Speaker 1: For thirty five years, Cindy Stumpo has been a female
Speaker 1: home builder with a passion for design, a mastery of detail,
Speaker 1: and a commitment to her crack. With daughter Samantha Stumpo
Speaker 1: by her side, I don't need my.
Speaker 2: Whole family on a date with me. That's a good note.
Speaker 3: It's goddemn weird.
Speaker 2: See.
Speaker 1: Stumpo Development is the only second generation female construction company
Speaker 1: in the country.
Speaker 4: You're crazy, You're a wacko.
Speaker 5: You're insane.
Speaker 6: I mean, it just doesn't end together.
Speaker 1: Cindy and Samantha welcome guests to explore the world of construction,
Speaker 1: real estate, development, design and more.
Speaker 7: Here unpredictable. Every time I think I know what you want,
Speaker 7: you switch it out. But that's what makes your houses
Speaker 7: all your day.
Speaker 1: Discuss anything that happens between the roof and the foundation.
Speaker 1: Nothing is off limits. You truly do care about everybody
Speaker 1: checking yell and chikeets green. But when you get her alone,
Speaker 1: she's the best person on the planet. Cindy Stumpo is
Speaker 1: tough as nails.
Speaker 2: And welcome to Cindy Stuppo Toughest Nails on WBZ News
Speaker 2: Radio ten thirty and I've got a few special guests
Speaker 2: in my studio tonight, the incredible Chat and we have
Speaker 2: your name? Yeah, go ahead, Angelina. She's new there, she's new.
Speaker 2: We're going to teach her how to do this. We
Speaker 2: teach her how to co host. So can you introduce yourself?
Speaker 3: Angelina?
Speaker 2: Did you have a last name? Yes? I do. It's
Speaker 2: going to be Okay, that's going to be my future
Speaker 2: ex daughter in law. Okay. And who else do we
Speaker 2: have in the studio, Paul English? Paul? What are we
Speaker 2: here to talk about today? Because I love you so much,
Speaker 2: but we're going to talk.
Speaker 7: About in Boston, a little bit of mental health.
Speaker 2: A little bit of a little bit of kayak. Let's okay. So,
Speaker 2: like we said before, it's kind of cool that we
Speaker 2: have like panic attacks now and by Pola, like this
Speaker 2: is like the cool thing to be like a screwed
Speaker 2: up person and mentally screwed up. Yeah, I walk around
Speaker 2: pick attacks. But and then you have you suffered from
Speaker 2: bipolar and some panic attacks along the way, and ganetic
Speaker 2: by the way, right now, proven that i'd just put
Speaker 2: to you right family members.
Speaker 7: Yep, my grandmother and my aunt both also severely backpolar.
Speaker 2: Okay, and on a scale of one to ten on
Speaker 2: your success rate. Can we give you a ten?
Speaker 7: That'd be nice.
Speaker 2: Okay, you deserve that you I know you out of ten.
Speaker 2: So with that being said, can you have problems in
Speaker 2: your life that you can still make it big healthy
Speaker 2: if you want to?
Speaker 7: You can. I think it needs a few things. You
Speaker 7: need someone to believe in you, Okay, and ideally that's
Speaker 7: your parent or could be a brother, sister, or not
Speaker 7: an uncle, but someone to believe in you, who believes
Speaker 7: in you. I was in a family of nine in
Speaker 7: a three bedroom house, so we didn't get tons of
Speaker 7: one on one time with our parents.
Speaker 2: It's a little hot.
Speaker 7: They're very, very busy. But I had some mentors over
Speaker 7: my life. I actually had some great aunts and uncles
Speaker 7: that I absolutely adored and spent time with them and
Speaker 7: enjoyed them, and they I just enjoyed being a little
Speaker 7: kid one of seven and getting like individual attention from
Speaker 7: my aunts and uncles. I thought that was like the
Speaker 7: greatest thing.
Speaker 2: Growing up because they didn't have a lot of kids.
Speaker 7: They didn't the aunts and uncles I'm thinking about did
Speaker 7: not have.
Speaker 2: Kids, so they had the time to give to you. Yeah,
Speaker 2: so you grew up that typical West Roxbury family with
Speaker 2: it was like so many kids in one house?
Speaker 7: Yeah, that was I grew up in Perham Street and
Speaker 7: the end of Perham Street at the intersection. The Boston
Speaker 7: Little Board a story many years ago about this particular
Speaker 7: intersection because the four houses in the corner had and
Speaker 7: I'm not kidding you, ten kids, twelve kids, twelve kids,
Speaker 7: fourteen kids, four houses all in the same intersection.
Speaker 2: Is that crazy?
Speaker 7: And that's actually insane. You never hear that anymore today.
Speaker 2: No, never, because the parents be normal, having the rich,
Speaker 2: never lonely in those sometimes. Yeah, did you like growing
Speaker 2: up with all those kids?
Speaker 7: And no, I did. I love my siblings. I'm still
Speaker 7: incredibly close to them. Every Tuesday night since two thousand
Speaker 7: and eight, since November two thousand and eight, every Tuesday
Speaker 7: night I cooked dinner for my siblings. You do, yeah,
Speaker 7: and a leather bound journal, and I write down in
Speaker 7: at what I cooked, Who shut up? And what we
Speaker 7: talked about?
Speaker 2: Why.
Speaker 7: My parents both passed away about twenty years ago, and
Speaker 7: I took it upon myself just to put a lot
Speaker 7: of attention into my siblings and supporting each other after
Speaker 7: the death of my parents and staying close to them.
Speaker 7: My siblings are all very close to my kids. I
Speaker 7: have two kids, Nicole and Michael, and we had dinner
Speaker 7: one night at my house. It turned out to be
Speaker 7: an election night two thousand and eight, Obama's first win,
Speaker 7: and I invited people over for dinner to watch the election,
Speaker 7: and we had such a good time with my siblings.
Speaker 7: I think there were six of us that night. That
Speaker 7: next week, one of my sisters, my sister Barbera, said
Speaker 7: an email saying, let's do that again next Tuesday, and
Speaker 7: just became a tradition we did every Tuesday night I
Speaker 7: have had next to our neighbor, Nicholas, passed away last
Speaker 7: year at age ninety six, but he came to my
Speaker 7: dinners every year for I think he came for about
Speaker 7: ten years.
Speaker 2: What happens when you're the most successful.
Speaker 7: Sibling, most successful you know in some ways maybe right,
Speaker 7: but don't think I'm.
Speaker 2: We'll get to the point financially.
Speaker 7: Yeah. My siblings have never asked me for anything, and
Speaker 7: they keep me honest because they know the good, the bad,
Speaker 7: and the ugly. They've seen it all.
Speaker 2: So nobody asks you for anything.
Speaker 7: So when you're not asked, you my siblings don't ask
Speaker 7: a lot of people ask me for stuff. I'll open
Speaker 7: up my iPhone here and show you to eat my email.
Speaker 7: Right now, I get asked every day, but not my
Speaker 7: best friends and not my siblings.
Speaker 2: So when nobody I have this thing, you don't ask me?
Speaker 2: Is when I want to give same? Ask me. I
Speaker 2: don't want to give same. Right. So, but exactly when
Speaker 2: you start taking advantage of my generosity, I'll go the
Speaker 2: other way. Yeah, same, because that appreciate it exactly coming
Speaker 2: from the other.
Speaker 4: Virgo, right, I know all about it.
Speaker 2: Yeah, so you'll be chased until that person doesn't like
Speaker 2: gets expected.
Speaker 5: Yeah, but virgos, we keep doing.
Speaker 2: As cancers, we keep doing to we know. We don't
Speaker 2: know boundaries, right.
Speaker 5: It's hard to put our foot down. We try, we
Speaker 5: lift it right up.
Speaker 2: So, okay, now we know Paul's personal background of everything.
Speaker 2: Talk to me. Tell me how how Kayak came about,
Speaker 2: how you sold it, how you built that company. Let's
Speaker 2: go what made you successful?
Speaker 7: Yeah, Kayik was my third company, the one that's been
Speaker 7: the most successful to date. I've done. Now, I've sold
Speaker 7: six companies in a row, some six for six at
Speaker 7: the moment.
Speaker 2: Six for six.
Speaker 7: Yeah, Kayak. I started in two thousand and four with
Speaker 7: a guy named Steve Hafner. Steve was one of the
Speaker 7: founders of Orbits, and he had the original idea for Kayak.
Speaker 7: And his idea was seventy percent of the people would
Speaker 7: come to Orbits, would search for flight, find the flight
Speaker 7: they want, then they would leave Orbits, go direct the
Speaker 7: airline and book it. So Orbits made no money. And he'said,
Speaker 7: what if we built a search engine where you can't
Speaker 7: buy anything on Kayak. We literally just show you every flight,
Speaker 7: every hotel and then when you find the hotel you wanted,
Speaker 7: a flight you want, it's five places you can buy,
Speaker 7: click the link. We'll send you directly to jet Blue.
Speaker 7: And jet Blue pays us a small commission. So that
Speaker 7: was the original idea. We had an internal tagline search
Speaker 7: with us, book with them. We are marketing, said, search
Speaker 7: one and done. Because we searched every site, you didn't
Speaker 7: need to go to ten travel sits anymore. Everything is
Speaker 7: on Kayak. And it was an incredibly fun ten years
Speaker 7: of my life with lots of ups and downs and
Speaker 7: parties and just it was a great, great ten years
Speaker 7: of my life. And you howled I was forty when
Speaker 7: I saw at Kayak.
Speaker 2: Okay, so forty was your third company? You started at
Speaker 2: forty years old, you'd already had three under your belt
Speaker 2: that you sold.
Speaker 7: Obviously, Yeah, I guess under my belt.
Speaker 2: Yeah, two underr belt. This was the third. Okay, now
Speaker 2: you start to see money? How many years into that company?
Speaker 7: We started growing rapidly in year two? So year two
Speaker 7: and three we knew we were going to make it.
Speaker 7: We had about five companies try to buy us.
Speaker 2: Give me a year two and three? Are you like
Speaker 2: going backwards out the duo? Like, yes, smellan as you're
Speaker 2: leaving that office.
Speaker 7: Well, it was on paper, it was all in stock,
Speaker 7: and we didn't cash out until we went public in
Speaker 7: twenty twelve. And then we sold in twenty thirteen.
Speaker 2: What you sold, right, you can google it.
Speaker 7: It's so I sold it for two billion.
Speaker 2: So your your shares alone.
Speaker 7: My shares alone were one hundred and forty million.
Speaker 2: Yeah, and you went public? Yeah, and then you cashed out?
Speaker 2: Then did you stay on as the.
Speaker 7: I left actually pretty click quickly after selling it because
Speaker 7: I'm not really a big company person, so you're not,
Speaker 7: and I wanted to start something again.
Speaker 2: So they make you stay on for a certain period day.
Speaker 7: I stayed on as one year as a consultant, and
Speaker 7: I put my replacement in place, a brilliant, brilliant guy
Speaker 7: who's still there today. And I'm still a friend to
Speaker 7: the company. My co found of Steve is still there.
Speaker 7: He lived, He and I hang out in Miami all
Speaker 7: the time where he lives, and I still care deeply
Speaker 7: about the company. I want to help them.
Speaker 2: But you literally left snapping your suspendeds yone. Okay, this
Speaker 2: is a home run ten years, had a lot of fun. Obviously,
Speaker 2: you're a travel age, You're you're the travel whatever. So
Speaker 2: you're going, you're experiencing, you're doing and along the way,
Speaker 2: making money. The second year into the and then boom,
Speaker 2: hundred forty million out the door.
Speaker 4: We go.
Speaker 2: Here we go. Let's go hold that thought, because that's
Speaker 2: only that's which people problem. By the way, hold that thought.
Speaker 2: This is Cidey Stumble WBZ News Radio ten thirty will
Speaker 2: be what.
Speaker 6: That sponsored by Flora Decor, National Lumber and Village.
Speaker 1: Back the.
Speaker 2: Show stream and welcome back to Tombs Nails on WBC
Speaker 2: News Radio ten thirty And I'm Cindy Stumpo and I'm
Speaker 2: here with.
Speaker 5: Chad Stumpo, Angelina.
Speaker 7: And Paul English.
Speaker 2: What a group?
Speaker 7: Huh m?
Speaker 2: This is the fourthument that been Senny what. I don't know.
Speaker 2: There used to be three sem beats a full house.
Speaker 2: But okay, whatever, that's that. What are we had talking about?
Speaker 7: We can talk about whatever you want. We can talk
Speaker 7: about Boston, we can talk about Kayak mental health, nonprofit.
Speaker 2: We could talk about anything. That's what good about you?
Speaker 4: Andy? Right?
Speaker 2: We could talk about everything and anything.
Speaker 5: We're right, But I have a question, Paul, what inspired
Speaker 5: you to pursue technology and entrepreneurship?
Speaker 7: I would say, you know, as a little kid, I
Speaker 7: was really into the cars.
Speaker 2: Not to hold you. Do you know what if my
Speaker 2: son pronounces is ours? Yeah differently? Right? Yeah?
Speaker 5: I grew down so you pronounced I just know that.
Speaker 2: Go ahead.
Speaker 7: Yeah. My speech dysfunction gets worse after drinking. I'm pretty
Speaker 7: good right now. I loved cars and trucks. I bought
Speaker 7: my first car when I was twelve. I couldn't drive
Speaker 7: ecause I didn't have a license, but my brother Dan
Speaker 7: and I saved up money from a paper root and
Speaker 7: bought a Ford, a quantoline van for one hundred dollars.
Speaker 7: And if you asked me at age fifteen or sixteen.
Speaker 7: My aspiration, I might have said, to own a car
Speaker 7: wash would have been my life goal.
Speaker 3: That's different.
Speaker 7: I don't know. I think the thing that got me
Speaker 7: into tech was when I was fifteen or so, my
Speaker 7: mom bought a computer for the family. It was called
Speaker 7: a Commentovic twenty and I read the manual and learned
Speaker 7: how to write code, and I started developing my own games.
Speaker 7: And that was incredibly, incredibly fun for me. And then
Speaker 7: my older brother ed. He's I'm number six of seven.
Speaker 7: He's the oldest of the seven. He is actually a
Speaker 7: pretty famous programmer. He created the video game Frogger on
Speaker 7: the Atari platform, and I remember when he was working
Speaker 7: for Parker Brothers working in that game.
Speaker 2: You didn't say that your brother does.
Speaker 4: Hold on?
Speaker 5: Hold on You self taught yourself coding. Yeah, that's incredible.
Speaker 5: Just to learn to go to school for it is
Speaker 5: hard enough. I have friends are in it self taught.
Speaker 4: That's incredible.
Speaker 7: Yeah. It was a lot of fun. I really I
Speaker 7: liked it. My high school years were cars, girls, sports, music,
Speaker 7: and computers like all of that.
Speaker 5: So I put the computer in there.
Speaker 7: Yeah. I liked the I liked designing games, and I
Speaker 7: liked because I was a musician.
Speaker 2: I also designed sound hold on He's sixty. Computers were
Speaker 2: very very new to us generation. They would use big
Speaker 2: things that look like big TVs from nineteen fifty two. Okay, good.
Speaker 7: But I loved programming. I loved doing music. I ended
Speaker 7: up going to mass Boston and I studied music and computers,
Speaker 7: and I got my master's degree. My master's thesis was
Speaker 7: I built a music synthesized so I wrote all the
Speaker 7: code for it and designed it. So that took both
Speaker 7: my music education and my computer education. But then I
Speaker 7: was incredibly inspired my brother and seeing how well he
Speaker 7: was doing his game Frogger. He sold four million copies
Speaker 7: in one year the first year it was, so I
Speaker 7: was thinking there might be something in this computer stuff here.
Speaker 7: So I by that time I was self taught programmer,
Speaker 7: just starting as a freshman UMass. But I knew how
Speaker 7: to code, and I found an internship and I ended
Speaker 7: up working almost full time for the five years it
Speaker 7: took me to get my bachel's degree as a programmer
Speaker 7: for different types of companies. I worked for the US
Speaker 7: Air Force, I worked for medical technology company, a gaming company,
Speaker 7: accounting company, and I just had a blast. I love
Speaker 7: designing things. I love designing products.
Speaker 4: That's awesome. That's an incredible way to get started. And
Speaker 4: so would you major in US? Where'd you say? God?
Speaker 7: Yeah, I went to UMAs Boston and I studied music
Speaker 7: and computers give you designs?
Speaker 4: And then right after that, just where'd you start off?
Speaker 7: After my graduation, I worked for a software company in
Speaker 7: Cambridge called interly if they built publishing software. I worked
Speaker 7: for them for six years. Started as a programer. I
Speaker 7: ended up running engineering and then my last of the
Speaker 7: area in marketing, which is kind of a whole nother
Speaker 7: crazy show, because I all, yes, that was my training.
Speaker 2: And most it was self trade.
Speaker 7: Yeah, self taught, and by that time I did take
Speaker 7: course in college, but I started my career of self taught.
Speaker 7: But then I was going to school at night at
Speaker 7: your mass So I learned a lot.
Speaker 2: Let me ask you an honest question, did you really
Speaker 2: get that much out of going to school or did
Speaker 2: you really figure this out on your own?
Speaker 7: I'll tell you the main thing. I had one really
Speaker 7: good professor guy named Bob Morris, that I learned things
Speaker 7: from him about imaging and graphic and design, which helped
Speaker 7: me in my career. The main thing I learned at
Speaker 7: your Mass which completely changed my worldview is your Mass
Speaker 7: is I think the third most diverse school in the country,
Speaker 7: most diverse school in New England, and I had students
Speaker 7: from like every country. It was crazy. They actually gave
Speaker 7: me an honorary doctorate a few years ago, and at graduation,
Speaker 7: the chancellor told me that the kids graduating that year
Speaker 7: spoke sixty one native languages as a primary language, sixty
Speaker 7: one different languages. I couldn't even name sixty one languages.
Speaker 7: So it's a very diverse school. And I like that
Speaker 7: opened my eyes to traveling, and I since it become
Speaker 7: an addicted travel I'm traveling.
Speaker 2: At least over really out of That's what I got.
Speaker 7: To your Mass is appreciation for the cultures and a
Speaker 7: hunger to travel.
Speaker 2: You guys, you both always feel the need for speed. Huh,
Speaker 2: that's part of it. Yeah, okay. And then Chad, you
Speaker 2: had another question you wanted to ask, Paul.
Speaker 5: How did your education influence your approach to business?
Speaker 7: I think it was I loved that I could work
Speaker 7: as a programmer and go to school at the same time,
Speaker 7: kind of balancing both of those things, and it taught
Speaker 7: me early on that you can do more than one
Speaker 7: thing at a time. And I was taking you know,
Speaker 7: liberal arts courses, history courses, but working during the day.
Speaker 2: And what did you say, Wait, hold on, won't you
Speaker 2: say liberal lots to me? Begin it is like just
Speaker 2: another four years of high school. That's how I see
Speaker 2: liberal lots. Right, Let's just go to high school for
Speaker 2: four more years. Because you're not gearing into anything.
Speaker 7: No, it's not. It's definitely not aiming you towards a
Speaker 7: career maybe Starbucks.
Speaker 2: At best, okay, and coming out with a lot of debt.
Speaker 2: Could you have done what you've done self? Like I've
Speaker 2: self taught my whole weight, right, So it was like
Speaker 2: I went to some great college, right, I did go
Speaker 2: to Wetworth.
Speaker 7: But I guess what I would say is I've.
Speaker 2: Been the same without going programing, and I left.
Speaker 7: I probably would have done okay without college. But what
Speaker 7: I did need and benefited from greatly is having some
Speaker 7: unbelievable mentors at work. So I was self taught as
Speaker 7: a programmer, got my first job as a programmer at
Speaker 7: age eighteen, and then worked with some unbelievable people and
Speaker 7: would study their code and how they design things, and
Speaker 7: how they wrote code and how they tested code and
Speaker 7: how they made code run fast. And I learned and
Speaker 7: by working.
Speaker 2: Yeah that is my producer opening up my cocine right now.
Speaker 2: If you're hearing that right that I shouldn't be drinking,
Speaker 2: go ahead.
Speaker 7: Well, so I learned from great mentors along the way.
Speaker 7: And that was really the beginning of my career was
Speaker 7: the working, not the school.
Speaker 2: Okay, got it. I still say, no matter what you did,
Speaker 2: you were going to be successful because I think you
Speaker 2: had that drive and you know where it stemmed from
Speaker 2: delivery newspapers when you're a little kid.
Speaker 7: Yeah.
Speaker 2: The things that we don't do anymore. The things that
Speaker 2: parents don't make their kids do it anymore.
Speaker 7: Right, I knock on doors, ask people for money.
Speaker 2: Yeah, all the things. Now, we'd be afraid for our
Speaker 2: kids to go knock on somebody to do it because
Speaker 2: they might pull them in and hurt them and kill
Speaker 2: them and put them in.
Speaker 5: The basement of kids snow anymore.
Speaker 2: Yeah, that's a big mistake too. But that's the whole key. See,
Speaker 2: that's our generation. We wanted to make money eighteen. You
Speaker 2: didn't have to throw us out of the house. We
Speaker 2: were leaving. We wanted to go like we're eighteen, we're
Speaker 2: out of We're going like I wanted to get out.
Speaker 2: Even I had the greatest parents of the world, had
Speaker 2: a beautiful home, no one bothered me. I wanted to
Speaker 2: be independent. I wanted to make money.
Speaker 7: That's tell a funny story. I used to work at
Speaker 7: a pharmacy in that I'm called Meddi mart. I don't
Speaker 7: know if they existed anymore.
Speaker 2: I was a waitress and my father's nightclub whacking it
Speaker 2: out like literally, which the nightclub Maxwell's in Copley.
Speaker 7: Oh my god, amazing.
Speaker 2: Yep.
Speaker 7: So okay, So just to show what a workaholic. My
Speaker 7: dad was a workaholic, and I think I was got
Speaker 7: the work ethic from him. But one night I ate
Speaker 7: but the other.
Speaker 2: Clubs, like I could have been working at nine Leans Down. No,
Speaker 2: he stuck me in Maxwell's, a little bit more of
Speaker 2: a mature group of Yeah, yeah, go ahead.
Speaker 7: So just to show you like the work ethic that
Speaker 7: my father, that I modeled after my father, one night
Speaker 7: I kind of over imbibed. I think it was on
Speaker 7: a Friday night. I was probably sixteen or seventeen, and
Speaker 7: I woke up Saturday with which themost unbelievable worst hangover
Speaker 7: in the world. And I called the pharmacist who was
Speaker 7: the manager, and I said, there's no way I can
Speaker 7: make it in today. And he said, do a little
Speaker 7: drinking last night. I said, yeah, maybe a little. He said,
Speaker 7: come in, I'll fix you up. And I couldn't drive.
Speaker 7: I still was like, just not feeling well from the night.
Speaker 7: I took a taxi to work. I'm making two dollars
Speaker 7: and thirty five cents an hour and I called the
Speaker 7: taxi to bring me to work. My father was like,
Speaker 7: what are you doing. My father was always worried about
Speaker 7: spending money and saving money. But I took a taxi
Speaker 7: to work and the farmers. I still don't know to
Speaker 7: this day what he gave me. He gave me something.
Speaker 7: He said, you cannot tell people what I gave you
Speaker 7: because I'll lose my license.
Speaker 4: Gave you.
Speaker 7: I wish I knew what he gave me, because it
Speaker 7: fixed that hangover immediately. And I think a ten hour
Speaker 7: shift that thought. I'm Citty Stumple. You listen a Toughest
Speaker 7: Hills on wc News Radio ten thirty will be right.
Speaker 6: Back, sponsored by Pillow Windows of Boston. Next Day Molding
Speaker 6: and Kennedy Carr.
Speaker 2: And welcome back. It's a top of Nails. I'm Setty
Speaker 2: Stampo on WBZ News Radio ten thirty and I'm here
Speaker 2: in the studio with Angelina and the Star Child, Chad
Speaker 2: Custochia and the famous Who.
Speaker 7: Are you pointing out?
Speaker 2: You?
Speaker 7: Paul and Gush?
Speaker 2: I love you? Okay, Angele, you had a question.
Speaker 3: Yes, Paul, can you share memorable moments or milestones from
Speaker 3: Kayak's growth?
Speaker 7: Yeah? Boy, it was such a fun ten years of
Speaker 7: my life. One of my favorite moments was I was
Speaker 7: flying to New York. We actually Kayak was born in
Speaker 7: Connecticut and Boston. The engineers well in Boston, and our
Speaker 7: marketing team was in Connecticut and New York. So I
Speaker 7: go to New York a but once a week. And
Speaker 7: on the plane next to me there was a woman
Speaker 7: who had her laptop open and she was running Kayak.
Speaker 7: And this is we were a year old. It's like
Speaker 7: no one knew who Kayak was, no one's using it,
Speaker 7: and I was sitting next to our watching her use it,
Speaker 7: and I'm like, this is very cool. I think that
Speaker 7: maybe people are going to find out about this because
Speaker 7: in the first year it was just me begging my
Speaker 7: high school friends, my brothers and sisters, can you please
Speaker 7: try using this product and give me feedback. But once
Speaker 7: it started taking off on its own, that was exciting.
Speaker 7: When I found other people using it another milestone that
Speaker 7: was also really cool. At one point I forgot what
Speaker 7: year this was. But if you went to google dot
Speaker 7: com homepage and you just typed the letter K and
Speaker 7: you pause for a second, the first word that would
Speaker 7: come up, it was kayak. And that was when we
Speaker 7: were already we were growing very very rapidly. But I'm like,
Speaker 7: the day we owned a letter that was cool, Like
Speaker 7: we're the most popular K word on on Google. That
Speaker 7: was fun. And then there's all these financial milestones. We
Speaker 7: we took a public two hundred employees, three hundred million
Speaker 7: in revenue, that's a million and a half for employee.
Speaker 7: It was. It was an incredibly fun ride, a lot
Speaker 7: of good milestones along the way.
Speaker 3: Wow.
Speaker 2: So it's when you first saw somebody using your app that.
Speaker 7: Was the most exciting thing to me.
Speaker 2: I couldn't stand that. Yeah, I couldn't stand that because
Speaker 2: you're not okay, wow, they're really were we on a
Speaker 2: plane with something? You were?
Speaker 7: I was on a plane. She was sitting next to
Speaker 7: me using Kayak was very very cool.
Speaker 2: And that was the first time you saw somebody that
Speaker 2: wasn't family friends on there.
Speaker 7: I told her, I said, what do you think of that,
Speaker 7: psy Kayak And she said, oh, it's this great news site.
Speaker 7: I said, I'm the founder, and she didn't believe me.
Speaker 7: She thought I was hitting on her.
Speaker 5: Now, question, what was that feeling you had inside when
Speaker 5: you saw that.
Speaker 7: It was amazing? Then I started wondering, I wonder if
Speaker 7: anyone else in this plane is ever heard of Kayak,
Speaker 7: because it was very very early on in the history
Speaker 7: where no one knew about us yet.
Speaker 5: So the next thing you know, he's going to the
Speaker 5: bathroom in the front of the plane, in the back
Speaker 5: of the way looking at people.
Speaker 2: Hey, hey, hey, you might want to try and hate.
Speaker 2: That's pretty cool. And then take us from I have
Speaker 2: a question, because you're in your second year and I
Speaker 2: know we've touched upon this, we touched upon the sale
Speaker 2: when you sold your stock. Now you realize you're exactly
Speaker 2: how old now forty.
Speaker 7: I was in my forties when we sold it in
Speaker 7: two thousand and thirteen. Different paths. I think I just
Speaker 7: turned just turned fifty and we sold it for two billion.
Speaker 2: Yeah, it started at forty and at fifty, did you
Speaker 2: say I'm set for life?
Speaker 7: No, this is funny. So when we were negotiating the
Speaker 7: sale of the company.
Speaker 2: Let me rephrase that. Did you take ten minutes to
Speaker 2: enjoy the high of it?
Speaker 7: What I did during the negotiation of the sale is
Speaker 7: I calculated how much money my assistant was going to make.
Speaker 7: I didn't know how much money I was going to make.
Speaker 7: I knew it was a lot, but I really she
Speaker 7: told me she wanted to buy a house, and I'm thinking, like,
Speaker 7: I got to sell this enough that she can buy
Speaker 7: a house. And I knew how much my programmers would make.
Speaker 7: I knew much my assistant made, and we had There
Speaker 7: were two hundred employees. Over half of them became millionaires
Speaker 7: that day.
Speaker 2: And that was just pump you that you're not worried
Speaker 2: about your own pocket, you're worried about what your assistant.
Speaker 7: Well, no, and I'll tell you, you know, to a
Speaker 7: point we were talking about off here earlier. Literally the
Speaker 7: next the Boston Globe put me in the front of
Speaker 7: the globe that day, and literally the next morning I
Speaker 7: started having panic attacks because here, I suddenly had all
Speaker 7: this money. I grew up with no money, and I
Speaker 7: didn't know what to do with it. I was afraid
Speaker 7: of it, and I felt like I didn't deserve this money.
Speaker 7: I want to give the money away.
Speaker 2: Well that's why I asked you if you ever had
Speaker 2: impost syndrome.
Speaker 7: Yeah I did. I did.
Speaker 2: I asked you that off here.
Speaker 4: Yeah.
Speaker 2: Now I'm asking now that you're saying that.
Speaker 7: Yes.
Speaker 2: So a lot of people don't understand what imposta syndrome means.
Speaker 2: They think that it means you're trying to be somebody
Speaker 2: you're not, like I'm going to be you when I'm
Speaker 2: really Cindy. Okay, that's not what impost syndrome is. You
Speaker 2: know what imposta syndrome is, right.
Speaker 7: Yeah, it's basically thinking I'm going to walk into the
Speaker 7: office Monday morning, there's going to be someone there like
Speaker 7: arresting me, say you shouldn't be here, like you don't
Speaker 7: deserve this.
Speaker 2: That's how you that's how your analogy of it and
Speaker 2: my analogy of it is when you have impostera syndrome
Speaker 2: is you don't believe like you've created this company, never
Speaker 2: earned it, that I've earned that it's your wealth and
Speaker 2: it's your brain, and some people, a lot of people
Speaker 2: go through it. A lot of my clients have gone
Speaker 2: through it, and I don't think I've ever had that.
Speaker 2: I just don't ever give myself that five minutes to say,
Speaker 2: you know that a girl every you know like you don't.
Speaker 7: I celebrated the success of the team. People were very
Speaker 7: very happy. It's exciting, you know, most.
Speaker 2: Out of shales A lot of people's lives that.
Speaker 7: Day, we did and it was very nice. Many many
Speaker 7: years later, I was at a party after I had
Speaker 7: left Kayak and I rented to someone who used to
Speaker 7: work there in the early years, and she said, I
Speaker 7: just have to let you know that. I mean, she
Speaker 7: was exaggerating, but she said, due to you, I paid
Speaker 7: off my house and sent my kids to college, and
Speaker 7: I paid for all of that with Kayak stock. I
Speaker 7: thought that was pretty cool. It was cool that she
Speaker 7: said it to me.
Speaker 2: When you started that company, did you think that you'd
Speaker 2: end up where you ended up with that one company
Speaker 2: if you get the other companies.
Speaker 7: No, So I'm again. I'm a programmer by training, and
Speaker 7: my career is designing software, running design teams. And when
Speaker 7: I ran into Steve Haffner, and he said he wanted
Speaker 7: to create a travel company. I went home that night
Speaker 7: and spent some time on Expedia, which is the number
Speaker 7: one travel site back then in two thousand and four,
Speaker 7: and I remember thinking, this site is like epileptic seizure inducing.
Speaker 7: There's so much stuff happening, ads popping up everywhere, and
Speaker 7: I'm thinking I can design something better than this. I
Speaker 7: wasn't thinking financially, but I was thinking, I know I
Speaker 7: can build a team. They can build a better process.
Speaker 2: Deforment, why would you ever have imposted to ine that
Speaker 2: you knew, you knew.
Speaker 7: The money intimidating. The money intimidated me.
Speaker 2: The money.
Speaker 7: Yeah, we we never thought of ourselves as not having money.
Speaker 7: But I never encountered a rich person ever until post college.
Speaker 7: Everyone around me was blue collars fury. Yeah. So the
Speaker 7: concert we were right next to Newton, we were. Yeah,
Speaker 7: you spend any time in Newton. I don't think we
Speaker 7: were allowed in there.
Speaker 2: You're right on Newton's cote tails, right, we were. And
Speaker 2: you guys never went to like Losy Andison in Brookline
Speaker 2: that you didn't cross two towns.
Speaker 7: I've skated at Lassi Anderson.
Speaker 2: Okay, yeah, but keep going. So I'm just wanting to.
Speaker 7: Show the money with the money was intimidating. And I
Speaker 7: went to a friend of mine, Michael White, and I
Speaker 7: knew he had an uncle was a builder. Do you
Speaker 7: know Tom? Do you know White Construction company? JF. White Construction.
Speaker 7: So Michael's uncle Thomas J. White, He's now passed away.
Speaker 7: He was the founder of Jfhy Construction Company. And when
Speaker 7: I sold Kayak, he was eighty at the time, and
Speaker 7: I knew he had given a bunch of his money away.
Speaker 7: So I had all this money. I was afraid of it.
Speaker 7: I want to give it away. So I met with
Speaker 7: this guy Tom White, and I said, I made all
Speaker 7: this money, I want to give it away. Who should
Speaker 7: I give it to? And he said, go to Haiti
Speaker 7: and meet my friend Paul Farmer, and then go to
Speaker 7: a homeless shelter. Meet my friend who runs a homeless
Speaker 7: shelter in Boston. Anyway, it's now twenty years later, and
Speaker 7: you look where I've given all my money away. I
Speaker 7: paid the tuition for ten thousand kids a year in Haiti.
Speaker 7: I have forty schools and three hundred and fifty teachers,
Speaker 7: and I now do a lot of give all.
Speaker 2: Your money away most of it. You gave most of
Speaker 2: that away for half. Yeah, oh, you would have had
Speaker 2: to give half to the government anyways.
Speaker 7: Well yeah maybe right.
Speaker 2: Like, okay, so if we can break it down some numbers,
Speaker 2: but you still give half of the weight over half, yeah,
Speaker 2: and then you stay played the tax on the other half.
Speaker 7: But then I started making more money after that too,
Speaker 7: because I sold a few more companies after.
Speaker 2: Kayak, Okay, you're very you're okay, hold on atlease, get
Speaker 2: this straight. You sell one hundred and forty million in stock,
Speaker 2: you give half that money away, right.
Speaker 7: Not immediately, but over time and time.
Speaker 2: Yeah, but money was making money.
Speaker 7: Yeah exactly. But I'm investments are doing well.
Speaker 2: Investments are doing well. But that was what year.
Speaker 7: I sold the company in twenty thirteen.
Speaker 2: Well, in twenty thirteen, we weren't making very much money
Speaker 2: on an interest, so let's call that what it was, right,
Speaker 2: and then you had to go into CDs and whatever
Speaker 2: my markets were in paying we're making a most might
Speaker 2: today and we've made in twenty years.
Speaker 7: This has been unbelievable, unbelievable.
Speaker 2: Correct sowe stock market and between you know, money market
Speaker 2: funds and everything else. But okay, so then you go
Speaker 2: and open up more companies and then you make more money.
Speaker 7: Yeah, and gave way more.
Speaker 2: Money and gave okay, and he likes to go and
Speaker 2: they're going to find like a waiter waitress that gets
Speaker 2: like a ten thousand dollars tip. That's the things he
Speaker 2: likes to do, like things about nature. So he's a
Speaker 2: very generous man. Right, So you just keep making money
Speaker 2: to keep giving it away, right.
Speaker 7: It's incredibly fun to give away money.
Speaker 2: We talked about that earlier in the other segment right
Speaker 2: that we had a few months ago. But he does.
Speaker 2: He likes to give away money all day. I thought
Speaker 2: we're going to break. I'm sitting stumbling. He listen to
Speaker 2: WBC News Radio ten thirty and We'll be.
Speaker 6: Right back, sponsored by new Brook Realty, Boston, would Smaller Insurance,
Speaker 6: World Auto Body and Tasca Drive Auto Body.
Speaker 2: Company and welcome back to Toughest Nails on WBC News
Speaker 2: Radio ten thirty. And I'm Cindy and I'm here.
Speaker 7: With Angelina, Chad and Paul.
Speaker 2: Okay. I think Angelina, I wanted to ask you a question.
Speaker 3: Yes, I would love to know what advice would you
Speaker 3: give aspiring young entrepreneurs.
Speaker 7: I think the main thing is if you look at
Speaker 7: all the jobs you could get, like maybe work for
Speaker 7: big tech company like Google, or work for a little
Speaker 7: startup or a medical company or finance company. Go interview
Speaker 7: at two or three or four or five companies, and
Speaker 7: each time you interviewed a company, try to figure out
Speaker 7: you might meet five or six people who are the
Speaker 7: two or three during that interview that you actually would
Speaker 7: end up spending your days with. And across let's see
Speaker 7: you do with five companies. Across those five companies, which
Speaker 7: one has a stronger three percent team? Because early in
Speaker 7: your career what's really important is acceleration of skills. You
Speaker 7: want to learn as fast as possibly can. So whatever
Speaker 7: company has a stronger team, you'll learn faster and you'll
Speaker 7: develop faster.
Speaker 2: Okay, So I always stay out on the job sites.
Speaker 2: My delivery can really stink at times, right, like really
Speaker 2: like pointed, but my intent is always one thousand percent
Speaker 2: and that's because it's a hard courre. What I do
Speaker 2: is hardcore out there, right, Like you're literally running hundreds
Speaker 2: of guys all day long, with hundreds of different personalities.
Speaker 2: So we're in two different, completely different industries. You get
Speaker 2: to work with smotty pants and I get to work
Speaker 2: with we.
Speaker 4: Don't eve have high school degrees.
Speaker 2: Of high school degrees, I have to go push the
Speaker 2: brew me to make somebody understand what's the push to
Speaker 2: brew me? They still don't understand, right, But we're in
Speaker 2: two different businesses. So I'm always pushing Kids that don't
Speaker 2: have the intellect, that don't are not good students. Right,
Speaker 2: I was a terrible student. I guess I could have
Speaker 2: been a great student. I just really wasn't into school
Speaker 2: except the social aspect, right, getting dressed here and makeup,
Speaker 2: looking good and going to school that was fun to me.
Speaker 2: Social was fun. Sitting in the classroom watching fifteen minutes
Speaker 2: of o'clock.
Speaker 7: Go, I was like, oh god, a nightmare for me.
Speaker 2: Nightmare, total nightmare. And then you call on me. My
Speaker 2: legs would start swinging and I'd be like, oh god,
Speaker 2: where they leave off on the paragraph because I wasn't
Speaker 2: paying attention. And then you know, the teacher always pays
Speaker 2: attention to the kid that's not paying attention, right, the
Speaker 2: kid raised the hand. They don't call the they call
Speaker 2: and Cindy what. So I pushed a skilled you know,
Speaker 2: the skill because we have a massive skilled gap out
Speaker 2: there for kids. We need plumbers, electricians, hvac guys. And
Speaker 2: I heard mister wonderful say something last week on the news,
Speaker 2: and we all know who mister wonderful is, right from
Speaker 2: Shark NK and his advice four or five years ago
Speaker 2: was for kids to get into this this this now.
Speaker 2: His advice is get into the skilled labor, get into editing,
Speaker 2: engineering of editing, and content creator. Not being a content creator,
Speaker 2: but get like I need footage all the time to
Speaker 2: put out for content. And that's where he's pushing and
Speaker 2: for you, for kids that know how to understand and
Speaker 2: do this, you're pushing that industry of hou.
Speaker 7: It's not necessarily tech. I mean, tech is a great
Speaker 7: industry to work in. Healthcare is a good industry. There's
Speaker 7: a lot of incredibly rewarding things you can do if
Speaker 7: you're part if you work for pharmaceutical and you this
Speaker 7: generation you want to start up.
Speaker 2: Money is the way they want to make money tomorrow.
Speaker 2: They don't want to wait ten years and fifteen years.
Speaker 2: You understand that, right. I'll tell you one thing, rest
Speaker 2: span of a fleet, I.
Speaker 7: Tell one thing. Really scared, I just read about this
Speaker 7: generation they interviewed twelve year olds in China and twelve
Speaker 7: year olds in the US. They said, what's your career aspiration?
Speaker 7: And China number one care aspiration we want to be
Speaker 7: an astronaut. In the US twelve year old number one
Speaker 7: core aspiration.
Speaker 2: I want to be in famous TikTok, famous influencer. Influencer.
Speaker 7: That's scary.
Speaker 2: Yeah, it's very scary, very scary, because one percent might
Speaker 2: make it. Yeah, one percent. So what is that telling
Speaker 2: you look at? I think my grandmother said the best.
Speaker 2: She died eight years ago at ninety eight years old,
Speaker 2: and she had all her faculties together at ninety seven,
Speaker 2: and she'd see my kids the last like five years,
Speaker 2: always on their phones, and she'd say, that's going to
Speaker 2: be very very smart. Three PhDs when women didn't go
Speaker 2: to college back then, and she'd say, sinning, that's going
Speaker 2: to be the demise of your children if you if
Speaker 2: you don't control some of that, you know, pop up.
Speaker 2: Because she noticed every baby, you know, she was ninety
Speaker 2: five at that time, and everybody off for dinner and
Speaker 2: look at their phones. So isn't it crazy how technology
Speaker 2: can work in such a great way, But if you
Speaker 2: take advantage of it. It can hurt you in other ways.
Speaker 2: You look, now, Paul, come on, we go for dinner
Speaker 2: with eight people and seven people are on their phones. Well,
Speaker 2: why are we all together? Then my son started this
Speaker 2: when he come back from school on school vacations and say, okay,
Speaker 2: we'll all go for dinner. But everybody put your phone
Speaker 2: in the middle of table. And the first person that
Speaker 2: picks up their phone, the first person I picks up
Speaker 2: their phone, he'd say, you're going to pay the bill.
Speaker 7: So what I do for my Tuesday night dinner is
Speaker 7: I bring for fourteen years of my siblings. First one
Speaker 7: to touch the phone does the dishes?
Speaker 2: Ye okay, yeah, So everybody says a but we're all addicted,
Speaker 2: right right. So but I've got clients texting me all day,
Speaker 2: all night. I got to get back to them. And
Speaker 2: every time they text me, it's like life or death, right,
Speaker 2: there's always nine to one one in my business. There's
Speaker 2: a snowstorm coming, there's a blizzard coming, there's whatever, right,
Speaker 2: And then I do get the beautiful texts that say, hey, Sinny,
Speaker 2: just want to say thank you for a beautiful home.
Speaker 2: But those are far and few and in between, right,
Speaker 2: like you get that.
Speaker 7: I will say something really quick. Advice to young people
Speaker 7: say thank you, Yes, say thank you. Tell people you
Speaker 7: appreciate them.
Speaker 2: They don't do that.
Speaker 7: They are doing write notes, write letters. I have nephews
Speaker 7: that write.
Speaker 2: I will still do that.
Speaker 7: My nephews Matt and Mitchell each just wrote me a
Speaker 7: card thanking me for something question written.
Speaker 2: Could you read the writing? I could really because the.
Speaker 7: Block writing, I can read it.
Speaker 2: It's it's look. I guess the greatest thing about your
Speaker 2: brain is you kept that brain young in technology. So
Speaker 2: you did an age. So when you said to me
Speaker 2: you were sixty, I'm like, you show you're sixty. Like,
Speaker 2: so you've kept that brain if you was young because
Speaker 2: of technology. And I think I've kept my brain young
Speaker 2: being out there in construction, boots on the ground. And
Speaker 2: I never want to change that. Like I don't want
Speaker 2: to sit in an office and no, I'd rather be
Speaker 2: on job sites and ranton and raven and doing what
Speaker 2: I do. But it's people like you and I can
Speaker 2: make a difference. We're just in two different worlds and businesses.
Speaker 7: Your I'm virgo, you're cancer cancer.
Speaker 2: Yeah, right, so we want to help everybody. Okay, so
Speaker 2: we know you know, we know about the dating app
Speaker 2: that you could come out. Will you stop at that one?
Speaker 7: Absolutely not? I think if I had to, let's say
Speaker 7: there was no way to make money in tech. Let's
Speaker 7: say there were no tech companies and I had to
Speaker 7: work at Starbucks or whatever to be an Uber driver.
Speaker 7: I actually am an Uber driver.
Speaker 2: What do you mean? You're an Uber driver?
Speaker 7: I'm Uber driver? Get OUTI I'll show you my rading.
Speaker 2: What are you talking about?
Speaker 4: Driver?
Speaker 7: Watch this all right?
Speaker 5: I feel like a horrible human vingnam you should?
Speaker 7: What do you mean watch us? What's my rating?
Speaker 2: Four point ninety six?
Speaker 7: Wait minute, my driver rating?
Speaker 2: Where's the other rating? I don't even know how to
Speaker 2: use this thing? Drivers rating?
Speaker 7: This is the driver app? Almost five four point nine six.
Speaker 7: Let's I don't do it.
Speaker 2: Let me get this, okay, you just you just get
Speaker 2: in your car and you pick people up in Uber.
Speaker 7: Yeah, my girl. I'll say to my girlfriend, do you
Speaker 7: man if I drive Ober for an hour? So she's like, sure,
Speaker 7: I don't mind that you find strangers more interesting than me.
Speaker 5: The next hour, I thinks found the new man.
Speaker 4: The most amazing.
Speaker 2: I gotta understand this, so you'll just get out of
Speaker 2: your car a multi millionaire guy, right, millions, and you
Speaker 2: just drive some strangers around and they have no idea
Speaker 2: who you are, and you have no idea who they are.
Speaker 2: Just to get to what keep your feet on the beat.
Speaker 7: It's basically all of us should do acts of service
Speaker 7: in different ways. And let me drive someone to a
Speaker 7: medical appointment. It's a very minor thing.
Speaker 2: Can you do it? Like in the safe eeries?
Speaker 4: Oh sorry?
Speaker 5: Can you run for president? I think you made this
Speaker 5: roll a freaking country one. I want to hang out
Speaker 5: with him more. I'm already feel like a better I
Speaker 5: want to do better. Already, hold on a second.
Speaker 2: He makes you wanted to do. So you'll say to
Speaker 2: your your fiance, I want to go out and just
Speaker 2: drive anoover for a couple hours, no problem, And she'll
Speaker 2: be like, sure, you want to go hang out with
Speaker 2: strangers and not me.
Speaker 4: Do you ever do public speaking events? No?
Speaker 2: But I'm going to get him on chatter. Yeah, because
Speaker 2: you're going to understand what chatter is because you can
Speaker 2: make it so many people listen to you that by
Speaker 2: talking to these people on it's like it's like a clubhouse,
Speaker 2: but it's much more advanced and even blows by xpaces
Speaker 2: cool and I'll just stick your rooms with me. And
Speaker 2: but now you just really blew my mind.
Speaker 5: So I feel like this is the movie. Now there's
Speaker 5: the TV shows are coming.
Speaker 2: Out with maybe it should be a TV show, it
Speaker 2: should be a Lifetime original. So you'll just get in
Speaker 2: and start driving a room. And do you ever getkogle people?
Speaker 2: And you can't.
Speaker 7: I've had only two really bad rides. When was that
Speaker 7: drug deal gone bad?
Speaker 2: No?
Speaker 7: And the other one was I drove these two guys
Speaker 7: and I'm dropping them off at a club and I said,
Speaker 7: how do you like Boston? They go, It's great, but
Speaker 7: all the women are bitches? And I said all the
Speaker 7: women and they go, yeah, you know, if it's all
Speaker 7: the women, that might not be the problem. I don't
Speaker 7: think they give me five stars.
Speaker 2: I were going to break. This is Citdny Stumple. You
Speaker 2: listen Toughest Nails on WBZ News Radio ten thirty. He'll
Speaker 2: be right back and welcome back to Toughest Nails on
Speaker 2: WBZ News Radio ten thirty. I'm here with Angelina Chad
Speaker 2: by Paul. Everyone knows by now, I would think after
Speaker 2: seven years on radio, I'm Sidney Stumbo. Okay, talk to me.
Speaker 2: We all know able. The dating app that is out
Speaker 2: and running right now go.
Speaker 7: The app is called LOLA. It stands for Love Language
Speaker 7: l O l A dot com and we're the best
Speaker 7: dating app in Boston.
Speaker 2: Just launch in Boston and then how do they find
Speaker 2: it again?
Speaker 7: LOLA dot com l O l A l O l
Speaker 7: A dot com.
Speaker 2: That's right, join, get on there, start dating. Everybody. Have
Speaker 2: a great, safe weekend, and we'll see you next weekend.
Speaker 2: This is Cindy Stumbo Toughest Nails on WBZ Radio News
Speaker 2: ten thirty