Founder's Story - The Dating App Rewriting the Rules of Love | Ep 309 with Sergio Giles Founder of Date Draft

Episode Date: February 17, 2026

Sergio Giles joins Founder’s Story to discuss why so many people are frustrated with traditional dating apps and how Date Draft introduces a new sports-inspired model to online dating. Drawing from his NFL fandom, Sergio reframes dating as “drafting,” “scouting,” and even “trading,” creating a more interactive, gamified experience that moves beyond endless swiping and repetitive chats. Key Discussion Points:Sergio shares how his own experiences on dating apps revealed a major flaw: users don’t meaningfully interact until after matching, and burnout quickly sets in. That insight led to the creation of the “Trade Room,” a feature that allows users to trade matches and act as matchmakers, adding a social layer to dating. The app assigns members to different “rounds” based on interests and education, using an algorithm to create compatibility tiers. Sergio also discusses the psychological tightrope of building a dating product, balancing innovation with responsibility while avoiding features that could create negativity or defamation. Takeaways:Date Draft positions itself not just as another dating app, but as a new social experience that blends gaming psychology with matchmaking. Sergio believes the future of dating apps must be more interactive, more fun, and less repetitive to reduce ghosting and swipe fatigue. Instead of just asking users to swipe and start over repeatedly, the Trade Room gives them new ways to connect and re-engage. His long-term vision is simple but bold: to be known as the app that changed how people date online. Closing Thoughts:Sergio’s journey highlights how founder insight often comes from personal frustration and pattern recognition. By studying user behavior and reimagining dating through the lens of sports drafts and trades, he’s betting that connection improves when interaction feels dynamic rather than transactional. Whether Date Draft becomes the “fantasy football of dating” or something even bigger, it’s a bold attempt to rewrite the playbook on modern love. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

So Sergio, you and I have had some great conversations running up to this discussion we're going to have. And I'm super fascinated with, one, everyone I know who's in the dating scene complains about how terrible it is, how terrible the apps are. Just the experience is bad. And then you have on the other side, I feel like because of a lot of dating apps, there's so many choices that people never want to settle down. So it almost seems like it's not really creating a good environment for the dating scene. You, though, having a sports background are bringing that with date draft. What made you say, I'm going to take this background and I'm going to move into the dating app scene? Thanks for helping me on, Daniel.

First and foremost, when it comes to the dating scene, I've been on a few dating apps myself. And what I realize and stuff is like, you know, the users, they don't really get a chance to interact with each not unless until they match and then you got to chat and then see how that goes. So what I did is I developed daydraft. And I kind of approached it from like, you know, I'm digging the sports, especially NFL. And I was just looking at like, you know, when you're dating somebody or when you go to date somebody or you're searching for somebody, it's like you're drafting them. So I just kind of use that concept and use that concept through a whole app. It's like, you know, you draft somebody they can end up in certain rounds.

and certain rounds could actually correlate with the different value, if a high value person, whatever it can be. So I actually came up with an algorithm so that when the members sign up, depending on what they choose for their interest, education, and so on, they end up in different rounds. And I figured that that would be one of the best ways out to match people because they have that similarity of, like, interests and education stuff and things of that matter.

Yeah, with the day draft, Basically, it's just, it opens up the door for a little bit more fun because we have something that's called a trade room. Yeah, so tell me about this trade room. I mean, it's very interesting mixing the sports draft system into the dating world. I almost think like, why did somebody else not think about this before? But yeah, tell me about that. Yeah, well, you know, well, you know, pretty fortunate they actually come up with the idea. But like, once again, in relation to sports, even after, you know, a team draft a player or whatever,

kids to be, they end up trading them because that person doesn't actually fit the bill of what they're looking for. And it's the same concept with dating. And so for, you know, we created this, this trade room and basically how the trade room works, if somebody ghosts you, like, let's say you match with somebody, you start chatting, everything going good for, you know, a good few weeks, whatever kids to be. And all of a sudden, this person ghosts you. Well, if this person goes you, you could actually place them in the trade room. And how that works is like, if I'm on the app and you're on the app and we're pretty much in the same area

and I'm looking to meet somebody and I'm tired of swiping. I'm tired of exploring, you know, and I just want to see, you know, what else is out there. I can actually go in the trade room and I can select you to trade. If you accept to trade with me,

I get to see everybody that you match with, especially the ones that you want to trade. I'm fascinated by this. What was the aha moment for you where you're like, okay, this is really going to work. Like, did you test this out? Did you test it out yourself?

Did you get 30 people? What was your beginning marketing strategy that really helped you create this aha moment that this is something that needs to be added? Well, I mean, just conversating with people, especially like when I was on some of the other dating apps and stuff, you know, before I created date draft, just talking to people and realizing there's some of the issues that they were going through. It's like, you know, it's pretty much like a one-shot time for everybody after you match with somebody and then you have to start a process all over again.

Well, with the trade room, it's kind of like a matchmaker in a sense. You know, for the people that you could select or that you could pick in a trade room, they've already matched with somebody else. So, number one, you know they're a real person. So you don't have to worry about that because somebody else has already matched with them and had a conversation with them. But, I mean, it's just another way to be able to interact with. with each other on a dating app besides just, you know, just matching and chatting.

I know a lot of people want to create an app and I've heard that zero to 100 or zero to a thousand users is one of the hardest moments in the, in the sphere of marketing for apps. It's really getting that beginning validation. What was the strategy for you that worked in the beginning? Oh, you tell my eyes and like, you know, populating the app with our marketing strategy. Well, I mean, basically how I looked at it was like, you know, we just pretty much had to exploit some of our features that, you know, made us different from the other apps. The different rounds that members actually get into when you first sign up, that's one. Changing the whole, like, psychology of it by saying instead of matching, you're drafting each other or scouting to actually search for somebody.

But the whole idea of the trade room is just something I just came up with. I was, you know, it was like, you know, during the draft season, the NFL, it just popped me in my head. Like, you know, we're out here drafting people to date. That's basically what we're doing. We're scouting. And it was like, you know, eventually, you know, that relationship might, that connection might work out. And it might not. But it's like, what do you do afterwards?

You know, a lot of people get burned out on the dating apps of going through the same routine. So that's why we came up with the trade room and stuff where you could actually go in and like, you know, become. And it's kind of like for the person that's actually trading that a person, it's kind of like they're playing matchmaker. When you think about just marketing the app overall, not just the trade room part, what was something that's worked for you to really get the word out to gain more users and stuff for just for the app overall? Well, I mean, one of the one of the key points that we use for marketing, advertising. and stuff is it's more of a new social experience. So it's a little bit of social adding in and there with that trait room, you know, but it's just a little bit different concept with the whole ideal of, you know,

giving your users more of a gaming type ideal of dating instead of it just being plain old boring dating. So is that how you would differentiate yourself between like the swiping because I guess the swiping was maybe the first gamification right that I guess I did gamify and then you think that people are on to the next level of gamification because they're they're kind of burnt out from that action and now they're looking for something that is more interactive is that is that how you see apps in general moving forward is they need to be more gamified and more interactive yes I do I do think that especially when it comes to dating it needs

to be more of a game-like environment, just to be able to add some fun. I mean, some people, they look at dating as very frustrating or very taxing. You know, I mean, every time you meet somebody new, it's the same old, you know, where you're from, you know, and the whole array of different, like, questions that go along with dating. But, you know, I mean, don't give me. wrong, we got this white on our platform as well. I mean, it's a great concept. It's an easy way for them to actually, you know, see the different people or the different members on the app. But at the same time, it's like, you know, what else can, what else can we do to make a little bit more innovative

to, like, entice people to want to date more? So, you know, that's why I came up with the whole concept of the trade room. I mean, some of the publications that we've been featured in, And some of the editors actually called it like the fantasy football of dating. I had no idea what that came from, but, hell, sounds good. But, yeah, it's a very unique concept. And, you know, we tested out, and it's actually pretty fun. It has a little bit more spark to dating because, I mean, you can pretty much trade, you know, as much as you want. But, you know, we suggest that you don't.

But it's just a fact of matter that, yeah, it's just more interactive. So there you go. You're the fantasy football of dating. Take the tagline, right? Whatever tagline you're given. It seems like that's something that makes you more memorable. What were the users saying or what have they been saying? What have you seen since you started this?

Well, we just recently launched. So we haven't gotten that much feedback, but some of the feedback that we have gotten And a lot of members, they are very excited about it. And they really love the trade room because it gives them that other option of just sitting there and swiping where they could actually, you know, interact with another member of the dating app. And then, you know, see the type of people that they're interested in and see if they could actually match with, you know, one of those other users that they didn't match with. So as we know, we're so globally connected with. all social media, internet. How do you look at international expansion?

I know you have people that are downloading in other countries, but how are you looking at this in the future? Well, to be honest, we're just taking it as it comes. You know, we're not trying to be too ambitious. We're just pretty much sitting back, seeing how everything flows with date draft. And then we usually meet and see what steps that we can. can take to actually enhance the user's experience, not just here in the U.S., but also overseas.

So when you think about what is it that you want this to be known for in the future, what is it that you hope in a few years from now people look back and say, date draft is X because I think in the past it was always, you know, like I met my wife on blank or I met my partner on blank, right? That was kind of the gauge of the success of many of these apps. But I know generations have changed, right? Like, I'm sure the culture, dating, the habits are changing. So maybe that's not always the measure of success.

But how do you see the measure of success for date draft? Well, you know, we're just hoping in the future that we could like, you know, start getting some feedback or like some actual reviews saying that, hey, you know, I actually traded up for my wife. You know, I met this one person didn't work out. So I actually traded up and that's how I met my wife or that's how I met my husband. You know, but yeah, but I mean, basically, you know, everybody that has an app that comes out, they want to beat a pinnacle, whatever. You know, I understand the Giants out there, Tender, Bambol, hinge, and, you know, plenty of fish and a few others and stuff. I mean, yeah, if we could actually step in the, on the front porch with those big dogs and compete with them, that's fine. I just would like for a day job to be known for, you know, actually changing the way that we date online by introducing the trade room.

So if you change the way people date, what do you hope that that will accomplish? Do you feel that just whatever is out there right now, just people are not making the right connections or like why, what is the biggest problem that you feel like you are solving here? Or even just the problem you hope to change. Well, we're just hoping the curve ghosting a little bit more and actually and actually helping people create more of a real connection. That's on the positive features about the trade room. it's like you know you get to play matchmaker with the other members and you know things of that nature

i mean that's basically what we're looking to change and introduce that we have other innovative features involving the trade room and stuff that we're going to be launching as the app continues to grow probably later on this year we're going to be introducing one of the other features which is actually going to be more of a live trade kind of like you know when you watch the NFL draft or whatever it may be yeah it's um Yeah, we got some pretty wild imaginations over here, and we're looking forward to implement on the app later on this year. We were talking earlier about like the Super Bowl and other games that people bet on.

Maybe in the future there might be this predictive market around betting on who's going to continue dating. That would be quite hilarious. Like, who do you think is going to continue to date on these apps? When you look at the challenges that we face as founders, What is something that, a lesson that you've learned so far creating this? Well, I'll tell you, what's an ongoing learning process is understanding the actual, the members that are actually going to be signed up. I mean, dating is a whole psychological thing anyway.

And, you know, by actually offering a service for them to do dating, whatever kids to be, we have to have some kind of psychological understanding exactly, you know, how they would respond or whatever. I mean, it's kind of borderline because like when we're, when we, when I first came up with the, the trade room and talking to some of my developers, shout out to Muhammad Ons. Got to give him a shout out. He helped with the development of the trade room. We had this one concept that, you know, before you actually select somebody that you

want to match with through the trade room, that the person can actually leave like a comment about this person, we're like, ah, no, I don't want to do that. That's borderline, like defamation that could come back if somebody says something wrong about or something derivatory about another person that they already match with. So we just kind of left that out of it and just like regular matching, man. You got to kind of figure out by yourself on if this person's going to be a good match for you or not or compatible with you. A lot of, I mean, the whole dating, the science, the psychology, it's very fascinating. That's why I enjoy watching shows like Love is Blind or Love Island, like all these shows, it's very, you know, they always say it's like a social experiment.

I find it very fascinating to study human behavior and why people do what they do. But if people want to get in touch with you, they want to, they want to download the app. How can they do so? Oh, yeah, they can download. It's available on Google Play and on Apple through the App Store. So it's available on both platforms. And yeah, if they want to get in touch with anybody in my company or organization and stuff, they can definitely go to the website, date draft.com.

The fact that you could get that website is amazing. I mean, that's a really good URL. But Sergio Jow's Date Draft. I enjoyed the conversation today. I can't wait to hear what data, what information, what you find out in the next few years around how the changes are with dating it and how this app and what you're doing will completely maybe it'll change the way society looks at things just as like you said bumble and tinder have done as well but thank you so much for joining us today

all right thank you then i appreciate your time man and uh yeah we could uh get some people to join the draft