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Knup Sports Show (#244): SportsGrid CEO Jeremy Stein on Video Content and Casino Expansion

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Jeremy Stein of SportsGrid Joins the Knup Sports Show

In episode 244 of the Knup Sports Show, host Ryan Knuppel sits down with Jeremy Stein, the CEO and co-founder of SportsGrid. This episode takes listeners on a journey through Jeremy’s unique background, the early days of daily fantasy sports, and how that path led him to build one of the most dominant live sports betting and casino content networks in the industry today.

From Venture Capital to Daily Fantasy to Founding SportsGrid

Jeremy Stein kicked off his sports journey by leaving a secure job at Metamorphic Ventures in 2015 to play daily fantasy sports full-time. It was a bold move that came just before significant regulatory changes, but Jeremy found success and, more importantly, learned where the industry was heading. Soon after, he connected with Lou Mayone, and together they built SportsGrid, a company that would pioneer the live streaming space in sports betting media.

With the repeal of PASPA and the explosion of legal sports betting, SportsGrid was well-positioned as a connected TV channel delivering 18 hours of daily live programming. The company quickly found success by merging strong content production with deep predictive data models. Jeremy’s early experience with DFS helped shape the foundation for SportsGrid’s scalable content engine.

What is SportsGrid and Why Does It Matter?

SportsGrid is a free, ad-supported streaming television (FAST) network delivering sports betting content. Available across 30+ platforms such as Roku, Amazon Prime, and Samsung TV+, SportsGrid dominates the market, owning over 35% share. In 2023, the network measured more than 240 million unique sessions—and it’s growing rapidly.

What sets SportsGrid apart is its efficiency. With just 32 full-time employees, the company produces 18 hours of daily live content with a cost-per-hour of around $2,150—covering everything from hosts to production to legal and operations. Jeremy highlights the company’s focus on repeatable formats, reliable talent, and strong infrastructure as the keys to scalability and success.

Why Casino Is the Next Big Focus

While SportsGrid began with a focus on sports betting, Jeremy explains how casino content has become the next major frontier. The company has invested heavily in producing casino programming, with partnerships and influencer deals featuring notable names like Paige Spiranac and Brian Christopher. The goal is to expand reach on platforms like YouTube, Instagram, and Kick, where casino content thrives.

From sweepstakes to regulated casinos, the market opportunities are massive. Jeremy believes that as more U.S. states legalize online casinos, SportsGrid will be ready to lead the content charge, just as it did with sports betting.

Content Strategy and the Power of Video

Unlike most media companies that leaned into SEO and written content, SportsGrid went all-in on video early—before it was the trendy move. Their bet on connected TV paid off, creating a significant moat that new competitors struggle to replicate due to distribution hurdles and technical requirements.

Social media is also part of their strategy, but selectively so. While sports content pushes through their main social channels, casino is getting a full-scale social push with a focus on user engagement and influencer partnerships.

Final Thoughts from Jeremy Stein

Jeremy offers advice to entrepreneurs that is simple yet powerful: “It’s always easier to keep going than it is to stop.” Starting a company is hard, and he acknowledges the mental and operational challenges. But perseverance often leads to success—as long as you stay in the game long enough.

With a focus on casino content, continued dominance in FAST streaming, and a lean yet effective team, SportsGrid is well-positioned for the next wave of growth.

Watch or Listen to the Full Episode

To hear Jeremy’s full story, his insights on content, casino, and connected TV, and the inspiring journey of SportsGrid, be sure to watch or listen to the full episode. Follow us on YouTube, LinkedIn, or subscribe to the Knup Sports Show wherever you get your podcasts.

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Full Transcript for This Show

Ryan Knuppel
Hey, what’s going on everybody? Ryan Knuppel here. Knup Sports Show episode 244.

Hope you’re all doing well today. It is Thursday, June 5th here. And it is an exciting day because we have NBA finals starting up tonight.

I’m super excited about that. I’m an NBA junkie at heart, so I love the finals. I love the playoffs.

Super excited to see what happens there. I think it should be a good series. I think OKC is going to pull it out.

But anyway, we’re not getting into the picks and predictions today at all. But Neup says OKC in six in this series. So we’ll see how that goes.

Hopefully you’re all doing well. We have another amazing guest today. I cannot wait to jump in and hear his story and kind of where he’s been to bring the product to where it is today.

So I’m excited to jump in there. And so without further ado, let’s go ahead and bring on our guest today. We have Jeremy Stein of SportsGrid.

Jeremy, thank you for joining me. How are you, my friend? I’m doing very well.

Thank you for having me. Awesome. I appreciate you jumping on here.

NBA finals I just alluded to in the intro. You have a team. You have a dog in the fight or no?

Jeremy Stein
Unfortunately, I don’t. So I like this finals because it’s two smaller market teams. I’m a Cleveland Cavs fan.

So I am actually rooting very hard for the Thunder. I would love to see the Pacers lose. It was tough.

It was really tough to watch the Cavs go down this year. I thought we had a really strong chance to make it to the finals. I think Oklahoma City looks largely unbeatable.

But it was very disappointing to give it on to the Pacers.

Ryan Knuppel
Yeah. Yeah, the Cavs, they really did. I wouldn’t say lay an egg, you know.

I mean, they had a great regular season. And it just happens, right? You run up against a team playing hot.

So anyway, this is not about sports here today. This is about you and SportsGrid and what’s going on with your product. So, Jeremy, give us a little background of you and kind of, I guess, your path, your journey, your history that kind of led you to starting SportsGrid.

Jeremy Stein
This dates all the way back really to 2015. In 2015, I began playing daily fantasy sports in a full-time capacity. I left a pretty stable job at the time at Metamorphic Ventures, which is an early-stage venture fund here in New York, to really kind of go out into the unknown.

Daily fantasy sports at that time, it was going parabolic, the market, right? I’d say 2015, 2016 were like really the heydays. And I started everything maybe about two weeks before Eric Schneiderman really dropped the hammer.

So it was kind of an interesting time. But I found a lot of success. I played for, you know, about 18 months.

And at that time, you know, things started getting a little bit more difficult, right, as things become more legal and really is kind of the venture capital dollars really stopped flowing into the ecosystem. The market got a lot sharper for a lot of reasons. And it was around that time where I had met my co-founder, Lou Mayone, and he had a lot of distribution.

I had a lot of predictive technology. And we had this thesis that, you know, sports media was largely data, right, especially in the context of sports betting. You don’t need, you know, a body or a team of people to predict tonight’s Yankees game.

And you certainly don’t need a lot of people to recap last night’s Yankees game, right? You just need a host who, you know, is intelligent, who can speak about sports and actually hold an audience. And if you feed them enough information, you should be able to get to a pretty good production.

And that’s really what we did. So we started SportsGrid in 2017. Before PASPA was repealed, we took the long-term view that sports betting was going to become legal.

And actually, my co-founder nailed this. He said within one year of us starting, sports betting would become legal. I didn’t believe it.

I thought that there was no way. I thought it was going to be, you know, at least a three- to five-year journey. But we really kind of timed it perfectly.

And the way that I like to think about SportsGrid is that it’s really a once-in-a-hundred-thousand-lifetime opportunity. I’m never going to find myself in, you know, 2018 with the right asset at the right time, not just sports betting, but also connected TV, because connected TV was really starting to take off then. At a time where the government just flips the switch and say, grow in ways that you never thought were imaginable.

And I think that, you know, we’ve really kind of taken advantage of that because here we are eight and a half years later, and we’re still growing it over a hundred percent year over year.

Ryan Knuppel
That’s amazing. That’s amazing. That’s a cool story.

And, yeah, sometimes business is right time, right place, and kind of jumping in at the right time. And it sounds like you really, really did. But having that vision is also something that’s super important.

So for those listening, I mean, SportsGrid, obviously, they probably have an idea of what you guys do. But let’s really narrow into, I guess, the site and the product and all the offerings that you guys offer and kind of at a high level. What is SportsGrid?

Jeremy Stein
So we are a connected television streaming network. We are the number one free ad-supported television channel in sports. So SportsGrid, we are currently producing 18 hours of live original video content on a daily basis.

That’s streamed on over 30 different platforms, everything from Samsung TV+, to Roku, to Amazon Prime. Effectively, you know, you turn on your television, SportsGrid’s there. And we have extreme scale within the category.

We own over 35% of the market. And last year, we did 240 million unique sessions that we were able to measure. And it’s growing rapidly.

You know, this year, we’re already pacing up 50% from an hours of viewing perspective compared to the same period last year. So we really have a big opportunity. And what we’ve really discovered here at SportsGrid is that we’ve cultivated a large audience that likes to gamble.

It’s not just related to sports. 90% of our audience is interested in retail casinos, social casinos, sweepstakes casino. And we’ve really started to go in that direction.

So, you know, about a year ago, SportsGrid started creating casino content. And we are quickly becoming the largest producer of casino content on the planet. And for us, it’s a way to not just super serve our audience.

It’s also a way to super serve our clients. Because, you know, sports books like FanDuel and DraftKings and MGM, they also operate online casinos. So it really allows us to touch the full lifecycle, both our customers and our viewers.

Ryan Knuppel
Very interesting. You know, you’ve said the word content many times. And I’m a content guy through and through and through.

But there’s so many definitions of that word. And what I want to really nail in with you right here I want to talk through is it’s like SportsGrid really took video content to another level before video content was cool. I mean, honestly, it was like, how did that how did you see that?

Because most people when they kind of jumped into this space were like, oh, we got to have, you know, articles and writing and all this stuff from a textual side. But you guys jumped right into the video side and really took that as that’s what we’re doing. And I’m just interested in that whole perspective of how you guys had that forward thinking on video back eight years ago.

Jeremy Stein
So it was really a white space. Like, if you look at the companies that are built around sports betting and gambling, they are what you said, right? They’re largely affiliate.

They’re largely SEO based. And it’s very, very competitive. There was nobody that was doing video at the time and connected TV was brand new.

Right. We’ve gone from literally people saying OTT over the top to fast free ad supported TV in that time. And you could get distribution.

When SportsGrid began, we were the only live fast channel in all of fast. It was just playback. So when I say playback, think like maybe like the two and a half men channel.

People that already have IP, they just put it on fast and they air it because it’s just extra dollars for them. We were the only ones that were actually creating live content. And back then it was very easy to get distribution.

There are a lot of platforms that were lighting up and they were taking all of the content that they could get because there were not many people doing this. And that really became a big mode for us because now there are over 2000 fast channels. We don’t need more of them.

So the platforms have really clamped down on getting distribution. I think it’s near impossible for those that are starting today and existing fast channels, even like SportsGrid, for us to get new distribution. If I wanted to light up a second channel, it would still take me six to nine months with a distributor.

And that’s already having the reputation that we have. That’s already having the technical ability and proving that we can do it. So it’s very difficult in this day and age.

And it’s really just kind of going to where that white space was. We’re not good at SEO. We know that.

We work with wonderful partners in the affiliate space and we’ve always done what works for us. And that’s connected television. We just continue to double down on video.

Ryan Knuppel
Well, props to you. That’s pretty amazing. And I’ll admit I’m a consumer of what you’re doing on YouTube TV.

So I’m watching you every day. But let’s talk a little bit about 18 hours of you said 18 hours of live content every single day. I think what you said.

Correct me if I’m wrong. Let’s just talk through the challenges of that. Let’s talk through the how do you execute that from 18 hours of content?

Why the day? Talk through that a little bit.

Jeremy Stein
You know, it’s interesting because if you actually look at all media companies, very few are producing that amount of video. And you’re talking about everything from CNN to ABC, the live broadcasters. So it’s really important for us to find repeatable formats and to also have a dependable roster of talent.

SportsGrid is a small business. We are only 32 full time employees. So you need a very large roster of talent to be able to produce that much on a daily basis.

So that was step one. Step two was also developing the right architecture and infrastructure to be able to deliver the feed. That’s incredibly important because you need to deliver stable feeds to the platforms.

Not only that, SportsGrid also does this in a way that is compliant with the FCC. Right. So we have closed captioning.

We have everything that is actually required to go linear. And we have gone linear in the past. We syndicated our network on linear channels and we have also syndicated shows even this past year on linear channels.

So we’re really flexible. And really what we have focused on our KPI is cost per video hour. So it costs us $2,150 per video hour to run the entire company.

That’s not just producing the content. That’s salaries. That’s legal.

That’s officer. And everything goes into that number. And really what we’ve done is we’ve built pretty much the most efficient content creation company on the planet.

I don’t know anybody that can create what we do for that cost.

Ryan Knuppel
Yeah. Yeah. I can’t even imagine.

That’s amazing. Let’s talk about the people a little bit. I pulled up the end of the shows.

So it looks like you guys are hosting many shows. So let’s talk a little bit about the shows that you’re hosting across all sports. I’m assuming you’re kind of very versatile in the sports that you’re covering.

But talk a little bit about the lineup.

Jeremy Stein
So we have a pretty stable lineup. Right. The way that we’re kind of architected is we have a core host for every single show.

And that’s repeatable every single day. And then we have guests that come on and our guest roster varies. Right.

And it’s interesting because when we first began, the hypothesis was, you know, sports grid is going to be competitive in pregame analysis and postgame analysis because we don’t have live rights. We found that that’s actually the opposite. People consume sports grid the most when live sports are happening.

And I think that that actually represents an interesting shift in broadcasting rights in the sense that right. Your mobile devices, your cell phone. Many people are now consuming sports and sports content on their cell phone and their second screen is effectively the television.

Ryan Knuppel
Right.

[Speaker 1]
And that’s kind of on in the background. And I think that that’s a really interesting shift in consumer behavior. And it’s really something we’ve actually been able to prove at sports grid.

Ryan Knuppel
So what about social media influencers? Are you guys doing a lot on social as well? Are you really sticking to the, you know, the kind of the TV channels type set up?

Talk about the social side or influencer side to kind of help us portrait grow.

Jeremy Stein
So we do leverage social social media for sports. Right. We’re creating 18 hours every day.

We don’t need to create more content for social. So a lot of our existing network flows through our social channels where we are really investing heavily in social and influencers is around casino. Casino is a very high growth area for sports grid.

So we have big deals with people like Paige Beranek, Brian Christopher, people who are both known in that world and not known in that world, who we think have an audience that looks like the actual customer base. We are now leveraging those audiences to help our customers, you know, convert into casino influencers. So I think it’s a really interesting area.

I think that, you know, casino content, right. It’s less on the big screen, less on the television. It lives more on things like kick.com.

It lives on YouTube. And I even think you’ll start to see it infiltrate things like Instagram a little bit. So that’s really where we’re focusing our social resources.

And this kind of doubles back a little bit to what we talked about earlier in editorial versus connected television. Social media, I think, has largely been solved, right? It’s very difficult to create an account today that goes from zero to a couple million followers.

But again, right, casino is kind of that white space on those platforms. So I think we’ll find a lot of success there. And we’ve seen a lot of early success.

Ryan Knuppel
Why do you think that is? I hear this a lot, actually, is, you know, kind of we started in sports. Now we’re in casino.

We’re kind of transitioning from different, you know, niche within gambling. Why do you think that is? Why is casino kind of that natural next progression?

It seems to be kind of more popular right now than it was eight, ten years ago.

Jeremy Stein
Well, so it’s driven by two things. First, it’s driven by budgets, right? We see large budgets right now that are coming from the sweepstakes industry because they’re operating under a lottery law, which enables them to operate in states where you can’t operate from a regulated perspective.

So there is that demand from a budget perspective. I think that in sports betting, right, it’s kind of a known quantity. You know, we have over 30 states that are legal.

We have a very strong forecast of what’s going to happen in the future. And that also goes back to budgeting purposes, right? People understand their customer acquisition costs.

It’s not 2018 where it’s grow in every single way imaginable. It is a little bit different. So I think you are seeing, you know, companies that are shifting towards that because a lot of them, they might not have any choice but to.

But also from a regulated perspective, casino is a huge profit center, right? For FanDuel, DraftKings, they make a lot of money. You name it.

It’s also a growth area. There’s only six states right now that have regulated casino. While it is a slower onboarding, you know, method than lighting up in new states like sports betting, it will happen, right?

So you have a lot more states that are going to be ready to go in the future. And I think that those businesses want to get out in front of it.

Ryan Knuppel
Thank you for that answer. Appreciate that. So what’s the future look like for SportsGrid?

What’s the next year or two look like? What are you guys working on? What can you talk about is the future?

Jeremy Stein
So we are working on our second vertical, and that is casino. It’s going to be nested on SportsGrid. We’re already airing these shows.

But at some point in the future, we would like to move it outside of SportsGrid and have it become its own brand. I can’t say for certain that it’s going to only live on fast. We are going to be a lot more social heavy with that type of an audience in the YouTubes of the world, the kicks of the world.

But that’s something that’s very exciting for us because we’ve been looking at new verticals for a long time. We wanted to find the vertical that helps us serve our viewers. It helps us serve our customers.

We looked at finance. We looked at crypto. And casino, of course, is just the natural progression for us.

Ryan Knuppel
Absolutely. Well, Jeremy, you’ve been in this business a long time. You seem like a very well-rounded, polished entrepreneur.

I’ll call you an entrepreneur, business owner, whatever we want to call people like you. I would be remiss if I didn’t ask, what’s one piece of advice you’d have for upcoming entrepreneurs? Somebody starting something in this crazy sports business world we all live in.

Somebody starting something, has an idea, wants to start something. What’s one piece of advice from your 8 to 10 years of entrepreneurial experience?

[Speaker 1]
I’m going to pass on advice that I got myself, that it’s always easier to keep going than it is to stop. Entrepreneurship, it’s hard. So I went to Babson, and we like to say at Babson that entrepreneurship is a fancy way of saying that you’re unemployed.

And that’s largely true in the early years. And it’s hard, right? Starting a business, it’s not easy, right?

You have to go in with all of this optimism. You have to be aware of the downside, but you have to be a blind optimist, right? That’s kind of the reality.

You’re going to hit a lot of bumps along the way, and sometimes you’re going to want to stop. But it is always easier to keep going. And now I really know what that means by that.

Like, if you wanted to shut down a company, it’s a legal entity. So beyond just, like, stopping the actual operations, like, it’s going to be a year of your life of winding up, you know, predators, chasing investors for signatures. There’s a lot that actually has to happen.

So oftentimes, right, it is easier to keep going, to fight through the pain. And if you just survive long enough, eventually you will find your way. And I think that that’s what happens with a lot of successful businesses.

There’s no such thing as an overnight success. Anybody that is an overnight success has been toiling away for five years, but quietly doing so.

Ryan Knuppel
Yeah, you just heard of them at the last minute. Great advice, Jeremy. I appreciate that.

Okay, well, I mean, this has been an amazing show, amazing interview. I’m so glad. I can’t believe it’s taken 244 episodes to get you on here.

I should have had you on here 200 episodes ago. But that said, what did we miss? What do you want to close up with?

Anything we missed? Anything you want to say or talk about to the audience?

Jeremy Stein
No, I think that this is a pretty good overview of where SportsGrid’s at. And, you know, honestly, Casino’s the future for a lot of the reasons that I outlined earlier.

Ryan Knuppel
That’s interesting. It’s going to be fun to watch you guys pivot into that. Not pivot, but move into that space alongside of sports.

I’m excited to watch that and kind of see that journey as you go through it. So, well, I wish you all the luck, Jeremy. Thank you for coming on.

Appreciate it. And looking forward to having you back on in a year or two and talking all about the casino side. Thank you so much for having me.

All right, take care. We’ll talk to you soon, Jeremy. Good luck.

Jeremy Stein
Bye. Thanks.

Ryan Knuppel
Bye-bye. Jeremy Stein of SportsGrid, guys. That’s 244.

What a great person. What a great company. I’ve really been amazed watching the growth.

I mean, I was in touch with SportsGrid back when they kind of had the concept and started and all the above. I was kind of watching what they were doing. And just to see the journey and now to see what it is, you know, you look at what they have going on.

You’re like, crap, how are they everywhere, right? How are they everywhere? And, you know, I think that kind of alludes to what Jeremy is talking to.

Just keep going. You know, you’re not going to get to where you are unless you keep going through the journey. So keep going through that.

And they’re a testament to that with what they have going on at SportsGrid. So I forgot to ask Jeremy how to get a hold of him, but I’m assuming he’s on LinkedIn and I’ll ask him after. We’ll make sure to put that right front and center on the show notes.

So I’m sure you can go out to SportsGrid, contact them there. Check out LinkedIn. I’m sure you can get them on there as well.

If you enjoyed this show, please make sure to like and follow what we have going on. If you want to see other guests that are in this space, please just reach out to me. I’m Ryan Knuppel.

You can find me KNUP on most socials or out on LinkedIn. I love LinkedIn. It’s a place to connect with all of you friends in this business.

So, all right. That’s it for Episode 244. Take care.

Stay safe. And we’ll talk to you next time. Bye-bye.

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