In this episode of the Knup Sports Show, Ryan Knuppel sits down with Jonathan Gruber, founder of Loserball, to discuss his unique take on fantasy sports. Jonathan shares how Loserball flips the script by having players root for losing teams rather than winners, making for a fun and unconventional way to enjoy the game. They dive into the inspiration behind Loserball, the challenges of creating a fantasy app, and what the future holds for this innovative platform. Tune in for a fresh perspective on fantasy sports and the surprising joy of rooting for failure!
Ryan Knuppel
Hey, what’s going on, everybody? Ryan Knuppel here. Episode two hundred and thirty four of the Knup Sports Show. Hope you’re doing really well today. Everything is good here. We are football heavy. We are in the middle of football season now, or the beginning of football season. But week two is amongst us as of recording. It’s Thursday night football coming tonight. So super excited for that. Hope you’re all doing really well and enjoying the beginning of football. I got another amazing guest here for you today. I’m super excited to dive into this show and understand a little bit about what they are up to.
But first, if you’re heading to SBC Summit in Lisbon, that is only a couple weeks away. So if you’re heading to that event and don’t have tickets yet, make sure you use our promo code. We are media partners. You can get a nice little discount, get a little money off if you haven’t got your tickets yet. I won’t be going, sadly. I will not be making Lisbon, but going to GTE. I’ll be at GTE in October. So I would love to see any of the audience there. Make sure to shoot me a message and we can connect.
All right, that’s all for the beginning housekeeping stuff. Let’s go ahead and bring on our guest. I’m super excited to talk to Jonathan Gruber of Loser Ball today.
Jonathan Gruber
I’m good. I want to go to Lisbon.
Ryan Knuppel
I do too. I wish I was going to Lisbon. I’m not going, but it sounds like an amazing show. Never been to Lisbon, actually.
Jonathan Gruber
Oh, it’s great. It’s a great place. Portugal is lovely. I’m sure this time of the year also. It’s reasonably priced also.
Ryan Knuppel
Yeah. That’s refreshing to hear this time. Everything doesn’t seem reasonably priced these days. Everything’s expensive. Everything.
Jonathan Gruber
Exactly.
Ryan Knuppel
Anyway, Jonathan, excited to dive in here. How you doing, my friend? Whereabouts are you living? Are you in the United States?
Jonathan Gruber
I am. I am. I’m in Silver Spring, Maryland, outside of Washington, D.C.
Ryan Knuppel
Amazing. I’m down in Orlando, Florida, here, living the Florida dream. I guess supporting my Gators, who, after week one, they were brutal. Bounced back last week, but not a real good team. So anyway, we won’t get into that. They were losers the first week, which we’ll play on words for what we’re going to get into here in a bit.
But Jonathan, let’s dive into you. Tell us a little bit about yourself. Let us know what makes you tick, what you do for work, and kind of leading up to Loser Ball and what made you get going with that.
Jonathan Gruber
Sure. Well, it seems like growing up in New York and being a Red Sox fan and going to Syracuse that my whole life has been leading to Loser Ball. We, you know, I’ve had—I mean, the Red Sox have done well, but all you can remember as a fan, no matter how many championships your teams have, it seems that it’s the losses and the heartbreaking losses that really stick with you more. Somehow, maybe that’s a metaphor for life. So we wanted to take the concept of losing and just sort of all these wacky things that happen in football and turn it on its head and root for that. Not just be like, oh, that’s a bummer, but embrace the craziness.
It all started probably twenty five years ago. A friend of mine and I decided that fantasy was just too complicated and too serious for us. So we said, let’s pick a team and whoever loses the most games is the winner, and you’ll win some sort of swag, you know, some fleece or a stop sign or a rain poncho from that team. And so that was fun to root against teams. But what was equally as fun was the banter, the sports cliches turned on their head, like, ‘Oh, my team is the home field disadvantaged this week.’ Or, ‘He really brought his D-minus game,’ and just said it with a straight face. We like to say we’re the Monty Python of fantasy football.
Eventually, I wound up picking the dynasty that is the Cleveland Browns of about six, seven years ago, the Johnny Manziel years. And I had a three-peat. I mean, I won three years in a row. They had the perfect season. They lost all their games. And I went to Cleveland for the parade. And it was just awesome, even though it was negative five degrees. And I thought maybe there’s something in fantasy for this. And so I started noodling around, making it a little bit more detailed, not just winning and losing, but different categories of suckiness during the game. I came up with an algorithm and talked to actuaries. And so I had something in place.
Then COVID came, so that kind of put a halt to things. And I guess a couple of years ago, I was like, let me see if I can make this a go. So I went to the Fantasy Sports and Gaming Association conference in Las Vegas in February and just met some folks. It’s a great group of people and kind of a more intimate conference, not like SBC. It’s got a different vibe. And I tried it out and people didn’t laugh me out of the room. They were like, ‘Maybe it’s been kind of done.’ I was like, ‘No, I don’t think so.’
You know, sometimes there are all sorts of booby prizes for people who are trying to win but come in last place. This is not what we’re doing. We are trying to pick the losers.
Ryan Knuppel
Jonathan, you’re making my job easy here. You’re making my job easy. I don’t have to ask the questions. You just explained it all.
Jonathan Gruber
You’ve done two hundred and thirty three episodes before this. I’m sure you’ll find something.
Ryan Knuppel
I’ll find something for sure. I was going to mention a couple of those names that you mentioned were on like episode ninety eight or something. I look back real quick. Ed Moad and Rick Wolf were both on the show back in like three, four years ago. So it’s crazy. The full circle of people in this industry.
And, you know, you mentioned FSGA, and they’re doing amazing things over there. And just, I love the people of this industry and just getting to know everyone. So really cool circle that you’re now a part of and really dove into. My question, I guess, is a little more personal. Like, did you ever dream you would be an app owner or a website owner, an app owner for lack of better terms? I mean, is that something that you were like five, ten years ago? Like, man, that’s what I’m going to do or that’s what I’m going to have in my portfolio?
Jonathan Gruber
No, no. I’m a documentary filmmaker by trade. And, you know, we’ve done websites for, you know, for our films, but that’s more informational. But I did find that there are some similarities to creating an app with creating a film. And that’s sort of prioritizing what’s really important to get to the MVP—the minimum viable product.
Similarly, what do we need to get to our rough cut? What’s really important to show or to have? And then moving forward, how do we have our short-, medium-, and long-term goals fulfilled as we move forward? So those are similarities. The difference is that with a film, when you show it to people—
Jonathan Gruber
—people aren’t expecting things to not work. They’re like, it should look good. It should sound good. Whereas with an app, people are much more forgiving, and they know there’s going to be updates. They know we’re working on it. So that actually takes a little bit of the pressure off. Obviously, there are critical bugs, there are issues you’ve got to fix—if it’s not working, people aren’t going to come back—but around the edges, you can do some work. So it’s been really interesting and really fun. It’s been a learning curve for sure. Again, having guys like Rick and Ed, I mean, they’re brilliant at what they do. Rick on the product side, Ed on the marketing side—just learning so much and learning about this industry, learning all this terminology that I was not aware of. And, you know, in some ways it doesn’t apply to us because we’re not doing traditional fantasy. We’re doing it in our own way. Next year, we do plan to expand. But I’ll let you—I’ll wait for that question.
Ryan Knuppel
Well, that was next! Thanks for letting me participate! That was next though. So obviously, you launched around football season, got NFL rolling. Expansion is most likely in the works. So what sports are we heading into? What’s the expansion plan look like?
Jonathan Gruber
Sure. So thanks, that’s a great question. I’m excited about next year. This year, the plan is to build up the user base and get people excited about playing Loserball, build up the brand name. And it seems like we’re making some good headway in just a short period of time. Next year, we’re going to introduce DFS-style games with entry fees and cash prizes, and that will be done all in the same voice and brand of Loserball. So, you know, very different than what people are used to in DFS.
Shortly after that, I mean, or, you know, it’s hard to say when we’ll get to each stage, but we definitely want to expand this concept to baseball, to basketball. Soccer—my, you know, I don’t know, my real goal out there is to get to India, where there’s two hundred million fantasy cricket players. And once I figure out how to play cricket, we can do a Loserball version of that. So that’s kind of the vision for where Loserball is and where it’s headed.
Ryan Knuppel
Is it still called a ball? I’m so uneducated in cricket. Is that a ball? It is, right?
Jonathan Gruber
I was in South Africa actually for, I think it was the Cricket World Cup, and they took a three-day test match and they shrunk it down to half an hour for TV. And I was able to understand it, but that part of my brain seems to have, you know, disappeared because I can’t remember what I remembered back then. But yeah, no, they call it something else, don’t they? They don’t call it a ball. I don’t know, actually.
Ryan Knuppel
My brain went to like, I don’t even know if that’s actually called a ball. But anyway, it would work. It would still work. But that’s an amazing vision. That’s an amazing vision. I actually played cricket one time, and that’s what’s funny. Like I had some friends that were really into cricket, and I tried to play. I attempted to play, and I’m like, I have no idea what I’m doing. I’m like swinging like a baseball bat. I’m like, this is not going well. But anyway, that’s another story for another day.
Jonathan Gruber
No, I mean, it’s a huge fan base and very passionate about it. We started with North American football because that’s kind of the biggest game in town, literally, here. And I actually know how to play, so it’s easier.
Ryan Knuppel
So free to play this year, free to play right now. What’s the traction looking like for you guys? I mean, obviously, you’re very young. You’re just getting rolling. I definitely have seen you guys in the press, and you’re making some noise out there, so congrats on that. So congrats on the early success. But talk a little bit to that. What type of traction are you getting from people? And are they having fun with it?
Jonathan Gruber
Sure. Yeah, I mean, our user base is about a thousand. I mean, we just started, so it’s not nothing, but we’d like to obviously grow that a lot. That’s part of getting it out there with the marketing. But I think people that—we haven’t kind of dove into the stats, but a little bit—people are spending time on it. We’ve got… it’s more than just playing the picking the teams and then watching the games. It’s also there’s all this content online, all this research that we’ve done, there’s team previews, there’s kind of understanding each of the categories.
And, you know, I’d say really Fantasy Alarm and Better Sports Network, to their credit, they’ve really done some strategy. It’s like, okay, the Niners are maybe not a team that you want to pick, but who are they playing against? You know, maybe that’s who you want to take. And so, you know, it’s kind of cool. It’s like, you know, this is our baby and it’s born, and you don’t really know how it’s going to grow up. So there’s lots and lots of content online where people can not only read about it but kind of laugh about it. You know, it’s just like our voice, the way we’re talking about it.
Ryan Knuppel
You’ve mentioned that word many times, which I, it’s refreshing, right? Fun. You know, this is meant to be fun. Obviously, it’s a business for you, and it is serious. But, you know, sometimes I think in fantasy sports and sports betting, the more we get into the numbers and all this stuff, we all take it really, really seriously, and it becomes almost too serious sometimes, right? So I love the fact that you’re kind of embracing the fun. You’re trying to inject that fun back into the whole dynamic of fantasy sports. So that’s refreshing to see.
Jonathan Gruber
Yeah, I want to always remember that. Even though I’m talking about the strategies and the, you know, who are you going to pick and who don’t you like and what’s the handicap? That’s all in there, you know, so people can do it. But ultimately, it’s about watching the game and rooting in a completely, completely different way, which is bizarre and fun and silly. I’ve had all these anecdotes about people watching, picking a team, and the kicker like, ‘Oh, he made the kick.’ It’s just like…
Ryan Knuppel
Yeah, there’s so many ideas. I’m sure you guys have so many game ideas and just different marketing ideas that can go around this. That’s the beauty of it. The other beauty of it is there’s nothing done like this, right? I mean, it’s a brand-new idea, and there are many ideas that have been done over and over and over in better ways. This is a brand-new idea. So, yeah, very cool, very cool. Congrats on the beginning stages of what looks to be a pretty fun product, Jonathan.
Jonathan Gruber
Thank you. I appreciate it, Ryan. We’re excited about it. Thanks for having us on and helping us talk about it a little bit. Again, it’s easy to get in. Sign up, pick your teams, you’re done. That’s it.
Ryan Knuppel
I want a reverse Survivor. I’m sure you’ve already thought of that one, but I want the reverse Survivor because the Survivor, you’re always picking that one winner, but let’s pick the one loser each week and see how long we can last picking one loser each week.
Jonathan Gruber
Well, I got to say, picking losers is, you know, just like picking winners, it’s hard. It’s not so easy to pick losers.
Ryan Knuppel
No, I know. Look at the Bengals and the Patriots. Survivor wasn’t easy. It’s never easy. There’s always like forty percent of the people out after week one.
Jonathan Gruber
Exactly. It’s just, you know, it’s a new way to play. Fantasy has been going on for a long time. And I’ve always thought of myself as a contrarian. I mentioned growing up in New York, being a Red Sox fan. It seems that Loserball was always in my DNA.
Ryan Knuppel
Amazing. Well, what did we miss? Before I let you off the hook here, Jonathan, anything else you wanted to touch on or talk about before we jump off here?
Jonathan Gruber
Thanks. I think I’ve gotten all my points in repeatedly. Just that it’s easy to play, it’s hilarious. I think that’s really what we love, especially recapping some of the week one blunders. It’s like, oh, they gave up a touch—the Bills gave up a touch.
Tonight, it’s the Bills vs. Dolphins. So we’re like, we did a little write-up. Will there be some more bodacious Bills blunders or delightful Dolphins disasters? We’re having fun with it, so we encourage everyone to jump in.
Ryan Knuppel
Well, I guess lastly here before we go, you have an amazing team behind you, right? You have an amazing team of support. But if there’s anything you’re looking for, anything you need, there may be somebody watching that’s like, oh, this is a cool idea. What ask do you have of the audience? What do you need help with? What are you looking to do over the next six months that you might need help with?
Jonathan Gruber
Oh, well, that’s great. That does make me think of something. Well, two things. One is that, you know, when people sign up—because we’ve just launched—we’ve got, you know, a way to contact us if something’s not working. Inevitably, you know, every day we’re meeting, and I’m like, what are the bugs? What are the little things we can improve? What’s critical? What can we push aside?
But also, we’re a startup and we’re bootstrapping. So, you know, this is a serious venture. And if people are, you know, are interested, you know, we’re—investors are always welcome. So I appreciate you mentioning that.
Ryan Knuppel
Awesome. All right, Jonathan. Well, that was an amazing show. Really appreciate you coming on. I can’t wait to circle back around in a year and get the update. So good luck, and thank you again for joining me.
Jonathan Gruber
Thanks. And I appreciate you letting me prattle on without…
Ryan Knuppel
Awesome. Well, good luck this week. Give us one loser. Who’s going to lose this week? Do you have a loser in mind in the NFL?
Jonathan Gruber
I’ve been looking at the handicaps. I think the Raiders. They’re the loser of the week? The Raiders, yeah. They have a solid, solid team. And, yeah, they know what it takes to lose.
Ryan Knuppel
Sorry, Raider fans. You heard it here first. It’s going to be a rough week for them. All right, Jonathan. Take care. Thank you.
Jonathan Gruber
Thanks, everybody.
Ryan Knuppel
All right. That was Jonathan Gruber of Loser Ball. What an amazing show. Episode two hundred and thirty four in the books. Hopefully that made some people smile and, you know, just really a refreshing look on the world of fantasy sports that we all know and love, right? So. Pretty cool product. I know they’ve been making some noise and got a great group of people behind them as well.
If you do want to get a hold of him, we will put the links and all that stuff in the show notes, so don’t worry about memorizing it all. We’ll put it all out there, and I’ll have contact info for Jonathan out there as well.
Okay, I think that’s it. Again, SBC Summit—remember that one—that’s in two weeks. That’s it for me. I’m Ryan Knuppel at KNUP. You can find me on all the channels. Thanks again for watching. Until next time, take care. Stay safe. Have a good one. Bye-bye.
Relevant Guest Links
- Learn more about loserball on their website.
- You can connect with Jonathan Gruber on LinkedIn.
More Knup Sports Links
- I refer to Knup Sports often in my show. That’s our sports passion site. Check out KnupSports.com here.
- If you are looking for sports content services you can find more information on the Knup Solutions website.
- Listen to more episodes of the Knup Sports Show.
- Want to be a guest on our show? Setup a time that works here.
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