Overactive Vocabulary

When In Doubt, Ameliorate


The Third Decade

Or, I’m Stepping Back from Daily Operations at Spreedly

My professional life has run roughly in decades: a first decade of getting into the software industry, doing lots of consulting and contracting, and observing businesses being run. The second decade grew out of the first decade and was spent founding a product company and figuring out - alongside a lot of really smart people - how to grow Spreedly into something successful. The boundaries between these vocational periods are of course fuzzy, but over the course of 2018 I’ve unknowingly been wrapping up my second decade, and the end of 2018 has become a clear break from my time working on Spreedly on a day-to-day basis.

Here’s the thing: Spreedly’s in a fantastic spot to win. I feel really good about stepping away right now with the company profitable, compounding sales growth, a great leadership team, and a product that has one of the lowest tech debt loads of any production system I’ve ever worked on. And I’m not disappearing into a black hole: I’ll remain a shareholder, continue to advise the company via my position on the board, and be cheering the team on from the sidelines every step of the way.

Why am I leaving? As these things usually are, it’s complicated. Here’s the short version: there were differences of opinion on my role as Spreedly grows past 50 employees. And I mean “opinion” sincerely - I haven’t even been present at a product company as it went from 50 to 100 employees before, much less been an executive working on it at that stage, so my perspective shouldn’t weigh more. And since I wasn’t able to get on the same page about my role going forward, I didn’t want to get in Spreedly’s way as it continues to grow.

What’s next for me? I ask rather, “What better time for a mid-life crisis?” and I’m only half-joking: while I’m not in crisis, I have about a million ideas for what I might want to work on next, but 2019 is all about getting back to the basics of creation: writing consistently and programming consistently. These two skills have formed the bedrock of my career to date, and I’m excited (and terrified) to pull my creative focus away from Spreedly and put it into a series of smaller projects designed to hone these two fundamental skills while exploring a series of hypotheses about what my next major endeavor might be.

Alongside the fundamentals, I also expect to do a lot of networking in 2019, so do drop me an email if you want to grab coffee or even just video chat. This goes double if you’re a CEO, CTO, or VP of Engineering in a company in the 10-50 employee range trying to figure out how to wrangle engineers and the software they build - that’s where all my scars are from and I feel like I can speak with some confidence about what works and what doesn’t.

Weep not for me! I’m super excited to dig into the third decade of my career. And worry not for Spreedly: it’s set up to win, top to bottom, with an amazing team building an amazing product. Instead, grab some sunglasses: the future is bright everywhere you look. 😎