104 Scaling T.LY: From URL Shortener to Market Expansion

In this five-part podcast series, Chris Kiefer interviews Tim Leland, the founder of t.ly, the world's shortest URL shortener. They discuss Tim's background in software development and entrepreneurship, his experience scaling extensions to hundreds of thousands of users, and his decision to go full-time on t.ly. They touch on challenges in converting users to paid customers, the importance of clear and straightforward extensions, and concerns about free tools and privacy. They also talk about cross-promotion strategies, support and feature requests, and the reliance on podcasts and online communities for guidance. Tim shares his challenges in starting a new sport, the growth of t.ly, and the potential of expanding into the API and QR code market. They discuss affiliate marketing and its impact on credibility, and Tim recommends book and movie suggestions. The conversation concludes with Tim's contact information and Chris expressing interest in collaborating with entrepreneurs.