18 months of wandering

In January 2018, I left as CTO of Cozy under difficult circumstances. Those of you that know me know the story. Those of you that don’t are free to buy me a coffee or beer to hear it. I joined Cozy in 2014 as Engineering Manager, and rebuilt and ran the company for 3+ years. Losing Cozy sent me into probably the first true bout of depression I’ve experienced in my life.

The 1.5 years since then have been a tumult.

• Dealt with actual Unemployment
• Took a job as an individual contributor at a tech company
• Engaged with the larger Portland startup community for the first time
• Took a side “job” (unpaid) rewriting a startup’s web app in just 3 months
• Went fulltime at the startup, as CTO/cofounder
• Did consulting side work for the first time
• Struggled with health insurance
• Quit the startup
• About to start a different job as an individual contributor

These last 18 months were a total rollercoaster, the most intense of my life. I’m really thankful for them, now that I’m on the other side and healthy and earning a real salary again at a job I intend to keep for a while.

Sometimes I think about an alternate universe where I stayed at Cozy, and they sold for a similar amount at a similar time. I’m incredibly privileged that I can say I’m better off I got out when I did- I wouldn’t have learned the things I’ve learned, wouldn’t have built the bonds with others that I built, and I know these will allow me to make a better impact with my life than some cash and complacency.

So I’m excited to start what’s next. I’m working as an Individual Contributor at Dwelo but on the side I will be starting a side project that I hope will develop into a company that can make a positive impact on the Portland business ecosystem. I’m not sure exactly what it looks like yet — I have some high-level ideas — and my hope with restarting my blog is to help explore some of those ideas to actually launch the business.