Kevin Chapman’s career has been anything but predictable. From a college internship that led to Capitol Hill, to serving at the Department of Transportation during 9/11 and helping with the unprecedented work that followed, Kevin’s story is filled with unexpected opportunities, historic moments, and a willingness to keep stepping into what comes next. In this episode, Kevin shares stories from his years in Washington, working across presidential administrations, his eventual move into education, and the lessons he’s gathered along the way about leadership, service, growth, and embracing the next adventure.
Kevin Chapman’s career has been anything but predictable. From a college internship that led to Capitol Hill, to serving at the Department of Transportation during 9/11 and helping with the unprecedented work that followed, Kevin’s story is filled with unexpected opportunities, historic moments, and a willingness to keep stepping into what comes next. In this episode, Kevin shares stories from his years in Washington, working across presidential administrations, his eventual move into education, and the lessons he’s gathered along the way about leadership, service, growth, and embracing the next adventure.
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Always trust your body. Hi, Dad. I think we're recording. Is it recording? I think we're recording. Where's
that voice coming? It's coming for me. Oh, hi. What's up? Same old stuff. Yeah. What'd you have for lunch
today? I had a half of tuna wrap and some vegetables with dip, and I'm feeling good. I'm like a nine and a
half. Oh, nice. Nice. What? 95 Why? I got a little pinch in my neck. Wait, nine and a half is the same thing
as 95 I said 975 No, you said nine and a half the first time said 95 the first time.
I'm back to 96 Do you know who I am? You have an identification? I was watching this video the other
day, they were saying that it's a test you can do to see if you have dementia. It was something like, I don't
know, was this doctor doing it? Uhoh uhoh I did it. I don't know, anyway, it was really funny, but it was
not funny. But it's like, I find myself now, and I don't know if it's because I've got too many tabs open, but
I find myself, you know, I'm like, I'll be like, what am I doing here like or like, I'm all right, like, I think
it's because there's just so much, too much going on. That's a possibility. Yeah. So, but I'm the one that tells
people you got to like shed that funk. And so I do. So I like, so. Are you wondering why you're here now?
Yeah, I am. Why are we here? Push over. I'll take over. Go ahead. Hey, folks. Today we're going to speak
with Kevin Chapman. Kevin Chapman is a man very distinguished in his field. He's actually, he's
outstanding in his field, but he may make an appearance by coming in from his field and talking to us this
morning.
Can I come back in the picture now? I can come back in the picture. Now you know where you are. You
should do your own podcast. Why don't you just do your own podcast without me? No. You're funny.
You're funny. Clown funny? Funny. Ha ha. Yeah. All right, folks. Welcome back to another episode of
what's Your Story today. We are super pumped not just to talk to you about our just life and just father
daughter stuff here, but we are entering in our friend and our guest today, Kevin Chapman. You will learn
this. I know, but like you did, but like you didn't hear us though.
He can't hear us now, but he will be able to hear us when he comes in. He's here. Yes, he will be able to
hear when he comes in, and you'll you'll see that. So that'll be good. So let's see, Kevin, are you there? He
was there. There he is. Hi, Kevin. That invenses your life. How are you? Pretty good. Get your. How are
you? Good to see you. Oh my gosh. This is, I've been watching these and listening to these, and here we
go. This is unbelievable. I know. We get one now. Well, thanks for being a longtime listener, longtime fan.
We're so grateful for that. Just me one second. I just want to make sure something's working. Give me one
second. All right. I'm just making sure we're recording. It's was just making sure we were recording. It said
recording, but then I was like, I wasn't sure if it was recording. So I'm hoping it's recording. We'll just do
this all over again. I want to repeat, but I forgot what I said. You always forget what you say. Let's put the
theme feet. King for a day. Who may it be? 00:01
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I'm just going to apologize in advance. Kevin, I know you. You've never met my father, though, I don't
think. Or maybe you met him at my book signing. I'm not really sure. Did you? Well, either way, it's an
honor. So, Kevin, feeling is mutual. Thank you. You will learn very quickly the apple doesn't fall far from
the tree, minus the fact that he may say things that I would not say ever. Somebody has to. Well, we are.
Yeah. We're so grateful to have you as our guest today. And if you've been watching, you know that we ask
the same question in the beginning of all of our episodes to see where you are with your mindset today.
So, Dad, do you want to ask it? Do you want to do the honors? He's been practicing. We kind of rate your
emotional and fun scale daily on a scale of one to 10, where fractions and decimals do count.
So, please. So, you've been preparing for this for months now. So, please. What is your number this
morning and see where we can go from there. Yeah, I'd say probably 8 and 12 How's that, 8 and 12 that's
good, right? We've done our job. Yeah, I like that. We're done. See you later. No, I'm just kidding. So the
followup question is, what would it take to go from 8 and 12 to 875 what would be your 025 today? How
much is that? Well, you can make it a little cooler. Let's see. I don't know. We could not have so many
naughty teachers and kids in our school district. No, I'm kidding. You're not wrong. End of the pool. I feel
like it's just human nature today, right? People are people. And I think that's really interesting. You've
worked in education for a while, but you also have an extensive background elsewhere. But I think that
that's what happens is that people sometimes think that we put people on pedestals, but we forget that
they're actually just humans. And so, there are bad seeds in every area and every industry. You know, like
what is it?
What do they call the doctor that graduates at the bottom of their class? The doctor. Yeah. Yeah. One of the
things I was taught early early on was humans make mistakes, like you said, but never make the same
mistake twice, because then you're not learning, you're not showing growth, you're not showing that kind
of emotional intelligence that should come from that. And I think I've tried to follow that. I'm sure I
messed that up along the way, but I think that's a good lesson, is you're gonna make mistakes, but try not
to make the same mistake twice. Well, and nobody's perfect, right? Like that's the thing. We have to
remember is that no one, like, there's no like book on life. There's a game, but no book, you know? And it's
like, you just don't know. There's no book on life. There's no book, you know, you're everyone's still trying
to figure themselves out whether you are, you know, three, 10, 15, 70, almost.
But that's what's the cool thing about life. So, you, I feel though, have led a life like a cat. I feel like you
have had nine lives. Is that an accurate statement? That's funny. I never heard that. That's good. I like that.
Sure. Sure. It's hard for me to, like, right now I get, I'm itching. Like, I've been at seven years at the school
district and I'm itching. I'm kind of ready for my next adventure, I think. I think it gets that time where you
get a little itchy and want to kind of find the next challenge somewhere.
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Yeah. And your background is so diverse when I say that, right? So we'd love to learn that about your story
and kind of get to learn more about you and our audience to know more about you. Because also the work
that you do every day is not for the faint of heart heart in the last seven years. So just full disclaimer, share
with our audience what your role is right now. Yeah, right now I'm the associate superintendent, whatever
that means, of the School District of Manatee County. So just really a just a great job and really great job
and really just a pleasure to work for so many great students and teachers and families here in one of the
best places on earth, Manatee County. Amazing. Well, we don't define you by that role, but thanks for just
doing that. But you didn't start off there. That wasn't your thing. I will say, in the last seven years, you've
had to deal with so many different wild things going on from COVID to news stories to everything. I
mean, thank goodness we're not Sarasota County. But anyway, but let's go back to where this all started for
you and how you even got to where you are now.
So, where did you grow up? I think I kind of know because of the research I've done, but my dad doesn't.
So, enlighten our audience as well. Where'd you grow up? Yeah. Yeah. From like a lot of people in
Florida, I grew up in New Jersey outside New York City. So, North Jersey, Bergen County, New Jersey. I
forgot not know that. Where in Bergen County? Wyckoff, New Jersey. So, by Ridgewood, Ramsey, Maui.
Way up. She was born and suffered in Good Samaritan. Oh, there you go. Sure. Right down the street.
Yeah. We lived in Maui for a little bit, just there at the end of Route 17 there. Yeah. And then I spent my
summers in the Adirondacks, you know, up in Lake Placid. And then I would spend July in the
Adirondacks. The month of August at Long Beach Island down on the Jersey Shore.
So, for those Jerseyites listening, they'll probably know Long Beach Island. So, I love it. So, growing up,
what was your life like growing up there in New Jersey and like close to the city? Did you take advantage
of that? Tell us a little bit like growing up, what your life was like. Yeah, no, thanks. Dad worked for IBM,
so he was very busy. IBM was a big deal up there at that time. It's a little different now, but mom's been
working in dentistry since she was 14. So, My teeth always had to be perfect. And I think I wore braces
my whole life, I feel like.
But life was nice. My parents really gave me a wonderful opportunity to do many things. I was too skinny
to play any sport. So I took up golf and love golf to this day, which has worked well. But just a wonderful
place to live. And yeah, I became a big New York sports fan, right? So my dad would take me to Yankee
games. We've had New York Giants football season tickets ever since I was born. So I'll be there opening
night here coming up soon. And so, you know, that was life in New York City. My mom would take me to
Broadway shows, which was amazing. So yeah, we took advantage of being so close to the city. Kevin,
wait. Are you an only child? I have two older sisters, so I'm the baby boy. So, you know, I get spoiled.
We're here for the dark underbelly of that story. Yeah, we'll get there. Kevin laughs) Yeah, I just got a shirt
the other day in the mail, a championship golf shirt. So yeah, the Knicks put the trophy and all that, but
they had a lot of fun with the trophy and all that.
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But yeah, that was fun to watch. Yeah, the last time they won was when I graduated college in 1999, I
think. So, we graduated at the same time. You know what? Did your dad work up in Poughkeepsie for
IBM? I don't know if he, yeah, he would go up there. He ran the financial division, which was all based
out of Franklin Lakes, New Jersey. They had a huge property there. And that's when they, you know, still
were making computers and typewriters, which they didn't do anymore, buddy. My uncle worked for IBM
for many, many years too well adjusted. I mean, like, but seriously, what a great, like, mixed childhood.
You had the sports side of it, you had the arts and the theater side of it, and just growing up and having
those experiences. And so when you were growing up, did you have a dream of wanting to be a pro golfer
or something that you thought you were going to get into?
Well, that's a great question. You'd think so a little bit, but my dad was very, maybe like most fathers, we
were involved in, you know, he would read the New York Times every day. We would watch Dan Rather
at night at 6 30. So he was very involved with current events. You know, there wasn't Fox News then.
Otherwise, you know, later in life, he was addicted to Fox News. But he just loved talking politics. He
wasn't one to like scream and yell at the television, but he was just, you know, he was in Vietnam. I think
that changed him to be very involved, you know, kind of following government and politics. And that,
Became an interest of mine, right? You kind of emulate what your parents are interested in. And so I went
off to college, you know, kind of more interested in politics. And government and things like that, not
really knowing what I wanted to do, but knowing that that was an interest of mine. So, I was like, you
know, class president and in debate club, and I was that guy, but I was friends with many different friends
groups. I was in the band, for nine years, and so you know, what's your instrument?
All the brass instruments. I said, too bad. Yeah, it's kind of hard to find a band guy that was also class
president, you know, it's just kind of like two different worlds. But um, you had me because I did speech
and debate, and I was class president, but I was not in a band, I was a cheerleader, though, and a song,
right? Say a little more popular, stuff. So where did you decide, when you were deciding to go to school,
you knew exactly where you wanted to go? Or what did that look like for you? I did, but I didn't get in. I
wanted to go to Wake Forest University to play golf. I would go to summer camp there for a week. But I
got waitlisted, which was probably a blessing, because I don't know if a New Jersey boy would have fit in
at such a southern school. But my backup was American. University in Washington DC most kids who
couldn't get into Georgetown would have go to either George Washington or American. And then when
you go with your parents to visit Washington, George Washington is an urban school. It's in downtown DC
and then Americans up where the ambassadors live in this beautiful neighborhood.
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And so it just depends. You know, your parents are like, oh, wow, the urban environment, you'll be
downtown, this is great. Or no way my child's going to be there. We need to be up there in the safe, you
know, neighborhoods of the ambassador. So I got stuck up in the Northwest part of Washington American
University. So. It's such a horrible school to go to mean, the place, you know. I lived in Bethesda,
Maryland, for about nine months of my life, and we used to go to Georgetown all the time. And there was
a bar there called Mr. Smith's. Did you ever go there? Yes, yeah, the piano, yeah, yes, piano bar. Like we
we may have been there at the same time. Yeah, we're the same age. Yeah, it's like it was like the like I
remember. I mean, I was probably the guy trying to. Pick you up. Probably saying, you know, I was a
debate guy. I was class president. You are like oh, yeah, I don't need that. It was so fun, but what a cool
experience for you to have. And then, so you're living up there. So you're going to school in DC.
You're exposed to so much of the politics. Is that what got you in? I mean, you just kind of continued
down that path. It did. Yeah. I got selected into a program where you had to do an internship, and I
interned for Union Pacific Railroad only because my dad was fascinated with the railroad and with model
trains. So I thought, Geez, this would be kind of fun to go work at Union Pacific. I was their first intern
ever, and I was making 20 an hour which was a pretty wealthy college student. Yeah. And that led me to
my first job.
I was on a train trip. They used to bring out their old steam engine and wine and dine members of
Congress. And I met a senator from Nebraska because Union Pacific was headquartered in, still is in
Omaha, Nebraska. And I met a senator on that train trip from Houston to New Orleans. And he was very
intoxicated. And he said, what are you doing when you graduate? And I said, I don't know, law school,
business school or something. You know, I don't know, law school, business school, or something. He said,
Why don't you come work for me? And I took advantage of that pretty much right away. You wrote your
job offer right then and there, like, sign, please, sir. Did he ever show her up? Probably not. Yeah. He's
now president. Just kidding. No, he's okay. Yeah. So, I mean, and that was just like your foot into that
world.
And you. Oh, it was the serendipity. But you got to work on some different administrations as well, too, in
your time, right? Yeah, yeah. I worked for Chuck Hagel, Nebraska. I worked for him for a couple of years.
And then I was his driver of all jobs, which was actually, you know, my dad was pretty angry, right? Like,
I didn't pay for college for you to drive some guy around Washington, DC but it became the most trusted
position because you heard all the phone calls, right? So when he's calling presidents and world leaders
and secretary of states and other senators, you're hearing conversations that are, you know, when you're 22
years old, are just like really amazing, you know, and you're really seeing DC the inner workings of DC
but DC, the inner workings of DC. But yeah, President Bush got elected. And well, you remember in
2000, it was quite an interesting election. Yeah, yeah. And he came out of it. And then so in February, so
usually a president starts to fill their administration with staffers around that springtime, April and May,
because by then they've got most of their cabinet in. And I went to go, yeah, a guy I knew from Union
Pacific.
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Went to the Department of Transportation and asked me to work for him. And I got into the Bush
administration. And then I met Normanetta, who was the secretary at the time. He was the first Asian
American mayor and congressman, and all kinds of first. He's kind of a hero in the he is a hero in the
Asian American community, and he has since passed. But he was a congressman forever, and he was the
Democrat that George Bush put at transportation. And I actually interviewed with him of all people, and
he really got. To like me, and I became his body man essentially. Like you're, you know how you see on
news they're making light of the young woman who works for Donald Trump, and she never leaves his
side. Well, that's who I was for Secretary Manetta. I never left his side, and I was at his side on 9 11 matter
of fact. He was having breakfast with the deputy prime minister of Belgium in his office. And we had to
interrupt him twice. Obviously, the second time is when the plane hit the second time or the second plane
hit the towers. And he obviously then got him in the motorcade and rushed him to the White House.
And then minutes later, he then ordered all the planes down for the first time in American history. 5000
airplanes in two and a half hours landed safely all around the country. Pretty amazing. And and air traffic
control came to a because they had to try to find what was still out there. And we know today, I think some
is probably still classified. I think some still think there was more out there. But obviously, and I was just
reading this story today about the Shanksville plane that. Pennsylvania? Yeah, these mostly, at some point,
everybody on that plane knew what was happening and they knew their fate. I was just reading a story
about one of the flight attendants who led the effort of the other flight attendants to boil water in the back
galley, because you can remember the terrorists are now in the front, and they boiled water. Remember, the
terrace are now in the front, uh, and they boiled water, uh, and they collected everything they could. And
as we know, you know, that one passenger said, Let's roll or something, and and they all fought their way
into the cockpit and essentially, you know, saved probably so many lives probably thousands of lives,
landmarks, all kinds of things, and sacrificed themselves.
But, uh, but yeah, that was a crazy day. Well, obviously, the work probably one of the worst days in
American history there. Uh, and you were like the fish on a shark, like you were like attached to him, so
you were hearing. Yeah conversations like you all the conversations. Yeah, well, he went to the White
House. I went to our-- so the Department of Transportation runs the FAA. And FAA has its own bunker, if
you will. I don't know any other word. Command center or something. So we all went in there and
watched these big major screens have all the flights. And you can watch all the planes land and stuff. So
we watched it from there. And then at the end of it, we pretty much stayed the night. And then, then
Wednesday came. We all remember that day of just to figure out and we were glued to the televisions as
all of us were. Now, the next day, Thursday, we tried to get commercial flights back up because you had to
keep the economy going. And so we took the first commercial flight, Secretary Mineta and I and obviously
others from Baltimore to Chicago.
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And we met President Bush there in Chicago for a big rally to try to get people to fly again, which is good
of like hard to do, but we tried. And then Congress passed a major piece of legislation, which is now the
Transportation Security Act, and that built TSA. And so we had one year to build the largest federal
agency ever built since the Pentagon. And we did that. And obviously, it's survives to this day. And it's
been, for the most part, pretty successful 25 years later when you think about it. It's crazy to think that we
ever flew without that. It's crazy. I mean, it's just. Yeah, the terrorists technically didn't break any laws.
They had knives that were allowed, and the cockpit wasn't really technically locked. I mean, it's like crazy
to think about. But, you know, they technically, unfortunately, knew what they were doing.
But yeah, it was actually an interesting story about Billion TSA. So Norm Mineta was sitting around and
he goes, How in the world are we going to do this? Like, obviously, you know, and of course, I'm a young
man, right? So I'm just kind of like, you know, watching us from afar, chiming in when I can. But all the
older people, if you will, of the day were, you know, trying to figure out how to do this. And so Mineta
was smart enough where he said, We got to bring in experts. So he started to call CEOs from around the
country. So for example, he called Michael Eisner of Walter. Disney World, uh, and he said, Uh, Mr.
Eisner, I need your vice president of lines. You all know how to get people from A to B, probably the best
in the world. And I need the person who's the smartest on that to fly to Washington and help us build TSA.
So, of course, Eisner said, Yeah, you've got him. Yeah, I don't know, he's in the line right now, he'll get
back to you later, right? Right? He's busy, he showed up. Yeah, that's right.
And so we did that with companies all over the country Marriott, Intel, you name it. And so before you
know it, within a week, we had really now a collection of experts on all different areas. And that's how
they built TSA. It's just pretty incredible. And we couldn't pay them. The company still had to pay them. Is
there a book that tells that part of the story anywhere? Not really. I think there's bits and pieces here and
there, but I always thought that'd be an interesting kind of an MBA study or some sort of thesis of some
sort.
But because the companies had a key to keep paying those people. I mean, these were multi million dollar
executives, right? I mean, and they, you know, they had to be away from their families and all that. But I
think that's why it's been so successful. I think it was built right. And then we, every time there was a new
set of TSA agents that would come on for the first time, he would want to swear them in. So no matter
what time of day, the FAA owns 100 airplanes. So you know how airplanes have tail numbers.
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So the FAA owns through N100. So the next time you see a big long tail number, you can think to
yourself, there is an N1 that actually starts the process. But we took N1 around the country and swore in
all these TSA agents who are so proud, I mean, rightfully so of defending their country. Obviously, we we
had to get the Air Marshal program up and running again when we funny story is, the Air Marshal
program really didn't exist. We had to fly to Atlantic City and it was like a movie set like we dry. It was
actually at the airport, but we drove around, you know, in our cars, and we get to the air marshal place, it
was this rusty old like, it looked like an old West town, you know, because it had these old airplanes that
they trained on. And literally walked into like a trailer home. And there was like, it looked like, you know,
like a couple of drunk guys just sitting there, you know, like, they'd never been called ever in their lives.
And we're like, Are you guys the air marshals? They're like, Yeah, you know, we're like, Well, we're going
to have to wake you up and expand this program overnight.
" And so luckily, we had law enforcement people out there obviously raised their hand, you know,
obviously right away. I mean, it was, you know, there was now, I mean, by that Thursday, there were
armed guys on every flight, you know, in America. And that lasted for a while. I don't think it really exists
today. Maybe it's those, but a lot of these guys would get into trouble because they're away from their
wives. So, there were problems right away because they were, you know, they had some money in their
pocket or, you know, they got, they met flight attendants.
And, you know, one thing, it was a, Little bit of a HR disaster. How long before TSA was operational from
the onset? Well, yeah, we essentially had it running up in a matter of months. I think it became official in a
year after. So by November of 2022. That's when the Department of Homeland Security was created. So it
that's when it officially all those departments then went to Department of Homeland Security. So you
know, the Coast Guard and Secret Service and ATF and all the you know, a lot of those law enforcement
issues all went to Department of Homeland Security.
That's what was good. Who was it? You George Allen security then. Who was remember Tom Ridge, the
governor of Pennsylvania? Do you remember Tom Ridge? Nice guy, actually. He was Vietnam veteran and
stuff. But the scary thing, well, there was a lot of scary things. But I guess the scary internal thing was you
had Dick Cheney and John Ashcroft and some others who were pretty far to the right, probably of George
W. Bush, and they wanted to. You know, screen all Arab Americans essentially profile, and there was a
moment. I wasn't there, but there is history of this that Normanetta was interned as a young Japanese
American boy in our Japanese American camps during World War II. You know, we actually did have
prison and work camps in this country. And ironically, I just came back from a trip from Germany and
learned that Adolf Hitler copied a lot of our. Our own internment camps that we did to Japanese
Americans. But he was a young boy in Heart Mountain, Wyoming. And George W. Bush knew that story.
And I guess the history is that during this conversation in cabinet, George W. Bush actually stood up and
said that I will not let what happened to Norm happen again in this country.
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Wow. Yeah. So that's a, you know, you could think about what the opposite could have happened, right?
We could have, you know, those places where a lot of Arab Americans live, you know, Michigan,
Dearborn, Michigan, a lot, you know, could have been a different scene. So you know, that's one of those
history, you know. But, you know, say anything about George W. Bush. He kind of rose to the occasion a
little bit. I mean, he can probably question the Iraq War, but, you know, he stood on that pile, remember?
And he answered that guy. I mean, it was, I don't know how any of us could have handled that. So he did a
pretty good job. But yeah, I worked there for a couple of years. And then Chuck Hagel wanted to run for
president. He was thinking about running for president in 2008. He asked me to help him put all that
together.
So I essentially kind of raised money and put together a presidential campaign plan. But then two of his
best friends eventually ran for president, Barack Obama and John McCain. So we thought it was gonna be
Hillary Clinton and Mitt Romney. We thought two established kind of boring candidates. We thought
there'd be room for a renegade. We actually formed a party ticket, if you will, Michael Bloomberg. We
thought a Bloomberg Hagel ticket would be really interesting and kind of what the country needed. But we
got Barack Obama, which I think was the right person for the right time in 2000 history was made and
Hagel retired. So I didn't have a job. And so so I went to go work for Barack Obama. I am a Republican
congressman, became the secretary of transportation, Ray LaHood. And he called me and I worked there
for all eight years of Barack Obama.
So then we traveled the world. We traveled to first of all, do you have him on speed dial? I have Ray
LaHood, but I don't Have Barack Obama. I did play golf with him twice. I did play golf with him. There
you go. But how cool is that you got to work in two different administrations, two different sides of the
party, which is amazing, and got to experience all that at such a young age? I have so many questions for
you. OK, so first of all, I mean, you were going, right? When that happens, it's like all hands on deck and
go time where you were like Was there a time where you were like, oh, my goodness, like the world, like
we're all going to die? Did you ever feel that way? I mean, yeah, I mean, a little bit. Sure. I mean,
Washington, DC was crazy.
I mean, it was fighter jets. Right. And I mean, it was the Pentagon. You could see the smoke from the
Pentagon. I mean, it was it was kind of crazy. We had we had drilled once before then when I was in the
Obama administration, we would drill every year. But we go to a place called Mount Weather in Maryland
and it's a very deep you know, kind of classified. Essentially, you can run government from Mount
Weather, and the whole government would go there and train once a year. And, you know, we thought we
would be going there, but it was, I think it was just too fast.
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We just, you just had to keep going. But yeah, sure. I mean, it, you know, and you just, you know, and then
you kept hearing of all the idiots trying to get on planes with all kinds of stuff, you know. So, Well, okay,
so oh my gosh, my mind is like going in an overdrive right now. So, okay, so you did this many years ago,
but this is like, you know, you were part of, you were getting classified information at that time, right?
Like you were told this. So, and there's multiple people like you around the world who were privy to
information that now, now