Build Your SaaS Podcast

Justin: You had been building on the side for a long time before going full time. What did that path look like?

Tim: It goes back to college and then years of side projects while working full-time developer jobs. I built websites, then browser extensions, then products like Weather Extension and eventually the URL shortener extension that led into T.LY.

Justin: And you were doing that while raising three boys.

Tim: Yeah, which definitely changes the risk calculation. If I had been in my early twenties with no family, I probably would have tried going full time a lot sooner.

Justin: What were the guardrails that finally made you comfortable leaving your job?

Tim: My first target was matching my salary. Then I kept waiting until I had much more cushion, closer to double in practice, plus savings. I wanted enough margin that even if revenue dropped meaningfully, the family would still be okay.

Justin: How did you make side projects fit into regular life for that long?

Tim: Usually it meant working after the kids went to bed. A lot of those years were not just about building products, but also learning infrastructure, support, growth, and marketing in smaller steps over time.

Justin: T.LY has a huge free user base through the extension. Is conversion the main challenge now?

Tim: Yes. I have a lot of users already, and one of the biggest opportunities is helping more of the right ones convert from the free extension experience into the paid product.

Justin: What did going full time change emotionally?

Tim: There is definitely more pressure once the day job is gone. When the business becomes the only thing, every outage, support issue, or broken flow feels heavier.

Justin: We also spent time talking about stress after the jump.

Tim: Yeah, I said I expected six months of stability would make me feel better. You pointed out that some of that stress does fade, but usually only after the business proves itself over a longer period.

Justin: Since going full time, what has the actual work looked like?

Tim: A lot of balancing between features and marketing. The business already works, so now a big part of the job is turning growth knobs, improving awareness, and making sure more people discover T.LY.

Justin: You rank well in a very competitive search category. What has worked for SEO?

Tim: Some of it is structural because URL shorteners naturally accumulate backlinks, but I have also leaned into content, keyword research, related free tools, and reducing friction on the homepage so people can shorten links immediately.

Justin: We also talked about pricing, and I pushed back on the idea that affordable is always bad positioning.

Tim: That was helpful, because part of my strategy really has been to be the easier, more affordable option for people who do not need a big enterprise shortener.

Justin: You gave examples too, like weddings and QR-code use cases.

Tim: Exactly. Some customers just need a clean short link, a QR code, or a custom branded URL for a specific use case. Not all of them need a huge feature set, so simple pricing and low friction work well.

Justin: Where should people check out the product?

Tim: T.LY is the main place, and timleland.com has more about my work and projects.