On Quitting as CTO, Wantrepreneurship, and Starting from Scratch

Shitting my pants before bungee jumping

Two weeks ago I quit my job as CTO.  With long aspirations to become CTO, it was a surprise to many, and at the time I realized it, to me as well.  As CTO you get to help shape the company in a significant way, which can be very rewarding.  From company to company the role can vary greatly as Werner points out.  As the company grows, leadership needs to have consistent values, messaging, and scalable operations.  Reticence and self discipline go a long way at a company that has its fair share of organizational and technical debt.  In fact, I've become convinced that what everybody in HR already knows: emotional intelligence is truly a defining characteristic of most good executives.  I was fortunate enough to have a sense of this from before I even started the workforce.  When I was a teen in the early and mid 90's the nature of intelligence was in debate and I was soaking it all in.  A book called Multiple Intelligences came out then a highly controversial book The Bell Curve and then Emotional Intelligence after that.  My general takeaway after this debate was that intelligence is simply the ability to adapt to one's environment.  That's a hotly contested opinion, but one that's stuck with me for a long time.  But here's the catch, you have to pick the right environment.  After scaling with the company for five and a half years, my personal career goals no longer aligned with the company's narrative.  Having considered myself a change agent for so long I realized I no longer had the drive to push things forward.  It was time to step out of the way to let the talented team I'd worked so hard to build, step up.

Being as it was, the decision didn't come easy.  My disposition is typically all-in.  I knew once that I'd lost the desire for my current job that I'd feel like a fraud.  It was important to me that I wasn't one of those employees phoning it in.  I absolutely hate that.  I'd sooner do something that's whole ass than half ass.  Second, the timing for me financially is amenable to being without income for a period.  I've deliberately lived my life free of financial burden and undue American materialism.  I have a reasonable mortgage, no other debt, no kids, and a wife that has a more than adequate income to sustain our standard of living.  The toughest part of quitting was leaving the team I'd hired.  Who you work with is paramount in my book and this statement from Peter Senge in the Learning Organization really strikes a chord with me

"When you ask people about what it is like being part of a great team, what is most striking is the meaningfulness of the experience. People talk about being part of something larger than themselves, of being connected, of being generative. It become quite clear that, for many, their experiences as part of truly great teams stand out as singular periods of life lived to the fullest. Some spend the rest of their lives looking for ways to recapture that spirit."

I've been part of a great team and when I was able to build my own I sought to define and establish a set of principles needed to rebuild something similar.

1. Create growth opportunity and narrative 
2. Find those who show an aptitude for continual learning 
3. Find those who work well with others 
4. Make sure the role and growth opportunity is defined 
5. Only hire those who give a shit

The good news is that with a dugout full of talented people they'll lean on each other and their own talents to find their path forward.  Of that much I am certain.

Those that know me well, know that I've had intentions on starting my own business for a long time.  Being an analytical person, I wanted to better understand the landscape.  By working for 4 startups in 10 years, I got to learn a lot.  As a developer I learned how to build and maintain software.  As a manager I exercised my people skills.  As an executive I've exercised my business acumen. Brad Feld talks about Wise's Talent Triangle in Startup Opportunities and I have 2 of the 3 covered: business acumen and operational experience.  So in essence, I think I have enough of a foundation to find success in the entrepreneurial game.  But unlike the rest of Brad's book I don't really meet the checklist of knowing when to quit your day job.  I'd give myself a 7/10.  But that's passing, right?

I'm sure there are many stories of how folks decided to quit their jobs.  It's not like I have this project on the side that's gaining traction and it's not like I have a co-founder who has wanted to start something.  Generally speaking, I'm at a pretty open stage with nary a plan.  I do have an idea that's nagged at me for sometime.  It's in a space I'm passionate about, but have little experience in.  The technology approach is appealing to the nerd in me, but I'm still trying to discover the market opportunity.  At the very least, I'd end up with some compelling technology discovery and perhaps a way with which to leverage that into a product will become clear.  I need time.  Time to explore and create.   It's been too long since I've created things or worked on a team that's building something.  I'm most eager to get back into that seat, get more hands on with coding and data science.  That in and of itself will be a win.

So far, it's an emotional roller coaster.  Having been at the company for so long, part of my identity was wrapped up in it.  Combine that with the fact that I'm not racing this year, I'm a ship without a rudder.  But it's also a good opportunity for reinvention.  I went to Boulder Startup Week, and got some great advice from a few mentors.  I've also reached out to old colleagues and old mentors.  It's really encouraging to have a good support network in my community and from my past in general.  But in the end you need to distill all the information you get into a direction.  Lean Startup is all the craze these days, but it's no silver bullet.  You can't substitute methodology for good ole fashion critical thinking.  Time to get to work.