719: An Ambitious Entrepreneur’s Guide to Dating In Your League

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25:19I love that and you know to me it honestly makes sense of like you need to have skin in the game right like I don't want you to just like create an app pop up a photo because you're traveling and you're scooting through I want to see that you're actually like driven and tire kickers because I'm I can't, I mean, first off, I can't imagine dating. I, my husband was basically like my first serious boyfriend. So that's that. But when I think about, I know when I think about like time and especially for our listeners, like for people that are in interested in gold digger, like they are ambitious people, right?

25:57They're driven people. They're people who are willing to do the work. And one thing I'm curious about is have you noticed anything? Because when I think about my audience and the people who are likely single in it, they're also in that stage of building something. Right. And like so much sacrifice comes when you're saying, I'm not going this way. I'm going to go that way. And I think about, you know, I've been an entrepreneur for over a decade, but there were many years where like relationships were kind of on the back burner while I was building. And so have you found like with the app that a lot of people are now kind of like lifting their eyes and being like, okay, I am ready to like put in the time and commitment for relationship.

26:35Or they're also like, I don't have a lot of time to mess around. So I want to be super intentional about the relationships that I'm pursuing so that I'm not wasting my time. No, it's a great point. And I also was building my company while, you know, the irony was my company was a dating company. So it's very meta, but, but I empathize with that sentiment that you feel like you're either, if you're not building, you're sacrificing that. But then if you're dating, you should be building. And so you're constantly kind of pulled in, in both directions. And that was one of the reasons I built the league was that I didn't want, I wanted it to be like very fast and efficient.

27:10Like I was valuing my time super high. I mean, I was in 200K of debt after business school. I was like, I need to get out of this. I want to at least make this business self-sustaining so I can like sleep at night and know that I can pay everybody going forward. And so I really tried to make the league where you go in, you only really have to be in there like a minute or two, you get your three matches a day, five matches, depending on, you know, if you, if you pay, you get more, but for the most part, it's a set number of profiles per day. It's small in number, but high in quality. It's, you know, we believe in quality over quantity.

27:41They should be like highly targeted for your preferences. We don't show you people where you don't fit their preferences. So let's say, you know, you're out a lot of times dating apps will just show you who you want to see, but even if you're not necessarily a fit for, for them and their preferences, and they kind of, It's almost like false advertising in a way. And so we don't do that. We only show you people where both preferences are met. So that's already like a much narrower kind of pool of candidates, if you will. I call them candidates sometimes. And then I think, you know, the trick of dating while you're working, I think, you know, everybody needs balance.

28:14And I personally had a couple different relationships during the league. I would say that they were all strained because of my commitment to work. And it was always like the league was first and then the relationship was second. And I'll be the first to admit, I did not prioritize, you know, my boyfriends at the time above my commitment to getting this company into like, you know, to profitability and to being self-sustaining. But I think part of what was great about the league is that the people on the league understood that. And a lot of times they were building their own stuff. And so maybe, you know, maybe they were actually okay with not getting as much time with me.

28:48We kind of had that expectation going in. And so I think it's almost like if both people are aware that their priorities are, you know, there's multiple competing priorities. And I think it can work. It's only when you have that misalignment of expectations. And I think the ethos of the league is like people are trying to build empires. People are working their butt off. This is a like very career focused crowd. And so I think people are attracted to that. And that's what I saw at business school was that people were attracted to that. And these couples would just form out of our business school pool of like 300.

29:19I think we had over like 10 or 15 couples that formed, which is pretty high if you think about it. And so it's like basically ambition attracts ambition. And that was kind of where I landed is that like, I needed to find someone that wanted, kind of wanted that ambition and was okay, sacrificing maybe as much time as another relationship they would have if the person wasn't so, so career focused. So, so yeah, I guess my answer to that is like, I think it's just being, being clear about your expectations up front with people that how much time you really think you have to give. And you can always give more time, but I always say like set expectations low, right.

29:53And you can always over deliver. And you can also screen out people that like want to come with girlfriend or I called it, you know, a dot, a doting like girlfriend that comes to everything. That was never me. And those are the relationships that didn't work out where when they, they wanted that they wanted their sidekick that like signed up for their world and what they were doing and didn't, didn't really want to have a shared vision. And so that's a big part of how I screen now when I when I'm vetting for like who I date I was gonna say are you single like you give us this maybe we should save this for another podcast this is a long story no that's okay yes I have I have a lot of stories of using my own app to date and yes I have had some very serious relationships from the league and I have nothing but great things to say about we just call it research you're just in the research phase right here exactly so I think you know I think you learn a lot from every relationship and what, what you need going forward.

30:49And so I feel like both building the league and kind of having a couple of misfires on the relationship side, I now feel like very equipped to recognize what I'm looking for when I, when I find it, I'm actually not, I'm kind of in that phase of what you mentioned. And I really love that you mentioned that, which is like, sometimes you don't just cause you're single doesn't mean you're trying to change that. Like if you're really focused on, let's say fitness, wellness, and maybe building your business. Maybe like shopping for a boyfriend isn't even on the top five. Maybe it's actually going to be a distraction to those other goals.

31:21And you want to achieve some of those before you find, you know, your person. And so we actually have a status on the league that I built kind of for myself. I think I might be the only one using it actually, but it's basically where you say, you know, you can say you're single or not single, but you can also say whether you're actively looking, passively browsing or not looking. And like, you know, we were selling, I went through an M &A process. we now are bought by match who's now funding this this awesome campaign i'm getting to do and talk to you but like during that process i was not shopping for a boyfriend i was on the not looking i was like i gotta get this to the finish line i gotta like i gotta just get this done it's gonna be like a six-month project and so but but that didn't mean i wasn't open to meeting new people or going to some of these you know karaoke events or rock climbing events or whatever surfing things so it was it doesn't mean i wanted to be anti-social it just meant that i wasn't really like looking to change my status.

32:11And I think that's like an important distinction to make. And I think single people often get like pigeonholed into like, Oh, you must be someone for you. I need to change that part of you. And you're like, no, no, I'm actually doing pretty well single. And then when I'm ready, now I'm going to go fishing for my boyfriend. But like, it doesn't have to be this like all consuming thing. You can go, you can take breaks, you can delete the apps and get back on them. I've done that. I think we all have. So it's, I think it's healthy to like recognize that life is in cycles and you don't always have to be kind of in the search phase.

32:42Yeah. One thing I love that you kind of manifesto on this because I'm always I get sometimes I get triggered when people are like, Oh, are you single? Like, how come? Yes. You know, how are you single? Or like, why are let me try to help you fix it? Yes. Oh my gosh, we went through a tricky stage of our relationship when we were trying to grow our family. And there was one quote that I always clung to during it. And it was like, sometimes the season of waiting is just as important as what it is that you're waiting for. And I just feel, yeah, I feel like that is so true in business, in relationships, in life, in parenthood and everything where it's like, oftentimes when you're in that waiting season, you want to just like waste it or rush it.

33:24And I love that we can talk about like, no, maybe like that is that time that you're building yourself or you're building your independence or you're building your thing, or you're becoming the type of person who is ready for whatever it is that you're going after and incorporating someone into your life. Yeah, exactly. Cause if you like you, you know, you grew together. So I think that's a whole different, like amazing, beautiful experience where you're, you're getting to know each other as you grow together. But then I think, you know, for people that are meeting later in life, you're basically now doing like a joint venture of like, okay, here's how you live your life.

33:53Here's how I live my life. How do we build a joint vision that, that incorporates both of what we love about our lives. And it doesn't involve me sacrificing everything for the guy. It doesn't involve the guy sacrificing everything for me. And so it becomes a lot more about like, you need to know, you need to know what's important to you before you go into this, like merging of the worlds. And for me, a lot of my like intentionally single time, it was understanding like, what does Amanda like to do even when there's no, when there's no significant other in my life. And then now where do I want to insert them?

34:24And kind of just being very thoughtful about the kind of relationship I want to have and what activities I want to still continue to do. Even when I'm in a relationship that may just be so, you know, like I go for long walks by myself. I don't think I want to change that. Even if that's going to cut into my time with my boyfriend, whereas like back my old Amanda, I would probably, if he has a friend's watching sports, I'm going to go watch sports with them. And you're kind of like, assuming you just need to do everything that they want to do. So I found myself compromising a lot in past relationships.

34:53And I'm trying really hard to like center myself on what, what me as a single person likes, and then, and then building that into a relationship. I love that. So you have an amazing campaign going on right now, be a gold digger, which is exactly why I was like, we have to get Amanda on this show. Let's talk about goals. This is, she's got a hat. This is be a gold digger. I have one for you, by the way. Yes. And I love this because you are celebrating all things goals. So tell me a little bit about why the focus on goals. Yes. Why did you guys decide to focus on goals? Like, why was that the main focus as you went into this fall?

35:33Because I love it, obviously. Yeah, no, it's a great question. So the thing with the league is like, it's, you know, it's my baby. I'm taking this off because I'm not like a super hot person. But so the thing with the league is that, you know, the name, the league, we're selective. We don't let everybody in. I was coming out of Stanford when I launched it. You know, I had some kind of fun, quippy marketing messages at the beginning, which was like, if you took the top 30 percent attender, you know, you'd have the league and you put like an admissions council behind it, like you'd have the league.

36:04And so there's a lot of, you know, I like kind of fun, edgy, unapologetic marketing. I do a lot of copy. I do most of all the copywriting myself. So I like kind of having that that attitude with it. And so, you know, I think for better or worse, we kind of got written about in press as like this elitist Ivy League app that like you had to go to one of the eight Ivy League schools and you had to have some C-level job or making, you know, six high six figures to even like be eligible. And for the most part, that was never true. But it was just like that was what people liked to write about that got clicks.

36:38This was in the day when like journalism was moving into paywall, but it wasn't yet. So everybody was about clicks, clicks, clicks. And so the more polarizing and elitist they made us sound, the more people wanted to read about it, which, you know, is a double edged sword. We got a lot of press for it. And like we didn't have the money to pay for for marketing at the time. So in a way, we got free marketing from it. So I didn't I didn't like totally hate it. But then on the other flip side, there was people like, you know, I have friends that were even like friends of mine that were like, I don't think I'll qualify.

37:08And I'm like, wait a minute, you went to a great school. You have a great job. Like, what do you mean? And they're like, but it's only for like MBAs at Ivy League. And I'm like, no, no, no, that's just where I launched it. So I think, you know, for better or worse, we kind of got pigeonholed as this like, you know, highly educated, highly successful, very selective elite app for, you know, the 1%, if you will. And so, you know, when I tried to break it down to people, I'm like, no, no, it's about ambition. It's like about putting the people that are ambitious and have a work ethic and have very career, big goals, career focus and goals kept coming up and up and up.

37:44And then we talked about, you know, what are some of the stereotypes we're trying to eradicate now that we have a marketing budget, finally, like we haven't, you know, for most of the life of the company, we had less than a million dollars to spend on marketing, if that, you know, the first couple years was zero. So it was like, we finally actually have a big boy marketing budget. How do we want to, how do we want to kind of correct the narrative? And I was like, no, the league's about goals. And so we worked with this agency, they're actually the ones that did liquid death, that was called human art, but they, when we talked about ambition and how we want to like focus on that, they came back with like the concept of kind of relating it back to the gold digger concept where, you know, there's a stereotype that women are going after rich men.

38:21And it's like very antiquated because women are now working and we have more money than men. We have more houses than men. We have like, we're going through college and graduate school at higher rates than men. So like, we are not gold diggers. We, if anything, the men are now gold digging us. So it's like, there's sort of this like flip that has happened in our generation. And so the juxtaposition of like, what was old, which is, you know, oh, you're a pretty woman trophy wife for a rich, wealthy guy. I kind of wanted to like directly juxtapose that with like the fact that, you know, there's 55 % of the league is women, maybe even like 58%.

38:56Like we're women focused. These women are high achieving. They're very ambitious. They work their way up the ladder. It's not, it is not elitist. It is actually just like a group of very ambitious people coming together that want to date other ambitious people. And the word ambitious, I think we talked a lot about that. It's, it sort of has this different connotation. And so I think we kind of, we basically boiled it down to like, what do you mean by ambitious? What do we mean when you say someone's ambitious? It's like, they have a lot of goals and they're constantly setting goals and going after them.

39:24And that's a trait and a trademark of very successful people. And I don't think that's anything to be ashamed of to be goal oriented. And I think it's actually a really good way to define what our user base is. So we're kind of moving into a world where we're trying to, to say like, you know, this is an app for goal oriented people, but that sounds kind of cringe. So that's why we, the gold digger was a lot more fun, which is like, are you a gold digger? Come join the app for gold diggers. So it's just a lot of kind of a fun way to, to market it and kind of nod the hat to the past antiquated traditions that are no longer relevant to this generation.

39:56I love that. I mean, obviously I can get behind the gold digger message. I love it. I recently met someone yesterday at a coffee shop and then he was like, Oh, what's your podcast called? And I was like, gold digger. And I'm like, G O A L, not the other way around. And I had to explain him like my husband's a stay at home dad. Like, you know, but it was, he was like an older man who was like a business professor. And he kind of gave me that look and I was like, no, no, no. And so I, I love that. It's Look, I've become kind of a systems nerd and anything that gives me more space in my day, I'm all in.

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42:25Find out how much at airbnb.com forward slash host. So you also launched this feature in your app called Goal Mates. So tell me how Goal Mates works, because I think that my listeners would be really interested in this part. Yes. So this is my like, my brainchild, which is, is there a better way to matched than, you know, right now when you go on dating apps and the league is, is included in this. Like you put in your age preferences, your height preferences, your location preferences, how many miles away do you want them to be? We let you put in your education preferences. You want them to have a master's like, so there's all these like very tactical and like, just kind of like, I don't know if I would say it would like totally irrelevant, but it's like, they're not really the meat of what, what attraction is based on.

43:09And so what we're doing is we're allowing people to select from a list of like 300 goals. So select their top 10 goals that they're going after. You know, some of the options are like light and funny, like stop sleeping on my face is one of my favorite of the lighter ones. And then there's like, you know, write, write the next great American novel. Like that's one of my goals. I want to write a book at some point. And like, I've never done it. I've talked about it. And like, I would love to meet someone that also wants to write a book and like, maybe we can hold each other accountable. Maybe we can go to writing workshops.

43:36Maybe our date is us telling each other the first chapter outlines. And like, and even if it doesn't work out, even if there's no spark and there's no chemistry, maybe I found a really good writing partner in that search. And so I think it goes back into what I was saying is that like, in my perfect world, you're not like separating a search for your soulmate as a separate thing. You're going about your daily life, doing what you want to do, achieving the goals you want to achieve. And then you're bumping into that person along the way on the path of where you want to go. And then you are going together and you're pointing in the same direction with the same velocity.

44:08And I think that's like why a lot of people grow apart is that they weren't, you know, you were lucky. You found someone that clearly wanted to kind of go in the same direction. But, you know, when you talk to people who are divorced, oftentimes that's the number one reason the relationship failed is that we were changed. We changed. I wanted to be over here. They wanted to sit at the TV and drink wine or whatever. And so you hear these stories where people kind of had a different take on what they wanted to get out of their life. And so if you can match on goals instead of like, oh, he fits my height preferences and he is like blonde hair.

44:38It's like, no, let's actually match on something meaningful. And then that way, when you are going through the search process, there's like a common thread that you're getting. And so as you, you know, maybe you're not finding the spark, but you're at least making really good friends that can help you achieve your goals. And I think that that was a big learning for me was that if you look about all the different relationships I've been in, you invest so much time with these people. they place such a big impact on you when you're in a relationship and you're the average of the five people you hang out with the most.

45:05Right. So it really does pay to be with like the most ambitious goal oriented person that wants to go where you want to go, because you're going to have a better chance at reaching your goals. If you're partnering with someone who's also like helping you swim there. Right. So, so I think it was just, you know, my, I guess my romanticized way of like in the perfect world, that would be how we are all, we would all meet achieving our goals and meeting someone on the path of, of achieving that. So the most popular ones right now, I think there's a bunch of people that want to go and try to lose their ego at an ayahuasca retreat.

45:36There's a lot of travel people that want to go, you know, kind of check off a lot of different countries. There's things like starting a family and like having a large family. That's like a goal that not everybody shares that, you know, so it's, it's everything from that to learning how to knit a sweater or hiking, you know, Machu Picchu. So it's, it doesn't have to be like, I want to be CEO of a billion dollar corporation and I'm not going to sleep for the next 10 years. It doesn't have to be this like demanding goal. It's just a matter of like, can we match you on that? And so my, my like dream is that once we've, we've only had this out a couple of weeks now, but like in a couple of months, we'll have data and people who were actually giving you someone in your batch.

46:13So every day we give you profiles, we're giving you an extra person, like kind of like Google's I'm feeling lucky if I'm dating myself with that probably, but you know, so basically it's a goal, we're calling it your goal mate. And so maybe they don't fit your other preferences. Maybe they're not exactly in your 10 mile radius, or maybe they're 5 '10 instead of 5 '11, but they both, you know, they want to do one of the goals you want to do. And so my hope is that we're going to start seeing maybe those matches convert at a higher rate. They exchange phone numbers at a higher rate. They meet in person at a higher rate.

46:41Maybe they have more conversation. And so we'll be able to actually do like a full analytics breakdown on like, are these matches sort of better, you know, holistically, if we match you on, on a goal that you guys both share. So that's, you know, fingers crossed those will, you know, that will show up in the data, but, but if not, at least your, you know, your dates, you have something to talk about. Yes. Oh my gosh. I love that. Okay. Final question is I would love just any dating tips. So how does somebody that's listening, how do they like vet ambition on a dating app or like, how do you kind of feel it out in the first few dates?

47:13Do you have any tips for somebody listening? Who's like, I'm ready to put myself back out there. What do I do? Yeah. So there's a lot of different stages to the search, right first is like just creating you know your initial like list of prospects right so that's hearting people on our app but you know swiping right on other apps so select you know how do you decide who to select right on then once you get the match talking about conversation deciding when to move to the date and then on the date like what questions to ask to screen so I think there's a little bit of different strategies for all of them I tend to be a little less selective on the at the top of the funnel, if you will, just because oftentimes, as you know, on dating apps, people don't write back.

47:53There's a lot of flakiness. Like we've tried to change that. I think all of dating apps have, but in general, you're just never going to know if I'm traveling, I ghost people on dating apps. I'll be the first to admit it. So I'm, you know, and I'm not going to change that. Like if I'm just doing something else, I might not check in. So you, instead of like being upset that maybe only 50 % of people write you back, just take that as part of that. That's how the funnel works. So you kind of want to be less selective on the way in. If there's even something interesting about the profile, I would say like swipe right on it, heart it.

48:22And then, then when you, when you get into the messaging, you can be more selective about who you message, especially if you're a woman, just in general, it tends to be, you get to have to be a little more selective, but men too. And then when you're, you know, when you are messaging, finding that common goal. So we are now showing on the league, like if you have a shared goal, if you have shared interests, I always like talking about those things and you get right to something you can connect on. And then I'm not a big like texter and banter. I think you want to get enough so that you can get their personality, but you don't want to lose momentum.

48:52And you're really trying to get to it. I call it, you want to get to DTL, date, time, location. So like make a plan, see if they're, what are they doing next week? I don't think you should be shy about scheduling it even as a woman, like it's a whole new day and age. And at this point, like nothing really matters until you meet in person. And so you don't waste a lot of time messaging someone you haven't met because you could meet in person and then you just know immediately there's no spark. And then you wasted all this witty banter that you could have, you know, you could have been working on your business.

49:21Right. So I try not to waste too much time on the messaging and the way the league sort of vets for ambition. So you don't have to do that. If you're on another app that doesn't show all that, you may want to ask questions about what they do for work, where they live, like what's their favorite thing to spend time on outside of work and all that stuff. But on the league, because that information is shown, you can kind of go straight to the fun stuff, which was why I liked, I didn't want to ask people about their job. Like I thought that felt weird. I want to ask them like, if you had all the money and time in the world, what would you be doing?

49:49That's like one of my favorite questions. I actually asked that when I interview my VP of engineering candidates and my boyfriend candidates, I asked what they would do if they had all the time and money in the world and like where they would be. And it's a super interesting question to see. It showcases ambition. It showcases impact. It showcases maybe their family values. So you can get a lot out of those kinds of questions. It's a good in-person one though. So if you have a good feeling about it. I still recommend like nothing beats an in-person date. And if you can get the person to kind of commit to a time date location, I think that should be like your number one goal.

50:21And then, and then on the date itself, I think, you know, there's a lot of advice out there that is, I would echo, you know, see how they trade the waiters, see how, you know, if you want to do something, that's not what they want to do, how they react to it. I like to kind of tell people no on the first date to see how they respond. Cause I've had a lot of relationships where I didn't do that until later in the relationship. And then when you don't want to do things their way, they really can't take it. So I kind of like to do a couple of those tricks. I like to be late. This is like a weird one, but because some people get really pissed and like, we'll just write you off.

50:54And I'm like, okay, well, that's not going to work with me because I'm like kind of late for everything all the time. Like I was late for this five minutes. That was good for me. So it's like, you know, and I get that some people think that's disrespecting time. Other people might be like, look, she has ADHD. is real right so i do that and that can kind of i can see if they're like getting mad or like whatever and i'm like this is not gonna be a good fit and so there's a little tricks like i do and then the one of my other tricks is that i always say i always make a commitment for after the date so that even if the date's going well they're the hard stop because you always want to leave them waiting more if it's working and if it's not working you have an easy out you don't have to reject them and say this isn't working you just say i'm going to a dinner with my friends at 8 30 you're meeting for drinks at 7 30 before keep it time-based again like the startup play give yourself a timeline and then I think it's kind of fun like I think just like find out how much you can learn about someone's story and their interesting pieces of knowledge that they know that you don't know I always like to try to find out like what is something you know a lot about that you don't think a lot of people do that's another great question and and I try to have fun on the dates and look at them as like you're meeting really interesting people ideally highly ambitious highly educated highly highly successful so there's like something to be learned from everybody, even if you decide they're not your person.

52:08So I don't know, I guess that's my, those are my dating notes in a nutshell. I love that. Amanda, where can everybody find out more about you? Check out the league, get their goal mates, give me all the places that you can connect. Well, I kind of want to give, I'm going to try to do the, give these hats out to people. So right now we're just the league.com and then I'm at sign Amanda Bradford on Instagram and Twitter. And I haven't started TikTok yet, but I'm thinking about it. So let me know if you guys think it's a good, a good channel to try. But, but yeah, and I think with the Goalmates campaign, we're in New York, New York subways, West 4th, Bedford station, Brooklyn, Brooklyn, Bedford and Columbus circle.

52:45And then in, in LA, we're at the LAX airport. We have airport trades going on and a big giant billboard that says date someone with a five-year plan that will make you Golgasm, which we almost got rejected, but they got it approved at the last second. So I'm really excited about that. So yeah, those are the campaigns. And then, yeah, we're going to probably do be doing a couple more things in New York, you know, towards the end of the year for the holidays. So yeah, we're really excited to download the app at the league.com and all your guests. I'll make sure they get, they get hooked up with a skip the line.

53:14Awesome. Oh my gosh. I'm so excited for all of our listeners out there who are in the space of readying yourselves for the right person. This is a place for you. I'm so excited. Amanda, thank you so much for coming on the gold digger podcast. This was so fun. It's so fun. You're like such a perfect lead representative.

53:36This was such a fun interview. I loved hearing from Amanda about founding her own app and why she built it the way she did with the intention and the heart and the goal digging behind it. She let me know that when you join the league, if you send your concierge, which everyone gets a concierge, how fancy is that? Hashtag gold digger. It'll allow you to have VIP perks and you can skip the waiting line. So again, once you join the league, send your concierge hashtag gold digger and you'll get some extra perks. I am hoping that all of you walk away today just feeling inspired and proud of yourself for being this ambitious, driven person that you are.

54:15And again, always remember, sometimes the season of waiting is just as important as what it is that you're waiting for. I cannot wait to hear your success stories and hopefully a love story or two. I mean, who knows? Maybe I'll be officiating one of your weddings someday. Thank you so much for tuning in to another episode of the Gold Digger Podcast. Until next time, keep on digging your biggest goals. I'm over here giving you a virtual high five because you just finished another episode of the Gold Digger Podcast. Did that go by way too fast for anyone else? If you want more, head over to golddiggerpodcast.com for show notes and all the discount codes from today's sponsors.

54:51And if you're looking for a new crew of movers and shakers like you to bounce ideas and ask questions, be sure to join my exclusive community for Gold Diggers on Facebook. The link's waiting for you at golddiggerpodcast.com.