Riding Solo: Breaking Through as a Solopreneur with Tim Leland

Nikolas: You built T.LY by yourself in a really competitive category. Why go after URL shortening at all?

Tim: I kind of stumbled into it through browser extensions. I saw that Google was shutting down its URL shortener and noticed there was a huge Chrome extension audience that would soon need an alternative. That looked like a good opening.

Nikolas: So the extension came first, not the SaaS?

Tim: Exactly. At first I only wanted to build an extension that could create short links through other providers like Bitly and TinyURL. I was not originally planning to build my own service behind it.

Nikolas: How long did version one take?

Tim: Not long. I had already built a lot of Chrome extensions, so the first version was basically a weekend project.

Nikolas: How did it find traction?

Tim: A few things mattered. The extension does exactly what the name promises, it is simple, it requires almost no permissions, and it was easy to try immediately after install. I also cross-promoted from other extensions I already had, especially Weather Extension.

Nikolas: What did that cross-promotion look like?

Tim: Usually an install or confirmation page would point users toward my other extensions. My personal site also helped because it listed all of my projects and gave them more search visibility.

Nikolas: Was Chrome Web Store optimization a major factor too?

Tim: Definitely. Screenshots, copy, and overall clarity help, but the biggest thing was probably naming. I used the plain name “URL Shortener,” which lines up almost perfectly with what people search for.

Nikolas: Chrome extensions can be hard to monetize. How do you handle that?

Tim: The extension is genuinely free for simple use. If somebody wants more advanced features like custom domains, custom back-halves, expirations, analytics, or account-level management, that is where the paid product comes in.

Nikolas: So your free product is useful by itself, and the paid product is for heavier users.

Tim: Exactly. I want the free version to feel real, not like fake free.

Nikolas: How do you split time between building and marketing?

Tim: I usually work on whichever thing seems highest leverage at the moment. Lately that has included more “engineering as marketing” work, like building free tools that fit naturally around short links and bring in search traffic.

Nikolas: What does success look like from here?

Tim: The extension goal is one million users, and the broader goal is for T.LY to become one of the shorteners people naturally think about alongside the older incumbents.

Nikolas: What gives you an edge against those incumbents?

Tim: The domain itself helps because the links are extremely short, and I think there is still room for a product that is simpler and more affordable than the bigger players.

Nikolas: We also talked about the next stage probably being onboarding, conversion, and maybe help with marketing.

Tim: Yeah, that feels accurate. Building is still important, but some of the next growth likely comes from awareness, conversion improvements, and getting more help on the growth side.

Nikolas: One of the other strong use cases you mentioned was QR codes.

Tim: Right. If a QR code points to a short link, I can update the destination later and still keep analytics on scans. That is really useful for printed campaigns and anything physical.