Five years ago I moved to San Francisco from Atlanta, starry-eyed and eager to change the world. The information superhighway would give way to the information galaxy. Datacosmos (I called it) was the future and I had some part to play in it… but I had no idea how.

Enter failure: that painful blessing that steers us towards our destiny. When we do our best and fail utterly in our goal, we uncover a little more of our truth. As great as we think our goals are, what drives us are not those goals… but the oldest question of all: What am I?

Take these 4 major efforts of my life over the past 5 years. Each was a failure in terms of not reaching my goals. Each taught me truths I couldn’t have learned any other way–truths about my place in this world.

Decentralized Internet

Someone had to build the decentralized internet, why couldn’t I? I spent a lot of time designing and coding. Then I started the Secure Open Social meetup and discovered IIW and lots of other decentralized and collaborative internet meetups. That’s when I learned that the platforms of Datacosmos were already being built in various manifestations by people way smarter than me. So I abandoned the code and charts and speeches of Datacosmos and set my sights on what I saw as the missing piece: its first killer app.

Truth: Worthy dreams are shared by others. Find those people, hear them talk about the dream, then ask yourself honestly: “Am I doing my part to manifest this dream?”

Data Portability

I pitched and built Pipe at the Singly hackathon. Pipe would help you reconnect with one person a day from your social networks. It used Singly’s aggregation service that was born out of the Locker Project (part of the solution to help people harness their data). Pipe won best customer validation, #2 on Hacker News, and some press. The following few weeks were a stressful mix of getting the app ready for a production launch and stumbling through odd team dynamics. Everything felt off: product, team, and potential market… none of it was a good fit for me. So I let it go.

Truth: If it doesn’t feel right, it isn’t. Your gut is your greatest asset. You’ll be able to rationalize your gut feeling if/when you need to.

Data Ownership

I discovered Unhosted app architectures and built Gratzi, a gratitude app. I pitched it at the Personal Cloud meetup and launched a beta. We learned just how big a roadblock it was for people to connect another service (like Dropbox or Google Drive). Building a successful app AND architecting it in a way that doesn’t put us in exclusive control of user data… was like trying to go to the moon AND mars at the same time. Failsauce.

Truth: Focus. Do one thing at a time and do it well. Plus: if you’re making your users do work then you better give them a really, really good reason.

Sexy, Fun, and Deep

Then Becca, the muse, says why not build something that deepens human connection through fun? So we started work on an app that both goes directly at the problems of shallow social interactions AND is sexy and fun. Boom! We called it Pegg, attracted talented people to help us build it, raised a seed round, and launched dozens of betas. Each time we learned that we failed at getting the app right. We wanted it to rock people’s faces off, but what got was…

…not the face rocking we were looking for. But we kept at it nonetheless because we believed in the mission… and we were so close!

Truth: If all that’s in your way is execution, keep trying. You’ll get it right eventually.

And we think we have, finally, gotten it right. Pegg launches this year! I’m excited to put something of value out into the world and close this last chapter. I don’t know what lies ahead, but I’m certain it’s rife with great gifts of failure.

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