Developing My Future

Those who know who I am are likely aware that in September I stepped down as CEO of Puppet, the company I founded, and whose first product I built. The question everyone asks these days is, “What’s next?”

However, I am committed to not committing to anything until at least the fall of 2017, which means I couldn’t answer that question even if I wanted to.

As a result, you have an opportunity to watch and participate with me as I take this journey. Along the way, I’ll be trying to share what I have learned and what I believe, and to the extent I can, my thought process as I figure out what’s next. If you follow along, I expect you’ll be informed, sometimes entertained, and at least periodically offended.

Taking Time

Part of my reason for delaying a commitment is that I want to spend the summer traveling with my family (a summer where both parents are unemployed and have some cash is a privilege and luxury I’ve never had and don’t expect again). Primarily, though, it’s about giving myself enough time to think deeply about what I want to do next, and why. By the time my last day at Puppet rolls around in March, I will have been working on Puppet for 12 years, full time.

Most people seem to think I started Puppet (or, more insultingly, I decided to turn it into a “real company”) when we first got investment in 2009, but in fact it had been my full time job since March 2005, and we were ramen-profitable by the end of the first year. Even before that, I had been doing sysadmin work full time since 1997, which means 20 years in one industry. Talk about a monogamous relationship! It’s impossible to spend that much time in one area, and then immediately pick a new direction that isn’t encumbered with biases resulting from such focus.

I am truly thrilled not to know what I’m doing next, to have the opportunity to explore ideas without a strong gravitational pull or a narrow time window in which to work, and just to be in a state of high uncertainty where I can pursue curiosity without worrying about how it relates to commitments I’ve already made. I am quite confident, though, that I will not be starting another company in the infrastructure space.

There are multiple areas where I think I would be excited to start another software company (most of them somewhere in the productivity space; if you squint, even Puppet qualifies as a productivity tool). But I’m also interested in helping to create many companies, not just one, which makes investing, advising, and board membership interesting. Diversity, especially in the tech world, is a huge priority for me, so it would be great to find some way to contribute meaningfully there. And whether I want to or not, I expect to spend some chunk of my time learning how to be productively involved in our civil and political discussions. Heck, some part of me feels guilty for not investing all of my energy there.

About the only thing I can promise is that whatever time I put into companies will almost all be focused - whether investing, advising, or operating - on helping individual people spend more time on the things they care about and add value to them, and less time on the menial work that gets in the way. That could take the form of productivity tools, automation, or management tools, for example. I’m generally more comfortable with B2B models, because I understand better how to build a business there, but I’d love to help build great tools companies for consumers that aren’t ad-driven.

If you’re interested in following along at home, I’ll be writing in this space as I pursue this decision, and hopefully after. My goal is to write often, and on any topic that strikes me, but you should expect to see articles on technology, finance, people, and the industry, with a periodic dose of just me being a person. I have many hypotheses right now, and not a lot of data, so I will be quite surprised if this space looks in a year like I’m thinking of it today.

My hope is that my writing is more about what I learn and conclude, rather than sharing my personal journey, but don’t be surprised if some of the articles are more about me than the industry.

For those who do decide to follow along, I hope you get some value, some interest, even some excitement from some of what I write. I also hope you’ll share with me anything you think is related, intriguing, or just confusing in topical areas. The best place to find me at this point is on twitter.



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