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“I sacrifice most of my personal life and identity to my work … my best clients do the same thing.”

This interview was made possible by our friends at DomainNameSales.com:



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Jimmy Flannigan, Site Street founder, arrived at The University of Texas at Austin in the fall of 1996. He quickly started learning how to build web-pages, creating a personal website and websites for various organizations and clubs right from his UT dorm room.

In 1997, he started offering his services to non-profit organizations around the country, from student and educational groups at Texas to a convent in Northern California. In 2001, Site Street moved into its current web hosting facility in Austin. Since that time, Site Street has continued to provide a unique combination of business-class reliable web hosting and personal one-on-one support. Site Street also expanded its service offerings to include search engine optimization, email marketing, and social media consulting, providing a full suite of website success services.

Site Street provides web design, development, hosting, search engine optimization, social media marketing, and consulting to small businesses and non-profit organizations.

Jimmy Flannagan, Site Street, Inc. - Owner

MO: What initially attracted you to website design?

Jimmy: My path to web design has a much nerdier origin story than most of my creative brethren. It started with learning how to program a Commodore 64 in elementary school to winning the Texas State Science Fair in Computer Science in high school. Once I got to the University, it was a natural evolution to start playing with web design. Sadly, I’m hopelessly color-blind so my first few attempts were painful, even by 1997 standards! That’s when my business really began to establish an identity that separated design from development, visual from strategic. 15 years later, I’ve maintained that belief, having never hired a graphic designer to work on-staff. I strongly believe that the best designers are terrible developers. And you never want a programmer creating your logo.

MO: How have you been able to maintain a small business that provides a traditionally large-business service?

Jimmy: It’s all about personal relationships. Even for my large competitors, clients develop a personal relationship with the sales person or their account manager. Any small business that competes like we do has to excel at developing relationships that last. It also helps that I sacrifice most of my personal life and identity to my work. It’s not even a joke… my best clients do the same thing with their businesses and that shared understanding makes for a very strong bond.

MO: How did becoming a host provider change the company?

Jimmy: We started hosting so early in our evolution; it’s hard to say that the move in 2001 dramatically changed the company. In fact, we were “hosting” websites from the very beginning. One of the first organizations I worked with had their website hosted on a server in my dorm room; a dorm room that I had to leave over the summer. That left their website offline from June to August. It was definitely something that would never be acceptable now! I tried reselling hosting services for a couple months but after one hosting outage I was left feeling helpless and having to answer calls from angry clients. I decided then that if I was going to have to deal with the repercussions of downtime, I should at least have the control over its resolution.

MO: How has Site Street evolved since you first started out in 2001?

Jimmy: The company has evolved with me in a very personal way. The structure itself is still focused around the personal connection I have with customers, but our product offering has expanded as my own understanding has grown. I spent 5 years working in the dot-com world post-2001, also getting my MBA in e-Business. Those experiences, plus the rise of search engine optimization and social media, have dramatically shifted our approach from tactical implementation to more strategic planning. I often find myself straddling the worlds of operations, marketing, customer service, and accounting during the course of a project. In 2001, I was building websites. In 2012, I’m developing comprehensive strategies for success combining web, email, SEO, and social media.

MO: Learning from mistakes is critical for entrepreneurs. Can you share some lessons learned from your past or how you would have approached things differently?

Jimmy: The biggest mistake I made in my business, and a mistake I’m still paying for, is making the wrong decisions about hiring and firing personnel. Hiring one or two people doesn’t sound like a big deal except when it represents doubling your entire staff! Just like I do with my customers, I quickly established friendships with my staff. But those relationships made it nearly impossible to admit that I had hired the wrong person or that they needed to go. I hired people too quickly and kept them longer than was necessary. I’m still suffering the consequences of those poor decisions from more than 5 years ago.

MO: What professional accomplishment are you most proud of so far?

Jimmy: Does survival count as an accomplishment? I’ve seen so many in my industry come and go over the past 15 years. That I’m still here, with some of the same customers from the very beginning, is something about which I’m more amazed than proud. And while I couldn’t point to a single moment, my work with the Austin Gay and Lesbian Chamber of Commerce on a local and national level gives me great pride. I get a real sense of personal accomplishment helping grow the economy for LGBT-supportive businesses. With all of the political machinations over gay rights, the economic component of that struggle is one that benefits everyone, including our straight allies. And even though I’ve sacrificed my own business at times to further that goal, I know that the path to prosperity for all of us starts from a place of inclusion and equality. It’s a battle I’m proud to fight.

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