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Reflecting on a hard left turn career change

Over the last eighteen months I’ve helped source, interview, select and invest in 24 startups. As Director of Investments for Matter Ventures in San Francisco, twelve of those were my direct responsibility; twelve were supporting my counterpart Josh Lucido in New York City. 

Matter is - and continues to be - the best thing I’ve ever done.

The learning curve was immediate and intense, but I had been advising startups and analyzing the space for well over a decade. I had co-founded two, and was the first employee at a third. I’d also run a few things that weren’t technically startups but could have been: an online magazine in 1994 that found itself on the cover CD for “real” paper magazines, and a social media site that was getting a million pageviews a day in 2002. As an engineer, obviously I’ve built a lot of software - but more than that, I’ve spent every day of my career thinking about, researching, executing and advising on strategy. I love technology, and I love thinking about how to make it better.

But of course, technology isn’t worth anything unless it’s helping someone. The best technology pushes society forward and empowers people with new opportunities. Building new tech for yourself is fun, but it’s not a profession. And it’s just not very satisfying - at least, for me.

It’s been a privilege to get to know hundreds of people who are building ventures to solve real problems for real people. I invested in some, and wished I had room to invest in others. I gave feedback to many more. Most importantly, I was there on the ground with the Ventures we did invest in, helping with everything from fundraising strategy to database normalization. Rather than just writing code, or working on financial documentation, it’s felt like I’ve been able to use every facet of my skills to do this work. It feels good, and meaningful. And although I think it takes years to truly ease into this kind of work, I’m proud of the work I’ve done.

I doubt I’ll ever be an engineer again - at least, not solely. (My role at Matter is my first job since being a barista in college that hasn’t involved writing code in some capacity, but I’ve actually only ever had two pure engineering roles.) I’m certain that I will found my own venture again, and use what I’ve learned to create something that stands the test of time. But for now, I’m delighted to be supportive. Investing turns out to be one of the most satisfying things I’ve ever done (for all kinds of reasons that don’t involve money), and whatever happens in my career, I want to keep doing it.