Zach Ocean
January 8, 2024

How could drive growth, revenue, and retention with AI-powered initiatives

Some tactical suggestions for growth strategies powered by cutting edge generative AI. is an incredible growth success story. The nearly 20-year-old company grew slowly, then all at once to its position today as the dominant online chess platform.—which has never raised money from venture capitalists—now has 400 employees, 100 million users, and over $100 million in annual revenue. (You can read a deeper dive on the company’s history here.)

Part of the story of’s success is timing. When the COVID-19 pandemic hit in 2020, millions of people adopted new online-only hobbies and flocked to streaming platforms like Twitch. Chess live-streaming took off on Twitch, with trash-talking grandmasters (the top rank in the hierarchy of official chess titles) attracting legions of followers. The hit Netflix Show The Queen’s Gambit didn’t hurt things either.

But the other part of’s success is tremendous focus on growth and innovation, despite their core offering of a game that hasn’t changed since the middle ages. Competitors like the non-profit Lichess have kept functionality and costs lean and mean. In comparison, has experimented with novel growth strategies like developing an ensemble of fun bot opponents that you can chat with while you play. (Mittens, a deranged chess-playing, smack-talking kitten, is the most notable of the lot and was a huge hit on social media.)’s positioning compared to more spartan competitors like Lichess means that they absolutely must continue to pursue more ambitious and innovative product and growth strategies. Fortunately, thanks to the tailwinds of tremendous technical advances in generative AI, it’s a great time to do just that.

Here are a few tactics could continue their ambitious strategy:

  1. Drive growth with shareable recaps, doubling down on the traction they already have in online short form video.
  2. Drive retention with explainable recommendations
  3. Drive revenue and grow the footprint of the existing online store with AI-powered print-on-demand products.

Let’s dig into the details of each of these strategies.

Drive growth with shareable recaps, doubling down on the traction they already have in online short form video. has benefited tremendously from the popularity of short-form video platforms. During the COVID-19 live streaming boom, grandmasters live-streaming on Twitch attracted huge followings. But live-streaming content doesn’t disappear when the stream ends—instead, that video content gets sliced and diced into short-form clips that are published to Tiktok, YouTube Shorts, and Instagram Reels. Top chess creators now have significant followings on those platforms in addition to Twitch—GM Hikaru Nakamura, for example, has a following of over 2 million on YouTube and 600k on Tiktok.

To double down on the lift they’re already getting from top creators, could launch shareable recaps: auto-generated video recaps of dramatic, entertaining or critical moments in user’s games, designed to be shared  as user-generated content on social media.

By layering recaps generated by AI voices alongside chess game animations, they could build entertaining branded content that serves as organic marketing for the site.

As an example, you could imagine turning a game into a rap video made with Uberduck: could even incorporate the work they’ve done with characters like Mittens, giving them AI voices and turning them into narrators with distinct personalities. They could use LLM prompting combined with the analysis from their chess engine to ensure that each character generated analysis which was both accurate and consistent with that character’s designed personality.

Drive retention with explainable recommendations

One of’s best social features is opponent recommendations. Based on your game history, they automatically recommend opponents who are a good match.

Recommendations are a great tool to increase retention—particularly if delivered in a push format like email marketing or push notifications.

But recommendations could be even more powerful if they were delivered in natural language in a consistent voice—like how a friend recommends that you meet another one of their friends. Once again, has already laid the groundwork for a great implementation with there existing character features. Suppose Mittens sent you an email after she trounced you in a Blitz match: “Hey - Mittens here. You should really play against my friend X, your Queen’s Gambit would be a great match for her King’s Indian and you’ve both been improving your ratings at about the same pace over the last couple months.”

Drive revenue and grow the footprint of the existing online store with AI powered print on demand products. has two online stores already—a traditional chess supplies store and a merch store (the merch store is the cool cousin—they sell patterned t-shirts and Mittens plushies).

Chess gear is a lot of fun. When I was a kid, I loved buying novelty chess sets. One of my favorites was a Yankees-versus-Mets themed set that had catchers as rooks, infielders as pawns, and pitchers as the king. (I was pleased to see that this set is still available on Ebay.)

The Yankees-Mets chess set I bought felt special to me because it was personalized to my interests, and personalization turns ordinary products into special gifts.

Thanks to the data that has on their users and the development of print-on-demand and text-to-image technologies, they have a unique opportunity to sell highly personalized products. For example, they could commemorate the moment that a user first passes a rating of 1500 by making a custom shirt design around the final board position of that special game. Or even remake that Yankees-Mets chess set with custom resin figurines generated by end-users using a text-to-image product.

January 8, 2024