Riding Solo: Breaking Through as a Solopreneur with Tim Leland (Founder of T.ly)

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In our latest podcast episode, we delve into the world of digital innovation with an intriguing conversation featuring Tim Leland, the mastermind behind T.ly, a trailblazing link shortener service. With over 400,000 users on the Chrome Store, Tim’s journey from conception to scaling T.ly is nothing short of inspiring.

This episode is a goldmine for anyone interested in tech entrepreneurship, filled with practical insights and the real-life experiences of a solo founder.

“Sometimes the best opportunities are hidden in plain sight,” says Tim, reflecting on his initial foray into the competitive world of digital tools.

Who is Tim Leland?

Meet Tim Leland, founder of T.ly, a service that has simplified digital interactions for hundreds of thousands of users. Tim’s background in software development and his keen eye for market opportunities have established him as a prominent figure in the tech world.

His company, T.ly, isn’t just another link shortener; it’s what one can achieve with the right mix of technical expertise, market awareness, and relentless drive. In an industry where staying ahead means constant innovation, Tim has managed to not only stay relevant but also become a trendsetter.

Follow Tim on LinkedIn and Twitter to learn more about his entrepreneurial journey.

Summary of the podcast

The Genesis of T.ly

Timestamp: [00:00 – 01:11]

Tim Leland, during his pursuit of what to work on next, identified an opportunity in the Chrome extension space with the impending shutdown of the Google URL shortener. This led to the birth of T.ly, initially as a Chrome extension interfacing with existing URL shorteners. His venture into this crowded market was driven by recognizing a gap and a user base in need due to Google’s decision.

Building and Scaling the Extension

Timestamp: [01:52 – 03:43]

Leland discusses the initial development of T.ly, highlighting it as a swift process owing to his experience with Chrome extensions. He emphasizes the importance of building a simple, permission-limited, and functional product that aligns with user expectations. His strategic use of other popular extensions for cross-promotion and a focus on SEO greatly contributed to T.ly’s initial and ongoing user acquisition.

Monetization Strategies

Timestamp: [07:05 – 08:14]

Monetizing a Chrome extension poses unique challenges. Leland describes T.ly’s freemium model, where basic features are free, and advanced features like custom domains and detailed tracking are part of a paid subscription. This model caters to a diverse range of users, from individual creators to small businesses.

User Demographics and Marketing

Timestamp: [08:49 – 09:51]

Understanding the user base is key for any service. Leland notes the diversity of T.ly’s users, ranging from teachers to marketers, highlighting the universal need for URL shortening services. His marketing efforts are geared towards raising brand awareness and competing with larger, more established players in the market.

Transitioning to Full-time

Timestamp: [10:25 – 12:08]

A significant milestone for Leland was transitioning T.ly from a side project to a full-time endeavor. This decision was driven by the desire to accelerate growth and development, leveraging his decade-long experience in building tools and applications.

Solo Entrepreneurship and Future Vision

Timestamp: [12:39 – 17:56]

As a solo entrepreneur, Leland juggles between customer support, feature development, and marketing. He emphasizes the importance of balancing these roles and constantly seeking user feedback for improvement. The long-term vision for T.ly is to become one of the top URL shorteners, competing with giants like Bitly and TinyURL.


This episode with Tim Leland is a deep dive into the ethos of tech entrepreneurship and innovation. It’s a tale of identifying gaps in the market, the art of product development, and the hustle of scaling a business.

Tim’s journey with T.ly is a masterclass in navigating the competitive digital landscape, offering listeners valuable takeaways on developing user-centric products, strategic marketing, and the power of perseverance. 

We highly recommend tuning into the full episode for an in-depth exploration of Tim’s journey and T.ly’s growth story.

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