
In this episode of Founder’s Story, Daniel sits down with Sergio Giles, CEO and Founder of Date Draft, to unpack why modern dating feels broken and how gamification might fix it. From swipe fatigue and ghosting to NFL-inspired “trades,” Sergio explains how he’s turning dating into a social, interactive experience designed to spark real connection.
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A
Thanks for having 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 realized and stuff is like, you know, the users, they don't really get a chance to interact with each other nonetheless, until they match. And then you got a chat, then see how that goes. So what I did is I developed Daydref, and I kind of approached it from, like, you know, I'm big into 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. I just kind of use that concept and use that concept throughout the whole app, it's like, you know, you, you drop somebody, they can end up in, in certain rounds, and certain rounds could actually correlate with the different value of 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, so on and stuff, they end up in different rounds. And I figured that would be one of the best ways how to match people because they have that similarity of like interests and education, stuff like, and things of that matter. Yeah. With the day draft, basically, it's just, it's. It opens up the door for a little bit more fun because we have something that's called a trade room.
B
Yeah. So tell me about this trade room. I mean, it's, it's very interesting mixing this 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.
A
Yeah, well, you know, well, you know, pretty fortunate to actually come up with the idea, but like, once again, and relating in relation to sports, even after, you know, a team draft a player or whatever. Kiss me. They end up trading them because that person doesn't actually fit the bill or what they're looking for. And as same concept with dating, except for, you know, we created this, 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 case being, all of a sudden this person ghosts you. Well, if this person goes here, 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, you know, 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 on 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 ones that you want to trade.
B
I'm fascinated by this. What was the aha moment for you where you're like, okay, this is really gonna work? Like, did you test this out? Did you test it out yourself? Did you get 30 people? What was your, your beginning marketing strategy that. That really helped you create this aha moment that this is something that needs to be added?
A
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 Day Draft, just talking to people and, and realizing that some of the issues that they were going through. So it's like, you know, it's pretty much like a, a one shot time for everybody after you match with somebody and then you have to start the 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 the 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 each other on a dating app besides just, you know, just matching and chatting.
B
I know a lot of people want to create an app and I've heard that zero to a hundred 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?
A
Oh, you tell my as in 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 they first sign up, that's one. And 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 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's 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, you know, it's kind of like for the person that's actually trading other person, it's kind of like they're playing matchmaker.
B
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 just for the app overall?
A
Well, I mean, one of the key points that we use for marketing, advertising and stuff is it's more of a new social spirit experience. So it's a little bit of social adding in there with that trade room, you know, but it's just a little bit different concept with the whole ideal of, of, you know, giving your users more of a, a gaming type ideal of dating instead of it just being plain old boring dating.
B
So is that how you would differentiate yourself between like the swiping? Because it's. I, I guess the swiping was maybe the first gamification, right, That, I guess that 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?
A
Yes, I do, I do think that especially when it comes to dating, it needs to be more of a game like environment to just, to be able to add some fun. I mean, some people, they, they look at dating as very frustrating or very taxing. You know, I mean, every time you, you, you meet somebody new, it's, it's a, it's, it's the same old, you know, where you from, you know, and the whole array of different, like, questions that go along with dating. But yeah, I mean, don't get me wrong, we got to swipe on our platform as well. I mean, there, 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 it a little bit more innovative to like, entice people to want to date more?
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A
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, some of the editors actually called it like the fantasy football or dating. Had no idea where that came from but hell sounds good. But yeah, it's, it's a very unique concept and you know, we test it out and it's actually pretty fun. It has, 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.
B
So there you go. You're the fantasy football of dating. Take the tagline, right? Whatever tagline you're given seems, oh yeah, that's something that makes you more memorable. What was some of the, what were the users saying or what have they been saying? What have you seen since you started this?
A
Well, we just recently launched so we haven't gotten that much feedback but some of the feedback that we have gotten a lot of members, they are very excited about it and they, they really love the, 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, the dating app and then you know, see the type people that they're interested in and see if they could actually match with, with you know, one of those other users that they match with.
B
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 it in other countries, but how are you looking at this in the future?
A
Well, to be honest with you, Danny, 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. And then. Then we usually meet and. And see what. See what steps that we can take to actually enhance the user's experience, not just here in the US but also overseas.
B
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, day 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, the 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 Day Draft?
A
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, you know, I met this one person, didn't work out, so I asked her trade 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 be the pinnacle, whatever. You know, I understand the giants out there, Tinder, Bumble 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 Day Job to be known for, you know, actually changing the way that we date online by introducing the trade room.
B
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?
A
Well, we just hoping to curve ghosting a little bit more and actually. And actually helping people create more of a real connection. That's one of the positive features about the trade room. It's like you get to play matchmaker with the other members and 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 when you watch the NFL draft or whatever case may be. We got some pretty wild imaginations over here and we're looking forward to implement on the app later on this year.
B
We were talking earlier about 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?
A
Well, I'll tell you what's an ongoing learning process is understanding the actual. The members that are actually going to be signing up. I mean, dating is a. Is a whole psychological thing anyway. And you know, by actually offering a service for them to do dating, whatever case 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 an got to give him a shout out. He helped with the development of the trade room. We, 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 actually leave like a comment about this person were 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 some, something derogatory about another person that they already match with. So we just kind of left that out of it and just, you know, just like regular matching, man, you got to kind of figure it out, you know, by yourself on if this person is going to be a good match for you or not or compatible with you.
B
A lot of, I mean the whole dating, the science, the psychology, it's, 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.
A
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 if anybody in my company or organization stuff, they can definitely go to the website daydraft.com the fact.
B
That you could get that website's 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, 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.
A
All right, thank you, Daniel. I appreciate your time, man. And yeah, we could get some people to join the draft. Day or night. VRBoCare is here 247 to help make every part of your stay seamless. If anything comes up or you simply need a little guidance, support is ready whenever you reach out. From the moment you book to the moment you head home. We're here to help things run smoothly because a great trip starts with the right support. And hey, a good playlist doesn't hurt either. If you like the show, please take a moment to rate, review and subscribe. It really does help the show to grow.
B
Thank you for listening.
Founder's Story by IBH Media
Episode 309: Sergio Giles, Founder of Date Draft
Release Date: February 17, 2026
In this episode, host Daniel from IBH Media sits down with Sergio Giles, founder of the innovative dating app Date Draft. The conversation revolves around how Sergio is leveraging his passion for sports and gamification to transform online dating with new engagement models like “drafting” users and introducing the “trade room.” The discussion explores the psychology behind online dating, challenges faced by new app founders, and Sergio’s broader vision for changing how people connect.
"When you're dating somebody or searching for somebody, it's like you're drafting them. I kind of use that concept throughout the whole app."
"Depending on what they choose for their interest, education, so on...they end up in different rounds."
(02:23)
“If somebody ghosts you... you could actually place them in the trade room.” (03:23)
"It's kind of like a matchmaker...they've already matched with somebody else, so you know they're a real person." (04:48)
"It’s more of a new social spirit experience...giving your users more of a gaming type ideal of dating." (07:26)
"We just pretty much had to exploit some of our features that made us different from the other apps." (05:57)
“We suggest that you don’t [trade] too much, but it’s just more interactive.” (10:52)
“Dating needs to be more of a game-like environment—add some fun! People get frustrated or taxed with the same old questions.” (08:26)
"Some of the editors actually called it like the fantasy football or dating. Had no idea where that came from but hell, sounds good" (10:52)
"A lot of members, they are very excited about it and they really love the trade room." (11:52)
"We're just taking it as it comes...not trying to be too ambitious." (12:39)
"We'd like...for Date Draft to be known for actually changing the way that we date online by introducing the trade room." (13:40)
“We had this one concept that...the person 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.” (16:02)
"We're going to be introducing...more of a live trade. Kind of like when you watch the NFL draft..." (14:48)
On Innovating Dating:
"It's just another way to be able to interact with each other on a dating app besides just, you know, just matching and chatting." (04:48) – Sergio Giles
On What Success Looks Like:
“I'm hoping somebody will say one day, ‘I actually traded up for my wife.’” (13:40) – Sergio Giles
On App Store Strategy:
“If anybody in my company or organization stuff, they can definitely go to the website daydraft.com” (17:52) – Sergio Giles
This episode highlights how reimagining the user experience by gamifying the dating process and creating interactive features can reinvigorate a sector often criticized for staleness and frustration. Sergio’s playful yet thoughtful approach, epitomized by the Trade Room and his ambition to challenge industry giants, offers a fresh take on how technology can facilitate meaningful relationships.
Final Thought:
If you’re tired of “swipe fatigue” and want to see what “trading up” in dating might look like, Date Draft is one to watch.