Entrepreneurial insomnia

This article first appeared on June 26th, 2012.

“If you’re not embarrassed by your first product release, you’ve released too late,” wrote LinkedIn founder and start-up guru, Reid Hoffman.

Today, I’m writing from my tiny hotel room in downtown Palo Alto.

We launched Posse two weeks ago and I can report that the time since then has been tough. Everything about starting this company has been hard: raising the first lot of money, hiring then un-hiring multiple people (lawyer, accountant, directors, staff, several technology partners), building the music product only to discover annoying barriers to scale, launching retail to discover customers didn’t want to use it, running out of money, raising money again.

Now, it finally feels like we’ve nailed the right model, have an amazing team and are not about to run out of cash. I really thought that this would be the moment of bliss when everything falls into place. Like coming out of a torrid journey through the desert where you almost died several times, to discover water and a neatly marked track called “home.”

Sure, I recognise our product is still in Alpha, needs a lot of polish, and 80% of the features aren’t built yet. However, I expected a moment of joy and peace where we worked in harmony with our users to iterate and evolve.

It would be like dancing, as the platform grew and became loved by all. Unfortunately, that’s not how it works!

One question investors like to ask is “What’s keeping you up at night?”

There’s always an answer. Since launching our site two weeks ago, three things – other than jetlag – have kept me awake.