As an entrepreneur, I’ve come to learn that building a product people love is rarely a straightforward process. One of the most difficult challenges for any startup is the “cold start problem”—the point when you launch a product into the world and there are no users, no engagement, and no clear signal of how to make it work at scale. When we first launched Chessable, we faced this very issue. However, by focusing on iterating for retention as our north star, we managed to not only overcome the cold start problem but to also create a product that people love and keep coming back to.
The Cold Start Problem: What Is It?
The cold start problem is simple in concept but complex in execution. When you’re launching a new product or platform, there are no users. Without users, you don’t have the necessary data or feedback to refine the product, and without refinement, it’s hard to attract more users. This creates a vicious cycle that can be fatal if not addressed quickly and effectively.
In our early days at Chessable, we were passionate about our product. We knew it had the potential to revolutionise chess learning by applying principles from cognitive science, like spaced repetition and active recall, to help people master chess more efficiently. But passion alone doesn’t fill your platform with users. The challenge was getting people to not only try Chessable but to come back, use it regularly, and spread the word.
Finding Product Market Fit: A Retention-First Approach
Andrew Chen talks a lot about the importance of focusing on retention before scaling. It’s not enough to bring users in if they don’t stick around. A common mistake many startups make is to drive growth too early, before the product has been refined. But if users don’t find value in your product, your growth efforts will be wasted. You will have a leaky bucket. I learned this firsthand way before Chessable during my Sharkius Games days. You could launch a game, and if you did not focus on retention, you could just ‘jump the shark’.
From the beginning for Chessable, it was decided that our primary metric wouldn’t be how many people signed up or visited the site. Instead, it would be how many people came back and used Chessable daily (later it was weekly). This focus on retention meant that we needed to iterate on the core product experience. Our early versions weren’t perfect, and to be honest, the first wave of users didn’t stay as well as we wanted them to. But instead of trying to immediately pour more users into the top of the funnel, we asked ourselves why retention was low. What was missing in the experience? What was confusing? What features were working, and which were not?
We dug into the data, talked to early users, and continually refined the product. We found that one of the biggest drivers of retention was the “learning loop”—the experience users had when they revisited the same material, practiced it again, and saw their progress through Chessable’s spaced repetition system, and had that “wow” or “aha” moment. That simple feeling of improvement and recall, was what kept users coming back.
We doubled down on that. We optimised the learning loop, improved our feedback systems, and added features that rewarded users for their effort and consistency, like streaks and progress tracking. By focusing on retention, we were able to turn our early adopters into dedicated users and evangelists of the product.
The Power of Retention in Driving Growth
Once we had solved the retention issue, everything else became easier. Our users loved Chessable because it helped them get better at chess in a tangible, measurable way. Word-of-mouth started to spread organically as our retained users became advocates. This is where Andrew Chen’s idea of the “network effect” comes into play. When your retained users start inviting others because they love the product, your growth becomes more sustainable.
By focusing on retention first, we created a flywheel effect. Retained users generated more engagement, which in turn attracted new users, and these new users would stick around because the product had been refined to meet their needs. Over time, this iterative approach allowed us to scale more effectively and efficiently.
The Value of Feedback Loops and Continuous Improvement
One thing we’ve never stopped doing at Chessable is iterating on feedback. We were constantly in conversation with our users, running experiments, and improving the product. This is another key lesson I’ve taken from Chen’s work: growth isn’t a single moment in time; it’s a continuous process of improvement and adaptation.
When you focus on retention and build meaningful feedback loops into your product, you can continuously refine the user experience. As we grew Chessable, we realised that every new feature had had to be looked at through this lens, otherwise, it wasn’t worth pursuing. Staying disciplined about what truly drives retention helped us avoid feature bloat and kept us focused on delivering real value.
Conclusion: How Chessable Tackled the Cold Start Problem
The cold start problem is one of the toughest challenges any startup will face, but I believe that focusing on retention from day one is the best way to overcome it. At Chessable, by iterating on the product experience and making sure our early users loved the platform, we built a foundation for long-term growth.
Retention is more than just a metric; it’s a signal that your product is delivering real value. Once you have that, everything else—growth, network effects, scaling—becomes more achievable. This is how we tackled the cold start problem at Chessable, and it’s a lesson I carry forward in everything I do. Today, I am working with the team at Chessiverse to achieve exactly this, and implementing these same lessons with the new start up I am co-founding called Alive Games.
