Tech Mogul & Activist, Paul English

Episode Transcript

Speaker 1 (00:00):
For thirty five years, Cindy Stumpo has been a female
home builder with a passion for design, a mastery of detail,
and a commitment to her crack. With daughter Samantha Stumpo
by her side, I don't need my.

Speaker 2 (00:10):
Whole family on a date with me. That's a good note.

Speaker 3 (00:12):
It's goddemn weird.

Speaker 2 (00:13):
See.

Speaker 1 (00:13):
Stumpo Development is the only second generation female construction company
in the country.

Speaker 4 (00:18):
You're crazy, You're a wacko.

Speaker 5 (00:19):
You're insane.

Speaker 6 (00:22):
I mean, it just doesn't end together.

Speaker 1 (00:23):
Cindy and Samantha welcome guests to explore the world of construction,
real estate, development, design and more.

Speaker 7 (00:30):
Here unpredictable. Every time I think I know what you want,
you switch it out. But that's what makes your houses
all your day.

Speaker 1 (00:35):
Discuss anything that happens between the roof and the foundation.
Nothing is off limits. You truly do care about everybody
checking yell and chikeets green. But when you get her alone,
she's the best person on the planet. Cindy Stumpo is
tough as nails.

Speaker 2 (00:51):
And welcome to Cindy Stuppo Toughest Nails on WBZ News
Radio ten thirty and I've got a few special guests
in my studio tonight, the incredible Chat and we have
your name? Yeah, go ahead, Angelina. She's new there, she's new.
We're going to teach her how to do this. We
teach her how to co host. So can you introduce yourself?

Speaker 3 (01:11):
Angelina?

Speaker 2 (01:12):
Did you have a last name? Yes? I do. It's
going to be Okay, that's going to be my future
ex daughter in law. Okay. And who else do we
have in the studio, Paul English? Paul? What are we
here to talk about today? Because I love you so much,
but we're going to talk.

Speaker 7 (01:32):
About in Boston, a little bit of mental health.

Speaker 2 (01:36):
A little bit of a little bit of kayak. Let's okay. So,
like we said before, it's kind of cool that we
have like panic attacks now and by Pola, like this
is like the cool thing to be like a screwed
up person and mentally screwed up. Yeah, I walk around
pick attacks. But and then you have you suffered from
bipolar and some panic attacks along the way, and ganetic

(01:58):
by the way, right now, proven that i'd just put
to you right family members.

Speaker 7 (02:03):
Yep, my grandmother and my aunt both also severely backpolar.

Speaker 2 (02:07):
Okay, and on a scale of one to ten on
your success rate. Can we give you a ten?

Speaker 7 (02:13):
That'd be nice.

Speaker 2 (02:14):
Okay, you deserve that you I know you out of ten.
So with that being said, can you have problems in
your life that you can still make it big healthy
if you want to?

Speaker 7 (02:25):
You can. I think it needs a few things. You
need someone to believe in you, Okay, and ideally that's
your parent or could be a brother, sister, or not
an uncle, but someone to believe in you, who believes
in you. I was in a family of nine in
a three bedroom house, so we didn't get tons of
one on one time with our parents.

Speaker 2 (02:44):
It's a little hot.

Speaker 7 (02:45):
They're very, very busy. But I had some mentors over
my life. I actually had some great aunts and uncles
that I absolutely adored and spent time with them and
enjoyed them, and they I just enjoyed being a little
kid one of seven and getting like individual attention from
my aunts and uncles. I thought that was like the
greatest thing.

Speaker 2 (03:04):
Growing up because they didn't have a lot of kids.

Speaker 7 (03:06):
They didn't the aunts and uncles I'm thinking about did
not have.

Speaker 2 (03:08):
Kids, so they had the time to give to you. Yeah,
so you grew up that typical West Roxbury family with
it was like so many kids in one house?

Speaker 7 (03:16):
Yeah, that was I grew up in Perham Street and
the end of Perham Street at the intersection. The Boston
Little Board a story many years ago about this particular
intersection because the four houses in the corner had and
I'm not kidding you, ten kids, twelve kids, twelve kids,
fourteen kids, four houses all in the same intersection.

Speaker 2 (03:33):
Is that crazy?

Speaker 7 (03:33):
And that's actually insane. You never hear that anymore today.

Speaker 2 (03:37):
No, never, because the parents be normal, having the rich,
never lonely in those sometimes. Yeah, did you like growing
up with all those kids?

Speaker 7 (03:46):
And no, I did. I love my siblings. I'm still
incredibly close to them. Every Tuesday night since two thousand
and eight, since November two thousand and eight, every Tuesday
night I cooked dinner for my siblings. You do, yeah,
and a leather bound journal, and I write down in
at what I cooked, Who shut up? And what we
talked about?

Speaker 2 (04:04):
Why.

Speaker 7 (04:06):
My parents both passed away about twenty years ago, and
I took it upon myself just to put a lot
of attention into my siblings and supporting each other after
the death of my parents and staying close to them.
My siblings are all very close to my kids. I
have two kids, Nicole and Michael, and we had dinner

(04:26):
one night at my house. It turned out to be
an election night two thousand and eight, Obama's first win,
and I invited people over for dinner to watch the election,
and we had such a good time with my siblings.
I think there were six of us that night. That
next week, one of my sisters, my sister Barbera, said
an email saying, let's do that again next Tuesday, and
just became a tradition we did every Tuesday night I
have had next to our neighbor, Nicholas, passed away last

(04:48):
year at age ninety six, but he came to my
dinners every year for I think he came for about
ten years.

Speaker 2 (04:54):
What happens when you're the most successful.

Speaker 7 (04:56):
Sibling, most successful you know in some ways maybe right,
but don't think I'm.

Speaker 2 (05:00):
We'll get to the point financially.

Speaker 7 (05:03):
Yeah. My siblings have never asked me for anything, and
they keep me honest because they know the good, the bad,
and the ugly. They've seen it all.

Speaker 2 (05:14):
So nobody asks you for anything.

Speaker 7 (05:15):
So when you're not asked, you my siblings don't ask
a lot of people ask me for stuff. I'll open
up my iPhone here and show you to eat my email.
Right now, I get asked every day, but not my
best friends and not my siblings.

Speaker 2 (05:30):
So when nobody I have this thing, you don't ask me?
Is when I want to give same? Ask me. I
don't want to give same. Right. So, but exactly when
you start taking advantage of my generosity, I'll go the
other way. Yeah, same, because that appreciate it exactly coming
from the other.

Speaker 4 (05:49):
Virgo, right, I know all about it.

Speaker 2 (05:52):
Yeah, so you'll be chased until that person doesn't like
gets expected.

Speaker 5 (05:57):
Yeah, but virgos, we keep doing.

Speaker 2 (06:00):
As cancers, we keep doing to we know. We don't
know boundaries, right.

Speaker 5 (06:03):
It's hard to put our foot down. We try, we
lift it right up.

Speaker 2 (06:07):
So, okay, now we know Paul's personal background of everything.
Talk to me. Tell me how how Kayak came about,
how you sold it, how you built that company. Let's
go what made you successful?

Speaker 7 (06:20):
Yeah, Kayik was my third company, the one that's been
the most successful to date. I've done. Now, I've sold
six companies in a row, some six for six at
the moment.

Speaker 2 (06:30):
Six for six.

Speaker 7 (06:30):
Yeah, Kayak. I started in two thousand and four with
a guy named Steve Hafner. Steve was one of the
founders of Orbits, and he had the original idea for Kayak.
And his idea was seventy percent of the people would
come to Orbits, would search for flight, find the flight
they want, then they would leave Orbits, go direct the
airline and book it. So Orbits made no money. And he'said,
what if we built a search engine where you can't

(06:51):
buy anything on Kayak. We literally just show you every flight,
every hotel and then when you find the hotel you wanted,
a flight you want, it's five places you can buy,
click the link. We'll send you directly to jet Blue.
And jet Blue pays us a small commission. So that
was the original idea. We had an internal tagline search
with us, book with them. We are marketing, said, search
one and done. Because we searched every site, you didn't

(07:12):
need to go to ten travel sits anymore. Everything is
on Kayak. And it was an incredibly fun ten years
of my life with lots of ups and downs and
parties and just it was a great, great ten years
of my life. And you howled I was forty when
I saw at Kayak.

Speaker 2 (07:28):
Okay, so forty was your third company? You started at
forty years old, you'd already had three under your belt
that you sold.

Speaker 7 (07:34):
Obviously, Yeah, I guess under my belt.

Speaker 2 (07:37):
Yeah, two underr belt. This was the third. Okay, now
you start to see money? How many years into that company?

Speaker 7 (07:44):
We started growing rapidly in year two? So year two
and three we knew we were going to make it.
We had about five companies try to buy us.

Speaker 2 (07:53):
Give me a year two and three? Are you like
going backwards out the duo? Like, yes, smellan as you're
leaving that office.

Speaker 7 (07:59):
Well, it was on paper, it was all in stock,
and we didn't cash out until we went public in
twenty twelve. And then we sold in twenty thirteen.

Speaker 2 (08:08):
What you sold, right, you can google it.

Speaker 7 (08:10):
It's so I sold it for two billion.

Speaker 2 (08:12):
So your your shares alone.

Speaker 7 (08:14):
My shares alone were one hundred and forty million.

Speaker 2 (08:17):
Yeah, and you went public? Yeah, and then you cashed out?
Then did you stay on as the.

Speaker 7 (08:24):
I left actually pretty click quickly after selling it because
I'm not really a big company person, so you're not,
and I wanted to start something again.

Speaker 2 (08:32):
So they make you stay on for a certain period day.

Speaker 7 (08:35):
I stayed on as one year as a consultant, and
I put my replacement in place, a brilliant, brilliant guy
who's still there today. And I'm still a friend to
the company. My co found of Steve is still there.
He lived, He and I hang out in Miami all
the time where he lives, and I still care deeply
about the company. I want to help them.

Speaker 2 (08:54):
But you literally left snapping your suspendeds yone. Okay, this
is a home run ten years, had a lot of fun. Obviously,
you're a travel age, You're you're the travel whatever. So
you're going, you're experiencing, you're doing and along the way,
making money. The second year into the and then boom,
hundred forty million out the door.

Speaker 4 (09:11):
We go.

Speaker 2 (09:11):
Here we go. Let's go hold that thought, because that's
only that's which people problem. By the way, hold that thought.
This is Cidey Stumble WBZ News Radio ten thirty will
be what.

Speaker 6 (09:19):
That sponsored by Flora Decor, National Lumber and Village.

Speaker 1 (09:23):
Back the.

Speaker 2 (09:32):
Show stream and welcome back to Tombs Nails on WBC
News Radio ten thirty And I'm Cindy Stumpo and I'm
here with.

Speaker 5 (09:48):
Chad Stumpo, Angelina.

Speaker 7 (09:50):
And Paul English.

Speaker 2 (09:51):
What a group?

Speaker 7 (09:52):
Huh m?

Speaker 2 (09:53):
This is the fourthument that been Senny what. I don't know.
There used to be three sem beats a full house.
But okay, whatever, that's that. What are we had talking about?

Speaker 7 (10:03):
We can talk about whatever you want. We can talk
about Boston, we can talk about Kayak mental health, nonprofit.

Speaker 2 (10:08):
We could talk about anything. That's what good about you?

Speaker 4 (10:11):
Andy? Right?

Speaker 2 (10:11):
We could talk about everything and anything.

Speaker 5 (10:13):
We're right, But I have a question, Paul, what inspired
you to pursue technology and entrepreneurship?

Speaker 7 (10:21):
I would say, you know, as a little kid, I
was really into the cars.

Speaker 2 (10:26):
Not to hold you. Do you know what if my
son pronounces is ours? Yeah differently? Right? Yeah?

Speaker 5 (10:32):
I grew down so you pronounced I just know that.

Speaker 2 (10:35):
Go ahead.

Speaker 7 (10:36):
Yeah. My speech dysfunction gets worse after drinking. I'm pretty
good right now. I loved cars and trucks. I bought
my first car when I was twelve. I couldn't drive
ecause I didn't have a license, but my brother Dan
and I saved up money from a paper root and
bought a Ford, a quantoline van for one hundred dollars.

(10:57):
And if you asked me at age fifteen or sixteen.
My aspiration, I might have said, to own a car
wash would have been my life goal.

Speaker 3 (11:07):
That's different.

Speaker 7 (11:08):
I don't know. I think the thing that got me
into tech was when I was fifteen or so, my
mom bought a computer for the family. It was called
a Commentovic twenty and I read the manual and learned
how to write code, and I started developing my own games.
And that was incredibly, incredibly fun for me. And then
my older brother ed. He's I'm number six of seven.

(11:30):
He's the oldest of the seven. He is actually a
pretty famous programmer. He created the video game Frogger on
the Atari platform, and I remember when he was working
for Parker Brothers working in that game.

Speaker 2 (11:42):
You didn't say that your brother does.

Speaker 4 (11:44):
Hold on?

Speaker 5 (11:44):
Hold on You self taught yourself coding. Yeah, that's incredible.
Just to learn to go to school for it is
hard enough. I have friends are in it self taught.

Speaker 4 (11:53):
That's incredible.

Speaker 7 (11:54):
Yeah. It was a lot of fun. I really I
liked it. My high school years were cars, girls, sports, music,
and computers like all of that.

Speaker 5 (12:06):
So I put the computer in there.

Speaker 7 (12:08):
Yeah. I liked the I liked designing games, and I
liked because I was a musician.

Speaker 2 (12:13):
I also designed sound hold on He's sixty. Computers were
very very new to us generation. They would use big
things that look like big TVs from nineteen fifty two. Okay, good.

Speaker 7 (12:27):
But I loved programming. I loved doing music. I ended
up going to mass Boston and I studied music and computers,
and I got my master's degree. My master's thesis was
I built a music synthesized so I wrote all the
code for it and designed it. So that took both
my music education and my computer education. But then I
was incredibly inspired my brother and seeing how well he

(12:48):
was doing his game Frogger. He sold four million copies
in one year the first year it was, so I
was thinking there might be something in this computer stuff here.
So I by that time I was self taught programmer,
just starting as a freshman UMass. But I knew how
to code, and I found an internship and I ended
up working almost full time for the five years it

(13:11):
took me to get my bachel's degree as a programmer
for different types of companies. I worked for the US
Air Force, I worked for medical technology company, a gaming company,
accounting company, and I just had a blast. I love
designing things. I love designing products.

Speaker 4 (13:27):
That's awesome. That's an incredible way to get started. And
so would you major in US? Where'd you say? God?

Speaker 7 (13:35):
Yeah, I went to UMAs Boston and I studied music
and computers give you designs?

Speaker 4 (13:40):
And then right after that, just where'd you start off?

Speaker 7 (13:44):
After my graduation, I worked for a software company in
Cambridge called interly if they built publishing software. I worked
for them for six years. Started as a programer. I
ended up running engineering and then my last of the
area in marketing, which is kind of a whole nother
crazy show, because I all, yes, that was my training.

Speaker 2 (14:05):
And most it was self trade.

Speaker 7 (14:06):
Yeah, self taught, and by that time I did take
course in college, but I started my career of self taught.
But then I was going to school at night at
your mass So I learned a lot.

Speaker 2 (14:15):
Let me ask you an honest question, did you really
get that much out of going to school or did
you really figure this out on your own?

Speaker 7 (14:22):
I'll tell you the main thing. I had one really
good professor guy named Bob Morris, that I learned things
from him about imaging and graphic and design, which helped
me in my career. The main thing I learned at
your Mass which completely changed my worldview is your Mass
is I think the third most diverse school in the country,
most diverse school in New England, and I had students

(14:43):
from like every country. It was crazy. They actually gave
me an honorary doctorate a few years ago, and at graduation,
the chancellor told me that the kids graduating that year
spoke sixty one native languages as a primary language, sixty
one different languages. I couldn't even name sixty one languages.
So it's a very diverse school. And I like that

(15:04):
opened my eyes to traveling, and I since it become
an addicted travel I'm traveling.

Speaker 2 (15:09):
At least over really out of That's what I got.

Speaker 7 (15:12):
To your Mass is appreciation for the cultures and a
hunger to travel.

Speaker 2 (15:20):
You guys, you both always feel the need for speed. Huh,
that's part of it. Yeah, okay. And then Chad, you
had another question you wanted to ask, Paul.

Speaker 5 (15:28):
How did your education influence your approach to business?

Speaker 7 (15:33):
I think it was I loved that I could work
as a programmer and go to school at the same time,
kind of balancing both of those things, and it taught
me early on that you can do more than one
thing at a time. And I was taking you know,
liberal arts courses, history courses, but working during the day.

Speaker 2 (15:54):
And what did you say, Wait, hold on, won't you
say liberal lots to me? Begin it is like just
another four years of high school. That's how I see
liberal lots. Right, Let's just go to high school for
four more years. Because you're not gearing into anything.

Speaker 7 (16:06):
No, it's not. It's definitely not aiming you towards a
career maybe Starbucks.

Speaker 2 (16:12):
At best, okay, and coming out with a lot of debt.
Could you have done what you've done self? Like I've
self taught my whole weight, right, So it was like
I went to some great college, right, I did go
to Wetworth.

Speaker 7 (16:27):
But I guess what I would say is I've.

Speaker 2 (16:30):
Been the same without going programing, and I left.

Speaker 7 (16:34):
I probably would have done okay without college. But what
I did need and benefited from greatly is having some
unbelievable mentors at work. So I was self taught as
a programmer, got my first job as a programmer at
age eighteen, and then worked with some unbelievable people and
would study their code and how they design things, and

(16:55):
how they wrote code and how they tested code and
how they made code run fast. And I learned and
by working.

Speaker 2 (17:02):
Yeah that is my producer opening up my cocine right now.
If you're hearing that right that I shouldn't be drinking,
go ahead.

Speaker 7 (17:07):
Well, so I learned from great mentors along the way.
And that was really the beginning of my career was
the working, not the school.

Speaker 2 (17:16):
Okay, got it. I still say, no matter what you did,
you were going to be successful because I think you
had that drive and you know where it stemmed from
delivery newspapers when you're a little kid.

Speaker 7 (17:27):
Yeah.

Speaker 2 (17:27):
The things that we don't do anymore. The things that
parents don't make their kids do it anymore.

Speaker 7 (17:31):
Right, I knock on doors, ask people for money.

Speaker 2 (17:34):
Yeah, all the things. Now, we'd be afraid for our
kids to go knock on somebody to do it because
they might pull them in and hurt them and kill
them and put them in.

Speaker 5 (17:40):
The basement of kids snow anymore.

Speaker 2 (17:43):
Yeah, that's a big mistake too. But that's the whole key. See,
that's our generation. We wanted to make money eighteen. You
didn't have to throw us out of the house. We
were leaving. We wanted to go like we're eighteen, we're
out of We're going like I wanted to get out.
Even I had the greatest parents of the world, had
a beautiful home, no one bothered me. I wanted to
be independent. I wanted to make money.

Speaker 7 (18:05):
That's tell a funny story. I used to work at
a pharmacy in that I'm called Meddi mart. I don't
know if they existed anymore.

Speaker 2 (18:10):
I was a waitress and my father's nightclub whacking it
out like literally, which the nightclub Maxwell's in Copley.

Speaker 7 (18:18):
Oh my god, amazing.

Speaker 2 (18:19):
Yep.

Speaker 7 (18:20):
So okay, So just to show what a workaholic. My
dad was a workaholic, and I think I was got
the work ethic from him. But one night I ate
but the other.

Speaker 2 (18:29):
Clubs, like I could have been working at nine Leans Down. No,
he stuck me in Maxwell's, a little bit more of
a mature group of Yeah, yeah, go ahead.

Speaker 7 (18:35):
So just to show you like the work ethic that
my father, that I modeled after my father, one night
I kind of over imbibed. I think it was on
a Friday night. I was probably sixteen or seventeen, and
I woke up Saturday with which themost unbelievable worst hangover
in the world. And I called the pharmacist who was

(18:56):
the manager, and I said, there's no way I can
make it in today. And he said, do a little
drinking last night. I said, yeah, maybe a little. He said,
come in, I'll fix you up. And I couldn't drive.
I still was like, just not feeling well from the night.
I took a taxi to work. I'm making two dollars
and thirty five cents an hour and I called the
taxi to bring me to work. My father was like,

(19:17):
what are you doing. My father was always worried about
spending money and saving money. But I took a taxi
to work and the farmers. I still don't know to
this day what he gave me. He gave me something.
He said, you cannot tell people what I gave you
because I'll lose my license.

Speaker 4 (19:30):
Gave you.

Speaker 7 (19:30):
I wish I knew what he gave me, because it
fixed that hangover immediately. And I think a ten hour
shift that thought. I'm Citty Stumple. You listen a Toughest
Hills on wc News Radio ten thirty will be right.

Speaker 6 (19:40):
Back, sponsored by Pillow Windows of Boston. Next Day Molding
and Kennedy Carr.

Speaker 2 (19:59):
And welcome back. It's a top of Nails. I'm Setty
Stampo on WBZ News Radio ten thirty and I'm here
in the studio with Angelina and the Star Child, Chad
Custochia and the famous Who.

Speaker 7 (20:13):
Are you pointing out?

Speaker 2 (20:14):
You?

Speaker 7 (20:15):
Paul and Gush?

Speaker 2 (20:15):
I love you? Okay, Angele, you had a question.

Speaker 3 (20:18):
Yes, Paul, can you share memorable moments or milestones from
Kayak's growth?

Speaker 7 (20:23):
Yeah? Boy, it was such a fun ten years of
my life. One of my favorite moments was I was
flying to New York. We actually Kayak was born in
Connecticut and Boston. The engineers well in Boston, and our
marketing team was in Connecticut and New York. So I
go to New York a but once a week. And

(20:45):
on the plane next to me there was a woman
who had her laptop open and she was running Kayak.
And this is we were a year old. It's like
no one knew who Kayak was, no one's using it,
and I was sitting next to our watching her use it,
and I'm like, this is very cool. I think that
maybe people are going to find out about this because
in the first year it was just me begging my
high school friends, my brothers and sisters, can you please
try using this product and give me feedback. But once

(21:07):
it started taking off on its own, that was exciting.
When I found other people using it another milestone that
was also really cool. At one point I forgot what
year this was. But if you went to google dot
com homepage and you just typed the letter K and
you pause for a second, the first word that would
come up, it was kayak. And that was when we
were already we were growing very very rapidly. But I'm like,

(21:28):
the day we owned a letter that was cool, Like
we're the most popular K word on on Google. That
was fun. And then there's all these financial milestones. We
we took a public two hundred employees, three hundred million
in revenue, that's a million and a half for employee.
It was. It was an incredibly fun ride, a lot
of good milestones along the way.

Speaker 3 (21:47):
Wow.

Speaker 2 (21:48):
So it's when you first saw somebody using your app that.

Speaker 7 (21:50):
Was the most exciting thing to me.

Speaker 2 (21:52):
I couldn't stand that. Yeah, I couldn't stand that because
you're not okay, wow, they're really were we on a
plane with something? You were?

Speaker 7 (22:00):
I was on a plane. She was sitting next to
me using Kayak was very very cool.

Speaker 2 (22:04):
And that was the first time you saw somebody that
wasn't family friends on there.

Speaker 7 (22:08):
I told her, I said, what do you think of that,
psy Kayak And she said, oh, it's this great news site.
I said, I'm the founder, and she didn't believe me.
She thought I was hitting on her.

Speaker 5 (22:16):
Now, question, what was that feeling you had inside when
you saw that.

Speaker 7 (22:20):
It was amazing? Then I started wondering, I wonder if
anyone else in this plane is ever heard of Kayak,
because it was very very early on in the history
where no one knew about us yet.

Speaker 5 (22:28):
So the next thing you know, he's going to the
bathroom in the front of the plane, in the back
of the way looking at people.

Speaker 2 (22:34):
Hey, hey, hey, you might want to try and hate.
That's pretty cool. And then take us from I have
a question, because you're in your second year and I
know we've touched upon this, we touched upon the sale
when you sold your stock. Now you realize you're exactly

(22:55):
how old now forty.

Speaker 7 (22:58):
I was in my forties when we sold it in
two thousand and thirteen. Different paths. I think I just
turned just turned fifty and we sold it for two billion.

Speaker 2 (23:10):
Yeah, it started at forty and at fifty, did you
say I'm set for life?

Speaker 7 (23:15):
No, this is funny. So when we were negotiating the
sale of the company.

Speaker 2 (23:21):
Let me rephrase that. Did you take ten minutes to
enjoy the high of it?

Speaker 7 (23:25):
What I did during the negotiation of the sale is
I calculated how much money my assistant was going to make.
I didn't know how much money I was going to make.
I knew it was a lot, but I really she
told me she wanted to buy a house, and I'm thinking, like,
I got to sell this enough that she can buy
a house. And I knew how much my programmers would make.
I knew much my assistant made, and we had There

(23:45):
were two hundred employees. Over half of them became millionaires
that day.

Speaker 2 (23:49):
And that was just pump you that you're not worried
about your own pocket, you're worried about what your assistant.

Speaker 7 (23:54):
Well, no, and I'll tell you, you know, to a
point we were talking about off here earlier. Literally the
next the Boston Globe put me in the front of
the globe that day, and literally the next morning I
started having panic attacks because here, I suddenly had all
this money. I grew up with no money, and I
didn't know what to do with it. I was afraid
of it, and I felt like I didn't deserve this money.

(24:16):
I want to give the money away.

Speaker 2 (24:18):
Well that's why I asked you if you ever had
impost syndrome.

Speaker 7 (24:21):
Yeah I did. I did.

Speaker 2 (24:23):
I asked you that off here.

Speaker 4 (24:24):
Yeah.

Speaker 2 (24:24):
Now I'm asking now that you're saying that.

Speaker 7 (24:26):
Yes.

Speaker 2 (24:26):
So a lot of people don't understand what imposta syndrome means.
They think that it means you're trying to be somebody
you're not, like I'm going to be you when I'm
really Cindy. Okay, that's not what impost syndrome is. You
know what imposta syndrome is, right.

Speaker 7 (24:40):
Yeah, it's basically thinking I'm going to walk into the
office Monday morning, there's going to be someone there like
arresting me, say you shouldn't be here, like you don't
deserve this.

Speaker 2 (24:49):
That's how you that's how your analogy of it and
my analogy of it is when you have impostera syndrome
is you don't believe like you've created this company, never
earned it, that I've earned that it's your wealth and
it's your brain, and some people, a lot of people
go through it. A lot of my clients have gone
through it, and I don't think I've ever had that.

(25:11):
I just don't ever give myself that five minutes to say,
you know that a girl every you know like you don't.

Speaker 7 (25:17):
I celebrated the success of the team. People were very
very happy. It's exciting, you know, most.

Speaker 2 (25:22):
Out of shales A lot of people's lives that.

Speaker 7 (25:25):
Day, we did and it was very nice. Many many
years later, I was at a party after I had
left Kayak and I rented to someone who used to
work there in the early years, and she said, I
just have to let you know that. I mean, she
was exaggerating, but she said, due to you, I paid
off my house and sent my kids to college, and

(25:45):
I paid for all of that with Kayak stock. I
thought that was pretty cool. It was cool that she
said it to me.

Speaker 2 (25:52):
When you started that company, did you think that you'd
end up where you ended up with that one company
if you get the other companies.

Speaker 7 (25:58):
No, So I'm again. I'm a programmer by training, and
my career is designing software, running design teams. And when
I ran into Steve Haffner, and he said he wanted
to create a travel company. I went home that night
and spent some time on Expedia, which is the number
one travel site back then in two thousand and four,
and I remember thinking, this site is like epileptic seizure inducing.
There's so much stuff happening, ads popping up everywhere, and

(26:22):
I'm thinking I can design something better than this. I
wasn't thinking financially, but I was thinking, I know I
can build a team. They can build a better process.

Speaker 2 (26:30):
Deforment, why would you ever have imposted to ine that
you knew, you knew.

Speaker 7 (26:35):
The money intimidating. The money intimidated me.

Speaker 2 (26:38):
The money.

Speaker 7 (26:38):
Yeah, we we never thought of ourselves as not having money.
But I never encountered a rich person ever until post college.
Everyone around me was blue collars fury. Yeah. So the
concert we were right next to Newton, we were. Yeah,

(27:00):
you spend any time in Newton. I don't think we
were allowed in there.

Speaker 2 (27:05):
You're right on Newton's cote tails, right, we were. And
you guys never went to like Losy Andison in Brookline
that you didn't cross two towns.

Speaker 7 (27:11):
I've skated at Lassi Anderson.

Speaker 2 (27:13):
Okay, yeah, but keep going. So I'm just wanting to.

Speaker 7 (27:16):
Show the money with the money was intimidating. And I
went to a friend of mine, Michael White, and I
knew he had an uncle was a builder. Do you
know Tom? Do you know White Construction company? JF. White Construction.
So Michael's uncle Thomas J. White, He's now passed away.
He was the founder of Jfhy Construction Company. And when

(27:39):
I sold Kayak, he was eighty at the time, and
I knew he had given a bunch of his money away.
So I had all this money. I was afraid of it.
I want to give it away. So I met with
this guy Tom White, and I said, I made all
this money, I want to give it away. Who should
I give it to? And he said, go to Haiti
and meet my friend Paul Farmer, and then go to

(28:01):
a homeless shelter. Meet my friend who runs a homeless
shelter in Boston. Anyway, it's now twenty years later, and
you look where I've given all my money away. I
paid the tuition for ten thousand kids a year in Haiti.
I have forty schools and three hundred and fifty teachers,
and I now do a lot of give all.

Speaker 2 (28:16):
Your money away most of it. You gave most of
that away for half. Yeah, oh, you would have had
to give half to the government anyways.

Speaker 7 (28:24):
Well yeah maybe right.

Speaker 2 (28:27):
Like, okay, so if we can break it down some numbers,
but you still give half of the weight over half, yeah,
and then you stay played the tax on the other half.

Speaker 7 (28:34):
But then I started making more money after that too,
because I sold a few more companies after.

Speaker 2 (28:38):
Kayak, Okay, you're very you're okay, hold on atlease, get
this straight. You sell one hundred and forty million in stock,
you give half that money away, right.

Speaker 7 (28:49):
Not immediately, but over time and time.

Speaker 2 (28:50):
Yeah, but money was making money.

Speaker 7 (28:53):
Yeah exactly. But I'm investments are doing well.

Speaker 2 (28:56):
Investments are doing well. But that was what year.

Speaker 7 (28:59):
I sold the company in twenty thirteen.

Speaker 2 (29:02):
Well, in twenty thirteen, we weren't making very much money
on an interest, so let's call that what it was, right,
and then you had to go into CDs and whatever
my markets were in paying we're making a most might
today and we've made in twenty years.

Speaker 7 (29:12):
This has been unbelievable, unbelievable.

Speaker 2 (29:15):
Correct sowe stock market and between you know, money market
funds and everything else. But okay, so then you go
and open up more companies and then you make more money.

Speaker 7 (29:25):
Yeah, and gave way more.

Speaker 2 (29:28):
Money and gave okay, and he likes to go and
they're going to find like a waiter waitress that gets
like a ten thousand dollars tip. That's the things he
likes to do, like things about nature. So he's a
very generous man. Right, So you just keep making money
to keep giving it away, right.

Speaker 7 (29:46):
It's incredibly fun to give away money.

Speaker 2 (29:48):
We talked about that earlier in the other segment right
that we had a few months ago. But he does.
He likes to give away money all day. I thought
we're going to break. I'm sitting stumbling. He listen to
WBC News Radio ten thirty and We'll be.

Speaker 6 (29:58):
Right back, sponsored by new Brook Realty, Boston, would Smaller Insurance,
World Auto Body and Tasca Drive Auto Body.

Speaker 2 (30:14):
Company and welcome back to Toughest Nails on WBC News
Radio ten thirty. And I'm Cindy and I'm here.

Speaker 7 (30:23):
With Angelina, Chad and Paul.

Speaker 2 (30:27):
Okay. I think Angelina, I wanted to ask you a question.

Speaker 3 (30:30):
Yes, I would love to know what advice would you
give aspiring young entrepreneurs.

Speaker 7 (30:35):
I think the main thing is if you look at
all the jobs you could get, like maybe work for
big tech company like Google, or work for a little
startup or a medical company or finance company. Go interview
at two or three or four or five companies, and
each time you interviewed a company, try to figure out
you might meet five or six people who are the

(30:57):
two or three during that interview that you actually would
end up spending your days with. And across let's see
you do with five companies. Across those five companies, which
one has a stronger three percent team? Because early in
your career what's really important is acceleration of skills. You
want to learn as fast as possibly can. So whatever
company has a stronger team, you'll learn faster and you'll

(31:19):
develop faster.

Speaker 2 (31:22):
Okay, So I always stay out on the job sites.
My delivery can really stink at times, right, like really
like pointed, but my intent is always one thousand percent
and that's because it's a hard courre. What I do
is hardcore out there, right, Like you're literally running hundreds
of guys all day long, with hundreds of different personalities.
So we're in two different, completely different industries. You get

(31:45):
to work with smotty pants and I get to work
with we.

Speaker 4 (31:48):
Don't eve have high school degrees.

Speaker 2 (31:50):
Of high school degrees, I have to go push the
brew me to make somebody understand what's the push to
brew me? They still don't understand, right, But we're in
two different businesses. So I'm always pushing Kids that don't
have the intellect, that don't are not good students. Right,
I was a terrible student. I guess I could have

(32:12):
been a great student. I just really wasn't into school
except the social aspect, right, getting dressed here and makeup,
looking good and going to school that was fun to me.
Social was fun. Sitting in the classroom watching fifteen minutes
of o'clock.

Speaker 7 (32:24):
Go, I was like, oh god, a nightmare for me.

Speaker 2 (32:26):
Nightmare, total nightmare. And then you call on me. My
legs would start swinging and I'd be like, oh god,
where they leave off on the paragraph because I wasn't
paying attention. And then you know, the teacher always pays
attention to the kid that's not paying attention, right, the
kid raised the hand. They don't call the they call
and Cindy what. So I pushed a skilled you know,
the skill because we have a massive skilled gap out

(32:46):
there for kids. We need plumbers, electricians, hvac guys. And
I heard mister wonderful say something last week on the news,
and we all know who mister wonderful is, right from
Shark NK and his advice four or five years ago
was for kids to get into this this this now.
His advice is get into the skilled labor, get into editing,

(33:07):
engineering of editing, and content creator. Not being a content creator,
but get like I need footage all the time to
put out for content. And that's where he's pushing and
for you, for kids that know how to understand and
do this, you're pushing that industry of hou.

Speaker 7 (33:25):
It's not necessarily tech. I mean, tech is a great
industry to work in. Healthcare is a good industry. There's
a lot of incredibly rewarding things you can do if
you're part if you work for pharmaceutical and you this
generation you want to start up.

Speaker 2 (33:38):
Money is the way they want to make money tomorrow.
They don't want to wait ten years and fifteen years.
You understand that, right. I'll tell you one thing, rest
span of a fleet, I.

Speaker 7 (33:45):
Tell one thing. Really scared, I just read about this
generation they interviewed twelve year olds in China and twelve
year olds in the US. They said, what's your career aspiration?
And China number one care aspiration we want to be
an astronaut. In the US twelve year old number one
core aspiration.

Speaker 2 (33:59):
I want to be in famous TikTok, famous influencer. Influencer.

Speaker 7 (34:04):
That's scary.

Speaker 2 (34:04):
Yeah, it's very scary, very scary, because one percent might
make it. Yeah, one percent. So what is that telling
you look at? I think my grandmother said the best.
She died eight years ago at ninety eight years old,
and she had all her faculties together at ninety seven,
and she'd see my kids the last like five years,

(34:27):
always on their phones, and she'd say, that's going to
be very very smart. Three PhDs when women didn't go
to college back then, and she'd say, sinning, that's going
to be the demise of your children if you if
you don't control some of that, you know, pop up.
Because she noticed every baby, you know, she was ninety
five at that time, and everybody off for dinner and

(34:48):
look at their phones. So isn't it crazy how technology
can work in such a great way, But if you
take advantage of it. It can hurt you in other ways.
You look, now, Paul, come on, we go for dinner
with eight people and seven people are on their phones. Well,
why are we all together? Then my son started this
when he come back from school on school vacations and say, okay,

(35:11):
we'll all go for dinner. But everybody put your phone
in the middle of table. And the first person that
picks up their phone, the first person I picks up
their phone, he'd say, you're going to pay the bill.

Speaker 7 (35:21):
So what I do for my Tuesday night dinner is
I bring for fourteen years of my siblings. First one
to touch the phone does the dishes?

Speaker 2 (35:27):
Ye okay, yeah, So everybody says a but we're all addicted,
right right. So but I've got clients texting me all day,
all night. I got to get back to them. And
every time they text me, it's like life or death, right,
there's always nine to one one in my business. There's
a snowstorm coming, there's a blizzard coming, there's whatever, right,

(35:50):
And then I do get the beautiful texts that say, hey, Sinny,
just want to say thank you for a beautiful home.
But those are far and few and in between, right,
like you get that.

Speaker 7 (35:58):
I will say something really quick. Advice to young people
say thank you, Yes, say thank you. Tell people you
appreciate them.

Speaker 2 (36:05):
They don't do that.

Speaker 7 (36:06):
They are doing write notes, write letters. I have nephews
that write.

Speaker 2 (36:14):
I will still do that.

Speaker 7 (36:15):
My nephews Matt and Mitchell each just wrote me a
card thanking me for something question written.

Speaker 2 (36:21):
Could you read the writing? I could really because the.

Speaker 7 (36:25):
Block writing, I can read it.

Speaker 2 (36:29):
It's it's look. I guess the greatest thing about your
brain is you kept that brain young in technology. So
you did an age. So when you said to me
you were sixty, I'm like, you show you're sixty. Like,
so you've kept that brain if you was young because
of technology. And I think I've kept my brain young
being out there in construction, boots on the ground. And

(36:50):
I never want to change that. Like I don't want
to sit in an office and no, I'd rather be
on job sites and ranton and raven and doing what
I do. But it's people like you and I can
make a difference. We're just in two different worlds and businesses.

Speaker 7 (37:04):
Your I'm virgo, you're cancer cancer.

Speaker 2 (37:07):
Yeah, right, so we want to help everybody. Okay, so
we know you know, we know about the dating app
that you could come out. Will you stop at that one?

Speaker 7 (37:16):
Absolutely not? I think if I had to, let's say
there was no way to make money in tech. Let's
say there were no tech companies and I had to
work at Starbucks or whatever to be an Uber driver.
I actually am an Uber driver.

Speaker 2 (37:32):
What do you mean? You're an Uber driver?

Speaker 7 (37:33):
I'm Uber driver? Get OUTI I'll show you my rading.

Speaker 2 (37:36):
What are you talking about?

Speaker 4 (37:38):
Driver?

Speaker 7 (37:39):
Watch this all right?

Speaker 5 (37:40):
I feel like a horrible human vingnam you should?

Speaker 7 (37:42):
What do you mean watch us? What's my rating?

Speaker 2 (37:49):
Four point ninety six?

Speaker 7 (37:50):
Wait minute, my driver rating?

Speaker 2 (37:52):
Where's the other rating? I don't even know how to
use this thing? Drivers rating?

Speaker 7 (37:57):
This is the driver app? Almost five four point nine six.
Let's I don't do it.

Speaker 2 (38:05):
Let me get this, okay, you just you just get
in your car and you pick people up in Uber.

Speaker 7 (38:10):
Yeah, my girl. I'll say to my girlfriend, do you
man if I drive Ober for an hour? So she's like, sure,
I don't mind that you find strangers more interesting than me.

Speaker 5 (38:17):
The next hour, I thinks found the new man.

Speaker 4 (38:22):
The most amazing.

Speaker 2 (38:23):
I gotta understand this, so you'll just get out of
your car a multi millionaire guy, right, millions, and you
just drive some strangers around and they have no idea
who you are, and you have no idea who they are.
Just to get to what keep your feet on the beat.

Speaker 7 (38:41):
It's basically all of us should do acts of service
in different ways. And let me drive someone to a
medical appointment. It's a very minor thing.

Speaker 2 (38:52):
Can you do it? Like in the safe eeries?

Speaker 4 (38:54):
Oh sorry?

Speaker 5 (38:55):
Can you run for president? I think you made this
roll a freaking country one. I want to hang out
with him more. I'm already feel like a better I
want to do better. Already, hold on a second.

Speaker 2 (39:05):
He makes you wanted to do. So you'll say to
your your fiance, I want to go out and just
drive anoover for a couple hours, no problem, And she'll
be like, sure, you want to go hang out with
strangers and not me.

Speaker 4 (39:16):
Do you ever do public speaking events? No?

Speaker 2 (39:17):
But I'm going to get him on chatter. Yeah, because
you're going to understand what chatter is because you can
make it so many people listen to you that by
talking to these people on it's like it's like a clubhouse,
but it's much more advanced and even blows by xpaces
cool and I'll just stick your rooms with me. And

(39:38):
but now you just really blew my mind.

Speaker 5 (39:40):
So I feel like this is the movie. Now there's
the TV shows are coming.

Speaker 2 (39:42):
Out with maybe it should be a TV show, it
should be a Lifetime original. So you'll just get in
and start driving a room. And do you ever getkogle people?
And you can't.

Speaker 7 (39:54):
I've had only two really bad rides. When was that
drug deal gone bad?

Speaker 2 (39:59):
No?

Speaker 7 (40:00):
And the other one was I drove these two guys
and I'm dropping them off at a club and I said,
how do you like Boston? They go, It's great, but
all the women are bitches? And I said all the
women and they go, yeah, you know, if it's all
the women, that might not be the problem. I don't
think they give me five stars.

Speaker 2 (40:19):
I were going to break. This is Citdny Stumple. You
listen Toughest Nails on WBZ News Radio ten thirty. He'll
be right back and welcome back to Toughest Nails on

(40:43):
WBZ News Radio ten thirty. I'm here with Angelina Chad
by Paul. Everyone knows by now, I would think after
seven years on radio, I'm Sidney Stumbo. Okay, talk to me.
We all know able. The dating app that is out
and running right now go.

Speaker 7 (41:01):
The app is called LOLA. It stands for Love Language
l O l A dot com and we're the best
dating app in Boston.

Speaker 2 (41:08):
Just launch in Boston and then how do they find
it again?

Speaker 7 (41:12):
LOLA dot com l O l A l O l
A dot com.

Speaker 2 (41:16):
That's right, join, get on there, start dating. Everybody. Have
a great, safe weekend, and we'll see you next weekend.
This is Cindy Stumbo Toughest Nails on WBZ Radio News
ten thirty