RYAN KNUPPEL
Hey, what’s up, everybody? Ryan Knuppel here, the Knup Sports Show Episode 193. I’m excited to have everybody here listening and tuning in post Super Bowl activity. Hopefully you enjoyed the game, I talked about it on a couple previous episodes, but, man, what a fun game. Leading up to the end was kind of anti-climactic at the end, but whatever, it is what it is, hopefully you enjoyed that and all is going well after that. Now we’re leading in to kind of a dead sports time, I mean March Madness coming up, which will be amazing, but man, when football ends, it’s like, everybody takes this deep breath and it gets a little crazy. But, anyway, today we’re not here to talk about actual sports, we’re here to talk to another amazing guest that I have for the show. Um, he’s gonna be a speaker on a panel at iGamingNEXT coming up, we’ll talk a little bit about that, we’re gonna talk about his life, his career, and really get to know him. I think you’re gonna enjoy this episode, so let’s dive right in and bring on our guest today. We got Kai Bond. Kai, how are you, my friend?
KAI BOND
Doing well, thanks for having me.
RYAN KNUPPEL
Oh, amazing. I’m so blessed to have you here today. Hopefully you’re doing well. You’re up in New York City, or New York area, correct?
KAI BOND
That’s right. In Brooklyn today.
RYAN KNUPPEL
Awesome. Amazing. Well I’m excited to get to know you a little bit, chat with you on here, and I’m sure our listeners are as well, so let’s dive right in, Kai. I want to know about you a little bit, so tell me about a little bit about yourself, especially from a career side, you know, what your career path has looked like and what kind of got you where you are today.
KAI BOND
Sure. Um, so my background primarily in tech, um, for the last, you know, close to 20 years. Started off my career at Microsoft back in 2001 and got the bug to join startups, so made the dive over in 2004, and after a few years working for other folks, I decided to take a deeper plunge into the startup world and start my own company. Uh, so in 2006 I started a company called SwitchGames, a peer-to-peer marketplace for gamers. Uh, unfortunately, not the success we wanted, so whined that down, but was crazy enough to do another venture after that in the real money gaming space in 2010 called CashPlay Games. Uh, so chance-based games tied to a sweepstakes engine, you know, providing users the opportunity mobile-first to win real money playing casino games on their phones, and then started a 3rd company in 2012, um, called Pixie TV, and that was in the sports base. Um, and that was actually providing custom content and contextually-relevent content on broadcast television, so our big hero products were through your fantasy football scores, league scores, team scores, standings, injury reports, as a ticker on the bottom of your TV. Um, and then we moved into the sports lines, wagering odds, and that was, you know, really sticky, that company ended up getting acquired by Samsung, and when I was there I helped scale that product to 60 million smart TVs globally, helped with their global accelerator program and their investments team out of the New York office, and organization called Samsung Next, and I had the opportunity to go over to Comcast Ventures, so I joined there, did two things at Comcast, one was leaving a fund called Capitalist Fund, which was a $20 million fund focused on underrepresented founders, and the other half was investing out of the flagship fund in gaming. And so, looked at deals from $250,000 to $250 million, you know, large and small checks every stage, and during that time, I invested in four companies that Courtside also participated in. In 2016, they were one of the only funds in the planet that was looking at gaming, that was looking at sports, both highly relevent and interesting to Comcast Ventures team, and so in 2019 I jumped ship to join Courtside, kind of the blend of going back to the startup world, little bit more entrepreneurial out of the corporate world, and we raised fund 2, in 2019, that was a $55 million fund, and then we raised fund 3 which has recently been announced, which is a $100 million fund dedicated to the world of sports and gaming, so that brings us to today.
RYAN KNUPPEL
Wow, what a career, what a path. You’ve kind of been lots of different channels, but that’s amazing. Congrats on all the success and I’m sure you have tons of stories for each one of those, but that’s a lot of different areas of the world you’ve been in, so very cool.
KAI BOND
Thank you. Yeah, it’s been, you know, I think the ability and the opportunity to work at large corporates, having a global focus, and then at small startups, you know, deep in the weeds, it’s provided a lot of insight on how you look for founders and what we think of as market-moving opportunities that can generate outsized returns for our investors as well, so it’s been fun, it’s been a wild ride, more to come, it’s just the beginning of this path at Courtside, so we’re really excited to have some capital to play in this space that quite honestly not a lot of people wanted to invest in in 2016. Um, we started, my partner started Courtside fund 1, you know, Vasu had sold and exited a company in the sports tech space, which he was never able to raise a dollar of venture capital from institutional investors. It was all high-networth individuals, pro team loaners, people were in and around the world of sports. So after that company was sold, he went back to those individuals and he said, “Look, there’s real business here, there’s real money and people don’t understand this industry, and we think we can capitalize on it”, and that was how Courtside really came to the market, was filling a gap that no other funds were really paying attention to.
RYAN KNUPPEL
Yeah, that’s awesome, and that’s what I want to dive in to Courtside now and talk about, you know, one, how it’s been going, and then secondly, kind of dive into your portfolio a little bit and look at some of the investments you’ve made, that always interests me and I’m sure other people, just the types of companies and startup founders that you’re working with. But first of all, I mean, I know you just talked about Courtside, but tell us how it’s been going, tell us a little bit, I’m gonna scroll through the site here as you’re talking, tell us just a bit of a high-level about Courtside as a whole.
KAI BOND
Yeah, so, you know, thematic focused fund, um, you know, sports in gaming are at the very core of everything that we do, but sports in gaming are much broader areas than people, I think, want to give credit to. When they think of the world of sports, they think of teams, but youth sports is a massive part of the ecosystem, right? There’s a huge amount of participatory engagement that goes on at the youth level. Um, at the professional level, the use of data analytics, you know, to power decision making behind athlete performance, around game plans, and then you look at the culture of sport, right? It’s much broader, you know, when we did the investment in StockX, people were like “This idea is crazy. Why is somebody gonna want to wear a used pair of sneakers”, right? “The markets not big enough”, and it seemed insane, right? But there was something special around sports culture and understanding why that limited edition sneaker meant so much, um, to the individuals who followed either that athlete or a particular team in a drop, so we’d look at culture, we’d look at technology, we’d look at society, we’d look at the evolution of what sports means in a broader picture, and when it pertains to gaming, I think you’re seeing this intersection of sports and gaming, when we grew up in an era, I won’t speak for how old you are, but the Tecmo Bowl era, I just watched the Bo Jackson 30 for 30 on the plane home from London last week, and you know, they talk about how Bo Jackson was unstoppable in that game, and these kind of larger-than-life stories, bringing entertainment and media value, right? So if you look at an investment in something we did in something like the Athletic, right, again, people were like, “Why is somebody gonna pay $50 a year for sports content? You can get it on NBC, ESPN, ABC, Yahoo Sports”, but they’re never gonna write a story about “Board Man Gets Paid” which is one of the best legends around Kawhi Leonard of all time, and that’s the story that fans want to connect to. The meaningful connection to an athlete and a player that they love, and obviously, tremendous success there, New York Times acquired that business, and it was a great business because it was a subscription business, low charge, high retention, business, and so we look for areas and pockets of the ecosystem that other people coming from traditional venture might not see as value to the customers that are out there, and sports is a massive audience globally. And so, we have a big global focus, we’ve invested in India, in Nigeria, Brazil, Mexico, western Europe, United States, and there’s something that unifies people, right? You saw it with the World Cup, you see it with large sporting events, the Olympics is another example, bringing the world together, and so we look for these themes and what we can do to bring great media entertainment and game play to the masses.
RYAN KNUPPEL
Yeah, I love that, I love the intersection of sports and lifestyle, and all of that area. I think it is kind of one of those spaces that, yeah, when you think of sports, you just think of the teams. Yeah, you said that perfectly earlier, and after kind of scrolling through a bunch of the companies, we wont go into detail, you mention 2, 3, 4 of them already, but several of them on here, you know, amazing companies in gaming and sports and lifestyle, all over the place, so lot’s of cool opportunities, you know, that you guys have had, and I’m sure lot’s of success from these businesses, but Kai, I want to shift gears here real quick, we’ll get back to Courtside here in a second, but I do want to shift gears because you’re actually gonna be on a panel that I’m going to, I’m going to iGamingNEXT here early March, actually, this is like 3 weeks away, crazy how time flies, but in 3 weeks, iGamingNEXT will be hitting New York City 2023, um, you’re on a panel here, I believe, called ‘Specifics: Who Will Succeed in 2023?’. Kind of a broad topic there, I’m curious, you know, don’t give away all your secret sauce from the panel, but can you give us a little nugget or two from what’s gonna be, what you guys are gonna cover in that panel?
KAI BOND
Yeah, you know, there’s been obviously, anyone who’s following this show, knows the massive growth and proliferation of real money gaming in the United States, um, and the growth from daily fantasy into real money gaming, um, and wagering, so we’re excited to talk about what the opportunities are in that space. When we think about the world of real money gaming, there are huge opportunities for growth, both in the sports ecosystem and also beyond that. You look at video gaming, you look at lottery, you look at sweepstakes, um, you know, tremendous opportunity, so I’ll be focusing a lot of my time and energy on “Where are the other opportunities that are gonna go from 0 to 60 billion in top live spend over the next 5 years to continue the growth as an industry?”, so we’ll talk about user engagement, we’ll talk around fundraising, we’ll talk about monetization, and it should be a fun panel, some great people joining me along the way, folks we’ve coinvested with, folks I hope to coinvest with moving forward, so it’ll be a lot of fun, there’s a ton of great speakers. If you look at the lineup, it’s amazing to see, again, big companies who are represented in this, multi-billion dollar publicly traded business, all the way down to early startups, people who have had multiple successes, and started companies five years back in the DFS space and now coming back at it, so it’ll be a great gathering, hopefully everybody who’s watching this show can figure out a way to attend or some of the events around that.
RYAN KNUPPEL
That’s gonna be amazing, and congrats on being a featured speaker. I’m excited for this one, I know many of them on the panel, including yourself now, I’m excited to listen to what you guys have to say and certainly 10:05 am on Wednesday, so one of the first panels, right out the door, right out the shoot, people are gonna be ready to go Wednesday morning for that one, so iGamingNEXT, March 7-9th, if you don’t have your ticket already, grab it, ‘KNUP10’ promo code, you can get a little 10% off, make sure you grab that, so hope to see you all there, and Kai, for sure I’ll make sure to say hello to you there. Man, good luck on that panel, it’s gonna be awesome.
KAI BOND
Thank you. Appreciate it.
RYAN KNUPPEL
Awesome. Cool. So let’s dive back in to Courtside real quick. What’s the future look like for you guys. Is it just as simple as investing in more companies, I mean, what’s the future look like for you and your company?
KAI BOND
Yeah, I think that as an investor and as a fund manager, there’s three areas that we focus on. One is finding the best founders in the world to invest in. Inevitably, at the stage that we invest in, at the pre seed series A, you’re making a bet on an individual, so we do everything we can to work with exceptional founders. We’ve missed on deals, we’ve passed on deals that have ended up being successful, but we try to maintain our position as incredibly helpful throughout the entire ecosystem, connecting people, hiring, helping, and I think that kind of good karma will come back to pay itself forward. The second time is “What does building a brand, what does building an enduring venture fund look like?”. We’re on fund 3, we hope we get to fund 6, 7, 8, along the line, so staffing, hiring, managing our investors. Obviously, we have a great roster of folks, corporates in the world of sports, professional team owners, some of the largest DFS and publicly traded gambling companies, and so we try to add a lot of value and so when we think about providing value that’s inside information, knowledge, connections, so building Courtside to last through what will inevitably be multiple cycles, some of them great, some of them difficult and challenging, and then the 3rd is continuing to evolve our thesis, right? Culture changes, society changes, technology advances, and trying to figure out how you color in the center of that venn diagram where you can hopefully identify what the future of the next 3, 5, 7 years looks like. And I always say it’s impossible to see around corners, but often times, you can see the shadows before you see what’s there, um, and that’s really what we’re looking for, what are those signals and how can we stay out in front.
RYAN KNUPPEL
I love that, and I love what you said, I want to key in on one thing real quick here before I let you go, I know you mentioned exceptional founders, and you didn’t say the best business model, the best business whatever, you mentioned the founder of what you’re looking at, and so can you give me, I’m sure there are people watching, we know there are so many startup founders and people wanting to get into this space, gaming, sports, whatever it may be, give us a little bit of what an exceptional founder looks like from a quality side, again, I know there’s not one size fits all when we’re talking about that, but there’s gotta be some criteria, some type of thing you look for in an exceptional founder. What does that look like to you guys?
KAI BOND
Yeah, you know, it’s different for every investor, I think, we look for somebody that has vision and understands some unique insights or data, um, that no one else has, right? And sometimes those are individuals that come from big companies, sometimes they come from startups, sometimes they’re repeat founders, but the vision and being able to see 2-3 years down the line of what and as a technology evolves and develops, what it will be. The second compenent is an exceptional execution. Someone who, when we’ve passed on deals before at a pre seed and we get their monthly updates, and we talk to them quarterly, and then 9, 12, 14 months later, I’m like, “Everything this individual, CEO has said, they have executed on and done. Why should I now continue to doubt them? In the beginning we had some question marks, maybe it didn’t fit our thesis perfectly”, and we challenge ourselves, right? What are we missing? What are we doing wrong? You know, we don’t know everything. Um, but feeding that data back into our own thesis and prosecuting that, and so execution is a big component, and then the 3rd that we look for is coachability, right? Like, I was an athlete growing up and played a ton of sports, and I think, when you look at the best athletes in the world and you look at the best entrepreneurs in the world, the parallel is a tenacity and a dedication to continuing to improve. And the best CEOs, multibillion dollar companies, the best athletes in the world, they train, they want to get better, they take advice, they take feedback, they get coached and every year they work on something. So it might be three pointer, it might be my low post game, it might be my free throw shooting, but every offseason, you’re going back to the well and saying “How can I improve?”, and the greatest founders do that to, right, “How can I be better at marketing? How am I looking at creating better UI/UX?”. So, those three components often times give us an indication at the early stages of what they can potentially accomplish, and again, there’s very little data at the stage that we’re investing to be able to base investments on empirical data, and so we’re looking at signaling around how well you can execute on those three areas, and if you can do those things, often times, you can succeed in this space.
RYAN KNUPPEL
Yeah, amazing. Thanks for sharing that insight. I think that’ll help a lot of people I think, and a lot of people are trying to be great founders, they’re trying to do the best they can, so any sort of tips and advice there is amazing. So, you used some basketball analogies and you mentioned you played sports, am I gonna guess you played some basketball in your day, or what sports were your key sports that you liked to play.
KAI BOND
Soccer. So when you mentioned the Super Bowl being over I was like, I love the Super Bowl, I love NFL football, but there were some amazing Champions League games this week, there was the Arsenal vs Man City game yesterday, so, you know…
RYAN KNUPPEL
[Laughs]. You wanted to punch me right across the face when I said that. You were like “Wait, what? It’s just starting”.
KAI BOND
[Laughs]. Not at all. Not at all. You know, I love, I can genuinly say I love watching and playing every sports. There are some I don’t know well inside and out, cricket being one of them, we’ve now invested in four deals in India, so I’m trying to bring my cricket knowledge up to par so I can have some conversations around that, so again, an area of growth for me to expand and to understand better, but yeah, soccer is my primary love.
RYAN KNUPPEL
Cool. Awesome, Kai. Well I really appreciate your time here today, really do. Good luck on the panel, I think that’s gonna be awesome. I’m excited to listen to you and meet you in person. Any last words, anything we missed, anything you wanna touch on before I let you go here?
KAI BOND
Nothing from my end, just looking forward to seeing you in person. Thank you for having me on, and if anybody out there is interested in chatting, you can find my information on the Courtside website, so I look forward to engaging with everyone out in the audience.
RYAN KNUPPEL
Awesome, Kai. We’ll make sure to put those links to Courtside and to you out there in our show notes, that way everyone can find them and get a hold of you and you’ll get flooded with correspondance, so that will be amazing. Alright my friend, well enjoy the rest of your week. We’ll see you in about 18 days, I think it is, and talk to you soon. Thanks Kai.
KAI BOND
Alright. Take care.
RYAN KNUPPEL
Alright, that was Kai Bond of Courtside Ventures, I almost said ‘adventures’. Really excited to have him on. That was an amazing show. Hopefully you got some value out of that. He really dove deep into a few key areas, you know, what they look for in founders, where they’re headed, some of the companies that they touched on as well, so you can go back, watch that again, we’ll have the show notes out in the show as well. Hope to see you at iGamingNEXT. Again, I’ll put up the dates here. March 7-9th, promo code ‘KNUP10’, make sure you get your ticket if you can. I think they’re almost sold out, so if you’re gonna get a ticket, please make sure you go grab that so you don’t, you’re not on the sidelines looking in, and if you are going, make sure to send me a message. I’d love to chat with you, touch base with you, have lunch, whatever it may look like. Alright, that’s all I got for today. That is a wrap on 193rd episode, hopefully we’ll have 7 more this year to get up to 200, that’ll be kind of fun. But anyway, we’ll talk to you all soon, thanks for your attention, stay safe out there, and we’ll talk to you all the next one. Bye-bye.
Relevant Links:
Learn more about Courtside Ventures here.
Reach out to Kai Bond through email or on LinkedIn.
Get your iGamingNEXT NYC 2023 tickets here. Use promo code ‘KNUP10’ for 1-% off at checkout.
More Knup Sports Links
- I refer to Knup Sports often in my show. That’s our sports passion site. Check out KnupSports.com here.
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Contact Ryan Knuppel
- LinkedIn: https://www.linkedin.com/in/ryanknuppel
- Email: ryan@knupsolutions.com
