A test in a series of tests.

I’ve always been fine with other people doubting me. Surely, that’s one of the many baptisms of being an entrepreneur. But, lately, I’ve been filled with self-doubt. An amorphous and unshakeable darkness that just weighs on my confidence. The end result is a nagging feeling that I can no longer create things of value or interest.

I think it all came full circle when I read Gideon Lewis-Kraus’ piece titled “No Exit” or “One Startup’s Struggle to Survive Silicon Valley’s Gold Rush.” I suspect that the experience he details is true for innumerable startups in the Bay Area, and it certainly would have been true for us at Leaky. The constant grind for validation and success spotted periodically with fleeting moments of pure elation.

It’s been six months since we closed Leaky, and in some ways, I think that I’m still recovering from the three and a half years spent building it. Since the acquisition, I’ve done the hand-wringing to investors, the obligatory period spent consulting, and capped it all off with a ‘what went wrong’ lecture tour that ended in a classroom at MIT.

presentation for MIT’s 15.565 Digital Evolution / Web 3.0 class

So what happens next?

Well, I suppose that all depends on what I’d like to happen next. And, what I’d like to do is prove myself wrong by creating something that is interesting, even if only to me.

“If you hear a voice within you say ‘you cannot paint,’ then by all means paint and that voice will be silenced.” - Vincent Van Gogh

And while, I’ve always enjoyed writing – my last blog was for Leaky, where I wrote hundreds of SEO-targeted articles on insurance. Before that, I had a personal blog, which consisted mostly of a looping .gif of a dog jumping over a fire, and it was lost when Posterous shut down.

So, I think I’ll make a start here. Just writing about things I like.