Indie Bites - Taking on Bitly Bootstrapped

Host: Before T.LY, what kind of projects were you building?

Tim: I had been building software on the side for years. After college I worked as a developer and kept experimenting with products. One of the first that really took off was Weather Extension, which eventually reached a very large user base.

Host: Did Weather Extension ever look like the business you would go full time on?

Tim: Not really. It made money, but weather is a hard category because users expect it to be free. On top of that, the extension got hit with a wave of bad reviews at one point, which really slowed growth.

Host: So how did you end up in link shortening?

Tim: I was looking for more extension opportunities and built a tool to analyze the Chrome Web Store. I found a Google URL shortener extension with a huge user base, and around the same time Google was shutting down its own shortener. That looked like a clear opportunity.

Host: Was the extension the first step again?

Tim: Yes. I built the extension first, then later built the T.LY SaaS product behind it so I could control the service and add more advanced features.

Host: How did you position T.LY differently?

Tim: Initially it was very much about affordability. At the time some competitors charged dramatically more for custom domains, so I launched with a much lower price point. In hindsight I probably went too cheap, but it helped carve out a position in the market.

Host: And the product was still free for basic use?

Tim: Yes. People could create short links for free, especially through the extension. Paid plans unlocked the more advanced features like custom domains, smart URLs, and deeper analytics.

Host: Where did most of the early users come from?

Tim: The extension drove the initial wave. I already had a meaningful user base there, and that gave T.LY immediate exposure. From there I leaned into SEO, content, and related free tools like QR code generators.

Host: You eventually quit your job and went full time. What made you comfortable doing that?

Tim: I am naturally low risk, so I waited until the business was clearly supporting itself and I had savings in place. With a family and kids, I did not want to jump too early.

Host: You also made the point that “quit first, then figure it out” is riskier than people admit.

Tim: Definitely. I see people announce that day one of entrepreneurship starts the same day they quit, and it can work, but it is a risky route. It usually takes a long time to build something that reliably replaces a salary.

Host: What changed in your day once you were full time on T.LY?

Tim: I got more time for support, product work, and especially marketing. Awareness is still one of the biggest levers because people naturally think of Bitly or TinyURL first.

Host: We closed with a quick recommendation round.

Tim: My picks were Atomic Habits, The SaaS Playbook, the podcast My First Million, and Rob Walling as an indie hacker worth following.