How ChessUp Appeared on Shark Tank, Became Multi-Million Dollar Business

Electronic chess boards have been available for home use for as long as Radio Shack has been in existence. In fact, they've kept up with modern technology even better than the stores that used to sell them.

The industry leader in terms of sales and features is ChessUp, which has now released the second iteration of its board, ChessUp 2. Their newest feature is built-in Wi-Fi for wireless and seamless synchronicity with your Chess.com account. This combination of the ease of online player pool with tactile gameplay has led to more than 50,000 units being sold.

Chess.com caught up with co-founder Jeff Wigh to hear why he started the company, his appearance on Shark Tank (with co-founder Adam Roush) and the aftermath, and other subjects like cheating and possibly becoming a competitor to DGT. This author also tried to play a 2300-rated bot while conducting the interview and you can see how (badly) that went.

(Note the interview was edited for clarity and also Chess.com has a partnership with ChessUp. You can use the code CHESS to save 10% off at playchessup.com.)

Chess.com: I'm happy to be joined by Jeff Wigh, the co-founder of ChessUp, the coolest digital chessboard that exists. Jeff, thanks for joining us.

JW: Yeah, thanks, happy to be here.

Chess.com: Well, I wanna start with the brief history of ChessUp. You know, your company's founding reminds me a lot of Chess.com's founding because, you know, Erik [Allebest] is an entrepreneur. You're obviously an entrepreneur. You both got a degree in business and, and you're both amateurs. You're not professional players, which I think maybe helped at all, but, you have one thing that he didn't have your daughter helped shape this company. Can you explain exactly? Your daughter helped conceive the idea.

JW: Yeah, absolutely. So my daughter was playing a friend on another app called Game Pigeon. It's a texting app, and they have chess as an option, you know, it's a lot of things like play pool, play these turn taking games, and when she pulled up chess, I was watching her. She's playing her friend, and it's your classic situation where you know someone who's very new to chess moves the pawn and the h-pawn out and brings the rooks out and then they start battling with the rooks so I'm watching this go on and I'm thinking: "Well, you know, I, I have a chessboard in the closet! Let me teach you chess. At least I could maybe teach you how the knight moves or something."

And I get the board out and we set it up and I'm gonna teach her chess and that's immediately when it became obvious that like chess is a hard thing to teach, especially to somebody who's brand new. And so I'm going over all the rules. I'm talking about how the pieces move, what is check and checkmate, and I'm losing interest, you know, and it's like I was hoping this would be a fun moment and it's like chess is just overwhelming, so the inspiration for ChessUp came from this experience where it's like they just want to play.

Is there a way to teach somebody while they play why we touch the pieces so they learn how the pieces move naturally? They learn the different situations of check and checkmate by exploring the game. And so the inspiration for ChessUp is exactly that make the game approachable, make it very intuitive, and make it fun to learn for a beginner.

Chess.com: Great. And you said teaching while you play. I'm going to attempt to do something that I've never done in my 12 years at Chess.com. I'm gonna attempt to play while I interview on the chess board. I think it's gonna be a fun challenge. So I'm just going to play a bot because I doubt I'm going to play my best. Now I'm gonna play at my Elo, which is 2300, although suffice it to say I expect to play a little bit worse, having a fun conversation... All right, so I click new game and play and yeah, so we're gonna get off and running here now. I've kept the eval on. That's the one little hint I'm giving myself. We'll get back to the interview, but I'll occasionally make some moves over here.

You're also quite famous because you were able to do something that Erik and Danny were not able to do. They really tried to get on Shark Tank, but you did it! So first of all, I want to ask you: Funny and creative pitches are key, but it was your co-founder Adam who had to do the scuba shark symbol. Did he lose a bet with you or something?

JW:  No, no, it's just he did a much better, quicker, you know, get the fin centered than I did! So when we went through the auditions, he ended up pulling that move better. So I turned into the pointer; he turned into the shark.

Chess.com: All right, well, tell our audience that has creative ideas out there, how did you actually get on the show?

JW: Yeah, so Shark Tank, you can apply online and we had done that and never gotten anywhere so we actually reached out to the producers of the show directly, on LinkedIn. And they replied and they heard our story and it's pretty funny. The only reason we even did that is my co-founder Adam's LinkedIn premium was expiring. It's like, I've never used this, what do I do with it? It's like we just reached out to all the producers and they took it very seriously, replied, and within a few weeks we're making audition tapes and actually got through. It was really cool.

The Shark Tank pitch from Erik Allebest and Danny Rensch from 2017.

Chess.com: That is the best use of LinkedIn premium I've ever heard! This is a big question: I've watched a lot of Shark Tank. You came in asking for $300,000 for five percent. That imputes, by the way, a word I also learned from that show, that imputes a $6 million valuation. You had to come in thinking that was the beginning of a negotiation. So, did you get what you wanted at the end of the show?

JW: So yeah, absolutely, and that's kind of like a starting offer. We knew that, and by the end, when you're up there you film Shark Tank for like 45 minutes, and they cut it down to five. So there's a lot that gets cut out, but we were prepared to move off that number and get somebody like Lori [Greiner] involved and that's exactly what happened. Everybody was hemming and hawing about the valuation and then it's like, hey, we got another deal ready for you. And that's when we slipped in what we really wanted and then things went really fast in the end and we closed that out, so it was fun.

Chess.com: Yeah, we've seen some situations where if you don't act fast, you lose your offer. But you know, Lori made you an offer and Robert was about to interject and then the accept happened very quickly. The audience never got to hear what Robert was going to offer! Did you ever find out what he was going to offer?

JW: We have never found out to this day. It's something I'm still curious about. We never reached out to him afterwards. We've never heard from him. There was no continuation of the conversation, so it'll be a forever mystery what Robert was willing to do, and we'll never know.

Chess.com: OK, just one more Shark Tank question just because it's such a cool idea. Now going in, I would have thought that Robert [Herjavec] or Mark [Cuban] were the most tech-forward partners. You ended up with Lori, which begs the question: When are we going to see ChessUp on QVC?

JW: So with Shark Tank actually you film and then it airs, and with us that filming and airing happened really quick, just a couple months apart. By the time we'd actually aired, and Lori's team was great, we were going through all the due diligence with them and preparing to make Lori a partner in in ChessUp. By the time it all aired and happened, the deal no longer made sense, so I'm sorry to disappoint everybody, but actually we never did close the final deal. We made the verbal offers on the show, but it actually never ended up being a thing. ChessUp just grew on its own and turned out that that's actually maybe the best thing that could happen to us.

Chess.com: All right, well, Lori's loss is Chess.com's gain. We're happy with our partnership with you. You went through the Garmin innovation lab where I kind of picture people sitting in beanbag chairs just thinking of cool stuff. I'm sure it was more formal than that, but, you finally settled on ChessUp as your baby. Can you tell us some of your darlings that you killed? What were some ideas that you were tossing around that ultimately lost out?

JW: Yeah, so a lot of product ideas, went through the kind of the wringer and not a lot make it out the other side. ChessUp was a was a great idea from the start. We had worked on other smart gaming devices, a Rubik's Cube that can teach you how to solve the Rubik's Cube, and connects online. We had tried some other things to do with filming sports. We tried stuff to do with even smart disc golf stuff. We ended up not doing any of those. However, I've had friends take some of these ideas and actually turn them into businesses, so maybe they were better than I thought.

Chess.com: That's fascinating because Chess.com has also done things with Rubik's and with disc golf, so this is all one happy ecosystem. Now Chess.com, as you know, as our audience knows, went bonkers during "[The] Queen's Gambit", and I'm wondering about the timing of your show and your Kickstarter campaign, which also did bonkers. How much did "The Queen's Gambit" series help ChessUp get off the ground?

JW: I think these things were tremendous influences, especially in when you get into chess beginners, because tournament chess was what it was. But when you get into "The Queen's Gambit", you're attracting a bunch of people who are never exposed to chess as kids. With that plus COVID where people are looking for hobbies, it's just like this boom, I think " The Queen's Gambit" probably doubled how much attention we were going to get with ChessUp. We had timing perfect because we launched our ChessUp Kickstarter in the spring of 2021, which is just right after "The Queen's Gambit" had been popular. So, yeah, lucky timing, I'll take it!

Chess.com: Absolutely. Now we also experience other big growth bumps during things like the [Lionel] Messi - Cristiano Ronaldo, Louis Vuitton ad, and of course the famous chess cheating scandal in 2022. I kind of think you haven't made it in the chess world unless you've been involved in a chess cheating scandal. Has ChessUp ever been involved in one?

JW: So we had an incident, not nearly as famous as the major chess cheating scandal, but, our board connects online plays online, and of course Chess.com enforces fair play policies. And we had a customer she bought it for her kid. And the kid got kicked off the platform for cheating. And Mom, you know, the kid claims innocence: "Mom, it was the ChessUp that caused this. They got my account banned!" And she blamed us. So she came to us and was saying, "Hey, little Timmy's innocent. He'd just been practicing this opening." We reviewed the game. Little Timmy played better than Magnus Carlsen for, you know, several matches in a row, and so we had to break the bad news very, very softly like: "No, you might want to ask them again about what really happened." It's very uncomfortable to approach a customer that way. But yeah, that was our cheating scandal...little Timmy tried to cheat a little bit and got busted and blamed us, and mom blamed us too.

Chess.com: As the main guy at ChessKid for more than a decade, I've had a few little Timmy conversations and...we'll just leave it there, but, of course, there's much more force for good than a chance for cheating with your board. The board interfaces with Chess.com, by the way, quick update on my game. Tell us exactly how the interface with Chess.com works.

JW: With the board connected to your Wi-Fi, everything's right there on the board. You just turn it on. You have your Chess.com account. You can hit "seek game." You can play any of the time formats you like. You can actually play all the Chess.com bots and all the dialogue is right there. Your games are saved on Chess.com afterwards, so it's like Chess.com on a real board. It's a great blend of online and tactile together.

Chess.com: And I'm playing a bot, but suffice to say this game will be saved on my ChessUp board as well, right?

JW: Yes, yeah, you can access that game and analyze later.

Chess.com: What are some other things, Jeff, that you're working on with the Chess.com integration? Like, I don't know, puzzles, Freestyle chess, lessons? I'm just throwing out any ideas. I know it's hard to program everything, but tell us about something coming soon.

JW: Yeah, always looking for new features. We do plan on rolling out some puzzle version. We have lessons worked into the board where they're tactile and interactive with the board inspired largely by a lot of the Chess.com lessons. We actually are working on Chess960 -- or whatever you want to call it, Freestyle chess -- is coming out soon, probably 2026. I don't want to get our users too far ahead of the schedule there, but yeah, we're working on all of those. Also just really looking forward to a feature where two player over-the-board games get more mixed into the Chess.com ecosystem -- that would be very cool where it's like could we play rated over the board. Those are the kind of ideas we're working on right now.

Chess.com: Sounds great. You mentioned lessons and I know for a while you had both (GM) Levon Aronian and (IM-elect) Tatev Abrahamyan doing some work for you, and they've both had banner years. So can we credit ChessUp for their late-career revivals?

JW: Yeah, I mean, it must have something to do with it. I think there's correlation and causation, right? So yeah, congratulations to both of them on having outstanding 2025s. And you know, (they are) still friends of ChessUp -- Tatev does our lesson content on the platform and is still very involved. So happy for them and I would love to say that yeah, maybe we inspired some success there.

Chess.com: Well, what about you? Have you gotten better as a chess player, just being in the chess world for the last five years?

JW: So both my co-founders and myself were all kind of beginners at chess during this whole project. I had been exposed to chess as a programmer, not necessarily a player, and knew how to code AIs. But the time that we've done ChessUp, one of my co-founders has gained 1000 Elo points and has gone from, you know, true beginner all the way up to pretty competitive intermediate player on the platform. His journey over the three to four years is actually pretty incredible. I think it might even be 1100 points gained by this point, this stage.

Chess.com: In some ways, I would almost attribute the success of Chess.com to Erik not being a master player. He really thought about the everyman. Do you think that you being more of an everyman rather than a master or a grandmaster helped you in crafting a product that appeals to the masses?

JW: One hundred percent. You know, chess gets a lot of attention at the top levels -- at the Magnus Carlsen level -- and everything, but 99.99 percent of us are not tournament players. They're not GMs, they're not titled players. And so we understand that mindset. We also understand the true novice is somebody who is just wanting to learn how the pieces move, wanting to have a new hobby, wanting to do something in their family room with chess, and that actually is a benefit for us to be beginners. And...I think as a product we cater to everybody. You can still play rated games no matter how highly rated you are, but we absolutely make sure that everybody is comfortable sitting down, touching a piece, seeing how it moves, and that's what ChessUp does best.

Chess.com:  Yeah, and the bots start at the rating of 500, go all the way up to 3000, as I mentioned, I'm playing 2300 level, which is bot level 20... Let's get back to the interview. So Chess.com interfaces perfectly with ChessUp. Do you have any high-level stats on the number of people who are playing live games on Chess.com through your board or the number of games played?

JW: We're over a million games played. There's over 50,000 ChessUp users, and at any time about 100 of them are online. We did the math the other day. We're like, "Has a ChessUp board ever randomly matched up with another ChessUp board through Chess.com?" And it turns out, yes, actually dozens of times without even knowing it! ChessUp boards are playing other ChessUp boards online...

Chess.com: That's great. Now we're on ChessUp version 2. ChessUp 2 we'll call it. What are the biggest differences that you've added since the initial ChessUp?

JW: So both the boards have all these learn-chess features -- touch a piece, light up. The main thing that ChessUp 2 adds is it really brings Chess.com to the board where we have the display. We have built-in Wi-Fi. Our previous version, you would have to get out a phone and use an app to connect online and you would connect through Bluetooth. But with the Wi-Fi and the built-in screen, it's like it's all right there. The product does everything you need, so you can turn it on, connect to Chess.com, and play your matches right away.

Chess.com: Yeah, and it should be noted, when I got my board in preparation for our chat today, after a quick 30-minute charge, I was up and playing and interfacing with Chess.com right away, no app download, which was great. Tell us though, what are some secret features that I don't know about yet that maybe the average user doesn't know about? Maybe power features that you think are particularly cool?

JW: There's one that most people don't discover, and it's called hint limit. We have this assisted play mode where you don't just get the colors like how the piece moves. You get red and green to indicate bad move, good move, and we've noticed that players will sometimes become overly reliant on that, and they'll just, we'll call it "green hunting".

Levon Aronian made up that term actually, and you touch all the pieces to see what is a good move. That's not the intention. The intention is that you actually touch a piece and think about why is it a good move or what am I missing here. So for instance, we have this hint limit that only allows you to touch a certain number of pieces before it stops giving hints. So the position comes up, you touch your intended move, you see the moves are all red, they're all blunders. You have to stop and think about, OK, what did I miss in this position? So it's like a puzzle within your game that is probably my favorite feature. It's probably underutilized if people would use hint limit, they would get puzzles during their own games, and it's a really educational moment. I actually encourage everybody to go check out the hint limit feature.

Chess.com: Cool. Maybe I'll stumble upon it someday, especially now that you've told me, and that actually reminds me I once interviewed Gata Kamsky. He had just won a US championship and his two- or three-year-old son, who could not play legal games yet that I know of, was watching him play online where they color-code a lot of moves on certain websites. And his very first conversation with his son, his son says to him, "Why did you play all those red moves!?" So yeah, green moves, red moves, these are all sort of one family, I guess.

Now, I see even Chess.com, our brand is on the box when you buy a ChessUp board. So what has the partnership done for ChessUp's success?

JW: Yeah, so we look at Chess.com in a really unique way. We mentioned "Queen's Gambit". There's other events, the cheating scandal, COVID, that have boomed chess in the last five years, and we look at Chess.com as not just a recipient of that growth. We think they are a driver of that growth, and that is simply because Chess.com understands the beginner. They make chess fun...so that's the kind of things we want to be associated with. So with that we get a lot of exposure from Chess.com and the partnership which is fantastic.

I also think it's just kind of an alignment of understanding that who we are serving, and we're serving everybody. We want chess to be fun. We want chess to be approachable. We want beginners. We want to build the audience. And so with the brands, I think they work together very well in that regard. I think the exposure and that branding people have trust in Chess.com to teach them chess. They have trust in ChessUp to teach them chess. I think together you get the tactile world, you get the physical board world, and all the online tools together just makes a great offering.

Chess.com: Totally agree -- we're not in the physical product space so it really is a great partnership for us. Let's talk about the learning and stuff. Who wins between you and your daughter now?

JW: So I have two daughters. The one of them that the product was inspired by never really got into chess! The second one is actually pretty good. She's the younger one, and she actually still plays on her ChessUp. I still win at this point, but if you give her a little bit of hints, she can beat me. The other thing that's really funny about this daughter is she's so attached to the brand, we switched our logo from ChessUp 1 to ChessUp 2, and she threw fits. She actually drew us up all new logos that we should be using. She 3D printed logos for us like: "Hey, you know, don't forget about this one!" And so she's been into it. The youngest one still plays. She's climbing. I'm sure some day is coming when she beats me as well.

Chess.com: Let's hope so. Just getting back to Shark Tank, did you ever play Lori in a game? I know the deal didn't go through.

JW: So actually after the show, no chess was played. It was mainly reviewing accounting and doing all sorts of non-fun stuff. But her team was incredible -- well versed in business, absolutely very serious players, and they took the whole process professionally. It was a great experience; no chess was played at all though.

Chess.com: Well, who's the most famous person that's ever used a ChessUp board?

JW: So we have a number of NFL and NBA players that have bought the board, and we only notice because you're watching the orders come through and you're like, "Could that be?" And you look it up and sure enough it's NBA All-Stars, NFL All-Pros. We've even had sometimes where they come through the customer support channel and we're helping these professional athletes. And so the sport is very popular with these pro-level athletes and ChessUp actually seems to be very popular with them as well.

Chess.com: Who would be like the coolest brand ambassador that you could think of? Of course, if money was no option.

JW: Oh well, can I even go even more crazy than that, which is...Bobby Fischer always playing against himself, because he was just too good, right? And so like he's studying against himself I think. My mind always goes to where would he be if he actually had chess engines and chess AIs and he was able to practice with those tools? So I mean that's impossible. Nobody's going to make that happen, but I think it'd be incredible if he were born today where there's tools that you know, assisted play, where there's engines to play against that are superhuman. I think that'd be an incredible scenario.

Chess.com: Yeah, that would be great. And I just have to say, I know you're trying to reach the everyman, but inside the pack that I was sent (shows pack of checkers pieces). I think you were triggering me! What's this? Why? Are you gonna become CheckersUp? This is not very funny, Jeff.

JW: No, hey, it's an 8x8 board! Why not? You know, it's the same format as checkers, so you'd have fun. You can put in, set up the checkers, hit go, and there's six different levels of checkers AI. You can even actually set up rules about whether captures are forced or not. So yeah, it's a checkers platform as well. Now that's just an add-on. It is fun though and we get a lot of people actually who enjoy that and it's even kind of maybe makes people more comfortable with the board if they know that they can play a checkers game in their family.

Chess.com: It is a very cost-effective value add, I'll give you that. And I know Vasyl Ivanchuk has been known to play checkers during an award ceremony. Maybe we'll even throw a video up of that, that famous Chucky video.

Chess.com: Well, what about like outside the world of chess? I mean, you mentioned Bobby Fischer, but there's a ton of other celebrities, athletes, whatever, so you can just, you know, drop any name you want. Who would be a cool ambassador outside the world of chess?

JW: So I would...go to the NFL. I guess and maybe that's too American-focused, but I would love if we could get some quarterbacks, you know, get maybe...Victor Wembanyama. I know he's a chess player. I saw a video of him playing in the park in the rain in New York or something like that. That would be an incredible person to get a ChessUp into the hands of.

Chess.com: Absolutely, I think he's a star and personable. And you know, my team's got some connections! We'll see. What about your company goals for the next few years? Where do you see ChessUp being in a couple of years?

JW: So we love this space with the home boards. We'll continue to kind of round out the line of chess products. Some people like a wood board, a big board, a small board, a portable board, so I could see the ChessUp 2 platform just taking on a number of different shapes. And then beyond that, the hardware could be tournament capable. So even though we start as a product for homes and for beginners and for everybody, I still think it's interesting that we could make some tournament boards and actually do broadcasting with our with our hardware.

Chess.com: Cool. Well, you mentioned tournaments and broadcasting, so of course, my mind goes to DGT. Could we ever see a day where maybe the World Championship match is contested on some iteration of the ChessUp board instead of DGT?

JW: Well, that'd be incredible. I do actually have a ton of respect for DGT as a brand, and you know they make great boards and all this stuff in different spaces. We're kind of in this home thing and they're in the smart one, but yeah, I think it's fair because the product hardware is very similar. We can recognize the moves of the game. We can recognize the pieces, we just need to work on making something that's beautiful and big and wood and fits in a tournament hall, and I think we'll be there. We'll offer it from our side, that's for sure.

Chess.com: All right. And finally, does ChessUp have any other products coming out that we should be aware of? Or will ChessUp 3 be out at some point? Or will you maybe invent another product that adds on to your board? Anything you wanna drop here while we've got you.

JW: So I think ChessUp 2 is a very complete platform, so we're gonna see just different kind of shapes of it, different skins of it, you know, people like their piece style, we'll kind of try to appeal to that market and get a little more premium wood version. We'll probably get different sizes in there. The one thing I think we might add in the future is maybe a speaker so that we could do lessons more completely on the platform. That's about the only hole in the product. Other than that, it's a fantastic platform, so we just see rolling out ChessUp 2 into different forms.

Chess.com: Cool. Well, looks great. It feels great. I'm actually out of questions and out of initiative (motions to the game being played on ChessUp). I'm -5. My piece sacrifice didn't work, so I will resign and I will make sure to save that game and that way we can show it afterward.

Chess.com: Hopefully I was more successful in the interview than in my chess game! But, Jeff Wigh, co-founder of ChessUp, I really enjoyed our chat together and good luck with the product in the future.

JW: I really appreciate it, Mike. I really enjoyed it.

You can use the code CHESS to save 10% off at playchessup.com.