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Erik Allebest: Scaling to $100M Revenue, 150M Members and 700 People, All with No Vc Funding | E1113

-Public.com is doing something no other brokerage has done before… they're sharing 50% of their options revenue directly with you… the customer. Get something back on every options trade. Oh, and there are no commission or per-contract fees, either. Go to Public.com and activate options trading by March 31st to lock in your lifetime rebate. -Merge is the leading product integration platform, offering a suite of unified APIs across key software categories—from HRIS to CRM—that allow organizations to offer hundreds of customer-facing integrations. Visit merge.dev/20vc to receive $5000 off your annual plan! ----------------------------------------------- Erik Allebest is the CEO @ Chess.com, the #1 online chess service on the planet with more than 150+ million members and 15+ million games played each day. Erik has scaled the company to over 700 people and $100M+ in revenue with no venture funding. ----------------------------------------------- Timestamps: (00:00) Intro (01:12) Early Entrepreneurial Ventures (04:44) MBA Journey and Embracing Risk (09:41) The Origin of Chess.com (13:52) Reaching the First Million Users (15:54) Achieving Product-Market Fit (17:54) Boost from Queen’s Gambit & COVID (18:30) Fundraising Challenges for Chess.com (20:49) Money's Impact on Self-Worth (23:20) Transformation Through Ayahuasca Retreat (29:37) Creative Acquisitions Strategy (32:16) Leveraging Affiliates and Ambassadors (33:39) Hosting the First Live Chess Event (34:25) Social Media Expansion Strategies (35:49) Unexpected Improvements by Keith Rabois (38:13) Evolution of Retention Rates (39:56) Defining Success Beyond Metrics (47:31) Capitalizing on Momentum (52:37) Transition to Post-Investment Phase (53:48) Remote Work Dynamics (58:20) Chess.com's Salary Insights (01:00:39) Discussing Capitalism 2.0 (01:06:05) Dealing with an FBI Call Over a Threat (01:08:39) Balancing Parenthood with Entrepreneurship (01:14:16) Insights on Maintaining a Great Marriage (01:19:45) Quick-Fire Round ----------------------------------------------- In Today’s Episode with Erik Allebest: 1. From Unemployable to $100M+ Revenue Founder: How did Erik make his way into the world of tech and startups? Was his MBA worth it? How does he advise others on whether to get one or not? What does Erik know now that he wishes he had known when he started? 2. Scaling to $100M Revenue with No Venture Funding: Why did no one want to invest in Chess.com in the early days? What did Erik do differently as a result of not raising any venture funding? What would Erik have done if he had money from the start? What are Erik’s biggest pieces of advice to founders with funding today? 3. Hard Lessons Scaling to 150M Members: What are 1-2 of Erik’s biggest lessons on how to scale users with zero budget? What customer acquisition worked? What did not work? How important was COVID and The Queen’s Gambit to memberships and sign-ups? What are the single biggest mistakes Erik sees founders make on customer acquisition today? 4. Parenting, Marriage, Metrics and Money: Why does Erik not care about money or capitalism today? How has Erik’s style of parenting changed over the years? What works? What does not? What does Erik believe is the secret to marriage? What have been his biggest lessons? Why does Erik hate metrics? If so, how does he run the business towards goals and output? ----------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZTtgTNBKwtZBMHvl?si=85bc9196860e4466 Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-twenty-minute-vc-20vc-venture-capital-startup/id958230465 Follow Harry Stebbings on Twitter: https://twitter.com/HarryStebbings Follow Chess.com on Twitter: https://twitter.com/chesscom Follow 20VC on Instagram: https://www.instagram.com/20vchq Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/contact ----------------------------------------------- #harrystebbings #20vc #venturecapital #business #podcast #youtuber #chessdotcom #chess #erikallebest #founderstories

Erik AllebestguestHarry Stebbingshost
Feb 7, 20241h 23mWatch on YouTube ↗

EVERY SPOKEN WORD

  1. 0:001:12

    Intro

    1. EA

      Chess.com is my third chess business, which is totally absurd to say.

    2. HS

      This is Eric Alabast, co-founder and CEO of Chess.com. He started the business in 2005. Now it does over $100 million per year in revenue. And the most impressive part? They did not raise a single dollar in venture. As a result of not raising money, did you do things differently?

    3. EA

      I mean, I had to do it differently. Everything I saw going on in Silicon Valley was like spend, spend, spend. We did the opposite. We thought about monetizing immediately. Everybody was remote. There was no office. I think raising money feels a lot like earning money. It's a self-validation.

    4. HS

      In the earlier years, was there a needle-moving moment?

    5. EA

      There were a couple of moments that things took off. So one was...

    6. HS

      Eric, I am so excited for this. Dude, I've got to hand it to you, you have the best headshot that I've ever seen, and we're gonna, we're gonna put it on social because everyone does, you know, like serious, looking into the distance, and you just smashed it. So thank you for being here, Eric. (laughs)

    7. EA

      (laughs) Thanks for having me. I try not to take myself very seriously. I love, I love dressing up in different costumes and being weird,

  2. 1:124:44

    Early Entrepreneurial Ventures

    1. EA

      so, uh, thanks for, thanks for using it.

    2. HS

      No, listen, dude. It kind of goes straight to our first point though, which is, you know, you love doing things that are slightly out there. I heard that your first entrepreneurial activity happened at nine. What was it? That's at, that's at a young age.

    3. EA

      Yeah, I was always, like, scrappy. And I don't know, like, my dad was the same way. He was always starting stuff, doing things. I did several things at a young age. I would sell things at school. We would sell, like, you know, either candy bars or bracelets or things. I would, uh, go to where the high school kids would drink beer and leave all their cans, and I would collect them all and go recycle them. I would go door-to-door to sell stationery. I was just always hustling for something, some way to kind of, like, you know, make money and, like, do something. So yeah, it's in, like, the blood.

    4. HS

      I have this theory that exceptional people show exceptionalism early in terms of entrepreneurial activity. (laughs) Do you agree with that in terms of the best entrepreneurs show entrepreneurialism early? I'm just intrigued.

    5. EA

      I mean, you probably have a... You probably look at a wider sample size than I do. I, I look at myself and, you know, obviously I did start young, um, and several of the other people I know have as well. But there's also some great, you know, later-in-life entrepreneurs who kind of did something and then they had, like, a, a moment and a spark. So, um, you know, I don't, I don't know. It's a, it's a fair thesis.

    6. HS

      No, no, you're clearly not a venture investor because if you were, we ignore the dataset that disproves our theory.

    7. EA

      (laughs)

    8. HS

      So there's still some training for you to do, Eric. Um- (laughs)

    9. EA

      (laughs)

    10. HS

      Luckily, luckily you're actually building value. I heard you say before that you're generally unemployable. Um, why do you think that and what makes you unemployable?

    11. EA

      You know, it's, it's kind of funny. I have, like, this thing inside of me that if it's, like, if it's my mission of th- something I want to do, I am 100% in, I am 200% in. If it's somebody else's thing they want, it just doesn't motivate me, and this is my dad and now my 15-year-old son is exactly the same. If he wants to do it, he's thousand... He just can't be stopped. But if it's something someone else wants him to do, he cannot be motivated. And so I don't know what it is, man. I, I don't know what the gene is. Maybe one day we'll know. But, um, you know, and it's not like I'm a non-compliant or disobedient person, but, like, if my heart's not in it, I can't get there. Um, but if my heart is, nothing can stop me.

    12. HS

      You said that your father was the same. Having watched him then operate, were there any takeaways for you and did that impact your mindset?

    13. EA

      Uh, I think my dad, he ended up doing something he loved, which was serving people in the legal community, but he really doesn't love being a lawyer. So he kind of, like, tried a lot of different things. And unfortunately for him, they didn't really pan out, and so he kind of always fell back. And, you know, he came from, like, a very poor immigrant family after World War II, you know, moved to the US when he was five and kind of really had nothing. And so he had a bit of that immigrant mindset where like, you know, be a doctor, be a lawyer, be a professional and you'll always be safe. But in his heart he was an entrepreneur, so he tried a lot of different things but always kind of fell back on being a lawyer. And he's great at it, he loves it. He does estate planning, so he works with great people and he's almost more of a therapist sometimes than a lawyer, but he had that fallback. And there was a part of me too that almost had a fallback too, where I was like, "Oh, I probably should go do..." You know, people are all, "Go do a JD/MBA

  3. 4:449:41

    MBA Journey and Embracing Risk

    1. EA

      and you'll have a fallback." And I'm like, "I don't know. I want to do chess or something." So anyway.

    2. HS

      That was going to be my question though, which is like, you know, bluntly, an MBA is a non-risky move. It is seeking security actually by definition. Brian Halligan at HubSpot said that recently because he did one too. Um, like, how do you reflect on that? Like, did you want to downside protect and how do you think about risk?

    3. EA

      I didn't really understand what an MBA was, so I didn't really view it as, like, a downside protection move for me or, like, a career advancement. I mean, it was literally... At, at first, a little bit I got some career advice. I mean, coming out of college, I was so lost because I was an English major, but I really loved technology and, like, entrepreneurship, but none of my education prepared me for that. And then I was just kind of scrappy and doing things, but, you know, my parents and my in-laws and everyone's like, "Hey, you need to go get, like, a real job and you need to go s- do some stuff." So I applied to, like, business school and law school. I didn't get in work- I didn't get in anywhere because it was, like, right after the dot-com, you know, bubble boost, uh, bubble burst in 2001. And I got rejected to every school. And I was like, "Oh, man." So then I'm like, "All right, I'm just going to go start and do something." And then later, it kind of was always in my mind, and then I got pretty unhappy, uh, in the entrepreneurial thing I was doing and thought, you know... Actually, it was my wife's like, "Hey, you need to go back to school. Like, you are miserable. Like, change pace, go do something." And so for me it was more of, like, an e- like, an exploration of myself and, like, what did I want to do, not a fallback.

    4. HS

      What did you learn about yourself then?... 'cause it's clearly been a clarifying moment for you. What did you change or learn about yourself through that process?

    5. EA

      Well, first of all, I learned that I, I was an asshole, um, and I wasn't a very pleasant person. And, uh, one of my dear friends out of business school, Andy Dunn, basically one day said to me, "Hey, let's have lunch." And we go have lunch and he's like, "Hey, you come off like an asshole all the time. You don't smile that much. You, you, you, you kind of, like, assume that you're in charge of everything that's going on. And, like, it's off-putting." And I was like, "First of all, thank you for being brave enough to tell me. Second of all, like, I'm gonna work on that. I'm gonna try and, you know, fix my RBF, my resting, uh, unhappy face."

    6. HS

      (laughs)

    7. EA

      "And I'm going to, uh, you know, try to be a bit more alpha minus where it's like instead of being control of every situation in the room, step in if people want me to or I'm willing to, but, like, leave some space for others." And so I learned so much about myself in that way. And I've really become a kinder, more compassionate, more self-aware person, you know, through Stanford Business School. I'm not sure that happens everywhere, but it really happened for me. Um, so that was one major takeaway.

    8. HS

      I think the show does very well because I'm always very candid with my own troubles. (laughs) Um, I, I have often been given the same feedback, but I also think, and I also get told by other people, what makes me very strong is the fact that I am kind of very direct, very concise. I don't mess around. And I will guide conversations in a productive way that leads to outcomes. It might not be the most emotionally tu- like, careful, but it's good. And so I, I guess, what would you advise me having experienced this and then also having come through it? I don't wanna lose the concision and productivity.

    9. EA

      (laughs)

    10. HS

      What do you say?

    11. EA

      It's not, it's not an either/or. It's not like be nice and then don't be direct. It's like you can be both. And I think a lot of it has to do with, like, the number of deposits and withdrawals you make in any relationship. And so it's like your bank account, so you need to have a way more positive interactions with someone if you're gonna have a negative or a more... or what they might feel as a negative or, or something. And so I do a lot of positive investing everywhere, with everyone in my company, with my kids, with my wife, with all my relationships. And then that, that builds up a buffer of trust and, and, and, you know, kindness and all that. So then if I have a moment of maybe clarity that feels a little bit stinging or a little bit too much or something, they already know that there's a good amount of goodwill that I've built up there. I'm accused of the same. I'm pretty brash at times. I'm not everybody's f- uh, favorite flavor of ice cream. And, uh, you know, that's all there is to it.

    12. HS

      Do you find it disheartening when you do a lot of deposits and then when it comes to withdrawals, people don't give in the same way?

    13. EA

      I have accepted that. So that's just a role, that's a position. That is just... comes with the territory at times of being sometimes a person in, in a position of power, frankly. I mean, I'm a CEO of a company of hundreds of people. Um, I'm a father of children. I'm the most pro- one of the most proactive of my friends in terms of putting activities together and keeping in touch and doing those things. I, I'm fine with that. I embrace that role.

    14. HS

      So we go through that process at business school and we kind of

  4. 9:4113:52

    The Origin of Chess.com

    1. HS

      come out a little bit more aware of who we are. How did chess.com come to be? 'Cause I know you bought the domain, I think it was in 2006. Talk to me about that process.

    2. EA

      Chess.com is my third chess business, which is totally absurd to say, but I did the, uh-

    3. HS

      It's amazing, it's amazing that you married such a wonderful person. (laughs)

    4. EA

      (laughs)

    5. HS

      A third chess business, I've never heard that before. (laughs)

    6. EA

      Yeah. Uh, so I started while in college kind of teaching chess to kids and setting up afterschool programs where lots of kids would come and, you know, I was basically a labor arbitrage business where, you know, 30 kids would play- would pay, you know, 15 bucks an hour to do an afterschool club, and then I would pay an instructor, you know, $50 to teach a class. And I did that in, you know, dozens of schools while I was in college and after. And then I kind of got this idea to franchise that business with this other science company that was doing the same thing, and then they needed chess equipment. So I started im- you know, buying chess equipment and reselling to them, and then I'm like, "I gotta cut out the middleman," so I started buying stuff in China. Then I had extra inventory and I was like, "I'm gonna start selling this extra inventory online." So I created a website with my friend Jay, we started doing basically like the amazon.com of chess before Amazon was doing anything except books. And so it kind of went from a teaching business to an e-commerce business. And then while I was doing e-commerce, I was like, "Customer acquisition cost is killing my business. I need to get off the Google AdWords or Google Ads at the time, build something that is meaningful for, for people and for users so they will come and do that activity, and then I can sell them some chess equipment." I was like, "I need to build a community. I wanna build the Myspace of chess. You're not gonna do that in an e-commerce site. I wanna do that on chess.com." So then I contacted the people who owned it, turned out they needed- they had like $5 million of, like, debt on the books and they needed to go bankrupt, so there's a bankruptcy auction, and I bought the domain out of bankruptcy, and me and Jay started chess.com.

    7. HS

      Okay, so a couple of different things. One, how big was the e-commerce site when you realized, "Hey, I wanna move into a community?"

    8. EA

      We were doing between one and $2 million a year in, I think, a little over 2 million a year in revenue and was making good, making good money.

    9. HS

      Yeah. Okay. And so then we get the domain name and through that process. How much did you end up paying for the domain name?

    10. EA

      $56,000.

    11. HS

      $56,000. At the time were you like, "Shit, that's a lot of money"? I mean, this is 2005, 2006. Were you like, "Hell, this is the most important address that we will have"?

    12. EA

      Yeah, I mean, it was a no-brainer for me. Uh, zero concerns dropping that money.

    13. HS

      When I spoke to Leo, he asked the question of how much of a role has the domain name chess.com played towards your success?

    14. EA

      Ridiculously large role, especially at the beginning. And the beginning sets the tone for later. Now, I mean, in today's world, if we hadn't done it, if you- would you have to start on chess.com? Probably not. But given the time that we started and how it worked and it was web first and all the... So it was critical at the time. And so by the time we hit the kind of mobile ecosystem where app downloads don't require a .com, and some people don't even have websites, et cetera, it's way less important now, but we were already massive at that time. And so-... it was fundamental.

    15. HS

      You buy chess.com, and then what? Because we, we can look at it today and it looks unbelievable. But like, how did you get the first million users?

    16. EA

      I opened up Microsoft Word and I started building wire frames in Microsoft Word. That's how, uh, (laughs) that's kind of where I was coming from. And, uh, you know, had a friend of mine from college design a logo, and then I kind of handed over this... You know, then I took these wire frames from Microsoft Word, and then I started building, uh, the front end of these web pages in, in, uh, Macromedia Dreamweaver. That's how long ago that was. And then I would build these web pages, push them through an FTP server to a fake domain name that we just, that I and my co-founder, technical co-founder Jay had, and he would take that HTML CSS document, put it in with some PHP and MySQL and, like, push it live to the server. And that's how we got started. And then so we built a homepage. We built a login. We built forums. We built blogs. We

  5. 13:5215:54

    Reaching the First Million Users

    1. EA

      built news. We built everything but how to play chess at the start. And we're like, "We're just gonna do a community and people can play on Yahoo or on ICC and then they can say what their rating is and we're just going to be a social media profile." But then people started coming and they're like, "Dude, we want to play chess." We're like, "Okay, okay, okay, we'll build that." But that was really hard to do because back in the day, people were downloading clients to play. Gaming was all done on, like, executable programs on your computer. Doing it in a browser was like an insanity at the time. JavaScript wasn't mature enough. There was no web sockets or anything like that. So, you know, that's a whole other podcast. (laughs)

    2. HS

      Okay, so how many users did we have, what, before we hit the actual chess playing, just on the community build?

    3. EA

      It was definitely under a million. Uh, but peop- every day, you know, a few hundred people would s- would, would sign up. I mean, maybe 1,000 or more would come to chess.com and then we would convert, you know, a fairly high percentage of them to just creating an account. But there wasn't a ton for them to do other than forums. But back in 2006, '07, '08, '09, forums was a big part of the internet. So it was, it was, it was popular.

    4. HS

      When in your mind did you have product market fit? When did you go to Jay, "We've got this. Like, this is good"?

    5. EA

      It was after we launched the learning product where you would go online and move a piece and it would give you a response, and we took basically all the learning instruction material that we bought out of bankruptcy along with the domain name, which was called Chess Mentor, and we put that online, and then we said, "If you want access to this, you got to subscribe." And once we did that, we immediately had people subscribing and we're like, "Now we have money. People are s- are voting with their dollars and saying we like this." And then we're like, "Okay, it's time to, like, 100% all in on this."

    6. HS

      At this time, what was the mission? I know it sounds like a strange question, but every company has a mission, you know. I think most of them are pretty fluffy and bullshit, to be honest. (laughs)

    7. EA

      Yeah.

    8. HS

      Um, how do you think about the mission then and mission-driven companies given this was the time when

  6. 15:5417:54

    Achieving Product-Market Fit

    1. HS

      you had to create it?

    2. EA

      Yeah, the mission was very clear- clearly to serve the chess community. And we were part of the chess community. I mean, Jay was a strong, you know, is a stronger chess player than me, uh, but I was very much into the game and we wanted to serve ourselves. We wanted a place that felt fun for us knowing that if we did that for us, we would serve the chess community more broadly. So the mission at the start was to, like, make cool stuff for the chess community. So for a long time it was serve the chess community only. It later became serve the community and, like, be the best place to work. And we kind of, like, it was very early on that we said, "We want this to be a place where we do things differently, but people really love working here and participating with us." So whether you're an employee or a contractor or whether you're a grandmaster, et cetera, you know, we want to be a great partner for you. And so we wanted really help, I wanted to make a place that I wanted to work, you know, again. So, so we did that and that became a second mission of ours. And then fast-forward when COVID came and the Queen's Gambit hit and our numbers, like 5Xed overnight, it grew the game of chess 5X. And we before that had never really thought that we had the tools to grow the game of chess. We thought that people who were interested were interested and we'll capture that and serve it, but we didn't think we could grow it. But now, our third mission is to grow the game of chess and we are doing everything we can to get more people interested in this game that we love.

    3. HS

      We're going to move actually to, to Queen's Gambit later on. I want to ask you just kind of stay with the chronology and kind of work through those different missions. You mentioned by adding the Chess Mentor, the learning, people paying for the product, and serving that community. When we think about the decision to raise or not raise, why at that time

  7. 17:5418:30

    Boost from Queen’s Gambit & COVID

    1. HS

      did you decide to not raise? 'Cause I'm sure you could have done. You were now making money. You had traffic. Things look good. What was that conversation like between you and Jay?

    2. EA

      Oh, no, we, we tried for, like, the first s- five years to raise money. (laughs)

    3. HS

      (laughs)

    4. EA

      We tried many times. We tried angels. We tried... I met, I met Peter Thiel. I went, I met le- a bunch of different angels. I went up and down, I used all my connections up and down Silicon, you know, th- you know Sand Hill Road to try to raise

  8. 18:3020:49

    Fundraising Challenges for Chess.com

    1. EA

      money for chess. And just time and time again was told, "The market's too small. This is uninvestable. Maybe I'll give you a little bit of money at, like, an insanely, like, low valuation." And I was like, "Uh, I don't need it that bad." So anyway.

    2. HS

      When you look back, did you do anything wrong? Like, would you have changed how you presented?

    3. EA

      Well, I mean, now knowing what I know, I mean, chess is a much bigger market. I don't think I did anything wrong. I think everybody was wrong. I think consensus, including from me, was that chess was too small. (laughs) And so why would you invest in a business that you thought would, you know, make $10 million in revenue at its best? Why would you do that?

    4. HS

      I'm just playing devil's advocate here, and I may be stirring the pot. What if they were right? Just pause and just se- and, and I... If you think about venture being $5, $10 billion outcomes, if we think about a $200 million revenue business, a $300 million revenue business, on public market multiples, you're looking at 6, 8, 9, 10X, it's still hard to see the $5 billion exit. Am I being short-sighted?

    5. EA

      I don't care about... I mean, the- I don't care about money. I'll be honest, I just don't care about it. And so it's just not the lens I look at. I mean, I think if you're a venture investor saying like, "Hey, I need to get to a $5 billion exit," like chess may not be your investment. And that's totally okay.

    6. HS

      Why do you not care about money? Just love to understand that. Like have you always been that way?

    7. EA

      I love experiences. I love having things. I love the security of, like, feeling safe and all, and having my needs, uh, and most of my wants met. But I, I know people where money is, like, self-worth or it's a scoreboard or it's, like, precious something. And I just don't know why I don't feel that. Like, I have friends who don't love food. I love f- I have a deep relationship and love of food, but I have some friends who are like, "Yeah, I eat when I'm hungry. And food is good." But I'm like, "No, no, no. I love food." Well, it's kind of the opposite. I like, okay, I appreciate money, but I don't love money or I'm not motivated by it. I don't care about it in the same way. I don't know why.

    8. HS

      I, I used to place a lot of emphasis on it, and it's like, pff, I am valuable because I have money and then I'm valuable to other people, which did not necessarily make me happy for

  9. 20:4923:20

    Money's Impact on Self-Worth

    1. HS

      a long period of time. Where do you determine your self-worth from, then? Because I think I'm in a bit of a self-discovery of like, if it's not that, then why am I valuable to someone?

    2. EA

      I would start and say, and this is something I, I, every human struggles with, but first question would, should be: Why are you valuable to yourself? If your entire self-worth is a reflection of other people, you'll always be chasing that mirror. You have to start with good, balanced self-worth and self-value. And that, that, and I'm not p- I'm not preaching to you. I'm not your therapist.

    3. HS

      No, you're not.

    4. EA

      But that's for, for me, and that's a struggle for me as well. Like, I'm a very extroverted person. I love being around people. I love doing all that. But self-care, self-talk, self-worth, all of that is, like, very critical to my well-being and makes me a better person to show up for others. And then also, that interaction is important. Anyway.

    5. HS

      How do I answer the question of why am I valuable to myself? Like, how would you answer that?

    6. EA

      There is, inside of all of us, an inner person, an inner being, and you have to get comfortable and happy with who that person is. And you can do that in a number of ways. Some people do meditation. Other people do alone time where they, where they can find peace in long runs or walks or other things. Other people get it from achieving something and being in the flow, and, you know, it could be skiing, it could be sports, it could be writing, it can be all sorts of things. But I think there's something about that. And, uh, you know, another day we could unpack, but I, I did do an ayahuasca retreat one time. It's the only drug I've ever done. Uh, I did an ayahuasca. And, and part of that journey for me was to get comfortable with myself and really be happy and, and s- and solid and f- and grounded in myself.

    7. HS

      When was that?

    8. EA

      Two years ago.

    9. HS

      Did that change how you operate as an entrepreneur?

    10. EA

      It totally did.

    11. HS

      How so?

    12. EA

      My biggest takeaway from this experience was... This is, this is so weird. I, I grew up, you know, in a, in a Mormon home and belief and culture, and I lived that lifestyle. I never did any drugs or alcohol. And so then to go do an ayahuasca retweet- re- retreat, I was so afraid to do that, to be in a mind, an altered mind state. But when I did that, it actually, for the first time, took all the other mind-altering things out of my mind, and I was present only with my mind. And my

  10. 23:2029:37

    Transformation Through Ayahuasca Retreat

    1. EA

      biggest takeaway from that retreat... And it took drugs to get me there. It's medicine. Sorry. For those who practice, it's called medicine. But it took a medicine drug to tell- to teach me that I am every day microdosing on drugs. I am microdosing on Slack, I am microdosing on email, I am microdosing on Zoom. I am under the influence of drugs every single day and every single moment of my life. And I am in an altered state because of that. And so I, uh, i- the most helpful thing from that was to realize that when I am feeling anxiety or when I am feeling something, I am probably... And I'm not centered, I'm probably under the influence of something. And it may not be a drug, as we characterize it, but it's probably Slack, it's probably a message someone sent me, it's probably a fear, it's probably something someone said on Reddit. I am under the influence.

    2. HS

      And so then you change what you do? Like, you can't avoid email. You can't avoid Zoom, sadly.

    3. EA

      No, but with just the recognition of saying, "Ah, I'm feeling this because of this thing, but I am actually a safe, like, grounded person outside of that. I am not my Slack. I am not my inbox. I am not my social media presence. I am something deeper, safer, more foundational than that."

    4. HS

      I love that. I, I've, I've never done an ayahuasca retreat. Um, I, I have done alcohol. I, I don't drink anymore. Can I ask, going back to the, the fundraising element.

    5. EA

      Yeah.

    6. HS

      When you go- You said you tried and it didn't happen. As a result of not raising money, did you do things differently?

    7. EA

      I had to do it differently. Everything that I... Everything I saw going on in Silicon Valley was based on large amounts of readily available capital. That means-... getting the best, you know, co-founder from, you know, Berkeley or Stanford or, and that means, like, setting up an office on, you know, California Ave. It meant having a full-time, you know, chef and masseuse in the office. It meant, you know, everybody hiring the best people you could, putting them in the office and, you know, doing everything right there. And later on, it meant doing everything in the cloud, and it meant buying ads on Facebook. It meant, you know, scaling up as quickly as you could. Everything was like spend, spend, spend, spend because eventually, eventually, you'll think about monetizing. We did the opposite. We thought about monetizing immediately. Everybody was remote. There was no office. Our engineers were spread all over the world. My co-founder was my college buddy from San Jose State and, you know, it was like everything was the opposite and because we had no money. And I'm really grateful for that. Sorry.

    8. HS

      So what... No, it's fantastic to hear that you don't need me and my whole profession. I'm thrilled. (laughs) Uh, just don't tell anyone, right?

    9. EA

      (laughs) Okay.

    10. HS

      Uh, uh, my question to you is having been through that experience, having done creativity because you had to, what do you think and advise founders when you see them today raising, again, more money than, than we ever thought possible?

    11. EA

      I think raising money feels a lot like earning money in that it's a validation. It's a per- it's a self-validation. "I'm, I'm worth the money. My idea is worth the money." It can fill a hole in your soul, and it can make you feel like you're going to be more successful because of it, and you can. I mean, honestly, there are a lot of businesses that need capital. Do not get me wrong. You... There are a lot of businesses that need capital. It's critical. It's important. You can't do certain things without it. You don't get immediate ROI. You need a runway. All of that is true, but there are times where I have seen people over raise money or raise money at times they didn't need it or pursue things within their business that were, were not right because they had money and knew they could get it.

    12. HS

      Where did not having money damage you? If you look back to the early days, where are you like, "Ah, if we had $5 million there, we really would've been in a different spot."

    13. EA

      It's very hard to say. I'm, I'm not a person who regrets very often or, or is, you know, backwards reflective in that way because everything turned out great. And I, I wo- I don't know what would have happened if we had hired a bunch of local people. Would we have moved too fast and done the wrong thing? I mean, there's something about moving slow th-

    14. HS

      Do you think, do you, do you think you went slowly? That's interesting.

    15. EA

      We definitely went slowly.

    16. HS

      Why do you say that though? I mean, uh, like, when you look at the trajectory, not, not that slow. I mean, companies that are venture-backed take as long as you did to reach the revenues that you did, the scale that you did. Like, I'm just interested-

    17. EA

      In 10 what years? I mean, that's a... (sighs)

    18. HS

      Sadly so, Eric, sadly so. (laughs)

    19. EA

      I just read about this game, Mike, and I'm gonna... I don't remember the title. There's just... There's a mobile game that launched literally last year in the last nine months that in that, those nine months did $400 million in revenue, some kind of like snow survival game or something, and I'm like, "I don't know, like, maybe I'm doing it wrong." I, I don't know. I mean, talk to Lior. He, he made a lot of money faster than, than chess.com did maybe.

    20. HS

      I mean, there's not... Lior is an incredible entrepreneur, so I'm very thrilled to have invested in him. Uh, but not having money drives creativity in a lot of ways, as we discussed.

    21. EA

      Yeah.

    22. HS

      Customer acquisition is one where traditionally you put money in the funnel. You mentioned the e-commerce business on Google Ads, Facebook Ads, put money in the funnel, and hopefully, it comes out with positive unit econ. You didn't have that money. So how did you do creative customer acquisition, and what were some of those big lessons?

    23. EA

      Yeah. We'd totally been burned on, on paid acquisition, and we pretty much made a, a, you know, a very firm rule that we weren't going to do paid acquisition. And so instead, we said, "We're going to take any money that we have, and we're going to put it into content because content drives user value, and, and it drives SEO." So we're... Our team has always been very good at, like, capturing demand on any platform, whether it's Google or, you know, app stores, because we create content. We create value. When people interact with that, you know, it signals to the search engines

  11. 29:3732:16

    Creative Acquisitions Strategy

    1. EA

      that it's something valuable. And so it's always been an investment in content. The next platform of discoverability after kind of Google and, you know, app stores was YouTube, and you gotta get content, and it's gotta be good, and then after that was Twitch, and we followed that, and then it was Shorts and TikTok, and we followed that. And so we always followed the content where it was and worked with really creative people and excellent people, and we invested in the product, and we invested in the content, and we invested in capturing search, but not paid. So I'm sorry to every- all the businesses that operate on, on, on ad revenue, but, you know, we don't participate in that.

    2. HS

      I'm really interested there because I mean, content's obviously my business as well. Did you do a portfolio approach and see what worked in terms of content channel, or did you just pick well each time? I'd just like to understand that transitory moment when you're deciding the next content platform to move to.

    3. EA

      I think we were smart about it. Um, one of my other classmates at Stanford... You asked about MBA, you know, is it worth it? I have some brilliant classmates, uh, from Stanford who've been really great to work with, including Andy, including Lior. Another one was Marcelo Camberos, who, uh, was at IPSY, and he and I talked early on, and he told me how valuable getting a YouTube influencer was to their, you know, uh, cosmetic subscription business, and I was like, "Okay," and I thought about that. And, you know, we started looking at that kind of, you know, early influencer, you know, market, you know, marketing, and we found some really great chess creators, you know, and, you know, we kind of started working that angle, and it was really valuable for us, super important.

    4. HS

      Did you-How did you pay them? What was that structure like? I'm intrigued.

    5. EA

      (laughs) I mean, it's always been a little different. We've... Some, some is through kind of like chess.com affiliate, so if someone signs up on chess.com and then they, uh, become a premium subscriber, they'll get a cut of that. Sometimes it was just some cash or an ambassador, like we would do a, a yearlong ambassador for, you know, some dollars. Also, we also create value for them because we then expose them to our community, and then they get bigger and make money in their own channels. And so sometimes it's a scratch my back, I'll scratch your back with embedding them on, like, our platform where people can discover them and then go to their platform. So it's kind of a range of all of those.

    6. HS

      It's really interesting, and it reminds me of Logan Paul actually and Prime, if you'll forgive me for that analogy, because, like, now they're such a big platform themselves that when they work with talent and influencers, they actually promote them too in a similar way.

    7. EA

      Yeah. Yep.

    8. HS

      And so, I mean... Would you have done anything different about content? You know, when I look back at mine, I would have moved to YouTube a lot earlier. I was too late to YouTube. Not too late. We're on it

  12. 32:1633:39

    Leveraging Affiliates and Ambassadors

    1. HS

      now, and we've done well, but I only did it two years ago, and I should have done it five years ago.

    2. EA

      Yeah, I think podcasting is a little different because there was, like, these other platforms. And then when did YouTube become a podcasting platform, you know? I think for chess, chess is visual. And so as soon as YouTube came out, we were like, "We want to do that." And as soon as... I mean, we were doing live streaming back when it was justin.tv, long before it was Twitch. You know, our very first live event that we really promoted was, you know, Danny Rensch, who's our chief chess officer, versus David Pruz, who was, you know, at the time our head of content. We put $1,000 cash on a plate in between those two guys on there and then had them play chess against each other. And that was kind of the beginning of our, kind of our live streaming. And so we had... So, you know, we would put kind of static content on YouTube that was in the, you know, 10 to 30, you know, minute range, and then we would do live shows on, you know, Justin.tv or livestream.com and eventually Twitch. But now we stream all over the place. But we were... And then, you know, Facebook was a different strategy. We would do a lot of quotes and, and memes there. And then Twitter was a little different. So we've actually been pretty smart on how each platform responds to the different types of content.

    3. HS

      What's the dominant platform today for you?

    4. EA

      A lot of browsers and a lot of providers have removed attribution to make it really hard to tell. So Twitch does no attribution. You know,

  13. 33:3934:25

    Hosting the First Live Chess Event

    1. EA

      Safari does not do attribution. And so it, it's gotten harder to tell, but we've seen a tremendous amount of growth. I would say our most recent wave was completely driven off of short forms, whether it's YouTube Shorts, Instagram, you know, uh, stuff, or Reels or, you know, TikTok. It is totally driven.

    2. HS

      So we actually have separate teams on a per channel basis. Do you have separate teams, or do you have, like, one social team?

    3. EA

      We have kind of one team with kind of experts and people who have feels for different things, and the, probably the smartest thing we've done is, like, old men step... you know, old people step out of the room and, like, hire smart young people and young women and, to kind of get in there with the voice and figure it out. And so it's just... I'm kind of a stand back and watch these young amazing people, like,

  14. 34:2535:49

    Social Media Expansion Strategies

    1. EA

      drive this stuff, and it's, it's incredible to watch.

    2. HS

      When you look at the membership scaling, was there needle-moving moments? We'll talk about Queen's Gambit. We'll talk about COVID. But in the earlier years, was it really a continuous up but gradual, or were there very strategic, like, significant moments where it really inflected?

    3. EA

      There were a couple of moments that things took off. So one was with the kind of Twitch creator, streamer, influencer. That was a big one. Another one, I'm actually going to give a shout-out to Keith. We talked about our, our, our mutual friend Keith. Keith was in the car with me one day, and he said, "Eric, I like chess. Sometimes I don't feel like I'm that, I'm that, like, smart enough to do it. And also sometimes I feel like it's too frustrating. And I go do the puzzles, and I feel like I get all the puzzles wrong. It's not fun." And I was like, "Man, Keith, Keith just told me that chess isn't fun, that doing puzzles isn't fun because he gets them wrong." And he... That conversation triggered us to build a product called Puzzle Rush, where you just start with all the easiest puzzles, and then they get harder over time. You feel all this success and all this easy fun, and then it gets hard, and you challenge yourself, and you fail. But that product was super needle-moving for us. It, it, it, it, it lit the world on fire. Malcolm Gladwell wrote about this product. Like, it, it, it was massive for us. And so there were just these little moments, whether it was product or content, that would,

  15. 35:4938:13

    Unexpected Improvements by Keith Rabois

    1. EA

      would inflame things and heat things up for a while, and then it would stick.

    2. HS

      Does Keith know that he was the reason that that was created?

    3. EA

      I know I told him, but he may not remember. But I did tell him that.

    4. HS

      How important is early wins in activities? And so, like you said there, about kind of the, the consistent winning early. How important is having early wins to the success of an activity?

    5. EA

      It pains me to say this, but somebody who wins their first game of chess is two to three times more likely to stay around than someone who loses their first game. And so then you're like, "Well, you've got to make sure that people win their first game." But doing that is, like, morally problematic in some ways. Do you make them play a bot so they, but they think they're playing a person? Do you set them up with an opponent who's super, you know, low-rated compared to them? Do you... And there's all these things you can do. But they all ha- There's moral hazard in all of it, and we've kind of avoided it. And so what we're trying to do is push people toward not playing a person first but knowingly playing a coach-bot personality where they will win and feel good but not to just throw them in the pool of players against other people where there's a 50/50 chance they're going to lose. That's the honest truth.

    6. HS

      2 to 3X more likely to retain. That's pretty incredible. Um-

    7. EA

      Yeah.

    8. HS

      Yeah, I was thinking, "Fuck, play a bot. Come on, dude. Think of our retention numbers."

    9. EA

      (laughs)

    10. HS

      Uh, c- can I ask, how have retention numbers changed over time? Have they stayed relatively stable? And, like, what is, what is... You know, I love Akin and Eyal because they're so fricking smart on retention, bluntly.How do you think about great retention and lessons from that?

    11. EA

      We are, we have not historically been a, uh, metrics-driven business. We're-

    12. HS

      Right.

    13. EA

      ... we've been a heart and mission and chest-driven business. We are getting smarter about it.

    14. HS

      How did General Atlantic take that? Like... (laughs)

    15. EA

      They, they knew who we were when they, when they, you know, married us, uh, but they've been very patient and helpful to, you know... They understand where we're at. Now, that's a whole other topic, but we've had a very good, um, coming together and seeing things. We started on different sides of the mountain, and we've come together to, to, to really understand each other. It's been actually really awesome. Um, wh-

    16. HS

      What... Do you know, do you know, like-

    17. EA

      What?

    18. HS

      ... t- talk to me about not being a metrics business. Like, why is it not better to be a metrics bus... Uh, just help me understand that

  16. 38:1339:56

    Evolution of Retention Rates

    1. HS

      because that is so different to what I normally hear.

    2. EA

      I know. I don't, I don't know what to tell you. Uh, we've always guided things through what we wanted to do and what felt right and what was in our guts and what was on mission and what sounded cool. And, you know, we've always done that. I think that was really healthy for us at the start. I think now having a blended balance of understanding those things, um, is helpful to us. But I do want to go back to the metrics-

    3. HS

      Ho- how, how-

    4. EA

      ... thing at some point. So I wanna... Yeah, go ahead.

    5. HS

      How do you determine success if metrics are not at the forefront of what drives decision-making? Like, obviously, I run media teams. We are very metrics-driven and that helps me assign success or not to someone in some respects. It's the joy of media in a lot of ways. (laughs) How do you determine success with no, with not a metric-first mindset?

    6. EA

      I mean, individually at the company, I think people don't think of success. I think they think of fulfillment. I think they think of effort. I think they think of mission and serving the community, and they take joy in that. And so if they do something that is well-received by the community or helps us grow the game, they feel good about that. And then, so then, uh, how would that manifest in numbers? You know, we, we, we track active users, we track subscribers, we track, you know, usage of different things. Um, and people kind of, you know, they know how many members we have and how that's going. And so it's just kind of a general happy-go-lucky feel.

    7. HS

      H- how-

    8. EA

      But there are numbers we're starting to look at differently.

    9. HS

      What numbers matter most to you today?

    10. EA

      You know, our d- our daily active user is a big deal for me, um, because it's very easy to just see how many people today are logging in to enjoy chess.

  17. 39:5647:31

    Defining Success Beyond Metrics

    1. EA

      That's very simple. Uh, there, you know, more though, I would say, we're s- we're starting to... You know, Duolingo, you know, their CUR metric was super valuable. Um, so we're now looking at that as a primary. So what this basically for the-

    2. HS

      Can you, can you explain... Yeah, can you explain what that means?

    3. EA

      It's kind of your, your retention rate of your active users, which means if somebody on week one was active and was again active in week two, what's the likelihood that they come back in week three? And so it's somebody who's shown a bit of a habit or, you know, they've shown that they're invested, they like the product, what's the chances that they'll continue to like it?

    4. HS

      And how does that differ from, like, a D30 number? Just so I understand that.

    5. EA

      I think that what it helps you see is not just like, "I logged in 30 days later," but that, "I made a habit out of it and I'm coming back regularly each week." And it's become, it's not just I... "Hey, I sent you a push notification on day 30, so you came back and did something." But it's like, "No, you made this a part of what you do."

    6. HS

      And so we have that metric, we have DAE. Any others where we're like, "Mm, this one"?

    7. EA

      So one of the ones that we're focusing more on now is a percentage of learners over players. Obviously, chess as a service, people come and they play. It's like the primary thing they do, um, whi- which not everybody does. Some people come and they still do forums or they watch our shows or there's other th- ... Or they, you know, different things. But the majority of people come and play, but not everybody turns into a learner. Our business is funded by learners. Playing is free, learning is behind the paywall. And so the percentage of people who want to learn and improve as a percentage of players is something that helps us understand that people are getting greater value out of our product than just playing.

    8. HS

      Can I ask, what percentage of people are learners versus players?

    9. EA

      It's different per product. And so we're trying, we're trying to kind of wrap it into one number, so I, I don't have that exactly. But, uh, you know, let's just say that of our active users, th- you know, it's, it's actually a strangely low number, but it's like 60% of our active users come in on a day and play. Half of them will do a... will do puzzles. So half of that number will do puzzles, and then half of that number again will do lessons. Game review is actually the most popular. A lot of people will do game reviews. So that's like a, a, a... Anyway, so we're trying to, we're trying to wrap that into a more cohesive product for everybody, but that is... Those are the three things that people pay for.

    10. HS

      That, that is really interesting. But actually that's, that's kind of more than I thought, still. I feel like if... On those numbers, it's kind of like 10%, really, if you think about it in that way, which is reasonably high actually, um, in my mind.

    11. EA

      So I'm... So just we, we could say we've got about 150, a little over 150, 160 million registered members. We have... Take a weekly active users is probably around 10% of that, around 15 million. About 10% of that are active subscribers.

    12. HS

      And active subscribers means they pay monthly.

    13. EA

      They pay monthly or yearly.

    14. HS

      Wow. What, what's the difference? Uh, 'cause... Sorry, I'm so interested. And anything that I'm prying too much, you can just say, "Harry, fuck off." Um, but, like, how many pay weekly versus yearly? What's that mix-up?

    15. EA

      The majority of people pl- pay yearly. Um, and most people do t- tend toward our highest paid product because they get the most access. And our retention on...... paid users is really good. Another one of my Stanford classmates, uh, Cadi Johnson, worked at Activision, and he's like, "Wow, I thought I had seen amazing retention numbers with World of Warcraft. Uh, you guys are up there as, like, very sticky subscriber base."

    16. HS

      What's your retention on paid users?

    17. EA

      I don't have the exact numbers, but I'm just saying, it's very high. But that changed. Sorry, ju- just to say, that changed when the two, we had two different, you know... I sent you our numbers. We got some interesting graphs where this kind of grew and then it had a, a Queen's Gambit bump, and then it had a more recent 2023 bump. The Queen's Gambit cohort, people saw the show, they saw chess pieces moving on the ceiling, and they're like, "I want to learn chess and get better." Those people, um, subscribed at a higher rate than norm- than normal baseline.

    18. HS

      What do you mean, what do you mean they subscribed at a high rate? There was more of them that entered the funnel?

    19. EA

      The percentage of people who became subscribers was higher than our previous kind of steady state cohorts.

    20. HS

      Oh, wow, did that-

    21. EA

      Because they wanted to be learners. They wanted to learn and get better, and Beth Harmon made them feel like they could be world champions. It was awesome.

    22. HS

      Did that bring in a load of low quality leads, though, which is like, "Yay, we want to be Beth Harmon. We want to learn," and then actually they're like, "No, fuck it, I've got kids and I'm busy and, uh," and they churn? Was that a leaky bucket, actually, or did they retain? I was really interested by that.

    23. EA

      They subscribed at a higher rate, but then retained at a lower rate, to your point. And that kind of, we swallowed that. But it's not like it went up and back down. It went up and stayed up significantly. So yes, it was net massive growth, but yes, they later s- retained at a lower rate.

    24. HS

      Yeah. That's what it is. Yeah, totally get that.

    25. EA

      But then we went to 2023 where the cheating scandal and Mittens the chess bot and short form content blew up, and then we also just exploded in schools. But now you have a whole bunch of high school kids and junior high kids and younger people getting into chess, and they subscribe at a way lower rate. And so registration numbers went through the roof, but our subscriber numbers didn't- didn't follow.

    26. HS

      Can I ask you, when you look at these kind of very strategic and clinical moments in the company's trajectory, respectfully, a lot of them were outside of your control, when we look at-

    27. EA

      Yeah.

    28. HS

      ... COVID, when we look at Queen's Gambit. No execution that you did drove that. No offense. Um, what do you advise an entrepreneur as given the serendipity, fate, luck of life?

    29. EA

      Be in the right place, man. Like, be- be paddling. We- we always say that we're in the boat and we are paddling and our sail is up, and we are, but we're also rowing. And when the wind comes, we're already ready and we're steering and we're doing the best we can. But we're not in charge of when the wind comes always. You can try. You can try to find the current and do different things. But, you know, you're not wrong that sometimes it's very, it's stuff outside your control that, you know, makes a massive impact in a business. And, you know, we've had several black swan moments, uh, compounding, and it's been pretty, pretty phenomenal.

    30. HS

      When you look back now, is there anything that you would or could have done to capitalize on the moment more, be more ready, had more content, had more products, done anything to capitalize on those two moments more?

  18. 47:3152:37

    Capitalizing on Momentum

    1. EA

      at the time, and we really feel lucky that our strategy was met with the, you know, the- the one-time, you know, exogenous event or whatever.

    2. HS

      Okay. And so we look at these very seismic moments that have incredible, trajectory-moving abilities for business. You then decide at some point, specifically in 2022, to raise cash from GA. Why did you just-

    3. EA

      Not, not totally accurate, but go ahead.

    4. HS

      Go f- No, go for it. I would, I, accuracy is important.

    5. EA

      After we were rebuffed by all investors early on, we kind of said, "We don't want to take any money. We're going to do this ourselves." Because before, we had no success and no one wanted to invest. Later, we had success and everyone wants to invest. And we're like, you know, "You can, uh, you can, you know, no, thank you." I have a lot of no thank you emails out there. I'm sure many people watching this program have gotten those no thank you emails from me. But someone came along and said, "Hey, I really love chess. Yes, I'm an investor, but I want to put my own money in and I want to just, I want to be, I want to invest." And- and I was like, "Okay, I live in Silicon Valley. One day I want to buy a house. Like, maybe some of us want to take some money off the table and we'll sell some sec-, you know, some secondary and we'll, you know, we'll do a little bit of a liquidity internally." And so we sold a small amount of, you know, 10% of the company early on. And that guy was like, you know, and he's like, "Okay, well, I need this preference and I need this thing." And we're like, "Nope, no deal. Go away. You're on the same terms as a- all of us or get out." And he's like, "Okay, okay, okay, fine. I'll- I will invest. Same terms as everybody, no preference, nothing, no guaranteed returns. I just want to own equity." "Okay, great. Now we're all on the same level." He invests 10%. He's like, "Ah, I love chess. I'm- I'm- I'm going to be an investor forever." "Okay, great." Fast forward a couple years. He's like, "Hey, I got to get out. I got some LPs that need some money." I'm like, "LPs? I didn't even know about this. Like, you told me you were going to be in forever." He's like, "No, no, no, I got to exit, but I got this other guy who loves chess. His name is Isai Scheinberg, founder of PokerStars. He loves chess. He wants to meet you." I meet with him. He's like, "Hey, I want to buy in. I want 50% of the company." We're like, "Get out of here."... we're like, "No chance, no way." And so, and he's like, "Okay, I'll do less, but we want these terms." And we're like, "Get out of here. No chance, no way." He's finally, he's like, "All right." So we come to terms and he buys like, you know, a little more, uh, more, a little more than 20 something percent. We're like, "Okay, we took a little money off the table." But he's like, "Hey, I love chess. I'm gonna be here forever." A couple years go by, he's like, "Hey, I gotta get out." I'm like, "Get out? Why? You love chess. What, and it's going well." So then he's like, "Nope, I gotta sell." And he's like, "Either I'm gonna sell to who I want to, or you guys can choose who I sell to, and you guys can do that." So now I start running this process where I start talking to all these people in private equity this and different, you know, venture firm there and all these different things 'cause I gotta buy him out. That's when we met GA. But again, it was to buy out existing equity. It was not to raise money. There was no primary money put in whatsoever. It was all just buying founder's equity, an equal ownership.

    6. HS

      Do you regret selling to that first investor?

    7. EA

      Totally.

    8. HS

      Huh.

    9. EA

      Every day. Every day, I think about it. I have-

    10. HS

      Really?

    11. EA

      ... I have so few regrets in life, but that is one.

    12. HS

      (laughs) What does that lead to?

    13. EA

      It's not a great thought. I don't like it. And, but I, we're here now, and so I have to believe that the best things happen and the universe will take care of it all. But I mean-

    14. HS

      How much, how much did you sell that first time 10% for?

    15. EA

      I actually don't remember. 20 million, I mean, 20 million valuation.

    16. HS

      Whoa. Okay, so you're talking like $2 million for the co-founders.

    17. EA

      Mayb- something like that.

    18. HS

      Wow, okay. And then, and then the PokerStars guy bought it at what price?

    19. EA

      Maybe around three times that-

    20. HS

      Okay.

    21. EA

      ... valuation.

    22. HS

      And then GA paid 10 times that?

    23. EA

      Yeah.

    24. HS

      Wow. Do you like working with institutional investors?

    25. EA

      I like Tenzin and I like Anton and I like Jesse and I like the people I work with. I have to say, I do like the people at GA. I don't want them to know that. So please cut that out. Just kidding, you can leave it, but I do like them a lot. Um...

    26. HS

      D- did... I, I do too. I've had Anton on the show. I've had Martin Escobari.

    27. EA

      Yeah.

    28. HS

      I think GA are one of the best, so totally. Did things change post having an institutional investor?

    29. EA

      Of course, it changed, but the mission didn't change. And I know you're like, "Ah, mission-driven, maybe that's BS." It's not BS for us because chess is like, it's a stewardship for us and we really do feel the mission. I don't know how to do a mission-driven insurance arbitrage business, but you can do a mission-driven chess business. Their view is drive, you know, maximum shareholder value. But you do that through serving your community and growing your game and building a great product. And our view is build a great product to serve the community and, okay, fine, it's gonna create shareholder value, but it's not... That's just, it's... We're looking at the same thing, but just opposite of each other.

    30. HS

      I get it. It's inputs and outputs. Driving shareholder value creates more enterprise value. That-

  19. 52:3753:48

    Transition to Post-Investment Phase

    1. HS

      would be infuriated to work with it. (laughs) But I bu- I, I totally believe it, and I think it's wonderful. Um, so I very much am l- loving it. You said something earlier, and you beat everyone to this trend. You said that you were remote from day one, and I wanted to talk about this. And, uh, you know, many of the mutual friends said we had to. (laughs) Can you help me understand? Why is remote work better? Because I can't think of a role which is done better remotely. And people disagree with me, and I'm always open to have my mind changed. So make the case for remote, Eric.

    2. EA

      First of all, talent is all over the world. And if you are geographically confined on talent, you have a smaller hiring pool, and you are now competing in ways, you know, that are hard. It's hard to compete against these massive dangled comp packages in certain areas and things. It's very hard. I would say that it's, it's been amazing to, to have an international team where we have people in India working with people in Serbia, working with people in Argentina, working with people in New York. And it's just a beautiful

  20. 53:4858:20

    Remote Work Dynamics

    1. EA

      thing. I don't know how to tell you. It is so beautiful. And because it's mission driven and because the weight... I always say the weight of our mission crushes egos. If you have an ego, this is the wrong place for you. Get out and go find somewhere you can serve yourself. The weight of our mission will crush you. It crushes politics, it crushes bullshit, it crushes egos. And so we're all there to serve the mission, and when all that other stuff is gone, you're now collaborating and serving each other to serve the mission. It, it works for us. And so we have really smart people who are passionate about what we do, who come from everywhere. And the other thing is they feel respected in their lives. They can show up to work when they want. They can do the work that they want. They can walk their dog in the middle of the day. They can take time off. They can do what they need to do. And so it is a joy for them to work. They don't feel trapped in the office. They don't feel like they have to show up early to do FaceTime. They don't feel like they have to be the last one to leave. They don't have to pretend like they're busy. It's so life-enabling to them that they're grateful to have the job and they give everything to it. And that includes me. I love my life. I love the fact that I'm sitting in a room and that there's no one around to bother me and that I'm doing this and I don't have to worry about if someone is judging me for how I'm spending my time or what's going on. So I don't know, it's freeing.

    2. HS

      Do you miss the human interaction and do you miss the creativity that comes from being in person?

    3. EA

      I have a lo- I am, I am married with four kids. I don't miss, uh, human interaction. I know that some people do, and that is a thing that, you know, they'll go to a coffee shop or they'll go to, at a co-working space or, you know... I, I understand that's a real part. It is not a challenge for me in my life.

    4. HS

      What have been the biggest lessons in terms of what it makes, takes to make remote work having done it since day one?

    5. EA

      I, I get this question sometimes. I'm like, "I don't know if these lessons apply outside of chess." So, uh, you know, apply with caution, but like being super mission-driven and having people who really are-... consumers of your own product. They live the chess world and life, so they get to participate in that thing. And the other crazy thing is that we are nobody's highest paying job. We immediately filter for highest paying. Like, if you are looking for your highest paying job, it will not be Chess.com. And so anyone who's hoping for that will go take a job somewhere else. And they are here for passion, and they are here, we pay as well as we can, but they're never gonna leave for money. They stay here for lifestyle. They stay here for mission. They stay here because we care about them and take care of them. But they're, but we don't churn people who are just constantly looking for the next most money they can make. Those people don't take jobs at Chess.com.

    6. HS

      When people have got through the door who aren't mission-driven, who do have egos, who do have desires on finances, it's inevitable they get through the door. What did you not see that you should've seen?

    7. EA

      Sometimes they say money doesn't matter, or they're, you know, and then later it becomes, you know, "Oh, I had a kid. I need this." I, you know, or a crazy offer comes in. We're, we're always like, "Hey, we're super happy for you. If that's now the important for you, go do that thing, that's great. We're happy for you." Other people will, you know... So, so it's usually a life circumstance will change. Occasionally we'll get like a bullshitter who will come through and suddenly they come in and they seem like the nicest person. Then they come in and they're like kingdom building and, you know, backstabbing and stuff. And we're just like, "Get out." Like, "Immediately get out."

    8. HS

      What are the biggest mistakes you see founders make when they're trying to do remote well?

    9. EA

      I think treating people like, kind of like assets, you know? Kind of treating people like workers who are supposed to do a job rather than like teammates who are on a mission to do something. Everybody wants to be respected and everybody wants to feel like what they're doing has meaning. And I think when people feel that it's like I'm task-oriented to do this thing that generates this that makes money, I know that's what a business is and I know that's what work is. But when deep down when you feel that, I think it's hard to show up when you feel that that's what you're doing. I think when you show up to work and feel like there are people that I care about who are relying on me, or there's a community that cares about what I do, it's very easy to show up for those people.

    10. HS

      Do you pay people according to national averages? You managed a global workforce. How do you think about, like, benchmarking and comp aligned to national average or same across the world?

    11. EA

      No, it's definitely nationally regulated. It's very hard to do. Compensation

  21. 58:201:00:39

    Chess.com's Salary Insights

    1. EA

      planning for a completely global company is super hard to do.

    2. HS

      Why is it so hard? And what have you done well at? Like, how do you do it well?

    3. EA

      I don't, I probably hired the first 300 to 400 people myself who worked at the company. And I would just say to them, "Hey, how much money do you need to do this job? And if we can make that, we'll do it. And if not, I'll let you know. But really, what do you need to do this? 'Cause I'm not gonna make you an offer 'cause I don't know your life. I don't know how much the average person makes around you. I don't know what your expectations are. So tell me what you need, and if I can meet that, great. And if I can't, hey, we part ways and we understand." And th- that's what we did. And people would say, "Hey, I can do this." And I would say, "Oh, that's great." Or, "Oh, I can't do that, this is probably my max here." And it's a take it or leave it. It's a little bit like that. And, and it, but what's been great is to see globalizing, like people, wages have gone up. Because someone who used to, in Serbia, worked for $9 an hour, now they have a global marketplace to work so that, their wages have gone up a ton. That's great for them and I'm happy, and we've tried to adjust and do all that we can. But again, some people just frankly wage out of our company, if that's what matters to them.

    4. HS

      When you said, "Hey, what do you need?" what percentage of the time did it come in above versus below?

    5. EA

      Probably slightly above more than, more than at or under.

    6. HS

      Speaking of kind of money and what you need, you mentioned Andy Dunn before. I spoke to him before the show, and he said that you're wonderful in many ways but you don't really like capitalism. What do you think he means by that? And you've mentioned before capitalism 2.0. What does that mean?

    7. EA

      If you look at the value structure of what's being ... I mean, this is age-old argument. It, look at the work that's being done by the people who are doing it. Look at the people who are managing those people, and then look at the people who invest in there, in the finance industry. And look at the where the value flows versus where the work is being done, and it's just disproportionate. And I understand that capital returns in a healthy market where people can invest their dollars to get returns is great for everybody's wealth creation, who has money. I understand that people having money creates jobs. I understand

  22. 1:00:391:06:05

    Discussing Capitalism 2.0

    1. EA

      that, you know, money does flow down even if, you know, trickle-down economics isn't totally, you know, whatever. I understand a lot of these things. But I also understand that, like, there's a driving human greed that makes it so that money doesn't flow in some ways to the people who need it or deserve it. And I don't know how to solve for this yet.

    2. HS

      What about ownership of companies? I mean this in the most non-provocative way. If that was the case, what about splitting ownership across the teams, giving everyone much larger ownership so you can have vesting schedules, but ensuring that the company is owned by the teams?

    3. EA

      I love this. I wish that it were easier to do. For example, the global system of legality is so hard and painful. The moment you are an equity owner, you have a K-1 in 37 states and 12 countries. And the tax bill alone for managing the equity st- tiny equity stake you have can be worth more than the equity itself. And it depends on your structures and your countries, but like, ownership is so hard to do.... and it's a real barrier to doing that. The other challenge is vesting schedules. So maybe someone owns, but someone comes in, works early, bails out. Now they have a bunch of ownership. Then, you know, but then they participate in all the upside of when they weren't there. And so there's a whole bunch of things around maybe the valuation when they join versus when they left, and they can capture that value. But there's a lot of problems. You dilute out and then... So, so ownership structure, in general, is just, is very problematic. I think that is where the answer needs to happen. But there's so much regulatory and legal and global stuff to fix around that before we can really get to that.

    4. HS

      It might be one of the only few truly crypto-native cases which make sense, actually. If you think about a decentralized ledger of ownership, which would be relatively, I guess, stateless in terms of governance and legislature, I imagine. I don't, I don't know. I'm, I'm bullshitting. But I'm a venture investor, so that's my job.

    5. EA

      Yeah, yeah, yeah. (laughs) Agreed.

    6. HS

      Uh, okay. When we think about that, I'm just fascinated. Like would you like to solve that? Or is that like, "No, like, I just think like that and, sorry, I'm too intrigued." Like you're an entrepreneur.

    7. EA

      It, it, it's possible in, like, my next thing. But I'm s- I am so overwhelmed by my current job that it's hard to think about anything else. But I have thought of that. Like, for example, let me just try this out on you.

    8. HS

      Yeah.

    9. EA

      What if there were a fund that only in, that invested in companies where they cap their returns and excess returns trickle down to the rest of everybody on the team? I mean, that sounds crazy because you're, why would you cap your return? Your whole joy, your whole thing is to get maximum returns.

    10. HS

      Why do I not sign up for that fund? (laughs)

    11. EA

      Yeah. I'll tell you what I did do. I'll tell you what I did do.

    12. HS

      Yeah.

    13. EA

      When our PokerStars investor, Esi-, you know, the Sheinberg family, when they exited to GA, I said, "I am going to block this transaction as hard as I can unless we set aside a huge percentage, comparatively, of the sale. Everybody is going to pay, I think it was 7% of their gains into a separate pool." This turned out to be tens of millions of dollars that we put into a separate pool, and then we now pay out to the people who were here at the company who did not have ownership, but we now pay out to them over a period of time that they stay working with us. We call it a retention bonus, but it's as if they had equity. And we, we, so we, we did not have to do this, but I forced tens of millions of dollars off of the gains of people who exited at that time to go into a special pool to reward the workers and the people who are here. And I'm gonna do it again. GA, if you're listening, I'm gonna do it again, um, and it's important to me that that money trickles down to the people who are doing it.

    14. HS

      Can I be so rude, Eric? And forgive me, I really like you, and I'm loving this. Do you ever worry... I, I worry sometimes that I'm too direct, I'm too confrontational by saying, like, "GA, I'm gonna do it." Do you ever worry that they go, "Hmm, not so happy about that"? No.

    15. EA

      I mean, they, they, they had plenty of time to get to know me before, before we did this. Um, you know, I think-

    16. HS

      I mean, no, listen, I, I totally get it, but it leads to my, to my next question, which is, you know, you mentioned, um, the tumultuous nature, um, of, uh, life, uh, in some respects. I do want to touch on Russia. You know?

    17. EA

      Yeah.

    18. HS

      You took the decision to speak up against Russia. And I, I think it led to a, well, you said a call from the FBI about a contract to kill you posted on the dark web.

    19. EA

      Yeah.

    20. HS

      Can you just take me to this? What happened? How did this go down?

    21. EA

      I was just standing at the whiteboard, like, talking about something with a friend, and there was a call. And, uh, it was actually the local police station which said, "Hey, have you talked to the FBI yet?" And I was like, "Uh, no." And they said, "Oh, well, they reached out to us to let us know about, you know, this death threat on the internet that someone had ponied up some money to have you killed, and the reasons were because of your stance on,

  23. 1:06:051:08:39

    Dealing with an FBI Call Over a Threat

    1. EA

      you know, on Russia."

    2. HS

      Why did you decide to take the public stance? Many didn't. Um, it can be unnerving for safety. Um, why did you decide to do that?

    3. EA

      Uh, taking a stand is hard, but sometimes you gotta do it.

    4. HS

      How do you draw the line on what stand to take? That's the hard thing of, like, Israel-Gaza. Do you take a stand there? Do you take a stand on US elections? Do you take a stand?

    5. EA

      It is all very hard, and I think, you know, we have not drawn very many, you know... We haven't taken a stand too many times.

    6. HS

      Why did you care?

    7. EA

      Russia invading Ukraine. We have a lot of team members in Ukraine. We have, we have a lot of team members in Russia, uh, who have m- mostly left. It, it was, it was very hard to see, and I, I feel like it's one of the great evils of, you know, the last few years is to see this direct assault. There are many other evils happening and, again, I'm s- I, I understand the hypocrisy of taking a stand here but not taking a stand there. But this is one of the most black and white issues out there. I would say Israel-Gaza is not a black and white issue. Um, there are... It's, it's mostly just a black issue across all the, a- all of it.

    8. HS

      Do you think politics has a place in the workforce?

    9. EA

      I think a lot of people who work for me think that it has a place in the workforce, um, workplace. We try to thread this in, in one way, which is to say we are not out there trying to have a stand on any particular issues, but our belief is that chess is for everyone, and that's an inclusive message. All people, all genders, all races, all religious affiliations, all everything.

    10. HS

      When you think about, like, moral stances to take, it's something that often parents instill on children. You have four children. Your eldest, I think, is 22. How old were you when you had your first, Eric?

    11. EA

      I had a pretty wild junior high. I'll just say that. No, I'm kidding. My wife hates that joke. (laughs) Sorry.

    12. HS

      (laughs) I was like, "Whoa. Oh, Lordy."

    13. EA

      (laughs) ... (laughs) No. I'm- I'm, uh- I'm- I'm in my, uh, mid-forties here. I had my first kid at 23.

    14. HS

      Did you feel ready? Were you scared?

    15. EA

      I was scared, but I was ready. I- I- I think being 23, for me as a person at that age, all that I had done in my life, ho-honestly, you know, some people are like, oh, late to launch or whatever. I was like early. I was one- I was a very mature early mature person, doing laundry by myself when I was, you know, a very young age, shopping, grocery shopping for myself, starting companies. Like, I

  24. 1:08:391:14:16

    Balancing Parenthood with Entrepreneurship

    1. EA

      just was... You know, I went and lived a- as a- as a Mormon missionary for two years in Argentina and washed my clothes, you know, the mud off my clothes in a bucket with my knuckles. And like, you know, I was just very young. I was put in positions of responsibility. So having a kid at 23 honestly felt like no big deal.

    2. HS

      What does great fatherhood mean to you? And how has your style of parenting changed over time? 23, now, you know, 45, um, how's that changed in terms of what being a great father means?

    3. EA

      Yeah. I'm learning still every day what it means to be a great father because it's different a little bit for each kid. I really try to meet my kids where they are and see the best in them. I think that some kids are easier to parent with certain styles than others. Some kids are more compliant. Some are more willing to please. My older two kids were easiest in some ways, and my younger two who are still at home are- are- are- have different challenges, and I'm learning there. But like for- I'll give you an example for my 15-year-old son. He's so incredibly bright, but he really doesn't love to have people tell him what to do. That includes... You know, but his sister's got... You know, she drives him up the- out the door at eight o'clock to go to school, but he doesn't want to be woken up. He doesn't want to be bothered. And so we finally said, "Hey, like, all right, we're not gonna set an alarm for you. We're not gonna, you know, take money from your bank account if you're late. We're not gonna do these things. Just good luck, man. Good luck." So if he misses school, he's got a Uber to school. He's gotta figure it all out on his own, and that actually makes him happy, rather than bumpers down the bowling lane. He wants maximum freedom with maximum consequences. All right.

    4. HS

      Do kids not need structure? No child wants a- an alarm clock. Of course they don't. No one wants to get up, generally speaking. It's- it's human nature to be inherently less, uh, alarm ready or whatever we wanna call it. Like, do you not need to do... Uh, uh, educate me, but do you not need to instill those guardrails?

    5. EA

      Some, it works well- it works well for some kids who understand that, and there's a little bit of friction, and you know, you kind of help, and over time they see and do those things. And that is true for some personalities. For other personalities, sometimes the best thing is just to get out of the way and let life take its course. So I'm not trying to say either approach is best. It's very kid dependent. But the more I tried to structure for my son, the worse outcomes he had. It was counterintuitive because it worked with my other kids and didn't work for him. And so I had to change- w- you know, my wife and I had to change strategies there.

    6. HS

      If you could call yourself up, Eric, the night before you became a father when you were 23, what would you tell yourself? You've got 22 years of wisdom now, and you can say, "Eric, you should know this." What would you say?

    7. EA

      Oh man, you're gonna make me emotional here. I think be really attuned to that ratio of positive, uh, versus negative, um. When you're a kid, you- you- you feel the negativity from authority. You feel the wrong that you do. You feel when you mess up. You feel when you disappoint. You feel, you know, you feel also heavy, and there's so much of it. You're getting so much correction in life. You're getting so many negative moments, and a lot of it's in the world, and if you're making your home also a place of negativity, you know, a lot of kids just wanna check out because they can't handle the negativity. So just trying to make home as positive as possible and have the most positivity, so that when there are those corrective moments, you have a lot in the bank. And I wish, you know, just... You- you cannot do enough. There's- there's no too much. Just do more and more.

    8. HS

      Did you have negative- too much negativity in that proportion?

    9. EA

      I think there were times and periods or certain areas with each kid where you really want the best outcome for them in this thing. And so as a parent, you- you fixate on it, and you try to, "Uh, I wanna fix this. I wanna control this. I wanna adjust this," and it turns into a lot of negativity, and you end up sometimes creating more problems than if you hadn't fixated on it and you had just left it be. And I can think for each of my kids different moments or things where I was really trying to control or, you know, guardrail or convince or do that and ended up in some ways causing more damage than if I had just kind of let- if I had let- shown more love and just kind of given them the time and space to get there rather than try to, you know, make it happen.

    10. HS

      Speaking of like making it happen, uh, I- I interviewed Harley, um, you know, the president of Shopify, and he said that when it came to marriage, the most important thing is actually not to provide a solution, and it's actually to make the person feel heard but not come in with, "Well, we can do this and this and this." When you think about lessons on what it takes to have a great marriage, what are some of your lessons there?

    11. EA

      The greatest thing you can do is validate and listen, and then when everybody feels validated and safe and heard and comfortable and, like, down to baseline and safe, then and only then can you have productive conversations around policy or decisions or different things. But most people get into escalating fights and arguments about trying to feel heard and validated, and if you can be the person in your relationship

  25. 1:14:161:19:45

    Insights on Maintaining a Great Marriage

    1. EA

      when there's tension to just stop and say...... I'm setting my issues aside and I'm going to listen to this person as a human and what their needs are and what's driving them and what their feelings are, and listen and say, "I hear you. That sounds hard. I understand. That makes sense. I feel that." You help that person then feel safe as a person. And then hopefully they'll take the time in their turn to then listen to you and do the same for you. And then when you come together, then you can start possibly then or later to work on solutions to the problems 'cause there are- there can be real problems. And just validating feelings doesn't solve problems, but you have to start there.

    2. HS

      Have you always shown the true full extent of yourself? If we're honest, I don't show the full extent of myself because if you knew what I was like, you would leave. (laughs) Like, I guess that's human nature? Like, do you show the full-

    3. EA

      It's not my nature, if I'm honest.

    4. HS

      So you show the darker steps of yourself?

    5. EA

      I don't feel like a dark person. I feel like a needy person sometimes. I feel like a confused person.

    6. HS

      Do you feel the need to always be strong?

    7. EA

      People love, like, reality. People love vulnerability. Um, people love self-deprecation and humor and just, like, real. People love real. It's just- it's always been who I am. I- I don't have the- I haven't had the drive to do that. And I think I had a safe home where I felt like I could be myself, and I grew up that way feeling very self-assured and have had friends and people who just love me for who I am. And I'm not a perfect person and I make a lot of mistakes and I have character flaws for sure, but I try to lead with- with- with humility and with, like, you know, acceptance of who I am and who everybody is. And I've found that that's created really great relationships.

Episode duration: 1:23:21

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