Tennis Solitaire is, admittedly, a quirky idea. But once it came to me, I felt like I should pursue it for a number of reasons.
In the fall of 2025 I quit my job selling software. It was a good job – I was the head of sales at a generative AI startup, but I was quite unhappy and knew it wasn't sustainable. I assumed that something new would be another sales job at another software company. I interviewed for several of those, but nothing clicked and nothing felt particularly exciting, especially when faced with a return of the perfunctory Zoom calls, endless 1:1's, awkward performance reviews. What did seem interesting was figuring out a path that was a bit more self-driven.
Rewinding a bit, two years ago I accidentally started playing tennis. Initially I just took over my daughter's lessons when she got hurt, but I quickly got sucked in and tennis encroached on, and then overtook, cycling as my primary hobby and source of exercise. I subscribed to the Tennis Channel when I needed to kill time in the airport waiting for a very delayed flight to Japan. I started following the sport, listening to the podcasts, etc…
So, when I started thinking about a new project I thought I'd try to make it tennis themed. This is not because of some super deep market or demographic analysis. I just wanted it to be related to something I'm naturally interested in as a way to help sustain my commitment. As it turns out, the demographics of tennis fans are great for advertising, but I discovered that later and it didn't really factor early on.
My general criteria for starting something new were:
- Minimal capital investment required
- Something I could build and run myself (at least in the beginning)
- Something I can manage from anywhere
- Something that would leave me with some valuable new skills, if nothing else
- And if it worked out, something that might have a chance of replacing my sales income
Some sort of ecommerce business seemed like the best bet to check all these boxes. I really love tea, and did a bunch of research on starting a specialty tea brand. I found the handful of potential wholesale partners who do most of the high end tea importing to the US, found a company that handles custom packing, evaluated the unit economics of warehousing and shipping with a fulfillment partner. Ultimately being so tethered to physical goods gave me pause, but in the process of researching the idea I started using claude.ai for analysis and that pushed me in a new direction.
During this time, a new family helper started working with us to help with the kids and household stuff. We were trying to find a free or very cheap time tracking app and everything I looked at was overly complicated for our needs or didn't do quite what we wanted. So I asked Claude for help building a simple time tracking web app I could share with our helper, which would track hours and send us summaries each week. I've been working in tech for nearly 20 years, but have zero coding or technical background, but with some AI help, along with some iteration and debugging, was able to get this up and running in an afternoon.
I also knew quite a bit about the games industry from a previous job. Somehow the combination of this background, the experience building this time tracker app, and all the ecommerce research I'd been doing got me thinking about building a game or a website, and trying to support it through ads or affiliate sales. I wasn't at all interested in doing another "best of" kind of site with review and product links, but thought maybe there would be a way to integrate ecommerce into a game. I would need some sort of theme or structure to inform the kinds of products that would be on the site, and decided it should be tennis because that's the information I'm already interested in consuming anyway.
Solitaire made sense for two main reasons. First, it's a fun way to kill a few minutes, and surprisingly easy to get focused for quite a bit longer than that. A lot (but certainly not all) of the free solitaire sites on the web aren't the most polished. Doing something with a nice enough look and good gameplay felt accessible to a solo operator with no web or game development experience. Second, Solitaire is public domain, so I wouldn't have to deal with complicated custom game play or IP issues; I could just start building (or at least trying).
But still, Tennis Solitaire seemed like an odd combination. A friend from some years back had started a sports-themed lifestyle coffee brand, which at first seemed like a strange idea. But over time it seemed to work, and I thought about why. As with web-based card games, coffee is basically a commodity (even nice coffee), so you need some way to establish brand identity to stand out. In the case of Tennis Solitaire, I think the tennis association is even more tightly integrated into the experience of playing, and Claude seemed to think the long tail keyword potential was strong.
So, I decided to start building. This site will be a live work in progress for the foreseeable future. The game is fun now, the tennis scoring works (or you can play regular Klondike in classic mode). I will be adding ads at some point because otherwise this really can't be self-sustaining. I may still find a way to integrate some affiliate sales, but I'll try do it in a genuinely helpful and un-annoying way. And if you have feedback or suggestions, I'd love to hear from you. Reach out via the Contact page.