July 23, 2025 • 38 mins
In this episode, Adam chats with Raj Shah about his diverse journey in aviation and beyond. They discuss Raj's transition from the Ivy League to the Air National Guard, his early military tech experiences, and his shift to entrepreneurship in cybersecurity. The conversation covers the founding of the Defense Innovation Unit (DIU) and its role in linking Silicon Valley with the Pentagon. They also touch on military budget strategies, balancing legacy systems with new tech, and future cost reductions. Raj wraps up by sharing insights on returning to flying and his venture with Shield Capital, offering advice on finding purpose after military service.
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Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
(00:16):
Welcome back to the Pilot Network podcast, theplace where we connect aviators with the tools,
resources, and stories to help them navigatetheir careers and lives.
I, as always, am your host, Adam Yuhan, and Ihope wherever you are on this pale blue dot,
you are flying the line, sitting at home orenjoying some time out in the wild other than
(00:38):
working.
Or I guess if you're flying the line, areworking, but you're flying safely and having a
great day doing it.
Anyways, today's guest is someone who'soperated at the intersection of national
defense, cutting edge tech and service aboveself.
My good friend Raj Shah is an F sixteen fighterpilot with more than two decades in the Air
National Guard, and that's just the tip of theiceberg.
(00:58):
He's the co founder and executive chairman ofresilience, a company that fuses cybersecurity
with insurance to help organizations go beyondrisk transfer and become truly cyber resilient.
Okay.
I don't understand what that means, but that'sin my little script.
Dude's a genius.
He's also the managing partner at ShieldCapital investing in the kinds of frontier tech
that push national security forward.
(01:20):
He actually looks at what the future is goingto be or needs to be, and he moves the needle
that way in defense.
He's also a former managing partner of theDefense Initiative Unit at the Pentagon, one of
the few people can say they've led meaningfulinnovation inside the five sided building.
And I know for a fact that he's done that.
He helped out with some really cool stuff inthe tanker community while I was there and it
(01:43):
still shows up to this day.
Raj is also the co author of How the Pentagonand Silicon Valley are transforming the future
of war.
This is a book that digs into how we canaccelerate innovation in defense by working
smarter, faster, and with the best minds acrossthe industry, government, and academia.
It's a must read for anyone who wants tounderstand where defense innovation is going
(02:05):
and where it needs to go.
When I picked this up, I thought, oh, it's abook by my friend.
I don't know how enraptured I will be, but Icouldn't put it down, it was fantastic.
I actually want to read it again, and it taughtme a lot more than just about that intersection
of defense and technology and how the Valleyand the Defense Department didn't have that
(02:29):
perfect bond anymore.
It was such a great book and I really, reallyenjoyed it.
Raj is, it's not done yet.
He's also taught at Stanford.
He's launched and sold a startup, served onboards that span healthcare, education,
national security, the list goes on.
He's also been quietly empowering the nextgeneration through deliverance of 200
(02:50):
scholarships per year to women in rural India.
The dude does it all.
Our conversation starts off with how Raj gotinterested in aviation, how that changed and
molded his career as he launched into all theseother different amazing categories.
Anyways, I'm sure you want to hear more fromme, but let's hear from Raj.
Altitude.
Altitude.
(03:10):
Pull up.
Pull up.
Pressing.
Pressing.
Warning.
Warning.
Bingo.
Bingo.
Lock.
Lock.
Chaff.
Flare.
Chaff.
Flare.
Out.
Chaff.
Flare.
Low.
Jammer.
Jammer.
(03:31):
Raj, what's going on, man?
It's been a while since we've been able tochat, and this took literally, like, four years
to get this thing organized.
Absolutely.
Good to see you, Adam, man.
Yeah.
You too, bud.
In the intro, you heard all about how Raj isthis great, amazing, human being pilot and,
entrepreneur.
Yada yada.
The the list goes on and on.
But what Raj is to me is a very good friend.
(03:51):
We go back twenty about twenty two years,twenty one years now, twenty two, all the way
back to Vance Air Force Base where we learnedhow to fly the mighty T37.
But I had a much different story when I gotinterested in aviation compared to Raj.
What drove what drove you to that?
Because I I know your background, and we'll getall to that stuff.
But, like, what drove you into aviation,especially military aviation?
(04:13):
I think, like, like a lot of, little kids thatend up in the air force, I never grew up.
I loved airplanes since I could imagine and,you know, and and never shook that.
But I think more importantly, you know, youdon't join the Air Force just to to fly.
Join to serve.
And, you know, I, am the kid of immigrants.
(04:34):
My parents, came here from India in the earlyseventies, and this country had been, you know,
just fantastic to our family.
Me and my sisters got to, you know, go toamazing places for, undergrad, and most of my
family now has come here, extended family.
So I wanted to I wanted to serve, and the AirForce said I could serve and fly jets.
(04:55):
So I said, Sign me up.
It's funny because you're you are what weaffectionately call guard baby.
Right?
Like, you're yeah.
You started out the smart way.
I remember when I met these guys in pilottraining.
They're like, oh, you're active duty.
I believe, you and a couple others said, ah,Adam.
Guard guy and an active duty guy's body.
And they're right.
So and I won't let I wanna have to share youralma mater, but I will share that it's
(05:18):
somewhere along the Eastern Seaboard and it'sthe it's got what they would call ivy growing
all over the place.
In that world, how does one go from that worldto like, I'm gonna be a guard baby?
Because you don't see that very often.
And I think that's intriguing to a lot ofpeople, especially me.
Well, I'm glad you finally found the light andcame over to the guard.
(05:40):
Took you a few years and some detours.
Everyone wizens up.
Yeah.
You know, hey, dude.
Give me a break.
I was always a slow learner.
You know, I decided, I think, too late when Iwas in undergrad that I I wanted to go down the
flying path, and so I I wasn't able to miss outon the ROTC path.
And, you know, I had I grew up in Warner Robinsin Georgia, and I had a lot of most of my
(06:00):
friends in high school, their parents served inthe Air Force.
And so one of my good friends, his father was aan Eagle pilot and, was talking to him, and
he's the first one that told me about theguard.
And so I found the only and closest, fighterunit to in Jersey, and I went down and visited
them and got to know some of them and thoughtit was a really interesting path that would
(06:23):
allow me to to serve, but then also, you know,explore some of the other things I wanted to
do.
But as you know, it's it's a very uncertainpath, and this military service is brand new to
me and my family.
Like, no one in my family had ever served inthat military either here in The US or India.
I actually ended up enlisting in the JerseyGuard, I think, my sophomore year of college,
(06:46):
and was, I picked the only specialty that wouldhave allowed me to go through training over the
summer.
So I was scheduled to be an admin person in thesquadron.
And You'd fit right in in that world for youshould have done that for a career.
I think that would've that as soon as you
I was ready to do it.
Was like, no matter how this flying thing goes,I'd love to serve.
And yeah.
So so I was there, and then I had my bagspacked to go to basic, and they had a a pilot
(07:11):
board.
And they're like, well, you should apply.
You know, you usually don't get in your firsttime, but I was like, okay.
It'll be good practice for, you know, after Igraduate.
I just got really lucky that I ended up gettingselected.
And then the squadron was like, well, we haveto send you to a training school, AMS, you
know, at the time.
So why don't you not go to a basic and, justwait?
So I was, you know, I was enlisted in nameonly.
(07:33):
I was like, was it for two and a half years,but never actually went to any any training.
Wasn't any help help.
But, you know, it goes back to, I think, forthem, the fact that I think he was willing to
to sign up and actually take the oath, I think,meant a lot that, hey.
This guy's actually serious about the serviceside of it.
I I would say so I'd I have a conversation witha lot of pilots, you know, who wanna fly
airplanes.
They say, hey.
(07:53):
If you have a service bone in your body, it isquite gratifying for more than just the reason
of you can fly cool jets, go cool places.
There's a lot there that is not it's anextrinsic motivator, I think, for a lot of us
while we do it.
A lot of really successful, great people whoyou would not otherwise believe served their
(08:15):
country one way or another, but a lot ofmilitary service.
As your military service kind of kicked off, wewent through training together, you go, you
know, the B course and all that good stuff.
You come back and I remember this was kind ofmy introduction to you knowing way more about
stuff than I thought we knew.
Because I mean, pilot training, there wasn't alot of talk about anything other than what
(08:35):
we're doing at pilot training professionallyand then what was happening on Friday and
Saturday nights.
Like, those were the that was in crux of prettymuch everything that was going on there,
especially for a simpleton like myself.
We won't get into what those those nights,entailed on this podcast, will we?
No.
We won't.
That's a you that is I will gladly buy people aa drink or they could buy me one if they wanna
(08:58):
have that conversation.
More than happy to get into it in person.
That is what for that is what the hanger fliesand the TPN chapters are for.
So if you're interested, you gotta show up tothose things.
Anyways, what I noticed was you you wrote thisarticle, and I don't remember I can't remember
where I saw it.
I I don't know if you sent it to me.
I think you might have sent me a link orsomething.
But you had deployed, and you were taking somepretty cool pictures when you were flying and
(09:24):
you were also writing about some of thetechnological side of what you were doing,
stuff that I didn't understand, not onlybecause I wasn't a fighter guy, but also
because I was kind of adult.
And when I put those two things together, waslike, woah.
You know, this is kinda cool.
Where did your where did that interest spark?
Because this will come up much, you know, laterin your career where you really got really got
(09:46):
involved in the innovation technology space.
Where did that kind of confluence start tooccur?
Was that like right away when you showed up inthe military or was that before or did it start
happening when you're flying the, the wonderfulf 16?
Well, I think I've always had an interest in inin technology.
I mean, I started off as an engineer and thenrealized I wasn't smart enough to be an
(10:07):
engineer and became a public policy guy.
But, I think, all of us have grown up in thisworld where the technology that we had to go to
war with on in some sense was amazing.
Right?
Amazing performances in an airplane andweapons.
Yet, it was walking into the stone age at thesame time from your software standpoint.
(10:29):
Right?
Like, your phone was more powerful than all theavionics in your in in the jets.
And so I think, for all of us, we sort of sawthat.
And for me, the first visceral time was thiswould be o six, my first tour in Middle East,
in Iraq.
And, you know, I'm just a young wingman andtrying to make my way through and do things
(10:51):
right, not get in trouble.
And most of our missions or many of them weresupporting troops on the border between Iran
and Iraq, and we're doing a cast wheel overthem.
And at, you know, 400 knots, you know, you'retraveling pretty fast, but there's no moving
map.
And, you know, you know, you don't wanna gointo Iran too far.
You know, maybe they'll shoot at you or createsome international, but, you know, god forbid,
(11:13):
the general finds out and then, like, sends youhome from the warp.
Like, that could be it could be nothing worsethan that.
And, you know, I'd that same year, of course,we could rent a a Cessna back home.
And the predecessor to the iPad, an iPac, youcould rent you could put a $100 piece of
software on there and have a moving map.
And so a couple of us downloaded the maps forThe Middle East, put it on there, and the the
(11:38):
good news about a single seat airplane is thatif you decide to bring your iPad with you, that
no one else Print data.
So someone was fluent that, and I could lookdown at this thing and know where I was.
And so that was, like, kind of the first realvisceral example to me of of how how these two
different systems of technology development andprocurement had diverged and were and the
(12:00):
divergence was accelerating.
Yeah.
It spot on.
I remembered, on the other side, the taker sideis, oh, we got this great new thing.
It was called Block 40, and it's got, CPDLC andall this cool whiz bang stuff.
And I was like, I don't know what any of thisis.
I remember the most exciting thing I was isthey took the radio head out of the side down
(12:21):
by my right leg for the HF, and they put itinto the actual box where I could type in a
frequency.
And I thought this was the coolest thing I'dever seen in my life.
Little did I know that this is not that big ofa leap in technology and that we had much worse
problems in the jet that I didn't understand.
And that being part of it, like, although we'renot moving around that fast, we are moving a
(12:41):
lot of airspace, a lot of different airspacesegments when we're flying over and above
combat zones.
And when you don't necessarily you know whereyou are on the map that you drew with some lat
longs, which is better than the stuff you guyshad, but you can't see it on a map.
You can't see it on a digital read orForeFlight readout nowadays where you go,
(13:02):
that's the border of Iran.
Don't come close to it or that's there.
It was not we we weren't there yet.
And I think I I don't think I owned an iPaduntil about 02/2008.
So I was behind the times a little bit before Igot into that world.
When you saw that when you had this sense of,okay, we're we're behind in our software, our
(13:26):
some of our hardware stuff.
I mean, obviously not the stuff that goes boom,but the stuff that we can actually use to,
prosecute the mission on the back end, iPads,etcetera.
What was your first step into the idea of,like, you know what?
I think I can I think I might be able to Ithink I might be able to change some of
know, at the time, I didn't think I didn'tthink there was much I I could do?
(13:47):
Right?
Because, you always believed, hey.
There's some smart group or team somewhere inthe Air Force that's, like, working on this.
We're in the in the military.
But, you know, it did it's something that thatstuck with me.
And so after my, whatever, six years of fulltime there, I, you know, I became a traditional
(14:07):
guardsman part timer there at the base, keptflying, went through business school, became a
consultant, but, you know, realized I reallyliked early stage entrepreneurship, building
teams, and solving problems.
And so I met a couple of smart guys out of theNational Security Agency, some of our best
attackers, hackers, and said, you know, howwould you stop yourself?
Because as much as I love a hoarder makes tocome over the horizon and they call me to go
(14:30):
shoot them down, like, that's not the majorthreat, facing us.
Right?
It's guys on keyboard, hacking things.
And so we ended up doing an early stagestartup.
Right?
Started in the basement of a townhome inMaryland and, you know, started building
technology, and I was the only guy thatcouldn't write code, so I I did everything but
write code from flooring lunch to raising moneyto trying to sell this stuff.
(14:53):
So, ultimately, we we grew the business.
And, you know, we knew what we were buildingwould have been valuable to the government
because that's where our team was from.
But I think after my, like, eighth meeting withsome random general, we just said enough.
Like, it's wasting time as a start up to try tosell to the DOD.
Our investors even told us, hey.
(15:14):
Don't sell don't work these guys.
They're just gonna slow you down.
It's actually gonna lower your valuation.
And so, ultimately, the company ended up beingacquired by a big public company, and we had
zero sense of government revenue when when wesold it.
So here I've now seen both sides, right, as theuser not getting access to modern technology,
but then as someone helping to build tech,seeing just how hard it was to work with the
(15:38):
government.
And, you know, after selling it, I had to restinvest there for two years.
I was presented with the opportunity to try togo and fix that.
And that was that was helping stand up thisthing called the defense innovation unit.
And, you know, that's the real time when Isaid, okay.
I could actually go and try to solve thosethings that, you know, it was a decade before
(16:00):
with that deployment.
Yeah.
I could help build a team to go and solve theproblems that frustrated me when I was a when I
was a young captain.
Yeah.
I remember this phase because we would talk,like, occasionally.
Maybe, you know, six months, year, somethinglike that.
Just catch up, blah blah blah.
And you're telling me, not in detail, justlike, oh, yeah.
I got this going on, that going on.
(16:21):
I'm like, dude, yeah.
That's cool.
I have no early earthly idea.
It's funny now because I'm doing some work witha buddy of mine on a startup and man, you're so
right.
I'm trying to work with the DOD on certainthings.
There's a lot of people who want it, but to getto the end product and getting it in the hands
of the warfighter is very, very difficultunless you have something that's really great
(16:43):
and sponsored by the right person.
It's very challenging.
So I can't imagine what it was like before DIUcame along.
Mentioned this in the intro, the book that youended up authoring is where I got a lot of my
information that I pieced together my friend'sjourney.
So you start DIU, which was DIUX back then,right?
(17:06):
Defense Initiative Unit Experimental.
With this idea of we're gonna bridge this gapbetween what Silicon Valley and the tech
wizards are doing on the outside and what thedefense needs are on the inside that we know,
especially you, because from a tactical andstrategic point of view, we're not just
strategy.
(17:27):
Back then, and you mentioned this in the book,that the Valley was not real keen on military
support at the time.
And, that to me seems like even a bigger hurdlethan trying to plow in through the DOD to get
somebody to buy what you're trying to sell.
How did you guys even start that process?
(17:49):
Yeah.
Yeah.
So you gotta think back.
So the founder of DIUX, was secretary AshCarter.
Right?
This was his brainchild.
In fact, in 02/2001, he wrote a paper when hewas still at Harvard about how commercial
technology would be decisive on the battlefieldof the future.
Robots, AI, drones, all the stuff that'sobvious now post Ukraine.
(18:09):
But, you know, he thought about it in 02/2001,and then fifteen years later, he's now
secretary of defense, and he goes andimplements his, his vision.
And I think what made him successful andultimately DIU successful is, you know, there's
a lot of people that have visions and havegreat ideas.
There's very few that can actually go and thenexecute on that.
And I think Carter had that unique ability todo both because he'd already been in the
(18:34):
building.
Right?
He was the deputy secretary.
He was the head of acquisitions.
So, like, he knew how the place worked.
I remember sitting in meetings with him wherehe'd have some idea.
Like, we should go do this.
And then the staff would come in like, hey,sir.
You know, we can't do it for this reason, thatreason.
And he'd be like, bullshit.
I know you can.
Go find somebody that go get it done or I'llfind somebody that will by next week.
(18:54):
And he knew the difference between what waslike a policy and a regulation that could be
run over and what was law and what was actuallypossible.
And so that, I think, made him really unique.
And so he started it.
He he was the first sitting secretary to comeout to Silicon Valley in, like, thirty years to
talk about this, idea of a of a partnership.
(19:16):
And you're right.
At that time, it was it was a challenging timefor the Pentagon to work, and interact with
folks in the Valley.
You gotta think back.
If you look historically, the Valley wasstarted because of the military and to solve
national security problems.
Right?
It was started many of the the early effortswere to solve radar issues in World War two.
(19:36):
Right?
How do we catch German, bombers trying to dropbombs on in London, and how do we the
electronic warfare side.
That's the start of it.
The first satellites were here, were builtthere, ICBMs, like integrated circuits.
So it was there.
But then, you know, the world diverged in thatso much more of the r and d was commercially
(19:58):
oriented going after this huge commercialconsumer market.
Right?
IPhones, cloud, etcetera.
And so those things diverge.
And then, of course, then there's the the, youknow, some of the philosophy stuff.
So when he came out there, this was right afterthe Snowden revelations.
Right?
Ed Edward Snowden talked about what the NSA haddone, and, some folks out there thought the,
(20:19):
you know, NSA was just as bad as the Chinese interms of of of spying.
And you started this kind of tough spot.
But the real problem, right, and the real issuewas, I think, less philosophical, right, like
anti war, anti government, but just business isa business.
Like, it was just too hard to work with thegovernment if you're a start up.
Right?
A start up has to raise money every eighteenmonths to stay alive, and so you need to show
(20:43):
progress, like selling to customers.
And if it takes four years for your customer tobuy something, which is the average contracting
times for the government, then it doesn't makeany sense until you're like a really big a big
company.
And so I think changing that and finding a wayto get companies on contract quickly to talk
about our problem sets was what DIUX's missionwas.
(21:05):
And I'll tell you all my battles weren't out inthe valley.
They were in DC.
Yeah.
I ended up having to fly there basically everyweek, taking a red eye and a middle seat coach
on United first to go and, like, battle in thePentagon or battle on on Capitol Hill on for
our budget and, and begin to change.
And this is where, again, I give so much creditto secretary Carter and then secretary Mattis.
(21:27):
Those are the guys I worked for.
Is that, like, he he just gave both of themgave me so much authority and leeway and trust.
I mean, we even had this thing where we couldask for an exception to any regulation or
policy that we thought were getting in our way.
And then they had to come up with anadjudication in that group within, like, ten
(21:48):
days, and all negative adjudications had to besent directly to the secretary.
So I could just, like, walk around thePentagon.
Was like, you don't wanna do this.
It's gonna slow you down because it'saccreditation problem, whatever ATF.
You wanna tell the secretary or do you want meto tell them that it's get slowed?
They're like, you know what?
We can I think we can get it done?
Oh, okay.
Yeah.
Amazing how that works.
Wait.
That's that's the thing.
Like, bureaucracies are such a pain in thebutt, but the good news about a bureaucracy is,
(22:11):
like, one person at the top.
And if that person says jump, then everyonedoes.
And this is where I think leadership reallydoes matter, and places like the Pentagon can
be reformed.
And, of course, you know, now ten years later,it's just a it's just such a different place to
do business with.
And speaking of that, so, like, you've seen theevolution of DIU and how it integrates with the
Pentagon at large.
(22:32):
And I've seen it from a different perspectiveworking with my buddy on this startup, seeing
how, you know, going through, like, the thesmall business, cyber phases, all that kind of
stuff, awards.
Still seeing that, yes, even with all thischange, there's still a lot of improvement that
can be made on some other levels.
But as far as DIU and DOD go working together,what have you seen?
(22:55):
Because my understanding of DIU is it's, yeah,there's a lot of software, but it's also
there's a lot of hardware tech stuff that like,and stuff that's employable essentially
rapidly.
This isn't something that's like, oh, yeah, insix years you're going to be able to do this.
Every aircraft ever purchased for the UnitedStates government has been like, oh yeah, yeah,
(23:17):
like in six years this thing's going beamazing.
And then it's that.
So that evolution from where you started towhere we're at today and going forward, how do
you how did you see that unfold?
Yeah.
No.
It's it's remarkable what the organization'sdone, and I give it a lot of credit to my kind
of successor.
So Mike Brown ran it for four years after me,and then Doug Beck has run it for the last two
(23:38):
years.
Right?
We've all known each other for a long time, andthey've done amazing work.
So there's a lot of there's a couple ofdifferent ways you can try to measure success
and impact.
The government, of course, money talk.
So, you know, budgets matter.
I think my budget in that year one was, like, Idon't know, $1,820,000,000 bucks.
This last bill that just passed, DAU got a$2,000,000,000 plus up.
(24:00):
Wow.
So, you know, now that's real dollars.
Still, I don't you know, in a $800,000,000,000budget, it still feels to me like it's kind of
a rounding error, but you can get a lot done.
And then from a a mission impact standpoint,right, publicly, they've been working on this
effort called Replicator, and now they havesomething called Replicator two, which is
really how do you get, autonomy to supportcombatant commands in the warfighter,
(24:25):
particularly out in the Pacific, at a speedthat matters, right, to to deter any sort of,
you know, invasion or military action in theTaiwan Straits.
And so they're building all kinds of differentdrones on the sea and in the sky and moving
really, really fast.
And so I think there's immense mission impact.
Right?
It's not, you know the the level of that impactto, like, solving my iPad problem is, like, you
(24:49):
know, just two totally different differentlevels.
So it's, you know, it's great to see.
And I think more importantly, it's those tools,those techniques, that approach should infuse
across the department.
Right?
You just don't need one organization doinginnovation.
Right?
This is how the whole play should operate.
And I think you're beginning to you'rebeginning to see that, at the services level
(25:10):
and at other co comms.
So when you say kind of services and the COCOMsand stuff like that and DIU being a DOD
supportive investment, when you're talkingabout stuff like that, how not to get into
finer a point, but the Air Force vice the Navyand Army have always had that the budget for
(25:30):
tech on the Air Force side or R and D hasalways always, but generally higher just
because of the nature of the beast.
Is the split is a split even up to people?
Is there lots of money going to the army andthe navy?
Lots of cool new things and stuff that canreally help the warfighter on the ground.
Because as I've always said to my friends,you've been like, oh, you know, you're an air
(25:51):
force guy and your friends, fighter pilots,blah, blah, blah, blah.
I go, yeah, yeah, yeah.
We're all support.
We're all support.
There's only one person that matters, that'sthe 18 year old on the ground with a rifle.
Who's that?
Yeah.
Whose boots there.
So I've always wanted to see more money, moresupport go to those kids on the ground who are
doing that the hard work.
What How's that split working?
(26:12):
Is it is it is it looking like it's we're doingthe supportive role for people that are
actually in the suck?
Yeah.
No.
I think so.
Look.
I think there's, as much as I rail on all thebureaucrats in the Pentagon, they're not ill
intentioned.
Right?
They're they're there because they believe inwhat they're doing, and they believe in,
service and and strengthening our nationalsecurity.
(26:32):
So they're trying to do the do the right thing.
You know, I think what's interesting when wethink about budgets and and money and about
innovation, you know, is that commercialinnovation, you can leverage a lot of r and d
that other people that the private sector hasdone.
So if you wanna build a a stealthy fighter jetor an aircraft carrier, like, there's no
commercial market.
Right?
Yeah.
And so there's only one buyer.
(26:54):
And so that means the government's gonna payfor all the r and d, and that's why these
things take a really long time.
And, you know, I'd say the system does an okayjob at buying an aircraft carrier.
Like, you're gonna keep the thing for fiftyyears.
You wanna make sure it's done right and haveall these requirements.
But it's it's totally ill suited for commercialtechnology that's moving so so fast.
And I think what I what's really important isthat the cost, the price points of some of
(27:17):
these things, like low cost satellites, ofcourse, software, small drones.
It's just it's just orders of magnitude.
So when I think about budgets and supportingpeople on the ground, I think about what's the
mix?
Meaning, how much is going to go to legacy typeof equipment, and how much of it's going to go
to rapid fast moving systems.
(27:39):
You know, we've all played with AI now.
Right?
We all use ChatGPT.
You can see the power of that.
Know?
What you know, how long is it gonna take for usto get that to every single soldier to
understand what's around them to be able toquery all this data, these sensors?
That's just one example.
So I think really what's important to me iswhat's the mix?
What percentage of our DOD budget is going togo towards new modern technology versus a
(28:04):
legacy stuff.
And the DOD has this, you know, unique,strategic challenge that it has to be able to
fight today.
Right?
Like, we have to go to war tomorrow.
You have to be ready to do that, and you haveto you have the equipment that you need.
But you also need a plan for ten years fromnow.
And how do you how are you going to takeadvantage of these changes to continue to have
deterrents?
(28:25):
And, you know, it has to have this right mix.
I think the mix is probably skewed a little bitstill too much on the legacy side.
You know, if you talk to different,congressional teams and, the navy, you know,
everybody loves drones and and new technologyuntil you say, let's have one less aircraft
carrier.
I'm like, wow.
And so it's a it's a complicated, a complicatedcalculus.
(28:45):
But I I get so much positive, I think, changein momentum.
And even this last build up has passed that youcan just see the dollars that are being placed
towards, again, modern technologies like AIdrones.
Yeah.
You know, I I tend to agree with you.
We pick some of this modern modern stuff up.
We actually we plan and prepare correctly.
(29:08):
The costs will come down.
I mean, it's very okay.
Let let's be realistic.
When you when somebody gets a a a $50 allowancefor the week and then you go, okay.
You know what?
We're gonna reduce your allowance to 35 nextweek.
There is gonna be some bitching complaining.
And so I don't necessarily see that, but thefuture increase when you can scale it, like you
(29:28):
said, and do it and scale correctly, we couldsee a definite shift in where that money could
be allocated if it's done correctly.
And I like you said, I mean, read the book,guys.
It is it's fantastic.
It'll give you a insight that I didn't havebeforehand, and I'm friends with Raj.
So if I otherwise, you're just making thisstuff up in your head or you're, you know,
you're reading it on, whatever website youchoose to.
(29:50):
But this gives you some real insight on whatwas going on in that historical lead up and now
what's happening now.
Speaking of now, what are you up to now?
I mean, I know what you're up to, but you wrotea book, you still fly, you're in the
entrepreneurial space, you got the family lifegoing on.
How did you you were out of the cockpit for awhile, right?
Like you stepped away and obviously you missedit.
(30:12):
So you came back.
That was I mean, that's a no brainer.
But tell me about like we we gotta talk aboutwhat job did you take and how did you get back
into it?
Because it was to me, it was one of my favoritestory.
It's one of my favorite stories of all myfriends getting back into flying.
Yeah.
Look.
I think when I, so I'd come back to my my thirddeployment, felt the taxpayers got their
money's worth out of me, and I was startingthat first company.
(30:35):
And Yeah.
You know, early stage entrepreneurship, it it'sjust it's just so hard, and it's so all
consuming because, you know, you just don'tknow what you're doing.
Right?
It's a I I would say it's like impossible to betaught how to be a CEO.
You can learn it, but you can only do it youcan only learn it by doing it.
And so there was just I couldn't I couldn'tbalance it also.
I so I I stopped flying and hung it up andthought I was I was done.
(30:57):
You know?
But then I think it was like five years later,I'm in I'm at DIU X, and I really missed,
serving.
I missed being I mean, I had stayed in theguard, and the guard is very flexible in
enabling that.
I had wonderful commanders that, you know, putup with me and allowed me to to stay in in
uniform.
And and there was a shortage of pilots andparticularly some test support kinda work.
(31:19):
And so they they offered me the opportunity togo back, and I said, let's do it.
Hell yeah.
Yeah.
Yeah.
And and and so now, you know, I'm I'm still in,and it's such a treat, like, to get to to put
the the uniform on.
Right?
Because I know there's, you know, limitednumber of days that I'll still get to do that.
So it's, like, such an honor to to get to goand do that today.
(31:40):
And so I always encourage folks that are, youknow, leaving.
I know I know this podcast is a lot of piratesand a lot of service folks is that finding a
way to to stay in whether or not you can fly ornot, but find a way to serve.
Continue is like because it's been such a bigpart of your life.
If you could make it work, I always try torecommend people to to do that.
You know, to your question of what do I do now,you know, entrepreneurship, I also think, is
(32:02):
kind of a young man sport as is, I think,flying jets.
But now I I have the, you know, privilege.
What's that?
It's young at heart.
You don't
have Young at heart.
Young at heart.
Young at heart.
Be young.
Try not to pull as many g's these days.
G's on
the old
back.
Yeah.
You know, I get the job I I have an amazing jobnow where I get to help support and work with
(32:22):
the next generation of of innovators.
So, I help run a venture fund called ShieldCapital.
We invest in companies at the intersection ofnatural security and commercial.
So four kind of core technology areas, AI,cyber, space, you know, and robotics slash
autonomy.
And, you know, we are early stage, so twopeople and a dog to, you know, maybe a team of
(32:44):
20 people.
Right?
So it's very, very early stage.
And so we invest in them, and then we helpmentor and guide and and support them and help
them learn from the mistakes that that we'dmade when we were we were entrepreneurs.
And so it's just exciting to see how manypeople now want to go and build companies
supporting national security.
Like, I've just I've never seen so many amazingengineers.
(33:08):
Right?
I think they're just bored building photosharing op you know, apps.
Like, it's just only so much fun.
And I think this generation really wants tofind meaning and do something that matters.
And post Ukraine, post Israel, you know, Ithink folks realize, hey.
There's authoritarians out there that don'tbelieve in the sort of, you know, Western
(33:29):
democratic values that we do, and having havinga force that can deter that is important.
And so you see people wanting to serve.
So it's really it's really exciting.
And I think to your point you were makingearlier, there's lots of different ways to
serve.
It doesn't only have to be in in uniform.
Yeah.
The these folks are doing great stuff.
So it's great.
I get to spend a lot of time with these highenergy entrepreneurs, and it also helps with my
(33:50):
ADD because I could do multiple things at thesame time.
I know.
I I had a conversation last night with a couplepilots that joined me on our Ask Me Anything
biweekly series in one of the where there wastalk about side hustles, whatever.
You you could become an airline pilot.
Like, hey, you got this time off.
What are you gonna do with your time?
And I said, you know, I used to say, yeah, youcan go get a job or go get into real estate or
(34:14):
create your own business, blah, blah, blah, AndI said, you know, you're gonna make plenty of
money being an airline pilot, whatever.
Don't let that drive you.
Let your talent for something that you enjoydoing, let that drive you.
It becomes your passion.
One of the guys was talking about running, bigmarathon runner type.
I said, if you don't want to start a job orstart a whole new world of business for
(34:36):
yourself, you can be kind of your ownentrepreneur on yourself and go go I mean, go
do something basic to drive and serve.
Yes.
You retired from the military.
That service bone is is that service itch isprobably not gonna get scratched unless you go
do something else.
If you don't do that something else, you'regonna be kind of wondering what it is you're
(34:56):
showing up to work for.
And then once you once you fill that up withkind of fill that cup, you'll kind of feel that
feeling of, that's what the military was givingme all these years and I didn't know that.
I've been very lucky to have TPN for so longthat I've been able to get that sometimes.
Sometimes it feels like, why the hell am Idoing this still?
But I I I love that the fact of that we'retalking about that service aspect and that's
(35:19):
kind of how it all started for you and how itcontinues to drive you to go and do this and
work with these people to help serve what we'redoing as a whole as a collective.
So, Raj, to kind of wrap up, where where canpeople find you, reach out to you, chat with
you, see what you're up to these days, and thenalso any parting shots you got for me and the
and the network out there?
(35:39):
Yeah.
Well, I'm I'm I'm easily discoverable, so youcan find me on LinkedIn or my email is just
rodjie shieldcap dot com, so I'm I'm I can befound.
And we've got great blogs and other things onour our website so you can learn about the
companies that we're investing in and and toyour point, lots of opportunities.
I mean, I guess, like, the the final, partingshot, I would say, is, you know so first, you
(36:03):
know, thanks for this opportunity, and thanksfor putting together this network.
I think folks that have spent time inparticularly military aviation, it's a it's a
special community.
It's a special tribe, and it's one where Ithink, that shared experience really makes
people wanna help each other, which is which isawesome.
But then I'd I'd go back to what you said theretoo is that coming from that tribe, you've done
(36:27):
some pretty amazing things, and there's, like,no limit to what you can do.
Right?
Obviously, you can you can fly airplanes, andyou should need to do that.
And there's lots of opportunity there.
But there's all kinds of things on the side andand transition that your skill sets and your
leadership can drive.
And as we see this just redoubling ofindustrialization here in The US and technology
(36:49):
building for national security.
I think there's those skill sets are in need,and there's lots of opportunities.
Dude, it's fun chatting.
It's been long too long.
We we gotta gotta make it more often than just,you know, once in a while.
Hopefully, we'll be coming out going out to seeRaj in in on the West Coast soon.
But I wanna thank you again for all that you'vedone for me and for what you've done for the
(37:09):
network.
For those of you who don't know, Raj is likeprobably a member like number 15 or 20.
Oh, that's that's how far we go back.
And and I I appreciate time.
I know how busy of a guy you are.
And for those of you out there who need to geta hold of me or Matt, hit us up at
heyguys@thepilotnetwork.com.
You can go to the pilotnetwork.com to findanything else about this, the podcast, whatever
(37:29):
else you need to know when we're doing ourmeetups, when we're having chats and all that
good stuff, and then sign up
for the
newsletter.
Name change coming soon.
Again, thank you all for being a part of thenetwork.
Keep that shiny side up.
Greasy side down.
Fly safe, everybody.
Welcome back to the Pilot Network podcast, theplace where we connect aviators with the tools,
resources, and stories to help them navigatetheir careers and lives.
I, as always, am your host, Adam Yuhan, and Ihope wherever you are on this pale blue dot,
you are flying the line, sitting at home orenjoying some time out in the wild other than
(00:38):
working.
Or I guess if you're flying the line, areworking, but you're flying safely and having a
great day doing it.
Anyways, today's guest is someone who'soperated at the intersection of national
defense, cutting edge tech and service aboveself.
My good friend Raj Shah is an F sixteen fighterpilot with more than two decades in the Air
National Guard, and that's just the tip of theiceberg.
(00:58):
He's the co founder and executive chairman ofresilience, a company that fuses cybersecurity
with insurance to help organizations go beyondrisk transfer and become truly cyber resilient.
Okay.
I don't understand what that means, but that'sin my little script.
Dude's a genius.
He's also the managing partner at ShieldCapital investing in the kinds of frontier tech
that push national security forward.
(01:20):
He actually looks at what the future is goingto be or needs to be, and he moves the needle
that way in defense.
He's also a former managing partner of theDefense Initiative Unit at the Pentagon, one of
the few people can say they've led meaningfulinnovation inside the five sided building.
And I know for a fact that he's done that.
He helped out with some really cool stuff inthe tanker community while I was there and it
(01:43):
still shows up to this day.
Raj is also the co author of How the Pentagonand Silicon Valley are transforming the future
of war.
This is a book that digs into how we canaccelerate innovation in defense by working
smarter, faster, and with the best minds acrossthe industry, government, and academia.
It's a must read for anyone who wants tounderstand where defense innovation is going
(02:05):
and where it needs to go.
When I picked this up, I thought, oh, it's abook by my friend.
I don't know how enraptured I will be, but Icouldn't put it down, it was fantastic.
I actually want to read it again, and it taughtme a lot more than just about that intersection
of defense and technology and how the Valleyand the Defense Department didn't have that
(02:29):
perfect bond anymore.
It was such a great book and I really, reallyenjoyed it.
Raj is, it's not done yet.
He's also taught at Stanford.
He's launched and sold a startup, served onboards that span healthcare, education,
national security, the list goes on.
He's also been quietly empowering the nextgeneration through deliverance of 200
(02:50):
scholarships per year to women in rural India.
The dude does it all.
Our conversation starts off with how Raj gotinterested in aviation, how that changed and
molded his career as he launched into all theseother different amazing categories.
Anyways, I'm sure you want to hear more fromme, but let's hear from Raj.
Altitude.
Altitude.
(03:10):
Pull up.
Pull up.
Pressing.
Pressing.
Warning.
Warning.
Bingo.
Bingo.
Lock.
Lock.
Chaff.
Flare.
Chaff.
Flare.
Out.
Chaff.
Flare.
Low.
Jammer.
Jammer.
(03:31):
Raj, what's going on, man?
It's been a while since we've been able tochat, and this took literally, like, four years
to get this thing organized.
Absolutely.
Good to see you, Adam, man.
Yeah.
You too, bud.
In the intro, you heard all about how Raj isthis great, amazing, human being pilot and,
entrepreneur.
Yada yada.
The the list goes on and on.
But what Raj is to me is a very good friend.
(03:51):
We go back twenty about twenty two years,twenty one years now, twenty two, all the way
back to Vance Air Force Base where we learnedhow to fly the mighty T37.
But I had a much different story when I gotinterested in aviation compared to Raj.
What drove what drove you to that?
Because I I know your background, and we'll getall to that stuff.
But, like, what drove you into aviation,especially military aviation?
(04:13):
I think, like, like a lot of, little kids thatend up in the air force, I never grew up.
I loved airplanes since I could imagine and,you know, and and never shook that.
But I think more importantly, you know, youdon't join the Air Force just to to fly.
Join to serve.
And, you know, I, am the kid of immigrants.
(04:34):
My parents, came here from India in the earlyseventies, and this country had been, you know,
just fantastic to our family.
Me and my sisters got to, you know, go toamazing places for, undergrad, and most of my
family now has come here, extended family.
So I wanted to I wanted to serve, and the AirForce said I could serve and fly jets.
(04:55):
So I said, Sign me up.
It's funny because you're you are what weaffectionately call guard baby.
Right?
Like, you're yeah.
You started out the smart way.
I remember when I met these guys in pilottraining.
They're like, oh, you're active duty.
I believe, you and a couple others said, ah,Adam.
Guard guy and an active duty guy's body.
And they're right.
So and I won't let I wanna have to share youralma mater, but I will share that it's
(05:18):
somewhere along the Eastern Seaboard and it'sthe it's got what they would call ivy growing
all over the place.
In that world, how does one go from that worldto like, I'm gonna be a guard baby?
Because you don't see that very often.
And I think that's intriguing to a lot ofpeople, especially me.
Well, I'm glad you finally found the light andcame over to the guard.
(05:40):
Took you a few years and some detours.
Everyone wizens up.
Yeah.
You know, hey, dude.
Give me a break.
I was always a slow learner.
You know, I decided, I think, too late when Iwas in undergrad that I I wanted to go down the
flying path, and so I I wasn't able to miss outon the ROTC path.
And, you know, I had I grew up in Warner Robinsin Georgia, and I had a lot of most of my
(06:00):
friends in high school, their parents served inthe Air Force.
And so one of my good friends, his father was aan Eagle pilot and, was talking to him, and
he's the first one that told me about theguard.
And so I found the only and closest, fighterunit to in Jersey, and I went down and visited
them and got to know some of them and thoughtit was a really interesting path that would
(06:23):
allow me to to serve, but then also, you know,explore some of the other things I wanted to
do.
But as you know, it's it's a very uncertainpath, and this military service is brand new to
me and my family.
Like, no one in my family had ever served inthat military either here in The US or India.
I actually ended up enlisting in the JerseyGuard, I think, my sophomore year of college,
(06:46):
and was, I picked the only specialty that wouldhave allowed me to go through training over the
summer.
So I was scheduled to be an admin person in thesquadron.
And You'd fit right in in that world for youshould have done that for a career.
I think that would've that as soon as you
I was ready to do it.
Was like, no matter how this flying thing goes,I'd love to serve.
And yeah.
So so I was there, and then I had my bagspacked to go to basic, and they had a a pilot
(07:11):
board.
And they're like, well, you should apply.
You know, you usually don't get in your firsttime, but I was like, okay.
It'll be good practice for, you know, after Igraduate.
I just got really lucky that I ended up gettingselected.
And then the squadron was like, well, we haveto send you to a training school, AMS, you
know, at the time.
So why don't you not go to a basic and, justwait?
So I was, you know, I was enlisted in nameonly.
(07:33):
I was like, was it for two and a half years,but never actually went to any any training.
Wasn't any help help.
But, you know, it goes back to, I think, forthem, the fact that I think he was willing to
to sign up and actually take the oath, I think,meant a lot that, hey.
This guy's actually serious about the serviceside of it.
I I would say so I'd I have a conversation witha lot of pilots, you know, who wanna fly
airplanes.
They say, hey.
(07:53):
If you have a service bone in your body, it isquite gratifying for more than just the reason
of you can fly cool jets, go cool places.
There's a lot there that is not it's anextrinsic motivator, I think, for a lot of us
while we do it.
A lot of really successful, great people whoyou would not otherwise believe served their
(08:15):
country one way or another, but a lot ofmilitary service.
As your military service kind of kicked off, wewent through training together, you go, you
know, the B course and all that good stuff.
You come back and I remember this was kind ofmy introduction to you knowing way more about
stuff than I thought we knew.
Because I mean, pilot training, there wasn't alot of talk about anything other than what
(08:35):
we're doing at pilot training professionallyand then what was happening on Friday and
Saturday nights.
Like, those were the that was in crux of prettymuch everything that was going on there,
especially for a simpleton like myself.
We won't get into what those those nights,entailed on this podcast, will we?
No.
We won't.
That's a you that is I will gladly buy people aa drink or they could buy me one if they wanna
(08:58):
have that conversation.
More than happy to get into it in person.
That is what for that is what the hanger fliesand the TPN chapters are for.
So if you're interested, you gotta show up tothose things.
Anyways, what I noticed was you you wrote thisarticle, and I don't remember I can't remember
where I saw it.
I I don't know if you sent it to me.
I think you might have sent me a link orsomething.
But you had deployed, and you were taking somepretty cool pictures when you were flying and
(09:24):
you were also writing about some of thetechnological side of what you were doing,
stuff that I didn't understand, not onlybecause I wasn't a fighter guy, but also
because I was kind of adult.
And when I put those two things together, waslike, woah.
You know, this is kinda cool.
Where did your where did that interest spark?
Because this will come up much, you know, laterin your career where you really got really got
(09:46):
involved in the innovation technology space.
Where did that kind of confluence start tooccur?
Was that like right away when you showed up inthe military or was that before or did it start
happening when you're flying the, the wonderfulf 16?
Well, I think I've always had an interest in inin technology.
I mean, I started off as an engineer and thenrealized I wasn't smart enough to be an
(10:07):
engineer and became a public policy guy.
But, I think, all of us have grown up in thisworld where the technology that we had to go to
war with on in some sense was amazing.
Right?
Amazing performances in an airplane andweapons.
Yet, it was walking into the stone age at thesame time from your software standpoint.
(10:29):
Right?
Like, your phone was more powerful than all theavionics in your in in the jets.
And so I think, for all of us, we sort of sawthat.
And for me, the first visceral time was thiswould be o six, my first tour in Middle East,
in Iraq.
And, you know, I'm just a young wingman andtrying to make my way through and do things
(10:51):
right, not get in trouble.
And most of our missions or many of them weresupporting troops on the border between Iran
and Iraq, and we're doing a cast wheel overthem.
And at, you know, 400 knots, you know, you'retraveling pretty fast, but there's no moving
map.
And, you know, you know, you don't wanna gointo Iran too far.
You know, maybe they'll shoot at you or createsome international, but, you know, god forbid,
(11:13):
the general finds out and then, like, sends youhome from the warp.
Like, that could be it could be nothing worsethan that.
And, you know, I'd that same year, of course,we could rent a a Cessna back home.
And the predecessor to the iPad, an iPac, youcould rent you could put a $100 piece of
software on there and have a moving map.
And so a couple of us downloaded the maps forThe Middle East, put it on there, and the the
(11:38):
good news about a single seat airplane is thatif you decide to bring your iPad with you, that
no one else Print data.
So someone was fluent that, and I could lookdown at this thing and know where I was.
And so that was, like, kind of the first realvisceral example to me of of how how these two
different systems of technology development andprocurement had diverged and were and the
(12:00):
divergence was accelerating.
Yeah.
It spot on.
I remembered, on the other side, the taker sideis, oh, we got this great new thing.
It was called Block 40, and it's got, CPDLC andall this cool whiz bang stuff.
And I was like, I don't know what any of thisis.
I remember the most exciting thing I was isthey took the radio head out of the side down
(12:21):
by my right leg for the HF, and they put itinto the actual box where I could type in a
frequency.
And I thought this was the coolest thing I'dever seen in my life.
Little did I know that this is not that big ofa leap in technology and that we had much worse
problems in the jet that I didn't understand.
And that being part of it, like, although we'renot moving around that fast, we are moving a
(12:41):
lot of airspace, a lot of different airspacesegments when we're flying over and above
combat zones.
And when you don't necessarily you know whereyou are on the map that you drew with some lat
longs, which is better than the stuff you guyshad, but you can't see it on a map.
You can't see it on a digital read orForeFlight readout nowadays where you go,
(13:02):
that's the border of Iran.
Don't come close to it or that's there.
It was not we we weren't there yet.
And I think I I don't think I owned an iPaduntil about 02/2008.
So I was behind the times a little bit before Igot into that world.
When you saw that when you had this sense of,okay, we're we're behind in our software, our
(13:26):
some of our hardware stuff.
I mean, obviously not the stuff that goes boom,but the stuff that we can actually use to,
prosecute the mission on the back end, iPads,etcetera.
What was your first step into the idea of,like, you know what?
I think I can I think I might be able to Ithink I might be able to change some of
know, at the time, I didn't think I didn'tthink there was much I I could do?
(13:47):
Right?
Because, you always believed, hey.
There's some smart group or team somewhere inthe Air Force that's, like, working on this.
We're in the in the military.
But, you know, it did it's something that thatstuck with me.
And so after my, whatever, six years of fulltime there, I, you know, I became a traditional
(14:07):
guardsman part timer there at the base, keptflying, went through business school, became a
consultant, but, you know, realized I reallyliked early stage entrepreneurship, building
teams, and solving problems.
And so I met a couple of smart guys out of theNational Security Agency, some of our best
attackers, hackers, and said, you know, howwould you stop yourself?
Because as much as I love a hoarder makes tocome over the horizon and they call me to go
(14:30):
shoot them down, like, that's not the majorthreat, facing us.
Right?
It's guys on keyboard, hacking things.
And so we ended up doing an early stagestartup.
Right?
Started in the basement of a townhome inMaryland and, you know, started building
technology, and I was the only guy thatcouldn't write code, so I I did everything but
write code from flooring lunch to raising moneyto trying to sell this stuff.
(14:53):
So, ultimately, we we grew the business.
And, you know, we knew what we were buildingwould have been valuable to the government
because that's where our team was from.
But I think after my, like, eighth meeting withsome random general, we just said enough.
Like, it's wasting time as a start up to try tosell to the DOD.
Our investors even told us, hey.
(15:14):
Don't sell don't work these guys.
They're just gonna slow you down.
It's actually gonna lower your valuation.
And so, ultimately, the company ended up beingacquired by a big public company, and we had
zero sense of government revenue when when wesold it.
So here I've now seen both sides, right, as theuser not getting access to modern technology,
but then as someone helping to build tech,seeing just how hard it was to work with the
(15:38):
government.
And, you know, after selling it, I had to restinvest there for two years.
I was presented with the opportunity to try togo and fix that.
And that was that was helping stand up thisthing called the defense innovation unit.
And, you know, that's the real time when Isaid, okay.
I could actually go and try to solve thosethings that, you know, it was a decade before
(16:00):
with that deployment.
Yeah.
I could help build a team to go and solve theproblems that frustrated me when I was a when I
was a young captain.
Yeah.
I remember this phase because we would talk,like, occasionally.
Maybe, you know, six months, year, somethinglike that.
Just catch up, blah blah blah.
And you're telling me, not in detail, justlike, oh, yeah.
I got this going on, that going on.
(16:21):
I'm like, dude, yeah.
That's cool.
I have no early earthly idea.
It's funny now because I'm doing some work witha buddy of mine on a startup and man, you're so
right.
I'm trying to work with the DOD on certainthings.
There's a lot of people who want it, but to getto the end product and getting it in the hands
of the warfighter is very, very difficultunless you have something that's really great
(16:43):
and sponsored by the right person.
It's very challenging.
So I can't imagine what it was like before DIUcame along.
Mentioned this in the intro, the book that youended up authoring is where I got a lot of my
information that I pieced together my friend'sjourney.
So you start DIU, which was DIUX back then,right?
(17:06):
Defense Initiative Unit Experimental.
With this idea of we're gonna bridge this gapbetween what Silicon Valley and the tech
wizards are doing on the outside and what thedefense needs are on the inside that we know,
especially you, because from a tactical andstrategic point of view, we're not just
strategy.
(17:27):
Back then, and you mentioned this in the book,that the Valley was not real keen on military
support at the time.
And, that to me seems like even a bigger hurdlethan trying to plow in through the DOD to get
somebody to buy what you're trying to sell.
How did you guys even start that process?
(17:49):
Yeah.
Yeah.
So you gotta think back.
So the founder of DIUX, was secretary AshCarter.
Right?
This was his brainchild.
In fact, in 02/2001, he wrote a paper when hewas still at Harvard about how commercial
technology would be decisive on the battlefieldof the future.
Robots, AI, drones, all the stuff that'sobvious now post Ukraine.
(18:09):
But, you know, he thought about it in 02/2001,and then fifteen years later, he's now
secretary of defense, and he goes andimplements his, his vision.
And I think what made him successful andultimately DIU successful is, you know, there's
a lot of people that have visions and havegreat ideas.
There's very few that can actually go and thenexecute on that.
And I think Carter had that unique ability todo both because he'd already been in the
(18:34):
building.
Right?
He was the deputy secretary.
He was the head of acquisitions.
So, like, he knew how the place worked.
I remember sitting in meetings with him wherehe'd have some idea.
Like, we should go do this.
And then the staff would come in like, hey,sir.
You know, we can't do it for this reason, thatreason.
And he'd be like, bullshit.
I know you can.
Go find somebody that go get it done or I'llfind somebody that will by next week.
(18:54):
And he knew the difference between what waslike a policy and a regulation that could be
run over and what was law and what was actuallypossible.
And so that, I think, made him really unique.
And so he started it.
He he was the first sitting secretary to comeout to Silicon Valley in, like, thirty years to
talk about this, idea of a of a partnership.
(19:16):
And you're right.
At that time, it was it was a challenging timefor the Pentagon to work, and interact with
folks in the Valley.
You gotta think back.
If you look historically, the Valley wasstarted because of the military and to solve
national security problems.
Right?
It was started many of the the early effortswere to solve radar issues in World War two.
(19:36):
Right?
How do we catch German, bombers trying to dropbombs on in London, and how do we the
electronic warfare side.
That's the start of it.
The first satellites were here, were builtthere, ICBMs, like integrated circuits.
So it was there.
But then, you know, the world diverged in thatso much more of the r and d was commercially
(19:58):
oriented going after this huge commercialconsumer market.
Right?
IPhones, cloud, etcetera.
And so those things diverge.
And then, of course, then there's the the, youknow, some of the philosophy stuff.
So when he came out there, this was right afterthe Snowden revelations.
Right?
Ed Edward Snowden talked about what the NSA haddone, and, some folks out there thought the,
(20:19):
you know, NSA was just as bad as the Chinese interms of of of spying.
And you started this kind of tough spot.
But the real problem, right, and the real issuewas, I think, less philosophical, right, like
anti war, anti government, but just business isa business.
Like, it was just too hard to work with thegovernment if you're a start up.
Right?
A start up has to raise money every eighteenmonths to stay alive, and so you need to show
(20:43):
progress, like selling to customers.
And if it takes four years for your customer tobuy something, which is the average contracting
times for the government, then it doesn't makeany sense until you're like a really big a big
company.
And so I think changing that and finding a wayto get companies on contract quickly to talk
about our problem sets was what DIUX's missionwas.
(21:05):
And I'll tell you all my battles weren't out inthe valley.
They were in DC.
Yeah.
I ended up having to fly there basically everyweek, taking a red eye and a middle seat coach
on United first to go and, like, battle in thePentagon or battle on on Capitol Hill on for
our budget and, and begin to change.
And this is where, again, I give so much creditto secretary Carter and then secretary Mattis.
(21:27):
Those are the guys I worked for.
Is that, like, he he just gave both of themgave me so much authority and leeway and trust.
I mean, we even had this thing where we couldask for an exception to any regulation or
policy that we thought were getting in our way.
And then they had to come up with anadjudication in that group within, like, ten
(21:48):
days, and all negative adjudications had to besent directly to the secretary.
So I could just, like, walk around thePentagon.
Was like, you don't wanna do this.
It's gonna slow you down because it'saccreditation problem, whatever ATF.
You wanna tell the secretary or do you want meto tell them that it's get slowed?
They're like, you know what?
We can I think we can get it done?
Oh, okay.
Yeah.
Amazing how that works.
Wait.
That's that's the thing.
Like, bureaucracies are such a pain in thebutt, but the good news about a bureaucracy is,
(22:11):
like, one person at the top.
And if that person says jump, then everyonedoes.
And this is where I think leadership reallydoes matter, and places like the Pentagon can
be reformed.
And, of course, you know, now ten years later,it's just a it's just such a different place to
do business with.
And speaking of that, so, like, you've seen theevolution of DIU and how it integrates with the
Pentagon at large.
(22:32):
And I've seen it from a different perspectiveworking with my buddy on this startup, seeing
how, you know, going through, like, the thesmall business, cyber phases, all that kind of
stuff, awards.
Still seeing that, yes, even with all thischange, there's still a lot of improvement that
can be made on some other levels.
But as far as DIU and DOD go working together,what have you seen?
(22:55):
Because my understanding of DIU is it's, yeah,there's a lot of software, but it's also
there's a lot of hardware tech stuff that like,and stuff that's employable essentially
rapidly.
This isn't something that's like, oh, yeah, insix years you're going to be able to do this.
Every aircraft ever purchased for the UnitedStates government has been like, oh yeah, yeah,
(23:17):
like in six years this thing's going beamazing.
And then it's that.
So that evolution from where you started towhere we're at today and going forward, how do
you how did you see that unfold?
Yeah.
No.
It's it's remarkable what the organization'sdone, and I give it a lot of credit to my kind
of successor.
So Mike Brown ran it for four years after me,and then Doug Beck has run it for the last two
(23:38):
years.
Right?
We've all known each other for a long time, andthey've done amazing work.
So there's a lot of there's a couple ofdifferent ways you can try to measure success
and impact.
The government, of course, money talk.
So, you know, budgets matter.
I think my budget in that year one was, like, Idon't know, $1,820,000,000 bucks.
This last bill that just passed, DAU got a$2,000,000,000 plus up.
(24:00):
Wow.
So, you know, now that's real dollars.
Still, I don't you know, in a $800,000,000,000budget, it still feels to me like it's kind of
a rounding error, but you can get a lot done.
And then from a a mission impact standpoint,right, publicly, they've been working on this
effort called Replicator, and now they havesomething called Replicator two, which is
really how do you get, autonomy to supportcombatant commands in the warfighter,
(24:25):
particularly out in the Pacific, at a speedthat matters, right, to to deter any sort of,
you know, invasion or military action in theTaiwan Straits.
And so they're building all kinds of differentdrones on the sea and in the sky and moving
really, really fast.
And so I think there's immense mission impact.
Right?
It's not, you know the the level of that impactto, like, solving my iPad problem is, like, you
(24:49):
know, just two totally different differentlevels.
So it's, you know, it's great to see.
And I think more importantly, it's those tools,those techniques, that approach should infuse
across the department.
Right?
You just don't need one organization doinginnovation.
Right?
This is how the whole play should operate.
And I think you're beginning to you'rebeginning to see that, at the services level
(25:10):
and at other co comms.
So when you say kind of services and the COCOMsand stuff like that and DIU being a DOD
supportive investment, when you're talkingabout stuff like that, how not to get into
finer a point, but the Air Force vice the Navyand Army have always had that the budget for
(25:30):
tech on the Air Force side or R and D hasalways always, but generally higher just
because of the nature of the beast.
Is the split is a split even up to people?
Is there lots of money going to the army andthe navy?
Lots of cool new things and stuff that canreally help the warfighter on the ground.
Because as I've always said to my friends,you've been like, oh, you know, you're an air
(25:51):
force guy and your friends, fighter pilots,blah, blah, blah, blah.
I go, yeah, yeah, yeah.
We're all support.
We're all support.
There's only one person that matters, that'sthe 18 year old on the ground with a rifle.
Who's that?
Yeah.
Whose boots there.
So I've always wanted to see more money, moresupport go to those kids on the ground who are
doing that the hard work.
What How's that split working?
(26:12):
Is it is it is it looking like it's we're doingthe supportive role for people that are
actually in the suck?
Yeah.
No.
I think so.
Look.
I think there's, as much as I rail on all thebureaucrats in the Pentagon, they're not ill
intentioned.
Right?
They're they're there because they believe inwhat they're doing, and they believe in,
service and and strengthening our nationalsecurity.
(26:32):
So they're trying to do the do the right thing.
You know, I think what's interesting when wethink about budgets and and money and about
innovation, you know, is that commercialinnovation, you can leverage a lot of r and d
that other people that the private sector hasdone.
So if you wanna build a a stealthy fighter jetor an aircraft carrier, like, there's no
commercial market.
Right?
Yeah.
And so there's only one buyer.
(26:54):
And so that means the government's gonna payfor all the r and d, and that's why these
things take a really long time.
And, you know, I'd say the system does an okayjob at buying an aircraft carrier.
Like, you're gonna keep the thing for fiftyyears.
You wanna make sure it's done right and haveall these requirements.
But it's it's totally ill suited for commercialtechnology that's moving so so fast.
And I think what I what's really important isthat the cost, the price points of some of
(27:17):
these things, like low cost satellites, ofcourse, software, small drones.
It's just it's just orders of magnitude.
So when I think about budgets and supportingpeople on the ground, I think about what's the
mix?
Meaning, how much is going to go to legacy typeof equipment, and how much of it's going to go
to rapid fast moving systems.
(27:39):
You know, we've all played with AI now.
Right?
We all use ChatGPT.
You can see the power of that.
Know?
What you know, how long is it gonna take for usto get that to every single soldier to
understand what's around them to be able toquery all this data, these sensors?
That's just one example.
So I think really what's important to me iswhat's the mix?
What percentage of our DOD budget is going togo towards new modern technology versus a
(28:04):
legacy stuff.
And the DOD has this, you know, unique,strategic challenge that it has to be able to
fight today.
Right?
Like, we have to go to war tomorrow.
You have to be ready to do that, and you haveto you have the equipment that you need.
But you also need a plan for ten years fromnow.
And how do you how are you going to takeadvantage of these changes to continue to have
deterrents?
(28:25):
And, you know, it has to have this right mix.
I think the mix is probably skewed a little bitstill too much on the legacy side.
You know, if you talk to different,congressional teams and, the navy, you know,
everybody loves drones and and new technologyuntil you say, let's have one less aircraft
carrier.
I'm like, wow.
And so it's a it's a complicated, a complicatedcalculus.
(28:45):
But I I get so much positive, I think, changein momentum.
And even this last build up has passed that youcan just see the dollars that are being placed
towards, again, modern technologies like AIdrones.
Yeah.
You know, I I tend to agree with you.
We pick some of this modern modern stuff up.
We actually we plan and prepare correctly.
(29:08):
The costs will come down.
I mean, it's very okay.
Let let's be realistic.
When you when somebody gets a a a $50 allowancefor the week and then you go, okay.
You know what?
We're gonna reduce your allowance to 35 nextweek.
There is gonna be some bitching complaining.
And so I don't necessarily see that, but thefuture increase when you can scale it, like you
(29:28):
said, and do it and scale correctly, we couldsee a definite shift in where that money could
be allocated if it's done correctly.
And I like you said, I mean, read the book,guys.
It is it's fantastic.
It'll give you a insight that I didn't havebeforehand, and I'm friends with Raj.
So if I otherwise, you're just making thisstuff up in your head or you're, you know,
you're reading it on, whatever website youchoose to.
(29:50):
But this gives you some real insight on whatwas going on in that historical lead up and now
what's happening now.
Speaking of now, what are you up to now?
I mean, I know what you're up to, but you wrotea book, you still fly, you're in the
entrepreneurial space, you got the family lifegoing on.
How did you you were out of the cockpit for awhile, right?
Like you stepped away and obviously you missedit.
(30:12):
So you came back.
That was I mean, that's a no brainer.
But tell me about like we we gotta talk aboutwhat job did you take and how did you get back
into it?
Because it was to me, it was one of my favoritestory.
It's one of my favorite stories of all myfriends getting back into flying.
Yeah.
Look.
I think when I, so I'd come back to my my thirddeployment, felt the taxpayers got their
money's worth out of me, and I was startingthat first company.
(30:35):
And Yeah.
You know, early stage entrepreneurship, it it'sjust it's just so hard, and it's so all
consuming because, you know, you just don'tknow what you're doing.
Right?
It's a I I would say it's like impossible to betaught how to be a CEO.
You can learn it, but you can only do it youcan only learn it by doing it.
And so there was just I couldn't I couldn'tbalance it also.
I so I I stopped flying and hung it up andthought I was I was done.
(30:57):
You know?
But then I think it was like five years later,I'm in I'm at DIU X, and I really missed,
serving.
I missed being I mean, I had stayed in theguard, and the guard is very flexible in
enabling that.
I had wonderful commanders that, you know, putup with me and allowed me to to stay in in
uniform.
And and there was a shortage of pilots andparticularly some test support kinda work.
(31:19):
And so they they offered me the opportunity togo back, and I said, let's do it.
Hell yeah.
Yeah.
Yeah.
And and and so now, you know, I'm I'm still in,and it's such a treat, like, to get to to put
the the uniform on.
Right?
Because I know there's, you know, limitednumber of days that I'll still get to do that.
So it's, like, such an honor to to get to goand do that today.
(31:40):
And so I always encourage folks that are, youknow, leaving.
I know I know this podcast is a lot of piratesand a lot of service folks is that finding a
way to to stay in whether or not you can fly ornot, but find a way to serve.
Continue is like because it's been such a bigpart of your life.
If you could make it work, I always try torecommend people to to do that.
You know, to your question of what do I do now,you know, entrepreneurship, I also think, is
(32:02):
kind of a young man sport as is, I think,flying jets.
But now I I have the, you know, privilege.
What's that?
It's young at heart.
You don't
have Young at heart.
Young at heart.
Young at heart.
Be young.
Try not to pull as many g's these days.
G's on
the old
back.
Yeah.
You know, I get the job I I have an amazing jobnow where I get to help support and work with
(32:22):
the next generation of of innovators.
So, I help run a venture fund called ShieldCapital.
We invest in companies at the intersection ofnatural security and commercial.
So four kind of core technology areas, AI,cyber, space, you know, and robotics slash
autonomy.
And, you know, we are early stage, so twopeople and a dog to, you know, maybe a team of
(32:44):
20 people.
Right?
So it's very, very early stage.
And so we invest in them, and then we helpmentor and guide and and support them and help
them learn from the mistakes that that we'dmade when we were we were entrepreneurs.
And so it's just exciting to see how manypeople now want to go and build companies
supporting national security.
Like, I've just I've never seen so many amazingengineers.
(33:08):
Right?
I think they're just bored building photosharing op you know, apps.
Like, it's just only so much fun.
And I think this generation really wants tofind meaning and do something that matters.
And post Ukraine, post Israel, you know, Ithink folks realize, hey.
There's authoritarians out there that don'tbelieve in the sort of, you know, Western
(33:29):
democratic values that we do, and having havinga force that can deter that is important.
And so you see people wanting to serve.
So it's really it's really exciting.
And I think to your point you were makingearlier, there's lots of different ways to
serve.
It doesn't only have to be in in uniform.
Yeah.
The these folks are doing great stuff.
So it's great.
I get to spend a lot of time with these highenergy entrepreneurs, and it also helps with my
(33:50):
ADD because I could do multiple things at thesame time.
I know.
I I had a conversation last night with a couplepilots that joined me on our Ask Me Anything
biweekly series in one of the where there wastalk about side hustles, whatever.
You you could become an airline pilot.
Like, hey, you got this time off.
What are you gonna do with your time?
And I said, you know, I used to say, yeah, youcan go get a job or go get into real estate or
(34:14):
create your own business, blah, blah, blah, AndI said, you know, you're gonna make plenty of
money being an airline pilot, whatever.
Don't let that drive you.
Let your talent for something that you enjoydoing, let that drive you.
It becomes your passion.
One of the guys was talking about running, bigmarathon runner type.
I said, if you don't want to start a job orstart a whole new world of business for
(34:36):
yourself, you can be kind of your ownentrepreneur on yourself and go go I mean, go
do something basic to drive and serve.
Yes.
You retired from the military.
That service bone is is that service itch isprobably not gonna get scratched unless you go
do something else.
If you don't do that something else, you'regonna be kind of wondering what it is you're
(34:56):
showing up to work for.
And then once you once you fill that up withkind of fill that cup, you'll kind of feel that
feeling of, that's what the military was givingme all these years and I didn't know that.
I've been very lucky to have TPN for so longthat I've been able to get that sometimes.
Sometimes it feels like, why the hell am Idoing this still?
But I I I love that the fact of that we'retalking about that service aspect and that's
(35:19):
kind of how it all started for you and how itcontinues to drive you to go and do this and
work with these people to help serve what we'redoing as a whole as a collective.
So, Raj, to kind of wrap up, where where canpeople find you, reach out to you, chat with
you, see what you're up to these days, and thenalso any parting shots you got for me and the
and the network out there?
(35:39):
Yeah.
Well, I'm I'm I'm easily discoverable, so youcan find me on LinkedIn or my email is just
rodjie shieldcap dot com, so I'm I'm I can befound.
And we've got great blogs and other things onour our website so you can learn about the
companies that we're investing in and and toyour point, lots of opportunities.
I mean, I guess, like, the the final, partingshot, I would say, is, you know so first, you
(36:03):
know, thanks for this opportunity, and thanksfor putting together this network.
I think folks that have spent time inparticularly military aviation, it's a it's a
special community.
It's a special tribe, and it's one where Ithink, that shared experience really makes
people wanna help each other, which is which isawesome.
But then I'd I'd go back to what you said theretoo is that coming from that tribe, you've done
(36:27):
some pretty amazing things, and there's, like,no limit to what you can do.
Right?
Obviously, you can you can fly airplanes, andyou should need to do that.
And there's lots of opportunity there.
But there's all kinds of things on the side andand transition that your skill sets and your
leadership can drive.
And as we see this just redoubling ofindustrialization here in The US and technology
(36:49):
building for national security.
I think there's those skill sets are in need,and there's lots of opportunities.
Dude, it's fun chatting.
It's been long too long.
We we gotta gotta make it more often than just,you know, once in a while.
Hopefully, we'll be coming out going out to seeRaj in in on the West Coast soon.
But I wanna thank you again for all that you'vedone for me and for what you've done for the
(37:09):
network.
For those of you who don't know, Raj is likeprobably a member like number 15 or 20.
Oh, that's that's how far we go back.
And and I I appreciate time.
I know how busy of a guy you are.
And for those of you out there who need to geta hold of me or Matt, hit us up at
heyguys@thepilotnetwork.com.
You can go to the pilotnetwork.com to findanything else about this, the podcast, whatever
(37:29):
else you need to know when we're doing ourmeetups, when we're having chats and all that
good stuff, and then sign up
for the
newsletter.
Name change coming soon.
Again, thank you all for being a part of thenetwork.
Keep that shiny side up.
Greasy side down.
Fly safe, everybody.
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