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Norbauer Inc illustration by Jessica Hische

At no point in my life until I stumbled into founding my own companies did I ever desire to be a man of business—and even then I remained ambivalent. But at some point early on in life I learned that it's irksome to work for people who are dumber than you are, and that doing things yourself is frequently the only way to make things happen in the world. Thus the idea of entrepreneurship began to have an appeal.

I suppose also that, having originally come coming from an academic background, I was simply insecure about and intimidated by the supposed "real world" of work and money-making, and I wanted to prove to myself that it was a domain in which I could be productive—whether or not that was something I inherently valued very much.

At any rate, I started three companies, ran them until I stopped learning new things from the work, and then sold each one. Though they were all in varying ways sources of frustration and disappointment, I'll concede that they were all far more successful than I could ever have hoped or imagined at the outset of each enterprise, and from each of them I was able to learn about and do things that would otherwise never have been possible.

Lovetastic / Scene404

Lovetastic illustration

Acquired by: OKCupid (now Match.com)

Screen captures and selected press clippings.

In many ways, I'm probably most proud of Lovetastic, if for no other reason than that it was a project it affected more people than anything else I've ever done (or perhaps am likely ever to do). It also happens to be where I met my husband Alan.

The idea, which I had around 2004, was simple: to build an online community for guys who like guys but who feel like we don't quite fit in with mainstream gay culture. Originally, I called the site Scene404 (a nerdy reference to the "gay scene" and server error code returned when you try to go to a location that doesn't exist). I had just come back from an exciting year working in the British Parliament and found myself back in the ivory tower, very much missing feeling connected to the real world. So after a few weeks I cashed in my academic chips (which actually turn out to be worthless), and set off on my own to build a web start-up. The only trouble was that I had never built a web application in my life, or practically any production-ready software for that matter—and I had no idea how to run a business. So I sat down on Day 1, opened up a book on SQL and went to town, endeavoring to study software engineering as assiduously as I had my scholarly subjects. After about six solitary months of (mostly nocturnal) 14-hour days behind my Linux terminal, Scene404 went live.

Our membership grew steadily thanks to early positive feedback on sites like GayGeeks.org and due to a series of early podcasts I did interviewing interesting stereotype-busting gay men. After running a few ads in The Harvard Gay and Lesbian Review, I managed to get some early attention from a small but influential (and thoughtful) crowd of gay men. Within a few months, I had been approached for investment in the company. I eventually accepted an offer to sell a portion of my shares in order to raise funds to undertake a major promotion and advertising campaign in hopes of launching the project into national attention.

In this manner I went from coding a speculative website from my father's house in an obscure part of West Virginia (not that there are non-obscure parts), within a year I suddenly found myself running a company with an office in Manhattan, hiring a fancy Madison Avenue PR firm that also represented the likes of BMW, Activision, Disney, and Bloomberg, doing interviews for major national newspapers, and celebrating our deal closing at the Four Seasons (the restaurant in the Seagrams Building, not the hotel)—heady stuff for a 24-year-old from the Appalachian sticks. For me, the excitement of this era is perfectly encapsulated in this nervous interview I did with Leo Laporte (a journalist, formerly of TechTV, and hero of mine from adolescence.)

Part of the investment in the company involved a major rebranding and trademarking effort to "Lovetastic," and it gave me resources to oversee a comprehensive visual redesign and a ground-up rewrite of the software, along with an overhaul of our server infrastructure. Being able to hire a team of developers made it possible to do all sorts of inte