Parallel Entrepreneur with Mark Cleveland

Why do AI initiatives often stall? What does it take to build AI strategies that scale inside real businesses? What does responsible, human-centered AI look like in practice?

In this episode of The Parallel Entrepreneur – Innovation Series, Mark Cleveland sits down with Jon Hilton, Shareholder-in-Charge of the LBMC AI Practice, to address these questions.

Jon brings a rare mix of experience, enterprise data science, large-scale digital transformation, and leadership forged through military service. From this conversation with John, you'll learn:

- Where AI strategy usually breaks down
- How to move from pilots to production without chaos
- Why clarity beats complexity every time
- The leadership mindset required to scale AI responsibly
- This conversation is for executives, founders, and operators who want results, not hype.

CHAPTERS:
 00:00:00 AI Isn’t a Technology Problem — It’s a Leadership Problem
 00:00:40 Introducing Jon Hilton: Leading AI Practice at LBMC
 00:01:47 The Strategy Disconnect: Executives vs. Employees
 00:02:40 West Point + Combat Tours: Leading Through Fear, Chaos & Uncertainty
 00:03:55 Building the Veterans Tech Peer Group in Nashville
 00:04:57 Military Technology + Nashville: What’s Being Built and Why It Matters
 00:06:27 The AI Tool Explosion: Don’t Chase Tools — Define the Problem
 00:08:25 AI’s Expanding Attack Surface: Scams, Security & New Risks
 00:09:42 “In Absence of Orders, Attack”: Courage and Forward Motion in AI
 00:10:24 Avoiding Paralysis: Deliberate Action Without Rushing
 00:12:03 Bringing People Along: Sentiment, Trust & Internal Buy-In
 00:12:55 Leveraging Veterans Well: What Corporate Leaders Need to Understand
 00:13:31 Translating Military Experience to Corporate Value (Network + Skills)
 00:15:10 Closing Thanks & Service Appreciation


ABOUT OUR GUEST
Jon Hilton helps organizations turn AI from an experiment into a scalable capability. As Shareholder-in-Charge of LBMC’s AI Practice, he works with leadership teams to define practical AI strategies, identify where automation and intelligence actually create value, and build systems that can scale responsibly across the organization. A data scientist by training with experience at ExxonMobil and EY, Jon brings a disciplined, execution-first perspective shaped by enterprise environments and military leadership. His work focuses on helping leaders make better decisions about when to use AI, where to apply it, and how to do so without creating risk, chaos, or wasted investment.
https://www.linkedin.com/in/jonathan-hilton/

ABOUT THE HOSTS
Mark A. Cleveland — Managing Director at Kensington Park Capital, entrepreneur, M&A advisor, and host of the Parallel Entrepreneur Network.
https://www.linkedin.com/in/macleveland/

Johnny Anderson — Nashville tech leader, GNTC board member, Entrepreneur-in-Residence at the EC, and host of The Impodsters™.
https://www.linkedin.com/in/johnnyonbrand/

👉 Join the Parallel Entrepreneur Network: https://www.parallelentrepreneur.com/#about-me
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What is Parallel Entrepreneur with Mark Cleveland?

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.

AI is not a technology problem

it fundamentally is a leadership problem.

Some conversations around AI are loud

this episode features Jon Hilton

who is super grounded on the topic.

Jon leads the AI practice at LBMC

and spends his time helping organizations

turn ambition into execution.

He's a data scientist a former EY and Exxonmobil leader

and a West Point graduate.

Who served two combat tours and earned the Bronze Star.

What I appreciate about Jon

is how he brings structure to the chaos.

He spent time talking about two things with me

that really matter number 1

why most AI efforts fail and 2

what it actually takes to build AI

that scales responsibly inside complex organizations.

This is a conversation for leaders who want progress

not hype so let's dive right in.

We've been talking a lot about AI leadership

really the thesis is right now

AI is not a technology problem

it fundamentally is a leadership problem.

And some some recent

statistics are really starting to back that up,

a recent survey found that you know

75% of C suite executives said their AI

adoption has been going well over the past 12 months

or been successful.

And 45% of their people say the same thing

and then 89 or 80 some plot plus percent of

C suite executives are saying they have a clear AI

strategy, and 57% of their people say the same thing.

So something's wrong here

and we are not going to get

companies and organizations

are not gonna get where they wanna go on AI

if they don't start figuring this out and it's really

really a misalignment.

So that's that's a big leadership you know problem

just trying to talk about how do you really solve that.

I love that and this is a leading question

but I'm gonna do it on purpose

what are some

maybe unique life experiences that you've had

that you can bring to the table

analogies that you can use?

Yeah that's and that's part of it

and I know you gentlemen know me

and some of my background.

But you know I'm

I'm a West Point graduate did two combat tours in Iraq,

and then you know

got out and got into corporate leadership. And

a lot of what I've started to see is

there's a lot of analogies of where we are

as a society and an organization with AI,

as you find yourself in a combat situation

and it's not to be macabre or dark

it's just what are the key things that you face

when you're about to go on a mission.

Or you're in those kind of environments

you you face a lot of fear

uncertainty and chaos at any time,

something that's well planned

could go completely sideways.

You have an unknown of what's out there at all times

and and you have to be the one to start

to dictate the situation,

requires a lot of planning and preparation and

and being a leader is

is one of the fundamental aspects.

And so that's part of what I've started to say is hey

there's some things here I've learned and

you know

that's the nature of even being in corporations

of what you're gonna face as you

you take on any initiative.

And so it's really starting to think about

how do I use my leadership principles here

if we know it's a leadership issue

not a technology issue you know

what are some of the things that we can really apply

to help move our organizations forward

with AI in a meaningful way.

In general

tell us something you're working on right now to

to make that impact

what are you being intentional about when it comes to

leveraging veterans to solve some of these problems?

Yeah that's a great question,

that's what we're really you know

here trying to start up again as

the Greater Nashville Tech Council's

peer group for veterans. Had a great showing there

in the pre covid era

you know like many things

covid tend to to sap some energy

and so we're trying to launch

relaunch that and

really start first and foremost with

can we build a community for veterans

as technology professionals.

Well you've

you've got a target rich environment here

as they say in the military right

we've got a Clarksville just up the street.

A lot of the focus of educating leaders in a combat

or a military environment relies on technology

and I think maybe the competitive

relative effectiveness of any armed force

is going to be tied to its technology

and its use,

use and deployment in service of the mission.

So you know how

how does military technology in the Greater Nashville

region

how has Nashville done in the producing

and creating and graduating of

of technologies that wound up having a military use,

either first or ultimately

in your experience in this ecosystem?

That's a great question.

You know first

I'll just kind of lay my I don't

I'm not as

involved in the military technology development.

Maybe I can speak to the development of the veterans

you know with

like I said with

with Clarksville being such a large

you know 101st Airborne being there

and then others that are coming from

from other bases around. You know

I think it teaches you a lot about

you know

how to handle problems and understand and learn

seek to learn right

and become much better at that.

And so I'll probably have to punt on the

where are we what is being developed in Nashville

for military technology to be fair

some of it probably

is quite secret.

But

you know obviously there's a lot of things that are

that are you know

the AI adoption in the battlefield

is very important to the future of

of warfare

but that's not you know

obviously not my my area of expertise.

But I do think there is a lot that

you know veterans bring to organizations

in terms of their ability to adapt and overcome

and to learn new skills and to be leaders in

in a place where again

you know this is really about leadership right now

of how do I take this technology and

and move it forward.

You know one observation on that point is

you know we're

you know I talk in my role as a consultant

to a lot of you know

C suite executives and and even CIOs, and

what we're finding is

that they're getting overwhelmed with these demos. Cause

you know

everybody and their brother has an AI technology now

I mean it's

it's unbelievable like you

you know pick up a rock and it's like

oh we got this new AI tool. And so you

the

if it is a leadership issue and not a technology issue

there's plenty if I just went out right now and said

I just need a I want to see AI technology

I mean you'd

you'd be flooded with thousands of emails and calls.

Just to say hey look

I got I got the next best

you know tool that's gonna help you.

But really

that's not the problem you're trying to solve

you know the analogy I make is

you know would you

you know just randomly go to Home Depot and say

there's something in my house I need to solve

but I heard there's really good tools out there

you know

let me just walk around and look at all the possible

tools. That's a problem for me when I go to Home Depot.

Fair enough, maybe some people are like that

like I just need to go see what I need to do next.

But you know you started about where you're like hey

there's a real problem in my house

I need to go fix it let's go find the tools next.

And so that's really we're trying to help

give the confidence to CIOs

give the confidence to IT directors to say

you don't have to just rush out there

and look at all these shiny tools

maybe let's take a step back

and let's

formulate some strategy and vision around this.

And develop use cases that connect to problems

and then that's what we're actually

we're gonna go ahead and say okay,

now it's time to open the door a little bit

and see what tools can meet that problem.

Maybe you build it maybe you buy it

but at least that's a better strategy than

than probably just sitting here taking calls all day.

Cause they are they're getting overwhelmed

they ask any CIO like how many of you you know

how many AI tools come through your door

I mean they're just like it's in some I've just stopped,

I just I I can't anymore because it's too overwhelming.

Sure.

What what about AI as an attack surface? Or a I mean

I hate to go back to the military thing,

but that is one of the you've got good AI bad AI

I've talked to a lot of people about cybersecurity.

You know

the more you experiment with it

the more flexible and dynamic your attack surfaces are

as well, so. That's right, yeah,

I mean from a cyber security standpoint

I know they're they're struggling with that you know

there's not the

you know the Nigerian prince isn't writing you in

in half-English anymore and dear sir.

I mean it's gonna sound legitimate to you I mean

it's the scams are just going up and up and up.

You know we

you know go post a job on LinkedIn right now

related to some technology

and watch how many applicants you get,

They're not real applicants.

Maybe they are,

but they're there's something that is amiss

right, is because they're just there's

you know you have automated applications,

you have automated email generation,

you have agents that can call you

and sound like they're your next door neighbor.

And so the attack services are

you're right it's it's quite

prevalent and that's something.

You know you're gonna have to really address,

and really step back and start thinking about.

You know on on the topic of of attack though

that is one of the premises that I

I think is important you know

maybe not on the cyber security side

but I say on on the technology side.

Which is right now is a time for

for leaders to have courage in

in the space of AI

so if you do have a vision and a strategy

and you've developed that clarity,

now it's time to have the courage.

You know Patton essentially said

"In absence of orders attack!" right?

And that's been a theme

of great leadership through history,

is to attack a problem.

Not with haste

and there is a difference, and I could go into that,

but doesn't mean you just hastily run off. But

I think now is a time for

technology leaders to have the courage to move forward

with attacking this problem of AI

in terms of whether it's in cybersecurity

or whether it's adoption

and implementation in your company.

It is the time to act

and so if you're in times of

kind of going back to the combat analysis analogy.

You know if you're in a place of fear and chaos and

and uncertainty

the natural human reaction is to just have paralysis,

or to make very small gestures towards a

a goal or an accomplishment.

But not really be moving forward

and so that courage to attack is to say

we gotta move forward

we're gonna dictate our future

a little bit and so that's been you know.

I like how you brought up the attack element.

I know you went cyber security

but I do think I'm also telling people no.

I think you'd be on the attack too

I think it's relevant yeah.

Very relevant. If you're gonna have a strategy

you gotta have an underlying attitude. Right.

And that and that's what a lot

a lot has missed because paralysis and fear

are what's gonna always keep you as a leader

from doing what you need to do. And

and what I'm telling people is it

that again that's not haste,

you know I had a battalion commander in Iraq who said

"don't rush to failure".

I kept that in my mind because you can

you can rush to failure just as fast.

But it is a matter of using all of your professional

experience and planning

and your leadership to say okay

we're gonna still do something

we're gonna move forward

we're not we're not rushing

and we're gonna do it deliberately

against our use cases and our vision.

Because

that's what's going to move your people forward.

I and I think

the last point is really

about a commitment to your people

because your people are really scared right now.

And so you're really gonna have to rally,

you know if there's this big a disconnect

so if you've set a vision

you've

you're starting to attack the problem with courage.

And say hey

we're gonna we're gonna go after these use cases

you gotta get your people behind it. Because

you know there is a

there is a Luddite dilemma that

that's kind of sitting out there right now.

There are some surveys

that are saying that there is a portion of your people

that may be actively working against you in AI in

in in sabotaging your efforts.

You know how real that is

I don't know but I

I do think there is a sentiment of

you know you're gonna have to

bring people along.

And then you're also gonna have to as a leader

make some choices

because if people don't wanna follow you along

those are gonna become some dilemmas

that leaders are gonna have to kind of

face here as they go.

And so really kind of put

putting that all together is

you know being on the attack

but also

who in your organization is getting behind you?

How do you bring them along,

and then what are you gonna do when some say

I'm just not going to go along.

You have a challenge.

I know you've got a luncheon that you're going to

for the the veterans peer group. Yeah.

But for the last question

I'd like to actually bring

bring you back to that veterans peer group.

And you've talked a lot about the

sort of training and the

the analogies that we've used here to explain this

this crazy world of AI

coming at us. And how really well prepared

veterans are to address some of these problems.

But whenever a peer group gets formed

there's always other problems that

that are getting solved within that group.

So for leaders that are looking to leverage veterans

what are some of the things they need to be aware of

that are challenges of veterans that are coming out of

the military and into the workforce?

What are what are the three things that that are

these are challenges that we're dealing with as

as veterans. Yeah

I think first and foremost

is an understanding of what a corporate

leader or corporations looking for

when you're recruiting a veteran.

Because you're trying to translate what you knew

and all of these acronyms and all of these things that

a lot of

you know civilian leaders don't understand. And

and in your mind you think you

you know it's

it's like I did a lot here

you know there was very

very a lot of responsibilities.

So being able to translate that one

I know

there's a lot of organizations that can help that.

Number 2 is a network you know

people lose track of how valuable their network is

as a young professional just being in a company, being.

You know if you're a young person

you're involved in some of the data

meetups here in Nashville

or in part of NTC and other places

you're building an advantage over time

just because you know people.

You know as a veteran you

you don't have that

you've been moved around the country

the world

been potentially in combat zones and your network is

is is strong, you

you know your brothers and sisters and

and in arms but you may not have known

you don't know these others that that can help you.

And it's a you know

I know Johnny

Johnny knows so and so and if I go to Johnny

he might connect me. So that's part of it is the

the second one being the network and

and third is some of the technical skills is

knowing how to start just not the bridging the gap.

You may not have done hands on Power BI dev

Databricks or Snowflake.

But these are needed skills

and so how do I just say I know how to code

or I know how to do something technical

maybe I need to go get some certification.

So what are those things that

that companies would be looking for.

And so I would say from my point of view

and that's not exhaustive in any means

that's some of the things

I would encourage a veteran to think everyone.

So that's what we're trying to do is bring

bring us all together so others can say hey

by the way build the network.

These are the things people are looking for and

and really help get them in awareness of some of that

from a decision maker as well. Man

you're talking about leadership commitment,

yeah

community commitment

and you're bringing

the type of personality to the table

that understands commitment.

Yeah thank you.

Yeah that's right.

Well thanks for the leadership.

I'm ready to charge hell with a water pistol with you.

Yeah well yeah.

Let's go. Well

appreciate you gentlemen appreciate you

you know taking time to sit down with me today

and I really appreciate your support.

I know both of you are supportive of

of these veteran groups as well.

So appreciate that and yeah

look forward to to talking more.

And thank you for your service.

Thank you for your service

It's an honor to serve is what I say so thanks