After the Thrill Is Gone

A growing startup can be bliss.

When Circle of Friends was growing rapidly, I’d wake up suddenly at three AM, my heart jumping with a mix of excitement and nervousness. Because our technology was brittle, I’d walk out to the kitchen and look at my laptop to make sure the site hadn’t crashed. And I’d notice that, amazingly, our traffic for the period between midnight and three AM was our highest ever.

Our highest ever? Our highest ever!?!? How could I go back to sleep now? It was three AM and my day had started: I boiled some water to make a pot of tea, and I got to work.

That was the startup honeymoon phase, and it was exhilarating.

Moving

Circle of Friends (which became Circle of Moms) had its first office in our little house in downtown Palo Alto. We’d bought the house in 2006, knowing it needed work. Elaine, being an architect, saw this as a positive: it was a house we could truly make our own.

After a few months where I was both living in the Palo Alto house (with Elaine) and working in its kitchen (with Ephraim during the day — but alone at 3 AM), the center of my world moved to San Francisco. Elaine and I decided we’d rent out our house and find an apartment in the city, and Ephraim and I would get an office in SoMa.

That basic arrangement — living near Dolores Park in SF, working South of Market) — was my life for nearly four years.

When, in early 2011, we found out Elaine was pregnant, renovations on our house in Palo Alto were nearly finished. At that point, we hadn’t decided what would happen after the house was ready to live in: we were open to selling it, renting it, or living in it ourselves.

The fact that we’d soon have a little daughter made living in it — and a move to Palo Alto — more appealing. Our own new place, with a nice room for baby, lots of natural light, a beautiful kitchen (nice work, Elaine!), and an edible garden seemed like a great option.

But I also knew myself and my work patterns. It was hard to imagine having a baby, a startup, and an hour-plus commute. Dealing with two of those three would be challenging; dealing with all of them would just be stupid.

The more I thought about it, the more I realized what a move to Palo Alto would mean: the beginning of the end of my time at Circle of Moms.

Elaine and I soon decided we’d move back to the house when our daughter was born, and that meant my time at Circle of Moms would be limited. Certainly not “I’m giving two weeks notice” limited, but also not another five years.

I told Ephraim of my intentions, assuring him that my goal was to get Circle of Moms to a place where we’d both feel comfortable telling the team that my role would change. We agreed that it would not yet make sense to share those plans with the rest of the Circle of Moms team.

That marked the beginning of a very different phase from the one where I’d wake up at three AM and excitedly sit down to work.

Departures

On a Monday morning in July 2011, Elaine was now six months pregnant, and we were at the doctor’s office. She had gone to the bathroom, and my phone buzzed with an IM from a colleague.

hey mike – will you be in the office today?

“Yes”, I replied, “am at a doctors appt now, will be in around 10″. A moment later, I got my colleague’s response:

oh okay – can i grab you for a chat sometime before 11?

Before 11? Crap. She’s going to tell me she’s leaving the company.

I was right, it turned out. And though my co-founder and I did what we could that week to try to convince her to stick around, we knew our odds were slim. We were ultimately unsuccessful, and she left Circle of Moms a few weeks later.

The Responsible Founder

At the time, there was a part of me that wanted to check out and move to the next thing, but as a responsible founder, that wasn’t a viable option.

In each of my three jobs before becoming a founder, I’d decided at a certain point that I’d had enough. Within weeks of coming to that conclusion, I’d told my boss I was leaving; by a few weeks after that, I’d formally moved on.

On that July Monday in 2011, I’d just heard my employee’s plans to leave and join another company, and I knew she’d soon be out the door. Meanwhile, my writing was on the wall and I was ready for something new — but acting on it now was simply not an option. I had to pull myself together, convince the team that everything would be fine, and get back to work.

Fortunately, the process went about as smoothly as it could. The team took things well, another employee immediately stepped into the shoes of the woman who departed, and we continued to make progress as a company.

But that summer was still a challenge for me personally. Weekends, which Elaine and I spent in Palo Alto, were awesome. We were in our beautiful new home, getting everything ready for ourselves and for the baby, cooking in our spacious kitchen, and enjoying the warm sun. During the week, we’d stay in cold, foggy San Francisco, and slowly pack up everything from our small dark kitchen.

Several other people left the company over the next few months. Our traffic was growing and we were executing well on the product, but we certainly didn’t have rocketship growth and our talented employees had plenty of other options. Again, I was tempted to follow my employees and also move on to the next thing; again it was not an option.

With all of that going on, I’d become more and more open to being acquired. That was a big change from a year or two prior, when the acquisition offers that came our way held little appeal for me: earlier, I would have been disappointed if another entity had ultimate control over the product and the company. But now, I’d been through the startup building process, realized I was unlikely to be the visionary of this business, and was open to a “strategic partnership.”

I spoke with another founder who had recently been through the acquisition of a similar-sized company. At a certain point, he told me, he’d realized that his company wasn’t likely to be a huge success, and that an acquisition was the way to go. He spent an entire year getting the company to that stage, in the process building relationships with his eventual acquirer, and said it was easily the toughest year of his life.

Leaving

Our experience was much the same: it was just under a year from the time I knew I was ready to move on until February 2012, when Sugar acquired Circle of Moms. It wasn’t the most fun year, but it was a productive one in many ways.

And I was fortunate. With a combination of luck and skill, we’d already built a real business, a strong team, a solid product. We wound up making money for our investors — even if it wasn’t a billion dollar sale — but the process still took us a year. Many founders spend a year or more on the less fun parts of running a company, without seeing a positive exit.

Christine Tsai, with whom I now work at 500 Startups, wrote a great essay comparing parenthood to building a startup. I agree with everything she says: in both domains, you work hard, it’s hard to figure out who to listen to, and it’s terrible… and fantastic.

There’s one other parallel I’ll add. As both a founder and a parent, you’re responsible, and you can’t just pick up and leave when you feel like it.

A mother’s work is never done. A founder’s work most likely will eventually be done, but it certainly won’t be today at 5 PM, and he can’t know in advance exactly when it will be.

And that means a founder can’t just give his two week notice and disappear. Even after the thrill is gone.

Mike Greenfield founded Bonafide, Circle of Moms, and Team Rankings, led LinkedIn's analytics team, and built much of PayPal's early fraud detection technology. Ping him at [first_name] at mikegreenfield.com.