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Most pilots dream of smooth 10,000-foot runways.
Tyler Flagg trained to land a 30,000-pound aircraft on a 25-foot dirt strip… in total darkness.
After 9/11 changed his life trajectory, Tyler went from zero aviation background to flying Special Operations missions around the globe. With minimal information and maximum responsibility, he deployed into multiple combat theaters — moving elite teams into places most people will never see on a map.
In this episode:
This one is raw, honest, and packed with perspective.
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Pilot to Pilot Podcast is your go-to destination for aviation inspiration, insight, and real talk from the cockpit and beyond. Pilot to Pilot aims to support all pilots who fly from students to professionals and recreational flyers. The show includes genuine discussions with pilots who work in all aviation sectors including airline captains and bush pilots to share their experiences of flying. Join our worldwide pilot community through subscription to track your flying aspirations with other aviation enthusiasts.
Episode 355 of the pilot the Pilot
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Hey, it's Justin.
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airline.com justin my name is Tyler
Flagg.
I'm the the founder and CEO of
Flying company.
I was a special operations
pilot in the Air force for about
14 years before moving into
corporate aviation where I was the
chief pilot for a PC24 and
that's kind of where I started building
this company AV Nation.
What is going on?
And welcome back to the Pilot
to Pilot podcast.
My name is Justin Seams and I
am your host.
This intro will be short
because I am just cannot get over
this cold that I have been
stuck with for the past week.
But we're talking with Tyler Flagg.
Tyler Flagg flew special ops
in the Air Force.
He flew a Dornier.
Never talked to anyone that's
done that so it was crazy fascinating
to hear about his experience
one how he got into aviation just
kind of by a recruiter or not
recruiter but someone telling like
hey your grade's really good,
you should be a pilot.
He's like oh okay, cool, I'll
do that.
But it was really cool.
Talk with him how he
transitioned from the military to
being a chief pilot for a PC24
and eventually stepped away from
that job to start the flying
company, which is a pretty cool concept.
And if you are are an owner
operator, you look for pilots.
Or if you're a pilot that is
on the contract side, you should
definitely check them out.
So I hope you enjoy this episode.
And without any further ado,
here's Tyler
Flag from the flying company.
Tyler, what's going on, man?
Welcome to the pilot to Pilot podcast.
Hey, man, great to.
Great to get to do this.
Yeah, we have a mutual
connection, right?
Trevor doesn't all dreams.
I haven't talked to him in forever.
He randomly reached out to me.
Last time I talked to him is
when I got the job at my current
airline.
He's like, dude, congrats man.
Welcome to the team.
And he reminded me that he is
senior than me and that his life.
I was like, thanks, dude,
Appreciate it.
Classic.
Yeah, he's like, hey, dude,
you gotta have Tyler on.
He's building something cool.
He's got cool stories.
I highly recommend.
I was like, all right, dude,
let's do it.
Let's make it happen.
Yeah, he's a great dude.
We go back really long time
and, you know, we met freshman year
of college.
You know, we were both in ROTC
but in different programs, ended
up meeting during, you know,
what is effectively like Air Force
summer camp, where, you know,
they let you like go to a base and
just, you know, pretend to be
in the real military for.
For a month and got to know
him and we've been best friends ever
since.
And now we live in the same
town and raise the kids together
and everything like that.
We took very, very different
directions, you know, in the, in
the military.
He was the pointy nose fighter
guy, you know, on the bird pilot,
and I was the civilian clothes
wearing special operations guy.
And very.
It was, it was always fun kind
of catching up from time to time
because we never, you know,
were based in the same place or anything
like that, but it was always
just kind of funny to see the differences
in the.
In the two worlds that we
lived in.
Yeah, it is funny how you can
be based on the same place.
You both can be aviators and
you can have completely different
lives, completely different missions.
But I'm sure it just makes the
stories that much better, right?
I'm sure you meet up, you're
like, dude, what'd you do today?
It's like, ho.
Ho, you don't want to miss
this one.
Also, make sure your phones
are off and sign this NDA because
I'm not
supposed to tell you.
Yeah, yeah, no, it was a lot
of fun.
I also got to be be on his
plane when he did a affinity flight
in the T38, you know, many,
many years ago.
And this is a lot of fun.
Finally got to actually fly
with the guy.
So then you got to fly with me
in the PC24 once, which was fun.
Yeah.
PC24, what?
What a plane.
I flew the PC12 about 1200
hours in a PC12.
It was a lot of fun.
I never got to fly PC24.
I think it was just coming out
when I was transitioning from my
freight job and didn't really
want to stay to fly.
I would rather go do some
other things and did that.
But it looks like a great plane.
So Pilatus is always making
cool stuff.
Oh yeah, no, it was awesome.
And you know, I've got a
couple hours in the PC12 probably.
Right.
But like it's a very easy
transition for someone who was flying
an NG or an NGX to be able to
move into the end of the 24.
And I mean that's essentially
why they, they built it.
It's kind of funny and I don't
have any firsthand knowledge of this,
but I've heard from folks at
Pilatus where, you know, essentially
like the owner operator
community flying the PC12 like just
kept pestering them for years
like, hey, can you build a twin engine
jet that we can move into?
And they finally were just
like, o okay, fine, yeah, we'll do
it.
You know, but it's awesome.
I mean it's same like
Honeywell, you know, system.
You just got two zoomies
instead of one.
Right?
Yeah, it's pretty intuitive.
Yeah.
I mean needs to be Garmin.
That's the only mistake they made.
It has to be.
We're in the brand right here.
They made the mistake.
I think the.
I think, I don't know, like,
isn't the new, the new PC12 going
to be Garmin?
And then the probably speculate.
I will have to wait until that
is all settled and figured.
Yeah, that's fair, that's fair.
When I heard announcements.
So somebody, somebody fact
checked that to the point.
Jets are kind of like the
natural evolution, right?
I mean serious kind of went
through this with.
They had the SR20, the SR22
and their owners, as they grow up,
they get kind of just engulfed
in that brand and they just want
to see what's next.
Maybe they don't want to go
buy something else.
Textron Aviation had this down
pat, right?
They have the.
You start in 150.
All right, cool.
Now you go to a 172.
Now you go to 182, 206, 210.
You know, we have, like, every
make and model you could ever want,
and these other companies just
had one or had two, and they didn't
have that.
Jet and texture on aviation
dominates the.
The light jet market.
And for someone else to come
in and bring some competition, it's
good for everyone, I think.
100.
Yeah.
Yeah.
Well, let's talk about you, man.
Let's talk about why you
wanted to become a pilot.
We'll kind of get into, like,
did you always want to be a special
ops pilot?
But what was the original.
Why does Tyler want to become
a pilot?
Well, man, I. I have a rather
unconventional story, I think, and
I do kind of feel bad talking
about it sometimes, just because
I know that there's a lot of
people who grow up wanting to be
pilots, and it just never
works out for him, you know, And
I just kind of fell into it.
So, you know, I grew up right
outside of Manhattan in Jersey City.
New Jersey.
Did not come from a military
family or an aviation family.
My parents were actors, so
they met doing, you know, theater.
My.
My dad was on Broadway and off
Broadway in supporting roles his.
His whole career, and then
just kind of picked up odd jobs and
stuff like that when.
When he wasn't in a show.
And so that was, like, the
world that I was, you know, raised
in.
Like, I was backstage, like,
playing Seg Genesis with the stage
hands and stuff like that when
my dad was doing a show.
And I did, like, a little, you
know, child acting when I was a kid.
I was a failed.
Failed child actor.
No way, really.
But.
But then, you know, just had
other jobs in.
In New York City and, you
know, worked in retail and, you know,
was a lifeguard and stuff like
that, like, normal kind of kid jobs.
But, you know, I was a
sophomore in high school when September
11th happened, and, you know,
it was just a stone's throw away
from there.
Used to be able to see the
towers, you know, when I was going
to school every morning.
And so it was a, you know,
significant event, obviously, for,
you know, everyone and, you
know, especially, you know, a sophomore
in high school.
And so I kind of decided, you
know, right then and there that I
was going to join the military.
I wanted to enlist in the Marines.
My mom very Politely asked if
I could, you know, go in as an officer
and go to college.
And so put in my applications
to West Point, you know, which is
the, you know, US Military,
you know, Army's academy up in upstate
New York.
And then at the time, I don't
know if it's changed.
You know, whoever's going
through this process now knows better
than I do.
But at the time, you could
just kind of like, check an extra
box on the application and
then, you know, send it to a different
academy.
And so, you know, I ended up
sending it to the Air Force Academy
as well.
You know, both of the colleges
got back to me and were just like,
well, you're not smart enough
to go to our schools.
But the Air Force kind of had
me, you know, high enough on the
waiting list that they gave me
a scholarship to go do our rotc.
And so ended up, you know,
going to a small school in New Jersey,
did rotc.
I was a political science
major, you know, so, like, I just
kind of went in with, like,
hey, needs the Air Force, right?
You guys tell me, like, where
you want me?
And I assumed that they were
gonna have me be an intel officer
or something like that.
And then one day, gosh, I
think it's probably like, beginning
of junior year or something
like that is when you kind of have
to make that decision.
Like the.
This.
One of the staff sergeants who
worked at the detachment was just
like, hey, Cadet flag, are you
going to put your name in for a pilot
slot?
Said, no.
And she's like, well, if you
do, you're gonna get it.
And I was like, oh, all right,
that seems cool.
Let's give that a shot.
You know, I probably thought
about it for a lot shorter than I
really should given the, you
know, the monumental decision that
I was making at the time.
But it was all kind of based
off of your gpa, your commander's
ranking, you know, physical
fitness scores, how well you did
during field training, which
is like the, you know, boot camp
light that.
That they have the Air Force,
you know, officers go through, and.
And yeah, so I ended up
getting a pilot slot.
You know, pretty.
I was pretty excited.
Didn't really know anything
about it, Right.
And then the next thing was
you had to choose what base you were
going to go to.
And again, not knowing really
what I was doing, I was given a list
of, you know, five bases, and
I looked at it, and it was just like,
all right, well, this one's in
Oklahoma, this one's in Mississippi,
this one's in Texas.
And then there's Pensacola, Florida.
And I was like, well, is this
a trick question or something?
Like, I mean, obviously I'm
going to choose that one now.
Little did I know that I was
going to be training with Navy and
flying the T34, which is the,
you know, built in the 60s, you know,
used as the, you know, the
trainer for, for Navy and Coast Guard
and Marines.
And I wouldn't be flying the
same thing that all my other, you
know, Air Force, you know, you
know, friends were gonna be flying
in the T6.
But yeah, no, spent.
Spent a couple years down in
Pensacola flying with the, the Navy.
Had a great experience, loved
being down there.
And then, you know, went and
tracked for.
For T1s, which is like the,
you know, the trainer that you go
to, to go heavy and, and
special operations and stuff like
that and did that.
And then at the very end, you
know, you get your drop list with
all the different, you know,
things that were available at the
time.
You know, all your standard,
like, hey, C17 here, C130 here, you
know, KC10 here.
And then there was this one
little thing like down at the bottom
that said non standard aviation.
And that was it.
And like, no one knew anything
about was a brand new thing that,
like, hadn't been on a drop
list before.
And so we just kind of started
asking around to, you know, other,
you know, the other pilots and
instructors, and everyone's just
like, well, yeah, no, we don't
really know anything about it.
We just know it's an AFSOC
thing, which is Air Force Special
Operations Command.
And we know it's like, I don't
know, like, it's probably pretty
cool.
And, you know, me being the
idiot that I was was just like, oh,
yeah, no, it does sound pretty cool.
Like, yeah, let's go give that
a shot.
You know, and that kind of is
what, you know, set me off in that
trajectory and did that for,
you know, most of my time when I
was, when I was in.
That kind of sounds like your
whole kind of aviation career, right?
You're like, oh, that sounds
kind of cool.
Oh, you want to do special office?
Yeah.
I mean, you just followed the
gu feeling.
You were like, my stomach's
telling me to do it.
Let's do it.
Yeah, Very, very much so.
That's like the through line
of, of essentially my professional
career.
Well, they say trust your gut.
And it didn't seem to fail you
on that part.
Right?
Yeah.
I wanted to go back a little
bit to.
You mentioned 911.
You mentioned, you could see
the towers.
I want to talk.
I've never really had the
opportunity to ask, like, what.
I mean, obviously we know
about 911.
A lot of people, like pilots became.
Went to the military because
of that.
What was it exactly, seeing
that happen that made you want to
join the military?
What made it switch in your brain?
Was it just, I need to protect
my country, like, payback?
Or was it just like, this is
my duty?
But what, like, kind of
switched in your brain to be like,
I need to go to the military?
Yeah, I mean, I would probably
say duty, right?
Like, you know.
You know, the other aspect of
it is that, like, I. I didn't really
know what I wanted to do when
I grew up.
Right.
Like, you're expected to make
so many life decisions when you're
in high school, right?
And I was always kind of a
jack of all trades, master of none,
I guess, to put it politely.
And, you know, other.
Other, you know, kids that I
was going to school with, like, they
were really great at biology
and they knew they wanted to be a
doctor.
They were really great at
this, and they knew they wanted to
be a lawyer or whatever, or
singers and.
And everything, right.
I didn't really have that one thing.
Like, I, you know, I played sports.
I was, like, decent in school.
Like, I was cool with all the
nerds doing, like, tech stuff and.
And whatever, right?
But, like, there's not one
thing that I was, like, extremely
good at that I was like, ah,
well, this is what I'm gonna do.
Right?
And, you know, when that
happened, you know, I was, you know,
I'd always been a very, you
know, patriotic young American.
Right?
And, you know, just, you know,
we, you know, we lost a friend of
the family, you know, who,
like, was working in the towers that
day.
And, you know, every single
person that you knew growing up there,
you know, had some sort of,
like, you know, degree of relation
to somebody who was affected
by that.
Right, Absolutely.
And so it just was like a. Yeah.
All right.
This is.
This is the thing, right?
Like, this is what I was meant
to do.
And, yeah, that's kind of what
started the journey.
If it wasn't for 9 11, do you
think you would have ever gone down
this path?
Oh, no, absolutely not.
No.
What do you think you would be
doing right now?
No concept, actually.
Yeah.
I mean, it could have been that.
I mean, frankly.
But, like, you know, what's
interesting is, like, you know, I
joked about, like, being cool,
the nerds and everything like that,
and I. I love them.
Obviously, I'm in like a, in
the tech world now I'm a non technical
person, but like I'm getting
smarter every day.
So the, the public school
system where I grew up like wasn't,
was not particularly good.
And there was a, I guess what
most people would call a magnet school
that's like a, it's a public
school, but you have to apply to
get into.
And it was like a kind of tech
school, right, where like you, you
did your normal classes in the
beginning of the day and then you
had a major in the afternoon.
And mine was computer drafting
and design.
And so, you know, we actually
had like a, one of the really early
3D printers.
Like, you know, this is back in.
Yeah, like 2001, right.
So like, you know, very early
for a school to be able to get access
to that kind of stuff.
And so I messed around with
that stuff a lot.
And a lot of like the, you
know, 3D animation, you know, the
stuff that like Pixar and like
Dreamworks have, you know, you know,
used to, you know, turn into
movies and everything like that.
And so that, you know, that's
probably what I would have ended
up being doing like something
like architecture or something like
that.
Yeah.
All right, so you make the decision.
You're going to the military.
You know, you're still not
pilots on the radar.
Eventually they're like, hey,
you're actually, you know, kind of
smart.
We need some smart people to
do some cool stuff, fly planes.
You just kind of said like,
oh, that sounds cool, but did you
really know what you're kind
of signing yourself up for?
Was it, that sounds cool, let
me check it out.
Or was it like, that sounds cool.
Here, let's go do it.
I did a shockingly small
amount of research.
And so like I actually went in
and you know, again, not really even
recognizing that I was going
to be training with the Navy and
not really knowing the
distinction between a T34 and a T6
or anything like that.
You know, didn't really do any
study in advance, like I probably
ought to have, but just kind
of, kind of jumped in and you know,
in hindsight, right, Like, I
probably would have been better off
and would have been able to
learn quicker had I done more research.
But to a certain degree it did
kind of help me because I was just
like this, you know, blank
mold of clay, right, that like they
could teach me from the very
beginning the way that they wanted
to teach me.
Whereas a lot of people who
kind of came in who were in the same
classes as me and everything
like, that they might have had their
private pilot's license.
Maybe they had their.
Their cfi, maybe they had
their commercial, and they had to
kind of, like, you know, they
had to break them down and, like,
stop all a lot of the bad
habits so that they could teach them
in the way the Air Force
wanted them to be taught.
Yeah.
But I didn't have to worry
about that.
Right.
And there's also a lot of guys
who, you know, I was with who washed
out.
And, you know, maybe they came
from a family where, like, their
parents were fighter pilots or
something like that.
Right.
But they just had this, like,
you know, immense generational pressure
to succeed.
Right.
And so, like, every single
check ride they did was, like, the
most important checkride of
their life.
Whereas me, every single time
I got to a check ride, I'd, like,
salute the guy, and I'd be
like, hey, man, like, we're gonna
go find today.
Like, this is gonna be awesome.
Right?
You know, so, like, I was just
kind of playing with house money,
in my opinion.
And so, like, every day, I got
to go up there and, you know, and
fly and learn and get better.
Was.
Was cool.
My book.
Did you ever have a moment
where you're like, this is.
How did.
Like, this is way too much.
How did I get here?
Or were you just kind of all in?
You're like, this is fun.
I'm gonna do this as long as I can.
Yeah.
I don't.
I don't really remember any.
Just, like, you know, moments
of, like, panic or anything like
that.
You know, instruments was
definitely, like.
That was the thing that took
the longest for me to.
To grok.
You know, I didn't really
fully understand instruments until
I got into the.
Into the T1, which is the
Beach 400.
That's when things started to click.
When I was, like, in the T34,
I was just, like, hanging on, trying
to, like, you know, trying to
keep up.
Like, I was.
I was much better at, you
know, ironically, given what I ended
up doing, you know, I was much
better at aerobatics.
I was much better at form
because it was all.
It's like, spatial awareness
and, you know, everything like that.
And, like, that was what, you
know, what I was better suited to
do.
But the, you know, the book
stuff of the, you know, the.
The instruments was the
challenge for me.
Yeah.
And then, so you're going
through training, you're doing well
enough, where I'm guessing you
had the opportunity to kind of choose
what you'd want.
Right.
I'm guessing based on the
conversation that we've had about
how they told you, hey, you
could be a pilot, or, you know, it
just seemed like you worked
hard, you put yourself in the position
to give yourself options.
Is that correct?
Yeah.
And I honestly can't remember
where I had, you know, what.
What I ended up getting on my.
On my drop list.
But, yeah, you know, it was
pretty high at the top, and I was
probably the only one who was
dumb enough to put something that
no one knew anything about at the.
At the top of my list.
It was just like, oh, yeah,
well, we got to give that to Tyler.
When you started your kind of
Air Force training and when you started
going through this process,
did you have a goal that you wanted
to do?
Were you like, I just want to
fly fighters.
I wanted to fly big equipment.
You mentioned that you're
really good with the spatial awareness
and kind of flying in
formation and doing aerobatics.
So was it kind of you wanted
to fly fighters, you wanted to eventually
do Thunderbird stuff, or were
you kind of just open anything?
Yeah, I mean, I was kind of
open to anything, but I. I didn't
particularly want to go fighters.
Like, I wanted to travel.
You know, I never really got
to see the world when I was a.
A kid.
You know, we'd take the
occasional, you know, family vacation
from New Jersey to Ohio or whatever.
Right.
But.
But that was about it.
And.
And so, you know, getting the
opportunity to really go out there
and, you know, spread my wings
and, you know, see the world and
everything, like, that was
definitely very appealing to me.
And so the heavy community was.
Was definitely, like, the.
The way to go for that.
And, you know, with what I
ended up doing, like, I flew operationally
in about 67 different
countries, so I would say that I
def.
I definitely, you know, managed.
Managed to do that.
Yeah, you check that box for sure.
All right, so drop comes.
Everyone's probably talking.
You know, they're.
They're saying what they want
to do, they're saying what they want
to do.
When you got, you know, the
drop came up, I don't know if they
did it how they do now.
Right.
Like, every time on Instagram
of swiping, it's like you have a
big presentation, then you see
the same picture.
Yep.
So when you get.
Get special operations or.
It wasn't even labeled that.
Whatever was labeled, is
everyone just, like, really?
You wanted to do that?
Like, we thought, like, what?
Yeah, no, there's a lot of
just, like, polite, you know, golf
clapping, like, oh, yeah,
like, okay, cool.
Good luck.
Dude.
And you know, it honestly
wasn't even until I actually got
to my first base that I, you
know, they told me what plane I was
going to be flying.
And so, you know, it was
several months later after, after
drop where I still didn't
really have much information.
But like you go from, from,
you know, your, your drop night to
you know, you finish up the
rest of your academics and you graduate
and have a formal graduation,
then a couple months later you go
to survival school and then a
couple months later you end up at
your, you know, first squadron.
Yeah.
And then what was your
expectations versus realistically
what happened?
Like you mentioned, I didn't
really give you much information.
So were you just like, I don't
really know what's going to happen.
Did once you got accepted, did
you have like a little community
you could reach out to or is
it just like, we'll let you know
when you need to know what's
going to happen?
Yeah, there, there is not much.
You know, it was all just kind
of hearsay and like word of mouth
and stuff like that in terms
of what, what you were going to be
doing.
But, but yeah, I mean it was
when I finally got to, you know,
the, the squadron, they're
just like, hey, like has anyone told
you what plane you're flying?
And I was like, nope.
They're just like, oh, it's a,
it's called a Dornier 328.
And I was like, okay, yeah,
Google, I guess I will look that
up then.
You know, I have seen a couple
of Dorniers when I was flying aerial
survey.
We used to go, I can't
remember where I was.
I think it was called Barry
Aviation and I think they did contract
flying with the military in
their Dorniers.
So I don't know if it was
similar if you flew those Dorniers
or not, but I would see them
all lined up.
It's like, that'd be sweet to fly.
And someone's like, that's
like real hush hush stuff.
Like we don't talk about what
they do with those.
Yeah, no, I'm not too familiar
with, with Barry.
I know that they're, they're a
contractor, but yeah, they've got
a pretty, how do you say
they've got a, they've got a fleet
with just a lot of different,
you know, different aircraft in it.
But, but yeah, no, it was a
great plane for what we needed it
to do.
Right.
And so, you know, you know,
there's plenty of information on,
on the Internet.
You know, most of it is
honestly probably bad, but the, you
know, it was essentially intra
theater, special operations, mobility.
And so it was not the kind of
plane that is obviously able to go
from the US to, you know, a
deployed AOR very easily.
Right.
It takes, you know, a week to
get from the US to, like, Africa
or the Middle east or
something like that, because you
got to do the whole hop up
through, like, Greenland and Iceland
and all that kind of stuff.
So, you know, how it work is
essentially like, we'd have some
aircraft within an AOR when we deploy.
We'd go there.
We'd spend three to four
months there with the planes, and
then everything that we did
was just, you know, moving teams
where they needed to go within
that aor.
And so, you know, the.
Whether it's seals, Rangers,
Green Brace, whoever, like, they
knew that they could call us,
and we were able to respond, you
know, a lot quicker than, you
know, other, you know, you know,
large, like, Air Mobility
Command assets that the Air Force
has.
So what kind of flying would
this be then?
I'm guessing a lot of this was
flying to smaller, not necessarily
like, your bigger bases, or
was it small flying into places that
planes really aren't used to landing?
Or was it off airport stuff?
Kind of talk about where you
would actually fly to and drop off
and pick up.
Yeah.
So all of the above, you know,
is very much like hub and spoke stuff.
Right?
Like, you know, C17, C130,
drops off, you know, a bunch of teams
in, you know, at, like, a
large Air Force base or something
like that within an aor and
then we take them from, you know,
there to wherever it is within
the AOR that they need to go.
And we're able to do that,
like, pretty rapidly.
You know, most Air Mobility
Command assets, like, they essentially
have, like, what's called
tacc, which is up at Scott Air Force
Base in Illinois.
That's essentially like an
airlines version of, like, you know,
an operations center, like
schedulers and dispatchers.
And whatnot.
Right.
That they handle all the
scheduling and the diplomatic clearances
and fuel planning and all that
kind of stuff, and they just, like,
hand the crew a packet, essentially.
We were kind of set up
intentionally as, like, an autonomous,
like, unit where we, like,
handled all that stuff internally,
which was a huge pain, like,
taught me a lot.
But it did allow us to be able
to kind of move pretty quickly.
And so, yeah, it was the kind
of thing that, like, we're doing
the fuel plans, we're doing
the flight plans, but then we're
also the one that's like, you
know, calling some, you know, tower
at some, like, little, you
know, airport in the middle of nowhere,
you know, asking for permission.
We're talking to the embassies
and everything like that, to be able
to get approval to land places.
And so it was pain, but, you
know, it taught us a lot and also
allowed us to, you know, move
really quickly.
But yeah, going, going back to
your original question is that, like,
it could be.
It was, it was different every
day, right?
Like, some days you're just
going from like, one big military
base to, like, another airport
within the aor.
Sometimes you're going to,
like, a little dirt strip in the
middle of nowhere on NVGs at
night and landing in a tiny little
box of IR lights.
And so, like, that was the
kind of thing that we, like, trained
for.
You didn't do it that much, right?
But, like, that was the thing
that you had to train for the most,
just because when it happened,
it was a no joke, like, you had to
make it happen kind of thing.
Yeah.
And a lot of people that I
talk to when they're in the military,
when they finally get
deployed, you know, they kind of
feel a sense of pride.
They're like, I finally get to
do what I've been training for for
so long.
Would you agree with that?
When you're out there like,
oh, this is the mission.
We're finally gonna do it.
Were you kind of, like, hyped
up or were you ready to go?
Oh, yeah, no, no, absolutely.
And, and it was, it was kind
of wild, you know, like, you know,
I finished up pilot training
with probably like 200 hours, something
like that, and then probably
had about 50 in the actual aircraft
before my first deployment.
And, you know, I went out to
Africa for my first one.
You know, neither me nor my
pilot in command had ever been there
before.
The guy who is my pic, my
aircraft commander, had less hours
in the Dornier than I did.
And so it was like the blind
leading the blind to a certain degree.
But, like, you know, I. I look
back on it now and I'm just like,
oh, my gosh, like, how did,
like, how did we do that without,
like, you know, messing
something up terribly?
Right.
But at the time, you know, the
training is good, and so you feel
really confident and maybe a
little overconfident.
Right.
But it all worked out, man.
When did you feel comfortable
in your deployments?
Was it just like, you know,
day one, Strap up, you ready to go?
You felt like you could trust
your training or was it, you know,
a Couple missions in, you're
finally like, all right, this is
the job.
I know what I'm doing.
I feel, I feel confident in
doing, doing this.
Yeah.
So I was very fortunate that I
got to deploy to every single one
of our AORs.
And it was really much like a,
the first month is a struggle because
you're still trying to
understand the lay of the land.
You're trying to understand,
you know, what are the big things
that you need to be concerned
about in every single aor.
And also just the language barrier.
Right.
Like, even though, you know,
you know, English is the, the language
of aviation, you still have a,
you know, it's still difficult to
interpret what, what people
are saying in, in every one of these
places, especially when you're
going to like, smaller, you know,
non capital cities, you know,
in, in these countries.
And so getting over that over
the first month was like the biggest
challenge, but then like the
second month you kind of figure things
out and then like the third
and fourth month, like you're pretty,
pretty confident.
Yeah.
And then just in time for you
to have to train the next person
in the go.
Yeah.
Geez.
Did you have any memorable flights?
Do you have anyone.
I mean, obviously you can't
speak probably of everything that
you've done over there, but do
you have any, like, very memorable
flights that stick out,
whether it was just a crazy day with
crazy environment, crazy
landing experience, or just like
a high profile mission or
something that just went wrong?
Oh, yeah, I've got, I've got
one of those from, from or you know,
at least one of those from
every single AOR I went to.
You know, I would say that,
like, there, there was some very
important life lesson and
flying lesson that I learned in every
aor.
Right.
In like Africa, it's fuel management.
You spend a lot of time flying
over the Sahara and there's nowhere
to go.
Right in the Pacific.
It was weather, some of the
worst weather that I've ever seen
and the worst, like icing and
everything like that that I've gotten
has been flying, you know, in,
in, in the Pacific in South America.
You know, VFR flying and
mountainous train.
You know, that was a
significant, you know, you know,
learning experience there
because we just don't do that much
in, in the U.S. right.
Like everything is radar.
You know, you can, you know,
always get an IFR flight plan, but
like, once you kind of get out
of like Bogota or something like
that, like you're just kind of
flying around vfr, you know.
Now, fortunately, there's just
not as many planes there, so you
don't have to worry about that
as much.
But.
But yeah, no, it was, it was great.
And, you know, I feel like it
did make me a pretty well rounded.
Yeah.
You know, pilot.
Given all that.
What was your favorite place
to fly?
Oh, I mean, in terms of, like,
fun flying, like South America, I
would say, like, it was just a
lot of like, you know, vfr.
Like, you're following rivers
and stuff like that to be able to
like, get to where you're going.
It's like, that was genuinely enjoyable.
But there's a lot of places
that like, like I love in every single
AOR that, you know.
You know, we kind of lived off
the economy, right?
So, like, we weren't on
military bases most of the time.
We were living, you know, in
hotels or safe houses or, or whatever.
Right.
And we're wearing spoon clothes.
And so we're just kind of
like, you know, going into town,
like, grabbing some food.
Right.
And so a lot of places that,
like, I, I thoroughly loved going
and like, would love to go back.
And then there's obviously
some places that I don't particularly
care to
when it comes to Special Ops.
You know, people there, the
first thing I think of is like Seal
Team 6 or the Green Berets and
just being a seal in general, but
for phone dropped, but for
this itself.
From the pilot side, was there
extra training?
Was there kind of like a.
A Buds, I think it's called
like a Buds Week or like a Hell week?
Was there anything like that
involved with being a pilot as well?
That that made it, I don't
want to say more intense because
obviously training is intense
as it is, but kind of like that whole
Special Ops feeling,
not so much on the, on the
pilot side.
You know, my first squadron
commander, who I loved a lot, you
know, always used to say that,
like, just because your patch says
special does not mean you're special.
Right?
And, you know, he, he wanted
to make sure that we, you know, knew
that like, you know, we were
supposed to be quiet professionals
and we were supposed to just
train really hard and work really
hard, but, like, not make a
big, you know, deal and big stink
about it.
Right?
Because at the end of the day,
we're just pilots.
And, you know, you just kind
of happen to get that on your drop
sheet, right?
Like, you know, they should
theoretically be finding people who
are going to actually be able
to do the job, you know, and then
they shouldn't, you know, give
them that position on.
On the drop.
But it is still kind of luck
of the draw.
Right.
But it was the level of
training that we had to do and had
to, you know, complete that.
You know, I, I feel like, did
kind of, you know, set us up for,
for success.
Right.
And so, you know, the very
first time you're taking a 30,000
pound plane into a 20 foot
wide, you know, or try 25 foot wide,
like dirt strip in the middle
of nowhere on nights on, on NVGs,
like, you kind of have to have
your stuff figured out, you know.
And so, you know, we, we did
that, we trained a lot to that, that
standard.
And you know, you get to the
point where, like, you're actually
pretty confident in it.
You know, you get to the point
where I kind of would rather land
like that than land the other way.
Yeah, yeah, don't give me the
100 foot fit or 150 foot Runway.
I'll mess up on that one.
Give me 25.
Oh, no, no.
Exactly.
And then like when you go back
and forth between the two, like on
any given day, you're just
like, oh my God, this is.
Yeah, you got a good landing
in the dirt one, then you bring them
back like, dude, what the
heck, man?
You got a lot screwed it up
that bad.
What's wrong with you?
Yeah, well, so the, the funny
story, and I have no idea whether
or not this is true, but the,
the wheelbase was 11ft wide on the
Dornier and the minimum Runway
width was 22ft wide.
And rumor has it that like,
whoever stood with the squadron just
kind of took the wheelbase and
doubled it and was just like, yeah,
that's probably good enough.
Sign that off.
Cool.
They'll, they'll figure it
out, you know.
Yeah, they're essential.
They'll make it work.
If not, whatever.
Yeah, five feet on either
side, it'll be good.
They're like, no one knows
they're down there anyways.
We'll just leave them.
What was I gonna ask?
Did you ever.
So you drop people off, I'm
guessing it was kind of like a very
need to know.
Like you don't really know
what they're gonna go do, but maybe
you do.
I could be wrong, but do you
ever get back?
I mean, it could even be like
years from now and you hear a story
on the news in an area where
you know that they could only have
got to by you flying them, and
you're like, oh, that's what they
were doing.
Have you ever had that moment?
So we, generally speaking,
we're not like completely in the
know, you know, we would Just
kind of drop them off and you have
a general idea of, like,
what's going on.
But, like, for the most part,
like, we're just not as cool as them.
And, like, you don't need to
know, like, all those details, right?
We're just kind of focused on,
like, all right, I'll get you from
point A to point B, right?
Drop you guys off and.
And then, you know, you let us
know when you need to be picked up
kind of deal.
Yeah.
What was it like when you
drop, you know, high professionals
that are training for missions
and going out to do some crazy things?
What was the interaction with
them like, was.
It was nervous nerves on their.
Where they just.
Just the normal guys just
like, shooting the breeze.
And as soon as you land,
they're like, all right, mission
time.
See you, dude.
Yeah, no, the.
Those guys are great.
And, you know, typically,
like, you'd be kind of, you know,
on a deployment, like, it'd be
the same team that you're working
with most of the time because,
like, that's just kind of how their
rotations work.
And so over the course
deployment, like, you'd get pretty
familiar with them.
You're on the phone with them
a lot.
Like, you're seeing them in
person and just like, super, you
know, super chill guys, right?
Like, there's not like, you
know, any like, very humble people,
right?
Even though that.
That's obviously not like,
the, you know, the way that they're
probably perceived in.
In, you know, you know, on
like, social media or in movies or
anything like that.
But, like, yeah, super, super
humble folks who, like, they appreciate
what you're doing, right?
Because, like, you're the way
that they're getting from point A
to point B, so they don't have
to, like, like, you know, be in a
jeep for two weeks or
whatever, right?
So it was always the.
The times where, like, we had
to move somebody who was like, you
know, an aide to a general or
something like that, where they'd
just be like, uppity and
obnoxious, right?
Like, asking where the
catering is.
It's like, bro, come on, you
bring it yourself.
All right, I've got a bagel.
I've got a bagel up in the cockpit.
He's like, well, that's my
bagel now.
Yeah.
So how do you.
What's it like when you line
up for your first 25 foot wide landing
in the middle of nowhere on
night vision goggles?
Do you feel like you're fully
prepared for that moment, or can
you not really be prepared for
what that feels like.
Yeah.
I don't think you can really
be prepared for that.
And funny enough, like, just
the other day, so I'm here in Arkansas,
and I got asked to.
To guest teach a.
A class for, like, an aviation
systems and safety class at the U
of A.
And I did it all on.
On NVGs, and, like, how great
NVGs are, but also the visual illusions
that, you know, come along
with that, because you've got a reduced
field of vision, you've got no
depth perception, it's monochromatic,
Right?
And so it's the kind of thing
that you have to be training for
all the time, consistently,
otherwise you can put yourself into
a really bad spot, right?
And it's just, you know,
you're looking through, like, a little,
you know, soda straw,
essentially, right?
And it's green and, you know,
depending on where the.
The moon is in the sky and how
much other illumination you have
and the shadows that you get,
like, dictates what you're able to
see well.
Right?
And so a lot of people, you
know, have unfortunately crashed
planes just because of the
visual illusions that they get from
nvps.
Yeah.
And so, you know, it's the
kind of thing that, like, if I went,
you know, a couple months
without doing an MVG flight and I
got back into it, like, I had
to force myself to, like, oh, okay,
remember the basics, right?
Just, like, keep scanning your
vision, right?
Don't let yourself get hyper focused.
And so, yeah, like, the first
time I went out on MPGS to a little
dirt strip, and, you know,
they'd set up, like, a little IR
light box, essentially.
I can't remember what the
dimensions of that were, but it's
pretty small.
And, you know, you're expected
to land in the box, right?
And of course, like, I happen
to be there with the squadron commander,
like, in the.
Of course, you know, in the seat.
Left seat.
And of course, like, I really
wanted to impress the guy, right?
And so, you know, we're coming down.
You got to kind of, like, aim
short of the box, right?
So that, like, you end up
landing in the box and you pull power
and you float a little bit.
And I landed in the box.
I smashed it into the box.
Like, it was probably the
hardest landing that I've ever had
to this day, because I just
wanted it so bad, right?
And, you know, we, you know, I
pulled into Beta, and we come to
a stop on the.
On the landing strip or whatever.
And, you know, the.
The squadron commander,
because he's seen, you know, he's
seen this a million times, right.
He just kind of keeps looking
forward and he's just like, all right,
can you just flare next time?
And I was like, yeah, no, no.
Yes, sir, most definitely.
I will remember to flare, no problem.
Yep.
Sorry, I'm gonna go cry.
Yeah, yeah, that's good.
Got it out of my system, but.
But then, you know, you.
You figure it out over time.
Yeah.
So you mentioned Trevor, right?
We talked about him before.
When you guys met up and would
share stories, was he just like,
you're doing what?
He's like, I mean, I thought I
was doing crazy stuff, but, like,
I'm just flying an air show, right?
Like, I mean, obviously the
Thunderbirds, there's more and what
he was doing, but it's like,
it's not really just.
Was he just kind of shocked
when what you could tell him.
Yeah, yeah.
It was always a lot of fun to
kind of share stories about that.
Right.
Because it's just a very different.
The fighter community and the
special operations community are
just like, very different.
Yeah.
Universes.
Right.
Like, you know, fighter
community all has call signs.
Like, we were all on a first
name basis.
And then like, you compare
that to like Air Mobility Command
folks, and then it's very much
like, like, you know, Captain such
and such and Sergeant such and such.
And sometimes like, you know,
we'd be, you know, I'd be out and
about with like one of the
enlisted, you know, air crew that,
you know, was with us all the time.
You're on a four month
appointment with this person, right?
Like, you're wearing civilian clothes.
You're in the middle of nowhere.
You're not going to refer to
each other by Sergeant such and such.
Right.
Like, that would be ridiculous.
Right?
So it's just like, hey, Bob,
you know.
Yeah.
But then like, some chief
master sergeant would like, overhear
me, you know, like calling my,
you know, enlisted air crew by their
first name and like, get all
butt hurt about it.
It's like, bro, come on, man.
Like, we're in the same
cockpit, we're in the same places
for, you know, four months.
Like, I, I don't care.
I'm going to call this person
what I want to want to call them.
And so, like, the dynamics
between all the different, you know,
you know, flying cultures are.
Are super interesting, you
know, but it was always fun to hear
his stories and, you know, it
was a very just, you know, different.
Different kind of universe.
Right.
Like when they'd get back from
a deployment, like, because their
whole squadron, right.
Would like Deploy at the same time.
And like, there'd be like a,
you know, ticker tape parade or whatever.
Right?
You know, it's like I'd get
back from a deployment, I'd land
on a commercial flight, and a
buddy of mine would like drive an
hour and a half to pick me up
from the airport and like, I'd show
back up at the squad on the
next day and people were just like,
oh, hey, where you been?
Finally back.
I got some, I got some TPS
reports for you to fill out.
Yeah, you got 100 emails you
got to respond to.
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that's txt.com did you.
So you kind of came in
aviation with no idea that this is
what you wanted to do, right?
Like, you just kind of fell
into it.
Your own words.
Would you say that you fully
love, like, did you fully get bitten
by the bug?
Were you just kind of like,
it's still cool, but it's not what
I want to do forever or kind
of just talk about your dynamic of
how you felt about aviation as
you're going to transition out of
the military.
And did you want to fly?
Was that like, important to
you or you kind of open other things?
Yeah.
So, you know, I love aviation,
I love flying, but there's always
been a lot of other things
that I've been interested in.
Right.
Like I like building things, I
like working on projects.
I like trying to, you know,
make things more efficient and effective
and, you know, create value in places.
And you know, I always, one
of, you know, one of my problems
being in the military was
like, it's, you know, it's very much
an inside the box kind of,
kind of kind of thing, unfortunately.
Right.
Yeah.
You don't just kind of get to
create side projects and like run
with it and, you know, get
adoption within the military.
There's processes for, for all
that kind of stuff.
And so I was Pretty excited
when I got out with the, you know,
the possibility of, like, he,
I want to go somewhere, I want to
keep flying, because
obviously, like, that's what I know
how to do.
But ultimately, I want to find
an industry or segment of the industry
where I can make a difference,
you know.
And so when I got out, like, I
could have gone to the airlines.
I had started working on my
applications and everything like
that, but then I did a
Skillbridge program.
So Skillbridge is like, when
you're in the military, within your
final six months of being in
the military, you can, like, volunteer
to do an internship
essentially at a company.
And so you remain on active
duty, so the company can't pay you
because you're still getting
paid by the taxpayer.
Thank you very much for that.
And so I went out and I went
to Los Angeles and interned at this,
like, a little aviation tech
startup that was out there, and it
was super interesting.
Had a great experience, met a
lot of really great people, and kind
of like, got bit by the
startup bug.
And so, you know, through
that, ended up meeting some, you
know, folks out there who are brokers.
They had a buddy who just
bought a plane in.
In Arkansas and was like, hey,
you know, friend just bought a plane,
you know, looking for a chief pilot.
You know, I think you really
like the area.
It's super family friendly.
You got young kids.
And so we came out and visited
and just so happened, you know, Trevor
was also moving, you know,
here at the same time, we're just
like, oh, my gosh, this is
just perfect.
And so, you know, did that for
several years.
You know, had to learn a lot
about par 91.
You know, like, I'd.
Man, you know, like, I.
Again, I. I just kind of,
like, didn't really think about it
too much.
I was just like, oh, yeah,
that seems cool.
Let's go do that, right?
Yeah.
How hard could this be?
You know, like, I'd managed
planes in the military.
Like, in my final deployment,
I was a deployed squadron commander.
So I had 35 people under my
command and, you know, a handful
of planes flying operations everywhere.
I was like, yeah, surely I can
manage a Part 91 plane.
And then, of course I get
there and it's like, you know, insurance
and taxes and loas and like,
all the stuff that, like, I was just
not familiar with.
So I had to, you know, pretty
quickly get.
Get spun up on all that.
But, you know, my.
My hope with.
With corporate aviation,
which, you know, has turned out to
be true, I think, is that, you
know, it's a very fragmented industry,
right?
You've got, like 22,000
business aircraft.
You've got hundreds of
thousands of pilots.
You know, most of the business
aircraft are all, like, single aircraft
operations, which means you
have, like, thousands of flight departments.
And I was like, you know, if I
go into that industry, I'm bound
to, like, find something that,
like, is going to be interesting,
that, like, I might be able
to, like, work on and fix and, and
try to make better and.
Yeah, so that's kind of where I
am now before we get into kind
of what you're doing now.
I played sports all the way up
to college, and a lot of people that
didn't make it to the NFL and
when they went to kind of the real,
quote, unquote, the real
world, they.
They struggled with
transitioning out of, you know, in
sports and military, every
single hour, every single minute
of every single day is almost
planned, right?
Like, you, you know what
you're going to do, you know, what
you're eating for lunch.
You know, when you're going to
be able to study.
You know, you're gonna, like,
everything is planned.
And when you get out of that
and you get back into the real world,
as you would probably call it,
the civilian world, was that a difficult
transition for you?
Do you think you were set up
for success with that, or is that
something that you struggled with?
So, I, I wouldn't say that I
struggled with it.
I know that obviously a lot of
people do, and so I, I don't want
to, you know, know, demean
the, the stroke or anything like
that.
But, like, I, I've, you know,
at least for the last, like, you
know, three or four years of
me being in the military, like, I
knew I was going to get out, right?
And so, like, I kind of had
one foot out the door already where
I was, like, trying to meet
people in other industries and, you
know, learn skills, you know,
outside of just like, being a, you
know, a military officer and
everything like that.
And so I wouldn't say that I
had, like, a huge plan.
Right.
Like, one of the reasons that
so many, you know, people go from
the military, aviation to the
airlines is because, like, it's a
very easy transition, right?
It's like a, you know, you
fill out the checklist, you, you
know, fill out your profile,
you send, you know, the applications
in, you go through their whole process.
It's very regimented.
And then, you know, you get
into the airlines, and then, you
know, life is.
Life is good.
Yeah.
And so I wouldn't say that I
had like a, you know, a huge grand
plan.
But like, like I'd been
thinking about it for so long that
like the transition and like
the, you know, I'm no longer, you
know, a, a major in the Air
Force, like, wasn't like a huge moment
of panic or anything like that.
But then there's a lot of
people who like kind of unfortunately,
right.
They get injured or something
like that and they kind of get thrust
into that and, and, and it's
a, it's challenge.
Yeah.
It's just two totally
different worlds.
Right.
I mean, you can be a superhero
in one world.
Everyone can look up to you.
You're the rank, you're, or
you're the best quarterback, whatever
it is.
Then you come to the real
world, people are like, that's cool.
But like, can you do a spreadsheet?
Yeah, yeah, no, exactly.
Yeah.
Do you know how to tag someone
in email?
Do you know how to not reply
all like, it's just such a different
world, right?
Yep.
Yeah.
All right, so you are managing
the, the plane.
You're PC24.
You're flying that all the way around.
What was it like going from
doing these special missions, flying
these like, really intense
people to just flying a businessman?
Was that also difficult or.
Because you mentioned before
your favorite flying was kind of
like the exciting flying.
It's not necessarily just
flying IFR from point to point.
Was that difficult to go to?
No, no.
I mean, I, I thoroughly
enjoyed it.
Right.
Like, you know, I was
fortunate that the, you know, the
schedule that we had was very
much a part 91, you know, kind of
schedule.
Right.
175 hours a year or something
like that.
Right.
So like nothing, nothing
aggressive of, you know, the, the,
the, the gentleman that I was
working for was, was great.
And like, you know, there was
one time I think, where, you know,
he texted me in the morning
and was just like, hey, we kind of
have an emergency.
Like, is there any chance
you're able to like, you know, fly
today?
And I was like, oh, yeah, no, sure.
I mean, I'll have the thing
ready for in like an hour, like maybe
at the airport.
Right.
But most of the other trips,
like, they were planned out well
in advance.
That's good.
And so it wasn't, you know, a
huge achievement adjust, you know,
adjustment there.
It was really weird for me
getting used to flying single pilot,
you know, for like the first
year and a half we only had dual
pilot insurance.
And so I had to find somebody
to fly with me every single time.
But then once we got Single pilot.
I was able to obviously do
most of the single pilot myself.
Yeah.
And yeah, it was, it was an
interesting dynamic, right.
Just because like I, I was a
crew dog, right?
Like I was used to having
somebody to talk to and I would just
be in the cockpit, like
reading off checklists to myself,
you know, and like flaps, gear
flaps, you know, just like,
you know, everything about
that plane.
Read the PO covered it back 10 times.
Sound like a crazy person
talking to myself, you know.
Yeah, yeah.
The guy comes like, is that
you talking to yourself?
Are you seeing show tunes?
Like, I don't know.
Don't worry about it, dude,
just worry about it that we get there
safely.
Right.
So you mentioned, well, I know
this, but no one else knows this,
but you mentioned, not yet at
least you were looking, always looking
for another pilot.
Right.
The first question is, was
that because you needed enough time
to get the single pilot
insurance, was that solely based
on the pilot itself for the
dual pilot insurance, it was just
waiting on you to get 250 in
type or 150 in type, or was it just.
That was just the best option
for the owner?
Well, so it was, it was
prohibitively expensive in the very
beginning.
People didn't really know how
to underwrite the PC24 because it
was a brand new plane.
It was one of the earliest
serial numbers.
And so it was just very
expensive to get dual pilot or single
pilot insurance instead.
That was the kind of the limit
factor there.
And then you were constantly
looking for pilots, right?
Was that a big challenge,
would you say?
Or was it not as hard as you thought?
Yeah, but that was a huge pain.
So, you know, if we had a
flight, you know, once a week or
something like that, I had to
spend, you know, three, four days
like working on, trying to,
you know, find, you know, some names
of pilots, have them send me
pilot history forms, send those pilot
history forms to the insurance
broker to like get a thumbs up, up.
Just that alone was like a two
or three day cycle, right.
Finally get a thumbs up from
them, you know, sign a pilot services
agreement with the person,
share a bunch of information about
the plane, where we're going,
the itinerary, the mission, the company,
everything like that.
And then I gotta like loop
them in with the accountants to make
sure they're gonna get paid
and then do the flight.
And then after the flight you
gotta do like receipts and everything.
It was just like, it was a
constant like never ending pain in
the butt, frankly, you know.
Yeah.
And I also just didn't feel
like you Know, I could justify going
to my boss and being like,
hey, man, like, let's just go to
a staffing firm that's going
to charge you a 30 to 50 markup because
I'm, like, too lazy to do all
this work on my own.
Right.
You know, and so, yeah, it was
a pain.
And like, you know, like,
people were finding pilots on Facebook
groups and still are today,
and I didn't even have a Facebook
account because I got rid of
that when I, you know, went into
afsoc.
And so it's just like, it was just.
Yeah, it was just a never
ending, like, annoyance for me.
Yeah.
And then you decided you
wanted to fix that.
Right.
That was like the.
Did you have an epiphany one day?
You're like, I'm just tired of
doing this.
I can do this better.
Or just right place, right time.
Decided to walk away and then
work on this.
Yeah, no.
Right place, right time.
And also, you know, a lot of
inspiration from, you know, friends
of mine who, you know, had,
you know, thought through this kind
of thing, you know,
previously, but, you know, ultimately
just kind of put out like, a
very basic alpha version of.
Of what.
What, you know, has become
flying company.
And it was limited to just the
PC 24.
Right.
Like, marketplaces are hard.
Marketplaces suck.
That's why, like, literally
every single person I talked to in
the very beginning was just
like, please, Tyler, don't do this.
And I was like, well, you
know, I'm dumb and I'm stubborn,
so I'm going to do it anyway.
But, you know, you have to
limit yourself in some capacity when
you build a marketplace.
Right.
Like Uber, Airbnb.
Right.
It was limited to just like,
you know, downtown San Francisco
or something like that in the
very beginning.
But you can't geographically
limit with aviation, obviously, so
I just limited it to one model.
So I sent out the alpha
version to, you know, some PC 24
pilots that I, you know, knew
and was good friends with and send
out some operators who had
flown as a contract pilot for in
the past and just kind of sat
back and watched what happened.
Yeah.
And then, you know, the Plotus
Owners and Pilots association approached
me and was like, hey, can you
add the PC12 on there?
And I was, okay, I don't know
that much about the PC 12, but I'll
figure it out.
Then did that.
And again, just kind of like,
it was a little side project for
me, but I just kind of, you
know, listened to feedback and talked
to people and tried to get a
better idea, like where the value,
you know, was.
And, you know, you kind of
fast forward now and, you know, we're,
you know, supporting citations
and Embraer, Gulfstream, Falcon,
Bombardier, you know, what
have you.
And, you know, the focus is
essentially like, you know, from
the, from the operator's
perspective, you know, we want to
make it as easy as possible
them to find and assess and hire
and pay pilots all in one place.
Right.
Being able to kind of give
your internal flight department team
all the tools they need to be
able to handle their staffing internally
without spending a bunch of
time, but also without having to,
you know, go to a staffing
firm that charges a significant markup.
Right.
And then from the pilot's
perspective, being able to allow
them to very easily, like,
contract directly with companies,
you know, because, I mean, a
lot of professional pilots, you know,
who are, especially ones who
are doing contract work, often have
their own LLCs, and they would
love to be able to just run all their
trips through the LLCs.
They're in a tax, you know,
optimized state and everything like
that.
But then, you know, when they
accept the job from a staffing firm,
they, you know, that that firm
typically forces them to be a W2
employee, and so that
therefore they get like 40 withholding
taken out immediately.
And, you know, so there's just
a lot of friction and pain points
on, on either side.
Right.
And that's kind of what we're
trying to resolve.
So how does it look like for a pilot?
Right?
Is it just essentially like a
pool of pilots?
Like, you just put your name
in there and then say, I have I own
citation latitude.
All right, cool.
So I go on your website, I
type in citation latitude pilots,
and just every single person
that has a latitude current type
rating will pop up.
Or can you, like, search it
like, all right, I want a latitude
pilot with 5,000 hours in type
or 20,000 total time or that lives
in a special location.
Yeah, so.
So we took a very different
approach to this than.
Than other folks have.
Right.
And there's obviously, you
know, there's a lot of different
people who've tried to solve
this problem.
Right.
It's not a unique problem.
Everyone is just kind of
approached in a different way.
And so we've taken the, you
know, we want to kind of handle the,
you know, help you handle the
thing from beginning to end on a
trip by trip basis.
So the way that it works from
a pilot's perspective is it's totally
free.
You just kind of go, you sign
up, you fill out your profile, and
the Profile is designed to be
able to help you kind of showcase,
you know, your professionalism
and your experience.
Right.
Like, and this is a whole kind
of sidebar.
But, like, you know, hours has
been used as this proxy for professionalism
forever.
Right, but it's a terrible proxy.
You know, like, we all know
people who have 10,000 hours who,
like, we'd rather not fly with
again, and people with 2,000 hours
who are extremely professional
and on time and great and familiar
with SOPs and all that kind of stuff.
And so, like, how do we
showcase the whole pilot?
And that's kind of what the
profile is meant to do.
Right?
So it covers all the basics,
all the regulatory, like, search
ratings, type ratings and
everything like that.
You know, front and back, your
pilot's license, it covers your hours.
We've got a new, like, logbook
upload for.
For people using foreflight,
or we'll build one for, you know,
Garmin pilot and, and log 10
pro and all that kind of stuff.
If somebody has, like, an
example of one, just send it to me
and I'll figure it out in a week.
But, but also, more
importantly, like, you've got, like,
a credentials page.
So if you're a NBAA is the
National Business Aviation Association.
If you've gone through their
CAM program, you can put a, you know,
your credential in there for that.
If you're a master aviator
from Flight Safety, you can do that.
If you're part of the wings
program, you can do that.
If you've done UPRT training,
you can do that.
Right?
Like, all those little things
that, like, differentiate you as
a professional is stuff that
we want to capture.
Right?
And so a lot of those things,
like, I didn't originally have built
in, but somebody was just
like, hey, can I, like, showcase
my cam, you know, certificate?
I'm like, great idea.
Yeah, let's go do that.
And then, you know, we've also
got, like, stripe integrated.
And so when pilots sign up,
they fill out a structure Stripe
Connect account.
So they register as either an
independent contractor or as their
own business entity.
And so then that means all the
payment will, like, flow to the right
spot.
But yeah, so, you know, it's
essentially free to sign up.
You know, you put in all the,
you know, aircraft that you're qualified
in, and then, you know, based
off of, you know, the aircraft you're
qualified in, your current in.
That's what will notify you
when a trip is created.
And then, you know, pivoting
over to the operator side, you know,
operators create, you know,
Their fleet.
So like we've got a jetnet
integration so they can just type
in their tail number.
It pulls in a bunch of
information about the plane.
And then when they need a
pilot for a trip, they just quick
create the itinerary.
You know, it takes like 30
seconds or whatever sends out to
all the, all the pilots.
You get an email.
If you're not available,
you're not interested, you can just
ignore it.
If you are available and
you're interested, you can go and
provide a quote for your services.
Right.
So you can say, this is my day
rate, this is my travel day rate,
this is how many travel days I need.
This is what I anticipate for,
you know, hotels and ground travel,
travel and airline tickets and
all that kind of stuff.
And you submit it and then,
you know, we provide operators with
a dashboard where they can see
all the pilots who provided quotes,
verify their information
against the FAA's database, review
their profile, you can chat,
you can send messages and documents
and stuff like that back and forth.
And then when they've decided
on somebody they want to hire, they
can click hire, sign a pilot
services agreement digitally, which
is something that
unfortunately often gets skipped
and you know, leaves both
parties up for issues in the future.
Yeah.
And then, yeah, payment
processing happens through stripe.
So the pilots kind of get
paid, you know, automatically like
immediately for, you know, one
day of pilot services.
And then after the trip is
done, they upload their expenses
and get paid out in full.
Nice.
In building this and your
whole process, you know, you learn
different things, but in
military, I'm sure you learn things
that helped you out to do
other things.
But this seemed like a
completely new world for you.
Obviously you mentioned when
you're younger and in high school
you had kind of the magnet
school and you had the opportunity
to see kind of tech and what
it was doing.
But was it.
The question I'm getting at
was was it more difficult for you
to pivot into aviation in the
military or to pivot from aviation?
From flying and managing to an
app and being in the tech world.
Yeah, I would say that this is
more of a challenge.
I wish that wasn't the case, but.
But, but it is.
Yeah.
So I mean, I'm a non technical person.
I'm getting smarter every day.
Yeah.
But you know, I'm fortunate to
have a really great CTO who is been
on this journey with me from,
from day one.
And yeah, he can build anything.
I just kind of got to point
him in the right direction and.
But yeah, no, I mean, it's It's.
It's tough, but it's.
It's the most, you know,
rewarding thing that I've probably
done in my professional
career, including all the.
All the time I did in the military.
Yeah, it's something cool to.
To build something yourself, right?
To have, like, your own thing.
I've gone through that with.
I mean, with the podcast,
obviously, but even the podcast,
to me, still feels like more a.
Of.
Like a hobby, right?
Like, it feels more of.
Like, anyone can start a podcast.
I know.
Anyone can start an app, too.
But when I started the
magazine, like, for some reason,
my brain.
That kicked off, like, all
right, this is, like, legit.
This is.
This is real.
Yeah.
So it's really cool when you.
When you put a lot of hard
work and time and build something
that's really cool.
And it's also really scary, right?
Like, I mean, I remember the
first time I released there, when
I released this on December
15th, I was like, I.
This could go one of two ways.
No one orders, and they laugh
at me or people order, and they're
just like, holy crap.
This is actually awesome.
Awesome.
And I see why you made this.
So as a founder, as a creator,
you can only hope for.
You know, they say that and they're.
They're impressed and love it
and see the usefulness of it, but
you really don't know.
You could spend your whole
time building something, and people
are like, what the heck are
you doing?
Why would you do that?
No one wants that.
Dude, I get it, man.
That's what keeps me up every
night, frankly.
Because.
Yeah, no, I mean, you know
exactly what it's like, right?
You.
You're putting yourself out
there every single day, right?
And, like, especially, you
know, like.
Like, you or I were.
You're kind of like the face
of the thing that you're.
That you're building, right?
Like, all that responsibility
and all that pressure kind of like,
you know, gets put on your
shoulders and everything like that,
right?
When somebody has a bad
experience and there's, like, a little
bug which happens, right?
Like, we're.
We're putting out, you know,
new code every, you know, couple
days, if not every day, like,
little things come up and there's
a little bug, and I, like,
take it personally.
Like, I feel bad, right?
Like when I get an email from
somebody and.
And, like, you know,
fortunately, everyone has been, like,
super nice, and, like, they'll
send a very polite email, like, oh,
hey, like, this button isn't working.
I'm like, shoot.
Okay.
So sorry, man.
Appreciate it.
We'll get it fixed, you know.
But yeah, no, there's.
There's a lot of pressure, but
I wouldn't have it any other way.
I enjoy it.
I think it's important.
So.
It's also crazy how expensive
things are, right?
Like, I mean, with the
podcast, I had sponsored.
I had money bring it coming in.
And then when you start doing
stuff like this, like, for me, like
shipping expenses or just out,
unbelievable printing expenses, everything
like that.
But just going from like
seeing, having, seeing where the
money goes and then it's gone.
You're just like, oh, wow, I
really need this to do well.
I really need people to like
this to make this work.
And then maybe you start
getting some money back, then you
do it.
Like, in my case, it's quarterly.
So I release magazine.
A lot of expenses.
And then some people buy the
magazine, recoup some of those expensive.
Then I have to make another magazine.
Expenses are good.
You know, it's just, it's just
like constant cycle and it's just
really funny to see kind of
the ups and downs of your, how your
brain kind of manages that.
And you're like, oh, this is awesome.
You're like, oh, God, my gosh,
this is stressful.
Oh, my gosh, this is awesome.
Yeah, no, it's the sine wave
of the, you know, we're so done.
It's so over.
We're so done.
It's so over.
Just like on a daily basis, essentially.
Right?
If my morning is great, that
means my afternoon's going to be
terrible.
And if my afternoon's, you
know, great, my, then my next morning's
going to be terrible.
Right.
With this app, what would make
you most, like, excited?
Like in 60, not in 65 years,
when you retire, when you step back,
when you look back on your
legacy, when you look back on what
you created, what would give
you the most joy?
Would it be making this app
and just having someone be like,
hey, that, like, really made
my life easier.
It really helped me.
Would it be selling it to
private equity for millions of dollars?
Like, what would make you the
happiest and sleep best at night?
It's a great question.
So, yeah, I mean, I would say
that, like, you know, if, if this
can play like a small part in
increasing, you know, professionalism
and safety in business,
aviation, community, like, that would
be extremely rewarding to me.
Right?
Because it's, it's, you know,
it's unfortunately like a pretty
hit and miss, like, industry.
Right.
And like, you know, I've, I've
talked to a Lot of people about this
here, here lately is that, you
know, the airlines obviously have
like, a phenomenal track
record of, of aviation safety.
Right?
And, you know, no offense to
the airline pilots, right?
It's, it's not that, like, the
airline pilots are like the most
amazing pilots in the world.
It's that they're easy now.
It's that, like, they, they,
they operate within an organization
that has standard operating
procedures and also adheres to those
standard operating procedures.
Right?
Because if, you know, if you
don't, you're going to get a call
from the union or the
Professional Standards Board or whatever
that's just like, hey, man,
like, why were you 2,000ft per minute
inside five or, or whatever, right?
Yeah, you know, business
aviation just doesn't really have
that.
Right.
Like, there's, you know,
NetJets obviously is like, you know,
has a larger fleet than
American even, I think, these days.
Right?
So, like, large organizations
like that are able to have like,
you know, flight data
monitoring programs probably, and
all that kind of stuff, and,
you know, pretty strict adherence
to standard operating procedures.
But again, you know, most
flight departments, I think it's
like, I don't know, 60 or 70%,
like, only have one aircraft.
Like what?
Like, they don't have the
resources to be able to, like, actually,
you know, you know, implement
programs like that.
And so it just unfortunately
ends up falling on the individual
pilot.
Like, is that pilot, like,
acting like a professional pilot
or are they just kind of like
going out there and like, freewheeling
it?
Right?
And, you know, we've got a lot
of work to do, like, with just within
flying company and in the
industry in general.
Right.
But, you know, NBAA just put
the standard operating procedures
that they have been developing
over many, many years as just a free
resource for flight
departments to be like, hey, please
adopt this, right?
Like, you know, spread it around.
Make sure your pilots are
familiar with these.
Right?
Because this is going to be
something that we can kind of like
use as an industry to
standardize to a certain degree and
now, like, flight safety.
And I think CAE are going to
be integrating that into do all their
like, you know, initials and
recurrent trainings here within,
like this year.
And that's like a strap, a
step in the right direction, you
know.
And so, like, we kind of took
inspiration from that and now we've
got like, a knowledge quiz
with Inside Flying Company where
pilots can volunteer to like,
go out and like, you know, answer
this quiz on the NBA standard
operating procedures to just show
again that, like, hey, I'm a professional.
I take this seriously.
I know the standard operating
procedures and, you know, I've, I've,
you know, done this, done this
quiz and everything like that.
Right.
So, you know, anything that we
can do to kind of like, you know,
move the industry into that
direction, I think is important.
Love it.
Well, dude, I appreciate it, man.
I wish you all the best and
everything you do, and it's, it's
really cool.
I mean, it's one of the reason
why I started the podcast, one of
the reason I started the magazine.
It's just to share these
unique experiences.
I've never talked to anyone
that flew special operations in the
military.
No one.
Like you said, you didn't even
know it was a thing until it showed
up on your drop.
Right.
So it's cool to show insight
and someone could be listening today.
Be like, wow, wow, I can fly that.
Like, that's kind of cool.
Or they could.
Maybe they.
Who knows?
They were at Barry Aviation
and they saw the Dornier.
Like, oh, I really wondered
what those planes do.
Granted, it's a little
different than what you do because
it's a contract, but, you
know, get an insight of what that
could actually, that life
could be like.
So I appreciate you coming on.
I appreciate you sharing that
information about the flying company,
and I wish you the best of luck.
I could.
I. I would imagine it's so
much easier for a pilot to use the
service, and it's also
probably easier for a company.
So if anyone I know that has a
plane, I'll be sharing that information.
And if anyone here that's
listening to this, like, hey, I want
to sign up.
What would they do?
What should they do?
Oh, dude.
Well, man, thank you so much
for, for having me.
This has been, you know, a lot
of fun.
Yeah.
So flyingcompany.com pretty
easy domain or member.
So you can go up there, you
know, click register at, sign up
as a pilot, fill out your
profile again.
It's totally free.
You're also, like, you know,
you can find me on, on LinkedIn,
Tyler Flag.
You know, Twitter.
I'm just now kind of.
Or X, sorry, just now kind of
getting, getting into that Tyler
C. Flag there.
You can also send me an email.
Tylerlyingcompany.com Again, I
love to hear from people.
Most of the really good ideas
have not been my brainchild.
Right.
It's been people coming to me
being like, hey, can you add this?
And I'm just like, yeah, I
don't know why I didn't think of
that myself.
Great.
Idea.
Let me go do that.
Yeah.
And then I hand it off to my
CTO and I'm just like, please build
this thing.
Um, but, but yeah, I don't know.
Please.
I, I, I love, I love talking
to people.
So, you know, by all means,
reach out.
Cool.
Well, Tyler, appreciate your
time man.
Thanks for coming on.
Thanks dude.
Appreciate you.
That's a wrap on episode 355.
Thank you so much for listening.
I really do appreciate it.
Tyler, shout out you man, for,
for coming on the podcast, sharing
your story.
And I always love when
someone's building something.
So if you're building anything
in aviation, trying to make aviation
better, hit me up.
We'll always do a podcast.
We'll always talk about it.
If you haven't bought the
magazine yet by now, we have completed
volume two.
By the time this comes out, we
are hoping for an end of March release.
So that will hopefully be
closer to April Fools.
Which is kind of weird to
release something in April Fools,
but maybe it'll be our thing,
you never know.
So if you see charge come out,
I know a lot of people that did buy
in the first day.
It's a quarterly recurring so
you might get charged on 3:15.
But do know the magazine will
not ship until a couple days after
that.
I will craft an email and make
sure everyone knows that.
But AV Nation, I hope you are
having a great day.
I am going to try to go get
over this cold.
Got to go fly soon but got to
get better.
But appreciate you guys and as
always, happy flying.