Running a high profile and controversial site as anonymous is a great experience. You choose what you do, when you work, and who you respond to, all while your email inbox is empty. There is complete freedom. BUT, there are drawbacks, too. You don’t have anyone to discuss ideas with. You only hear anecdotal stories about the quality of work. You can’t go on the offensive or defensive to make a point. You make embarrassing slip ups.
Anonymity was a key ingredient to the success of TheFunded.com, which formally launched to the public (versus a small group of insiders) on March 14th, 2007. So, as the creator of the site, I chose to embody the principle and be anonymous. Since there has been some speculation about this, I would have been very happy to remain anonymous indefinitely.
When TheFunded.com was founded, I was raising capital for Game Trust and considering merger interest. The worst case scenario would have been to have my investors calling me about reviews on TheFunded.com versus signing necessary deal paperwork. Ironically, most of my venture investors asked me to review them on TheFunded.com anyway, but there was no pressure to delete reviews in exchange for signatures, which I feared would happen.
So, why did I come out? It so happened that right around the time that Game Trust sold, which closed on October 1st, 2007, Wired Magazine approached me (anonymously, of course) about doing a story. They stated that I might get the cover only if I revealed my identity to them exclusively. Meanwhile, I was making stupid mistakes as I worked 20 hours per day on the Game Trust merger, like signing three emails as “adeo” versus my nom de guerre, “ted,” to Fred Wilson, TechCrunch, and VentureHacks. Rumors were also starting to spread. Apparently, James Hong was telling everyone in the Valley that it was me, although James did not know. The stars had aligned:
- I was leaving a venture-funded role with an exit
- There was media interest in a large outing story
- I made some accidental and serious leaks
- Rumors were spreading
Well, all good things must come to end, of course. Instead of waking up one morning and learning that I was outed on PaidContent with a dozen angry voice mails awaiting, I decided to manage the story rather than the story managing me.
The next steps were pretty obvious: locking down the Wired piece and planning some type of event to bring both entrepreneurs and VCs together. Unfortunately, the cover of Wired never materialized and the publication date was right during Thanksgiving and earlier than expected. In hindsight, I have no regrets. It was only a matter of weeks if not days before someone else would have broken the story, and I am happy that I could change my cell pone number and address in time. 
