Erik Allebest on Building Chess.com, Growth and Life Beyond Metrics

Erik Allebest says Chess.com grew by monetizing early, building remotely and investing in content rather than relying on venture funding. The co-founder and CEO joins Harry Stebbings to discuss the company’s history, its changing growth and ownership, and his views on work, family and money. Company figures are his account at the time of the interview.

Allebest remembers selling goods at school, collecting cans for recycling and going door to door as a child. He sees entrepreneurial behavior in his family but is cautious about assuming every great founder shows it early. Some people discover their ambition later, he says.

He jokes that he is unemployable because he can devote extraordinary energy to a mission he chooses but struggles to be motivated by someone else’s. His father tried entrepreneurial projects while falling back on a legal career. Allebest also considered a conventional fallback before finding his way into chess businesses.

An English major interested in technology and entrepreneurship, he initially applied unsuccessfully to business and law schools after the dot-com bust. Later, unhappy with the venture he was working on, he went to Stanford business school partly to explore what he wanted rather than as a carefully planned safety net.

A classmate, Andy Dunn, told him that he came across as unpleasant and too eager to control a room. Allebest appreciated the candid feedback and tried to leave more space for others. He says the experience helped him become kinder and more self-aware.

Stebbings asks how to remain direct without losing productivity. Allebest says kindness and clarity are compatible: positive interactions build a reservoir of trust, making a difficult conversation easier to receive. He tries to invest in that goodwill with colleagues, family and friends.

Chess.com was his third chess business. While at college he organized after-school chess classes, then sold equipment to programs and eventually built an online chess retailer with his friend Jay. The businesses gave him experience serving the community before the website became a place to play.

Paid search acquisition was expensive for the retail business. Allebest wanted a chess community that people would visit for its own value, initially envisioning a social network rather than an online game. He purchased the Chess.com domain and learning material from a bankruptcy auction for $56,000.

He credits the domain with a particularly important role in the web-first early years, though he says it would matter less in today’s mobile app ecosystem. He began with wireframes in Word and front-end pages; his technical co-founder Jay integrated them into the site.

The first version offered profiles, forums, blogs and news but no chess games. Users asked to play, so the team built that capability despite the technical difficulty of browser gaming at the time. Early traffic and forums provided a community, but paid learning became the clearer sign of product-market fit.

The company put its acquired Chess Mentor material online and offered it by subscription. When people immediately paid, Allebest and his co-founder saw evidence that users valued the product and committed fully. Their initial mission was to make useful, enjoyable things for the chess community they belonged to.

A second mission was to make the company a good place to work and a good partner for contributors. After COVID and The Queen’s Gambit dramatically increased interest, Allebest says the team added a third ambition: actively grow the game. His description of the size of that surge is a company recollection, not independently verified measurement.

Contrary to a simple story of deliberately avoiding outside money, Allebest says the founders tried to raise capital for roughly five years. Investors repeatedly viewed chess as too small, and the terms offered were unattractive. He acknowledges that the founders themselves also underestimated the potential market at the time.

Stebbings questions whether a chess business could satisfy a venture fund seeking a multibillion-dollar exit. Allebest accepts that it might not fit every investor’s requirements. Money provides security and experiences for him, but he says he no longer treats it as the primary measure of his own worth.

He encourages starting with a sense of self-worth that is not entirely dependent on others’ approval. He says this remains a personal struggle too, and different people may find grounding through solitude, meditation or activities that absorb their attention. He does not present himself as a therapist.

Allebest recounts an ayahuasca retreat that he says changed how he understood distraction and anxiety. He describes Slack, email and social media as influences that can pull him away from a grounded sense of self. This is his individual interpretation of an experience, not evidence that the substance or retreat is appropriate for others.

Without outside financing, the team had to operate differently from the spending-heavy Silicon Valley model he saw around him. It sought revenue immediately, worked without an office and hired engineers across the world. He is grateful for the constraints, while acknowledging that many businesses genuinely need capital and runway.

He warns that fundraising can feel like earning money because it validates a founder and an idea. Capital can be essential, but he has also seen founders raise too much or pursue the wrong activities simply because money was available. He cannot know whether an early $5 million investment would have improved Chess.com or encouraged mistakes.

After being burned by paid acquisition, the company made a rule against it and invested in product and content instead. Allebest says valuable material helped capture existing search demand and supported discovery in app stores, YouTube, Twitch and later short-form platforms. This is his account of the company’s acquisition strategy.

A conversation with a Stanford classmate about influencer marketing encouraged him to work with chess creators. Arrangements varied: affiliates could receive a share when users became premium subscribers, some creators received cash or ambassador fees, and exposure to Chess.com’s audience could also help their own channels.

The team adapted formats to each platform, from longer YouTube videos to live streams, social posts and short clips. An early live match featured Chess.com staff playing for $1,000 placed between them. Allebest says modern attribution is harder because some browsers and platforms limit tracking.

He credits a recent growth wave to short-form video and says the company relies on people who understand the voice of each channel. Rather than dictate every creative choice himself, he describes giving younger colleagues room to experiment. Twitch creators had also helped generate earlier growth.

A conversation with Keith Rabois revealed that chess puzzles could feel discouraging when players repeatedly got them wrong. The team responded with Puzzle Rush, beginning with easier puzzles before increasing difficulty. Allebest calls it a major growth moment and an example of making the game feel fun before it becomes challenging.

He says players who win their first game are two to three times more likely to stay than those who lose, according to the company’s observation. But he sees ethical concerns in manipulating that outcome. The approach he describes is to direct beginners knowingly toward a coach bot, rather than disguise a bot as a human opponent.

Chess.com historically followed mission, intuition and what felt enjoyable more than a strict metrics-led process, Allebest says. With General Atlantic as an investor, the company has become more deliberate about measurement. He describes that relationship as a gradual meeting of different perspectives rather than an abandonment of its mission.

Teams seek fulfillment in serving the community, but the company does track active users, subscribers and product usage. Daily active users matter to Allebest because they show how many people are enjoying chess. He also discusses a retained-user metric intended to identify recurring weekly habits, not just a single return prompted by a notification.

Another question is how many players become learners. Playing is free, while the company’s business is funded by paid learning features. He gives approximate usage proportions across playing, puzzles and lessons but says the company is still combining these into a coherent metric; the categories should not be assumed to be identical to paid conversion.

At the interview, he estimates more than 150 million to 160 million registered members, around 15 million weekly active users and roughly 10% of those weekly users as paying subscribers. These are approximate, different populations, not 150 million active or paying users. He says most subscribers pay annually and many choose the highest tier.

The Queen’s Gambit cohort converted to subscriptions at a higher rate than the prior baseline, but later retained less well, he says. Even so, the surge left the business significantly larger. A later wave in 2023 brought younger players through short-form content, a chess bot and public attention, but converted to paid subscriptions at a lower rate.

Stebbings notes that pandemic conditions and the television series were outside the company’s control. Allebest’s metaphor is to keep rowing with the sail up so the business is ready when the wind comes. He credits luck as well as earlier work to make puzzles, bots and content more welcoming.

Stebbings describes General Atlantic as a 2022 fundraise, but Allebest corrects him: the transaction bought existing equity rather than putting primary capital into the business. After early fundraising rejections, the founders had decided to continue independently, though they later allowed some shareholders to take liquidity.

He recalls selling about 10% to an initial investor on the same economic terms as the founders. That investor later sought an exit, leading to an investment by Isai Scheinberg. Scheinberg subsequently wanted to sell, and Chess.com chose to find a buyer, leading to General Atlantic’s purchase of existing shares.

Allebest says he regrets the first outside sale because it set this sequence in motion. He recalls a roughly $20 million valuation for the first transaction, a later price around three times that and General Atlantic paying roughly ten times the subsequent price. These are his approximate recollections of valuations, not audited transaction disclosures.

He says he likes the people he works with at General Atlantic even though the relationship changed the company. He describes a difference of emphasis: the investor seeks shareholder value through serving the community and building a product, while the founders start with that mission and see shareholder value as an outcome. Both have financial interests in the company.

Allebest makes the case for remote work: a global talent pool and flexibility can attract people who care deeply about the mission. He believes employees benefit from being able to organize their lives without office-presence rituals. He also acknowledges that his own family gives him social interaction that other remote workers may need to seek elsewhere.

He cautions that lessons from Chess.com may not apply universally. In his account, the company attracts people motivated by chess and lifestyle rather than the highest possible salary. He says people sometimes leave when their financial needs change, and the company should be happy for them rather than pretend compensation does not matter.

For remote teams, he emphasizes treating people as teammates with a meaningful purpose rather than interchangeable labor. He says compensation varies by country, and early on he often asked candidates what they needed rather than relying on a global pay formula. He describes both the difficulty of worldwide benchmarking and rising access to global labor markets.

Allebest questions a system in which financial returns and the work creating value can be unevenly distributed. He recognizes that investment creates jobs and can build wealth, but believes greed can prevent gains reaching people who contribute. He says he does not yet know how to solve the problem.

Broader employee ownership appeals to him, but he describes legal, tax, international and vesting complications. Stebbings speculates about a possible technology-based ownership system; neither establishes that it would resolve those issues. Allebest also floats a hypothetical fund with capped investor returns and additional gains shared with employees.

He says that when the Scheinberg holding was sold to General Atlantic, he insisted that a portion of sellers’ gains be set aside for employees without equity. He recalls roughly 7% of gains, amounting to tens of millions of dollars, funding retention payments over time to people who remain at the company. These figures and conditions are his account.

Allebest recounts a call from local police who said the FBI had alerted them to an online death threat connected to his stance on Russia. The interview does not independently establish who made the threat or whether it was actionable. He says Chess.com had employees in both Ukraine and Russia and explains why he chose to speak about Russia’s invasion of Ukraine.

He acknowledges the difficulty and inconsistency of choosing when a company should take public stands, and distinguishes his view of the Ukraine invasion from his view of the Israel–Gaza conflict. He says the company’s general position is that chess should be inclusive across backgrounds and identities. These political judgments are his own.

A father of four, Allebest says his parenting has changed as he has learned that children respond differently to structure. His older children and younger children have posed different challenges. For one son, allowing more autonomy and letting him experience consequences worked better than increasing controls, he says.

Looking back, he would tell his younger self to create more positive interactions at home. Children encounter correction and disappointment elsewhere, so he wants home to provide a reserve of reassurance. He recalls moments when trying too hard to fix a child’s problem produced more negativity than allowing time and space.

In marriage, he recommends listening and acknowledging a partner’s feelings before trying to solve a problem. Validation alone does not resolve practical disagreements, he says, but it can make a later conversation productive. He also values being open about imperfections instead of trying to appear perpetually strong.

Stebbings worries that working less might make him mediocre. Allebest recognizes the impulse to stay busy, including his own tendency to clean, but suggests making room for reflection and self-acceptance. Working from home has allowed him to be present when his children leave and return, though he recognizes other jobs may involve harder trade-offs.

Allebest remembers becoming a millionaire after selling his second business at 28. Achievement makes him happy, he says, and money can signal it without being the goal itself. He has reconsidered how much structure every child needs and says health problems and death frighten him partly because he wants to see what happens next.

He credits his wife for seeing his better qualities and giving him room to grow. Asked for a dinner guest, he chooses Bernard Arnault because he is curious about brands, status and marketing. He says the things that matter most to him are relationships and time with people he loves.

Looking ten years ahead, Allebest is unsure whether he will still be running Chess.com. He expects the game to remain a durable source of interest even as new games and content proliferate. This is his hope and judgment about chess, not a guarantee of the company’s future.