How Chess.com Became the World’s Top Chess App

the combination of the pandemic mixed with this massive massive hit TV show and that expanded the game in this just tremendous way that made it a huge part of the zeitgeist. The bridge from this point forward is a leaning into the productled growth stuff, right, which is really around experimentation and around continuing to refine both the product and marketing experience. So, we're just always like every day improving our user retention and our conversion. I'm challenging the team to get to a rate of around a thousand experiments per year.

To actually get to that number, that means the infrastructure and culture need to be great, but we also need to invest in no code experiments. We need to get our life cycle marketing team running experiments all the time, right? We need engineers to be able to kick off their experiments off of their ideas. We need to be able to analyze them quickly, etc. So, we want to definitely move into this like high velocity experimentation type of company. Welcome to Subversive, a podcast dedicated to sharing stories from the best consumer subscription apps in the world. We'll bring you lessons for how to grow your consumer subscription business, including insights and inflection points that led to exponential growth from leaders at category defining companies and innovative startups. Let's get into the show.

My guest today is Albert Chang, the chief growth officer of chess.com. Prior to joining chess.com a year ago, Albert served as head of growth and monetization for both Duolingo and Grammarly, making him one of the world's top experts on growing consumer subscription businesses. In this episode, I talked to Albert about chess.com's fascinating origin story back to 2005, its exponential growth during the CO 19 pandemic and the release of the Queen's Gambit and its more recent efforts to use productled growth to drive more sustainable, costefficient expansion. All right, welcome Albert to the Subversive podcast. This is an episode I'm particularly excited about both because you're a fellow consumer subscription nerd and because I've been playing chess my whole life since I was maybe three years old and chess.com is one of my favorite products. So super excited to have you on today and why don't we just

start with a little bit about your background and your road to chess.com. >> Yeah, thanks for having me Phil. Uh it's been really fun playing like daily chess games with you while riffing on uh chess ideas. So I can definitely vouch for your your interest in this topic. Um, yeah, my background in a nutshell, like I feel very fortunate to have worked on a lot of different consumer products really like apps that I use on my phone or my laptop every single day. And these include places like uh YouTube, SoFi, Dualingo, Grammarly, and now chess.com.

Um, so a really great, you know, swath of experience. Um, and really fun cultures to be part of, right? Because when you work at a company where the employees like just love using the product, they kind of quote unquote dog food it all day long and have lots of different creative ideas. It's just a really fun environment. So, I tend to gravitate toward that. I would also say like recently in my career, I found that this sweet spot where you can work on a product that's good for both uh learning and fun together, you know, it just feels really good, right? It's like it when you're building something people can actually improve and it's good for them but also they like intrinsically want to do it themselves and I really think that's a fun kind of mix. The last thing I'll say is like from a functional perspective I started my career in um engineering. So I have a computer engineering degree and then I shifted

over to like sales engineering and product management and then over the last kind of 5 years more of a focus on growth. So like in a nutshell kind of started my career like understanding and focusing on the code and then focusing on the user and now kind of focusing on growing the business right and I think having those different aspects has been uh really fruitful for my just kind of over overall understanding so yeah it's been a fun career path so far >> yeah that makes a ton of sense and you've had the enviable experience of working for a few of the top consumer subscription apps in the world YouTube Dualingo Grammarly all very big hits and now chess.com so excited to see you replicate that success and then as said you've worked across a number of different functional areas, uh, which I think is always an advantage as a growth leader because it's just such a multid-disciplinary role. Um, so let's

talk a little bit more about chess.com. This is a company that's been around a very long time. It's pretty obvious what the company does, right? It's in the name, but what what did the origin story of chess.com look like? And then how have they managed to become the number one chess app in the world with over 90% market share despite all of these other competing apps out there? >> Yeah, it's amazing story. Um, yeah. So, first of all, I'm about a year into the job at chess.com. So, you know, I don't give myself practically any credit for the, you know, the origin story, but as the lore has it, right, um, the co-founders, Eric and Jay, um, they met way back in in college, and Jay was the president of the chess club at the time, and Eric got really kind of addicted to chess through that experience. They became close friends, and Eric actually started a couple of chess companies before chess.com. Um, and so I don't

know if this is well known, but like he started a chess teaching business for like a hundred different elementary schools. And then he started a company called Wholesale Chess that actually sold chess equipment online. So very kind of SEO based e-commerce style business. And then lastly, you know, Eric and Jay noticed like there are places online to go play chess back in the day like ICC, um, Internet Chess Club, I think if I have the acronym correct. Um, and and there are others as well, but there wasn't necessarily like a fantastic user experience plus a community for people to, you know, really go play and talk about chess in the way that felt like home to them. And at the same time, this was back in 2005, they were kind of looking around at different domains and they were able to scoop up the domain chess.com from a bankruptcy option. I have to check my notes, but something around like $50,000

or something, which is just remarkable. Um, and kind of the rest is history, right? I think over these 20 years, they've really been a very missionoriented company. Like one of our missions is just to spread the joy of chess. Um, and to grow the game through that. You know, I I even pinged Eric on Slack. I was like, "Hey, you know, if you were to attribute like the success of this company like really pathy, like what would you say?" And he just say like in one word, it's passion, right?

It's just like this is a company of people >> that understands chess is more than a game. They feel like it's part of their, you know, identity and they want to serve chess in all their myriad of different ways. And, you know, Phil, you as a chess player, you know, how deep the rabbit hole can can get, right? >> Oh, definitely. >> Learning, playing, watching, and even the the kind of real life aspects of it. I have a four-year-old kid and I'm teaching him how to play. Um, and that's really uh great fun as well.

>> So, that's kind of the origin story. I'll pause there. Yeah. >> Yeah. There's so much about that that resonates. I mean, first you talked about Eric's passion and that was clear even the in even in the very a bridged version of the story you just told right he was very into chess had started multiple other chess companies was president of the chess club and so it's one thing to say you're passionate about a topic it's another thing to have a very clear throughine um from from a very early age and and that very much shows through and then I'll also say I have two daughters an 8-year-old and a 5-year-old and I've started to teach both of them to play chess probably the 8-year-old a little bit more successfully than the 5-year-old so far.

Uh, but it's already making its way into the fabric of my relationship with them. And so, credit to to the founders and to the team at chess.com for building a product that, as you said, goes far beyond the game itself. >> Yeah. And brain training is a huge theme right now for parents, too, right? So, chess is like a really great fit for that. And we actually have a kids app called Chess Kid, which is also a great product for for for kids since you mentioned it.

>> Yeah, we use Chess Kid, too. It's a great product. Um well let's get into

the inflection point that has really driven outsiz growth for chess.com over the last five years and that was the co9 pandemic and the launch of the Queen's Gambit which both happened around 2020 and and created this huge tailwind for the company uh for for the next couple years. So let's start with why did chess.com become so much more popular? >> Yeah. So I I would say first of all like the decade kind of leading up to the pandemic there was such a intense focus on like product experience community like just trying to build the best product combined with having the obviously the domain and the brand right so I already felt like it was well positioned and obviously chess.com had nothing to do with the pandemic right so really like I think that proved out where becoming a market leader in online chess prior to the pandemic really helped it ride its wave successfully.

>> Yep. So the pandemic I mean obviously as it forced people to stay indoors right a lot of people gravitated toward new hobbies and especially online entertainment like all these products kind of went through the roof in terms of demand and usage you know at the end of 2020 if my memory serves me correctly I think it was October 2020 there was also the release of Queen's Gambit right and Queen's Gambit which uh I imagine a lot of your listeners have have listened to it or have watched it but it's just this amazing story right it's a great great drama of this fictional American in like chess prodigy with drug and alcohol dependencies and it won 11 Emmy awards, all this stuff. And very quickly I I think the combination of the pandemic mixed with this like hit this massive massive hit TV show that actually even had a a female main character really, right? And that expanded um the game in this just

tremendous way that made it a huge part of the zeitgeist. And we saw in our registration numbers like north of a quadrupling right of like new registrations and that registration mix even skewing towards like different demographics like higher in you know female usage for instance than before. So it's a it was a really really you know whirlwind period for the company. Again I take no credit for that cuz I'm relatively new wasn't part of that. But just looking through our historical trends and our data, it's it's uh you know, it's definitely true that there was this massive wave in kind of late 2020, early 2021 that the company rose.

And then what's nice is that even though it kind of died down for a bit, it it still ended up kind of plateauing at a much higher level than before, which really speaks to the stickiness um and the sticking power of of chess as a subject. So yeah. >> Yeah. Well, and a couple things I'll say there. So, one is I had to drag my wife kicking and screaming into watching Queen's Gambit with me. She is definitely not a chess player, but she loved it. And you know, if you've watched the show, you can understand why. It's just such a compelling story and it gets into, you know, the rabbit hole and how deep chess can go if you were really passionate about it. Uh the other thing I'll say is having worked at Quizlet for three and a half years and helped build the growth team there. I saw something very similar like company was founded in 2005 just like chess.com for years and years it built a really

strong foundation tons of content you couldn't find anywhere else huge growth potential through both word of mouth and SEO and so there was this powder keg of potential energy that it was sitting on and it had already been growing exponentially before the pandemic and obviously there was a short-term period with the transition remote learning where growth slowed down but then as soon as that transition was complete the demand for online learning tools just exploded And so there was this similar effect where for a couple years uh after the pandemic started there was huge outsiz demand for Quizlet's products and so it sounds like you guys experienced something similar but fortune favors the prepared and so you guys were prepared and then >> I was going to say it's an overnight success but a lot of credit goes obviously to the hard work before that that time and >> yeah I'll also kind of add you know like

when these booms happen right naturally like all of your infrastructure like gets under crazy strain right so very very quickly you hit get in face of this just massive, you know, product market fit, if you will. And um I was kind of looking back at our product roadmap over the years and it's just like so much of the companies and the engineering emphasis was just on scaling up our infrastructure, right? So we' have a reliable experience that just literally worked because the demand was so um overwhelming. Um that that's I don't know just a really cool part of the kind of company's lore and has set us up, you know, even to this day to scale another 10x and beyond from here.

>> Yeah. Yeah. Well, and I'm glad you highlighted that point around infrastructure coming on strain when you have the good problem of super strong product market fit and explosion and demand. And I think it's an example of one of those unsexy, overlooked aspects of chess.com's product that you all didn't take for granted and really invested in proactively that has gradually over time set you apart from most of your competitors. So, what

strategies and tactics did the company use to lean into this big boom in demand? >> There are a lot. I mean, I can touch on a few. Um, I know I know we have a decent amount of time, but I'll I'll just touch on a few just to kind of get the conversation started. So, one was definitely around creator partnerships. And so, the company, and I give, you know, Danny Wrench and his team a ton of credit for this. They invested really heavily in relationships with both top chess grand masters like Hikaru and Magnus, but also like chess personalities, right, like Gotham Chess and Bes Sisters and many others. and they became uh just really an embedded fabric right of the chess ecosystem. If you go on YouTube uh or Twitch, right, these are creators that have grown tremendously over the past five years um playing their own games, live streaming their games, reviewing content, right?

And we find and we can see this in the numbers because we actually ask um new users in onboarding. We sample the how did you hear about us question and YouTube is like a top three channel for us actually. And so like it's no doubt that this has done a lot both for user acquisition but also user engagement, user resurrection. And it's that kind of content and product play together that make for a really like retentive uh loop for us. And so that was a a really big strategy that has that had paid off and will continue to pay off for sure is the creative partnerships. We lean pretty heavily into events and tournaments with I would say like mixed success in in certain areas. One thing that we still do today is these crossover tournaments.

You may have heard PogChamps since you're kind of in the chess scene. Um, and what Pogchamps is is like it's a we're trying to find like non-endemic chess creators, you know, people like uh Mr. Beast or even like Rain Wilson from The Office or athletes like uh Aarz from Crystal Palace, right? They like they like chess. They have a passion for it, but they're not necessarily like chess grand masters by any means, right? And so we set up this more um we kind of get these influencers to play each other right in chess tournaments and to stream it. That kind of crossover appeal has worked really really well and you can definitely see that in the numbers where we have these Pog Champs tournaments and we definitely see like meaningful user growth from that. We definitely also invested a lot in the high-end tournaments things like the champions chess tour and the speed uh chess championship and many many others. And

the chess calendar can actually be fairly like overwhelming. There's a lot of content that you can put that out there at all times. But we invested very heavily in a like uh worldclass kind of broadcast team to cover many different chess events. And you know it was a part of the strategy. It still is today, but that that part has been scaled back a bit. >> Got it. Yeah, that all makes sense. And I think the point you made in particular around bringing non-endemic chess creators into the fold is so important because it can make a game like chess that can feel intimidating or inaccessible to beginners feel like, oh, this is something anybody can play. And and then if you're smart about um which particular celebrities or influencers you're choosing, then you can target specific pockets of people interested in other things and bring them into the

game of chess. Were there any particular channels that performed best for you guys? You mentioned YouTube specifically. Have you done a lot on Tik Tok or Instagram or any other channels? >> Yeah. Yeah. I I failed to mention social media, but obviously that that's been huge for us. I think especially leading into the short form content. So Tik Tok and Instagram and YouTube shorts and on Twitter and and X and stuff, we tend to post stuff that can go viral, right? And I think uh this year, last time I checked, I believe we're projected like three billion impressions across the entire like social media landscape. So that's also been really really big for us. And we have a pretty big like long tail of um social media channels, but again it's especially the short form ones that tend to stick with people and get them interested.

>> That makes sense. And one thing I know you all have experimented with but ultimately decided not to do much of or really any of is paid advertising. Can you say a little bit more about that? I mean, is it just that you get so much organic growth through all of these other channels bringing people into chess.com or is or is it more about a philosophical decision around your growth strategy that has kept you from investing more?

>> Yeah, I would say it's honestly a mix. I think the philosophical part is is true and it it reminds me a bit of like Dualingo also had a philos philosophical opinion on this for for a while. I think they do some paid uh performance marketing now today. But yeah, I I think the part that is um probably true for us is that because we own the domain chess.com, we tend to rank just like organically very high on both SEO and ASO anyway. And so we tend that we don't necessarily need to market like chess.com. We just need to make chess in the ethos, right? And I think the Google Trends results for chess by itself, right, is a probably a pretty good proxy for like the demand that we get as a as a company and as a product. And so for the performance marketing angle, like we probably will lean into it more from a retargeting perspective of people that have tried the product, maybe they subscribed but they turned and you know

can we target them to kind of come back or provide them an offer or discount. So we might do it in sort of targeted places but I think that kind of generic like let's create a a Facebook or Google ad that just markets the chess.com and try to attribute like and try to make the LTB CAC math work out there. probably it probably doesn't and our smaller tests haven't indicated that in the past and so it just hasn't been a part of our mix. That said, companies mature and they grow and it might become a little bit of our mix in the future, but I can't ever imagine a a day where chess.com is primarily, you know, reliant on performance marketing.

>> That makes sense. And you would know the numbers much better than I would having worked at Duolingo. But my understanding is even now, many years after their founding, Dualingo is still spending a relatively small percentage of their total acquisition on on paid advertising. >> Exactly. It's very little. It's very targeted, right? Kind of country by country, specific channel. Like for instance, in Japan, we ran like TV commercials, right? Just to get the awareness high. You're solving a specific problem >> with a channel solution as opposed to applying a a blanket approach there.

That also resonates based on my experience at Quizlet which primarily grew through SEO and word of mouth and we would use paid advertising to target specific pockets of users. Those included teachers because they were super nodes in the network and they drove a lot of verality or as we were getting international markets off the ground then it can be a catalyst to jumpstarting uh new markets but otherwise it wasn't our primary way of acquiring users or subscribers. Sounds like it's very similar for >> and that said like you know the company I just worked at before this is Grammarly and I know you had Yuri in the podcast right and they very successfully into kind of performance marketing and you know for them I think as they shifted from students to professionals and we're working on like you know kind of growing the category and bringing that like dimension of oh yeah like I am writing a lot of kind of emails and

documents and I may make this kind of tone mistake or whatever right so like highlighting these pain points via like YouTube ads and other types of advertising was really successful for them. So again, I think I'm not trying to paint a broad brush of performance is good or bad, right? It's just got to fit for a company's uh kind of positioning and need at any given point in time. >> Yeah, totally. It makes so much sense and if anything, I see way too many subscription apps make the opposite mistake, which is they they become dependent on paid advertising way too early and then as they scale, CACs tend to go up, LTVs tend to go down as you move past your early adopters and the economics don't work anymore. So both Duolingo and Chess.com are good examples of companies that have managed to avoid that for a very long time. And you know at some point I would imagine you guys might spend start to spend a little bit

more just to lean into your momentum. But you you've been very successful without it for a very long time. So let's talk a little bit about coming off of some of these tailwinds as the pandemic subsided and as the uh boom generated by the Queen's Gambit started to die down. What were some of the media

bets that chess.com made above and beyond what you've already talked about? Yeah, you know, I will say like it's not necessarily that we were trying to completely like manufacture a chess boom, but but as I was just mentioned with the previous answer, right, we had a set of different kind of marketing strategies, right, that we're trying to lean in and test and see what they work. I think the part that I I kind of hinted at before about the the chess calendar for the top pro players, right? It can be very vast and today the prize pools aren't aren't as large as they will be in the future, right? And so to support and create our own kind of tournaments, it it is a big investment to go and do that. And I hope someday in the future I can walk in a bar and see some, you know, awesome chess match on TV or something, but we're not quite there yet. And so we've taken a much more kind of focused view on the types of chess

content that we're trying to surface. I think speed chess championship is a great example where they tend to be shorter games and then they're really highly kind of produced. We have great announcers on them. and we utilize like our game review feature and showcasing, you know, and making it more accessible to viewers, etc. And so, I guess what I'm trying to say is like kind of coming out of that initial boom, I think originally we had a more expansive strategy in terms of events and and tournaments and and since then we kind of dialed it down, but we've sharpened it, right? So, kind of higher quality, fewer events, etc. And we do find that that um is a compelling part of our ecosystem. So we'll keep it going, but it's just a little bit less of a a monetary investment, right? And creating prize pools and you know creating our own types of tournaments all the time.

We also have our titled Tuesday um event which is like every Tuesday I think there's two different kind of tournaments that top players go and log in. They go play on that site. So we like that type of stuff. It's kind of rinse and repeat and uh there's a prize pool associated with it and we know how to run it. we know how to track like you know fair play and all this kind of type of stuff. So that stuff is great combined with maybe like two or three big kind of temple tournaments. That's kind of where we're at right now.

>> Yeah. Well, it sounds like so many other growth bets where you started by doing things that didn't scale and ran a bunch bunch of experiments, tried a bunch of different things and sort of figured out over time which were the plays in the playbook that really led to positive ROI. And it sounds like that's been shorter games, speed chess, uh the rinse and repeat strategy of having celebrity grand masters come and play a game or two every week at scheduled times. Let's talk a little bit more about that latter strategy. So to what extent have top

players like Magnus or Gash really led to bringing either more beginners into the fold who just even if they're not big chess players, those names are so big that they've heard of them and they're curious or more advanced players who, you know, want to sort of follow in the footsteps of some of these grand masters. Yeah, I mean it's top of mind right now because there was just a Norway chess tournament, right, where Magnus and Gash played each other and Magnus pounded the table and it became this like viral meme all all throughout social media and I think you know moments and top personalities are a big reason why chess has like hit this >> kind of mainstream zeitgeist in a way that it hadn't before right and I think it also bridges the gap between kind of chess lovers and mainstream audiences with like really really serious kind of players and that's always been the concern is, right? Like we can lean into

um providing broadcast content for grand masters, but maybe it's a niche audience that will understand their play and appreciate their play. And so it's like how do we encourage and support and uh like love all the stuff that they're they're creating in their their tournaments, but do so in a kind of mainstream way and support that with our social media and support that with our kind of crossover events and brands and things like that. So, I don't know if that's a particularly clear answer, but that's that's how we've seen it play out.

>> Yeah. No, it makes sense to me. And I think my biggest takeaway from all that is in a world of streaming video, it just humanizes things like chess that can otherwise sometimes feel intimidating, inaccessible or dry. And Magnus in particular just has such a personality, right? He's like he's so emotional when he plays or he can be. And so when you see something like that where he pounds the table in frustration, I think every human on earth has had that moment where they've just hit their limit and they can't help but contain their frustration. And that's a deeply humanizing moment that I think draws people in. Um so to what extent have you

seen these media efforts drive impact for the business? How has it shown up in your metrics and where has it been successful and maybe where has it been less successful or less scalable? >> Yeah, for sure. Um, you know, first I'll kind of say that uh I never kind of went through like the the size of our our our business or anything like that. Would that be helpful too? Just to kind of give some >> Sure. Yeah. to the extent you can share.

I would love that. >> Yeah, I'm happy to. Um, I'll start at the high level. So, so first of all, our kind of market research shows that um around two billion people in the world have like ever played chess in their life, which is just a staggering number. And of those two billion, about 800 million or so have played chess recently. And most of that is um actually offline. It's just over the board, right? So a portion of that is online chess, of which we are a market leader for that. And that 800 million is actually somewhat comparable to soccer, right? So if you think of like the the breadth of people that have some exposure to chess, it is just kind of staggering to to even think about. Um on our platform itself, we just announced that we passed 200 million uh registered users. Um so that's continuing to accelerate and grow, which is great. Of those 200 million, about 40 to 50 million are monthly activives, about 10

million are daily activives, and we have just north of 1 and a.5 million subscribers as well. So we have a premium business model where like the vast majority of our user base um uses our product for free and then we convert some small percentage hopefully a larger percentage in the future but um that's kind of the makeup of it and the scale of kind of game play on our product and our platform is is pretty staggering like we are north of 20 million games played every day. Um and so to that earlier point about our infrastructure and our scaling, it's like very few companies at our size of kind of team members are also kind of running this type of um you know massive real-time gameplay type of system. Um so that gives a sense of the size and then you you were asking a bit about like the um how the media part kind of plays into that, right?

>> And so we we do see it in moments. So for instance the world chess championship um which was last um kind of December I believe right Gash was competing um in that and and actually became the world champion and he's from India right and so during those moments we're actually seeing like registrations in India surpass registrations in the US right kind of see these moments where >> there's this massive fervor that kind of gets built up within a country and we could see that very clearly in the data in kind of a more steady state environment again we asked the how did you hear about his question right and you can see like when there's a viral moment that uh or a post right that happens on Tik Tok or on on YouTube or on Twitter or something you can actually see that particular channel kind of like double or triple in like attribution quote unquote attribution it's not that that serious but it's directional right

and so you can see some of these channels sometimes climb from let's say like 4% up to 10% in a given week right just because of those those changes um this is a long answer but all that is to say like a big part of my job on joining the company is to help the growth be less lumpy. >> Because if you look over the last 20 years, we've ridden these waves and we have these just kind of like viral moments that give us growth from time to time. But really like the bridge from this point forward is a leaning into the productled growth stuff, right? Which is really around experimentation and around continuing to refine both the product and marketing experience. So, we're just always like every day improving our user retention and our conversion makes us more in control of our growth. And so, that that's really the the main focus of the company going forward.

>> Yeah, I love that. And I think that's a great segue from what got chess.com from its founding in 2005 to its big inflection point in 2020 to where it is now. And that's leaning more and more into more reliable and replicable techniques around product growth. I will say quickly as we jump into this topic, I was reading a blog post by Garav Vora who's another growth adviser subscription businesses recently. He was talking about what he called the Burge Khalifa versus the rising tide uh style growth wins. So burge khalifa would be like a one-time mega spike uh often from verality or some sort of really compelling performance marketing campaign or or an exogenous event that just happens to drive an explosion in in demand like the release of the Queen's Gambit that you were talking about earlier in the episode versus the rising tide which is the compounding effect of lots of singles and doubles to use a

baseball analogy. And I think one of the things that a lot of non-growth leaders don't necessarily appreciate is that a lot of the highest performing growth companies grow very quickly, not as a result of home runs, but as it's just the compounding effect of lots and lots of singles and doubles, high experimentation velocity, you know, relatively high hit rates, and then just doubling and tripling down on what

works. So, let's start with you've worked with some of the best productled consumer subscription businesses in the world. What are some of the lessons that you learned at Duolingo and Grammarly that you're now bringing to chess.com? >> Yeah. Um, and and you're right, it's really a game of compounding, right? It's like that 1.01 to the hundth, right? It's like you can really kind of consistently grow uh through that very reliably and especially in a premium business model where much of the game is like just growing the size of your daily active user base, right? And then converting that better and better that leads to to to higher revenue. And so I was reflecting on my career and I was thinking like for the first kind of decade of it, I really never even heard the term productled growth. It was just kind of like obvious like when you work at uh like a place like Google, right?

The reason people use these Google services, at least I thought back in the day, right? It's just that the the experience, right? And I think going into a company like Gramly that had a bit more of a hybrid type of go-to market model, right? like really helped me internalize like what productled growth actually means like sort of in practice. >> But anyway, at Dualingo and grammarly chest.com, like I I think of growth really as like it's the practice of connecting users to the value of your your product experience.

>> And again, it's that practice of like testing and learning as rapidly as possible. And so depending on where the company is at in its like mature maturity stage on productled growth, sometimes you kind of start with an investment in really it's like the infrastructure and the culture that comes first. I see you nodding and that that probably resonates to you, right? And it's like it does. >> If you don't have the event tracking right, if you don't have an experimentation system, if you don't have like a growth model and a set of key metrics that you're tracking, >> sure you can tell people to make up experiments, but it's not going to it's not going to work very well. you're not going to see that compound, right? And so that needs to be the foundation. You got to go build that and you have to teach the your team but also the broader company that like >> you know the purpose of all this

experimentation is to learn about your users, right? And I think when you can actually show with real data that hey moving like Xmetric up this percentage right can do this to this like our revenue or active user base and building these norms via like Slack or some other way where you have these kind of showand tell right like I I had this hypothesis I ran this experiment this actually gave me a different result than I expected this is the impact this is the learning you just get teams in this cycle of like trying things and sharing them with their co-workers It's it's magical and I get really like jazzed up about that because I think when you can create that culture within the company like the experimentation velocity will will follow and uh a company can can really grow and thrive off of that.

>> Yeah, I couldn't agree more and and you mentioned both infrastructure and culture in that order. To me those are sort of yin and yang because you first need the foundation of the right growth stack, the right metrics attribution, the right measurement systems. You need to make sure it's accurate and reliable. And that then makes it so much easier to get people excited about this culture of rapid experimentation, come up with a hypothesis, test it quickly. And I know you've only been at chess.com for about a year now, but what are some of the

specific steps you've tried to take as the now chief growth officer to instill that culture? >> You know, prior to 2023, the company didn't run really any experimentation. And so they started to kind of tiptoe into the space in kind of 2024. So a little bit before I was joining, there was already a little bit of momentum kind of built up. So it wasn't like I came in from the ground up like you know completely binary like we need to go try this the first time. But I helped kind of audit a bit about like our experimentation platform, which metrics we're looking at, what teams were more comfortable with experimentation versus not. Um some of these kinds of aspects, right? And I think ensuring that the data is as tight as possible such that the teams can actually analyze the experiments that they're running and come up with the right takeaways is so so critical. And when you come into a company, you kind of see some

inconsistencies around that, right? When that reliability and trust is a little bit lower, it could be hard, right, to get people kind of spinning on on on that wheel in a in a good positive way. Um, so that was a big part of it. And um yeah, again I think visibility of experiments both wins and losses is really critical and we try to do that both in Slack but also in all hands and other types of forums. Um repetition is really key as as a leader as you know right. So we just need to keep hounding that this is a a priority for the company and it increasingly is which is great to see >> for sure. One specific question I'll ask

you that I've been asked before is what do you think a good experimentation hit rate is? Is there a particular number you look for? cuz it's a little bit of a trick question in my mind, but I don't want to bias you. What's your take on this? >> Um, I think it tends to be lower than most people think. >> Y >> um I I have generally seen it more kind of like a 30 to 50% type of range. I think it depends a little bit on like again the maturity of like the part of the user journey that you're working on.

Sometimes it can be a little bit more obvious. So for instance, our modernization team when they first got set up, there was just a lot of lowhanging fruit that we could go and try and like most of those things would end up being winners just because we hadn't really touched that space too much, right? You could change some CTAs, you could follow some best practices. So like the percentages could be a little bit higher. Some things in trying to grow user retention are a little bit less intuitive. They're very kind of product and audience specific. Um, and so a lot of times like the the hit rate can be a bit lower there. And also I would say like different companies have different comfort levels with what they would consider a win right and so you know true >> depending on that right sometimes you're you're more willing to ship neutral things that you just your intuition is like yeah this is a better product

experience and other companies you're a little bit more cautious but yeah it's >> generally been my experience that about half of the experiments are kind of they don't really validate the hypothesis and you have a little bit of like fuzzy area where it's maybe gray area it's product decision and then you know 30%age is like, "Yes, this is great. Let's ship it." >> Yeah, that that resonates. I was going to say 1/3 to 1/2 has has generally been what I see. And there's sort of this analogy of an accordion that I use where you you eb and flow between cycles where you've identified a strategic opportunity and you're really leaning into it and there's lots of lowhanging fruit. So, you brought up the example of the monetization team just getting up and running at chess.com and there being lots of low hanging fruit and so that tends to lead to higher hit rates in some cases even when you're taking

bigger swings. Then at some point you start to tap out that strategic opportunity and so your hit rate starts to go down which is an indicator that you then need to go back into explore mode versus exploit mode and find the next big opportunity until you get the hit rate up again. But one of the other mistakes I see is this obsession around well we have too many failed experiments. We need to get our hit rate up. And so you're aiming for like 60 70 80% hit rates and what that can lead to is lots of small ball. You're just like doing micro optimizations that aren't actually moving the needle. And so I I love that answer. I think a lot of companies are too afraid to take bigger swings and fail because one of two things is going to happen. Either you're going to surprise yourself and get a big winner that generally if you're taking more risk is going to have higher upside or you know you miss but you learn from

your mistakes and and that leads to bigger and better things. So what are

some of the biggest AB test wins or failures that you've had since joining chess.com and and what have you learned from those? Yeah, a theme that continues to win here is around positivity. So, what I mean here is that like I I think as employees of chess.com, we probably skew into people that actually play quite a lot of chess. And sometimes you may have a blind spot that chess is just really kind of frustrating and intimidating for the vast majority of like >> newer users. And you know, we did an audit recently. We actually have a Slack channel is called like uh feels good man or something. It's just like we're looking at all the kind of cold experiences in our in our product where we're kind of calling out blenders or mistakes or putting red, you know, buttons in places that just not not intentionally make people feel bad, right? We probably did it for design clarity, but in a lot of those examples,

just making the slight tweak to kind of showing them and encouraging them that even after a loss, right, like losing is part of is part of learning and having coach say something positive or show some of the like the the positive glyphs in the game over modal. Um, another example is like our puzzle success rate when we actually looked at the data was actually relatively low, right? So, we built the infrastructure to be able to configure that and test that across different skill levels. And so, these types of experiments, we keep going to the well and like making improvements on again this positivity theme, whether that's copy, whether that's design, whether that's the underlying like logic system. We run experiments over and over and over and it's like it's always good for retention, at least so far, right?

I'm sure we'll tap out of that well at some point. U but that's been a great theme for us over this past year. >> Yeah. I mean the positivity thing doesn't surprise me at all. Both because it's chess, but also just because of where the world is at. People are stressed. They're stretched thin. I have this hypothesis that one of the biggest reasons meditation apps like Headspace and Calm have been so successful is less about meditation itself, although that's certainly important. And part of it, but part of it is just people need 10 minutes out of their day to just not do anything and to just sit down, lie down and take a break. And so similarly, chess.com serves multiple roles in my life, but one of them is just as an escape and I want to take 10 or 15 minutes and play a game. And sometimes I'm looking to maximize my rating, but sometimes I'm looking to just check out and and have a little bit

of entertainment. And so that positive reinforcement can go a long way. I guess now that you are in in the company and you've been there for a year, where do

you see what's your vision for what chess.com could look like in 2030 and then what are some of the specific strategies or tactics that you think the company will employ to get there over the next? >> Yeah, I mean I I can't wait man. I just seeing the evolution even over the past year I think will uh we'll be a really amazing company in 2030. Yeah, a few things come to mind. So, so one is you know how we work and I think experimentation velocity is actually a major part of this and so I'm challenging the team to get to a rate of around a thousand experiments per year which is really just an ambitious target. It doesn't mean that much but it's just a proxy right and that to actually get to that number that means you know again the infrastructure and culture need to be great but we also need to invest in no code experiments we need to get our life cycle marketing team running experiments all the time

right we need engineers to be able to kick off their experiments off of their ideas we need to be able to analyze them quickly etc so we want to definitely move into this like high velocity experimentation type of uh company that's one I think two um you'll increasingly see this virtual coach be embedded into our product experience um in game review, in puzzles, in lessons and we'll have a lot of different coach personalities embedded into that. I think this is a spot also where um kind of AI and LMS will obviously play a role, right? I think that's personalization, the ability to ask the coach just like a human coach, hey, what should I be training, you know, based on our um this personalized virtual coach experience, I think is really key for us and we're investing a lot there. And then I would say the third is you know as we think about expanding the game from let's say 10 million daily active

users to 100 million daily active users we definitely need to attract people that are have never played chess or just kind of chess curious. We need to make sure they have a really great kind of initial onboarding experience with us and like our social media needs to not just be tailored to these like again these kind of grandmaster events but really kind of break through right the mainstream zeitgeist um such that we grow the overarching like again the Google trends thing for for chess here.

So I would say like those three are top of mind for for for me and I think if we can hit on those and you know from now through to 2030 we'll be in a great shape. >> Yeah. Well the three things I heard there were experimentation, velocity, personalization and worldclass onboarding experience. And it's no surprise given you came from Dolingo that you are Dolingoifying the Chess.com culture. And obviously that that is a very good thing because Dolingo may be the single most successful consumer subscription app in recent memory. Um,

well, this is a great segue into our lightning round. So, I'd love to just close by asking you a few more light-hearted questions, some of them about chess, some not. And I'll start with what is the best part about working at chess.com. And what's one thing you change? >> Yeah, I mean, the passion for the product is unparalleled here. Like I I feel like I've worked at a lot of like great consumer subscription companies, but this is this is something else. I mean, it's like everyone here like plays chess every day, watches chess every day. It's just the the I don't know.

It's it's hard to kind of describe. Uh but I I I really love that. I feel like people are completely 100% bought in on um on the mission on on making the product and marketing experience as as great as possible. You know, there's a concept of like shadows of your superpowers in a way which is like because we are so committed to serving the overall chess ecosystem, right? like our mandate is very very broad and so we tend to say yes to practically everything and so you can go on our site and you see like we support all sorts of different things, right? And that makes prioritization sometimes a challenge for us. Um it's something we're getting better at being more intentional about where what people are working on, how to prioritize it, all that. But it's it's not as innately um obvious for us because we want to do such an excellent job kind of across the entire ecosystem.

But that's something that I I think we will get better at. >> Yeah. Well, weaknesses are so often the shadow side of your greatest strengths, to use your words. And it makes sense to me that when you have this incredibly passionate workforce, which is such a superpower and an unfair advantage, it can lead to a lot of like, well, let's do everything because we don't want to say no. It's just too much fun. And I can see how I know at Dolingo this very specific growth model around um daily active users being the northstar metric and then current user retention rate ended up being sort of the hero driver of DAUs like porting over some of that expertise and using it to identify the biggest explosive pockets of growth potential should help to provide an additional layer.

Um, so next question. How when did you learn to play chess for the first time and and what did you love so much about? >> Yeah, it must have been as a kid. I played a lot of board games with my dad and um I I still remember this like chess master 5500 game on like the CD ROM that I must played on the the PC. I don't know. It was it was making me nostalgic. I was doing a Google search of this this I definitely had that CD and and enjoyed playing that game. But yeah, I think what attracted me to chess is just it's it's a really deep like rabbit hole. I'm more competitive than I like to admit. So, I think it's like it's it's it's a great experience where you can kind of like once you learn the basics, um you can really feel yourself improving and there's so many different ways that you can, you know, do puzzles or lessons or challenge people or do daily games. There's many different ways to sort of interact with chess and I

think that has made it be kind of a part of my life. It kind of comes in and out, right? and I get addicted and then I it goes away addicted again. Now I obviously work at the company so I look at it all day long but um that's my journey. >> Yeah, I have a similar story. It was my uncle Richard who taught me to play when I was three or four and you know obviously I had no idea what I was doing but I just instantly took to it and strategy games in general have always been one of my greatest passions and hobbies in life but chess in particular is one of those things I keep coming back to no matter how many new games get invented. There's something about this ancient game that people can't stay away from and that's certainly been my experience.

>> So related to that, and you alluded to this in the Queen's Gambit, what are some of the things that you think chess can teach you about life? Like what what lessons can we extract from the way somebody plays chess or or the way that you ultimately win at chess uh or or lose? >> Yeah. >> Uh to to living a good life. >> The the lose part resonates with me, right? I think the uh I don't know the way that I said that makes me feel like a a terrible player, but yeah, I think there's this like mantra that we repeat internally like you you never lose when you learn. And I think that's a huge part of >> of chess because it's really humbling.

Like you lose 50% of your games, but if you take the time to internalize it and review it and improve, um that's what it's all about. And so life and chess are both about this like you're learning from mistakes, you're experimenting, you're feeling, you're getting back up um with better like knowledge and understanding, right? And I think that as a general principle, I think is a good thing for you to improve at really any craft, but I think chess makes that really, you know, pertinent in a relatively short cycle. And we actually see that like the vast majority of our business is predicated around like you're you're kind of a free user.

you're playing games and then you do game reviews to look at your like biggest strengths and your blenders, right? And then you play another game and then you try to do a game review again and then you upgrade because you want unlimited access to reviews, right? So that's really the the overarching reason why our business exists and that that kind of cycle again of trying something, making some mistakes, learning and improving is what it's all about.

>> Yeah. My biggest take away from that is people talk about having a growth mindset and not taking losses personally, but taking them as an opportunity to grow. And one of the things you mentioned there is by definition, unless you're Magnus or Gesh, you're going to lose 50% of your ranked matches because of the way the algorithm works, right? Your ELO rating is going to determine who you play next and they're always going to be right around your same rating, which means you're going to lose around 50% of the time no matter what you do. And that's a great metaphor for life. like if if you're winning all the time, you're probably not taking enough risk. And so, it's all about having the right attitude. So, a couple more here. Who is your favorite chess player? And what do you like so much about their particular stuff?

>> Yeah, I'll be honest. I don't think I'm good enough at chess to like fully appreciate all the nuances between the different grandmasters. They are so deeply prepared that it can be hard. Even though obviously as people they have like great personalities each. I'll I'll I'll answer this kind of tangentially, which is like I play daily games with a bunch of different people and one of the people I play with is uh let's just say he like works in sports and he plays like this hyperaggressive style. Um which is just fascinating for me. Like I really enjoy the challenge of seeing like a chess position that is kind of unique and makes me think a little bit. Um, I don't know if this resonates with with your own kind of chess journey, but I tend to find that I improve most when I play these kind of slower games or do puzzles or make the time to actually like think a few layers deep as opposed to just like playing a

ton of one minute or three minute bullet games where I'm just like going off of first uh, you know, my my first intuition. So anyway, I I I like seeing kind of players of any kind of skill level that have a unique style that just, you know, make me make me think about the game in a different way. >> Yeah, I couldn't agree more. And, you know, I'm I'm a I'd say I'm a solidly intermediate casual chess player, but I'm certainly it's not it's not so much of a passion of mine that I understand the nuances, as you said, the way the grand masters do by by any stretch. I have played some other e games, Hearthstone is one of them where I got really into it. And so like being a student of the game and the different styles and and realizing that your personality naturally lends itself to particular styles that are going to be more or less successful for you because of your nature. And so I think that's

always fascinating when you apply it to a game like chess. And I'm probably out of my depth in even saying this, but just to take two of the top players in the world right now, Magnus and Gh. They remind me a little bit of Maverick and Iceman from Top Gun, >> where, you know, you've got Gh who's just like so calculating and he he so rarely makes mistakes and so he's just going to like slowly wear you down until you make a make the mistake that causes you to lose the game. Whereas Magnus is much more of an intuitive player and he's more volatile, but he has such a powerful intuition that makes him unpredictable. And so, you know, I don't know if I have that right or not, but that's been my interpretation. Let's wrap up with the question that I often end these episodes with, and that is, how do you think AI is going to change the way that chess is played over the next few years? You talked about how

LLMs can be used to personalize features like coaches, but what else do you think will change about chess in the coming? Yeah, I mean I I I feel like I should answer this question by just saying like chess has uniquely grappled with this like existential question about whether like machines will take over humans since back like you know Deep Blue played Casprov in 97 right and it like AI has been used to try to solve this game of chess for many many many decades um and so I think that's been fascinating kind of place to start and then if you fast forward right over the last decade I don't think you'll find really any like serious player grandmaster not utilize, right, an AI engine like Stockfish to to prepare and review and have a deeper understanding of the game.

And so there's always been this symbiotic relationship, right, where you know, you're a human, you're you're playing chess, you're going to make mistakes, but you can also like train and review with the assistance of AI technology. And at chess.com like we've been working on making that technology which was historically kind of utilized to train grand masters that can now be used to train like a complete beginner in their basic games via our game review and other kind of adjacent features. So, I'm really proud that we've been able to leverage AI to kind of augment the the human playing experience and I think going forward, right? Um, we'll see more of that, right? So, I talked a bit about that personalized coaching. That's a big part of it. The the part of AI right now that is really hyped is around LMS, right? large language models and like language models themselves are not particularly good at playing chess which

is why we still use you know chess engines that are particularly trained at you know chess gameplay to do that behavior but I do think LLMs can help with the kind of conversation that you may have with a virtual coach right so kind of blending those two approaches is interesting and then the third dimension I'll touch on really briefly is on fair play right I think chess is increasingly a game I I shouldn't say increasingly but Um, we're getting better and better at detecting uh kind of cheaters and abusers on our site because we can detect and say, "Okay, based on your skill level and the difficulty of this position, what's the likelihood that you as a human, right, are going to come up with the engine best move here over and over and over again, right?" And so without revealing too much about like our fair play tech, right? We definitely leverage AI very heavily in that type of detection which creates for a fair and

clean playing experience for everyone, right? So, I think these are just a few examples of how AI's leveraged. >> I love that last example in particular. I mean, personalization is is obvious and the convergence between historical chess AI engines and now LLM makes a lot of sense, but I hadn't even thought about the fair play example. And it's yet another, you know, area where the craftsmanship that chess.com is bringing to its product just continues to create a wider and wider mode. as I knew it would be. This has been one of my favorite podcast episodes today, Albert.

So, thanks for taking the time. It's been such a pleasure talking to you. Any parting words you want to leave the audience with before we wrap up here? >> Thank you. Uh, this is fantastic. I love what you're doing with your community and podcast. Um, so no, not too much. I mean, I I feel like I should, as I talk about growth, I should give a shout out to my wife, Katie. I feel like um you know just the the reason for this is like in 2020 you know we were living in San Francisco and the pandemic had just started and I got this opportunity to join Duolingo. They were based in Pittsburgh and so my wife Katie was pregnant at the time and we didn't actually we had never been to Pittsburgh but we it required us to kind of relocate across the the country to have that experience and so I'm super grateful. I think a lot of career decisions in your life come through serendipity and through also through

like these like meaningful conversations that you're going to have with your wife and kids and other people and that really held true and I think without that experience I I might not have gone down the path of uh kind of consumer subscription growth. So that was super cool for me and uh yeah just wanted to share that story. >> Well I love that you did that and I feel the same way about my wife Ashley. um having having a supportive partner makes such a huge difference in so many aspects of life and career is certainly one of those. Thanks again Oliver. This has been a pleasure and um looking forward to more conversations about chess to come.

>> Look forward to it. Thank you.