This week we will learn about Lola, a new dating app launching in Boston and New York this summer. Today's guest is Paul English the founder of six startups and co-founder of Kayak, a travel industry giant he sold to Priceline for 1.8 billion dollars. Paul is passionate about finding a better way and uses his creativity to solve problems. Years ago, when online dating himself - Paul could identify issues and became compelled to solve the frustrations many faced with existing dating apps. It was a match on Bumble with Rachel Cohen, who became his girlfriend, and now the couple is taking on a new challenge with the upcoming launch of their dating app, Lola. Through Lola, Paul and Rachel plan on creating a new way to connect. Paul shares the vision and inspiration behind Lola, and learn about the exciting possibilities that lie ahead for this new dating app.
Paul English is the founder of Boston Venture Studio and he’s also an entrepreneur, and philanthropist who has previously co-founded and successfully sold six startups – Kayak, Lola, Moonbeam, GetHuman, Boston Light, and Intermute. Paul is also the founder of four nonprofits – Summits Education in Haiti, Embrace Boston, The Winter Walk for Homelessness, and The Bipolar Social Club. Paul is the subject of Tracy Kidder's book "A Truck Full of Money" and you can hear an interview with Paul on "How I Built This" with Guy Raz and view his video from TEDxBoston in 2022. I’ve watched and listened to it all and I can’t tell you how special this man is!
Kerry Brett and Paul English discuss the common struggles many have with online dating and how Paul plans on changing the online dating culture and improve and simplify the over dating experience.
How Lola will filter out terrible daters.
How Lola will use A1 to give the users better matches.
Lola will be very safe for women.
Lola will have a component built into the app that will find a place in the middle for you to meet.
How Lola will use machine learning to help find you a better date.
Lola will cut down catfishing.
Lola will filter out people who don't practice good behavior.
This week we will learn about Lola, a new dating app launching in Boston and New York this summer. Today's guest is Paul English the founder of six startups and co-founder of Kayak, a travel industry giant he sold to Priceline for 1.8 billion dollars. Paul is passionate about finding a better way and uses his creativity to solve problems. Years ago, when online dating himself - Paul could identify issues and became compelled to solve the frustrations many faced with existing dating apps. It was a match on Bumble with Rachel Cohen, who became his girlfriend, and now the couple is taking on a new challenge with the upcoming launch of their dating app, Lola. Through Lola, Paul and Rachel plan on creating a new way to connect. Paul shares the vision and inspiration behind Lola, and learn about the exciting possibilities that lie ahead for this new dating app.
Paul English is the founder of Boston Venture Studio and he’s also an entrepreneur, and philanthropist who has previously co-founded and successfully sold six startups – Kayak, Lola, Moonbeam, GetHuman, Boston Light, and Intermute. Paul is also the founder of four nonprofits – Summits Education in Haiti, Embrace Boston, The Winter Walk for Homelessness, and The Bipolar Social Club. Paul is the subject of Tracy Kidder's book "A Truck Full of Money" and you can hear an interview with Paul on "How I Built This" with Guy Raz and view his video from TEDxBoston in 2022. I’ve watched and listened to it all and I can’t tell you how special this man is!
Kerry Brett and Paul English discuss the common struggles many have with online dating and how Paul plans on changing the online dating culture and improve and simplify the over dating experience.
How Lola will filter out terrible daters.
How Lola will use A1 to give the users better matches.
Lola will be very safe for women.
Lola will have a component built into the app that will find a place in the middle for you to meet.
How Lola will use machine learning to help find you a better date.
Lola will cut down catfishing.
Lola will filter out people who don't practice good behavior.
I'm Carrie Brett and this is Shot At Love. This week we'll learn all about Lola, a new dating app launching in Boston in New York this summer. Today's guest is Paul English, the founder of six Startups and co-founder of Kayak, a travel industry giant. He sold the price line for 1.8 billion. Paul is passionate about finding a better way and he uses his creativity to solve problems. Years ago when online dating himself, Paul could identify issues and became compelled to solve the frustrations. Many faced with existing dating apps. It was a match on Bumble with Rachel Cohen who became his girlfriend, and now the couple is taking on a new challenge with the upcoming launch of their dating app. Lola through Lola, Paul and Rachel plan on creating a new way to connect. Stay tuned as Paul shares the vision and inspiration behind Lola and learn about the exciting possibilities that lie ahead for this new dating app. Paul English is the founder of Boston Venture Studio and he's also an entrepreneur and philanthropist who has previously co-founded and successfully sold six startups. Kayak, Lola Moonbeam GetHuman, Boston Light and InterMune. Paul is also the founder of four nonprofits Summit's education in Haiti, embrace Boston, the Winter Walk for Homelessness and the Bipolar Social Club. Paul is the subject of Tracy Kidder's book, A Truck Full of Money and you can hear an interview with Paul on how I built this with Guy Raz and see his video from TEDx Boston in 2022. I've watched and listened to it all and I can't tell you how special this man is. In this episode, Paul English will dive deep into all things dating and share his inspiring journey and amazing story is my honor to welcome Paul English. Hi Paul.
Speaker 2:Hi. Great to speak with you.
Speaker 1:So great to have you here today. I absolutely love your story. It is so inspiring. Now you went to the oldest public high school in the country and I love that you hacked your teacher's computer from the Computer lab<laugh>. Mm-hmm<affirmative>. I love hearing about your background and how you started in this industry and I think it's kind of telling that your first product was called Cupid.
Speaker 2:Oh, that is true.<laugh>. I didn't make that connection to what we're talking about today, but that's actually very, very funny.
Speaker 1:I think it's really wonderful that you're starting a dating app and I'm excited for your new chapter and I'm excited that you can help people find love. But before we talk about your dating app, I wanna talk about growing up Irish Catholic and we both worked full-time and went to school nights at UMass Boston and it both, it took both of us five years to graduate. And I was working at the time at The Improper and you were doing way bigger things. But I think it's interesting that that time in our life, the world had changed and you could make money through advertising, which was how the improper was built. It was a free publication and you were really sparked by your passion for programming. Take us back to the beginning of your
Speaker 2:Career. Let me see. My mom, she bought a computer for the family when I probably was about 12 or 13 and I kind of took it over. I just became obsessed with it. I read the manual front to back and learned how to program at that point it was in a language called Basic, which is a very, by its name, very simple language. And I started writing software for this computer. Um, ultimately developing my own games, one of which, as you mentioned, I named Cupid while I was in high school. I sold it for$25,000. So I was like psyched just to learn that, you know, programming computers, which I viewed as a hobby that if you're good at it you can actually make money as well. So that's the first time I made money is selling My Game Cupid while I was still in high school.
Speaker 1:And you kept learning and improving. And where did you go before Boston Light?
Speaker 2:When I um, graduated Boston Latin, I went to UMass Boston for college and I worked full-time or almost full-time as a programmer for the five years I was there. And I took classes in the afternoons and evenings and I did everything from working for the US Air Force. I installed software on spy planes. I worked for an accounting company and rewrote other accounting software. I worked for a computer company called Data General. I did operations research for them and I worked for medical device companies. So I would kind of switch industries every year, a year and a half just to learn as much as I could while I was going to school.
Speaker 1:You start to develop this company Boston Light, and you really only have the one client, the Boston Globe<laugh>.
Speaker 2:That's right.
Speaker 1:So there's this Boston Globe connection, which I think is amazing cuz my dad worked at the Globe for 55 years and the Boston Globe is right across the street from UMass Boston. You get this great opportunity with the Boston Globe and tell the story about how things are moving really fast and you think that there's an opportunity that you're able to sell this. That's a really interesting story.
Speaker 2:The funny thing about the Globe contract that my team won and we delivered on is how I met the Globe. Mm-hmm<affirmative>. I actually have a friend named Mike White and he called me up one day and said, will you be fourth for golf? And I said, I don't know how to play golf. I've never golfed in my life before. He said, it doesn't matter, it's called scramble. It's um, best ball is the ball you use for the next hole and whatever. Explain the rules to me. One of the other guys in our foursome didn't show up and I saw a guy in the pro shop with a boston.com hat and I said, do you wanna play golf with us? And he said, sure, I'd love to. And so we started playing golf. His name is Lincoln Millstein and I said, where'd you get the boston.com hat? He said, I work there. I said, what do you do? He said, I run it. I said, oh my God, I have opinions about your website. I mean, I grew up in Boston. I used to deliver the Boston Globe and I really think it's amazing you own that domain name boston.com, but I think you could do a much better job at being, you know, local media for the community. And over the course of a couple hours, I must have gave him like 25 ideas of different things I could do on the site. At the end of the game, he gave me his business card. He said, will you come in to see me and the publisher? So I went in a couple days later to meet him and the publisher and they actually offered me a job as cto, chief Technical Officer of the Globe, which I couldn't see myself like doing that, working for a newspaper as like my day job. Mm-hmm.<affirmative>. But I said I, I won't take a CTO job. However what I will do is I'll design apps for you. So the first app I'll design for you is anyone who advertises in the globe, we will sell their products on boss.com. We build a shopping cart, a checkout system, secure a payment and all that. And this is back in 1998 when it was still pretty new e-commerce selling on the internet. Mm-hmm.<affirmative>. So we got that contract for them. It was only for$50,000, but that was enough that I could start hiring some engineers. And so I called two or three of the desk engineers I'd ever worked with and said, Hey, I got this contract with the Boston Globe, can you help me build it? And then we were kind of off to the races after we had worked with the Boston Globe, we then got a big contact with Intuit, started working with them and ultimately in about a year we sold the company to Intuit. And I then served as VP technology for them.
Speaker 1:Wow. So you have no idea what to sell it for. And you think like maybe 20 million and you call a friend and he tells you ask for 40 million.
Speaker 2:Yeah. It's kind of crazy that even 20 million sounds ridiculous for a company which is one year old and has very little revenue. But this was the beginning of the.com. The first.com and companies, internet companies with strong internet teams are selling for crazy money. I knew about some other companies that had sold some other startups in e-commerce space and I said, okay, I think we're as good as those companies. I'm gonna ask for 20 million. I think it's like really, really brash. The night before I called my friend Fred Eagan who um, I'd worked with at a prior company and I said, Hey, in the middle of negotiating some the company to Intuit any tips for me? Cause he had just sold the company to Yahoo and his first question was, how much are you gonna ask for? I said, 20. He said, ask for 40. I said 40. That seems crazy. We're like a year old. He goes, trust me, ask for 40. I got him a call and it was their head of corp dev for Intuit. And so finally we're you know, kind of beating around the bush. And then she said, all right, how much do you think your company is worth? I said, 40 million. And she literally said, you and she hung up on me. Mm-hmm.<affirmative><laugh>. Yeah. Which I thought was not a good sign. Right, right. But um, uh, but she's a very aggressive negotiator. Really good. Yeah. But she called me back Uhhuh and she said, come on, really? Tell me what you think you're worth. Anyway, we ended up negotiating. We sold it for 33 and a half million dollars. Amazing. You know, when I told my dad the next day that I had sold a company for 30 million, he said to me, how did you do that? Like how did, how'd you come up with that number? Where'd you find the lawyer that negotiated it? And I said, no, dad, I negotiated it. I didn't use any lawyers. And he said, how'd you learn how to do that? I said, dad, I went to garage sales with you every weekend and watched you negotiate like buying and selling air conditioners. I did the same techniques except I just added some zeros. Wow. And he liked that story.
Speaker 1:I know when I heard that story, I listened to your book on Audible, that book about your life. And I wanted to cheer. I really, I didn't know who I was happy for in that moment for you or your dad. And it was just such a beautiful story that got the gifts from him that made you successful in that sale. And as a father, he must have been so proud of you. And I like how they wrote in the book that he was like so fearful. He knew that your life had changed. I wanna talk about this chance meeting that you had with the co-founder and how you had this lucky opportunity to meet with Steve Hafner. I think it's so fascinating how this deal basically came together in 45 minutes.
Speaker 2:I had um, sold my company to Intuit. I worked for them for four years and then my mom had passed away and left me in charge of my dad. My dad had dementia, which turned into Alzheimer's. And so at some point he um, started needing more and more care. So I quit my job at Intuit to take care of my dad. And I had a lot of help, particularly from my sisters. But I had to um, you know, feed him two or three times a day and drive to all his appointments and all that stuff. Eventually my dad passed away like a year and a half later. At that point, I still had all this money from Intuit. I felt uncomfortable having all this money because I grew up with no money. Mm-hmm.<affirmative>. And I wanted to give the money away. And I called a friend of mine, Mike White, who I mentioned earlier, his uncle was involved with some philanthropy in Boston. So I called up this guy Thomas T. White and said, I made all this money, what should I do with it? And he said, you should go meet my friend Dr. Paul Farmer in Haiti and then you should go meet my friend who runs the homeless shelter. So anyway, I went to Haiti to meet Paul Farmer Do. I saw some amazing things but also some very sad things. So I came back and when I landed at Logan in Boston, I said, I need to start another company. I need to make an obscene amount of money so I can, can give a lot more money away than I had made. So I called a friend of mine, bill Kaiser, who was a venture capitalist at Greylock. I met him through Bill Warner. So I went to meet Bill Kaiser and I said, I wanna start another company. He said, start tomorrow at Greylock as an office for you. We have an assistant who can help you. We'll have you look at companies for us. So I started there and started looking at companies for them as I thought about what I wanted to do next. And then one day, another venture capitalist, Larry Bond at General Catalyst asked me if I'd come over and look at a company for him. So I went over to his company in Harvard Square and had the meeting and as I was leaving, one of the partners said, oh, there's a guy here named Steve Hoffner. He's one of the founders of Orbits and he wants to start a travel company. He's looking for a cto. Will you meet him? I said, sure. So he introduced me to Steve. We went down to legal seafood. I think we had two or maybe three gene tonics over like a 45 minute period. He gave me the pitch. He basically said, we want to create a search engine for travel where you don't buy anything, you just search and when you want something you click the link and go off directly to American Airlines and buy it there. I said, I think it's a really good idea. We kind of brainstormed about it and he said, I'm looking for cto, you know, for the company. And I said, what are you paying? And he said, A buck 50 and 4%, meaning$150,000 and 4% of the company. I said, that sounds amazing. I run a group called Boston cto, it's all the top CTOs in Boston. I can find someone for you. And he said, why don't you do it? I said, no, I sold my last company. I wanna create my own company again. And he said, what would it take to have you do it? And I said, I don't know. At a minimum 50 50. Mm-hmm<affirmative>. And he stuck his hand out and he shook my hand. He said, we're in. And we went back up to Gen General Catalyst to talk to the partner Joel Cutler. Joel said, how did it go? And Steve said, the good news is I have a co-founder and we put a million dollars in tomorrow, which he kind of neglected to tell me that during lunch. Mm. But uh, and he said, and I'm tearing up the term sheet because now I'd have a co-founder worth a lot more money. And I think he was joking around with Joel. But anyway, that was the beginning of the business relationship and the friendship. And we worked together for 10 years at Kayak after we took it public and then sold it, I left. Steve is still there, but we still hang out all the time.
Speaker 1:It's amazing that story in itself is crazy. And how you, the two of you guys within that 45 minutes have this new company Kayak and you went from being a little boy who delivered on your bike the Boston Globe, to being on the front of the Boston Globe when you sold Kayak to Priceline. It really is an amazing story and I love how you put your fortune to all these foundations that you've started. And I think your charitable nature is the best thing about you. And I love that you're so driven to help others. Another great strength, strength that you have is you're a quick judge of character. Can you tell me why this has served you well?
Speaker 2:Yeah, I think um, the most important skill that we have to develop as entrepreneurs is recruiting. Trying to find the people to work with you, to build your company or to build your nonprofit. As I built my first company, I started studying recruiting. I've read a run bunch of books, I've read some blogs and I would talk to people all the time about like, how do you find people and how do you recruit? And I just always tried to get better and better at it. And one of the first things I did was I tried to get the candidates really excited. So I would do things like train my team to say, when someone shows up, you know, make eye contact, introduce yourself, ask'em if they wanted a drink. I also learned back then I was studying, I was just starting to study diversity issues. And I read somewhere that when black prospects walkinton office with the white people, the white people don't make eye contact with them, which sounded like awful. Mm-hmm<affirmative>, I gave people that little tidbit and said, you know, no matter what the person looks like, make eye contact. Say hello. So I did a lot of things in terms of trying to get the candidate excited in terms of the way we would interview them and then also develop some techniques about what type of questions I would ask them. And I didn't want to be like a banker on the other side of the desk like I'm gonna decide your f your future, yes or no. Mm-hmm<affirmative>, it was more like a collaboration between me and the prospect. Like, do we like each other? Is it my company's alike? Is it we're trying, I'd like to hear about you and just really a conversation, but to learn how to direct the conversation a little bit in a way that you can evaluate the person, not just on can they do the job you're gonna hire'em to do, but what would they be like as a teammate? Mm-hmm.<affirmative> and I have honed those skills over the years and every time I made a mistake in hiring, I would meet back with the interview team and said, how could we have figured out sooner that this person wasn't a fit for that job at that time? I'm a big fan of continuous learning and always trying to get better at anything you think is important. And hiring is just the number one thing for me in creating companies is how do you get that magical team? I've always said that magical teams create magical products. Mm-hmm.<affirmative>, if you can get the team that kind of has the mojo that like really enjoys working together and works hard, that team will build a company.
Speaker 1:Trust is huge. That's one of your things. Like you wanna be able to trust all the people that you hired with your life really. And they're loyal, they're fiercely loyal to you. That's huge. I mean that was definitely part of your success. But in the book they talk about you moving at lightning speed to create all the things that you have created. You have to operate fast and make decisions fast. But then you have this laser focus when you see talent when it comes to recruiting and, and your coworkers used to joke with you and say, wh when you would travel, they'd say, well who did you hire on the the plane<laugh>.
Speaker 2:Yeah.
Speaker 1:I think even though you would like in your mind sometimes blow past people, you also had this ability to be open and find really talented and amazing people. You've got something that is a hyper focus when it comes around recruiting.
Speaker 2:I like meeting new people. I took a My Briggs test years ago and I pegged right in the middle between introvert and extrovert. I'm probably a little bit on the spectrum. I can be socially awkward at times, but I like meeting people particularly one-on-one. Mm-hmm<affirmative>. A few years ago I started driving for Uber to do some research but also as a way to meet people. And I really enjoyed it. And you know, when you think about meeting people for your company or your nonprofit, if you're trying to build a nonprofit in some ways there is some similarity with dating and meeting someone for the first time. And there's some similar things you want to do from when you're dating on a first date as well as meeting someone as a perspective employee. You know, you wanna make sure that you're be yourself, be genuine, be honest, pay attention to them, be focused on them, show high energy, talk about things that are important and have fun. And those rules kind of guide me on first dates, but also first business meetings.
Speaker 1:How great would it be to find the love of your life, the man of your dreams. Do you believe online dating would work if you had the right tools to be successful? Well I have exciting news. I've created your best shot at Love Masterclass. I cannot wait to share with you what's worked for me in my life and for many of my clients that have helped over the years. If you enroll in this class, you have a winning mindset and believe in getting help before you start something new. If you're ready to see changes in your dating life and wanna take action, check out my free webinar@shotatlove.com. If you decide you're going to choose another path that you're worth it and you're willing to enroll in the masterclass, you can also register@shotatlove.co. I designed this masterclass specifically for you to be successful. Please know that everything you're going to learn in these nine modules and six coaching calls has been carefully curated for you so you can gain the success you truly want. I will be there for you the whole time. In the meantime, I wish you all the success and I can't wait to hear about your story of Finding Love. I'm Carrie Brett and I will be your mentor and friend through this incredible journey. I have that ability too. I think I'm a good judge of character as well and I have to figure out people very fast because I had to shoot covers in 10 minutes or less sometimes. And yeah, I had basically worked for events for you through our mutual friend AJ and I. I must have not been able to get your attention in that moment either. It was just a busy event or whatever. But how we started talking was so funny to me because my friend Linda Holiday had asked your girlfriend, how'd you two meet? And she said, oh, a dating app. And I turned around and said, did someone say a dating app? And you just lit right up because we could see instantly that we both had this passion around online dating. So when you do have a similar interest and it's true and the intent is, is there, then it's easy to strike up a conversation. But it can happen in such a random way sometimes. But I think it's important to be open. You never know who you can meet and where you can meet somebody. You met Rachel on Bumba and what happened to you on online? What did you learn about yourself or the process of online dating?
Speaker 2:A lot of people hate the dating apps. Dating is a numbers game in that the more people you meet the more likely you're gonna find someone that's compatible with you. You know, I can't imagine living a hundred years ago where you met the people in your village and that was it. With the apps you can meet people from all over the place, different backgrounds. I like the apps, the way to meet someone new. There are some things which are frustrating about it. I'm creating this app with my girlfriend with Rachel. The original idea came from her. But the first thing Rachel and I did, we talked about creating an app together, is we did a survey, we got 200 people told us about themselves and about what apps they use and about what they hate about online dating. And there were maybe 10 or 12 themes that came across when you read all 200 surveys about things people didn't like. There were two that really rose to the top. One is people said they can't stand the amount of time it takes to use the dating apps. Mm-hmm<affirmative> and all the chatting and ghosting and just too much chatting and not enough dating. And then the second thing is they would meet someone on the app, they'd chat, they'd arrange time to meet, they'd meet them and they, they often would go really poorly and it'd say, why did it match you with that person? Like, that person was terrible, it was not a match for me. And so what we wanna do for our new app, which we're calling Lola, l o l a. And by the way, in the past one of my six companies was called Lola Travel, but when I sold that to Capital One I kind of kept the name. So we owned lola.com and the new company's gonna be called Lola dating, it's l o l a like love language. And we're gonna focus on people who actually want to go out in the this week for to dates. And also I'm getting feedback on how the date went so we can better match you with people that we think will have the things that you want. I think we're gonna be the first app. That one is very, very focused on don't use the app unless you're ready to go out. So if you have a clients coming in and you're working, you know, 8:00 AM to 10:00 PM every night this week, please don't use Lola cuz only use us when you're ready to go out. The second thing is getting feedback about how the dates went. And we're literally gonna kick people off the platform if they get rated really poorly by a lot of people. We don't want them on the platform cuz we'll miss our promise of getting people great dates.
Speaker 1:<laugh>. That's okay. So this goes back to you driving how do you rate people? That's why you drive an Uber because you wanted to feel what rating felt like. So you don't want a bunch of people who are like time oysters I guess, right? That's right. If you're a busy person and you don't plan on going out right away, please don't use Lola. I actually kind of like this, like you're already setting up boundaries and you're making it challenging. We only want serious people here. Tell me a little bit more about that. If you wanna go out and date on Monday, are there people who are gonna go on and be able to go out that Monday if they log on on a Monday?
Speaker 2:That's the first idea is you tell us when you want to go out and we'll show you other people that want to go out on Monday night. So we'll eliminate the back and forth about when are you free? Cuz you can just tell us right up front. Um, even tonight if you want to go out somewhere tonight, we'll find someone else who really wants to go out tonight. So very focused on people who actually want to go out on dates. That's kind of the first thing. And the second thing is getting really good feedback from the date is about how the date went and we have like three or four questions we ask about each date and we use those both to train the system to get you better and better dates. Each date will be better than the last one. And then also frankly again we kick people off the platform that are like terrible daters.
Speaker 1:Can you gimme an example of terrible daters? There are a lot of people who just use the dating apps to avoid feeling lonely and they do it to have an accom, like an ego boost.
Speaker 2:Yeah, I mean the first thing is when you match someone on Lola, you're expected to go out with'em. And if you match with let's say five people or 10 people and you've literally matched, you said you know I like you, you like me, we're matched, shows are matched. Now let's talk. If you match with 10 people but you don't go out with any of them, we're gonna kick you off the platform because we're for people who want to go on dates And if you match with 10 people and you won't go with any of them, you shouldn't be using Lola, you should go use Tinder or something. Cuz those people want to go on dates. The second thing is, you know one of the concerns we got from a lot of women we interviewed was they sometimes worry about they don't feel safe on dates. Sometimes we have three or four questions we ask after every date and one of the questions is, did you feel safe? And if someone got marked by a bunch of people who didn't feel safe with'em, we kick'em off the platform. Now if it's just one person, maybe that it was just a bad chemistry and one person is spiteful, wants to mark someone really negatively, but if a bunch of people mark you as unsafe, you're gonna be kicked off Lola.
Speaker 1:Yeah, I agree. Because Tinder began with young people. People thought it was a hookup site. I like that you're starting it with saying it's a place where women are going to feel safe and if you bring the women, you'll bring the men<laugh>. So with Lola you'll cut down the texting time. So will it be something that you say, okay, I matched with you now it's gonna move right into let's meet for a drink or something.
Speaker 2:Yeah, I mean the thing is if you say you wanna go up Monday night and we show you someone you match with for Monday night, the plan is okay, where do you wanna meet? And eventually we're gonna actually recommend the restaurant and we'll find a place convening for both of you and even make a reservation for you. So we can make that more efficient as well. You
Speaker 1:Have created apps in the past because you wanted them, you didn't set them up to be a company, you set them up to help make your life simpler. One of those apps would find a place in between to meet somebody in an area that you didn't know as well. So can you talk about that app that you created and will it potentially be included in Lola?
Speaker 2:Yeah, so I'm running, um, I've sold six companies now. I've also created the four nonprofits. After I sold my last company, I opened up a startup studio called Boston Venture Studio. It's bbbs a bbbs.net and we have five like real companies under development. But in addition to running these companies a building, these companies, we also occasionally bump into a problem that is a problem for us. We don't find a good app to solve it. So we'll like crank out an app and we do these just for fun to hand out a free utility that we publish with source code. One of them is called middle.net and the basic idea is if you're in the south end of Boston and I'm and Cambridge and we want to meet for dinner, you just go to middle.net. It plugs in both addresses and it picks a restaurant right in the middle of us to go meet. And why didn't anyone else ever build that? Like why is that in Google Maps? I don't know. So we built it, we're gonna build that feature into Lola. So if you and your date wanted place to meet, you can click a button and an app saying finest a place and we'll find a place that's roughly in the middle that's convenient for both of you. There's a bunch of other fun apps we created as well. We have an app called Fun Contact and the idea for that one is if you meet someone at a bar at a conference anywhere and you want to give me a number, it's amazing how difficult it is. You have to like type in your, that you say your number out loud, they type it into your phone. If you, you know, if you're an iPhone and they have an iPhone, you can text your contact to them but then you need their number to text it to them. But so what Fun Contact does is it just sh you open the app, it just shows a QR code when the person scans it, they get all your details immediately, just some scanning your QR code. We have an app for TV recommendations, restaurant recommendations. We're building a bot generator to develop an AI bot of yourself. AI is a broad term. There's a lot of definitions for the word ai. I mean at a highest level AI just means software, which that looks like, like it's a human doing the work, but it's really software. It's like software that thinks the way a human thinks. There's different fields of AI that will stop tech over the last 10 years is just called machine learning, which is you look at a lot of data and you find patterns that sometimes a human can't find but the machine can detect patterns. And so for dating we're gonna look at how you get feedback on people you meet and we're gonna pour through their profiles, all their data, all your data and we're gonna try to predict who would be a good date for you. Interesting. So we're using a field of AI called machine learning and it's a very common technique that most big tech companies are all doing machine learning right now and we're using it to help find you a better date.
Speaker 1:No, you've built a lot of companies and you've dealt with a lot of competition before. Do you worry that there are already a lot of existing dating apps?
Speaker 2:Not at all. Like when Steve and I created Kayak, there were a lot of company travel companies at the time doing things similar to us in some ways. Some who had predated Kayak and even like Expedia who was the market leave at the time back in 2004, people would say to me, Expedia spends a billion a year just in brand. Like not even demand generation but just in brand. How can five guys with a PowerPoint deck, how can you think you can compete against, you know, multi-billion dollar company? I've always said, and I'm sorry this is gonna sound a little bit arrogant, but this will just speak to the fact of how focused I am on recruiting. Mm-hmm<affirmative>, I said Expedia, you know, they might have 2000 people in engineering and I only have 10, but they only have 10 of the 10 smartest people. So in that 2000 people there's only 10 of them that are the 10 smartest at Expedia. I'll put my 10 against that 10. And I think we can innovate faster and the way one company beats another one is you have a better team and you try stuff more rapidly. You try it, it doesn't work, try it, it doesn't work, try it doesn't work. You go through really, really rapid cycles and if you have a really good team and you're extremely customer focused, you'll eventually figure it out. And we eventually did figure out at Kayak, I think the first release of Kayak was terrible and we got out really negative feedback from customers over time. The more time we spent with customers, the more iterations we tried. Eventually we got it right and then the app started growing like crazy.
Speaker 1:I think you can really grassroot it and grow it very fast in Boston. You have a mind where you create clubs and culture that I think you would be the perfect person to do this.
Speaker 2:Yeah, I mean I grew up here so I'm very loyal to the city and um, went to school here. I've created all my companies in Boston. I know the scene here. I know like the hot restaurants where people hang out. Um, I have friends from different communities in Boston, so I go out all over the city. Mm-hmm<affirmative>, I love Boston as a test market because it's small. There's only 600,000 people who live in Boston proper. I mean when you include like Eastern Mass it grows to five or 6 million. But in Boston proper there's only 600,000 people. And if you wanna spread an app, um, and you want to have, if you look at, you know, what percent of those people are single and then what percent of those people can you get to learn about the app, it's doable. You know, and you can think of all these like marketing stunts to try to build in little viral features to get your first 10 users to get another 10 users. A market like Boston just allows you to dream. Like, I want to take over this city, I want every single person in Boston going to lola.com choose our app
Speaker 1:And you could do it.
Speaker 2:Yeah.
Speaker 1:Because everybody knows everybody here,<laugh> and most people are from here and stay here. It's changed a little bit, but you could even work just the college campuses. That would be amazing because it's such a college town. How do you feel given your background in tech that you can improve online dating?
Speaker 2:Yeah, so with each of my companies, um, I'm a programmer by training but I haven't really been writing code recently. I focus more on design, uh, the user experience at UX as we call it the industry. And with each app that I design, I try to make it simpler than the last app. Like I want every app to be so simple that you just understand it. You don't need anyone to explain how it works. You just can figure it out by clicking and scrolling and just seeing what the next step is to do. And so I want to take that, those decades of experience I have in UX and turn it to dating. Can we build an app that's simpler to use than other dating apps? And that's what we aspire to do. Like we're not gonna build something that's crazy different because there are certain patterns mm-hmm.<affirmative> and there are certain things that work that people have been trained, you know, across Tinder and Bumble and Hinge and all the other ones. So it'll look familiar to be abusing dating apps, but hopefully we'll do something that'll be fun and fresh and just really enjoyable. And then the most important thing is we're gonna get you great dates. We're gonna get you someone who also wants to go out and someone who behaves well on a date and someone that is going to show you a good time. I love
Speaker 1:That. That's really good. And the other thing aside from your programming background is you really focus on people, the culture, client relations, and you are a branding expert. You're fascinated with names and you collect books and books of ideas, uh, for products. And I think you have like 300 domains that you pay into you. You have a good knack for things that work and are going to be well received. And it will be interesting to see how you put your spin on this new dating app. I'm excited to see that
Speaker 2:And I'm excited to build it. We're having a blast. It's also been fun for Rachel and I to work together on this. Um, because as you mentioned earlier, she and I met on a dating app and now what we're trying to do is say, how can we make it better? Like we actually both liked Bumble, we thought it was a pretty good app and I'd like somebody of that apps out there as well. But we wanna do something that's simpler and gets you out on more dates where you can meet nicer people.
Speaker 1:That's great. Anything that Rachel is important to her.
Speaker 2:So the things that's important to her is safety. Cutting down on catfishing where someone doesn't match their profile. Cutting down on people that are jerks on dates, like arrogant people that just aren't very courteous at all. We're gonna filter all those people out.
Speaker 1:That's
Speaker 2:Good. We're literally gonna kick people off the platform. We might even get their money back. Just say, you know what? We don't want your money. And if we have to cut out 20% of people off our platform, you might say that cuts our revenue by 20%. But in fact I think most people say, you know what, I want an app where all the people on it are kind and fun and polite.
Speaker 1:I agree. And if it works, they'll pay whatever<laugh>. Yeah. You know, I mean I think people are desperate for something that works for them and I like that. You want it to be a bunch of nice people. I've always said this about dating apps that I do think collectively the world is good. It's a few bad apples that give online dating a bad name.
Speaker 2:Yeah, exactly.
Speaker 1:From the beginning with the first thing you invented, which is Cupid. I think you somehow have this law of attraction dialed in within your personality that I don't think you realize. And recently you celebrated your third anniversary with Rachel on your first date you were out to dinner and you sat next to Anna Winter and Bradley Cooper, and then three years later you returned to the same restaurant to celebrate your anniversary. And who was sitting next to you again?<laugh>.
Speaker 2:Yeah. Yeah. It was pretty cool. Don't
Speaker 1:You think there's something to that though?
Speaker 2:No, I definitely have had enormous luck in my life. Mm-hmm.<affirmative>. But they say that, um, in terms of like creating companies on average, everyone's gonna get a little bit of luck, but the people who are best prepared and when that luck happens, can leverage it and make something happen of it. So I try to recruit teams that are good at turning luck into opportunity than when something goes your way that you can capitalize them on it and win more customers and hire better employees and everything else. Need you to make a company successful.
Speaker 1:Closing, where can we find and follow Lola and what is this rollout in launch? What will it look
Speaker 2:Like? So we're launching it this summer in Boston and New York. If you wanna sign up to get an email when the app is released, just go to lolo.com. L o l a.com. Where
Speaker 1:Can people find you on social media as
Speaker 2:Well? My Twitter and Instagram is English Paul M like Michael English Paul m Well
Speaker 1:This is going to be so exciting to see how this happened and I'm really excited for you and I'm so grateful that you came on Shot at Love today and shared with us this exciting news.
Speaker 2:Thank you so much.
Speaker 1:And for now, this week shot at Love Dating tips inspired by our guests, entrepreneur, founder, and philanthropist Paul English. Number one, become a master recruiting just like Paul English. Look people in the eye and be interested in what they say. You may have more in common than you think and you never know what incredible people you may meet. Number two, if you wanna change your life, build a better team around you because your success and happiness have much to do with the five people you surround yourself with. Number three, keep an eye up for the launch of Lola in Boston and New York this summer and get serious about going out and meeting new amazing people. I hope you found some of my tips helpful this week. This is what Shot at Love is here for, to help you find love, keep up the commitment to yourself and commit by helping someone else by sharing this podcast. Stay safe and stay tuned for more episodes. And if you like this show, please subscribe and leave a five star review. I'm Carrie Brett and we'll see you next time.