Bootstrapping on the Side for 8 Years

Hosts: Today we’re talking with Tim Leland about bootstrapping side projects for years while still working a full-time job. His two main products are Weather Extension and T.LY.

Tim: I started out doing website work for local businesses around 2012. That eventually pushed me toward products, because building something once and selling it many times is a much better long-term model than custom work for every client.

Hosts: Has it always been a side project path for you?

Tim: Yes. I have kept a full-time job the whole time. Even with projects that are doing well, I have treated them as nights-and-weekends businesses.

Hosts: How do you keep that manageable?

Tim: I try to build products that are low-support and easy to understand. Weather Extension mostly runs on its own outside of updates. T.LY is also simple on the surface, which helps. If people can figure the product out without a lot of hand-holding, it is much more realistic to run alongside a full-time job and family life.

Hosts: Have you ever built something that was too sales-heavy for that model?

Tim: Definitely. I once built a menu-management system for restaurants. Technically it worked, but the only way to make it succeed would have been direct sales to restaurants. I quickly realized I did not want that business badly enough to spend my time cold-calling or doing in-person sales, so I dropped it.

Tim: That is one reason I like browser extensions. There is a built-in store, people already understand how to install them, and discovery is easier than with a totally independent product.

Hosts: What are the downsides of building on top of the Chrome Web Store?

Tim: You are relying on a platform you do not control. Chrome has become stricter about permissions and reviews, which is good for security, but it does add friction. Updates that used to go out quickly can now take longer. And if platform rules change, you have to adapt.

Tim: Manifest changes are a good example. When Chrome moved toward a new extension manifest, that created both work and opportunity. Old unmaintained extensions with lots of users were suddenly vulnerable to being disabled. That opened the door for better replacements.

Hosts: Is that what happened with the T.LY extension?

Tim: Pretty much. I built a script to identify extensions with lots of users that had not been maintained in a while. Around the time Google announced it was shutting down its URL shortener, I saw a Google URL shortener extension with a large user base. That looked like a clear opportunity, so I built a new version that supported multiple providers and later my own service.

Tim: Once Google shut its service down and that extension stopped working, users needed an alternative. That is where a lot of the growth came from.

Hosts: How do people mainly find your products now?

Tim: Cross-promotion helps a lot. When someone installs one of my extensions, I often point them to the others. I also write about them on my blog, and the URL shortener extension ranks well both in Google search and in the Chrome Web Store for relevant searches.

Hosts: What kind of business has that turned into?

Tim: The T.LY extension crossed roughly 400,000 users, and the paid product has a little over 600 paying customers with more than $4,500 in monthly revenue. Pricing starts at $5 per month and scales up based on features and usage.

Hosts: What pushes someone from free to paid?

Tim: Free works for basic shortening, but paid plans unlock custom domains, smart URLs, analytics, password-protected links, expiring links, and higher usage limits. The heavy users are the ones who convert: people sending lots of links, using SMS, or needing branded links for business use.

Hosts: How do you keep infrastructure costs under control with that many users?

Tim: Extensions themselves do not create much load because the code runs in the browser. The real cost comes from API calls and redirects. That means caching matters a lot. I also rely heavily on background jobs and have scaled servers and databases as the service grew.

Hosts: What about abuse? That seems like a major problem for URL shorteners.

Tim: It is. Early on, I did not fully appreciate how quickly bad actors would use the service. My hosting provider shut the servers down after malicious URLs started flowing through it. I spent months building abuse detection and review systems. Honestly, I have probably spent more time on malicious-link prevention than on the actual shortening logic.

Hosts: And Weather Extension is still active too?

Tim: Yes. It is more mature and needs less active development. The challenge with weather is that users expect it to be free. The way I have handled that is with a one-time pro upgrade that adds features and helps cover the API costs from constant background weather updates.

Tim: One painful episode there was a wave of fake negative reviews. It dragged the rating down significantly and affected growth. That is the dark side of building on someone else’s platform: a broken review system can hurt you even if the product itself is solid.

Hosts: What have you learned from doing this for so long on the side?

Tim: Time matters more than perfection. If I only have an hour in a night, I try to ship something useful rather than obsess over ideal code. I still care about quality, but momentum is important. I also think persistence matters. I have been at this for years, and most of these projects grew slowly rather than exploding overnight.

Tim: The other big lesson is to build things you personally care about. Weather Extension solved a problem I had. T.LY came from a real need I had seen at work. That makes it easier to stay motivated over a long stretch.

Hosts: Do you want to go full time on your own projects eventually?

Tim: Possibly. But with a family and three kids, that is a bigger decision. For now I like the stability of the day job and the freedom to build carefully on the side.

Hosts: Final thought?

Tim: One of the coolest moments was waking up and seeing that someone had paid for one of my products while I was asleep. That feeling of passive income from something you built yourself is hard to beat. It keeps me looking for products that are simple, useful, and can keep earning without constant attention.

Hosts: Where can people find you?

Tim: You can find my projects at T.LY and Weather Extension, and you can find more of my work on timleland.com.