come down the road so I think you see that
our job is to make sure we're
continuing to enforce that
and make sure the younger generation is aware that hey
there's a lot of adults that dream
and work hard every single day
to work for themselves
and to have that freedom and that flexibility
and you're at a unique point in time
where you can start that before all of these problems
not problems well
sometimes the problems it depends on the day yeah
I mean Nashville
Athens of the south
there's 120,000 college students in this town
that
I suppose it should be natural that there would be any
a real bloom in entrepreneurship at that at that level
entering the culture here in Nashville
and then choosing to stay sure yeah
and you know what's really interesting too
is just the entrepreneurship by acquisition
we can I don't want to interrupt Johnson
I want you to finish your thought
but like let's
let's go down that rabbit trail
because we're seeing that trend as well
quite a lot
well I think this is first conversation I've been in
in weeks that AI didn't come up in the first like
you know 3 questions but um
it's a good segue specific to entrepreneurs
what do you think AI's impact
and this is gonna be a big question
but what do you think the impact's gonna be
or what are you seeing some of the impacts right now
yeah I
I really go back and forth on AI
just to be candid with you Johnny
because
alright so let's start with the obvious
AI has caused an immense explosion
and entrepreneurship across the nation
um but to your point Mark
a lot of that entrepreneurship is
you know we
we call it AI rappers right
these individuals are able to kind of vibe code
if you will and create a
B to B or B to C subscription
that really
a lot of consumers could probably get
if they interacted with chat
GPT in a meaningful way it's just easier for them
because the friction's been reduced right
and it's already been built
so I go back and forth
because we've seen an explosion of businesses
and an explosion of energy around AI
which is fantastic but also it makes me question how
how sustainable is that as ai continues to mature
um and develop
like i've heard theories i'd
i'd love to hear y'all's thoughts on b to b sass is
you know soon to be extinct
cause why do you even need a software
if we eventually get to an AI
platform that is able to do all of that for you
so think about Tableau for instance
data visualization platform
do you really need that platform
to input all of your data
and manipulate it into visualizations
if you have a chat GPT bot or an AI
bot that you're able to interact with
and then it spits the visualization out to you right
you've actually circumvented the need
for the enterprise platform altogether
at that point so yeah
it's a mixed bag for me
Johnny and it's something we're still um
observing at a high level
what I share with my friends
whenever they ask me this question is
I think in the long term
AI is just like your iPhone it's not gonna replace you
but it's a tool that you better become familiar with
and you better learn to use
because it's gonna be with us for quite some time yeah
people deserve to have better tools
sure and
everything that we talk about
from a technology perspective is just a tool
I think wouldn't it be cool
if we could just talk to the computer
and spit out an app which I just spent 9 years building
a company that built apps
you know wouldn't it be cool if you could vibe
code your way into rapid innovation
and I I think it's the speed of innovation that is um
breathtaking right now yeah
you there the barriers you called you said earlier
the barriers to entry are lower
knowledge is no longer a barrier to entry
sure for almost everything um
but I think knowing what kind of problems
what kind of questions to ask
and what kind of problems to address
are probably where the solution meets
financial success and
and really serves a lot more people faster
I'm I'm
but speak about speed
talk about how fast this is happening to
to in your observations to Nashville
with Nashville how fast is things going
oh it's yeah
um very fast
I mean
just to speak once again about kind of the volume
um of individuals we're serving
we're we're seeing those numbers go high
I mean double right
um and I know we're not the only organization
experiencing that with the same staff yeah
yeah with the
with the same staff um
but you know
we we roll up our sleeves and we work hard
because we understand that the impact
while fulfilling on the individual level
getting to work with individual startups is meaningful
the impact is way larger than that
I mean when we work with one startup
we know small businesses drive um
the economy right
so we're talking about ripple effects
throughout the entire region
so we're small and mighty
but we're also determined um
to make sure we we make an impact
but yeah the
the speed is incredible um
Mark
in terms of the amount of founders that are innovating
in terms of um
the innovation how bold their ideas are and how
how much
it just makes sense whenever you encounter these ideas
and the amount of friction we're seeing
reduced in our lives so
but that's good right
need the market is critical we
we know that every single day
whether you're bootstrapping or whether um
you're that AI company
trying to beat someone to the market
to be able to establish you know
brand dominance you gotta get there fast right
so we're all racing very quickly
and yeah
I think I've run out of breath just talking about it
I mean it's pretty
it's exhausting but it's in a good way right
and I think that that's the challenge is like
how do you keep up with the speed
as an entrepreneurial support organization
as a founder trying to inventory all of these resources
as a consumer you know I um
I love leveraging AI but it's like
I find one AI chatbot
and it feels like there's another one that's superior
tomorrow than the next day
than the next day
and kind of wears you down a little bit
haha you know
on AI I find I just tell myself
just dig into one
become as comfortable an expert with one
I've heard a lot of people move from oh
this one shiny object and then this one
it does a little something better
and I got some friends who are pretty sharp at this
and they they set up
playgrounds and sandboxes for the different AI
tools to interact with one another
and some CEOs that I know
are spending an extraordinary amount of time in AI
like maybe more time in AI than and
and in product planning
and in sort of just really defining the direction
of the company than I've
than I've experienced in the past
because they're tech oriented and they're smart people
um but they're digging in really deeply
uh
and then I hear an occasional
story about somebody who lost their job recently
and has been looking around
and has spent the last 6 months pouring into AI
and their level of excitement
they don't feel unemployed
they feel like they're about ready to take on the world
so it's like an empowering thing
it's a deep dive thing
and it's also like it's an experience
it's a living experience
it's just one of the most exciting
things that's happening in our culture right now
I think well
in some of our conversations we've
we've we talk AI
we go straight to the technology
and the technology companies
but at the Entrepreneur Center
we've watched a pasta sauce lady
yeah that has leveraged AI to get her faster to market
to get remove some of those friction points
that an entrepreneur might spend
four weeks and 10
15 $20,000 on
getting their statement of work together
or their contract components
or their terms and conditions
and in a lot of ways we we often forget that
there's a lady out there making pasta sauce
and the faster she can get that pasta on the shelves
the better let's not forget those
the world still needs ball bearings
sure and I
I'm I get as excited about that component as I do the
technology itself and Mark
I think it's to your point
it's a tool for people
let's not forget that it's not the thing unto itself
it's it's a tool for people and it
it's a tool that opens up a lot of opportunities
I mean to to your point about um
Gina right there there's another um
entrepreneur that that we've served a Jason Reeves
who came in with a photography company
but he left with an AI company
yeah so I mean
he he from
he leveraged AI in unique ways that really helped his
service based business and before you know it
he's sharing that thought leadership with
individuals that were members of his cohort
and he realizes hey
there's an opportunity here
maybe I should be instructing people on how to use AI
to really
assist their small and medium sized businesses
now that's predominantly his main gig
so opportunity there you just discovered
you just like lifted up the covers
on a topic about listening
um he in this example saw an opportunity
he's listening participating in a market and listening
what are some of the things that you'd like to see
people listen to more hmm
I think broadly I would say
I would like to see people not only listen to
but validate others ideas a little bit more
and then I'll I'll get a little bit more of a specific
answer for you Mark
but what I'm saying is we see time and time again
regardless of AI
this is pre AI and this is now even with AI
the No. 1 reason startups fail are product market fit
time and time again
they experience a problem of their own and they think
oh I'm gonna solve this issue
and everyone's got this issue
so now we can move forward
often times that's not the case
and then they struggle to find a market
yeah so
you know just listening to others more broadly
like I think Jason did a fantastic job of that
it wasn't enough to say hey
I'm struggling with this in my service based industry
it's hey
let me actually talk to other founders
and better understand
if they're struggling with the same concepts
or there's other areas I can encounter right
and he kind of took that and really ran with it
utilizing AI so I mean
I don't know selfishly
I'm a I'm a community and economic development guy
like if you look at my resume
that's what I've done my whole life
I wish people would look at more um
more micro economic um
issue so on a city wide level
and lean into that with innovation
um I'm excited about the recent boring announcement
like I think that that's an innovative way to get US
transportation transporting individuals
but that's not enough right
and I think affordable housing
like all of these like buzz topics
but they're
they're main topics for a reason because people
are experiencing them every day
and like I I watch and I encounter it in our community
I'd love to see people listen to those problems more
and actually step up and demonstrate ownership
and truly innovate
and drive some more meaningful outcome
hey
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