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Tech Mogul & Activist, Paul English

Aug 04, 202440 min
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Speaker 1

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

Speaker 2

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 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, real estate, development, design and more.

Speaker 7

Here unpredictable. Every time I think I know what you want, you switch it out. But that's what makes your houses all your day.

Speaker 1

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

Speaker 2

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

Speaker 3

Angelina?

Speaker 2

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

Speaker 7

About in Boston, a little bit of mental health.

Speaker 2

A little bit of a little bit of kayak. Let's okay. So, like we said before, it's kind of cool that we have like panic attacks now and by Pola, like this is like the cool thing to be like a screwed up person and mentally screwed up. Yeah, I walk around pick attacks. But and then you have you suffered from bipolar and some panic attacks along the way, and ganetic by the way, right now, proven that i'd just put 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 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. So with that being said, can you have problems in your life that you can still make it big healthy if you want to?

Speaker 7

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

Speaker 2

It's a little hot.

Speaker 7

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

Speaker 2

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 not have.

Speaker 2

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

Speaker 7

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

Speaker 2

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, never lonely in those sometimes. Yeah, did you like growing up with all those kids?

Speaker 7

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

Speaker 2

Why.

Speaker 7

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

one night at my house. It turned out to be an election night two thousand and eight, Obama's first win, and I invited people over for dinner to watch the election, and we had such a good time with my siblings.

I think there were six of us that night. That next week, one of my sisters, my sister Barbera, said an email saying, let's do that again next Tuesday, and just became a tradition we did every Tuesday night I have had next to our neighbor, Nicholas, passed away last year at age ninety six, but he came to my dinners every year for I think he came for about ten years.

Speaker 2

What happens when you're the most successful.

Speaker 7

Sibling, most successful you know in some ways maybe right, 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 they keep me honest because they know the good, the bad, 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 a lot of people ask me for stuff. I'll open up my iPhone here and show you to eat my email. Right now, I get asked every day, but not my best friends and not my siblings.

Speaker 2

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

Speaker 4

Virgo, right, I know all about it.

Speaker 2

Yeah, so you'll be chased until that person doesn't like gets expected.

Speaker 5

Yeah, but virgos, we keep doing.

Speaker 2

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

Speaker 5

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

Speaker 2

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

Speaker 7

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

Speaker 2

Six for six.

Speaker 7

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

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

on Kayak. And it was an incredibly fun ten years of my life with lots of ups and downs and parties and just it was a great, great ten years of my life. And you howled I was forty when I saw at Kayak.

Speaker 2

Okay, so forty was your third company? You started at forty years old, you'd already had three under your belt that you sold.

Speaker 7

Obviously, Yeah, I guess under my belt.

Speaker 2

Yeah, two underr belt. This was the third. Okay, now you start to see money? How many years into that company?

Speaker 7

We started growing rapidly in year two? So year two and three we knew we were going to make it. We had about five companies try to buy us.

Speaker 2

Give me a year two and three? Are you like going backwards out the duo? Like, yes, smellan as you're leaving that office.

Speaker 7

Well, it was on paper, it was all in stock, and we didn't cash out until we went public in twenty twelve. And then we sold in twenty thirteen.

Speaker 2

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? Then did you stay on as the.

Speaker 7

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

Speaker 2

So they make you stay on for a certain period day.

Speaker 7

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

Speaker 2

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

Speaker 4

We go.

Speaker 2

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

Speaker 6

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 News Radio ten thirty And I'm Cindy Stumpo and I'm 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. There used to be three sem beats a full house. But okay, whatever, that's that. What are we had talking about?

Speaker 7

We can talk about whatever you want. We can talk 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 you to pursue technology and entrepreneurship?

Speaker 7

I would say, you know, as a little kid, I was really into the cars.

Speaker 2

Not to hold you. Do you know what if my 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 good right now. I loved cars and trucks. I bought my first car when I was twelve. I couldn't drive ecause I didn't have a license, but my brother Dan and I saved up money from a paper root and bought a Ford, a quantoline van for one hundred dollars. And if you asked me at age fifteen or sixteen. My aspiration, I might have said, to own a car wash would have been my life goal.

Speaker 3

That's different.

Speaker 7

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

pretty famous programmer. He created the video game Frogger on the Atari platform, and I remember when he was working for Parker Brothers working in that game.

Speaker 2

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. Just to learn to go to school for it is 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 liked it. My high school years were cars, girls, sports, music, 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 liked because I was a musician.

Speaker 2

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

Speaker 7

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

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

for different types of companies. I worked for the US Air Force, I worked for medical technology company, a gaming company, accounting company, and I just had a blast. I love designing things. I love designing products.

Speaker 4

That's awesome. That's an incredible way to get started. And so would you major in US? Where'd you say? God?

Speaker 7

Yeah, I went to UMAs Boston and I studied music 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 Cambridge called interly if they built publishing software. I worked for them for six years. Started as a programer. I ended up running engineering and then my last of the area in marketing, which is kind of a whole nother crazy show, because I all, yes, that was my training.

Speaker 2

And most it was self trade.

Speaker 7

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

Speaker 2

Let me ask you an honest question, did you really get that much out of going to school or did you really figure this out on your own?

Speaker 7

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

from like every country. It was crazy. They actually gave me an honorary doctorate a few years ago, and at graduation, the chancellor told me that the kids graduating that year spoke sixty one native languages as a primary language, sixty one different languages. I couldn't even name sixty one languages. So it's a very diverse school. And I like that opened my eyes to traveling, and I since it become 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 hunger to travel.

Speaker 2

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

Speaker 5

How did your education influence your approach to business?

Speaker 7

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

Speaker 2

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

Speaker 7

No, it's not. It's definitely not aiming you towards a career maybe Starbucks.

Speaker 2

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

Speaker 7

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 I did need and benefited from greatly is having some unbelievable mentors at work. So I was self taught as a programmer, got my first job as a programmer at age eighteen, and then worked with some unbelievable people and would study their code and how they design things, and how they wrote code and how they tested code and how they made code run fast. And I learned and by working.

Speaker 2

Yeah that is my producer opening up my cocine right now. If you're hearing that right that I shouldn't be drinking, go ahead.

Speaker 7

Well, so I learned from great mentors along the way. And that was really the beginning of my career was the working, not the school.

Speaker 2

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

Speaker 7

Yeah.

Speaker 2

The things that we don't do anymore. The things that 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 kids to go knock on somebody to do it because they might pull them in and hurt them and kill them and put them in.

Speaker 5

The basement of kids snow anymore.

Speaker 2

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

Speaker 7

That's tell a funny story. I used to work at a pharmacy in that I'm called Meddi mart. I don't know if they existed anymore.

Speaker 2

I was a waitress and my father's nightclub whacking it 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 dad was a workaholic, and I think I was got the work ethic from him. But one night I ate but the other.

Speaker 2

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

Speaker 7

So just to show you like the work ethic that my father, that I modeled after my father, one night I kind of over imbibed. I think it was on a Friday night. I was probably sixteen or seventeen, and I woke up Saturday with which themost unbelievable worst hangover in the world. And I called the pharmacist who was the manager, and I said, there's no way I can make it in today. And he said, do a little drinking last night. I said, yeah, maybe a little. He said,

come in, I'll fix you up. And I couldn't drive. I still was like, just not feeling well from the night. I took a taxi to work. I'm making two dollars and thirty five cents an hour and I called the taxi to bring me to work. My father was like, what are you doing. My father was always worried about spending money and saving money. But I took a taxi to work and the farmers. I still don't know to this day what he gave me. He gave me something.

He said, you cannot tell people what I gave you because I'll lose my license.

Speaker 4

Gave you.

Speaker 7

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

Speaker 6

Back, sponsored by Pillow Windows of Boston. Next Day Molding and Kennedy Carr.

Speaker 2

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

Speaker 7

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 Kayak's growth?

Speaker 7

Yeah? Boy, it was such a fun ten years of my life. One of my favorite moments was I was flying to New York. We actually Kayak was born in Connecticut and Boston. The engineers well in Boston, and our marketing team was in Connecticut and New York. So I go to New York a but once a week. And on the plane next to me there was a woman who had her laptop open and she was running Kayak.

And this is we were a year old. It's like no one knew who Kayak was, no one's using it, and I was sitting next to our watching her use it, and I'm like, this is very cool. I think that maybe people are going to find out about this because in the first year it was just me begging my high school friends, my brothers and sisters, can you please try using this product and give me feedback. But once it started taking off on its own, that was exciting.

When I found other people using it another milestone that was also really cool. At one point I forgot what year this was. But if you went to google dot com homepage and you just typed the letter K and you pause for a second, the first word that would come up, it was kayak. And that was when we were already we were growing very very rapidly. But I'm like, the day we owned a letter that was cool, Like we're the most popular K word on on Google. That

was fun. And then there's all these financial milestones. We we took a public two hundred employees, three hundred million in revenue, that's a million and a half for employee. It was. It was an incredibly fun ride, a lot of good milestones along the way.

Speaker 3

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

Speaker 7

I was on a plane. She was sitting next to me using Kayak was very very cool.

Speaker 2

And that was the first time you saw somebody that wasn't family friends on there.

Speaker 7

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

Speaker 5

Now, question, what was that feeling you had inside when you saw that.

Speaker 7

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

Speaker 5

So the next thing you know, he's going to the bathroom in the front of the plane, in the back of the way looking at people.

Speaker 2

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

Speaker 7

I was in my forties when we sold it in two thousand and thirteen. Different paths. I think I just turned just turned fifty and we sold it for two billion.

Speaker 2

Yeah, it started at forty and at fifty, did you say I'm set for life?

Speaker 7

No, this is funny. So when we were negotiating the sale of the company.

Speaker 2

Let me rephrase that. Did you take ten minutes to enjoy the high of it?

Speaker 7

What I did during the negotiation of the sale is I calculated how much money my assistant was going to make. I didn't know how much money I was going to make. I knew it was a lot, but I really she told me she wanted to buy a house, and I'm thinking, like, I got to sell this enough that she can buy a house. And I knew how much my programmers would make. I knew much my assistant made, and we had There were two hundred employees. Over half of them became millionaires that day.

Speaker 2

And that was just pump you that you're not worried about your own pocket, you're worried about what your assistant.

Speaker 7

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

Speaker 2

Well that's why I asked you if you ever had 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. They think that it means you're trying to be somebody you're not, like I'm going to be you when I'm really Cindy. Okay, that's not what impost syndrome is. You know what imposta syndrome is, right.

Speaker 7

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

Speaker 2

That's how you that's how your analogy of it and my analogy of it is when you have impostera syndrome is you don't believe like you've created this company, never earned it, that I've earned that it's your wealth and it's your brain, and some people, a lot of people go through it. A lot of my clients have gone through it, and I don't think I've ever had that. I just don't ever give myself that five minutes to say, you know that a girl every you know like you don't.

Speaker 7

I celebrated the success of the team. People were very 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 years later, I was at a party after I had left Kayak and I rented to someone who used to work there in the early years, and she said, I just have to let you know that. I mean, she was exaggerating, but she said, due to you, I paid off my house and sent my kids to college, and I paid for all of that with Kayak stock. I thought that was pretty cool. It was cool that she said it to me.

Speaker 2

When you started that company, did you think that you'd end up where you ended up with that one company if you get the other companies.

Speaker 7

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

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

Speaker 2

Deforment, why would you ever have imposted to ine that 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. But I never encountered a rich person ever until post college. Everyone around me was blue collars fury. Yeah. So the concert we were right next to Newton, we were. Yeah, you spend any time in Newton. I don't think we were allowed in there.

Speaker 2

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

Speaker 7

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 went to a friend of mine, Michael White, and I knew he had an uncle was a builder. Do you know Tom? Do you know White Construction company? JF. White Construction. So Michael's uncle Thomas J. White, He's now passed away. He was the founder of Jfhy Construction Company. And when I sold Kayak, he was eighty at the time, and I knew he had given a bunch of his money away. So I had all this money. I was afraid of it.

I want to give it away. So I met with this guy Tom White, and I said, I made all this money, I want to give it away. Who should I give it to? And he said, go to Haiti and meet my friend Paul Farmer, and then go to a homeless shelter. Meet my friend who runs a homeless shelter in Boston. Anyway, it's now twenty years later, and you look where I've given all my money away. I paid the tuition for ten thousand kids a year in Haiti.

I have forty schools and three hundred and fifty teachers, and I now do a lot of give all.

Speaker 2

Your money away most of it. You gave most of that away for half. Yeah, oh, you would have had to give half to the government anyways.

Speaker 7

Well yeah maybe right.

Speaker 2

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

Speaker 7

But then I started making more money after that too, because I sold a few more companies after.

Speaker 2

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

Speaker 7

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 on an interest, so let's call that what it was, right, and then you had to go into CDs and whatever my markets were in paying we're making a most might today and we've made in twenty years.

Speaker 7

This has been unbelievable, unbelievable.

Speaker 2

Correct sowe stock market and between you know, money market funds and everything else. But okay, so then you go and open up more companies and then you make more money.

Speaker 7

Yeah, and gave way more.

Speaker 2

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

Speaker 7

It's incredibly fun to give away money.

Speaker 2

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

Speaker 6

Right back, sponsored by new Brook Realty, Boston, would Smaller Insurance, World Auto Body and Tasca Drive Auto Body.

Speaker 2

Company and welcome back to Toughest Nails on WBC News 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 give aspiring young entrepreneurs.

Speaker 7

I think the main thing is if you look at all the jobs you could get, like maybe work for big tech company like Google, or work for a little startup or a medical company or finance company. Go interview at two or three or four or five companies, and each time you interviewed a company, try to figure out you might meet five or six people who are the two or three during that interview that you actually would end up spending your days with. And across let's see

you do with five companies. Across those five companies, which one has a stronger three percent team? Because early in your career what's really important is acceleration of skills. You want to learn as fast as possibly can. So whatever company has a stronger team, you'll learn faster and you'll develop faster.

Speaker 2

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

Speaker 4

Don't eve have high school degrees.

Speaker 2

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

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

Speaker 7

Go, I was like, oh god, a nightmare for me.

Speaker 2

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

there for kids. We need plumbers, electricians, hvac guys. And I heard mister wonderful say something last week on the news, and we all know who mister wonderful is, right from Shark NK and his advice four or five years ago was for kids to get into this this this now. His advice is get into the skilled labor, get into editing, engineering of editing, and content creator. Not being a content creator, but get like I need footage all the time to

put out for content. And that's where he's pushing and for you, for kids that know how to understand and do this, you're pushing that industry of hou.

Speaker 7

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

Speaker 2

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

Speaker 7

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

Speaker 2

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 make it. Yeah, one percent. So what is that telling you look at? I think my grandmother said the best. She died eight years ago at ninety eight years old, and she had all her faculties together at ninety seven, and she'd see my kids the last like five years, always on their phones, and she'd say, that's going to

be very very smart. Three PhDs when women didn't go to college back then, and she'd say, sinning, that's going to be the demise of your children if you if you don't control some of that, you know, pop up. Because she noticed every baby, you know, she was ninety five at that time, and everybody off for dinner and look at their phones. So isn't it crazy how technology can work in such a great way, But if you take advantage of it. It can hurt you in other ways.

You look, now, Paul, come on, we go for dinner with eight people and seven people are on their phones. Well, why are we all together? Then my son started this when he come back from school on school vacations and say, okay, we'll all go for dinner. But everybody put your phone in the middle of table. And the first person that picks up their phone, the first person I picks up their phone, he'd say, you're going to pay the bill.

Speaker 7

So what I do for my Tuesday night dinner is I bring for fourteen years of my siblings. First one to touch the phone does the dishes?

Speaker 2

Ye okay, yeah, So everybody says a but we're all addicted, right right. So but I've got clients texting me all day, all night. I got to get back to them. And every time they text me, it's like life or death, right, there's always nine to one one in my business. There's a snowstorm coming, there's a blizzard coming, there's whatever, right, And then I do get the beautiful texts that say, hey, Sinny, just want to say thank you for a beautiful home.

But those are far and few and in between, right, like you get that.

Speaker 7

I will say something really quick. Advice to young people say thank you, Yes, say thank you. Tell people you appreciate them.

Speaker 2

They don't do that.

Speaker 7

They are doing write notes, write letters. I have nephews that write.

Speaker 2

I will still do that.

Speaker 7

My nephews Matt and Mitchell each just wrote me a 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 brain is you kept that brain young in technology. So you did an age. So when you said to me you were sixty, I'm like, you show you're sixty. Like, so you've kept that brain if you was young because of technology. And I think I've kept my brain young being out there in construction, boots on the ground. And I never want to change that. Like I don't want to sit in an office and no, I'd rather be on job sites and ranton and raven and doing what

I do. But it's people like you and I can make a difference. We're just in two different worlds and businesses.

Speaker 7

Your I'm virgo, you're cancer cancer.

Speaker 2

Yeah, right, so we want to help everybody. Okay, so we know you know, we know about the dating app that you could come out. Will you stop at that one?

Speaker 7

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

Speaker 2

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 use this thing? Drivers rating?

Speaker 7

This is the driver app? Almost five four point nine six. Let's I don't do it.

Speaker 2

Let me get this, okay, you just you just get in your car and you pick people up in Uber.

Speaker 7

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

Speaker 5

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 your car a multi millionaire guy, right, millions, and you just drive some strangers around and they have no idea who you are, and you have no idea who they are. Just to get to what keep your feet on the beat.

Speaker 7

It's basically all of us should do acts of service in different ways. And let me drive someone to a medical appointment. It's a very minor thing.

Speaker 2

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 roll a freaking country one. I want to hang out with him more. I'm already feel like a better I want to do better. Already, hold on a second.

Speaker 2

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

Speaker 4

Do you ever do public speaking events? No?

Speaker 2

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

Speaker 5

So I feel like this is the movie. Now there's the TV shows are coming.

Speaker 2

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

Speaker 7

I've had only two really bad rides. When was that drug deal gone bad?

Speaker 2

No?

Speaker 7

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

Speaker 2

I were going to break. This is Citdny Stumple. You listen Toughest Nails on WBZ News Radio ten thirty. He'll be right back and welcome back to Toughest Nails on WBZ News Radio ten thirty. I'm here with Angelina Chad by Paul. Everyone knows by now, I would think after seven years on radio, I'm Sidney Stumbo. Okay, talk to me. We all know able. The dating app that is out and running right now go.

Speaker 7

The app is called LOLA. It stands for Love Language l O l A dot com and we're the best dating app in Boston.

Speaker 2

Just launch in Boston and then how do they find it again?

Speaker 7

LOLA dot com l O l A l O l A dot com.

Speaker 2

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

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