In-Depth: Pursuit Of Purpose Scaling Tly

I joined Chris Kiefer on The Pursuit of Purpose to talk about building T.LY, leaving my job, how browser extensions turned into a SaaS product, and what I was learning about growth, pricing, and distribution along the way.

In this episode, Chris and I talk about leaving my job, growing T.LY from a browser extension into a SaaS product, testing pricing and distribution, and the practical lessons from trying to scale the business.

Transcript

Transcript generated from the episode audio and lightly cleaned for readability.

Chris Kiefer: You had already built a meaningful business before going full time. Give listeners the short version of your background.

Tim: I studied computer science, worked as a software developer, and kept building side projects on nights and weekends. Over time that shifted from websites for local businesses into products, especially browser extensions.

Chris Kiefer: Was Weather Extension the first big one?

Tim: Yes. It grew into a large product and taught me what it looks like to support hundreds of thousands of users. It still exists, but it also taught me that weather is hard to monetize because most people expect it to be free.

Chris Kiefer: So how did T.LY happen?

Tim: A company I worked for needed a URL shortener internally, so I built one and saw why businesses actually care about the problem. Later Google announced it was shutting down its own shortener, and I noticed there was a huge extension user base that would need an alternative. I built the extension first, then the SaaS product behind it.

Chris Kiefer: At what point did you know this could become your full-time thing?

Tim: I had wanted to work for myself for a long time, but with a family I was conservative. I waited until revenue was at least around my salary, then really closer to double before making the jump. I also tried to save side-project income for years instead of immediately depending on it.

Chris Kiefer: What made you confident enough to finally commit?

Tim: I felt like I had enough margin that even if revenue dropped, I would still be okay. That was the key guardrail for me.

Chris Kiefer: What has driven growth the most?

Tim: The extension ecosystem helped a lot early on, and after that it became a combination of SEO, free tools, and steady product improvements. I spend a lot of time building content and utilities around short links, QR codes, and related workflows so more people discover T.LY naturally.

Chris Kiefer: You also mentioned that competitors sometimes help you without meaning to.

Tim: Definitely. Some of the larger players have added extra friction, changed pricing, or made basic shortening less convenient. When somebody just wants to create a short link quickly, that opens the door for a simpler product like mine.

Chris Kiefer: So what is your positioning today?

Tim: I am trying to be the simpler, more affordable option. A lot of users do not need an enterprise stack. They want custom domains, analytics, smart redirects, API access, and QR codes without a bloated setup or enterprise pricing.

Chris Kiefer: We spent some time talking about founder bottlenecks too.

Tim: Yeah, that is real. I have done almost everything myself for a long time, and one of the next growth steps is probably getting more help, especially on the marketing side.

Chris Kiefer: We also talked about QR codes as a good example of why short links still matter.

Tim: Right. If a QR code points to a short link, I can change the destination later without reprinting anything, and I can also track scans. That flexibility is a big reason the product is still useful even in a crowded market.