November 6, 2025 • 16 mins
Kenneth C. “Kenn” Ricci is an American aviation entrepreneur and the Principal of Directional Aviation Capital, which owns or invests in various aviation enterprises including Flexjet, where he also serves as Chairman. Kenn began his aviation career as an Air Force ROTC cadet at the University of Notre Dame and started his first company, Corporate Wings, in 1980. His love of aviation had him founding, acquiring or financing a broad range of aviation companies and ideas over his career. He has assembled one of the largest groups of private aviation companies which together account for over $4.0 billion of revenue, operate over 300 aircraft and employ over 5,000 individuals. Kenn was honored as an Ernst & Young Entrepreneur of the Year in 2000 and has been named one of the most influential people in aviation by Aviation International News. In 2005, Kenn led the restructuring of the Mercury Air Centers, a $200 million company operating aircraft support facilities at 24 different airports. He sold the company to Macquarie Infrastructure Trust in 2007 in a deal valued at $615 million. In 2010, Kenn received the Harvard Business School’s Dively Entrepreneurship Award. In 2011, Kenn was the youngest recipient of the prestigious William A. “Bill” Ong Memorial Award for extraordinary achievement and extended meritorious service to the general aviation industry.
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Episode Transcript
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Speaker 1 (00:00):
This is CEOs you should know, and I've got a
great one here for you today. Cleveland born and bred
Ken Ricky, who is an aviation entrepreneur, chairman of flex Jet,
leading provider of private jet travel, Saint Ignacious Grad, Notre
Dame Grad. You know, as a Michigan fan, I found
a little tension at first, but it's okay now, Well
I would I would.
Speaker 2 (00:20):
Have gone to Michigan if I couldn't get into Notre Dame.
Speaker 3 (00:25):
You know, let's go way back though.
Speaker 1 (00:27):
I mean, when did you first realize you had a
passion for flight?
Speaker 4 (00:32):
You know, when I was when I wanted to go
to Notre Dame. I actually grew up in South ucud
and we had very tiny homes and I remember going
up for a visit and I heard my parents talk
in the other room about the fact they couldn't afford
for me to go to Notre Dame. So I got
up there for a visit and I'm like, I got
to figure this out. So I go to the school
(00:53):
and I asked, where do you get this financial aid open?
They said, well, you kind of missed the window for
financial aid unless you want to go into the military.
Because the ROTC application was still available, so I thought, okay,
it's the first time I thought about flying, So I
decided to go in. And I'm like, I think I'll
go be a Navy pilot. Don't ask me why that happened.
So I'm standing outside the ROTC. This is before there
(01:14):
were cell phones, and I'm trying to copy down the
number because a Saturday of the Navy ROTC number, so
I could call them Monday and tell him I'm interested in.
Speaker 2 (01:21):
Becoming a Navy pilot.
Speaker 4 (01:23):
And somebody taps me on the shoulder and they said,
excuse me, can I help you? And I said, yes,
I'm an incoming freshman interested in going flying in the Navy.
And he looks at me and he says, are you
sure you've been admitted here? Because the Navy has ships
and the Air Force has planes, and I'm head of
the Air Force detachment. My name's Colonel Muller, and I
would love to have you as one of our candidates.
(01:43):
And that was really I just felt if I had
to be in the military, it's like from.
Speaker 2 (01:47):
Every boy's dream, right baseball and being a pilot.
Speaker 3 (01:50):
Well, Kenna.
Speaker 1 (01:51):
It's kind of surprising me though, because I would think
that being a pilot just like being a doctor. It's
like I believe some people are born to do certain things.
Do you feel you were born to fly or do
you feel that once you got a taste of it,
you just kind of I was, all of a sudden,
we're all in.
Speaker 2 (02:07):
I was born to think that traveling was romantic.
Speaker 4 (02:11):
The days when my father would go to Cleveland Hopkins
Airport and we would drop him off, and I had
to work a tie to go drop my father off
to take a flight, right because those were the air
that was the era of a really romantic flying. And
my father loved to travel. We spent every spare dollar
we had traveling somewhere. So it wasn't necessarily a love
to fly, but it was a love to travel, and
(02:32):
it was something about the romance of seeing new places
and going having new experiences of.
Speaker 3 (02:37):
What attracted Do you remember that first solo flight?
Speaker 2 (02:40):
Oh ever, of course you do, of course, because you're
scared out of your mind.
Speaker 4 (02:44):
I mean you absolutely think this this is how my
life good Dan, And I will tell you, yeah, there's
you know when when you when you take off, I
was like, man, I'm a little wetness under my armpits here.
It is, but it's also it is so confident building.
I would tell you that we had a program years
(03:06):
ago that we would do with inner city kids where
we would pay to get them to solo because it's
such a confidence builder to get in this machine and
be able to go and fly around the pattern, come
back and land. And still there's even a program we
do it Purdue University for vet's who've lost limbs, and
we have a plane specially designed where you can fly
(03:28):
it with without a limb, and it's kind of it's
just to kind of build confidence.
Speaker 2 (03:33):
And so that's what it does for you for sure.
Speaker 1 (03:35):
I don't know during the course of this interview, if
I'm going to get a better quote, then this is
how my life could end, because that's exactly what I
would be thinking too. I'm terrified of flight, Oh you are,
I'm not. I mean, when I'm up there, I'm kind
of thinking. I mean, there's so many bolts keeping this
thing together. There's so many things that have got to work.
What if just something good? I mean, that's the mindset
(03:57):
I have when I get in the plane. I got
to learn to let that.
Speaker 2 (04:00):
Probably people that are afraid to fly sometimes.
Speaker 4 (04:02):
Are are typically people like you that have jobs where
they're confident, they're in charge, they're directing, and they feel
like they're a little bit out of control, right, and
so more more knowledge of aircraft would probably help you.
Speaker 3 (04:14):
Talking to Ken Ricky right now.
Speaker 1 (04:16):
This is a CEO you should know, Saint Ignacious grad
Cleveland guy and the chairman of flex Jet, leading provider
of private jet travel. Let's go back to nineteen eighty.
You found your first company, Corporate Wings. What made you
want to found a company? And could you have ever
envisioned it would become what it is today? So not
to correct, I didn't find it. I found it.
Speaker 4 (04:36):
I bought it, and I was I had gone from
the military where I learned to fly, and my whole
life I just love to fly. And I went to
Northwest Orient where I got furloughed. Furloughed is a fancy
name for you don't have a job. And then I
came back to Cleveland, where I was a pickup pilot
pilot you know in the area. If you needed a
spare piot, you've hired me. That was a very kind
(04:57):
of inconsistent work. And so somebody came to me and said,
would you want to buy Corporate Wings? And I thought, well,
I'll be able to fly more because I'll control the company, right,
So they so they ended up offering me to buy
the company. They really wanted to get out of the business.
And I bought the company for twenty seven thousand, five
hundred and I called my dad and I asked him.
(05:17):
I told him I was going to buy this company,
and he said, well, how are you going to pay
for it? And I said, well, the company has twenty
seven thousand dollars in the bank, so I think I
can like buy it and use the twenty seven thousand
to pay alf the owner. And he said, we are
you getting the other five hundred? I said, why do
you think I called you? So I bought Corporate Wings.
But I was actually at the same time I bought it,
I was in law school here at Cleveland Marshall, and
(05:40):
so I was it just gave me the ability to
more manage what I was trying to do. It's prioritize
my flying and kind of continued to grow. But you
have to think at that point in time, I wasn't
thinking of this as a business.
Speaker 2 (05:51):
I was thinking of it as flying and as more travel.
Speaker 1 (05:54):
So when you sit here and you look back, Okay,
so you have built one of the largest private aviation
platforms globally. You're generating over four billion in annual revenue.
You're operating more than three hundred aircraft. You've received big
time awards, Ernst and Young Entrepreneur the Year Award, Harvard
Business Schools Entrepreneurship Award, Living Legends of Aviation, Lifetime Aviation
(06:16):
Entrepreneur Award. When you think back of what you have accomplished,
what stands out?
Speaker 4 (06:24):
What are you most proud of. I'm most proud of
the culture. I think that it's culture beat strategy. You've
probably heard that term before, but the culture, because the
people that work in aviation, they're they're really Aviation is
a romantic profession. It's like being an actor. It's like
being in theater. It's probably like radio. People do this
not for the money necessary, but because they love what
(06:46):
they do, right, and so being able to bottle that
passion and to walk in and to think about the
culture we have there as a company is what I'm
most proud of. And I think and that was only
because I get you know, who I him as a
person and what I do clearly align.
Speaker 1 (07:02):
I'm glad you brought that up. I want to know
what has made you who you are as a person.
What about Cleveland? Growing up in Cleveland, do you think
has directly impacted you the most and made you the
success you are?
Speaker 4 (07:17):
You know, it's it certainly was Cleveland, right, Because if
you look at people that were influential in my life,
I would tell you that I learned from my father.
I learned that you should always operate in as a
as a person of class. And he would say things like, uh,
to be a person of class never puts somebody else down, right,
(07:37):
they always are behind. And it's funny because I don't
know if you knew that I was Bill Clinton's pilot line.
Speaker 2 (07:43):
I rant, Thundercat, We'll back, Yes, we'll come back to that. Yeah.
Speaker 4 (07:49):
So because I learned something from him too that I
that shouldn't go and notice. So I think I learned
from my father that I also learned because I was
you know, I always say my employee meetings. When I
first started the company, there were there were six of us.
We went to a bar and had a beer, and
that's how we did a company meeting. So how do
you build now you have to have other people act
like you would if you're not there, right, And I
(08:11):
always tell our direct reports the number one skill set
to be successful as a leader is empathy, because you
can't if people know you understand how they think that.
This is what the military does, right. They teach you
to come together so you work off each other.
Speaker 3 (08:25):
Right.
Speaker 2 (08:26):
So as a leader, if you develop a skill of empathy,
people will follow you.
Speaker 1 (08:32):
Those are those are very deep and very important words
right there, because I totally one percent agree with you,
And I've read a lot on great leaders throughout history
and they pretty much say the same thing that you did.
If you can connect with somebody, they will follow you.
And if they know you care about them, they will
follow you.
Speaker 4 (08:51):
Right And and but you know, I wrote a book
called Managed by Trust twenty three years ago to try
to capture this idea. I mostly wrote it for people
that I thought would be managing in my place, people
that had to go manage a division in Europe. And
I'm not there to tell them how to lead.
Speaker 3 (09:07):
Right.
Speaker 4 (09:07):
But when you want people to to be part of
being empathetic, part of getting people to follow you is
to believe. Is people have to believe you're telling them
the truth, good or right, right, right, good or bad.
They have to believe you're being straight with them.
Speaker 1 (09:20):
This is the CEOs you should know. Ken Ricky is
a Cleveland native, also aviation entrepreneur. All right, let's get
to Bill Clinton. So how did you become his personal pilot?
Speaker 4 (09:30):
So in as I was developing Corporal Wings, a company
we talked about earlier, I got into a specialty niche
of flying rock tours.
Speaker 2 (09:38):
Concert tours.
Speaker 4 (09:39):
Okay, I did Bruce Springsteen and Barbara Streisan, Elton John.
Speaker 3 (09:42):
Tell me you did Motley Crue, Bryan Adams. That's cool, yeah, yeah, yeah.
Speaker 4 (09:49):
But but but these these these tours run two three months,
they run through a season. They're a little longer now,
but at that time, they were two three months, and
you typically got like double or triple the pay because
you were you didn't have to work the rest of
the year.
Speaker 2 (10:02):
But so you charged extra for a short term gig.
Speaker 4 (10:05):
And I get a call from a guy that says,
have you ever done a political campaign? And I said, no,
but how long is it for? Because how long I
am getting price for it? Right? He said, well, for
it's for thirteen months. And I said, thirteen months. What's
the guy running for He said, well, he's running for president.
He said, well, who is it? He said, it's the
governor of Arkansas. And the governor of Arkansas is not
going to need a plane for thirteen months. This guy
has no chance of becoming president.
Speaker 3 (10:27):
The same thing.
Speaker 4 (10:28):
Yeah, And I ended up flying him through the inauguration,
no kidding, So because you know, after they're elected and
before they're inaugurated, and they still use private aircraft.
Speaker 3 (10:37):
So give me give me.
Speaker 1 (10:38):
A Bill Clinton story or a personal experience with him
that I don't know resonated with so.
Speaker 4 (10:44):
So, one of my first meetings with him, after one
on one, he's the he's the governor, he's the governor,
and we go to it. We go to a little
hamburger joint. This is the first time I've met him,
and of course it takes him. He it takes them
ten minutes to get through the bar. There's four people there,
but he has to talk each one of my fo
and we finally sit down and the waitress comes right
over and says, what would you like? And he said,
(11:04):
I'm going to have a burger with your sweet potato fries.
And I said, I'll have the same and he looks
over at me.
Speaker 2 (11:09):
I said nothing to the man.
Speaker 4 (11:10):
And he looks at me, and he says, I'm way
too fat and my cholesterol is too high, but I
just love them sweet potatoes.
Speaker 3 (11:18):
Which is what you would expect somebody from Arkansas.
Speaker 2 (11:21):
To say exactly.
Speaker 4 (11:22):
And years later I not years later, months later I
got to know him better and thought I could start
to ask him because we became friends, right, And I
said to him, I remind him of this conversation, and
he said, you know, if you want to ingratiate yourself
to someone, start with something that's wrong with you. When
you tell someone I'm way too short and I eat
(11:42):
too much, people think you trust them because you're sharing
a fault. And so if you want people to kind
of ingrace, if ingratiate yourself to someone, tell him, tell
him one of your faults. And it's so contrary to
how we think today. Right, we live in a social
media world. Will we tell you only the good stuff
about our right? So think about the fact that we
might artificially be putting up barriers to having better relationships
(12:05):
just by telling people what's.
Speaker 3 (12:06):
Wrong with that? Yeah, No, that's that's great. Insight. That's
that's great advice.
Speaker 1 (12:10):
Give me a rock star story, give me I mean,
there was there any anybody who left again a certain
impression on you from all the rock stars.
Speaker 3 (12:19):
You flew around.
Speaker 2 (12:20):
Well, I would tell you that.
Speaker 4 (12:21):
You know, the misperception about celebrities is that that I
always say my celebrity. God is fair, because if God
made somebody to be a phenomenal singer and then made
them unbelievably intelligent, that would be an unfair God. Right,
And so most of these people are really really good
(12:42):
at their craft, but they're not very broad, okay, I mean,
like you get. And by the way, they practice a
hell of a lot more than you think. When I
would watch Bruce Ringsteen, you he does that concert. You know,
he's known for his four hour concerts. Right, what people
don't know he'll rehearse three hours before a four hour
concert that their sound checks will run hours. That's correct, Okay,
(13:05):
Michael Jackson was unbelievably. It was unbelievably myopology focused on details.
In fact, today in our company, one of our fundamental principles.
Of course, we have people lives in our hands, right,
we're flying. But our fundamental principles, fanatical attention to detail.
And I think I learned that by watching these rock
stars who were so good, but they come up there
(13:27):
and they look so natural, right, but you'd be amazed
at how much time they spend getting there.
Speaker 3 (13:34):
What is the future of flight in your mind?
Speaker 2 (13:38):
Well, I think.
Speaker 4 (13:40):
There's actually you know, we've kind of bifurcated flight, right,
We've really gone into two directions. We have almost two
economies in flight. We have the airline economy, which has
one experience to it, and we have a private experience.
And one of the reasons that the private experience is
growing is because of the degradation of the airline experience.
(14:01):
And the one thing I hear from our clients very
often is that I'm now spending a disproportional amount of
my income. I'm flying privately because that's an experiential thing
and it saves me time, it saves me stress.
Speaker 2 (14:15):
And so when you.
Speaker 4 (14:16):
Ask about the future of flight, I almost have to
answer the question in two vernaculars. One is are we
talking about the private side of flight or are we
talking about the commercialization of flight?
Speaker 3 (14:26):
Right?
Speaker 2 (14:27):
So, I think I think we're down these paths.
Speaker 4 (14:29):
I think of anything COVID solidified the fact that we're
not going to take commercialized flight and bring it back
to the fifties where it's romantic and we get we
get a beautiful place to have a beautiful dinner on
a long flight and there's an actress sitting next to
us that we can romance. I think those days are gone,
and so we're going to get more commercial, more efficient
in terms of how we do it right, automatic check
(14:51):
in facial recognition will speed up the whole process of
getting onto a plane efficiently. So I think facial recognition
is being it's actually tried in over there's many overseas
stops today where you go through TSA through racial recognition, right,
So that's what's coming and that'll make commercial flying more
palatable because the lines will be simpler and so on.
The private flying is is it's just a different economy,
(15:15):
you know, it's a and that economy is growing in
a big way because we're going through a huge transfer
of wealth right now. There is a huge amount of
the baby boomers and the post World War two who
kept a phenomenal amount.
Speaker 2 (15:29):
Of wealth that they kept quiet.
Speaker 4 (15:31):
You know, there was there was there was the unrecognizable rich,
and now that wealth is being transferred, and this is
why today our client is almost ten years younger than
it was pre Codd.
Speaker 3 (15:43):
All right, I'm going to end on this one.
Speaker 1 (15:46):
When somebody meets you, what do you hope they walk
away thinking about Ken Ricky, That.
Speaker 4 (15:55):
I'm passionate about what I do and that I'm compassionate
about how I do it.
Speaker 3 (16:00):
I got that feeling. M M. This is CEOs you
should know, and you just heard Ken Ricky
This is CEOs you should know, and I've got a
great one here for you today. Cleveland born and bred
Ken Ricky, who is an aviation entrepreneur, chairman of flex Jet,
leading provider of private jet travel, Saint Ignacious Grad, Notre
Dame Grad. You know, as a Michigan fan, I found
a little tension at first, but it's okay now, Well
I would I would.
Speaker 2 (00:20):
Have gone to Michigan if I couldn't get into Notre Dame.
Speaker 3 (00:25):
You know, let's go way back though.
Speaker 1 (00:27):
I mean, when did you first realize you had a
passion for flight?
Speaker 4 (00:32):
You know, when I was when I wanted to go
to Notre Dame. I actually grew up in South ucud
and we had very tiny homes and I remember going
up for a visit and I heard my parents talk
in the other room about the fact they couldn't afford
for me to go to Notre Dame. So I got
up there for a visit and I'm like, I got
to figure this out. So I go to the school
(00:53):
and I asked, where do you get this financial aid open?
They said, well, you kind of missed the window for
financial aid unless you want to go into the military.
Because the ROTC application was still available, so I thought, okay,
it's the first time I thought about flying, So I
decided to go in. And I'm like, I think I'll
go be a Navy pilot. Don't ask me why that happened.
So I'm standing outside the ROTC. This is before there
(01:14):
were cell phones, and I'm trying to copy down the
number because a Saturday of the Navy ROTC number, so
I could call them Monday and tell him I'm interested in.
Speaker 2 (01:21):
Becoming a Navy pilot.
Speaker 4 (01:23):
And somebody taps me on the shoulder and they said,
excuse me, can I help you? And I said, yes,
I'm an incoming freshman interested in going flying in the Navy.
And he looks at me and he says, are you
sure you've been admitted here? Because the Navy has ships
and the Air Force has planes, and I'm head of
the Air Force detachment. My name's Colonel Muller, and I
would love to have you as one of our candidates.
(01:43):
And that was really I just felt if I had
to be in the military, it's like from.
Speaker 2 (01:47):
Every boy's dream, right baseball and being a pilot.
Speaker 3 (01:50):
Well, Kenna.
Speaker 1 (01:51):
It's kind of surprising me though, because I would think
that being a pilot just like being a doctor. It's
like I believe some people are born to do certain things.
Do you feel you were born to fly or do
you feel that once you got a taste of it,
you just kind of I was, all of a sudden,
we're all in.
Speaker 2 (02:07):
I was born to think that traveling was romantic.
Speaker 4 (02:11):
The days when my father would go to Cleveland Hopkins
Airport and we would drop him off, and I had
to work a tie to go drop my father off
to take a flight, right because those were the air
that was the era of a really romantic flying. And
my father loved to travel. We spent every spare dollar
we had traveling somewhere. So it wasn't necessarily a love
to fly, but it was a love to travel, and
(02:32):
it was something about the romance of seeing new places
and going having new experiences of.
Speaker 3 (02:37):
What attracted Do you remember that first solo flight?
Speaker 2 (02:40):
Oh ever, of course you do, of course, because you're
scared out of your mind.
Speaker 4 (02:44):
I mean you absolutely think this this is how my
life good Dan, And I will tell you, yeah, there's
you know when when you when you take off, I
was like, man, I'm a little wetness under my armpits here.
It is, but it's also it is so confident building.
I would tell you that we had a program years
(03:06):
ago that we would do with inner city kids where
we would pay to get them to solo because it's
such a confidence builder to get in this machine and
be able to go and fly around the pattern, come
back and land. And still there's even a program we
do it Purdue University for vet's who've lost limbs, and
we have a plane specially designed where you can fly
(03:28):
it with without a limb, and it's kind of it's
just to kind of build confidence.
Speaker 2 (03:33):
And so that's what it does for you for sure.
Speaker 1 (03:35):
I don't know during the course of this interview, if
I'm going to get a better quote, then this is
how my life could end, because that's exactly what I
would be thinking too. I'm terrified of flight, Oh you are,
I'm not. I mean, when I'm up there, I'm kind
of thinking. I mean, there's so many bolts keeping this
thing together. There's so many things that have got to work.
What if just something good? I mean, that's the mindset
(03:57):
I have when I get in the plane. I got
to learn to let that.
Speaker 2 (04:00):
Probably people that are afraid to fly sometimes.
Speaker 4 (04:02):
Are are typically people like you that have jobs where
they're confident, they're in charge, they're directing, and they feel
like they're a little bit out of control, right, and
so more more knowledge of aircraft would probably help you.
Speaker 3 (04:14):
Talking to Ken Ricky right now.
Speaker 1 (04:16):
This is a CEO you should know, Saint Ignacious grad
Cleveland guy and the chairman of flex Jet, leading provider
of private jet travel. Let's go back to nineteen eighty.
You found your first company, Corporate Wings. What made you
want to found a company? And could you have ever
envisioned it would become what it is today? So not
to correct, I didn't find it. I found it.
Speaker 4 (04:36):
I bought it, and I was I had gone from
the military where I learned to fly, and my whole
life I just love to fly. And I went to
Northwest Orient where I got furloughed. Furloughed is a fancy
name for you don't have a job. And then I
came back to Cleveland, where I was a pickup pilot
pilot you know in the area. If you needed a
spare piot, you've hired me. That was a very kind
(04:57):
of inconsistent work. And so somebody came to me and said,
would you want to buy Corporate Wings? And I thought, well,
I'll be able to fly more because I'll control the company, right,
So they so they ended up offering me to buy
the company. They really wanted to get out of the business.
And I bought the company for twenty seven thousand, five
hundred and I called my dad and I asked him.
(05:17):
I told him I was going to buy this company,
and he said, well, how are you going to pay
for it? And I said, well, the company has twenty
seven thousand dollars in the bank, so I think I
can like buy it and use the twenty seven thousand
to pay alf the owner. And he said, we are
you getting the other five hundred? I said, why do
you think I called you? So I bought Corporate Wings.
But I was actually at the same time I bought it,
I was in law school here at Cleveland Marshall, and
(05:40):
so I was it just gave me the ability to
more manage what I was trying to do. It's prioritize
my flying and kind of continued to grow. But you
have to think at that point in time, I wasn't
thinking of this as a business.
Speaker 2 (05:51):
I was thinking of it as flying and as more travel.
Speaker 1 (05:54):
So when you sit here and you look back, Okay,
so you have built one of the largest private aviation
platforms globally. You're generating over four billion in annual revenue.
You're operating more than three hundred aircraft. You've received big
time awards, Ernst and Young Entrepreneur the Year Award, Harvard
Business Schools Entrepreneurship Award, Living Legends of Aviation, Lifetime Aviation
(06:16):
Entrepreneur Award. When you think back of what you have accomplished,
what stands out?
Speaker 4 (06:24):
What are you most proud of. I'm most proud of
the culture. I think that it's culture beat strategy. You've
probably heard that term before, but the culture, because the
people that work in aviation, they're they're really Aviation is
a romantic profession. It's like being an actor. It's like
being in theater. It's probably like radio. People do this
not for the money necessary, but because they love what
(06:46):
they do, right, and so being able to bottle that
passion and to walk in and to think about the
culture we have there as a company is what I'm
most proud of. And I think and that was only
because I get you know, who I him as a
person and what I do clearly align.
Speaker 1 (07:02):
I'm glad you brought that up. I want to know
what has made you who you are as a person.
What about Cleveland? Growing up in Cleveland, do you think
has directly impacted you the most and made you the
success you are?
Speaker 4 (07:17):
You know, it's it certainly was Cleveland, right, Because if
you look at people that were influential in my life,
I would tell you that I learned from my father.
I learned that you should always operate in as a
as a person of class. And he would say things like, uh,
to be a person of class never puts somebody else down, right,
(07:37):
they always are behind. And it's funny because I don't
know if you knew that I was Bill Clinton's pilot line.
Speaker 2 (07:43):
I rant, Thundercat, We'll back, Yes, we'll come back to that. Yeah.
Speaker 4 (07:49):
So because I learned something from him too that I
that shouldn't go and notice. So I think I learned
from my father that I also learned because I was
you know, I always say my employee meetings. When I
first started the company, there were there were six of us.
We went to a bar and had a beer, and
that's how we did a company meeting. So how do
you build now you have to have other people act
like you would if you're not there, right, And I
(08:11):
always tell our direct reports the number one skill set
to be successful as a leader is empathy, because you
can't if people know you understand how they think that.
This is what the military does, right. They teach you
to come together so you work off each other.
Speaker 3 (08:25):
Right.
Speaker 2 (08:26):
So as a leader, if you develop a skill of empathy,
people will follow you.
Speaker 1 (08:32):
Those are those are very deep and very important words
right there, because I totally one percent agree with you,
And I've read a lot on great leaders throughout history
and they pretty much say the same thing that you did.
If you can connect with somebody, they will follow you.
And if they know you care about them, they will
follow you.
Speaker 4 (08:51):
Right And and but you know, I wrote a book
called Managed by Trust twenty three years ago to try
to capture this idea. I mostly wrote it for people
that I thought would be managing in my place, people
that had to go manage a division in Europe. And
I'm not there to tell them how to lead.
Speaker 3 (09:07):
Right.
Speaker 4 (09:07):
But when you want people to to be part of
being empathetic, part of getting people to follow you is
to believe. Is people have to believe you're telling them
the truth, good or right, right, right, good or bad.
They have to believe you're being straight with them.
Speaker 1 (09:20):
This is the CEOs you should know. Ken Ricky is
a Cleveland native, also aviation entrepreneur. All right, let's get
to Bill Clinton. So how did you become his personal pilot?
Speaker 4 (09:30):
So in as I was developing Corporal Wings, a company
we talked about earlier, I got into a specialty niche
of flying rock tours.
Speaker 2 (09:38):
Concert tours.
Speaker 4 (09:39):
Okay, I did Bruce Springsteen and Barbara Streisan, Elton John.
Speaker 3 (09:42):
Tell me you did Motley Crue, Bryan Adams. That's cool, yeah, yeah, yeah.
Speaker 4 (09:49):
But but but these these these tours run two three months,
they run through a season. They're a little longer now,
but at that time, they were two three months, and
you typically got like double or triple the pay because
you were you didn't have to work the rest of
the year.
Speaker 2 (10:02):
But so you charged extra for a short term gig.
Speaker 4 (10:05):
And I get a call from a guy that says,
have you ever done a political campaign? And I said, no,
but how long is it for? Because how long I
am getting price for it? Right? He said, well, for
it's for thirteen months. And I said, thirteen months. What's
the guy running for He said, well, he's running for president.
He said, well, who is it? He said, it's the
governor of Arkansas. And the governor of Arkansas is not
going to need a plane for thirteen months. This guy
has no chance of becoming president.
Speaker 3 (10:27):
The same thing.
Speaker 4 (10:28):
Yeah, And I ended up flying him through the inauguration,
no kidding, So because you know, after they're elected and
before they're inaugurated, and they still use private aircraft.
Speaker 3 (10:37):
So give me give me.
Speaker 1 (10:38):
A Bill Clinton story or a personal experience with him
that I don't know resonated with so.
Speaker 4 (10:44):
So, one of my first meetings with him, after one
on one, he's the he's the governor, he's the governor,
and we go to it. We go to a little
hamburger joint. This is the first time I've met him,
and of course it takes him. He it takes them
ten minutes to get through the bar. There's four people there,
but he has to talk each one of my fo
and we finally sit down and the waitress comes right
over and says, what would you like? And he said,
(11:04):
I'm going to have a burger with your sweet potato fries.
And I said, I'll have the same and he looks
over at me.
Speaker 2 (11:09):
I said nothing to the man.
Speaker 4 (11:10):
And he looks at me, and he says, I'm way
too fat and my cholesterol is too high, but I
just love them sweet potatoes.
Speaker 3 (11:18):
Which is what you would expect somebody from Arkansas.
Speaker 2 (11:21):
To say exactly.
Speaker 4 (11:22):
And years later I not years later, months later I
got to know him better and thought I could start
to ask him because we became friends, right, And I
said to him, I remind him of this conversation, and
he said, you know, if you want to ingratiate yourself
to someone, start with something that's wrong with you. When
you tell someone I'm way too short and I eat
(11:42):
too much, people think you trust them because you're sharing
a fault. And so if you want people to kind
of ingrace, if ingratiate yourself to someone, tell him, tell
him one of your faults. And it's so contrary to
how we think today. Right, we live in a social
media world. Will we tell you only the good stuff
about our right? So think about the fact that we
might artificially be putting up barriers to having better relationships
(12:05):
just by telling people what's.
Speaker 3 (12:06):
Wrong with that? Yeah, No, that's that's great. Insight. That's
that's great advice.
Speaker 1 (12:10):
Give me a rock star story, give me I mean,
there was there any anybody who left again a certain
impression on you from all the rock stars.
Speaker 3 (12:19):
You flew around.
Speaker 2 (12:20):
Well, I would tell you that.
Speaker 4 (12:21):
You know, the misperception about celebrities is that that I
always say my celebrity. God is fair, because if God
made somebody to be a phenomenal singer and then made
them unbelievably intelligent, that would be an unfair God. Right,
And so most of these people are really really good
(12:42):
at their craft, but they're not very broad, okay, I mean,
like you get. And by the way, they practice a
hell of a lot more than you think. When I
would watch Bruce Ringsteen, you he does that concert. You know,
he's known for his four hour concerts. Right, what people
don't know he'll rehearse three hours before a four hour
concert that their sound checks will run hours. That's correct, Okay,
(13:05):
Michael Jackson was unbelievably. It was unbelievably myopology focused on details.
In fact, today in our company, one of our fundamental principles.
Of course, we have people lives in our hands, right,
we're flying. But our fundamental principles, fanatical attention to detail.
And I think I learned that by watching these rock
stars who were so good, but they come up there
(13:27):
and they look so natural, right, but you'd be amazed
at how much time they spend getting there.
Speaker 3 (13:34):
What is the future of flight in your mind?
Speaker 2 (13:38):
Well, I think.
Speaker 4 (13:40):
There's actually you know, we've kind of bifurcated flight, right,
We've really gone into two directions. We have almost two
economies in flight. We have the airline economy, which has
one experience to it, and we have a private experience.
And one of the reasons that the private experience is
growing is because of the degradation of the airline experience.
(14:01):
And the one thing I hear from our clients very
often is that I'm now spending a disproportional amount of
my income. I'm flying privately because that's an experiential thing
and it saves me time, it saves me stress.
Speaker 2 (14:15):
And so when you.
Speaker 4 (14:16):
Ask about the future of flight, I almost have to
answer the question in two vernaculars. One is are we
talking about the private side of flight or are we
talking about the commercialization of flight?
Speaker 3 (14:26):
Right?
Speaker 2 (14:27):
So, I think I think we're down these paths.
Speaker 4 (14:29):
I think of anything COVID solidified the fact that we're
not going to take commercialized flight and bring it back
to the fifties where it's romantic and we get we
get a beautiful place to have a beautiful dinner on
a long flight and there's an actress sitting next to
us that we can romance. I think those days are gone,
and so we're going to get more commercial, more efficient
in terms of how we do it right, automatic check
(14:51):
in facial recognition will speed up the whole process of
getting onto a plane efficiently. So I think facial recognition
is being it's actually tried in over there's many overseas
stops today where you go through TSA through racial recognition, right,
So that's what's coming and that'll make commercial flying more
palatable because the lines will be simpler and so on.
The private flying is is it's just a different economy,
(15:15):
you know, it's a and that economy is growing in
a big way because we're going through a huge transfer
of wealth right now. There is a huge amount of
the baby boomers and the post World War two who
kept a phenomenal amount.
Speaker 2 (15:29):
Of wealth that they kept quiet.
Speaker 4 (15:31):
You know, there was there was there was the unrecognizable rich,
and now that wealth is being transferred, and this is
why today our client is almost ten years younger than
it was pre Codd.
Speaker 3 (15:43):
All right, I'm going to end on this one.
Speaker 1 (15:46):
When somebody meets you, what do you hope they walk
away thinking about Ken Ricky, That.
Speaker 4 (15:55):
I'm passionate about what I do and that I'm compassionate
about how I do it.
Speaker 3 (16:00):
I got that feeling. M M. This is CEOs you
should know, and you just heard Ken Ricky
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