SaaS Pirates Podcast

Host: Today we’re talking with Tim Leland about growing T.LY to roughly $5,000 MRR and the growth tactics behind it.

Host: Give us the short version first. What is T.LY?

Tim: T.LY is a URL shortener with some extra features on top. People can create short links for free, and paid plans unlock things like custom domains, analytics, API access, and smart links.

Host: How did the business start?

Tim: It goes back to browser extensions. I built Weather Extension in 2015, then later started studying the Chrome Web Store to find other opportunities. I noticed a Google URL shortener extension with a large user base right when Google was shutting down its own service. That looked like a perfect opening, so I built a competing extension.

Tim: Once that extension gained traction, it made sense to build my own shortening service behind it. That became T.LY. So the sequence was: extension first, product second.

Host: That sounds like a strong distribution strategy. How did you get the first users?

Tim: The extension store did a lot of the early work. I also cross-promoted from my other extensions, especially Weather Extension. Once I connected the T.LY service to the URL shortener extension, I had users on day one because the extension already had traffic.

Host: What was hardest about getting to product-market fit?

Tim: Figuring out what people would actually pay for. Most users think a URL shortener should be free, so the product needed premium features with clear business value. API access, smart links, and custom domains were the big ones. Those features matter to teams sending SMS, running campaigns, or needing branded links.

Host: What has driven growth the most?

Tim: Free tools. If I had to pick one thing, it would be building free entry points that attract the right users. The browser extension is one. A QR code generator is another. Those tools bring people in, and some percentage of them later upgrade when they need more control.

Tim: T.LY also has a bit of a built-in viral loop because every time someone shares a T.LY link, they are exposing more people to the product.

Host: So what was revenue at the time?

Tim: About $4,500 MRR, with good growth and plenty of room to improve conversion from extension users to paid subscribers.

Host: What is the biggest founder lesson so far?

Tim: Stay focused. I have built a lot of projects over the years, and it is easy to lose momentum by chasing the next idea. With T.LY I have been more deliberate about sticking with one thing and continuing to improve it instead of jumping away too early.

Host: If you were starting a SaaS today, what would you do first?

Tim: I would seriously look at building inside an existing marketplace. App stores and browser extension stores come with built-in distribution. That can dramatically reduce the amount of marketing you need to do up front.

Host: We also closed with a quick personal round: you rely on simple tools like Apple Notes and Reminders, you like Cloudflare, you spend a lot of time on YouTube and Twitter, and Atomic Habits was your book recommendation for builders.

Tim: Yes. I also mentioned Nathan Barry as someone I admire and Peter Levels as someone worth following. Both are good examples of focused independent builders.

Host: Where should people go if they want to learn more?

Tim: T.LY is the best place if you want to create short URLs, and timleland.com is where I write about my projects and technical work.