“The motion has passed.”
Click. Beep. Click. Beep.
“The organizer has left the conference.”
And just like that, we lost everything.
Greg and I sat in his basement apartment and exhaled. That friendly female robot was gently informing us that our final board meeting was over, and that we had just been fired from the company we started. It was a stinging message delivered with a peppy, upbeat voice.
“Well, what do we do now?” he said.
“Let's just drive.”
We needed to get out of Boston. It was early August 2014 and the humidity was thick. After so many months with all-day meetings punctuated by all-night coding sessions, I was feeling claustrophobic, burnt out, and emotionally exhausted.
We hopped into my 2000 Nissan Altima, crumpled up another parking ticket, and started our westbound journey on the Massachusetts Turnpike. It was an odd feeling … driving in the opposite direction of our office in the middle of a workday. The entire team was back there, going about their ordinary business. Greg's sales team was trying a new go-to-market strategy calling on university advancement offices. My engineering team was cranking away on the new version of our mobile event management app.
The day probably seemed completely normal to them, but they were unaware that they no longer had bosses.
“Where are we going?”
“I don't know. Maybe Cleveland? Chicago? We could just go to California and start something new.”
I didn't really care where we ended up. I was numb.
My phone was still buzzing with notifications for website errors and other alerts that I normally needed to attend to as the technical leader. It was now someone else's problem, but it certainly didn't feel that way. I was still CTO in my mind, and I was still debugging, thinking through ways to rearchitect our software in the future.
Greg didn't say much as we drove. This whole thing seemed to hit him more quickly than it hit me, and I understood why. As CEO, he had convinced 30 of the most talented people we could find to quit their jobs and join us in this crazy, risky venture, most of the time with a sharp pay cut. He always felt an intense level of responsibility for our team and their future, and he feared letting them down.
“I'm hungry. Let's just pull off here.”
Our getaway lasted about 20 minutes. Normally at this hour we would be perched in our tower—an art deco Fenway office with sweeping views of the Boston skyline. But on this afternoon, a McDonald's booth in the Framingham Service Plaza was good enough.
Over a carton of McNuggets, we recounted the events that brought us here. Back in the spring, everything seemed great. Sales were up, product was moving, demand was growing, and we had a clear path to success. The whole thing started to feel like a real business, and one that could legitimately take off.
But by mid-summer, we were out.
I always thought that our downfall would be some major product bug, or loss of data, or running out of money, or not hitting our sales numbers, or any number of reasons you typically hear about entrepreneurs failing. But it wasn't any of those.
What ultimately did us in was so much simpler and more human than that … we understood technology, but we did not understand people.
FLYING BLIND IN A COMPLICATED WORLD
At the start of 2013, we were a couple of young, ambitious entrepreneurs who followed the startup playbook and tasted some early success. Build a product, raise venture capital, hire a team, make sales. Code, raise, hire, sell. The scrappy startup grind rewards immediate, independent action. Collaboration and communication were less important than simply getting things done. It was surprisingly comfortable for us.
However, as soon as the company started to scale beyond the walls of our Mission Hill apartment and we hired the first few employees, we saw both of our jobs change significantly. I had less time to code and spent far more time interviewing, instructing, and coaching. Greg's schedule was dominated by meetings with prospects, partners, customers, and candidates. Without any intentional decision on our parts, our jobs changed from producers to leaders. With almost zero real-world management experience, outside of some university clubs, it was uncharted territory. But, like everything else, we planned to learn on the fly.
And for the most part, we did. Despite plenty of growing pains over that next year, our team expanded, we figured out our business model, and eventually had a real, growing company on our hands. At that point, we began to witness some of the same people-related challenges that most leaders of rapidly growing companies see. Communication needed to be formalized, otherwise details would fall through the cracks. The culture needed to be set up intentionally, otherwise bad habits could take hold. Our hiring process needed structure and standards, rather than pure gut feel.
The stakes were rising, and we did not want to mess this up. We wanted to be real leaders instead of imposters with C-level job titles. And we knew we had blind spots—some we were aware of and others that we were not. So, we sought help and hired an executive coach, Walt, who came highly recommended from a fellow founder.
