WEBVTT

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For thirty five years, Cindy Stumpo
has been a female home builder with a

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passion for design, a mastery of
detail, and a commitment to her crack.

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With daughter Samantha Stumpo by her side, I don't need my whole family

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on a date with me. That's
a good note. It's goddemn weird.

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See. Stumpo Development is the only
second generation female construction company in the country.

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You're crazy, You're a wacko,
You're insane. I mean, it

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just doesn't end together. Cindy and
Samantha welcome guests to explore the world of

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construction, real estate, development,
design and more. Here unpredictable. Every

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time I think I know what you
want, you switch it out. But

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that's what makes your houses all your
day. Discuss anything that happens between the

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roof and the foundation. Nothing is
off limits. You truly do care about

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everybody checking yell and chikeets green.
But when you get her alone, she's

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the best person on the planet.
Cindy Stumpo is tough as nails and welcome

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to Cindy Stuppo Toughest Nails on WBZ
News Radio ten thirty and I've got a

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few special guests in my studio tonight, the incredible Chat and we have your

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name? Yeah, go ahead,
Angelina. She's new there, she's new.

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We're going to teach her how to
do this. We teach her how

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to co host. So can you
introduce yourself? Angelina? Did you have

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a last name? Yes? I
do. It's going to be Okay,

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that's going to be my future ex
daughter in law. Okay. And who

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else do we have in the studio, Paul English? Paul? What are

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we here to talk about today?
Because I love you so much, but

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we're going to talk about in Boston, a little bit of mental health,

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a little bit of a little bit
of kayak. Let's okay. So,

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like we said before, it's kind
of cool that we have like panic attacks

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now and by Pola, like this
is like the cool thing to be like

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a screwed up person and mentally screwed
up. Yeah, I walk around pick

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attacks. But and then you have
you suffered from bipolar and some panic attacks

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along the way, and ganetic by
the way, right now, proven that

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i'd just put to you right family
members yep, my grandmother and my aunt

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both also severely backpolar okay, and
on a scale of one to ten on

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your success rate. Can we give
you a ten? That'd be nice.

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Okay, you deserve that you I
know you out of ten. So with

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that being said, can you have
problems in your life that you can still

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make it big healthy if you want
to? You can. I think it

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needs a few things. You need
someone to believe in you, Okay,

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and ideally that's your parent or could
be a brother, sister, or not

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an uncle, but someone to believe
in you, who believes in you.

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I was in a family of nine
in a three bedroom house, so we

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didn't get tons of one on one
time with our parents. It's a little

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hot. They're very, very busy. But I had some mentors over my

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life. I actually had some great
aunts and uncles that I absolutely adored and

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spent time with them and enjoyed them, and they I just enjoyed being a

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little kid one of seven and getting
like individual attention from my aunts and uncles.

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I thought that was like the greatest
thing growing up because they didn't have

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a lot of kids. They didn't
the aunts and uncles I'm thinking about did

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not have kids, so they had
the time to give to you. Yeah,

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so you grew up that typical West
Roxbury family with it was like so

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many kids in one house? Yeah, that was I grew up in Perham

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Street and the end of Perham Street
at the intersection. The Boston Little Board

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a story many years ago about this
particular intersection because the four houses in the

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corner had and I'm not kidding you, ten kids, twelve kids, twelve

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kids, fourteen kids, four houses
all in the same intersection. Is that

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crazy? And that's actually insane.
You never hear that anymore today, No,

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never, because the parents be normal, having the rich, never lonely

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in those sometimes. Yeah, did
you like growing up with all those kids?

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And no, I did. I
love my siblings. I'm still incredibly

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close to them. Every Tuesday night
since two thousand and eight, since November

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two thousand and eight, every Tuesday
night I cooked dinner for my siblings.

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You do, yeah, and a
leather bound journal, and I write down

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in at what I cooked, Who
shut up? And what we talked about?

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Why. My parents both passed away
about twenty years ago, and I

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took it upon myself just to put
a lot of attention into my siblings and

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supporting each other after the death of
my parents and staying close to them.

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My siblings are all very close to
my kids. I have two kids,

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Nicole and Michael, and we had
dinner one night at my house. It

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turned out to be an election night
two thousand and eight, Obama's first win,

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and I invited people over for dinner
to watch the election, and we

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had such a good time with my
siblings. I think there were six of

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us that night. That next week, one of my sisters, my sister

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Barbera, said an email saying,
let's do that again next Tuesday, and

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just became a tradition we did every
Tuesday night I have had next to our

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neighbor, Nicholas, passed away last
year at age ninety six, but he

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came to my dinners every year for
I think he came for about ten years.

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What happens when you're the most successful
sibling, most successful you know in

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some ways maybe right, but don't
think I'm we'll get to the point financially.

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Yeah. My siblings have never asked
me for anything, and they keep

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me honest because they know the good, the bad, and the ugly.

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They've seen it all. So nobody
asks you for anything. So when you're

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not asked, you my siblings don't
ask a lot of people ask me for

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stuff. I'll open up my iPhone
here and show you to eat my email.

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Right now, I get asked every
day, but not my best friends

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and not my siblings. So when
nobody I have this thing, you don't

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ask me? Is when I want
to give same? Ask me. I

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don't want to give same. Right. So, but exactly when you start

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taking advantage of my generosity, I'll
go the other way. Yeah, same,

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because that appreciate it exactly coming from
the other virgo, right, I

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know all about it. Yeah,
so you'll be chased until that person doesn't

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like gets expected. Yeah, but
virgos, we keep doing. As cancers,

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we keep doing to we know.
We don't know boundaries, right,

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it's hard to put our foot down. We try, we lift it right

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up. So, okay, now
we know Paul's personal background of everything.

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Talk to me. Tell me how
how Kayak came about, how you sold

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it, how you built that company. Let's go what made you successful?

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Yeah, Kayik was my third company, the one that's been the most successful

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to date. I've done. Now, I've sold six companies in a row,

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some six for six at the moment, six for six. Yeah,

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Kayak. I started in two thousand
and four with a guy named Steve Hafner.

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Steve was one of the founders of
Orbits, and he had the original

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idea for Kayak. And his idea
was seventy percent of the people would come

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to Orbits, would search for flight, find the flight they want, then

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they would leave Orbits, go direct
the airline and book it. So Orbits

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made no money. And he'said,
what if we built a search engine where

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you can't buy anything on Kayak.
We literally just show you every flight,

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every hotel and then when you find
the hotel you wanted, a flight you

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want, it's five places you can
buy, click the link. We'll send

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you directly to jet Blue. And
jet Blue pays us a small commission.

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So that was the original idea.
We had an internal tagline search with us,

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book with them. We are marketing, said, search one and done.

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Because we searched every site, you
didn't need to go to ten travel

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sits anymore. Everything is on Kayak. And it was an incredibly fun ten

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years of my life with lots of
ups and downs and parties and just it

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was a great, great ten years
of my life. And you howled I

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was forty when I saw at Kayak. Okay, so forty was your third

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company? You started at forty years
old, you'd already had three under your

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belt that you sold obviously, Yeah, I guess under my belt. Yeah,

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two underr belt. This was the
third. Okay, now you start

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to see money? How many years
into that company? We started growing rapidly

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in year two? So year two
and three we knew we were going to

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make it. We had about five
companies try to buy us. Give me

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a year two and three? Are
you like going backwards out the duo?

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Like, yes, smellan as you're
leaving that office. Well, it was

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on paper, it was all in
stock, and we didn't cash out until

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we went public in twenty twelve,
and then we sold in thirteen what you

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sold, right, you can google
it. It's so I sold it for

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two billion. So your your shares
alone, my shares alone were one hundred

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and forty million. Yeah, and
you went public? Yeah, and then

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you cashed out? Then did you
stay on as the I left actually pretty

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click quickly after selling it because I'm
not really a big company person, so

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you're not, and I wanted to
start something again. So they make you

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stay on for a certain period.
Day I stayed on as one year as

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a consultant, and I put my
replacement in place, a brilliant, brilliant

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guy who's still there today. And
I'm still a friend to the company.

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My co found of Steve is still
there. He lived. He and I

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hang out in Miami all the time
where he lives, and I still care

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deeply about the company. I want
to help them. But you literally left

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snapping your suspendeds yone. Okay,
this is a home run. Ten years

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had a lot of fun. Obviously, you're a travel age, You're you're

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the travel whatever. So you're going, you're experiencing, you're doing and along

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the way, making money the second
year into the and then boom, hundred

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forty million out the door. We
go. Here we go. Let's go

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hold that thought, because that's only
that's which people problem. By the way,

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hold that thought. This is Cidey
Stumble WBZ News Radio ten thirty will

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be what that sponsored by Flora Decor, National Lumber and Village. Back the

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show stream and welcome back to Tombs
Nails on WBC News Radio ten thirty And

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I'm Cindy Stumpo and I'm here with
Chad Stumpo. Angelina and Paul English.

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What a group? Huh m?
This is the fourthument that been Senny what?

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I don't know. There used to
be three sem beats a full house.

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But okay, whatever, that's that? What are we had talking about?

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We can talk about whatever you want. We can talk about Boston.

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We can talk about Kayak mental health, nonprofit, We could talk about anything.

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That's what good about you? Andy? Right? We could talk about

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everything and anything. We're right,
But I have a question, Paul,

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what inspired you to pursue technology and
entrepreneurship? I would say, you know,

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as a little kid, I was
really into the cars. Not to

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hold you. Do you know what
if my son pronounces is ours? Yeah

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differently? Right? Yeah? I
grew down so you pronounced I just know

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that. Go ahead. Yeah.
My speech dysfunction gets worse after drinking.

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I'm pretty good right now. I
loved cars and trucks. I bought my

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first car when I was twelve.
I couldn't drive ecause I didn't have a

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license, but my brother Dan and
I saved up money from a paper root

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and bought a Ford, a quantoline
van for one hundred dollars. And if

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you asked me, at age fifteen, or sixteen. My aspiration, I

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might have said, to own a
car wash would have been my life goal.

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That's different. I don't know.
I think the thing that got me

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into tech was when I was fifteen
or so, my mom bought a computer

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for the family. It was called
a Commentovic twenty and I read the manual

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and learned how to write code,
and I started developing my own games.

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And that was incredibly, incredibly fun
for me. And then my older brother

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ed. He's I'm number six of
seven. He's the oldest of the seven.

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He is actually a pretty famous programmer. He created the video game Frogger

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on the Atari platform, and I
remember when he was working for Parker Brothers

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working in that game. You didn't
say that your brother does. Hold on?

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Hold on? You self taught yourself
coding. Yeah, that's incredible.

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Just to learn to go to school
for it is hard enough. I have

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friends are in it self taught.
That's incredible. Yeah. It was a

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lot of fun. I really I
liked it. My high school years were

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cars, girls, sports, music, and computers like all of that.

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So I put the computer in there. Yeah. I liked the I liked

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designing games, and I liked because
I was a musician. I also designed

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sound hold on He's sixty. Computers
were very very new to us generation.

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They would use big things that look
like big TVs from nineteen fifty two.

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Okay, good, But I loved
programming. I loved doing music. I

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ended up going to mass Boston and
I studied music and computers, and I

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got my master's degree. My master's
thesis was I built a music synthesized so

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I wrote all the code for it
and designed it. So that took both

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my music education and my computer education. But then I was incredibly inspired my

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brother and seeing how well he was
doing his game Frogger. He sold four

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million copies in one year the first
year it was, so I was thinking

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there might be something in this computer
stuff here. So I by that time

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I was self taught programmer, just
starting as a freshman UMass. But I

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knew how to code, and I
found an internship and I ended up working

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almost full time for the five years
it took me to get my bachel's degree

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as a programmer for different types of
companies. I worked for the US Air

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Force, I worked for medical technology
company, a gaming company, accounting company,

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and I just had a blast.
I love designing things. I love

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designing products. That's awesome. That's
an incredible way to get started. And

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so would you major in US?
Where'd you say? God? Yeah,

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I went to UMAs Boston and I
studied music and computers give you designs?

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And then right after that, just
where'd you start off? After my graduation,

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I worked for a software company in
Cambridge called interly if they built publishing

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software. I worked for them for
six years. Started as a programer,

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I ended up running engineering and then
my last of the area in marketing,

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which is kind of a whole nother
crazy show, because I all, yes,

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that was my training and most it
was self trade. Yeah, self

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taught, and by that time I
did take course in college, but I

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started my career of self taught.
But then I was going to school at

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night at your mass So I learned
a lot. Let me ask you an

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honest question, did you really get
that much out of going to school or

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did you really figure this out on
your own? I'll tell you the main

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thing. I had one really good
professor, guy named Bob Morris, that

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I learned things from him about imaging
and graphic and design, which helped me

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in my career. The main thing
I learned at your Mass which completely changed

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my worldview is your Mass is I
think the third most diverse school in the

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country, most diverse school in New
England, and I had students from like

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every country. It was crazy.
They actually gave me an honorary doctorate a

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few years ago, and at graduation, the chancellor told me that the kids

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graduating that year spoke sixty one native
languages as a primary language. Sixty one

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different languages. I couldn't even name
sixty one languages. So it's a very

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diverse school. And I like that
opened my eyes to traveling, and I

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since it become an addicted travel I'm
traveling at least over really out of That's

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what I got to your Mass is
appreciation for the cultures and a hunger to

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travel. You guys, you both
always feel the need for speed. Huh,

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that's part of it. Yeah,
okay. And then Chad, you

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had another question you wanted to ask, Paul, how did your education influence

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your approach to business? I think
it was. I loved that I could

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work as a programmer and go to
school at the same time, kind of

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balancing both of those things, and
it taught me early on that you can

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do more than one thing at a
time. And I was taking you know,

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liberal arts courses, history courses,
but working during the day. And

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what did you say, wait,
hold on, won't you say liberal lots

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to me? Begin it is like
just another four years of high school.

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That's how I see liberal lots.
Right, Let's just go to high school

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for four more years. Because you're
not gearing into anything. No, it's

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not. It's definitely not aiming you
towards a career maybe Starbucks at best,

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okay, and coming out with a
lot of debt. Could you have done

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what you've done self? Like,
I've self taught my whole weight, right,

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So it was like I went to
some great college, right, I

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did go to Wetworth. But I
guess what I would say is I've been

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the same without going programing, and
I left. I probably would have done

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okay without college. But what I
did need and benefited from greatly is having

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some unbelievable mentors at work. So
I was self taught as a programmer,

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got my first job as a programmer
at age eighteen, and then worked with

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some unbelievable people and would study their
code and how they design things and how

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they wrote code, and how they
tested code and how they made code run

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fast. And I learned and by
working. Yeah that is my producer opening

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up my cocine right now. If
you're hearing that right that I shouldn't be

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drinking, go ahead. Well,
so I learned from great mentors along the

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way. And that was really the
beginning of my career was the working,

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not the school. Okay, got
it. I still say, no matter

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what you did, you were going
to be successful because I think you had

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that drive and you know where it
stemmed from, delivery newspapers when you're a

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little kid. Yeah. The things
that we don't do anymore, the things

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that parents don't make their kids do
it anymore. Right, I knock on

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doors, ask people for money.
Yeah, all the things. Now,

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we'd be afraid for our kids to
go knock on somebody to do it because

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they might pull them in and hurt
them and kill them and put them in

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the basement of kids snow anymore.
Yeah, that's a big mistake too.

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But that's the whole key. See, that's our generation. We wanted to

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make money eighteen. You didn't have
to throw us out of the house we

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were leaving. We wanted to go
like we're eighteen, We're out of We're

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going like I wanted to get out. Even I had the greatest parents of

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the world, had a beautiful home, no one bothered me. I wanted

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to be independent. I wanted to
make money. That's tell a funny story.

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I used to work at a pharmacy
and that I'm called Meddi mart.

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I don't know if they existed anymore. I was a waitress and my father's

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nightclub whacking it out like literally,
which the nightclub Maxwell's in Copley, Oh

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my god, amazing. Yep.
So okay, So just to show what

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a workaholic. My dad was a
workaholic, and I think I was got

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the work ethic from him. But
one night I ate but the other clubs,

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like I could have been working at
nine Leans Down. No, he

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stuck me in Maxwell's a little bit
more of a mature group of Yeah,

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yeah, go ahead. So just
to show you like the work ethic that

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my father, that I modeled after
my father, one night I kind of

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over imbibed. I think it was
on a Friday night. I was probably

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sixteen or seventeen, and I woke
up Saturday with which themost unbelievable, worst

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hangover in the world. And I
called the pharmacist who was the manager,

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and I said, there's no way
I can make it in today. And

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he said, do a little drinking
last night. I said, yeah,

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maybe a little. He said,
come in, I'll fix you up.

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And I couldn't drive. I still
was like, just not feeling well from

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the night. I took a taxi
to work. I'm making two dollars and

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thirty five cents an hour and I
called the taxi to bring me to work.

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My father was like, what are
you doing. My father was always

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worried about spending money and saving money. But I took a taxi to work

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and the farmers. I still don't
know to this day what he gave me.

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He gave me something. He said, you cannot tell people what I

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gave you because I'll lose my license. Gave you. I wish I knew

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what he gave me, because it
fixed that hangover immediately. And I think

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a ten hour shift that thought.
I'm Citty Stumple. You listen a Toughest

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00:19:37.160 --> 00:19:41.480
Hills on wc News Radio ten thirty
will be right back, sponsored by Pillow

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00:19:41.519 --> 00:20:00.160
Windows of Boston. Next day Molding
and Kennedy Carr and welcome back. It's

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00:20:00.160 --> 00:20:03.480
a top of Nails. I'm Setty
Stampo on WBZ News Radio ten thirty and

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00:20:03.519 --> 00:20:11.799
I'm here in the studio with Angelina
and the Star Child, Chad Custochia and

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00:20:11.880 --> 00:20:15.039
the famous Who are you pointing out? You? Paul and Gush? I

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00:20:15.119 --> 00:20:18.240
love you? Okay, Angele,
you had a question, Yes, Paul,

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can you share memorable moments or milestones
from Kayak's growth? Yeah? Boy,

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it was such a fun ten years
of my life. One of my

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favorite moments was I was flying to
New York. We actually Kayak was born

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in Connecticut and Boston. The engineers
well in Boston, and our marketing team

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was in Connecticut and New York.
So I go to New York a but

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once a week. And on the
plane next to me there was a woman

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who had her laptop open and she
was running Kayak. And this is we

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were a year old. It's like
no one knew who Kayak was, no

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00:20:52.960 --> 00:20:56.079
one's using it, and I was
sitting next to our watching her use it,

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and I'm like, this is very
cool. I think that maybe people

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are going to find out about this
because in the first year it was just

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me begging my high school friends,
my brothers and sisters, can you please

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try using this product and give me
feedback. But once it started taking off

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on its own, that was exciting. When I found other people using it

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another milestone that was also really cool. At one point I forgot what year

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this was. But if you went
to google dot com homepage and you just

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typed the letter K and you pause
for a second, the first word that

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would come up, it was kayak. And that was when we were already

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we were growing very very rapidly.
But I'm like, the day we owned

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a letter that was cool, Like
we're the most popular K word on on

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Google. That was fun. And
then there's all these financial milestones. We

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we took a public two hundred employees, three hundred million in revenue, that's

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a million and a half for employee. It was. It was an incredibly

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fun ride, a lot of good
milestones along the way. Wow. So

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it's when you first saw somebody using
your app that was the most exciting thing

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to me. I couldn't stand that. Yeah, I couldn't stand that because

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you're not okay, wow, they're
really were we on a plane with something

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you were? I was on a
plane. She was sitting next to me

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using Kayak was very very cool,
and that was the first time you saw

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somebody that wasn't family friends on there. I told her, I said,

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what do you think of that,
psy Kayak And she said, oh,

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it's this great news site. I
said, I'm the founder, and she

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didn't believe me. She thought I
was hitting on her. Now, question,

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what was that feeling you had inside
when you saw that? It was

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amazing? Then I started wondering,
I wonder if anyone else in this plane

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is ever heard of Kayak, because
it was very very early on in the

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history where no one knew about us
yet. So the next thing you know,

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he's going to the bathroom in the
front of the plane, in the

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back of the way looking at people. Hey, hey, hey, you

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00:22:34.599 --> 00:22:40.319
might want to try and hate.
That's pretty cool. And then take us

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from I have a question, because
you're in your second year, and I

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00:22:45.240 --> 00:22:51.279
know we've touched upon this, we
touched upon the sale when you sold your

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stock. Now you realize you're exactly
how old now forty? I was in

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my forties when we sold it in
two thousand and thirteen. Different paths.

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00:23:04.440 --> 00:23:10.279
I think I just turned just turned
fifty and we sold it for two billion.

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00:23:10.319 --> 00:23:14.039
Yeah, it started at forty and
at fifty. Did you say I'm

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set for life? No, this
is funny. So when we were negotiating

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the sale of the company, let
me rephrase that. Did you take ten

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00:23:22.240 --> 00:23:26.119
minutes to enjoy the high of it? What I did during the negotiation of

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the sale is I calculated how much
money my assistant was going to make.

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I didn't know how much money I
was going to make. I knew it

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was a lot, but I really
she told me she wanted to buy a

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house, and I'm thinking, like, I got to sell this enough that

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she can buy a house. And
I knew how much my programmers would make.

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I knew much my assistant made,
and we had. There were two

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hundred employees. Over half of them
became millionaires that day. And that was

353
00:23:49.079 --> 00:23:52.359
just pump you that you're not worried
about your own pocket, you're worried about

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what your assistant. Well, no, and I'll tell you, you know,

355
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to a point we were talking about
off here earlier. Literally the next

356
00:24:00.400 --> 00:24:04.000
the Boston Globe put me in the
front of the globe that day, and

357
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literally the next morning I started having
panic attacks because here I suddenly had all

358
00:24:08.599 --> 00:24:11.680
this money. I grew up with
no money and I didn't know what to

359
00:24:11.680 --> 00:24:15.279
do with it. I was afraid
of it, and I felt like I

360
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didn't deserve this money. I want
to give the money away. Well that's

361
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why I asked you if you ever
had impost syndrome. Yeah I did.

362
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I did. I asked you that
off here. Yeah, now I'm asking

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now that you're saying that. Yes. So a lot of people don't understand

364
00:24:27.400 --> 00:24:33.079
what imposta syndrome means. They think
that it means you're trying to be somebody

365
00:24:33.160 --> 00:24:36.960
you're not like I'm going to be
you when I'm really Cindy. Okay,

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00:24:37.000 --> 00:24:40.519
that's not what impost syndrome is.
You know what imposta syndrome is, right,

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Yeah, it's basically thinking I'm going
to walk into the office Monday morning,

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there's going to be someone there like
arresting me, say you shouldn't be

369
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here, like you don't deserve this. That's how you That's how your analogy

370
00:24:51.480 --> 00:24:55.880
of it and my analogy of it
is when you have impostera syndrome is you

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don't believe like you've created this company, never earned it, that I've earned

372
00:25:00.680 --> 00:25:04.079
that. It's your wealth and it's
your brain and some people, A lot

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of people go through it. A
lot of my clients have gone through it,

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and I don't think I've ever had
that. I just don't ever give

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myself that five minutes to say,
you know that a girl every you know

376
00:25:15.000 --> 00:25:18.839
like you don't. I celebrated the
success of the team. People were very

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00:25:18.960 --> 00:25:22.839
very happy. It's exciting, you
know, most out of shales. A

378
00:25:22.920 --> 00:25:26.599
lot of people's lives that day,
we did and it was very nice.

379
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Many many years later, I was
at a party after I had left Kayak

380
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and I rented to someone who used
to work there in the early years,

381
00:25:34.240 --> 00:25:38.640
and she said, I just have
to let you know that. I mean,

382
00:25:38.680 --> 00:25:42.039
she was exaggerating, but she said, due to you, I paid

383
00:25:42.039 --> 00:25:45.519
off my house and sent my kids
to college, and I paid for all

384
00:25:45.559 --> 00:25:48.799
of that with Kayak stock. I
thought that was pretty cool. It was

385
00:25:48.839 --> 00:25:52.720
cool that she said it to me. When you started that company, did

386
00:25:52.720 --> 00:25:56.400
you think that you'd end up where
you ended up with that one company if

387
00:25:56.440 --> 00:26:00.119
you get the other companies. No, So I'm again. I'm a programmer

388
00:26:00.200 --> 00:26:04.680
by training and my career is designing
software, running design teams. And when

389
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I ran into Steve Haffner, and
he said he wanted to create a travel

390
00:26:07.880 --> 00:26:11.519
company. I went home that night
and spent some time on Expedia, which

391
00:26:11.519 --> 00:26:14.759
is the number one travel site back
then in two thousand and four, and

392
00:26:14.839 --> 00:26:18.880
I remember thinking, this site is
like epileptic seizure inducing. There's so much

393
00:26:18.880 --> 00:26:22.680
stuff happening, ads popping up everywhere, and I'm thinking I can design something

394
00:26:22.680 --> 00:26:26.200
better than this. I wasn't thinking
financially, but I was thinking, I

395
00:26:26.319 --> 00:26:30.359
know I can build a team.
They can build a better process. Deforment,

396
00:26:30.480 --> 00:26:33.920
Why would you ever have imposted to
ine that you knew, you knew

397
00:26:34.279 --> 00:26:41.279
the money intimidating The money intimidated me. The money. Yeah, we we

398
00:26:41.359 --> 00:26:45.680
never thought of ourselves as not having
money. But I never encountered a rich

399
00:26:45.720 --> 00:26:55.119
person ever until post college. Everyone
around me was blue collars fury. Yeah.

400
00:26:55.359 --> 00:26:59.680
So the concert we were right next
to Newton, we were. Yeah,

401
00:27:00.839 --> 00:27:02.920
you spend any time in Newton.
I don't think we were allowed in

402
00:27:02.960 --> 00:27:07.839
there. You're right on Newton's cote
tails, right, we were. And

403
00:27:07.880 --> 00:27:11.519
you guys never went to like Losy
Andison in Brookline that you didn't cross two

404
00:27:11.519 --> 00:27:15.079
towns. I've skated at Lassi Anderson. Okay, yeah, but keep going.

405
00:27:15.119 --> 00:27:18.000
So I'm just wanting to show the
money with the money was intimidating.

406
00:27:18.079 --> 00:27:23.519
And I went to a friend of
mine, Michael White, and I knew

407
00:27:23.559 --> 00:27:26.680
he had an uncle was a builder. Do you know Tom? Do you

408
00:27:26.720 --> 00:27:33.039
know White Construction company? JF.
White Construction. So Michael's uncle Thomas J.

409
00:27:33.160 --> 00:27:37.400
White, He's now passed away.
He was the founder of Jfhy Construction

410
00:27:37.519 --> 00:27:42.000
Company. And when I sold Kayak, he was eighty at the time,

411
00:27:42.440 --> 00:27:45.960
and I knew he had given a
bunch of his money away. So I

412
00:27:45.000 --> 00:27:48.240
had all this money. I was
afraid of it. I want to give

413
00:27:48.279 --> 00:27:52.559
it away. So I met with
this guy Tom White, and I said,

414
00:27:52.559 --> 00:27:55.039
I made all this money, I
want to give it away. Who

415
00:27:55.039 --> 00:27:59.039
should I give it to? And
he said, go to Haiti and meet

416
00:27:59.079 --> 00:28:02.480
my friend Paul Farmer, and then
go to a homeless shelter. Meet my

417
00:28:02.480 --> 00:28:04.720
friend who runs a homeless shelter in
Boston. Anyway, it's now twenty years

418
00:28:04.799 --> 00:28:08.920
later, and you look where I've
given all my money away. I paid

419
00:28:08.960 --> 00:28:12.039
the tuition for ten thousand kids a
year in Haiti. I have forty schools

420
00:28:12.079 --> 00:28:15.279
and three hundred and fifty teachers,
and I now do a lot of it

421
00:28:15.400 --> 00:28:18.759
to give all your money away most
of it. You gave most of that

422
00:28:18.799 --> 00:28:22.680
away for half. Yeah, oh, you would have had to give half

423
00:28:22.680 --> 00:28:27.000
to the government anyways. Well yeah
maybe right, like, okay, so

424
00:28:27.039 --> 00:28:30.440
if we can break it down some
numbers, but you still give half of

425
00:28:30.519 --> 00:28:33.359
the weight over half, yeah,
and then you stay played the tax on

426
00:28:33.400 --> 00:28:36.519
the other half. But then I
started making more money after that too,

427
00:28:36.799 --> 00:28:41.440
because I sold a few more companies
after kayak, Okay, you're very you're

428
00:28:41.559 --> 00:28:45.559
okay, hold on atlease, get
this straight. You sell one hundred and

429
00:28:45.640 --> 00:28:48.200
forty million in stock, you give
half that money away, right, not

430
00:28:48.279 --> 00:28:52.079
immediately, but over time and time. Yeah, but money was making money,

431
00:28:52.160 --> 00:28:56.480
yeah exactly. But I'm investments are
doing well. Investments are doing well.

432
00:28:56.480 --> 00:29:02.640
But that was what year I sold
the company in twenty thirteen. Well,

433
00:29:02.720 --> 00:29:04.119
in twenty thirteen, we weren't making
very much money on an interest,

434
00:29:04.119 --> 00:29:07.279
so let's call that what it was, right, and then you had to

435
00:29:07.319 --> 00:29:11.079
go into CDs and whatever my markets
were in paying we're making a most might

436
00:29:11.160 --> 00:29:15.960
today and we've made in twenty years. This has been unbelievable, unbelievable correct

437
00:29:15.000 --> 00:29:19.519
sowe stock market and between you know, money market funds and everything else.

438
00:29:19.599 --> 00:29:23.880
But okay, so then you go
and open up more companies and then you

439
00:29:23.960 --> 00:29:32.119
make more money. Yeah, and
gave way more money and gave okay,

440
00:29:32.160 --> 00:29:36.319
and he likes to go and they're
going to find like a waiter waitress that

441
00:29:36.400 --> 00:29:38.319
gets like a ten thousand dollars tip. That's the things he likes to do,

442
00:29:38.400 --> 00:29:42.200
like things about nature. So he's
a very generous man. Right,

443
00:29:44.079 --> 00:29:47.039
So you just keep making money to
keep giving it away, right, It's

444
00:29:47.119 --> 00:29:49.200
incredibly fun to give away money.
We talked about that earlier in the other

445
00:29:49.240 --> 00:29:52.759
segment right that we had a few
months ago. But he does. He

446
00:29:52.880 --> 00:29:53.880
likes to give away money all day. I thought we're going to break.

447
00:29:53.920 --> 00:29:57.119
I'm sitting stumbling. He listen to
WBC News Radio ten thirty and We'll be

448
00:29:57.160 --> 00:30:02.279
right back, sponsored by new Brook
Realty, Boston, would Smaller Insurance,

449
00:30:02.480 --> 00:30:19.440
World Auto Body and Tasca Drive Auto
Body Company and welcome back to Toughest Nails

450
00:30:19.440 --> 00:30:23.680
on WBC News Radio ten thirty.
And I'm Cindy and I'm here with Angelina,

451
00:30:25.279 --> 00:30:29.240
Chad and Paul. Okay. I
think Angelina, I wanted to ask

452
00:30:29.279 --> 00:30:33.279
you a question. Yes, I
would love to know what advice would you

453
00:30:33.319 --> 00:30:37.440
give aspiring young entrepreneurs. I think
the main thing is if you look at

454
00:30:37.720 --> 00:30:42.519
all the jobs you could get,
like maybe work for big tech company like

455
00:30:42.559 --> 00:30:48.119
Google, or work for a little
startup or a medical company or finance company.

456
00:30:48.599 --> 00:30:52.759
Go interview at two or three or
four or five companies, and each

457
00:30:52.759 --> 00:30:56.039
time you interviewed a company, try
to figure out you might meet five or

458
00:30:56.079 --> 00:30:59.279
six people who are the two or
three during that interview that you actually would

459
00:30:59.359 --> 00:31:02.720
end up spending your days with.
And across let's see you do with five

460
00:31:02.759 --> 00:31:07.559
companies. Across those five companies,
which one has a stronger three percent team?

461
00:31:07.079 --> 00:31:12.000
Because early in your career what's really
important is acceleration of skills. You

462
00:31:12.039 --> 00:31:17.079
want to learn as fast as possibly
can. So whatever company has a stronger

463
00:31:17.119 --> 00:31:22.119
team, you'll learn faster and you'll
develop faster. Okay, So I always

464
00:31:22.160 --> 00:31:27.440
stay out on the job sites.
My delivery can really stink at times,

465
00:31:27.519 --> 00:31:33.519
right, like really like pointed,
but my intent is always one thousand percent

466
00:31:33.440 --> 00:31:36.920
and that's because it's a hard courre. What I do is hardcore out there,

467
00:31:37.000 --> 00:31:40.200
right, Like you're literally running hundreds
of guys all day long, with

468
00:31:40.319 --> 00:31:44.440
hundreds of different personalities. So we're
in two different, completely different industries.

469
00:31:44.759 --> 00:31:48.519
You get to work with smotty pants
and I get to work with we don't

470
00:31:48.519 --> 00:31:52.640
eve have high school degrees. Of
high school degrees, I have to go

471
00:31:52.759 --> 00:31:56.200
push the brew me to make somebody
understand what's the push to brew me?

472
00:31:56.279 --> 00:32:00.480
They still don't understand, right,
But we're in two different businesses. So

473
00:32:00.559 --> 00:32:08.240
I'm always pushing Kids that don't have
the intellect, that don't are not good

474
00:32:08.240 --> 00:32:12.359
students. Right, I was a
terrible student. I guess I could have

475
00:32:12.359 --> 00:32:15.440
been a great student. I just
really wasn't into school except the social aspect,

476
00:32:15.559 --> 00:32:19.519
right, getting dressed here and makeup, looking good and going to school

477
00:32:19.519 --> 00:32:22.119
that was fun to me. Social
was fun. Sitting in the classroom watching

478
00:32:22.119 --> 00:32:24.759
fifteen minutes of o'clock go, I
was like, oh god, a nightmare

479
00:32:24.799 --> 00:32:28.400
for me. Nightmare, total nightmare. And then you call on me.

480
00:32:28.440 --> 00:32:30.200
My legs would start swinging and I'd
be like, oh god, where they

481
00:32:30.279 --> 00:32:34.160
leave off on the paragraph because I
wasn't paying attention. And then you know,

482
00:32:34.160 --> 00:32:37.200
the teacher always pays attention to the
kid that's not paying attention, right,

483
00:32:37.279 --> 00:32:39.039
the kid raised the hand. They
don't call the they call and Cindy

484
00:32:40.119 --> 00:32:45.240
what. So I pushed a skilled
you know, the skill because we have

485
00:32:45.279 --> 00:32:47.480
a massive skilled gap out there for
kids. We need plumbers, electricians,

486
00:32:47.599 --> 00:32:52.240
hvac guys. And I heard mister
wonderful say something last week on the news,

487
00:32:52.240 --> 00:32:55.359
and we all know who mister wonderful
is, right from Shark NK and

488
00:32:55.440 --> 00:32:59.720
his advice four or five years ago
was for kids to get into this this

489
00:32:59.720 --> 00:33:07.200
this now. His advice is get
into the skilled labor, get into editing,

490
00:33:07.440 --> 00:33:10.400
engineering of editing, and content creator. Not being a content creator,

491
00:33:10.759 --> 00:33:15.200
but get like I need footage all
the time to put out for content.

492
00:33:15.119 --> 00:33:21.119
And that's where he's pushing and for
you, for kids that know how to

493
00:33:21.240 --> 00:33:25.519
understand and do this, you're pushing
that industry of hou. It's not necessarily

494
00:33:25.640 --> 00:33:30.559
tech. I mean, tech is
a great industry to work in. Healthcare

495
00:33:30.720 --> 00:33:34.200
is a good industry. There's a
lot of incredibly rewarding things you can do

496
00:33:34.240 --> 00:33:37.839
if you're part if you work for
pharmaceutical and you this generation you want to

497
00:33:37.839 --> 00:33:39.240
start up. Money is the way
they want to make money tomorrow. They

498
00:33:39.279 --> 00:33:42.559
don't want to wait ten years and
fifteen years. You understand that, right.

499
00:33:42.640 --> 00:33:45.359
I'll tell you one thing, rest
span of a fleet, I tell

500
00:33:45.599 --> 00:33:47.920
one thing. Really scared, I
just read about this generation they interviewed twelve

501
00:33:49.000 --> 00:33:51.240
year olds in China and twelve year
olds in the US. They said,

502
00:33:51.240 --> 00:33:54.079
what's your career aspiration? And China
number one care aspiration we want to be

503
00:33:54.119 --> 00:33:59.319
an astronaut. In the US twelve
year old number one core aspiration, I

504
00:33:59.359 --> 00:34:04.839
want to be in famous TikTok,
famous influencer. Influencer. That's scary.

505
00:34:04.920 --> 00:34:09.760
Yeah, it's very scary, very
scary, because one percent might make it.

506
00:34:09.880 --> 00:34:15.440
Yeah, one percent. So what
is that telling you look at?

507
00:34:15.880 --> 00:34:20.159
I think my grandmother said the best. She died eight years ago at ninety

508
00:34:20.199 --> 00:34:22.760
eight years old, and she had
all her faculties together at ninety seven,

509
00:34:23.440 --> 00:34:28.599
and she'd see my kids the last
like five years, always on their phones,

510
00:34:28.639 --> 00:34:31.280
and she'd say, that's going to
be very very smart. Three PhDs

511
00:34:31.960 --> 00:34:36.039
when women didn't go to college back
then, and she'd say, sinning,

512
00:34:36.159 --> 00:34:39.280
that's going to be the demise of
your children if you if you don't control

513
00:34:39.360 --> 00:34:44.599
some of that, you know,
pop up. Because she noticed every baby,

514
00:34:45.199 --> 00:34:46.159
you know, she was ninety five
at that time, and everybody off

515
00:34:46.199 --> 00:34:52.599
for dinner and look at their phones. So isn't it crazy how technology can

516
00:34:52.719 --> 00:34:55.400
work in such a great way,
But if you take advantage of it.

517
00:34:55.400 --> 00:34:59.159
It can hurt you in other ways. You look, now, Paul,

518
00:34:59.199 --> 00:35:01.880
come on, we go for dinner
with eight people and seven people are on

519
00:35:01.920 --> 00:35:07.239
their phones. Well, why are
we all together? Then my son started

520
00:35:07.320 --> 00:35:10.000
this when he come back from school
on school vacations and say, okay,

521
00:35:10.039 --> 00:35:13.760
we'll all go for dinner. But
everybody put your phone in the middle of

522
00:35:13.800 --> 00:35:17.039
table. And the first person that
picks up their phone, the first person

523
00:35:17.079 --> 00:35:20.960
I picks up their phone, he'd
say, you're going to pay the bill.

524
00:35:21.360 --> 00:35:23.000
So what I do for my Tuesday
night dinner is I bring for fourteen

525
00:35:23.079 --> 00:35:27.480
years of my siblings. First one
to touch the phone does the dishes?

526
00:35:27.679 --> 00:35:34.280
Ye okay, yeah, So everybody
says a but we're all addicted, right

527
00:35:34.800 --> 00:35:37.760
right. So but I've got clients
texting me all day, all night.

528
00:35:37.840 --> 00:35:40.920
I got to get back to them. And every time they text me,

529
00:35:40.920 --> 00:35:44.840
it's like life or death, right, there's always nine to one one in

530
00:35:44.840 --> 00:35:47.880
my business. There's a snowstorm coming, there's a blizzard coming, there's whatever,

531
00:35:49.000 --> 00:35:52.639
right, And then I do get
the beautiful texts that say, hey,

532
00:35:52.679 --> 00:35:54.039
Sinny, just want to say thank
you for a beautiful home. But

533
00:35:54.079 --> 00:35:58.159
those are far and few and in
between, right, like you get that.

534
00:35:58.920 --> 00:36:01.280
I will say something really quick.
Advice to young people say thank you,

535
00:36:01.639 --> 00:36:06.119
Yes, say thank you. Tell
people you appreciate them. They don't

536
00:36:06.119 --> 00:36:09.719
do that. They are doing write
notes, write letters. I have nephews

537
00:36:09.760 --> 00:36:16.480
that write. I will still do
that. My nephews Matt and Mitchell each

538
00:36:16.679 --> 00:36:22.079
just wrote me a card thanking me
for something question written. Could you read

539
00:36:22.079 --> 00:36:29.199
the writing? I could really because
the block writing, I can read it.

540
00:36:29.199 --> 00:36:34.199
It's it's look. I guess the
greatest thing about your brain is you

541
00:36:34.320 --> 00:36:37.760
kept that brain young in technology.
So you did an age. So when

542
00:36:37.800 --> 00:36:39.320
you said to me you were sixty, I'm like, you show you're sixty.

543
00:36:39.440 --> 00:36:44.679
Like, so you've kept that brain
if you was young because of technology.

544
00:36:45.480 --> 00:36:47.320
And I think I've kept my brain
young being out there in construction,

545
00:36:47.559 --> 00:36:51.199
boots on the ground. And I
never want to change that. Like I

546
00:36:51.239 --> 00:36:53.599
don't want to sit in an office
and no, I'd rather be on job

547
00:36:53.639 --> 00:36:59.519
sites and ranton and raven and doing
what I do. But it's people like

548
00:36:59.559 --> 00:37:01.920
you and I can make a difference. We're just in two different worlds and

549
00:37:02.039 --> 00:37:07.119
businesses. Your I'm virgo, you're
cancer cancer. Yeah, right, so

550
00:37:07.159 --> 00:37:12.280
we want to help everybody. Okay, so we know you know, we

551
00:37:12.360 --> 00:37:15.760
know about the dating app that you
could come out. Will you stop at

552
00:37:15.760 --> 00:37:20.320
that one? Absolutely not? I
think if I had to, let's say

553
00:37:20.320 --> 00:37:22.960
there was no way to make money
in tech. Let's say there were no

554
00:37:22.039 --> 00:37:29.800
tech companies and I had to work
at Starbucks or whatever to be an Uber

555
00:37:29.880 --> 00:37:31.840
driver. I actually am an Uber
driver. What do you mean? You're

556
00:37:31.840 --> 00:37:36.039
an Uber driver? I'm Uber driver. Get out. I'll show you my

557
00:37:36.119 --> 00:37:39.039
rading. What are you talking about? Driver? Watch this all right?

558
00:37:39.119 --> 00:37:44.360
I feel like a horrible human vingnam
you should? What do you mean watch

559
00:37:44.480 --> 00:37:51.119
us? What's my rating? Four
point ninety six? Wait minute, my

560
00:37:51.239 --> 00:37:53.119
driver rating? Where's the other rating? I don't even know how to use

561
00:37:53.159 --> 00:38:00.559
this thing? Drivers rating? This
is the driver app? Almost five four

562
00:38:00.639 --> 00:38:05.760
point nine six. Let's I don't
do it. Let me get this,

563
00:38:05.920 --> 00:38:08.239
okay, you just you just get
in your car and you pick people up

564
00:38:08.280 --> 00:38:12.039
in Uber. Yeah, my girl. I'll say to my girlfriend, do

565
00:38:12.079 --> 00:38:14.480
you man if I drive Ober for
an hour? So she's like, sure,

566
00:38:14.519 --> 00:38:16.719
I don't mind that you find strangers
more interesting than me. The next

567
00:38:16.880 --> 00:38:23.800
hour, I thinks found the new
man the most amazing. I gotta understand

568
00:38:23.880 --> 00:38:28.719
this, So you'll just get out
of your car. A multi millionaire guy,

569
00:38:29.039 --> 00:38:34.599
right, millions, and you just
drive some strangers around and they have

570
00:38:34.679 --> 00:38:37.480
no idea who you are, and
you have no idea who they are.

571
00:38:38.039 --> 00:38:43.920
Just to get to what keep your
feet on the beat. It's basically all

572
00:38:44.039 --> 00:38:49.360
of us should do acts of service
in different ways. And let me drive

573
00:38:49.480 --> 00:38:52.000
someone to a medical appointment. It's
a very minor thing. Can you do

574
00:38:52.119 --> 00:38:55.079
it? Like in the safe eeries? Oh sorry, can you run for

575
00:38:55.159 --> 00:39:00.559
president? I think you made this
roll a freaking country one. I want

576
00:39:00.599 --> 00:39:02.719
to hang out with him more.
I'm already feel like a better I want

577
00:39:02.760 --> 00:39:06.639
to do better. Already, hold
on a second. He makes you wanted

578
00:39:06.639 --> 00:39:09.880
to do. So you'll say to
your your fiance, I want to go

579
00:39:09.960 --> 00:39:13.559
out and just drive anoover for a
couple hours, no problem, And she'll

580
00:39:13.599 --> 00:39:15.719
be like, sure, you want
to go hang out with strangers and not

581
00:39:15.880 --> 00:39:17.280
me. Do you ever do public
speaking events? No? But I'm going

582
00:39:17.360 --> 00:39:22.119
to get him on chatter. Yeah, because you're going to understand what chatter

583
00:39:22.239 --> 00:39:25.840
is because you can make it so
many people listen to you that by talking

584
00:39:25.920 --> 00:39:30.239
to these people on it's like it's
like a clubhouse, but it's much more

585
00:39:30.280 --> 00:39:36.400
advanced and even blows by xpaces cool
and I'll just stick your rooms with me.

586
00:39:37.239 --> 00:39:39.880
And but now you just really blew
my mind. So I feel like

587
00:39:39.920 --> 00:39:43.519
this is the movie. Now there's
the TV shows are coming out with maybe

588
00:39:43.719 --> 00:39:45.280
it should be a TV show,
it should be a Lifetime original. So

589
00:39:45.400 --> 00:39:51.079
you'll just get in and start driving
a room. And do you ever get

590
00:39:51.119 --> 00:39:55.559
kogo people? And you can't.
I've had only two really bad rides.

591
00:39:55.639 --> 00:40:00.039
When was that drug deal gone bad? No? And the other one was

592
00:40:00.719 --> 00:40:05.199
I drove these two guys and I'm
dropping them off at a club and I

593
00:40:05.239 --> 00:40:07.920
said, how do you like Boston? They go, It's great, but

594
00:40:07.159 --> 00:40:10.639
all the women are bitches? And
I said all the women and they go,

595
00:40:10.800 --> 00:40:14.239
yeah, you know, if it's
all the women, that might not

596
00:40:14.400 --> 00:40:19.800
be the problem. I don't think
they give me five stars. I were

597
00:40:19.840 --> 00:40:22.760
going to break. This is Citdny
Stumple. You listen Toughest Nails on WBZ

598
00:40:22.920 --> 00:40:43.480
News Radio ten thirty. He'll be
right back and welcome back to Toughest Nails

599
00:40:43.519 --> 00:40:50.920
on WBZ News Radio ten thirty.
I'm here with Angelina, Chad by Paul.

600
00:40:51.599 --> 00:40:53.320
Everyone knows by now, I would
think after seven years on radio,

601
00:40:53.320 --> 00:40:58.280
I'm Sidney Stumbo. Okay, talk
to me. We all know able the

602
00:40:58.320 --> 00:41:01.519
dating app that is out and running
right now go. The app is called

603
00:41:01.599 --> 00:41:06.639
LOLA. It stands for Love Language
l O l A dot com and we're

604
00:41:06.719 --> 00:41:10.199
the best dating app in Boston.
Just launch in Boston and then how do

605
00:41:10.280 --> 00:41:15.119
they find it again? LOLA dot
com l O l A l O l

606
00:41:15.239 --> 00:41:20.320
A dot com. That's right,
join, get on there, start dating.

607
00:41:21.280 --> 00:41:22.480
Everybody. Have a great, safe
weekend, and we'll see you next

608
00:41:22.519 --> 00:41:28.880
weekend. This is Cindy Stumbo Toughest
Nails on WBZ Radio News ten thirty

