Ep. #65: Matt O’Mara, CEO & Founder, Whimsy Intermodal

Episode Transcript
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Andrew Silver (00:00):
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Matt O'Mara (01:17):
All right, we're back.

Welcome back to another episode of Freight Pod.
I'm your host, andrew Silver.
I am joined today by Mr MattO'Meara, the CEO and founder of
Whimsy Intermodal WhimsyTrucking Intermodal whimsy
trucking.
This is our first foray intothe intermodal world and it's no
time like the present, with thecurrent tariff chaos going on

(01:52):
and all the impact that thatwill have in imports and the
intermodal business, and we willget there.
But I want to go through yourwhole story.
I know you started as a truckdriver and started your own
business and have grown it tothis very successful company.
So there's a lot for us, Ithink, to learn, even in just
the 10 minutes I spent and thisis the first time we've ever met
or spoken but in the 10 minuteswe just spent chatting before

(02:15):
the episode started, I wish I'dbeen recording the whole time.
So I think there's going to bea lot of good nuggets today.
Welcome to the show, matt.
How are you doing?

Very good, very good.
Thank you, andrew, I appreciateit.
Thanks for having me.
So take me all the way back.
How'd you get into thisbusiness?
All right, I was a mover, Iguess, and in the moving
business we were busy Maythrough October and then October

(02:49):
through May.
We would do industrial moves,office moves, things like that,
because not many households weremoving or whatever.
I had to get into some otherbusiness that was more
consistent.
There was too many ups anddowns you know now we call that
what White glove delivery,mm-hmm, yeah, but I mean I've
done industrial rigging, allthose things that go with that,

(03:12):
office moves.
And then, as I said, I had toget into something more
consistent and I got intohauling containers.
For as an owner operator and,um, I had, at the same time I
would tell the dispatchers, giveme all the container, all the

(03:32):
dispatch.
Nobody, nobody wants right, um,and so I I've always, always,
uh, been successful at turninglemons into lemonade so became
an owner-operator.
A company that I was working atgot bought out.
The company that bought themdidn't want any company drivers,

(03:54):
so I took over a ton of thesetrucks and a ton of their best
drivers, and that's how Iexpanded for multiple trucks.
We did garbage too.
We held waste transfers so we'dgo to transfer stations with
our open top walking floors andpick up garbage and take it to
the landfills and pump it offinto the landfill yards.

(04:17):
Reason being is garbage mailfuel these things move every day
, right Containers usually.
So I just needed to get into amore consistent business.
Turned out, I was prettynatural at leading drivers

(04:48):
Probably one of the reasons.
my father was a labor relationsguy for Illinois Bell for many,
many years.
He knew what it was like to beboots on the ground, talking to
the people that really areaccomplishing the work, and so
people just started falling inand, uh, working with me.
The team grew right, justorganically.

(05:11):
Uh, how old were you when you?

how old were you when you took over the the 10
trucks and drivers?
So it was like 27 yeah, that'syoung to be kind of making that
big of a commitment.
Why did you feel like that wasthe time and you were ready,
fearless or stupid, fearless andstupid.

(05:35):
Or fearless or stupid.
I started my company at 27 andI was fearless and stupid, yeah,
so you might have been an or.

Yeah, so yeah, you have to be.
You know, I had nothing to lose.

And when was this 96?

Yeah, 1995, 94, 93.
Actually, Wimsy wasincorporated in 96.

There was a lot of work that we did before.

Whimsy actually was an incorporated carrier and why
containers?

Why intermodal?

I have no idea, just was what was in front of?
You, I guess you know I trulybelieve that you can't press
things and you have to let youknow, like take advantage of the
opportunities that come to you.
So I guess at the time that wasprobably my best opportunities.

And just for context, for the audience,
because we're going to walkthrough the whole story.
But what does the business looklike today in terms of like,
its size and what you guys focuson?
You know, intermodal versusover the road story.
But what does the business looklike today in terms of like,
its size and what you guys focuson?

you know, intermodal versus over the road
so one of the most difficultthings that uh actually is when
you're a legacy company, beenaround a while, right, um, and
you're in a more advanced world.
Biggest thing for us was uhdigitizing, going paperless.
I want to say, 12 years ago Iuh we signed a contract with the

(07:13):
tms system and we tried toimplement it.
I didn't have the right teamteam members to help me
implement it, so that we had to,we had to cancel that.
Eight years later we started uhwith trinium and uh, same thing
.
I got a lot of resistance fromeverybody on the team, failed

(07:37):
again.
And then the last time um wegot trinium, I hired a whole
nother team that didn't evenknow intermodal.
So I had to teach themintermodal.
They were all just techie uh,data analysts, all these type.
Um teach them all intermodalwhy the other guys are

(07:58):
dispatching.
And then my idea was just tomerge the teams, but there was a
lot of conflict to end uplosing the original dispatch
team, moving these guys intodispatch and then hiring a whole
other set of guys to retrain.
And so finally it was I don'tknow June of last year that we

(08:21):
finally went paperless andembraced the whole TMS system.
Yeah, so those things are verydifficult to overcome when you
don't just start out as a techcompany.
What we're really good at,though, obviously because
containers or freight are muchlike water, and you know this

(08:44):
it's going to take the path ofleast resistance.
So if you can create a niceflow, uh which is what we do
right same day, next day italways amazed me when uh amazon
said they're gonna have two daydelivery or next day delivery
and then same day delivery up atwhimsy.
We've been doing it since 1996.

(09:04):
You know, we deliver containersthe same day that they arrive,
we deliver them the next day.
We always used to say it'sfunny, because as the railroad
kept reducing the amount of timeyour container could dwell at
the rail yard, we say it's goingto be like an airport.
Right, you have to be therewhen your your container arrives
.
You know, sit by the curb, waitfor it, get your container
arrives.
You know, sit by the curb, waitfor it, get your container and

(09:25):
then leave, eat it.
So we haven't gotten to thatpoint yet, obviously because
there's just not enough driversfor the amount of containers
flowing in currently.
So that was a big obstacle to,I mean, many times.
It just shows that, as a leader, right, I didn't.

(09:46):
Third time was a charm.

In terms of getting the technology
implemented in a way that peoplewould use it.
I mean, that's an interestingpoint that I don't think some of
us leaders do a good enough jobof is understanding the
importance of the implementationand the buy-in and needing to
have champions who support theidea of moving on to this new
technology, because you and I,or you as the ceo, can go see

(10:13):
the latest.
You know, you can go meet withtrinium and be like man.
This would make my life so mucheasier because you see the
problems from 30 000 feet.
A lot of cases, you see likeyou know all the errors that can
happen and mistakes and lostpaperwork and this, and that the
people on the floor doing theactual work they're just like
used to what they're used to.

(10:34):
I mean, they're used towhatever it is 40 keystrokes
they have to do, or you knowthey put this paper in that pile
and this paper in this pile andthey don't care necessarily
that you think it's going to beeasier.
They know what they know andoften there's a disconnect
between the person up top whosees how the problem can be
solved and the people at thebottom who are actually doing

(10:55):
the work, and it's justimportant for there to be some
type of connection there made oryou will have one or two failed
attempts.
I'm curious, like you know, asyou think, about how you made it
work the third time.
What, what was different?
I mean you mentioned hiring andhaving to basically rehire the
whole team.
I mean, is that kind of thecentral factor, or were there

(11:17):
other things that maybe can belearning?
Learning points for for otherswho will go through something
similar?

yeah, I mean, can you imagine like scale, like ch
robertson, yeah, going throughthe same legacy things?
I mean that, you know, peopledon't talk about it, but it's
monumental and it's exactly likeyou say.
You need the people to buy it.
Um, you know, now everybody.
Oh, you know, I went fromaverage age was 48 and up, so

(11:45):
now my average age is 36 andbelow.
I'm an old fart and it'samazing, because I was like,
yeah, nobody's really going tounderstand how all the nuances
of the intermodal world becauseyou know, it's just as bizarre
as the world that we live in.
Most of the time, the do's, thedon'ts'ts, you shouldn't have

(12:08):
stuff, and and, and.
Then, when you put a process,and you put a million and ten
processes in, and there's goingto be a million and eleven that
you didn't think of, right, so,uh, yeah, I mean, I still love
it, though no-transcript, likethe exception, is the rule.

So you know you might solve a hundred problems
with automation, but you missedthe hundred and first you missed
the hundred and second youmissed the hundred and third.
And those are the three thatare going to get back to your
customer.
And customer doesn't give acrap how many things you
automated.
They care that this order gotscrewed up.
And they didn't know in advance, because you know your process

(13:13):
wasn't clean enough.
Yeah, so well, we're.

We're at the point now, uh, where the driver
doesn't leave the either thereceiver or the shipper without
sending the BOL or the POD.
So the customers are gettingtheir BOLs, their PODs, within
30 minutes of signing.
So, you know, these are theimportant things like being in

(13:38):
the business a long time, youcan add all the tech you want.
The other thing is tracking,tracing on time.
You know these.
These are the things that, uh,that people want to partner with
you for right.
Um, if, if you can, I can tellyou where my driver is, or I can
give you access to where wheremy driver is for your particular

(14:01):
load, and you can see that andyou get all that documentation.
And we do, uh, you know, we doa lot of niche.
Uh also, uh, reefers, triaxleswe've been doing it for so long.
We have a lot of equipment andwe have the infrastructure.
A lot of times, uh, whenever youtalk about the vc everybody

(14:22):
wanting to get in you, you gotto have an infrastructure, you
got to have processes.
There's so much that can gowrong.
Freight brokers everybodyfights for the owner-operator,
but the truth is we've got awaiting list for owner-operators
because we give them thesupport that they didn't even
know they needed Support, beingthey have all of our facilities

(14:42):
to stop at, go to the bathroom,get things fixed, wash their
hands, take a break.
You know these are the thingsthat drivers need not need but
deserve.
So when you give the propersupport, you're going to get a
following.
You know that and that goes.

(15:03):
You could add all the 951million things, but you know,
then you have to train all thedrivers on how to use everything
right at the same time and uh,obviously it's, it's easy, but
for some guys it can be a littlefrustrating.
If you don't give them theproper support, uh, they're

(15:24):
going to want to quit.
Like I always say a lot oftimes in this business.
It's amazing to me, becauseeverybody complains.
You know, intermodal business,one of the things shippers and
receivers would always say isthey don't call, they're always
late, and we started withpre-pulling containers so that
we didn't have to sit at therail or the depot that day and

(15:45):
then come up on the excuse onwhy we're late get the box clean
it, that's what we do.
Uh, we don't care if you'repaying or not.
Uh, 95 of any export, we dothat.
Uh, one of the mechanics or anemployee at whimsy will blow it
out or clean it, check for holes, all of those things, because
we know dry runs are a big issue.

(16:08):
Who you know who wins in a dryrun?
Nobody, it's just a.
It's a loser, right?
So, uh, the thing uh, all thesecheaper carriers can't do is
they can't find ways to take outthings that cost people money,
right?

our only add value is when I can save you
money I can't find ways to takeout the things that cost people
money.
Will you explain that I missedthat point for my audience?

okay, um, dry runs.
Like.
You show up with a container,uh smells, it's dirty, it's got
a hole in it, customer don'twant to load it.
Who are they gonna blameimmediately?
They're gonna blame the carrier, right, if we show up with an
inferior container.
But if you're ordering, uh,just a general purpose container
, then there shouldn't be anissue.

(16:57):
Then you have.
Then.
Then you have now this point ofcontention where you shouldn't
have brought this container.
Well, well, the driver doesn'tget to pick.
He goes into a yard that'sstacked full of containers and
they have to put the best one on, and then we have to work with
it or get out of line, go backin anger.
People get a different one out,right, generally, as long as it

(17:19):
doesn't have a hole in thesides of the floor, we can clean
it.
That's what we do.
Those are the things that I amtrying to explain.
Cost somebody money or arelationship, because you either
have to split it or find a way.
I always say it's not whathappens, but what you do after

(17:41):
it happens.

Yeah, no, it's interesting because that would
be a challenging thing forsomeone to look at and say, okay
, well, we're spending an extrahalf hour, hour of someone's
time cleaning this every timeand so we have like a 1%
rejection rate or even lesspercent rejection rate, leading
to zero or 1% of dry runs,comparing to maybe a cheaper

(18:07):
alternative carrier who's likeI'm not going to spend the hour
cleaning it, and they have a 5%dry run rate or 5% rejection
rate.
Like it's hard to do the mathand necessarily correlate that
to savings, but like I cangenerally just appreciate your
thought process of I'm going todo everything in my power to put
my customer in the bestposition to win and like to

(18:29):
reduce the chance of a loadgetting missed or or you know, a
load getting rejected, atrailer, a container getting
rejected, right, and those arethe things that I I I actually
do.
I understand now with thatexplanation, I appreciate it and
those.
That's a perfect example of alittle thing that, like a really
high quality provider is goingto do that you know, on paper it

(18:53):
looks like they're spendingextra money but because you
don't necessarily see it in theprofit of, like you know, fewer
dry runs, but your customers arehappier with you because your
service level is going to behigher and, at the end of the
day, like that's what matters,right.

Well, you're probably pretty close on the
analytics of the failures, orwhatever the case may be.
But at the same time, what Iwould just like to remind you is
if the customers needs to makea sale and today's the cutoff
right, and now they're not goingto make the cutoff, uh, maybe
the customer then cancels theorder.
You know you're not going tomeet my terms of delivery, so it

(19:29):
triggers.
It's in my life, it's.
It's never one thing, right?
Uh, if you don't understandcause and effect, then you're
going to get clobbered.
You're just going to getclobbered because you don't
understand.
If you fail on that, then thatcreates that.
Now that forwarder, that book,that trucker now looks like a
clown because now the shipper'sfreight ain't going to make it.

(19:51):
And the same thing as far asthe condition goes.
If you're going to a thirdparty warehouse and they're
responsible for the freight toget to Australia properly, they
don't want to load any kind ofinferior container and their
idea of an inferior container ismuch different than the
carrier's idea of an inferiorcontainer.
So you have the customer that'sbuying or shipping the freight.

(20:13):
You have the warehouse that'sgoing to be loading the freight.
Then you have the carrierthat's coming to pick it up.
These are the points ofcontention that you know either
make or break you with yourrelationships with your
customers.

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(21:35):
decisions around quality, that'skind of out of your control is
to limit the number of kind ofinconsistent warehouses that you
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keep as much consistency inyour network as possible.
So you know, you know 80%, 90%of my freight I'm picking up and

(21:58):
dropping off at the same placesall the time because you
understand their rules, youunderstand what good looks like
versus if you're just on thespot market.
Every day, and every day you'regoing to a new facility and
every day you're engaging withtheir new rules.
You don't know what they thinkgood looks like.
And I'm curious like in yourworld, what percent of your
business are you running as likeconsistent lanes, consistent

(22:22):
facilities, versus playing inthe spot market where there's a
little more risk of kind ofgoing into the unknown?

So all over the board, to answer that question,
we've got customers that havebeen paying the same thing
before COVID, through COVID andafter COVID, so they don't even
know what everyone people talkabout.
You know the whole thing.
They don't understand.
They're like I don't know,wimsey provided us the same
service, blah, blah, blah.
You know, maybe they had to paydetention at the rail for

(22:52):
congestion or whatever.
You know these things.
But as far as price goes, toanswer your question, I want to
go to every facility.
You know yeah, do we have.
We have plenty of customers overour 29 years of existence that
we've been going to for a goodlong time, whether it's a drop

(23:14):
or pull or a live load.
Everybody understands.
I always say know what you signup for, right.
So everybody knows what theysigned up for and those
incidents.
Like I said, we'll move 200containers a day and I have to
answer emails and talk to peopleabout two moves that went bad.
So when you talk about right,showing up with a good container

(23:38):
or what the rejection figure is, I want a zero rejection.
That's my goal, uh, and mydrivers.
They need to understand whatour expectations are, right and
and so when they do show up, andthen you and they get rejected.
And then they I get a pictureof it and they say, well, you
know, I want to get paid forthis.

(23:59):
I say, yeah, how can you, howcan I get you paid for that,
right?
Well, you didn't even open thecontainer because there's,
there's contagion, uh, you know,uh, there's, there's times when
drivers don't do their jobsproperly.
So, um, that's why we have, weset a certain standard.
Uh, andrew and um, it needs tobe adhered to it.
It needs to be, uh, better eachday, right, I mean every day, I

(24:22):
tried to be two things a betterperson and less of a hypocrite,
right?
Those are the two things I aimfor every day and they kind of
go hand in hand.
So, you know, I like to offeras much transparency as possible
.
At the same time, I wouldappreciate transparency, right?
So, those, that's just the waythat goes.

(24:45):
And you know, like I said, Iwant to go to every shipper.
I don't care, you know, if theydon't have a bathroom or they
don't want to let the driver inthe bathroom, then we're going
to put it in the notes, you know.
Tell the driver to stop beforehe goes there and get to the
bathroom, I found that I can'tchange people, that I have to
just work in the parameters ofthe challenges that I'm given,

(25:07):
and so we just try to understandthose, make notes and do things
, not cry over and over againabout things that nobody's
willing to get down and dirtyand change.
Pet peeves are these people goon linkedin and talk about the

(25:27):
lines at, uh, norfolk southernor waiting time or all these
things and paying for lifts andall all that goes with that and
and you should have known whatyou were signing up for, right,
uh, and I call it's just part ofthe game where we call the rail
the belly of the beast.
You got to get into the bellyof the beast to understand how
it works.
Uh, we, we have a, a terminalby every rail.
Um, for that reason, right, wewant to be able to service the

(25:50):
rail and the customer.
Um, I'll 97 of the carriers inthe chicagoland area.
They, just they.
They want to get a piece.
They're a piranha looking for apiece and they and they'll
shout out any price.
But we have a nice mix for areason, right, fifty-some-odd

(26:15):
company drivers and 145 motoroperators or whatever.
I've always had that nice mix.
When you go into downturn.
You know, maybe some of theowner-operators that aren't so
good haven't been following thesafety as good.
Blah, blah, blah.
You know they need to be.
You know, let go Cold Huh.

I was saying cold like let go.
Yeah, that works.

Yeah, you never want to do that, I mean right,
but I mean you have to beflexible.
Uh, I've I've learned one thing, and that is expect the
unexpected, uh, and, and you'restill not even prepared for it.

so so you're speaking my language there's.
There's so much gold in whatyou just said.
Um, I don't even know where togo with it, but I'll start with.
I can certainly appreciate yourfocus on transparency and also
the idea that you can't controlhow vendors, customers,

(27:16):
warehouses are necessarily goingto play.
They get to make the rules totheir own game and it's your job
to either agree to those rulesand play the game or or not.
You don't have to, but choosingto just be transparent about
those rules is the only way todo it, and whether it's putting
a note in about there's nobathroom, so go to the bathroom

(27:38):
ahead of time, or you know wherewe used to run into a lot was
like detention things and myphilosophy was like, yeah, I
want to pay driver's detention ahundred times out of a hundred,
as long as it's deserved, aslong as they were on time and
they did what we agreed to.
If we said, you know, if the,if the facility pays after two
hours and that's what we agreedto then pay them after two hours
.
But there were some facilities,produce locations and such that

(28:01):
didn't want to pay at all, andthere were some facilities that
we'd said, okay, you know whatthey're not going to pay.
We'll agree to pay after threehours, and you know what you do.
You put it in the notes, yousay it, you speak it to the
company before you agree to theload, and they agree to it or
not.
And the worst case, though, waswhen they wouldn't listen and
then they wouldn't read thenotes.
Listen and then they wouldn'tread the notes, and then, after

(28:22):
the fact, they'd be like why amI not getting detention after
two hours?
And it's like, well, this iswhat we agreed to on the load.
Like, if you needed more money,you should have put it in the
in your, you know your, yourline haul rate on the front end.
I can't control how everyoneelse behaves.
All I can control is how Ibehave within the rules of the
game, and then I communicatethose rules effectively to

(28:43):
whoever I'm working with, andthat's just to me.
That's, that's freightone-on-one, and and
unfortunately, it's adifferentiator.
It really probably shouldn't be, but I think guys like you and
I wouldn't have been able tobuild businesses the way we did,
or if if there weren't so manyplayers that didn't operate that
way.
To give you something to bebetter than.

Right, so and and and you said it right there.
I don't know how many times Iheard a driver tell me I was in
line, waiting at the window for15 minutes, and then they
punched my thing.
It was seven, oh one.
We have a you know agreementand obviously we not if you work
with a broker or somebody thatyou don't work with on a

(29:27):
consistent basis.
But we have an agreement of a15-minute leeway, right, we
would rather them be 15 minutesearly than 15 minutes late,
obviously, but what we do iseducate the driver.
You want to be paid, you want todo all these things?
Well, guess what?
Someone at that dock is waitingfor you to load your container

(29:47):
at that time that you agreed tobe there, and so you need to be
there before that.
And I don't want to hear thatyou waited 15 minutes in line
before they could get up to thewindow.
If you know that, you shouldeither tell us that you're there
and you're waiting in line andwe pull up your GPS and send the
message to the customer.
Right?
This business has always beenabout communication.

(30:08):
99.9% of anybody's problems isa poor lack of communication,
and you know what I get in mylife all the time Poor lack of
communication and I think, onlybecause I demand better
communication and I just.
You know you don't ever getwhat you want, but you take what
you get.

It is the way to win, though I mean it's it's a
simple concept Can be hard toexecute because you know people
got a lot of things there.
You know the average rep isprobably navigating 10 or 15
accounts, or in your case it's20 or 30 drivers, whatever it is
.
So I get how things can be lostin the shuffle and a chaotic
business, but you know all.
So I get how things can be lostin the shuffle in a chaotic

(30:47):
business, but you know all youcan do is set fair expectations
and try to hold people to them.
I am curious, though.
You know you made a commentaround be less hypocritical.
We talk about that a little bitand like what?
Just your leadership style ingeneral.
I want to get into Matt, mattthe leader, for a bit.

Yeah Well, I've never asked anybody to do
anything that I wouldn't do, soas far as that goes, I'd
probably, you know, a hundredtimes more hands-on than your
typical, you know, CEO.
So what was the?
What were we looking for here?

I was asking about your leadership style.
I mean, you mentioned to beless hypocritical and I'm just
as a guy who grew up or workedas a driver, so you've done the
job, but now you became a CEO ofa pretty large company.
You've obviously been verysuccessful and I'm just curious
how you go about leading.
You mentioned transparency.

You mentioned your two theories a man on the person
like michael michael jacksonsaid, it starts with the man,
the mayor, and what I mean aboutthat is I can't, I can't tell
drivers to do the speed limit.
If I'm not going to do thespeed limit in my car, right, if
I'm going to drive reckless inmy car, then I, I can't, I
shouldn't be, be, uh, the ceo ofa transportation company,

(32:05):
because you should expect thesame thing from yourself as you
would your drivers or yourdispatchers and the dispatchers,
like we talked about, if you'vegot a facility where you're
sending a driver in, don't nottell him because you think he's
not going to want to go.
Tell him everything youpossibly can so he understands
what he's signing up for.

(32:25):
That way he can't go oh, thishappened or that happened, blah,
blah, blah.
You're like, well, you know Ikind of filled you in on.
You know some of the nuances ofthe facility, but that's I mean
in your everyday life of being ahypocrite.
You can't, you shouldn'tcriticize people, which I've
spent my whole life and it'sinbred into me.

(32:46):
You criticize people but you'reno better, right, you just need
to be better.
And if you're not going to fixthe situation, then don't talk
about the situation.
Or if you're going to talkabout it.
Talk about resolution insteadof just word about it, right,
instead of just worried about it, right?
You know, successful people aresuccessful because they solve

(33:10):
problems, they solve issues,they solve solutions, they
communicate.
Otherwise you can't.

Yeah, I mean that all resonates with me.
It's funny because you remindme of a story with one of my
owner operators.
You know I was a carrier rep.
How old I'm?
35.
I guess 17 years ago for a fewyears and just loved it.
I worked mostly withowner-operators just because
they were more fun to deal with.
And there was a gentleman,peter Achukwu, and his wife

(33:41):
Catherine was his dispatcher.
They were from Nigeria, theyhad emigrated to the States,
they lived in Marietta, georgia,and this guy used to run all
over the Southeast for me onthese coke loads and whatever.
But I used to do these companymeetings at Molo where every
couple of weeks I'd bring Iwould usually be the speaker but
I would just talk to the teamabout whatever was on my mind

(34:02):
and sometimes I had guestspeakers.
I brought a shipper in and Iwanted to bring an old driver
and so I brought Peter in and wehadn't done a load together in
10 years but we're still friendsand I just asked him to talk
about you know why we weresuccessful together and like
what he appreciated about ourrelationship and what he said to
our whole team was he was likethe reason that I would always

(34:22):
work with Andrew and why Iappreciated our relationship
more than other brokers isbecause, no matter what, he told
me the truth about a load andhe would sometimes call me and
say, listen, peter, I need youto go pick up this load at Coke
in Atlanta and I know you hatethe place because this one
facility was really tough andthe person who ran the facility

(34:43):
was not necessarily nice topeople and and he knew we were
going in without an appointmentand he was going to be waiting
for a while to get loaded.
But he's like I just loved thatyou didn't hide that, you
didn't like avoid telling me it.
You didn't say that it was afirst come, first serve.
You told me straight up thiswas a work and we were going to
be waiting for a while and wewere going to have to deal with
the person that we didn't likemaking us wait.

(35:07):
And he's like that's why Iloved our relationship, because
I never had to worry about youhiding something from me, and I
got that from what you just saidand I can certainly relate to
it.
So I think that's a lesson foranybody in our business to learn
is like there's two ways todeal with with these issues.
One is to kind of deal with itNow.

(35:29):
The other is to deal with itlater.
You deal with it now, but beingupfront with your driver and
say, hey, this is what's goingto happen and yeah, maybe I'm
paying an extra a hundred bucksor 200 bucks to someone to get
deal with.
To deal with it.
Dealing with it later is metelling the guy it's first come,
first serve, go ahead.
And he gets there.
He realizes there was a missedappointment.
Now he's pissed at me, he'swaiting and who knows what

(35:52):
happens from there.
He threatens not to deliverunless I give him an extra 500
bucks.
He never works with me again.
So you either deal with it upfront or you deal with it on the
back end, and 99 times out of100, dealing with it on the back
end is going to be way worsethan just dealing with it.

It's going to be very contentious, not good.
No, your way is much I wouldsay 100% the way it has to be
and it's fair.
I always say you know.
They always say that you knowthere's a driver shortage,
driver shortage.
You know there's always been ashortage of treating drivers
properly.
If they want to reword it thatway, that's the way they should

(36:28):
word it.
But drivers will go and they'rehappy to work at a good place
as long as it's treated fair andcommunicated to fairly.
So you know, those are thethings that we talked about,
this off camera.
Um, in my early years, you know, people were like oh, broken
serpentine belt or whatever, whya driver wasn't going to show

(36:50):
up or whatever.
I would rarely be transparent,say you know, the driver you
know had a personal problem.
We had to find a fill in.
Whatever you know, just behonest about it.
There's no reason to make upany lies about why you're not.
I always tell employees I don'thave to hear why you're not
going to be in.
You're not going to be in, it'snot going to help us and

(37:13):
whatever your excuse is, it'snot.
It's not going to benefit meeither.
I mean, if you're not here,you're not benefiting the team.
That's all that matters.

So yeah, the other thing you said I wanted to
hit on was around judgment ofothers or criticism of others,
and it reminded me of this is aproblem I've had and, you know,
I think I could.
I think I could look at mytenure as CEO at Molo and see
the hypocritical behavior attimes where, you know, I preach

(37:40):
the importance of treating ourpeople well and treating each
other well.
And then my emotional reactivityled to, you know, me blowing up
at an employee because wescrewed this up or that up, and
it wasn't necessarily theirfault, but I was just too
emotionally reactive and so likeit was certainly hypocritical,
but in in in now, years oftherapy I've, I've been, I got a

(38:01):
good lesson and that lesson wasour judgment of others is a
reflection of how we feel aboutourselves and that is something
that has really hit home for me,because you know whether it's a
judgment that's like somethingsignificant of you know someone
screws something up and you'relike this person's an idiot, or
or it's like little things Imean little micro judgments when

(38:23):
you're just, you know, walkingyour dog and someone else is
walking their dog the samedirection as you and it you
realize that's going to makeyour dog, you know, act as act a
fool and you're like, why isthis person walking?
I mean it's a stupid thing toget upset about, um, but my
point is just, I think it's.
I think being a little moreintrospective has helped me
realize like these judgments Ihave are are not really about

(38:45):
the other person as much as theyare about, maybe, insecurities
I have about myself or, um, justthings I feel about myself that
that need need work.
So I don't I don't know ifyou've ever heard that saying,
or if or if you can connect toit at all or relate to it.

Well, I do.
I, I believe everybody that Icome in contact with uh, you
know, helps make me a betterperson.
Uh, whether they're a betterperson or not, um, you know, I
find it sometimes it it the moredifficult people or more
difficult customers for me are,the better customers for me to
deal with.
Uh, only because I understandthat there you know things that

(39:23):
they go through.
Like I get 900, you probablyhad the same thing, but you get
900 emails a day of nothing thatyou want.
And you're lucky if you get oneemail that you're looking for a
day right, I mean, we alwayscelebrate the little wins, you
know, getting a new lane, a newcustomer.
We don't have a gong to bong,but I mean, you know, if we did,

(39:48):
then everybody would be runningto it all the time.
It's you know, and I rememberlistening to I read a LinkedIn
post of yours about COVID andyou know I've been thinking
about the.
You know COVID, and it was ascary time here because you know
, you guys, as freight brokersand everything, you're not

(40:09):
really right on the ground andeverything.
And in the beginning,everybody's.
You know, oh, you know, no, no,masks aren't needed, because we
didn't have any masks Because,you know, china was too busy
filling China's orders of masks.
So I was around and everybodyhad you know, given out bandanas
or whatever right, and then itbecame mandatory that you
couldn't go anywhere without amask and it was, like you know,

(40:31):
now that you have masksavailable, so you've got to buy
them.
So that was a multi-billiondollar business brought up right
out of COVID, right, all the PEstuff, the PE stuff.
So, um, as your point is, uh,some of our, our capacity is
spot market, right, you know,that's just the way it is.

(40:57):
Uh, we do spot market and wehad, you know, contracts and and
you're, you're, you're in,you're on contracts with people,
um, but what I've really foundnow, uh, last two weeks, a lot
of things are getting held up onthe rail, no pickup numbers
because of customs issues.
Nobody's really talking aboutit right now, but it's going to

(41:17):
be a thing where things beforewere clearing a lot easier,
right, I mean, uh, but now a lotof customs issues that we
weren't experiencing until thelast two weeks.

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So I don't know segue into thatbut yeah, no, let's, let's segue
into that.
I'm curious, I wanted to getinto that, so I appreciate you
bringing us there.
It's always easier when theguest does the segue for me, so
I don't have to get creative orbe awkward.

(42:44):
But yeah, you know, from whatI've seen um online on on
twitter and and linkedin andsuch, it looks like we're
getting to the tipping point ofa massive fall off for imports.
And you know, then, railactivity, intermodal activity,
have what are you seeing?
Boots, boots on the ground.

(43:05):
Have you seen that or do yousee it coming?
What has business looked likein the last kind of three months
?
Was there a big pull forward ofinventory being brought in to
avoid the terror of chaos?
Or talk to me a little bitabout that.

Yeah, so that's the first thing everybody was
talking about when Trump waselected, right, was you know?
We want to pull all thisforward and I'm thinking there's
not enough time, there's no way, there's not enough time.
And then I reverted to hisfirst term and the same thing,
if you remember, happened.

(43:40):
Right, I got a short memory,tell me.
Well, they pulled the importsforward again.
Did he threaten tariffs thefirst time around?
Yeah, I got a short memory Tellme.

Well, they pulled the imports forward again.
Did he threaten tariffs?
The?

first time around.
Yeah, yeah, but he didn'tfollow through on it.
No, he didn't.
Biden left some of them inplace, got it, but in any event,
we didn't experience a ChineseNew Year, okay.
We always experience a Chinese.

New.

Year.
Yeah, chinese New Year is thesecond through the fifth.

It starts and goes two weeks and it generally
affects our business for aboutsix weeks, right, and what is it
?
A shutdown for four days therethat leads to weeks of impact
here, I think it's more thanfour days.

It's usually when people leave their job and go
start.
You know, when they come backfrom holiday or whatever, they
go back to another job or adifferent job.
I don't know how it all works,or whatever, they go back to
another job or a different job.
I don't know how it all works,but I used to tell you that it
was always march and april.
Right, we were looking for seedloads, firework loads and all
that to to make up for thosetype of things, because that's

(44:37):
when you know, we get the hybrid.
Seed loads would come in,firework loads start right after
the first of the year.
Talk about firework loads too.
If this doesn't resolve out,nobody's, everybody's gonna be
uh having drone, uh fireworksthis year, because fireworks
come from china.
So, um, you know, maybe trumpwill take them off the list, I

(44:59):
don't know, but in any event, uh, yes, I feel like they did pull
it forward.
I feel like there was noChinese New Year.
I don't know.
I'm not going to say this.
From my point of view, this isthe Chinese New Year now.
Right Now, they've shut down.

(45:19):
We normally experience aslowdown.
We haven't.
I know everybody on the portsare talking.
We do a lot of crosstowns.
Uh, we move east coast uhrubber wheel containers to the
west coast rails and west coastrubber wheel containers to the
east coast, uh, so we go in andout of the iowa interstate csx

(45:40):
ramps, the ns ramps, the cpramps, the bn ramps and the CP
ramps, the BN ramps and the UPramps, just doing cross towns,
making connections.
Those had not slowed down.
We're still experiencing thesame volumes.
We were really leaning on fiveor six quarters to last quarter

(46:03):
of last year, fourth quarter of2024, things started looking
better.
Uh, this first quarter was, uh,booming great first quarter.
Second quarter in the year wasgoing to look great right.
Um, so we don't know, wehaven't.
Uh, I feel like last time I dida podcast was with Paul Paul.

Paul.

Yeah, and that was whatever 30, 32, 30 months ago,
whatever, before it dropped offthe first time, right?

Oh man, are you an indicator?
Are you a tipping point?
I don't know.
On your podcast, oh God, I hopeyou and I don't uh send send
the imports off or uh drop off,uh the freight so, uh, everybody
, you know the sky is falling.

I do know we haven't experienced it.
Uh, it's may 1st.
I grew, uh, I spent some timein Hawaii, so it's May Day.
I remember May 1st in Hawaiiwhen I was 12, I was wearing a
tea leaf skirt and doing hula.
Today, because it's a big thingin Hawaii May 1st, oh, wow,

(47:16):
that's a big deal.
I didn't know that.

I learn something every day.
Aloha to all my Hawaiianfriends Aloha to our Hawaiian
audience.
I will, after we are donerecording, I will check how many
listeners we have in the stateof Hawaii.
I can see that stuff.
I can see where people listen,so hopefully we get a few after
this episode.
When all your friends see thatyou're on the show, yeah.

Well, all my friends from uh uh, kielike or
Kamaaina, I mean uh.

I'm not, I'm not going to try to repeat those,
those words, but uh, orlocations, Um, I'm curious, how
does, like you know, when yourteam boots on the ground, or
your drivers I'm sure they payattention to what's going on in
the media, Um, and they see, youknow what looks like the sky
potentially falling in the nearterm.

(48:06):
How do you kind of navigatethat as a business, Like as a
leader and as the CEO, how doyou think about communication
and what kind of operationalchanges you might make if there
is a big fall-off coming?
How do you kind of navigate it?

fall off coming.
How do you kind of navigate it,uh, okay, well, we were.
We were constantly hiring newdrivers.
Since january 1st, we wereputting on maybe two drivers a
week.
Okay, uh, it was maybe threeweeks ago.
I, I asked diana to pause.
I don't even know hires, eventhough we have a list, uh, for
company drivers and owneroperators.
Just ask her to pause, uh,because that's the first, the

(48:51):
best way to piss off yourcurrent drivers that keep hiring
drivers in a downturn, right?
So, um, uh, we sent a blast outan email to all the drivers
that not make any unnecessarypurchases.
Advise them to pay attention tothe news Again, you can't just

(49:13):
be transparent with yourcustomers, you have to be
transparent with everybody inthe industry, 100%.
Sometimes, when you'reover-transparent, then people
obviously then worry more thanthey should.
Right, stress comes from theunknown and then when people
don't know, then they'restressed out.
Um, I always like, take it dayto day, right, because you know

(49:37):
from being in business that, um,it's.
It could be like uh, youremember the gilligan's island?
You go on a two-hour tour andyou could be end up on an island
, right, you've never heard of gGilligan's Island.
You go on a two-hour tour andyou could end up on an island,
right?
You've never heard ofGilligan's Island.

I've heard of Gilligan's Island and I've
certainly seen an episode or two, but I was probably 10 years
old so I can't.
The reference is hard for me torelate to well, but I do
understand what you're saying,yeah well, you don't know what
you're in for.

Right, the day could start out and then you
know it could just turn into anavalanche of shit.
Um, you know, or you could havea good day and everything goes
well and everybody's happy andupbeat, like every day here at
whimsy yeah.

So so your point is, you know, lean into
communication to everyone, yeah,and be cognizant of the fact
that, yeah, I mean uncertaintydoes create fear, because I've.
There were a couple instanceswhere I remember leaning extra
hard into communication, and oneof them was at the beginning of
COVID, um, when I was callingit.

(50:39):
I remember my I still haveformer employees that give me
shit Cause I was calling itCOVID, um, I mean, we just
didn't know anything about it,but I do remember one of the
things I said was listen, let'sjust focus on what we can
control, which is our serviceand execution for our customers.
This feels like something thatno one will ever forget, so
let's make sure that they don'tforget the way we took care of

(51:00):
them.
Focus on what you can.
And then the second thing waswhen we were selling the company
and six months in advance, weknew we were doing a deal, but I
thought we were actually goingto do a private equity deal.
I think I remember telling myteam I was like we're going to
go raise a bunch of moneybecause we think it's the right
time and there's like a 90%chance we'll do it through

(51:20):
private equity, but like 10%chance it's a strategic partner.
But we were like let'scommunicate as proactively as
possible with people so theyknow.
And for that six months I keptupdating people, even the point
of letting them know we werebeing acquired before it was
done with a publicly tradedcompany.
We just had to be careful aboutwhat we said.
But my thought there was kindof to your points like, okay,

(51:41):
this me telling them is going tocreate some fear and maybe
they're going to be people whoproactively quit or take another
job because they're worriedabout what will happen.
But I'd much prefer I'm the onetelling them all along the way
versus the day it happens.
There's a news article sayingthat Molo's been acquired and
they haven't heard a word fromme.
I just feel like I'd rather ownthat narrative and be the one

(52:06):
communicating so they knowexactly what I'm thinking, why
I'm thinking it and why we'remaking the decisions we are,
because at the end of the day, Ithink it's so much easier.
Something I've learned is it'sso much easier for us to have
compassion for others than it isfor ourselves.
And that's just a general point.
But specifically to this, Ibring it up because when we

(52:29):
communicate effectively, peoplerealize we're human and they
realize.
Listen, you might be the CEO,but you're just like a lot of
other people on the team,showing up every day, trying to
do the best you can with whatyou got.
And yeah, you've got a biggerweight on your shoulders because
you're making decisions onbehalf of 200 drivers and all
your employees.
But when you're communicatingproactively and transparently,

(52:51):
you're proving that like you'rejust doing what you can with
what you got.
You're sharing, you're makingdecisions based on the
information you have and doingit with everyone's best
interests in mind, and that's,you know, that's our job as the
CEO right?

Yeah, you would hope so.
Right, and not always the case.
You're, uh, you're, a diamondin the rough and you're not.
Uh, other people are, are, aremore deceitful.
Uh, then those things need tobe kept under.
You know, you know, but you didthe right thing.
He asked me I.
He asked me 100% all the time.
If you can be transparent,communicate things before it

(53:29):
gets out, like I always said,we're going to be late.
First call is to the customer.
Second call is the facility.
Right, you let the customerknow.
You don't want the customer tobe the last one to know anything
about their load.
I'm going to be the firstperson that knows everything
about their load, and that's howyou retain supporters.

Yeah, and just make sure that you have
solutions in mind as you go tothat customer with the
information.
So the worst thing you can dois just let them know hey, this
thing's going to be late with nobackup plan.
No, this is why or not even thewhy, necessarily as much as
this is what we're going to doabout it.

(54:12):
Whether it's this driver felloff, I got a new guy who's going
to grab it tomorrow and he'llbe there at 8 am or whatever.

Typical.
You see, all these guys postedeverything on LinkedIn what they
can do heavy, overweight loads.
All these guys postedeverything on LinkedIn what they
can do heavy, all overweightloads.
All these things.
We've been doing those foryears.
We do deliveries to Navy pair,we do Nate delivery.
We just did some deliveries tothe uh, the art Institute.
So when we do these deliveries,we generally send somebody into

(54:42):
survey, right, what's the besttime, what's what directions the
driver coming in?
We, we plot out all thesethings because in this business,
uh, you know it's gettingdifferent now.
It was a lot worse before, buteverybody's always set up to
fail and then they fail andeverybody points at the driver,
the driver, the bad driver, um,and then people want to quit

(55:05):
their jobs and, and so when youset people up to be successful
and they're actually successful,then they want to stay at their
job because they feel it'simportant that they're
constantly and and you know, ifyou're the ceo you want to you
want to see people feeling likethey're winning, whether they're
winning for you or the company.
It builds confidence in theirlife.

(55:28):
Like I always tell everybodyI'm like treat customers, your
supporters, how you want to betreated right.
It's that.
It's really that simple andyou'll get better results, right
?
You know you want.
You want to be told what's goingon with whatever.
You know first.
You want to be the last personto know.
You want to be told what'sgoing on with whatever First.
You want to be the last personto know.
You want to be treated fairly.
You want to pay a fair price.

(55:49):
If you can pay more doesn'tmean you want to pay more, right
?
I will pay more for betterservice, so I would expect that
I would get more for my betterservice.
But I always feel like we'reconstantly giving better service
than I receive in the realworld and I have to answer for
the times that we don't, andit's disappointing.

(56:12):
You know, you feel it.
You're like oh, you know, Ialways say every time the team
fails, I've failed as a leader,I failed to give the proper
support, I've failed to give theproper SOP.
You know, whatever the case maybe, so I share that failure
with my team, right?

You mentioned that you guys get into kind of
the niches and you know earlieryou said I mean you mentioned
doing deliveries to Navy Pier,the Art Institute, and that's
not your typical freight.
You also earlier in the showyou mentioned you have a knack
for making lemonade out oflemons and it sounds like a lot

(56:56):
of your business has beenfocused on kind of building
riches and niches, whether it'shazardous or overweight,
whatever it may be.
Whether it's hazardous oroverweight, whatever it may be,
I'm curious one, why did youchoose to chart that path for
your business?
And two, what kind ofchallenges has that created for

(57:18):
building the right kind ofdriver workforce to support that
challenging type of freight?

Yeah, yeah.
Well, again, we're not biasedabout any freight.
We really make our bread andbutter on volume.
Like you know, people will callus today and go.
You know, I got 20 containerslast free day.
Today.
They need to deliver tomorrow.

(57:44):
If the shipper could take them,we're going to deliver.
Right, that's where, you know,know, we're the most valuable,
but at the same time, we dooversized tankers uh, hazmat,
all the things that you talkabout and uh, we move tons of
reefers over 100, you know, 100reefers, probably 150, 200

(58:08):
reefers a um, those are thingsthat you need support for.
You need good drivers for youknow, if it's pharmaceutical or
mayonnaise or whatever it is, um, you know those.
Those are the things that youhave to be.
You have to be capable of doingit.
We can do high volume.
Uh, you know we have a lot ofcustomers that, uh, they have a

(58:31):
high volume uh product and theydon't want it pulled from the
rail until it's coming to theirdoor, right, and so they have 50
containers that have to go, youknow, over two days that, well,
not a lot of carriers are goingto be able to move 50
containers over two days, right,how is your business even
situated in a way where you cansupport such a massive like

(58:53):
influx overnight?

I mean, it's not.
You're not like brokering thatright, you're using all your own
.

Yes, we never got into brokering because I didn't
want to compete with mysupporters.
Got it.
Yeah, I see all these carriersthat have their brokerages and
all these things, and I feltlike our position in this
industry was to support howeverour customers want it right,

(59:21):
they don't want us to competeagainst them, they want us to
support them.
So that's kind of what we'vealways tried to do is just be
you know the operational end forthem, the actual nuts and bolts
, and execution right.
The hardest part of anything isjust executing.
You know, when people ask youknow, how do you get in your

(59:44):
business?
Well, you have to take theinitiative right, and then you
have to have follow through.
Initiative right, and then youhave to have follow through.
Those are the two keyingredients is a little
initiative and then tons offollow through, because
everybody's going to tell youyou're an idiot.
They say, right, it won't work,blah, blah, blah.
They give you a hundred millionreasons why you're going to
fail and you don't even knowyou're oblivious to it because

(01:00:06):
you're like I'll never fail, I'mright, right, I mean, that's
the way you're feeling.
So I always felt like if you'renot, if you're not with me,
you're against me, right, and soyou know you're either on my
team and we're going to crush it, or I don't know and you're
just somebody I used to know,because I have plenty of those

(01:00:28):
people as well, right, peoplethat knew me in the early days.
They probably wouldn't say thenicest things about me, but the
fact of the matter is 29 yearsin the Chicago intermodal market
, you don't think I've seen somestuff.
So I've got great experienceand knowledge and wisdom and

(01:00:50):
every day it becomes betterbecause I'm still willing to
learn.
I'm still learning.
I learned from my younger teampatience, understanding, empathy
, but at the same time they'reexcited about all the things
that we're doing, likeinitiatives that we have.
We have our own lifts.

(01:01:12):
We use uh.
We use ai for order entry, uh,ai for our cameras at our
facilities.
We use ai on the truck.
We got ai cameras in the truck.
So I actually have employeesthat will sit there and coach
the drivers if they see himspeeding in real time.

(01:01:33):
Oh, wow, where you know.
Uh, we're doing all thosethings in real time because I
learned when I was 16, andrew, Ihad to go to court for a
speeding ticket and the judgetold me that ignorance was not a
defense in his court and he hadthat defense.
That means you can't say Idon't know.
You have to know.
It's your job to know.

(01:01:56):
So yeah, I mean if people ask ifI would retire or sell.
I don't know how does it feelwhen you sell something like
that.
How does it feel for you?

Andrew Silver (01:02:07):
At Molo we built a great company and I'm proud of
the work we did.
We knew when to ask for help,and sometimes that meant going
outside of our own company.
I'm proud we built an ecosystemof trusted partners like
Metaphora.
When we needed differentiatedindustry expertise in business
consulting or technologyservices, we looked at Peter
Ryan and the team at Metaphora.
They've consistently deliveredvalue in the transportation and

(01:02:29):
logistics space for over adecade for mid-market and
enterprise brokers, for shippers, carriers, private equity and
freight tech companies.
At Molo we use Metaphor tosolve problems we simply
couldn't on our own.
Metaphor is the only partneryou should trust to help you win
, whether that's doing ops andtech diligence, growing revenue,
optimizing spend or selectingand building software.

(01:02:51):
Go check them out atmetaforanet.
That's M-E-T-A-F-O-R-A dot netNot good, I mean.
I think everybody's different.
There are parts of it that feltreally good.
The financial windfall was thefirst time I experienced
something like that.
I was happy with that, but Ineed to be building.
I was happy with that, but Ineed to be building and.

Matt O'Mara (01:03:14):
I missed that a lot .

But that was the plan, that wasn't to leave.
So I think that happened and itwasn't by choice.
But I also think ignoranceisn't an excuse, as you said.
So there are probably somethings I could have done
contractually on the front endof that deal that would have
protected me better.
And then there are some thingsI could have done in the

(01:03:38):
business after the acquisitionthat probably would have
protected me better if I hadjust been better, if I had
handled things better, dealtwith issues better.
I was frustrated by things thatI disagreed with and I didn't do
a good job of navigating thatin a way that made them want to
keep me much longer, which iswhy they didn't.

(01:03:58):
So you know, I think I've toldpeople I've been out for two
years and almost two months nowand the first year was a lot of
anger and resentment andfrustration and I'm glad that
has dissipated and that's goneNow.
You know I've got the show,which has been a lot of fun, but

(01:04:20):
it doesn't really fill my cupenough.
I've thought about pushing thatinto.
You know building a media typebusiness.
You know something to give ourindustry more interesting
insights from people likeyourself.
I've got the network to keepbringing guys like yourself on
the show, and you know there'smaybe other ways to leverage all

(01:04:42):
your insights into differentways for people to digest it.
Not everyone wants to sit andlisten for an hour and a half or
an hour and 15 minutes of guyslike you and I talking.
But at the end of the day, whatI'm realizing is I miss the
grind, I miss the stress.
I mean I miss feeling like yourback's against the wall.
I miss feeling accountable to500 employees that we need to

(01:05:05):
make something happen in thenext few months and grow, or
else we're not going to be ableto keep all these employees or
hire more of them.
I miss that stuff a lot and I'myoung, so I've still got the
energy and I'm playing a lot ofpickleball, if I'm being honest.
First it was a lot of golf.
I've transitioned to a lot ofpickleball because Chicago golf
weather is not year-round, but Ineed more to do and I'm sure

(01:05:29):
there are people that willlisten to this and say, man,
touch some fricking grass.
Like I would pay to be in yourposition of not necessarily
working and yeah, it was greatfor a while, but I miss it.
So that's my two cents.
I don't know how you wouldspend your time if you sold, but
probably some golf, I wouldassume.

Matt O'Mara (01:05:46):
But I'd golf myself to death?
Yeah, no, so you assume.
But I'd golf myself to death,yeah, no, so you know, people
always ask that.
You know, I never thought aboutit.
I always thought I'd just bethat crazy old guy to push the
broom in the shop.
And they're like, yeah, let'ssee, I don't kind of talk to him
, he's angry.

So he owns the place, but leave him alone.
If you talk to him, he mightmake a decision at this point.

Matt O'Mara (01:06:05):
He's 85 yeah, so I don't, I don't know.
You know that actually wouldprobably scare me then.

But after talking to you I'm even more frightened
now I mean, does it fill yourcup every day to show up to work
?

Matt O'Mara (01:06:19):
it, it does I, you know, uh gives me my purpose
yeah, talk to me about that.

What, what about it?
What about it fills you up?
What about it gives you purpose?
Uh, just you know um.

Matt O'Mara (01:06:29):
What about it gives you purpose?
Just, you know, seeing everyoneinteracting with everyone.
Coaching I do a lot of coachingnow.
You know that's rewarding.
I never had a mentor.
I always had people I looked upto, but I never had a mentor.
So, you know, I would like tomentor some, you know some young

(01:06:55):
people, and that's what I'mdoing here and that's important.
I, you know I don't know howthat is for you I get asked to
be on boards and stuff at allthe time and I'm like you know I
don't want to sound, you know,like you know, I'm all whimsy,
right, if I'm going to spendtime, I want to spend time with
a driver dispatcher.

(01:07:15):
You know I, I go up with guysand play golf on the weekends.
I'm all.
I'm all in on my business andmy people, you know.
So when we have meetings, it'sgreat to see you know the
drivers.
I don't, I mean we have.
It's great to see you know thedrivers.
I don't, I mean we have.
It's.
It's disgusting.
I got like 40 care packages inthe other room for drivers for

(01:07:38):
driver appreciation week andthey just never got here a
paramount prospect and we didn'tobviously do a good job getting
them delivered to them.
Um, but uh, you know, at thesame time, I I want to celebrate
drivers every day, not just oneweek, because I, you know, I
was a driver, I am a driver.
Um, a lot, a lot of peopledon't understand.

(01:07:59):
Uh, you know, it's likeanything else you do in life.
Or if you're sacrificing timeaway and you're at menlo, well,
those are you, that's your workfamily, right?

So you have a work family and then you have a
normal family, and then so, uh,that would be like losing part
of my family yeah, I mean, Iresonate with everything you
said because I think, ironically, one of the things there's two
things I missed, probably themost um, one of which was the
little interactions with peopleevery day.

(01:08:30):
They didn't have to be thisgrandiose.
Let's sit down for an hour andlet me teach you how to be great
.
None of that nonsense, but justrunning into people as they're
doing their job and just givingthem a little bit of support and
seeing that they appreciatethat, letting them know that you
know that Smithfield or Krogeror Aldi really appreciates them.

(01:08:54):
Like when I would get notesfrom those customers saying, hey
, you know, taylor Krug is astud, he's killing it on my
business.
And I could go tell Krug hey,krug, missile, you're crushing
it.
I just heard from Smithfieldthey love you.
And like the smile you get fromthat like those are the things
that I missed.
Those are the things that fillmy cup being able to create like
I always thought we didn't,like people would be, like you

(01:09:16):
created so much opportunity forus.
It's like, dude, we, we openedthe door and you had to run
through it.
And like you did all the work,you deserve all the credit I
miss.
I miss that Like I miss that alot.
The other thing I miss that alot.
The other thing I miss isselling and being in front of
customers and feeling like youknow, I think that a CEO who

(01:09:36):
hasn't sold is never going to beas good as a CEO who has, who
hasn't sold for their supper,because you just you have to
know how hard it is to actuallyput the food on the table.
I don't believe in anyone who'sgoing to set expectations for
people if they haven't done thatjob.
And to have a CEO who comesfrom a finance background and
they're like we need to hitthese numbers, we need to grow

(01:09:57):
by 30% this year.
It's like, bro, you've neversent an email 40 times in two
years to someone and not got asingle response until the 41st.
You've never called someone 15times over the course of six
months and been hung up on 14 ofthem before they finally gave
you five minutes of their time.
So don't talk to me about 30%growth until you've sat in that

(01:10:21):
seat and done that, and that'sjust my take.
But I missed that.
That is what got there.
Like you mentioned, you knowyou get a hundred emails that
you don't want you get.
You know, maybe you get oneemail you want.
There was nothing I loved morethan seeing that email come in
as a response from from apotential customer who I'd
reached out to and, like that,caught me more excited than

(01:10:43):
anything, and I missed that alot, right right, you have
supporters, customers.

Matt O'Mara (01:10:50):
when they give you the gratitude, you have to share
it with everybody, becauseeverybody's sharing this shit,
right?
Oh man, we shit every day, allday long.
So to get back to that, though,I yeah, I always say I'm a
whale hunter, right, I kill thewhale, and then everybody's got
to dice that thing up.
So we're, you know, know,probably not the best thing to

(01:11:13):
say for peter, and I'm notkilling any.
I'm not killing any, it's ahypothetical whale.
I'm killing or slay a dragon.
You know, I have a couplecustomers that I always tell
them I go, I don't care how bigand nasty and how much fire he
shoots, you know, I'll slay adragon for you.
It doesn't matter and actionsspeak louder than words.

(01:11:35):
A lot of my young Zs they don'tknow isms, so I make them tell
me isms all the time and I givethem isms that they've never
heard, because you know, that'sjust.
It creates a smile.
Yeah, you know, those are thekind of things that make it all

(01:11:55):
worth it, right?
You know, everybody acts likethe business is so bad and it
rags you out.
And it only rags you out is ifyou're not properly preparing
and constantly adjusting.
Properly preparing andconstantly adjusting, doing the
necessary things to keep thepain away or keep the pain at

(01:12:17):
minimum.
So you know if you're not doingthe proper things, like
everybody's asking me.
You know what do you do aboutthe terrorists and this and that
you don't know what happensuntil it happens, right, if I'm
correct and we're going throughthe Chinese New Year, we're
going to have a part of May andpart of June.

(01:12:38):
That's going to be slow, right.
How long it takes, I don't know.
I never thought it was abouttariffs.
Everybody thinks it's abouttariffs.
Everybody thinks it's abouttariffs.
It was really about Chinawanting to get the yuan this be
the dollar traded across theworld.
Right, that's what we'refighting for now.

(01:12:59):
It ain't nothing about it.
You know, they've been robbingus of our peas, everything for
years, and everybody went alongwith it.
You know, and I don't want wantto say nothing, but it seemed
like the other side was in withyou know, whatever side that is,
but the last thing we wantdangerous waters, you're
chartering I, you know, I justwant freedom and liberty, like I

(01:13:23):
was told and, and thiscountry's given me all of that,
and I'm very, uh, appreciativefor the state of Illinois and
this country and everybodythat's in it.
So it's my duty to defend thiscountry.
For no other reason, it's forthe fruits that has brought my

(01:13:43):
family and all my many familiesconnected to me.
I think the world's way toomore entitled and it should be a
lot more appreciative of thelittle things that you do have.
Right Started appreciating thelittle things and then you know
you can graduate to appreciatethe better thing, bigger things
in life.

Yeah, I mean that comment and the one you made
before about you know running abusiness and how you know.
essentially, what you'reinsinuating is perspective, is
everything and perspective isreality perspective is reality,
perception is perception isreality but perspective, like

(01:14:24):
you know, you talk about gettingso stressed out and and when I
think about my tenure as a ceo,it's like there are times where
I was very happy and like my cupwas filled every day with the
little things, like I said.
But there were also times whereI was miserable and I was angry

(01:14:50):
, know, emotionally immature andand, frankly, like I, just when
I look back at it, it's likeit's it's all in our control to
make the decision of how weperceive the world and how we
perceive our situation.
You and I were both and areincredibly fortunate to have the
positions we've had.

(01:15:10):
You have, I had, with anincredible workforce of people
who show up and bust their buttevery day to make our businesses
great.
And, yeah, if you just focus onthe five emails you got with
issues and you let those issuescloud how you see the world,
you're going to be angry, and I,you know.

(01:15:31):
I just started reading this bookit's in my hand now because I
wanted to read this quoteEmotional Intelligence and it's
like the first kind of quote inthe book from Aristotle Anyone
can become angry, that is easy.
But to be angry with the rightperson, to the right degree, at
the right time for the rightpurpose and in the right way.
That is not easy and it justshows the power of managing your

(01:15:53):
emotions in a way that allowsyou to be very in control.
And, you know, anger is not abad emotion, it's a natural
emotion that we all feel.
But how you navigate anger, howyou navigate stress, that's
what matters.
And to be, you know, anexplosive angry person who comes
down on their team all the timebecause little issues left and
right, that's what matters.
And to be an explosive angryperson who comes down on their
team all the time because littleissues left and right, that's

(01:16:15):
who I was at times.
That's a bad leader.
But to be someone who allowsthemselves to feel anger and
then navigate it in anemotionally mature way, where
they don't just spout off andrealize like okay, these issues
happen, well, let's take abreath, let's figure out what
the solution is like you pointedto earlier, successful people
are people who focus onsolutions, who create solutions,

(01:16:36):
not people who, just you know,get stressed out and blow up and
create more problems forthemselves, whether it's
resentful employees who don'twant to help them or customers
who see the dark side of themthat they don't, you know, want
to do business with whatever itis.
You know, just it's I.
These conversations, especiallywith strong leaders who really

(01:16:57):
run successful businesses, Ialways point me back to
realizing like we are always incontrol of our perspective If we
, if we, if we have thefortitude to be, and doing so in
a mature way, is the differencebetween being a good business
leader and being a bad one.

Matt O'Mara (01:17:15):
Yeah, well, you know that's something they don't
teach in school.
So I don't know if you're a badleader of your just first time
leader.
Okay, cause I felt the same way.
I was the same way theday-to-day grind.
You want to be a great person,you want to be a good person,
you want to do all these things,but you let all this build up
on you and then you react.
Like you said, I would like tosee him teach three things in

(01:17:38):
school emotional intelligence,common sense and self-awareness.
You teach every child that andwe're going to have a world
that's crushing it, right?
I mean, those are the mostimportant, I feel, and you can
then decipher all the thingsthat come at you on a daily

(01:17:59):
basis.
So I wouldn't say you're a badleader, because that would make
me a bad leader because I behavethe same way Very reactionary
and that's because we weren'ttaught, uh, emotional
intelligence.
You have to either learn it ordon't right, you learn it from
interaction in the world, uh soand and self awareness.

You learn it through self-awareness.

Matt O'Mara (01:18:23):
You have to be willing to look in the mirror.

But I'm just.
You know, the only reason I'mable to say the things I am is
because I was willing to look inthe mirror.
I could have ignored it all andbeen like screw you, I'm a
great leader.
I built one of thefastest-growing companies in the
world.
I can say that.
I could say I, I, I, me, me, me,I did this.
Look at the numbers, you'rewrong, I'm right, but it's

(01:18:51):
probably are true.
But I think it starts with theself.
You can't get to the emotionalintelligence if you don't, as
you said, go to theself-awareness first.
You have to be willing to lookin the mirror.

Matt O'Mara (01:19:00):
Yeah, it's enlightening when you do, when
you do Like I said, I feelhappier than I ever have in my
life when you can be transparent, say all the things that you

(01:19:24):
want to say, obviously withingood taste or whatever the case
may be.
But it's very liberating for menow, like, I get frustrated
when people can't tell me howthey really feel.
That's that's just uh, that'svery depressing for me.
You know, if you, you can'ttell me an honest feeling I'm a
grown man, honest feeling.
You know, when I, when Ifinally meet people, they're
like oh, when I first met you, Ididn't like you, you know, and

(01:19:44):
it turns out you're a nice guy.
Well, I was always a nice guy,right?
I mean, obviously my firstimpression wasn't good, right?
Then I had other people like oh, you know, you scare me.
I'm like oh, I'm like 5'10".
I'm not even that tall.
Why am I scaring you?
You know, and I guess you know,I'm like the mean mug.
Yeah, or I have this like DarthVader aura when I walk into a

(01:20:06):
room.
So, but no, no, no, so, um, butno, I'm just like you, right?
I love pickleball.
You know, I love playing golf.
Uh, these are things that Ienjoy.
Um, I love freight, I lovebeing in the business.
Do I get my, you know, do myass handed to me?
Yeah, I, you know, I, I go homeall the time, you know, wow, I
was um, but you know, then wemake up an ism and we make up a

(01:20:29):
saying, or we go hey, rememberthat time when this happened, or
, you know, that's part of life,just living over here, you know
, where.
You know, I hope to someday belike Han Solo.
You know, maybe I'm movingfreighters from Mars to here or
something, I don't know.

That'd be great.
Yeah, I would love to see that.
Well, listen, this has beenawesome.
Um, I don't know if I've gotanything left for you.
Um, anything else you want totouch on before we go, other
than you and I need to commit toa golf around a golf in the
near term yeah, that'd be great,do you?

Matt O'Mara (01:21:07):
you have a handicap .

It's not good but I'm a 16-9 right now.
I did just make the playoffswith my member guest in Cabo
with my partner.
He carried us, but we made theplayoffs.
It was fun.
Alternate shot shootout we camein fifth place out of like I
don't know 70.
There were 11 flights of sixteams, so 66 teams Not bad.

Matt O'Mara (01:21:33):
Would you say you learn a lot from playing golf
with somebody.

I think you can learn a lot about a person from
playing golf with someone, andfor a long time I was someone
that you learned.
I was a very angry person for awhile.
Um, to be a bad golfer and anangry golfer who like breaks
their clubs is just stupid.
And I say that as someone whois looking in the mirror and was
that person.
I've developed a way morecarefree approach to it, because

(01:22:01):
it's a really hard game andit's not something you just get
good at by playing all the time,which is another thing I think
some people maybe can get better.
I mean, you can improveincrementally by playing a lot.
But as someone who had a bunchof free time and played a ton,
my handicap dropped from like a21 to 16, 17,.

(01:22:22):
But I still suck in my mind andyou need to go get help.
You need lessons.
There's a lot of things aboutmy game that need to improve.
That's why I'm playing a lotmore pickleball, because
pickleball I just startedplaying and I've gotten really
good just by playing a lot.
And it's just.
You got good hand.
I had a hand coordination.
Yeah, I got good hand.

Matt O'Mara (01:22:42):
I, I got good hand I so when I was a kid, ball with
my dad all the time at the Y onNorthwest Highway, and you know
that's just that little hardball.
You ever play handball.
So I played I've never playedhandball, yeah.
And then racquetball and nowyou know pickleball.

(01:23:03):
So yeah, you learn.
I always like to go out andgolf with somebody because you
really you know you get a goodfeeling for that person, right,
how they're at a kid, whatever.
For me, when we talked aboutthat, you know I'll be a better
person Driving home.
I let everybody in front of me,right?

(01:23:25):
I go into a building, I openthe door for people, I open the
door for people, I'm going outof my way.
But naturally, just to be thatway, right, you have to set an
example all the time.
You can cry about this person,that person, but if you're not
constantly working on yourselfto be better, you're not going

(01:23:47):
to get better.
So, yeah, I like to spend alittle time every day trying to
focus on how I can be less of ahypocrite, better leader, and
being a better leader just goeswith it.
You said at the beginningsupport, encouragement, those go

(01:24:07):
a long way.
And then I don't do it enoughto show your gratitude.
Hey, I know I find now nobodygave a shit, right.
When I was younger and I wasbusted in the business, somebody
said hey, you know you're doinga great job.
You keep up and keep it upthere.
You're so stupid.
The trucking business isterrible, blah, blah, blah.

(01:24:27):
And now I get yelled at if I'mnot giving out enough accolades.
So that's another thing.
Right, I have to constantly go.
Hey, thanks, I appreciateeverything, you know.
You know, business in may or maynot drop off.
You know, like I said I'm I'manticipating May, june, chinese
New Year, otherwise there's notgoing to be a lot of stuff for
the kids to go back to school,or it's all going to be a lot of

(01:24:49):
stuff for the kids to go backto school, or it's all going to
be from indonesia or, you know,bangladesh or whatever.
And and that's scary, right thethe world and I don't think is
that are going on right now withuh, pakistan and india going,
you know having a you knowborder dispute or whatever
they're doing over there.
That's, that's scary.

(01:25:11):
You know what's going on in theworld.
We need more people to uh haveless hate in their heart.

Yeah, that's a topic for another day, um, but
I'm with you.
It'd be great if we couldfigure that out.
Um, listen, this has beenawesome.
I really have enjoyed havingyou on.
I usually ask people at the endfor some advice they'd give,
but you just gave it in the lastfive minutes and it was really
good sound advice for how tojust be a better person, not
just better leader.

Matt O'Mara (01:25:42):
Yeah, don't eat yellow snow.

Don't eat yellow snow.
We'll end with that.
Don't eat yellow snow, Listen.
Thank you so much to ouraudience.
This was a great episode.
I'm sure you all know that.
If you've gotten to this pointand if you want to learn more
about Whimsy, reach out to MattO'Mara on LinkedIn or find him
online Whimsyintermodalcom.

(01:26:06):
Whimsyintermodalcom for allyour Midwest intermodal needs.
Thanks, Matt.
Thank you, Andy.
Great talking to you.
Appreciate it.
Have a good one.
See you guys.
Thank you.

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The Breakfast Club

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.css-14f5ked{margin:0;word-break:break-word;display:-webkit-box;-webkit-box-orient:vertical;box-orient:vertical;-webkit-line-clamp:2;overflow:hidden;}Ep. #65: Matt O’Mara, CEO & Founder, Whimsy Intermodal

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.css-r6mb8g{margin:0;word-break:break-word;display:-webkit-box;-webkit-box-orient:vertical;box-orient:vertical;-webkit-line-clamp:1;overflow:hidden;}Amy Robach & T.J. Holmes present: Aubrey O’Day, Covering the Diddy Trial

Dateline NBC

The Breakfast Club

All Episodes

Ep. #65: Matt O’Mara, CEO & Founder, Whimsy Intermodal

Amy Robach & T.J. Holmes present: Aubrey O’Day, Covering the Diddy Trial