Success at Work, Failure at Home

My brightest years running a startup were the darkest ones for my family

My oldest son drew this picture of our family when he was five years old.

My wife and I were college sweethearts. We delayed having children first by choice, then by necessity, as we put ourselves through business school. But nearly six years into our marriage, we agreed it was time. My wife and I both worked at startups and were committed to our careers; we expected that we would both pursue our careers and raise our first child at the same time. To facilitate that, we found an amazing, energetic, full-time nanny. In fact, my wife went back to work just two weeks after our first child was born, because the startup she was with was approaching an IPO, and our new nanny supported us through that period. When my wife became pregnant with our second child, I was a managing partner at Idealab, a startup studio, where a large part of my job involved shutting down companies that had been hurt by the dot-com bust. I planned to take some time off and stay at home while my wife went back to work six months after the birth, but by the time our second child was born, 22 months later, a lot had changed. Disenchanted with my work and eager to build something of my own, I had decided to start a company. As we brought our daughter home from the hospital, I had already launched into fundraising for what would be IronPort, an email-security startup.

It was just my co-founder and me in the beginning, and while we had an ambitious vision — to protect enterprises against all Internet-related threats — we didn’t yet have the resources to scale it. So initially, we did everything by ourselves. The life one signs up for at an early-stage tech startup involves getting in early, killing yourself to make something great, and getting a meaningful product out before you run out of money. This was true even after we started hiring people. I didn’t code, but as the CEO, I felt it necessary to be physically present with the engineering team. Sometimes, I would get everyone lunch or dinner. When we started pulling consistent coding weekends, we brought in the entire management team to serve the engineers: We brought them food, washed their cars, got oil changes, took in their dry cleaning, and arranged for childcare for their kids in the office.

Thanks to all the effort, IronPort ultimately grew to be very large and successful over its seven years as an independent company, before being acquired by Cisco. It was an incredible, once-in-a-lifetime professional experience. But those brightest years at work were without a doubt the darkest years at home. We had added baby number three just 18 months after the second one, which had forced us to make a decision about how to parent going forward. We did the math — and some soul-searching — and figured it would take two or more nannies and other staffers to allow us to keep pursuing work at our current pace. So, after years of working full-time in a startup with our first child, and continuing to work as its senior VP of business development after its IPO, my Harvard MBA wife, who had had an amazing career in her own right, “decided” to become a full-time mom and take care of our kids.

By the time we had three young children, I was rarely home. And when I was there, well, let’s just say I wasn’t particularly helpful or cheery. My perspective at the time was: I’m killing myself at work, so when I get home, I just want to kick back with a cocktail and watch some TV. All I do is talk to people all day long, and so at home, I’d really prefer just quietly relaxing. Then, as IronPort grew, I was constantly on the road with customers, press, analysts, and of course, employees. We ultimately got most of our revenue from outside of the U.S., and we all felt it to be very important to support our disparate offices from Europe to Asia to South America. There were several times when I was gone more than half of the days in a given month. Even when I was home, I was usually in this brutal state of sleep deprivation and recovery from adjusting to yet another time zone and couldn’t be relied on to help with childcare.

My wife’s experience was totally different. She was now home speaking in monosyllabic words to kids all day and was starving for adult conversation by the time I got in the door. And that part about sitting on my ass in front of the TV with a cocktail? This ran counter to all of her efforts to teach the kids about pitching in together as a family. The message of everyone helping to cook, clean, and be responsible for the household fell completely flat when daddy wouldn’t so much as take out the trash or change a light bulb. Nope, I was far too important for that and suggested she should hire someone to keep the house clean or even cook, if that was “stressing her out.”

Ugh. I was completely missing the point. I was setting such a great example at work, but such a terrible one at home, where I often acted like a self-important asshole. Something had to change.

After Cisco bought IronPort, I went to work for Cisco for a few years, then quit and took about 18 months off. During that time, my relationship with my family completely changed. I was packing lunches, driving carpools, making dinners; I began doing my part. With the help of my wife and other role-model dads, I essentially got re-programmed. In 2011, I joined Andreessen Horowitz as a partner. But my new role at home has continued to work for us even though I’m working full-time again.


My wife and I have now been married for 22 years. Reflecting on the years we’ve spent as parents, here are the most critical things I needed to change:

Disconnect to Connect

During the IronPort days, when my children were young, I thought what I was doing at work was far more important and urgent than what was going on at home. I was often accused of being physically present without being mentally present. (If you find yourself sneaking into the bathroom to complete emails, then you’re certainly not in the moment.) My wife dropped a bunch of hints, but I was undeterred. When I left IronPort, I realized that committing to my family required disconnecting from work (e.g. turning off the computer and phone), and completely focusing all of my attention on the details of the home. Cooking a great meal. Helping with a science project. Discussing the future with my partner.

Planning and Priorities

My wife and I have a weekly date night. My son and I are in a fantasy football league together. I cook with my daughters. Most times these have become immovable appointments on my calendar. When my calendar reflects that I can’t do a meeting on Wednesday and Friday mornings before 9 a.m., because I cook breakfast and drive a carpool, then it’s amazing how meetings just don’t get scheduled. (If it’s at all possible, living physically close to the office is also a huge help to juggling the priorities. It means that I can cut out for a family dinner and then go back to the office or have a late meeting afterwards.)

Communicate

When I was traveling at IronPort, I would sometimes go for days without communicating at all. When friends would ask my wife, “Hey, where’s Scott this week?” she would sincerely have to answer, “I have no idea, you’ll have to email him yourself.” I was that sucked in. Now that I am completely tuned in to the weekly family schedule, we plan and calendar family meals (perhaps the single most important thing we do), pickups and drop-offs, and make adjustments on the fly. For example: Did some time suddenly free up so I can catch the last 30 minutes of the kids’ basketball game? Can I pick something up on the way home? And so on. My norm is to check in between meetings, but if I’m the “parent on duty” — i.e., if my wife is out of town — then I will start a meeting with, “You’ll have to excuse me, but I’m the only parent in town so I need to keep my phone handy in case of an issue.” Communication was by far my biggest area for improvement. Now, multiple, daily phone and text check-ins are the norm. Communication is important in a broader sense, too. I believe that families — and that includes everyone — need to discuss each parent’s life-changing decisions, such as joining a startup or becoming a CEO, together. And they should reserve the right to change the contract as their life together evolves.

Participate

It’s just not possible to be a real partner if you aren’t deeply involved in all aspects of the family; you can’t just ask your partner to delegate certain tasks to you. Or maybe you can, but then it needs to be a mutual, shared decision — one that honors your partner’s choices and dreams, too. But I personally believe that even the busiest CEOs should drive a carpool, pack a lunch, help with homework, make a breakfast or dinner, and consistently attend school events. And note, my wife didn’t need another person to “manage” in the household; she needed me to “own” some of our family life activities myself. Being involved every week is the only way to stay connected at home, and it cannot be outsourced. It might even make you a better CEO since you’re more sensitive to the needs of others.


There’s a debate that rages in the corridors of VCs, startups, and other intense entrepreneurial centers, which is: Can you have it all? Aren’t the best CEOs and founders so ambitious, so driven, that they must sacrifice everything to make it work? We have seen couples struggle with this on a personal level, and there is almost always an imbalance that leads to deep sacrifices on one front or the other.

What historically has been somewhat unique to Silicon Valley is the age and experience level of CEOs; that role is often achieved a decade earlier than in traditional industries. I’ve observed that CEOs in their 20s may be fully equipped and knowledgeable enough to handle leading a company, but when their family life begins to expand and demand for their attention increases, they are at a loss as to why things aren’t just falling into place. The changes that I’ve described ideally should be made before you get to that point.

It’s easy for me to share this advice now — after I sold my company. The reality is that it took certain sacrifices, in terms of my family life, to make IronPort a success. Still, I’m hopeful. I’m hopeful that the new generation, having grown up with more permeable boundaries between work and home, and being used to new technologies to keep them even more connected in ways we couldn’t be before, refuses to accept a world in which one can’t have it all.


An earlier version of this post appeared on a16z.com.

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