Speaker 1: Hello and welcome to the Bootstrapper's Guide to
Logistics, the podcast highlighting founders doing it
the way that doesn't get a lot of attention.
We're here to change that by sharing their stories and
inspiring others to take the leap.
It's a roller coaster ride that you might ultimately fail.
That's when I kind of knew I was on to something.
It was very hard.
Speaker 2: It truly is building a legacy the more life you live,
the more wisdom you have, because we are where we're
supposed to be kind of answering the call.
Don't shoulder entrepreneurship on your own.
Speaker 1: I'm your host, Nate Schutz.
Let's build something together from the ground up.
Hello everybody, and welcome back to the Bootstrapper's Guide
to Logistics.
We're moving into the back half of 2025.
We're well past the 100-founder story episode mark and I love
getting to talk to folks who have started their business
post-COVID.
There seems to be a dividing line of folks when they start a
business and they've been in business for 15 years and then
they went through the COVID challenges and then now kind of
the freight recession that's seemingly endless.
And then there are folks like our guest today, Justin McKessie
, who started a company in the middle of all of that and has a
slightly different perspective because he went right into the
fire day one to start his business and so happy to have
him on the show today.
He's the founder and CEO of First Choice Freight, based in
Chicago.
Justin, good morning, how are you today?
Speaker 2: Good morning, nate, I'm doing well, how are you?
Speaker 1: I'm doing great.
There seem to be three or four companies that just about every
freight broker has come out of.
It's either CH Robinson every freight broker has come out of.
It's either CH Robinson, tql, coyote I'm drawing a blank.
Who am I missing?
Tql, coyote, ch and the other big one, xpo, and a handful of
others.
I'm drawing it.
Yeah, having a bit of a senior moment here, but you came out of
the Coyote family and there's a really big number of
entrepreneurs that have started their careers at Coyote and then
went off on their own.
Can you maybe unpack a little bit of your early years, of your
career in logistics, how you got the bug for freight, and
then when did you feel like you had learned enough to start to
have some dangerous thoughts about building something of your
own?
Speaker 2: Yeah, yeah, the Coyote lineage is talked about a
lot and it's definitely out there.
We go a lot of places and everybody says like, wow,
everybody I've met is in some way shape or form from Coyote my
background.
I actually went to school at Central Michigan for logistics
management, so I had logistics in my intentions.
I never thought it'd be in the brokerage space.
I always thought I'd be at some big manufacturer or something
and figuring out the hard puzzles of supply chain.
I got an internship my junior year of college at a place
called ALS in Michigan Automated Logistics Systems in Jackson,
michigan, my hometown.
Fantastic group of people.
And that was my first endeavor into brokerage space.
And then the Coyote thing kind of came by happenstance and,
it's funny, one of the colleagues there in the office
randomly said oh wow, this news article says Coyote's opening an
Ann Arbor Michigan office.
And I said what is Coyote?
And they said, oh, it's this.
You know they do the same stuff as we do, they just have all
these.
You know young people and the office environment.
So I Googled Coyote logistics.
I had one year left of school and I decided like, well, if I'm
going to do another internship, maybe I'll reach out to these
guys Did that and was accepted in.
You know, I took my next summer to Chicago.
I actually pulled out a $2,000 personal loan to move myself to
Chicago for an internship.
I also had to pay Central Michigan for a credit.
We had to have internships, but that was my foray into Coyote.
So I got there as an intern in 2014.
Immediately knew I was going to come back and was accepted
full-time.
The year following Getting to Coyote I was in the traditional
carrier sales role, kind of growing through that.
We were acquired by UPS shortly after my entry there and that
is kind of where my career took the most interesting turn and
really was a springboard for what I've done since then.
I was lucky enough to be part of the early group of folks that
were dedicated to the UPS side at Coyote, got to basically play
in their sandbox and have a ton of different roles, building
teams and building new endeavors all around just how we could
create synergies with UPS.
Literally, my first role there had no job description.
It had the name of one gentleman that said work with
Rock to find synergies.
First hour I was Googling like, is this one of our employees,
is this a company?
And a gentleman by the name of Keith Hargarten, walked in and
said hi, I'm Rock, we're going to be working together.
So he was in charge of a lot of the intermodal side and I got
to work with him and it was wide open, which, as someone that's
a self-proclaimed like builder and tinker my whole life, this
was a space where I could really shine and say you know,
whatever is out there, go find it.
Go find a way that Coyote can help UPS do it on the asset side
, on the intermodal side, and everything was fair game.
So that was really where my entrepreneurial spirit was able
to shine in the world of Coyote UPS.
So I did that for quite a long time, had a lot of success there
and always knew in the back of my mind it was going to turn
into, you know, for my career, something that I wanted to do
start another business.
I again, by stroke of luck, had some friends from Detroit that
had been in contact with me and the timing was right, where they
said hey, we're thinking about starting a brokerage.
I had plans mapped out, I had multiple business plans put
together, different names, different areas we wanted to
focus on.
I flew out the next day and pitched them what I wanted to do
and told them my vision and it was okay, let's do it.
So I was at BP Logistics at the time.
It was a short stint between Coyote and what I'm doing now
and I told them exactly what I was doing Another great group of
people, very honest with them and they told me go do your
thing.
It was no hard feelings, it was .
We see where you're coming from .
So that was my.
My jump into entrepreneurship was okay, it's go time.
There's some other people that I know that are ready to go as
well.
And I closed the laptop at one place and the next morning I
opened up my new laptop and got started on the dream that we had
set out in front of us.
Speaker 1: And that dream is now First Choice Freight.
You're in your three, four years in.
It's been a tough climate for a lot of companies in that space,
so you have to be able to have a high pain tolerance to do what
you do, but also be somebody who is chronically not satisfied
.
When you start talking about being a builder and a tinkerer,
I'm getting pictures of you as a kid and if you had multiple
business plans and multiple names.
So you're somebody who likely has a very active thought life
and has been that way for a long time.
So what were you like as a kid?
Speaker 2: Oh yeah, that's absolutely correct.
Growing up I was always messing with something I probably drove
my mom crazy Like a VCR that was eating the tape speakers
that weren't working, that were left behind in our garage.
I would find them, take them apart, find a way to make it
work, and usually I would leave half the parts out and it'd be
working better than before.
Anything that I could get my hands on, I was constantly
messing with it and trying to build it, improve it.
I think in hindsight we probably just had a lot of
voided warranties sitting around after that, but it worked out
sometimes we might have to explain what a VCR is too.
Speaker 1: We got a younger audience.
So keep going, so you did you find ways, then, to make money
doing things like that?
Also, I did so.
Speaker 2: I think from that stage that carried into my you
know my driving stage where I was messing around and tinkering
with my vehicles, my first entrepreneurial endeavor was I
built these light kits for the bed of my truck that went under
the rails and they shine in different colors at nighttime.
This was I don't even know what year it had been before.
It was like standard in trucks today Got a lot of comments on
it and I was like, well, gosh, this took me $30 to put together
.
I started buying up the parts for it.
I assembled instructions on how to do it.
I created a eBay motors page and I posted them on there with
different thoughts and instructions, and it took me a
while to find the price point.
But I was testing it out and lo and behold, I started selling
them for $60, $70.
And I'm like, okay, I'm making money.
I was never serious about it.
It was just something that, again, I was playing around with
, but without even knowing that that was entrepreneurship at the
moment.
It was something that I was like well, I can do this for $30
.
People like it.
I'm seeing companies sell it for $200.
Maybe I can fall from the middle and make a little profit.
So I think that was my first leap and you know, from then on
out, there were actually a period of time where I would buy
and sell cars that I was even driving, or if I just knew
something random like it's.
You know, it's October and there's a four-wheel drive SUV
that's for sale.
It's gonna be worth a lot more in December when people want it.
So if I could pick that up and sit on it for a while and wait
until the time was right, I can make a profit on it.
So my mom would help me clean things up in the yard and repost
them on Craigslist or anything like that.
So yeah, there was always that like what can I do to make money
, to improve something, to find a different way to make money,
to make money and be profitable?
Speaker 1: So that you mentioned price testing on eBay.
Pricing is a complicated thing.
On one level, there's a bunch of theory behind it, and then
there's also just the value that somebody places on.
Whatever the thing is that you're selling, and they get to
decide what it's worth, not you.
And so when you say I knew what my costs were, I knew what my
competitors were doing and so I wanted to test it, did you just
increase the price by five bucks every time and see where demand
stopped?
Or how did?
Was that just another way to tinker on something different?
Speaker 2: Yeah, and I actually hadn't thought about this until
you brought it up.
But on eBay it would show you if I posted at a hundred dollars
, you got five views and no buy.
It now clicks, right.
So I think I posted it like $120 and no views, no anything.
So I'd go back in and I'd give the old price cut right.
Oh, this is on sale for 99.99 and might've gotten 25 views.
And then I think when I dropped them to like $68, the views
went up and all of a sudden I had the first purchase and then
the second and the third and the fourth and fifth.
So I was like, okay, I just found my sweet spot where I can
sell some of these things.
And it never went more than a dozen or so, but it was a fun at
the time.
It was just fun for me as a young man to say, like all right
, I just made money off selling something on eBay.
Speaker 1: Out of thin air.
Speaker 2: Out of thin air.
Speaker 1: And that is the beauty of entrepreneurship is
the market.
There's a scoreboard.
The market tells you how good your idea plus your execution is
.
There's no subjectivity left.
Somebody made the decision and voted with their dollars that
they want what you sell.
And in the freight world, yes, on one hand it's a pure
commodity.
Transportation is transportation, and yet some
companies have a lot of success selling transportation and
others don't.
And there's going to be a relationship component to it, of
course.
And then there's also going to be knowing what the potential
customer or your existing customer values and trying to
price it right.
So how do you think about tinkering with price and costs
within a freight brokerage in a volatile world?
Speaker 2: Yeah, great question.
For us.
We're in the drayage space international containers,
imports, exports.
It's a space that has lacked a lot of ingenuity or improvement,
really, since day one.
Our hardest endeavor is trying to prove real value.
It's a space that a lot of people are just middlemanning
right.
They get a response from a customer, they copy and paste it
to the carrier.
I've watched it happen.
They get a response from the carrier, copy and paste it back,
and it's because it's a very complex part of our industry.
The costs don't make sense.
The jargon that you hear in and out of every conversation it
just it doesn't add up.
So we're doing something different where we're showing
them the data can be useful.
We're showing them transit time on the water, things that
people aren't usually offering.
So for us and we're not even trying to necessarily charge a
premium for it but we're trying to buy our way into their, their
company, at the same or lower cost, but to tell them we're
doing something that truly is more valuable or bringing a new
angle to the industry.
It's incredibly tough to break through the noise of the
industry and say, hey, spend your dollars here because you're
going to get more bang for your buck.
That's our biggest hurdle and that's what we hone in on is if
we can show them the value that they can get more for their
money.
You know they're spending With us, we're winning.
And when we do finally break through and show them, all we
hear time and time again from the customers we do have is like
wow, I can't believe you guys are actually doing this.
You're doing what you said you were going to do, and that seems
so simple.
But yeah, so our value proposition has been exactly
that.
Like we're going above and beyond, not even necessarily to
charge you a premium amount, but just to do what we think is
kind of table stakes today in most parts of the industry.
Speaker 1: And that's the bridge , I think, between sales and
operations.
You take a potential value prop and put it out into the market
and hope somebody is interested enough to try you and you've
generated interest.
But now is interested enough to try you and you've generated
interest, but now you've got to follow through and deliver.
And that's where I think it is frustrating.
I'm an operator myself.
It's frustrating to see the hype that gets thrown out and
marketing messages that get attention when you know some of
the companies behind it can't actually back it up.
And when you're an operator who does things really, really well
and maybe doesn't have the flair or the dramatic pitch, you
can't always trust that the work is going to speak for itself.
You have to.
The customer has to in some cases, be shown the value that
they're getting.
And I'm curious for you also, knowing that you have a
co-founder in the business.
Most of your career up until starting First Choice looks like
it was in ops, and now you're having to do ops and sales.
How did you and your co-founder decide who was going to do what
?
How did you set boundaries on this?
Is my area, stay out of it or no?
I really need your help on this because you're better at that
thing than I am.
Speaker 2: Yeah, I think you just described me to a T.
I've always been the operator and builder behind the scenes,
extremely proud of what I can build and do and put together
great processes.
But I was never that person trying to be out in the
spotlight and necessarily great at showing or talking about what
I was doing.
My co-founder, tyler Billings, has been a sales leader his
entire career, so kind of a great duo in terms of like, hey,
I'm going to build this product that I know there's a market
out there for you.
Go, you know, boots on the ground, show people what we can
do and talk it up and get their engagement.
So in a lot of regard, that's a you know, probably a dream
scenario where you have somebody that's super sales focused and
someone that's super ops and building focused.
Now, that doesn't mean that we're not all selling all the
time.
Right, everybody in every seat.
I have to be selling the vision behind why I wanted to build it
this way.
And gosh, even in the accounting seat they're selling
right the end experience for our people on the other side of the
equation.
If there's bad billing scenarios, that can be as
terrible of an outcome for a customer as the front end
experience.
So we're all selling all the time an outcome for a customer
as the front end experience.
So we're all selling all the time.
But I think having that split where it's if there's something
with the product to be improved or the operations or the overall
business, that's me and I will go do that and having somebody
that is on sales, I can get this message out there and see what
we can bring home.
Speaker 1: And that sounds like you built it with intentionality
.
You built your team with intentionality from day one, and
I know it's easy to romanticize entrepreneurship and yet I also
know it can be a complete grind and a lot of companies get
close to not making it way more than people will ever know.
Were there any lessons like that that you had to learn along
the way or learn the hard way yourself?
Speaker 2: Absolutely.
You know, to rewind and something that was completely
skipped in the first choice freight intro.
You know I mentioned going to Detroit with my partners at the
time and that was the beginning of it Flew out.
We had great plans.
The goal was just to grow and see where we could take a
brokerage in one to five years.
At that point in time, the market being what it was was
coming off of the COVID high Margins weren't there.
Business was hard to come by and you know my two partners at
the time, very successful entrepreneurs in their own right
from the Detroit community.
This was their fifth, sixth, seventh, uh, dive into business.
Right, they've already had successful businesses.
I was the one in the logistics space.
So we got six months in, realized the cash that would
need to be on hand to continue growing it at our pace and we
were growing pretty quickly.
Right off the jump they were like, hey, this is kind of not
what we signed up for.
Let's maybe just scrap the plans and move on to something
else, right?
And that's, in all honesty, probably the right move for them
.
There's a lot of other places where they could have parked
their money outside of logistics at that time.
That would be a smarter move and I was leading with passion
for the industry and the vision they were leading with smart
money.
So, luckily for me, we were able to come up with an amicable
solution, had great partners in them, to where I would continue
on and take the business over entirely, make them whole and
from that point forward.
So we went from months one through six, growing hiring,
realizing it wasn't going to work the way we wanted it to, to
saying like all right, I'm going to take this solo, I'm
going to correct course, essentially make sure this thing
is sound enough to work, and then kind of refound it again
six months later.
So it was the highest high, followed by a reality check
instantly.
And I think that was the biggest lesson.
Was you know, I think from a big place like Coyote, you know
how to pull levers to grow, or what you think is growth?
Right, if you want sales, I can pull a lever that'll drive
sales and drive revenue and we'll get people in.
Well, what's happening on the back end of that?
Is it profitable revenue?
Is it taking us 10 hours to cover a break-even load?
Right, there's a cost associated with that and the
struggles of growth?
Right, we didn't know where some of our receivables were at
one point where and when you're running out of cash, you're
saying, well, we have to go find that right.
So everything, aside from the logistics piece I knew very well
, it's the boring stuff that you don't know about that will come
back and get you, and that was an instant lesson where it could
have been the end.
Six months in and luckily for the partners I had that were
willing to let me continue, we were able to correct course
pretty quickly and get this thing back on the right track
and grow from there.
Speaker 1: I love the candidness that you share with that.
People think businesses fail because they decline.
Sometimes businesses fail because they grow too fast and
their cash flow gets away from them, because it takes a lot
more working capital to run a $20 million freight brokerage
than it does a $2 million freight brokerage, and so more
sales faster can actually speed up the end of a business if they
don't have good accounting.
And it's a healthy reminder for everybody who is maybe
listening and is passionate about an idea that they have
been thinking about for a long time and want to get into their
own business or start their own thing.
The secondary things are what you end up spending a lot of
time on.
I use the example of like a bakery somebody who is a really
good baker and is like I want to make donuts because I or you
know pastries, because I'm really, really good at that, and
so they open a donut shop.
Well, they end up spending the least amount of time actually
baking.
They spend the rest of their time dealing with a landlord and
with vendors and customers and chargebacks and HR issues and
all of that other stuff, and so if you it's kind of the don't
follow your passion advice unless you have people around
you that can fill in those gaps, because, especially in
logistics, the dollar amounts are too big.
It takes a lot of cash to run a even a medium-sized freight
brokerage.
You've got to have millions and millions of dollars available
um, should a customer not pay, or you have to front money to
the carriers before you get paid by your customer in maybe 45 or
50 days.
And those aren't sexy things, but they are the building blocks
of a company that lasts.
Speaker 2: Anything to add to that?
Yeah, I think you nailed it right.
I knew it about six months in.
If we were going to fail, it wasn't going to be because I
didn't know logistics or I didn't know what I was doing.
It was the stuff that you're not seeing and you're not aware
of you haven't been trained on.
There's nobody to train you in these environments.
Right, I think, being open and honest with yourself about what
you don't know as you jump into entrepreneurship, obviously you
have to go figure out everything , right?
So my mentality was I'll figure this out.
Oh, the accounting, I'll figure this out.
I know where to look.
I know it'll figure itself out in some way.
Like, the things are going to come to me that are issues, and
that's very naive, right?
I think if you can't be honest with yourself and say, wait,
this is beyond my reach, maybe I should tap a resource for help.
You my reach, maybe I should tap a resource for help.
You can end up in a lot of trouble very quickly and
sometimes irreversible.
So that's probably a trap that a lot of people fall into.
I'd imagine it's one that I almost fell into myself is not
being able to say to yourself you can't necessarily do this
one.
Let's find some help.
Speaker 1: You're a very thoughtful person, justin.
In all the time that I've known you, I know your mind is
constantly working through things.
Do you consciously think about the difference of your
professional life and your personal life as an entrepreneur
, or is it just one big ball of yarn?
It's all mixed up together?
How do you look at the different parts of your life,
given how large of a role entrepreneurship can take and
just dominate?
Speaker 2: Yeah, I think year one was a big ball of yarn
Because there was no other way.
I had to juggle whatever I could find a way to make things
work.
I try more than ever to be very intentional about the time that
I spend, you know, with my family, with my loved ones, with
my friends, how I show up for them versus how I show up for
the business versus how I show up for myself.
I need my own time where I'm a big fitness enthusiast.
I need that time and making sure that the other areas don't
impact the rest of them, and it's extremely difficult trying
not to bring home the stresses of work, trying not to, you know
, have the carryover from personal life into the business
world Right.
So, yeah, I do think a lot about segmenting them and trying
to understand how they factor into each other and making sure
that they're, all you know, coexisting in a peaceful manner.
That is also not running me completely ragged.
Speaker 1: How do you think about goals, then, for the
future?
Speaker 2: Yeah, I think those they have to intertwine right.
It's you could set goals individually and say, well, I
want the business to do this.
How does that affect my personal life and marriage and
kids and all the things that come, which I'm not there yet,
but I will be in the very near future?
So it's trying to understand does this business goal align
timing wise with what I do with my personal life?
Can my personal life sustain what I'm doing with the business
?
It's a tight race between all of them together and I think you
have to be intentional and, again, honest with yourself in
the business world, honest with yourself in the personal life
world, to know where you're falling short and where they're
going to work well together helped you form that kind of a
mindset and the ability to be that mature and wise about how
you want your life to go.
Yeah, great question I would.
I mean my mother first and foremost, who raised us as a
single parent, myself and my older sisters.
I think a lot of my intentionality comes from that
Extremely supportive right.
I knew that she was the one that was going to help me
understand things in a way that made sense.
If I was sporadic as a kid or even as an adult, I think she
gave me that courage, if you will, to say like okay, go do
what you want to do, but take care of your responsibilities.
Make sure you're not doing something that's going to hurt
others if you're taking a leap of faith on something.
But I would give most of the credit to my mom and to my
sisters.
They were like second mothers my entire childhood.
That trio of women definitely gave me a strong ability to be
intentional, first and foremost, about my actions and my desires
.
Speaker 1: Well, and I'm sure they're all very proud of seeing
what you've done so far and knowing that you've got a lot of
runway ahead of you, because that's part of why you do what
you do Knowing you, I know that's true.
It's not just about money.
It's not just about solving cool problems, although that's a
part of it too.
It is people that want to have an impact in a positive way and
prioritize what matters.
And when you can find that overlap between your chosen
career, your finances, your friends, your family, your
relationships and something bigger than yourself, then
that's a pretty good place to be .
I mean, you've got to feel very fortunate, and I know you
shared with me beforehand that you haven't had a lot of chances
to stop and think about this journey that you've been on.
I hope this provides some of that a chance to pause, reflect,
recharge for the next stage of what is coming, for First Choice
and for you and we're grateful for you for opening up and
sharing your story I always like to ask is there any advice that
you would give to somebody who's maybe a couple of years
behind where you are right now, so that you can pay it forward
to somebody else who's on their own entrepreneurial journey?
Speaker 2: Yeah well, I definitely appreciate all the
kind words.
I think the thing that I would give the most advice on is
protecting your time, time management and it's something
I've always preached before.
Entrepreneurship as well.
There's a lot of fires that are going to be thrown your way any
given day, right as the guy that has to be the one to you
know the end all be all.
Your day is going to be pulled in a million directions, and if
you can't be, again, intentional with your time and protect it
and decide what fires can be left burning for a little while
while you focus on the main fires, it's a quick recipe for
disaster.
So I think the one thing that has helped me the most is time
management making sure that I am focused on what I need to be
focused on and letting those small fires burn, knowing that
I'll get to them.
It's not ignoring them by any means, but if you don't be very
intentional with your time, you will quickly run out of time and
then realize you didn't get anything done in that day.
Speaker 1: I once heard the analogy of owning a business is
like riding on the back of a lion it's really powerful and it
can take you really far, really really fast, but at any point
it can also turn around and bite your head off.
So it's this beautiful contradiction of risk and reward
, and using the time management part of it and prioritizing what
you're going to focus on gives you a greater likelihood of
being successful, and I love that you brought up health.
It's underappreciated, I think, that to be at your best from a
performance perspective, you need good sleep, you need
exercise, you need a healthy diet, and it not only manifests
itself in your physical body but in the way that you show up for
others, how much stamina you have to make it through the day.
Your mental clarity and the happiest entrepreneurs I'm not
necessarily going to always say the most successful, because
that's subjective, depending on how people define success but
the happiest entrepreneurs that I know tend to be the ones that
prioritize their health, and so that's another good lesson.
It's a reminder for me too.
That's why I love to do.
What I do is I get to learn from dozens and dozens of people
doing what you're doing, justin , and we're grateful to you for
sharing your story and we are definitely all rooting for you.
Awesome, I appreciate it, nate, always great talking to you and
thank you so much for having me .
Speaker 2: All right, are definitely all rooting for you.
Awesome, I appreciate it, nate, always great talking to you and
thank you so much for having me .
Speaker 1: All right, take care, my friend.
Thanks for listening to another episode of the Bootstrapper's
Guide to Logistics, and a special thank you to our
sponsors and the team behind the scenes who make it all possible
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To learn more about the show and connect with the growing
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And, of course, thank you to all the founders who trust us to
share their stories.