Tim Leland Grew the T.LY Subscription Business from a Free Extension

Turning a URL Shortening Service from a Side Project into a Full-Time Business

Tim Leland builds the URL shortening service T.LY and a number of browser extensions, and in 2023 he turned a side project he had run for more than ten years into a full-time business. In a market where Bitly and TinyURL were already established, he gathered users with free extensions and sold management features as a subscription to customers who used links in their work. It is a case of taking a familiar feature and attaching a customer acquisition path and a recurring revenue structure to turn it into an independent business.

From Client Work to Browser Extensions

After finishing university in 2012, Leland worked as a developer and started a side business building websites for local businesses. The plan was to charge $400 to build a site and $20 a month for hosting. But after building five sites, he realized that making each one from scratch for a new customer required too much work to earn enough income. He then shifted his attention toward selling the same product to many people.

Read Later, which he built in 2014, was a Chrome extension that saved pages to read later, and the development experience he gained there led to the next product. In 2015 he released Weather Extension, which let people check the weather in the browser. Instead of reaching for a phone or opening a weather site while using the computer, a user could click the icon to see the temperature and forecast. The product was covered by Lifehacker and grew into an extension used by hundreds of thousands of people.

Weather Extension offered its basic features for free. When some users voluntarily donated, Leland judged there was demand for paid features, and he sold extras such as weather for multiple locations and alerts. Compared with the large user base, the income stayed at side-project level, but he gained experience distributing an extension and turning user requests into paid offerings.

Not every product he built grew. GrubPress, from 2017, was a tool for managing a restaurant's online menu, and he applied it to a few sites he actually managed. But restaurant owners did not actively search for a tool like this, and growing the business would have required selling directly. Looking for a product he could run alongside a job, he shut the project down.

When looking for the next idea, he first built a tool that collected and scanned extensions in the Chrome Web Store. It was an attempt to find products that many people already used but whose developers did not maintain well enough. In the process he found a popular extension that used Google URL Shortener, and combined with Google's plan to end the service, he spotted an opening for a replacement.

In March 2018 Google announced the phased winding down of goo.gl. The link management console and API it had offered to existing users were also scheduled to end on March 30, 2019. The notice said that links already created would keep working, but people who wanted to keep generating new short links had to look for another service.

Leland first built an extension that connected to several shortening services. The early version called services such as Bitly and TinyURL, and he had no plan yet to run his own shortening server. With one button a user could shorten the address of the current page and copy the result to the clipboard. Already used to building extensions, he said he finished the first version as a weekend project.

He used his existing products for the initial distribution. He introduced the new extension on Weather Extension's installation guide screen and on his personal blog, and in the web store he used the name "URL Shortener" to match what users searched for. After Google's service ended, the extension's users grew quickly from about 10,000 to 60,000. Having the replacement in place before the search demand appeared paid off.

As users grew, the problem of depending on outside services became clear. When another shortening service's domain stopped working or its certificate expired, users contacted Leland, the developer of the extension they had installed. To manage reliability himself, he built his own shortening service and connected T.LY, released in 2019, as the extension's default service. Thanks to the users he had already gathered, T.LY saw real usage from the moment it launched.

From Free Users to Paying Customers

T.LY's free features handled the basic task of creating short links. The paid subscription included creating links on a domain the customer owned, analyzing click statistics, and generating links by API from other programs. The structure was that someone who shortened an address now and then used it for free, while customers who used links continuously in their work paid for the management features.

The business demand was concrete. A company doing text-message marketing had to generate short addresses in large numbers automatically, and a business wanting to show its brand wanted to use its own domain. Linking a QR code on printed material to a short link let them change the final destination page and measure traffic without reprinting. For these customers, T.LY was a management tool they kept using after creating and distributing the link.

In a SaaS Pirates interview published in June 2022, Leland stated directly that monthly recurring revenue at the time was about $4,500. The show's title and description put it at roughly $5,000. In the same interview he named increasing the share of free extension users who buy paid features as his main growth task.

The paid plans described in a June 2023 interview were $5, $20, and $50 a month. Leland offered a cheap entry plan so that customers who did not need many links or complex features could still buy. At the time the free extension had about 450,000 users, a number that must be separated from the paid subscriber count. He chose to convert part of the large free user base into low-burden subscriptions.

Building the Conditions to Leave the Job First

While running the products, Leland kept working as a full-time developer for a long time. He developed for a few hours after his children fell asleep, and through building the products he also learned server operations, customer support, and marketing. The initial goal was to cover the cost of lunch or coffee and the server with product income. From that small goal he grew the business over several years.

When moving to full-time work he was raising three sons, so he checked the stability of the income first. He had thought he would quit once he earned as much as his job's salary, but he said he actually waited until he was earning nearly twice that amount. The family lived mainly on his job salary and saved or invested the side income, building a financial cushion as well. In the interview published in June 2023, he said he had switched to full-time about a month earlier.

After switching to full-time, he took on customer support, feature development, and marketing himself. Many people already used the product, but there was still work left in making T.LY come to mind when new customers looked for a URL shortening service. He divided his time between adding features and raising brand awareness, and focused more on improving search traffic and signup conversion.

Running a Small Feature as a Long-Lasting Business

As the business grew, operating problems grew too. In a write-up of his 2025 Laravel News appearance, Leland named handling large-scale traffic, spam and malicious links, and bot traffic and DDoS attacks as his main challenges. Even after implementing the address-shortening feature, he had to block abuse and keep legitimate links working. Running a product with many free users on his own meant carrying that burden as well.

Running both the extension and the web service also served to split the distribution paths. Leland valued the fact that even if the extension could not be distributed through the Chrome Web Store, the T.LY web service itself would still be usable. While acquiring users through the extension, he expanded the business so that product use and payment could also be handled on the website.

In 2025 he made developing free web tools more systematic as a way to increase search traffic. He built tools such as one that reveals the destination of a short link, a UTM address generator for ad tracking, and a bulk QR code generator, and provided a page matched to the search demand for each. More comfortable with software development than writing, he also set up a common development framework that let him add new tools quickly. Some of the visitors who came through these tools went on to look at T.LY's core service, creating new customer touchpoints.

In an update published in May 2026, Leland said that URLs and QR codes created with T.LY had passed 60 million in total and that overall users had passed one million. Beyond short links, the product came to include QR codes, OneLinks for gathering several links on one page, team features, and customer domains and an API. What began as a service shortening addresses behind an extension had expanded into a platform for creating, distributing, and managing links.

What became the foundation of the independent business at T.LY was a structure that brought customers over from an existing product and handled paying customers' work repeatedly. Leland grew it alongside his job, then moved to full-time once the income to support his household and a financial cushion were in place. Step by step, he solved customer acquisition, payment, and operations until one small feature became a job.