Goodbye to a Patriarch

This morning, my grandfather passed away.

Robert K. Greenfield was ninety-seven. He lived a long and interesting life, and he had a real impact on the world in which he lived.

When I was in sixth grade, I was given an assignment to write about a modern day Renaissance Man. I wrote about Bob and his knowledge and interest in countless areas — law, tennis, wines, public policy. At the time, he was seventy-four and seemingly winding down his life. Little did I realize that he still had more to accomplish than most of us do in our lifetimes.

In 2008, Bob had a health scare, and it looked like he might not have much time left. I wrote him the letter below, to let him know what he’d meant to me and my family:

I’d like to share a few thoughts with you, and hopefully give a little something back. You have played a considerable role in shaping who I am, and you will continue to do so, no matter what happens with your current condition.

Most people give up at some point or another. They try unsuccessfully to change things, and become cynical. They get worn down by the grind of life around them, and become indifferent. They succumb to greed, and become corrupted. They lose the discipline to take care of their bodies, and become slothful. They lack the intellectual rigor to seek truth, and become mentally lazy.

You aren’t like most people.

I am in an industry and a world that’s very different from the one you inhabited when you were my age. I sit in front of a computer all day; I solve algorithmic and mathematical problems, trying to construct a product that helps to bring people together; I try to stay as far from the legal world as possible! I am very much a product of my generation and my background: an Internet geek who lives in San Francisco, has traveled around the world, has no kids at age 30, and spends at least ten times as much money on food as on gasoline.

And yet, I cannot help but look to your example as a guiding force in my own life.

Elaine and I see your 71 years of loving marriage with Mommom as amazing, and something we aspire to (if we’re lucky enough to live that long!). We were so glad you made it to our wedding, and honored by your kind words there.

(An aside: a Chinese colleague of mine mentioned that she and her husband were very impressed by what you said; she said that your brief speech made it clear that you were the patriarch and leader of the family. Apparently these things cross cultural lines.)

I am continually impressed by the strong foundation you’ve built with the Goldsmith Prize. The more I learn, the more I realize how difficult it is to set up something like that, and the Goldsmith Awards have been an unbelievable success. Your combination of creativity, foresight, diligence, and personal relationships have uniquely crafted something special.

I will work hard to build on the Goldsmith successes, but it goes beyond that. I also use the Goldsmith model every day in my life: today I try to create a project of similar magnitude in the Internet world; tomorrow I may look for the next big thing in the world of philanthropy. Thanks to you, I’ve gained great insight into the process of creating something substantial, and a big boost in the inspiration needed to actually do it.

There aren’t a whole lot of people who can make me feel guilty for not working hard enough, but my 93-year-old grandfather is one of them. Your discipline, hard work, professionalism, attention to detail — I could go on and on — are astounding. I didn’t realize that when I was a ten year-old kid, but at a certain point I realized that your successes — academic, professional, family, athletic — were not the result of happenstance.

Many successful people get ahead by cutting corners, by sacrificing their principles or the common good. But that’s also not you: your honesty, your sense of fairness, your (stubborn!) desire to stick to the rules keep you grounded, and are yet another reason you serve as an inspiration to me and the rest of our large family. The ongoing trend in your life has been to look beyond what’s easy, and instead do what’s right.

My words are a mediocre expression of my sentiments and appreciation for all you have done for me and my family, but I hope they give some small sense of the effect you’ve had on my life. That effect will last as long as I will — thank you.

Fortunately for all of us, he lived another four and a half years. This past June, with dozens of family members, we celebrated 75 years of marriage between him and my grandmother. He got to meet my daughter a few months after she was born last fall, and then again before he died this month.

Amazingly, he was an avid reader of this blog. In his typical self-deprecating fashion, he explained how difficult it was for a “twentieth century mind” like his to understand the new things I was writing about. I know that wasn’t true.

The last time I saw him, less than two weeks ago, he was physically tired but mentally sharp. He was trying to figure out how policies around the fiscal cliff might affect his family, he was doing what he could to help with intra-family disagreements, and he recounted countless stories from nearly a century on earth.

Aside from the combination of physical frailty with mental sharpness, two memories from my recent trip stand out.

One memory is my grandfather’s awe at the possibilities that exist in the modern world. I shared some of my own startup experiences, and he explained how he wished he’d been able to do something similar. Bob certainly had an entrepreneurial mindset — after he retired he set up the Goldsmith Prize — but his day job as a lawyer was much more cut and dry. I’m incredibly fortunate: I live in a time and place where I can dream big dreams and run with them. Every day, I try to bring to my projects some of my grandfather’s intelligence and tenacity.

The second memory is a more personal one: my grandparents spent much of their time on the couch next to one another, savoring their final days together. My grandmother asked my grandfather if he still remembered their first kiss; he said he did, but amazingly their stories diverged. I feel sad for my grandmother: she’s only 95, with years of sneaky tennis drop shots ahead of her. But it was amazing to witness that kind of love after more than 75 years, and I’m glad that their four kids, fourteen grandchildren, and seventeen great grandchildren saw it and benefited from it too.

Thank you, Bob.

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.


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.


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.


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.