‘This is Your Life in Silicon Valley’: The League founder and CEO Amanda Bradford on modern dating, and whether Bumble is a ‘real’ startup

Welcome to this week’s transcribed edition of This is Your Life in Silicon Valley. We’re running an experiment for Extra Crunch members that puts This is Your Life in Silicon Valley in words – so you can read from wherever you are.

This is your Life in Silicon Valley was originally started by Sunil Rajaraman and Jascha Kaykas-Wolff in 2018. Rajaraman is a serial entrepreneur and writer (Co-Founded Scripted.com, and is currently an EIR at Foundation Capital), Kaykas-Wolff is the current CMO at Mozilla and ran marketing at BitTorrent.

Rajaraman and Kaykas-Wolff started the podcast after a series of blog posts that Sunil wrote for The Bold Italic went viral. The goal of the podcast is to cover issues at the intersection of technology and culture – sharing a different perspective of life in the Bay Area. Their guests include entrepreneurs like Sam Lessin, journalists like Kara Swisher and Mike Isaac, politicians like Mayor Libby Schaaf and local business owners like David White of Flour + Water.

This week’s edition of This is Your Life in Silicon Valley features Amanda Bradford – Founder/CEO of The League. Amanda talks about modern dating, its limitations, its flaws, why ‘The League’ will win. Amanda provides her candid perspective on other dating startups in a can’t-miss portion of the podcast.

Amanda talks about her days at Salesforce and how it influenced her decision to build a dating tech product that focused on data, and funnels. Amanda walks through her own process of finding her current boyfriend on ‘The League’ and how it came down to meeting more people. And that the flaw with most online dating is that people do not meet enough people due to filter bubbles, and lack of open criteria.

Amanda goes in on all of the popular dating sites, including Bumble and others, providing her take on what’s wrong with them. She even dishes on Raya and Tinder – sharing what she believes are how they should be perceived by prospective daters. The fast-response portion of this podcast where we ask Amanda about the various dating sites really raised some eyebrows and got some attention.

We ask Amanda about the incentives of online dating sites, and how in a way they are created to keep members online as long as possible. Amanda provides her perspective on how she addresses this inherent conflict at The League, and how many marriages have been shared among League members to date.

We ask Amanda about AR/VR dating and what the future will look like. Will people actually meet in person in the future? Will it be more like online worlds where we wear headsets and don’t actually interact face to face anymore? The answers may surprise you. We learn how this influences The League’s product roadmap.

The podcast eventually goes into dating stories from audience members – including some pretty wild online dating stories from people who are not as they seem. We picked two audience members at random to talk about their entertaining online dating stories and where they led. The second story really raised eyebrows and got into the notion that people go at great lengths to hide their real identities.

Ultimately, we get at the heart of what online dating is, and what the future holds for it.   If you care about the future of relationships, online dating, data, and what it all means this episode is for you.

For access to the full transcription, become a member of Extra Crunch. Learn more and try it for free. 

Sunil Rajaraman: I just want to check, are we recording? Because that’s the most important question. We’re recording, so this is actually a podcast and not just three people talking randomly into microphones.

I’m Sunil Rajaraman, I’m co-host of this podcast, This is Your Life in Silicon Valley, and Jascha Kaykas-Wolff is my co-host, we’ve been doing this for about a year now, we’ve done 30 shows, and we’re pleased today to welcome a very special guest, Jascha.

Jascha Kaykas-Wolff: Amanda.

Amanda Bradford: Hello everyone.

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Amanda Bradford. (Photo by Astrid Stawiarz/Getty Images)

Kaykas-Wolff: We’re just going to stare at you and make it uncomfortable.

Bradford: Like Madonna.

Kaykas-Wolff: Yeah, so the kind of backstory and what’s important for everybody that’s in the audience to know is that this podcast is not a pitch for a product, it’s not about a company, it’s about the Bay Area. And the Bay Area is kind of special, but it’s also a little bit fucked up. I think we all kind of understand that, being here.

So what we want to do in the podcast is talk to people who have a very special, unique relationship with the Bay Area, no matter creators that are company builders, that are awesome entrepreneurs, that are just really cool and interesting people, and today we are really, really lucky to have an absolutely amazing entrepreneur, and also pretty heavy hitter in the technology scene. In a very specific and very special category of technology that Sunil really, really likes. The world of dating.

Rajaraman: Yeah, so it’s funny, the backstory to this is, Jascha have both been married, what, long time-

Kaykas-Wolff: Long time.

Rajaraman: And we have this weird fascination with online dating because we see a lot of people going through it, and it’s a baffling world, and so I want to demystify it a bit with Amanda Bradford today, the founder CEO of The League.

Bradford: You guys are like all of the married people looking at the single people in the petri dishes.

Rajaraman: So, I’ve done the thing where we went through it with the single friends who have the app, swiping through on their behalf, so it’s sort of like a weird thing.

Bradford: I know, we’re like a different species, aren’t we?

Rajaraman: It’s really confusing, and as a married person, you don’t really want to install the apps on any of your devices. It just doesn’t feel right.

Bradford: Yeah, it won’t look good to your significant other.

Rajaraman: Not at all. So here’s the thing. We’re going to talk about dating in the bay area today, but before we even get into that, Amanda, can you tell us where you grew up? Are you a California native?

Bradford: I did, I’m a bay area native, so Fremont, if anyone’s from Fremont? I lived there from zero to third grade I guess, went to Austin, Texas, and then Chapel Hill, North Carolina, so I took a little lap around the U.S.

Rajaraman: And in that lap around the U.S., as you were in Austin and in Chapel Hill, that entire time were you like, “I really wanted to just get back to the bay area,” has the bay area always called to you?

Bradford: Well, I feel like I was at my most creative in the bay area. I remember, going, well you get to go to school outside in the bay area, which is cool. You realize that going to the East Coast, that’s not a normal thing.

I think my dad was in technology, I think we were the first family in the bay area to even have, I think back then it was called, it was pre PalmPilot it was called like Einstein or something, we had the like very first you know iPhone from the 90s and we were on CompuServe and Prodigy and ICQ and so I knew all this stuff, because I had two older brothers, so I remember my friends were always like, “you’re really into tech and social networks,” I was social networking at a young age.

Lisa knows my story about internet Amanda, I stalked everybody in Texas before I moved there on AOL buddy chat, and basically created a group of friends before I landed into North Carolina. So I’ve always liked technology, and this is where it’s built, so I mean, it made sense to come back.

Rajaraman: And when you came back, what was your angle back in? Did you say, “I’m going to go to school here, I’m going to move back here and start a company,” like why come back here, what was the driver-

Bradford: Mark Benioff got me back here, well, I wish I could say it was personal, but no, his company, Salesforce, recruited us out of Carnegie Mellon, and so I was deciding between going to New York and working in finance and with Excel, and then I came out to San Francisco and they took us on a duck tour around the Bay Area, and everyone was doing like yoga in these rooms painted orange, and I had just been like to city group where everyone was like so miserable and pale, and like crying into their hands at 11 at night, and I was like, “I think I’m just going to take a pay cut and come to the West Coast is the best coast,” so I made a call at like 21, and so I moved out here and almost all the Carnegie Mellon people went to New York, so it was kind of the place to be at that point in 2007, then the financial crisis hit, so actually I made the right call.

Rajaraman: Yeah.

Bradford: But yeah, I think that, I like to say Salesforce, at that point that was 2007, so SAS was just taking off and all this really exciting things were happening and Mark’s also very good at delivering Kool-Aid to drink, so I’m very much a Salesforce fan girl through and through.

Rajaraman: So for our listeners who, surprisingly enough, aren’t all in tech, can you define what SAS is and talk about who Mark Benioff is? I think many people know who Mark Benioff is, but just as a [crosstalk 00:05:15]

Bradford: So, I know, give some spotlight to Mark, who brought me out to San Francisco. So he, they built CRM, which is Customer Relationship Management, so if anyone who’s done sales, that’s sort of the main software used to track your leads and to sell, close deals, and his big innovation was putting it online before everything, you know before that everything was on premise, and so he was very much a pioneer.

And you know, kind of what I feel like what we’re doing into the mobile space with dating is similar to what he did with software, bringing it to the cloud, is that it was always on premise, he brought it to the cloud, dating was always on website, now we’re bringing it to mobile, so he’s very much kind of brought tech into the 21st century.

(Photo by Kimberly White/Getty Images for GLAAD)

Kaykas-Wolff: So audience participation time. So we have a live audience of about 2,000 people. We need a audience photo shot later, which we’re going to tweet out. How many people here have tried online dating? Okay, so just keep your hands up-

Bradford: Yeah!

Kaykas-Wolff: Keep your hands up, actually, please-

Bradford: Great.

Kaykas-Wolff: Just hang on a second, so, we’ve got about a thousand hands up. Of the people who have tried online dating, keep your hands up if you’re happy with online dating. Wow! So, about 750 to 800 of the hands of the hands just dropped out.

Rajaraman: Gone.

Kaykas-Wolff: Just dropped off. Amanda-

Bradford: Online dating has a very low NPS score as a category.

Rajaraman: So, Amanda, what is wrong with online dating? Explain it to us. Is it the apps? Is it something about us that’s changing, just do your best summary of what’s wrong with online dating.

Bradford: Well, it’s a big question. I think, so you asked and you had sent me a question asking is it broken, and I actually don’t think it’s broken. I think broken implies that it doesn’t work at all and you can’t use it to get to your final goal, which I think you can, I think there’s plenty people of who have had success on online dating, so it is possible, I think it’s just massively, massively, inefficient, and now that it’s the kind of main way people are meeting, and the other channels are kind of breaking down.

I think the inefficiency is highlighted, because now none of your friends are setting you up it’s not like you’re meeting at parties anymore, everyone’s focused on just their phone and meeting through the phone, so I think it’s amplified, the inefficiency.

Rajaraman: So why did you decide that this was a problem that you wanted to focus on and what, kind of explain what The League’s approach is and why your approach is better.

Bradford: Yeah, well I was single after five years and I was like dipping my toe back into the dating pond, and I downloaded I don’t know, OkCupid, I think Hinge was just coming out, Bumble I don’t think had come out yet, but I had the same issues with each and every app, which was everybody was like pretty much anonymous.

You could basically say you were whoever you wanted to be, you could put any picture, you could say you went to whatever school, there was no layer of authenticity, and then you also, there was also a lot of vetting, like there wasn’t, you don’t like your profession or education or anything, so I’d have to go and stalk all these men, and be like, “Oh he’s wearing a Duke shirt, okay, maybe he went to Duke,” and so I’d go onto LinkedIn, and be like, “Matt, comma, Duke, comma, maybe like class of 26,” and so I’d start looking through the graduation year, if you have LinkedIn premium you can do that.

And so that was like, I was starting to vet before I decided if I wanted to go on these dates, because I was living in Palo Alto at the time, so it was like, you know an hour an fifteen minutes just to even get to the date, so I was like, you need to do some diligence to make sure that’s going to be, has a good probability of being an okay date.

So I would find myself doing a lot of stalking and vetting is what I call it, so I felt like why not just use LinkedIn as part of the onboarding experience and make it a community where people are who they say they are, there’s this authenticity, there’s this sort of handshake agreement that everybody is not going to be anonymous or make up fake profiles and I wanted to use it to find myself the best match and have the best database.

Rajaraman: And so critics might say the exclusivity, that kind of can rub people the wrong way-

Bradford: Well the exclusivity was my way to solve what the issue is with online dating in general, which is it’s just this huge race to the bottom, as soon as you open any, honestly any community that’s open, Twitter’s the perfect example of this, it’s like there’s amazing, smart, really intelligent people on Twitter and then there’s like terrible trolls of humans that like nobody wants in their community, right?

So it’s like okay, what if we create a community with a wall at the beginning, and we make you kind of have to climb the wall to get in, maybe we can create a community that doesn’t have these like kind of negative group of people that tend to bring down a lot of social networks, so that was like one of the design decisions to kind of prevent some of the issues with online dating.

Rajaraman: As a person who never dated or found a match through an online site, the idea that dating is about being more efficient feels really weird-

Bradford: Yeah, it’s not a romantic way to say it, I know. I get feedback on that a lot, but-

Rajaraman: And how did you respond to that feedback? If I’m giving you that feedback right now-

Bradford: I grew in sales, I think in pipelines, it is, you know, I consider it’s a process, it’s a funnel, it’s just like any other sales process, but it isn’t, you’re right, it isn’t the most romantic way to say it.

Rajaraman: So can we talk about efficiency of successful matches in the league in the bay area? Like what city, what neighborhood in what city is the most efficient at finding matches on League?

Bradford: The most efficient, well, we can look at popularity, so popularity is a number that is very correlated to  number of matches, because if you have a high popularity that means when you like someone you have a high chance that they’re going to like you back, so that’s what we call the kind of like, people with high League scores is what we call them, and so they, yeah, they do tend to, I mean like the Marina, we looked at where our most popular users lived, and lo and behold, they lived in the Marina-

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Image via Getty Images / normaals

Kaykas-Wolff: Why are there so many giggled in the audience when you say the Marina?

Bradford: And then you would see them starting to gravitate towards Hayes, when Hayes became cool, but it was, yeah, it’s definitely, you can see some of the stereotypes of the city through the dating, which is quite hilarious, even see San Jose has like not as many women and you’re like, “If only I could move these neighborhoods next to each other.”

Kaykas-Wolff: So this is kind of like depressing and boring, I feel like I didn’t miss anything. What you’re saying is this is like a numbers game. This is a massive numbers game. Is that really what it is, is this about just reaching out to as many people as possible, like give me the hopeful case on this.

Bradford: Well, I mean, you can again call me unromantic, but I do think it is a numbers game. I think you have to meet, you have to kiss x number of frogs to notice the person’s a prince and to know what you’re looking for and I think the other point to your question is more societal, is that a lot of people are dating but they don’t know what they’re looking for.

And they don’t really know what it is they want, and there’s people on both sides of that equation, like searching but not knowing what they want, so it kind of adds, it convolutes the whole process. It’s not like both people are like, “I was to buy a house, with a four car garage and this, this, and this,” and then it’s just a simple matching problem, it’s like, “No I want this, but then I’m saying that but then I’m rejecting people that I said they want,” so you see, you kind of see humans inconsistencies, and their own biases.

Kaykas-Wolff: So your boyfriend is in the audience, lovely gentleman. Met him earlier. You want to wave? No, no wave.

Bradford: No, he doesn’t [crosstalk 00:12:16]

Kaykas-Wolff: We got to put him on the spot a little bit. How many people, was it, how did you find your match on The League?

Bradford: Well I was actually pulling my phone out because I was going to say it is a numbers game in the sense that I did this presentation at The Battery the other week about why video is so interesting to us because when you put together two people on a video chat, you don’t have to do any of the messaging, you skip all the kind of games, you skip all, all of a sudden you’re almost on a date, so I was saying that if people could just meet on video for two minutes, you could basically disrupt the whole kind of static image dating industry as it is.

And so I was looking at Jeremy and I’s stats, and how many people we had to talk to and how many people we had to engage and meet, and it is a numbers game, it was pretty funny because it was like, I think I had, well, he doesn’t like hearing this, I had 946 matches in the four years that, I mean granted, I’m a power user, but if you actually go down the funnel, I actually only met six of those people in person of that entire, granted I’m kind of a weird outlier person, but like for him he had 143 matches, he met four people in person.

So it’s like, it is, I mean that’s sad, that’s a sad stat, it makes The League sound bad, but then we actually reran the study on like Hinge and some of these other sites, and it’s the same story, it’s like just because you have a match doesn’t mean you’re going to actually meet them in person, there’s like a long journey between that. So that’s why I think I’m really bullish on video, kind of almost leapfrogging the whole thing.

Rajaraman: Shouldn’t the selection process in the front of The League make that top of the funnel better?

Bradford: It is, it is, but you still have, I mean, there’s still all these other things that have to fall into place, right? Both people have to, first you have to respond, someone has to message, right, so half the matches don’t even match, there’s nobody. So that’s just weird, right?

It’s just window shoppers, or sometimes people are like, they’re not really dating, but they kind of want to check it out, so that’s just part of, we call them, like in the dating space, it’s like those are the window shoppers that you just like, you’re always going to have those people, right? They just aren’t going to message, they don’t really match, they just kind of want to see.

And then you have the people that are going to message, and then you have some people that just won’t send a first message, so there’s like some group of women that just refuse to send the first message, and then there’s a group of men that will just send everybody the same message.

Kaykas-Wolff: Oh my God Sunil, this sounds horrifying.

Bradford: And then there’s some people that just send their phone number out as if that’s like a good opener, so it’s like you kind of have all these different personas of like different people trying different strategies, but at the end of the day it’s like there’s so many things that have to fall in place for it to happen that I think I’m always encouraging my girlfriends like open your preferences, open your mind, say yes more than you say no, you can always like say no later, it’s not like there’s nothing wrong with being open-minded at the beginning and then being more filtered towards like who you want to pick as your boyfriend, but you don’t need to be so selective at the top of the funnel because it’s like there’s all these other conversion rates that have to go right.

So I’m trying to explain it as a funnel to my friends, and I’m like, “You each have your own funnel of different conversion rates, and some people are really good at converting the message to the phone number, and then some people are really good at getting the like but then they don’t engage with messages, so everybody has their different strengths in the dating app game.

Kaykas-Wolff: So I guess, what are some tips? Let’s just walk away with a takeaway of the two. If there’s one or two things that people who are having trouble with online dating remember from this podcast, what is it?

Is it update your profile picture to something realistic, is it change your tagline? What are a couple things that people can do to improve their chances of finding that person or whatever it is they’re looking for?

Bradford: Well, I mean the photo, as much as I hate to say that, because it sounds like we live in a superficial society, but we do, and the photo it doesn’t mean to you need to be like this golden ratio attractive person, it’s just like put a nice quality photo up there, like a high res-

Rajaraman: I just want to say I never expected golden ratio to be used on the podcast.

Kaykas-Wolff: Well it’s like look at Sunil’s face, it’s kind of got the golden ratio.

Bradford: He has a beautiful golden ratio. Triangle, whatever it is.

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Image via Getty Images / Anna_Isaeva

Kaykas-Wolff: You’re blushing. Keep going, okay, so the picture-

Bradford: You’d have a high League score, Sunil. So yeah, I mean the photo-

Kaykas-Wolff: Wait, wait, can we talk about that for a second because Sunil and I were driving over here together, he picked me up from the office in his minivan, and as we were driving-

Bradford: That might knock your League score down.

Kaykas-Wolff: [crosstalk 00:16:36] I’ve got three kids and our cars are a mess all the time too, so as we were sitting in the car we’re looking at each other and we’re like, do you, would we pass the filter test to get into League?

Rajaraman: Listen, we’re not going here.

Bradford: Let’s look up his headshot on LinkedIn.

Kaykas-Wolff: I think you could get on. Maybe. Well actually where are your matching people? Do you keep them in the same group with Facebook in some other country and they review from there, Sunil’s social profile?

Bradford: No, we have a concierge team that’s remote, so we don’t disclose where they live. They live all over.

Rajaraman: Okay, so picture. Going back, let’s focus Jascha.

Bradford: Yes. We’re focusing.

Kaykas-Wolff: Yes. Minivan.

Bradford: Okay well the number one takeaway is just have a high-quality photo, high res, get I mean even actually with the iPhone X, the whatever profile mode is called, profile-

Rajaraman: Portrait.

Kaykas-Wolff: Portrait, yeah.

Bradford: Portrait mode, so just that’s just like a everybody should do that because that’s just you’re hurting yourself if you’re putting like a fuzzy photo, it’s just like the very basic, basic thing, like use a high quality photo, high res.

Second would be, well, I guess I don’t want to say it in a negative way, but a lot of people kind of they write as if they’re searching for an apartment and it’s like, “looking for this, this, this, and this, and I don’t like when you eat, you know, meat or whatever” and it’s very much a turn off and as far as they’re trying to describe their perfect human and then… so I think there’s a lot of times it’s like maybe describing yourself and talking about you know, who you are, versus what you’re looking for, I think that tends to be a mistake I see a lot of people-

Rajaraman: And then the other thing I see everybody who I know who has an online dating profile, its like, “Loves to travel. I love to travel!” Right?

There’s “I love to travel,” there’s a few other things that are always in there, right, it’s “I’m a foodie,” or you know, sarcasm and wit, if you can handle sarcasm and wit you can handle you know… what are some other?

Bradford: But the sarcasm and wit-

Kaykas-Wolff: I think your profile is great, Sunil. I really do. Like I think it’s an awesome profile.

Bradford: Yeah. We should review it now.

Rajaraman: This is not going in a direction [crosstalk 00:18:38]

Bradford: This is becoming the Sunil show. But that brings up the third point, which is wit and humor and being kind of interesting in your profile. A lot of people not only describe their perfect person, they do it in a very like not fun or funny way, and it’s like, so I think using wit, using humor, but in something that people can respond to in their message, that’s always, we find that the unique thing someone says is usually what is getting sent out as like your first opener, so if you say something like, I don’t know, we always say, the one we put on our poster for The League is a guy saying, “First I’m going to get close to you, then I’m going to get even closer to your family and like, you know, steal them from you,” or something like kind of weird but like kind of creepy but funny, and then you know the women all are like, “Oh I thought,” you know they’ll make a comment about how they wouldn’t like my brother or whatever.

So I guess, long story short, just being creative in what you’re saying allows people to kind of latch onto something to say instead of being like, “Oh you like to travel, where to?”

Rajaraman: So if you were to move to the bay area again right now, and The League was already up and running, and you couldn’t move to the Marina, where would you move to?

Bradford: L.A. No, I’m kidding. I’m just kidding, I would stay in San Francisco. I mean I guess right now we live somewhat close to Hayes and it seems like it’s becoming a very small but cool spot, so it’s nice and central, it doesn’t have a stereotype quite yet, so.

Rajaraman: But L.A., so what you’re bashing on the bay area, you don’t like the bay area?

Bradford: Well, no, I just-

Rajaraman: Are you tired of it?

Bradford: I found my boyfriend in L.A. for a reason, so-

Rajaraman: Yeah. Well that’s a real [inaudible 00:20:12]

Bradford: No, I’m not bashing on San Francisco, I just think for me at least, I’m in tech and I think about startups 100% of the time, and then I was dating people that were in tech and thinking about startups 100% of the time, and every time my dating life felt more like a board meeting half the time, because everyone, “What’s your churn rates-”

Rajaraman: [crosstalk 00:20:30] your funnel.

Bradford: And you’re like, “can we really talk about our funnel at dinner?” So I think for me, I was excited to kind of meet, I mean one of the reasons when I built The League was to like, match kind of successful and interesting and creative people in all industries, not just the ones you meet every day, so like I would have never met a musician in probably San Francisco, so I think, you know I think for me that was a learning I had from dating, having 190, whatever, 942 matches, was that maybe I didn’t want to date a tech, you know another person in tech.

Rajaraman: Do you think that it’s more systemic here in the bay area? Do you think there’s just fatigue generally of the types of people or the types of interests that are here?

Bradford: I mean we are a very homogeneous city, so it’s hard to go anywhere without hearing people talk about cap tables or evaluation or you know, churn rates.

Kaykas-Wolff: Back to the audience participation, I’m actually really curious about this thread. So, for those of you who are online dating or single, would you view it, raise your hand if you would view it as a negative if someone were in tech. Would you view it as a negative if they said that they were in tech? That means everybody here is in tech.

Rajaraman: There is literally one person out of 2,000 that raised their hand.

Bradford: I feel like you’re twisting my words though, I’m not anti-tech.

Kaykas-Wolff: Oh no no, I’m not suggesting you are. I was just more trying to, not at all, I was just really curious from an audience perspective-

Bradford: I like my tech people.

Kaykas-Wolff: Just because there is a lot of stink on the tech industry right now.

Bradford: No, I know. No it is, and we do have, we’ll have users write in that are like, “Can you make it so that I don’t see finance pros or I don’t see tech people or I don’t see,” you know so everyone has their own baggage of what they think they need or you know, stereotypes that they like to put on people, so.

Rajaraman: So with that filtering that exists in The League, do you see different groups of people, is the same homogeneity in Los Angeles as the same as New York, where are you, and is it different in the bay area?

Bradford: Well we do see that people in the same professions, this is contrary to my own personal experience, but people in each other’s professions tend to match, so you know, the tech [inaudible 00:22:27] the tech, the lawyers match with the lawyers, the doctors match with the doctors, I think obviously there’s a common interest and common understanding there, so we do see that, and especially in the bay area we see a lot of, just a lot of tech power couples I guess, I would say getting together.

Kaykas-Wolff: Now going back to, so you said some of the positive things that people should look for in profiles, but what about negatives and red flags? What are some things out of your own experience and through The League, if you see this you should run. What are some examples of that?

Bradford: There’s a lot, but we do try to screen a lot of those people out of The League, so I’m lucky not to have to see them too much, but obviously, you know, you have your classic like people with, people in photos with like a ton of people in bikinis and you know, their keg stand wild party days, so you definitely have a lot of offenders like that, that aren’t using the most classy of photos, so we try to keep those people on the wait list and tell them to, you know, no shirt, no shoes, no service.

But I would say the picture can really turn people off quickly, even if you think it’s like, “No that’s my sister,” you’re like, I don’t care that it’s your sister, she’s like in a string bikini and it doesn’t look good, just don’t put  one of you and a girl, pick one of you and your grandma.

So it’s like pretty common sense stuff, and I would say the other thing is grammar is always a very, just a get a friend to grammar check your, especially for The League because people have very high standards about grammar here, we get like people writing in all the time, “I can’t believe you let this person in who wrote this your and you’re incorrectly-”

Kaykas-Wolff: Oxford comma.

Bradford: And so people get very, very fired up about that, and so we try to encourage grammar checking now.

Kaykas-Wolff: I’m curious, I’m just going to rattle off a few apps, and I’m curious, and you can be diplomatic if you want, give you an opportunity to, but what do you think of a few of these apps? I’m just going to throw out a few names that I’ve heard. Raya. Have you heard of-

Bradford: Is this a word game, I just give you one word?

Kaykas-Wolff: Yeah, you could do one word, you could do one sentence, you could do two sentences, you could do two minutes.

Image via Getty Images / Anya Plonsak

Bradford: C-list Instagram and micro influencers.

Kaykas-Wolff: Love it, okay. I like where this is going. Tinder.

Bradford: Quick hook-up.

Kaykas-Wolff: Coffee Meets Bagel.

Bradford: Dating.

Kaykas-Wolff: That was the biggest not answer in the history of our podcast. Audience members, which ones did I miss? What’s a good one?

Audience:    OkCupid.

Kaykas-Wolff: OkCupid.

Bradford: Oh, kind of quirky. Quirky dating.

Kaykas-Wolff: Quirky?

Bradford: Like younger millennial, not too serious dating, but you know kind of like Marina bro.

Kaykas-Wolff: Okay. What else we got?

Audience:    Bumble.

Kaykas-Wolff: Bumble.

Bradford: Now I’m feeling like this is bad, I don’t know I got into this. Fake startup?

Kaykas-Wolff: Love it. Alright, this is the kind of material that-

Bradford: You told me to be honest!

Rajaraman: Yeah, we appreciate it.

Kaykas-Wolff: This is great, that’s what makes-

Bradford: You said people like authenticity, right?

Kaykas-Wolff: We’re trying to just keep the customers at Betabrand happy.

Bradford: Maybe we’ll edit that out. No, I’m kidding. Sorry, what was the last one?

Rajaraman: It was eharmony, I believe Dr. Neil Clark Warren, I remember those, he used to do like TV advertisement back in the day.

Bradford: Later stage marriage. Like on your way out.

Kaykas-Wolff: Interesting.

Rajaraman: I’ve been to like two or three eharmony weddings. Jascha met his wife on eharmony.

Kaykas-Wolff: Yeah, totally. I’m so old, these things didn’t even exist then.

Bradford: Yeah it’s getting older and older, so you were probably more in its-

Kaykas-Wolff: You didn’t actually have to-

Bradford: Its heyday, its heyday wasn’t always like that.

Kaykas-Wolff: That’s the last one we’re going to do, but Jswipe was the audience.

Bradford: Oh. I don’t-

Rajaraman: I’m shocked some of these are real things, by the way.

Audience: Wait, what is Jswipe?

Rajaraman: Exactly.

Bradford: It’s a mobile first Jdate, so that was their-

Rajaraman: Oh. That’s a very apt, very good, very very good.

Bradford: I guess niche, I’d call it niche.

Kaykas-Wolff: Alright, so where is this all headed? Okay, so ten years from now, we have The League, we have Tinder, we have other stuff going on, where do you see this heading? Like what is online dating or AI dating or virtual reality dating or augmented reality dating, what is it in ten years?

Bradford: Oh, yeah. No I have a lot of visions.

Kaykas-Wolff: Yeah, tell us about it.

Bradford: It’s just hard to execute on them because the technology is not all ready yet. I tried to do this. We actually tried to have a VR dating party last year and the technology was too early, it did not work, we had like all sorts of logistical issues of getting people to connect. Basically what I think is going to happen is that there’s going to be kind of this blend between what FaceTime is doing, so video dating, plus AI dating, VR dating where you feel like you’re actually in 3D with someone and you’re in the world with them, so we’re like inching our way-

Rajaraman: Can we talk about AI dating for a minute? What do you mean by AI dating?

Bradford: Sure, VR. Well, VR dating.

Kaykas-Wolff: VR, not AI.

Bradford: I don’t know, AI dating sounds buzzwordy.

Kaykas-Wolff: AI would be like, Sunil’s representative AI is dating on his behalf.

Bradford: Yeah, that sounds buzzwordy.

Rajaraman: Well AR, I said AR, but there is AI, I guess like they-

Bradford: An algorithm is, whatever, everything’s AI.

Kaykas-Wolff: Yeah, yeah.

Rajaraman: That’s not real.

Kaykas-Wolff: So like virtual reality weddings and things like that?

Bradford: Yeah, well not weddings. So what we tried to do, and we had a party in L.A. and San Francisco at the exact same time, and we had them both do a oculus headset, and so we basically paired up a guy in L.A. with a girl in San Francisco and had them meet in the world, but they were both obviously not in the same city, and then they could go and explore the world and check out the caves and the dungeons or whatever it was in that VR world.

The VR world wasn’t that great, it was still too new. I was like, “I have a lot of ideas for how we can make this world a little cooler,” because it was built by you know very early stage developers, so you get to their like “Welcome to my world,” it’s a very weird experience trying it, but it made me very bullish on the fact that this is definitely going to be, you can put on a headset and the you get to meet all your dates and it looks like your dates, and it feels like your dates, and it’s their voice, and it’s their gestures, and it’s what they look like on a first date, there is going to be no first dates anymore, it will all be second dates in person, right, so, that’s the vision.

Rajaraman: Is that appealing?

Bradford: It’s more efficient at least. I mean I’m not judging whether, I mean we’re not doing it, so it’s hard to know if it will be better or worse, but I think it will definitely cut down on the time spent with people you wish you didn’t have to spend time with, right? If you’re like optimizing just on cutting out time spent with bad dates, I think it’s a huge win.

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Image via Getty Images / nadia_bormotova

Rajaraman: Yeah. We’re actually getting close to time, believe it or not.

Kaykas-Wolff: We are, we’re getting close, I just want the audience members to, we are going to have a little interesting audience participation segment, so, and this is completely not staged.

Bradford: For all thousand people here.

Kaykas-Wolff: For all, I think it was 2,000, right?

Bradford: 2,000, right.

Kaykas-Wolff: But if anyone is brave enough to share an online dating story, we actually want to make this entire episode about online dating, and hopefully a good online dating story, not “Oh yeah, hey we met online, the end, great, happily ever after.” A good one, just start thinking of it, we’re going to call someone at random and interview them about it.

Okay, alright, but before we wrap up, I wanted to tease a question to you, and Sunil’s going to ask a question. This is the same question that we end each of the podcast’s episodes on. So I want you to think about the social networks you spend your time on.

You can pick your own network if that’s what you choose, and we’re interested in you telling the listeners of the podcast, the people that are here in the live audience, who you would recommend they spend some time and listen to? Where their attention should belong. So that’s what we want to end on, so think about that, tease it out a little bit, but before we go there, Sunil.

Rajaraman: What am I supposed to do now? I forgot.

Kaykas-Wolff: I just really one more time want to see if you think that Sunil’s profile would do well on The League.

Bradford: We want to create your League profile and test it.

Rajaraman: This is honestly getting a little ridiculous and I’m sweating like a pig up here, so this is just not working. This is hotter than-

Bradford: Hey, people are going to really like your height. Really popular.

Kaykas-Wolff: He has the longest torso. Ever.

Rajaraman: It’s the legs that are longer.

Kaykas-Wolff: It’s just a long running joke.

Rajaraman: Okay, no, but let’s, I have like one or two more questions for Amanda, if that’s alright. So, okay. So your experience was a good one on The League. And presumably you want everybody to have a great experience on The League, but I’m sure you get this question asked all the time, but isn’t there somewhat of an incentive for dating sites to remain on the dating sites, and for people to remain on the dating sites, that natural just kind of, because if people are successful, they’re going to move off, can you just talk a little bit about that and you know, your perspective on it?

Bradford: Yeah. It’s the Achilles heel of our industry, but it is true, it is true. When you match people successfully, typically they don’t stay on a dating app unless they have different hobbies and interests, but you know one of the things that we like to think is that that’s like good churn, right?

And so there’s good churn, there’s bad churn is like when you don’t get any matches and your like, “This sucks,” so what we try to do is really prevent bad churn, but good churn we celebrate, and we hope that, you know the way we think about it is if two people are having a wedding and there’s 300 people at the wedding, and they’re writing that they met on The League, that’s better marketing and advertising than we could do ourselves, so they kind of make up for those two lost spots by themselves, by the success of it.

Rajaraman: Have there been a lot of League weddings, or-

Bradford: Yeah, well we actually have more New York Times wedding announcements than Bumble, and they have like a hundred times our user base, so it’s-

Kaykas-Wolff: That’s the fake startup one.

Bradford: Yeah. Well that’s why they have a hundred times our user base, but…

Kaykas-Wolff: What’s one thing that you can say that might be hopeful about online dating to the people who raised their hands in the audience, the 2,000 people, the 1,000 who said that they had bad experiences, whatever it was, I’m forgetting my numbers now, what’s a message of hope you could give them, and what will change about online dating that will make everybody raise their hands and say, “Wow, it’s been a wonderful experience,” like what has to change?

Bradford: Well no, it made me sad that people aren’t liking it, because I think it’s so much better than it used to be, I mean before online dating was kind of allowed and non-stigmatized, I mean it was so hard to get a date, I probably had one person set me up in a full year, before online dating came.

So it’s like you have to, people are always going to complain about everything, but it’s still better than it was, so A, that’s one I guess area of hope, but more for the, as far as making it work for you, I think it’s just being really pragmatic about your approach and deciding, “Okay, I’m going to date in the month of July, this is going to be my dating month. I’m going to go on two dates a week, and I’m going to do it four weeks in a row, and you know, I’m going to probably meet eight people, and maybe I’ll like two of them,” so it’s like you actually have to meet people in person to find a significant other.

And so I think people forget that and they’re like, get trapped in the swiping and the messaging, but it’s like, just start engaging and it will work. It’s like any other process, and I think at least with The League, we do see that, you know a really high percentage of matches do write back and are very much there for with high intent to find a relationship, so it’s just like, stay with it, give it like you know, give it two months, and don’t be so picky, like be a little bit open minded and who knows, someone will surprise you, maybe they’re one inch below your height preference, but hey, they’re still a great person. So, it’s like you know, kind of just getting out of your head a little bit.

Rajaraman: What’s a question we should have asked you that we didn’t?

Bradford: You should have asked me how I…you should have asked me about my first date with Jeremy, because I actually told him, I had to change my location to L.A., he didn’t know that I was in San Francisco, and then I booked a flight for our first date without telling him I was there for work, but he was actually, because I knew the dating market I was like, “I got to grab this one up.” I got to go. So I was like-

Rajaraman: Did you know that?

Bradford: No. He was like, “Wait, so now it says your location’s in San Francisco, what’s up with that?” And I was like, “Oh, well, we’ll talk about it at drinks.” So I’m not, yeah I’m not endorsing lying-

Bradford: Yeah, our relationship was built on a lie.

Rajaraman: How long have you been together?

Bradford: It will be two years in November.

Rajaraman: Congratulations.

Bradford: I’m not endorsing to lie, but I am endorsing to just be, you know, like take risks, you don’t have to be so in your box, you know, maybe take a 90 to 150 dollar flight to L.A. for a weekend and go on three dates, who knows, you know, so it’s just like kind of live a little with it.

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Image via Getty Images / Rawpixel

Rajaraman: So who are the people that you spend time listening to or watching on social networks that inspire you?

Bradford: I know you want me to say Gary, V…

Rajaraman: Gary V., Tim Ferriss are like, they make my heart hurt.

Bradford: I am not a huge social media person, I’m weird, I like, I actually like reading Quora medium and Twitter, so I like kind of the weird quirky ones I guess, and I was saying the one follower I like on Twitter is this B2B software guy Jason Lemkin, but he, I like him because whatever he does he programs his buffer account to send out some inspirational quote every day. But it always seems to be coming to me exactly when I’m like, “Oh, I can’t do this anymore, I want to quit,” and it’s always like, “You feeling like you want to quit? Take your head up and hire a new VP of sales, it will help.”

You know it will like, it’s like very like tactical and actionable, and I’m like, “You’re right, I do need a new VP of sales,” then I’m like, “We’re not B2B,” but I’m like, “I need a new marketing person,” so, like he just gives you very, he makes you feel like you’re not alone and he’s been through it and so it’s kind of like a therapist without, that I don’t actually have to talk to.

Rajaraman: Amanda this has been incredible, you were candid about all this stuff and you were just a great guest, so thank you for joining us here today.

Bradford: This was fun, thank you guys.

Rajaraman: We’re going to do the-

Kaykas-Wolff: We’re going to wrap up now, and then we’re going to have our online dating story in a minute, so don’t leave just yet.

Rajaraman: Yeah. Don’t leave yet.

Kaykas-Wolff: But before we wrap up, if you don’t know, Sunil and I have been working together for the last couple of years on this podcast-

Rajaraman: It’s actually only a year, FYI.

Kaykas-Wolff: It feels like a couple of years that I’ve been working with Sunil on this podcast, and we really like hanging out with each other, so much so that we Tweet each other all the time, and we wanted to invite everybody here, if you like this podcast, to actually hop onto Twitter and hit up Sunil at subs01, he’s the first of all of the subs on Twitter, or hit me up at kaykas, K-A-Y-K-A-S, and let us know what you though about the podcast. If you think about other guests that you’d like to have on or hear from, or things that are in the bay area that are important topics for you.

Rajaraman: Put it another way, if you take a picture of this and tweet it out, we’d appreciate it, promo for the podcast.

Bradford: We can turn it into a singles’ mixer next time.

Rajaraman: A singles’ mixer. Almost important as a singles’ mixer is how you go back to the place that you hear this podcast and hear it, and write a review and rank us five stars, because when you do that, it’s actually going to help a lot more people find this podcast as well. Thank you all for being here, thank you to Betabrand for hosting us this evening, thank you to our producers, [inaudible 00:37:55] who helps us book all of our guests, and thank you to everybody here in the audience. Have a great evening.

Kaykas-Wolff: Lisa Fetterman, for introducing us to Amanda as well, our guest today.

Rajaraman: Yeah.

Bradford: Yeah Lisa.

Rajaraman: Yeah Lisa. Thank you everybody, one big round of applause, thank you to everybody.