Last week I sent all Yupdates customers the following email:
While subscriptions have grown, Yupdates hasn't seen the interest and growth rate needed to sustain a bootstrapped business. I tried many avenues to raise awareness and adjusted to great feedback (thank you). But the slow growth rate combined with personal financial surprises this year have made it unwise to proceed. Yupdates will shut down on December 30th, 2023. The plan: - Your two most recent subscription charges have been refunded. This may take up to 10 days to be reflected on your statement. - The service will be free for existing customers until December 30th, 2023. - It's not possible to create new subscriptions anymore (demo sessions remain OK). - All customer data will be deleted permanently on December 31st, 2023 except billing/Stripe records which need to be preserved for tax season and business records. It's been an incredible experience. And it's been a pleasure to work with you - thank you!
I'm unhappy about falling short of escape velocity. I'm unhappy about achieving just a small part of a much larger vision (including a significant open source piece). But I'm happy with how things turned out overall. I am proud of what I achieved technology-wise. It's meaningful to me how many customers were pleased or interested. I went well outside my comfort zone and learned a lot about business, product management, AWS, and Rust.
When I decided to start an independent software business, one of the driving factors was that I knew I would regret not doing it. I stick by that; it would've bugged me for the rest of my career.
But I do regret a few decisions. Last year, Yupdates got initial traction in my network and then word-of-mouth subscriptions by people I'd never met. Nice. But that set me off on a productization spree. Performance and availability were some of the main selling points, and it made sense at the time to make those things even better. I added multiple features that only a few people expressed interest in, including ones probably unnecessary for an initial offering, like MFA.
Waiting too long to push hard on growth is a familiar business trap, but I decided I had enough time (Hofstadter's law notwithstanding). Then, three separate personal financial surprises this year greatly upset that time calculation. I tried to accelerate growth (with little effect). I even thought about pivoting to solving a more urgent business problem. But my conservative side has taken over; it's time to call it.
It was sad to make the decision. But I quickly got excited about being on a team again. Ideas improve with diverse input, you share the ups and downs with people, and you can make a more significant impact. I've had the privilege of working on systems at a scale I would never see at a solo or small company. Many team and systems issues are very satisfying to solve, and I look forward to returning to that fold. When everything is flowing well, it can be a real pleasure. I enjoy being on high-functioning teams long-term and fixing processes/software to get teams into that wonderful zone: high productivity, high satisfaction, and minimal emergencies.
I've started talking about management opportunities with companies. This is the first time I've been able to openly search for a new job, which should be interesting. There are many exciting directions that could go in.