Retro of a Startup Journey
It’s been just shy of three months since my last startup, Alegion, laid off about 1/3 to 1/2 of its Austin, TX office. Unfortunately, I was included in this layoff.
The swift contraction hit hard for everyone, but I felt somewhat uniquely impacted. I had:
- been the third employee
- worked there for almost six years
- relocated half way across the country with my family
- participated in building the company and the platform from the ground up
I have no idea whether or not it’s true that I was uniquely impacted. Everyone has challenges they have just overcome, and more challenges on the horizon.
At any rate, the last three months have been a whirlwind of changes.
My family and I made the decision to move back home to Seattle. We put our house in Austin on the market, bought a popup camper, and drove our dogs half way across the country. We stayed with friends while I was interviewing, and just this week I started my new job. We put an offer out on a house, and will close next month.
Things Done Well
There are things Alegion engineering did that I think were better than anywhere I have ever worked before. While I helped to design and implement these following successes, typically I was not alone in the effort.
Culture And Hiring
In the course of six years, I interviewed maybe one hundred candidates, and helped hire around forty of them. These candidates were screened for not just technical fit, but also fit for software development philosophies, humbleness, curiosity, desire to test, and commitment to quality to name a few of our core cultural qualities.
Overall, we were extremely successful in building empathetic, high performance teams.
Testing And Quality
As an engineering organization, all of our teams embraced the DevOps mindset. The team that wrote code, tested it, deployed it, and maintained it.
Tests were a big focus. Coverage was tracked.
Not just coverage, but intent, and overall quality of tests were points of discussion. Tests must be short and expressive. Each test should test one business function. A well designed test suite should communicate a story between developers.
As a group we aligned strongly on these values, and it showed in the quality of our code and the velocity of feature delivery.
Protect And Develop Engineers
Natural tension exists between product and engineering. Product almost universally moves faster than engineering in terms of feature ideation and business understanding, while engineering has a better view into platform technicalities, capabilities, and shortcomings.
Without a strong cohesion between product and engineering this tension can easily become inefficient, toxic, or otherwise damaging to team morale.
Shared responsibility, trust, and understanding are critical to the health of this relationship. The natural tension can be used to challenge each other in a healthy way, improve alignment, and increase trust through successful execution.
At Alegion, we did all of this extremely well. Each of my former colleagues, without exception, approached challenges with an open mind, integrity, and a strong desire to collaborate and to learn.
Through it all, I’ve had somewhat significant trouble processing all of my thoughts and emotions related to my career the last six years, as well as the layoff. This is a normal problem for me and I go to therapy to help develop my ability at introspection.
For one, I have a lot of regrets. If I could go back to square one with what I know now, the outcome may be different, and I could’ve been more successful in realizing my own goals. However, that’s not guaranteed, and not really useful to ponder over for too long.
I regret that I wasn’t better at empathetic communication from the beginning. I think this skill would have made a critical difference in my trajectory, as well as the trajectory of the company. Instead of being focused on the outcome, I should have been focused more broadly on the people and our interactions, in addition to the outcome.
I regret that I didn’t achieve my goals for my career at Alegion. From the beginning, I desired an executive leadership position. However, without the experience or vocabulary to articulate my goals, they remained elusive.
About three years into my employment, the company had been in growth mode. Individuals were hired above me, and before I knew it, there were no more leadership positions available.
I had worked so hard for three years, relocated my family from Seattle to Austin without a second thought, and my singular goal of an executive leadership position was simply out of the question.
Politics And Coalition Building
I regret that I didn’t do a better job connecting with my coworkers. If my goal was a leadership position, I should have been focused on building relationships across the organization, and not solely on proving my worth through delivering technology.
I regret that I didn’t focus more on quality vs speed in the beginning. I still believe speed is critical to the survival of startups, but I needed to balance quality into the equation a little more. I also regret not pushing back against more requirements up front. We were simply too ambitious too early.
I regret investing so heavily in a startup, so blindly. I worked many evenings, nights, and weekends developing the platform, building features, coaching teammates, and managing production. I worked from the delivery room for my first child. I took almost no paternity leave for two children.
I regret that my company evidently did not have the same intrinsic desire to invest in me.
This rejection was so unexpected, so complete, that I felt blindsided. The rejection cut deep, and I don’t know if I will ever feel the same. I may never work at a true startup again due to this experience.
To say this experience of rejection crushed me is an understatement. In hindsight, I don’t think I ever recovered from management’s decision to exclude me from any executive leadership opportunities.
Perhaps my goals were unrealistic given my experience and performance – that was the argument given to me. I have no such leadership experience. I have no proven record on delivering technology at a leadership level.
One question I frequently come back to is:
Why, in any sense, should Alegion have taken a chance on me?
Their decision to keep me in an IC role seems entirely rational and optimal given the situation, my experience, and the needs of the organization.
I had just naively believed that being an early employee meant that path was available to me (in fact, my boss had said as much in one of our early conversations, despite denying that path to me). This should serve as a warning to anyone else thinking that a startup is a good way to advance in their career path.
If fast advancement is a career goal, it must be explicit with clear, unambiguous, and achievable goals that the startup commits to in writing. Any less of a commitment, and you can wipe your ass with it, because that’s what it’s worth.
My startup experience was filled with what seemed like a lot of organizational successes, as well as personal failures. I’m not sure how much of this is true, how much of it is due to my mental health, and issues that I continue to work through.
I committed strongly to this startup, without really considering the sacrifices I was making over time to see the vision through. My mental health was severely damaged, and will take a while still to recover. My wife and I had two kids, and are probably done. I missed my opportunity to ever have paternity leave, and spend those first weeks/months focused on my family. I took vacation, but rarely, and almost never more than two weeks per year.
I had a wild ride, and learned a lot. From primarily web development experience in the beginning, to distributed microservices, DevOps, and security/compliance, there were a lot of turns that allowed me to hone my skills, as well as pick up new ones. I am extremely grateful for that experience.
My new job, which I started this week, pays more than I’ve ever made before. The pay increase is almost double my second largest pay increase. So, in that sense, the startup hustle paid off. It is also significantly less stressful. While the money is certainly welcome, it’s a bittersweet victory.
In the end, I don’t know if I will ever do another startup. Certainly not with the same leadership again. The emotional toll was just too much to outweigh the positive aspects of the experience.