CHAPTER FORTY-FIVE

YOUR FAMILY

Someone told me once entrepreneurs are almost always either in their 20s or 50s because they're either “single and have nothing to lose,” or “have already made a lot of money and put their kids through college and have nothing to lose.” I'm not sure how true that statement is anymore—at least not in the U.S. tech scene, where I know lots of entrepreneurs in their 30s and 40s—but there's something to it.

There's a real incompatibility between the energy, time and long-range timing of financial return involved with a startup and having a family. You can't take your stock options to the store to buy diapers or cash them in for your monthly mortgage payment! Many people find themselves as both CEOs of startups and moms or dads at the same time, so it's worth writing a little bit about how the two coexist. I knew one particularly impressive female CEO of a company in our industry, Stephanie Healy, who started Vente with her husband as her COO, then promptly had four kids in six years, all while doing her job as CEO, then sold her company to a larger company in the industry. Wow!

Every person's family and family circumstances are different and it's hard to generalize suggestions in ways that make sense. I thought I'd focus on three topics that matter:

• Making room for home life
• Involving family in work
• Bringing work principles to home in smart ways

MAKING ROOM FOR HOME LIFE

I've already discussed the concept of “me time” in the previous chapter. It's critical if you want to maintain your sanity as a CEO. When you're a CEO who has a family, there is the related concept of “us time” or “family time” that you also have to maintain. You—and those around you—need to be comfortable that you have two critically important priorities in your life: your company and your family. Both could absorb 100 percent of your time and at any given moment the needs of one will have to outweigh the needs of the other. Perhaps most important, you will do your best to balance those needs out over the long haul but not necessarily within a given day, week, month, or even quarter or year.

One way of ensuring enough family time is to create a home Operating System just like your company or personal Operating System. This could be the subject of a whole book or chapter but the main point for the moment is that if you have some regular routines at home that you're expected to participate in (Friday night dinner at home, coaching a kid's sports team, etc.), you anchor your week or month or quarter around those as much as you use your board meetings or staff meetings as anchors to your calendar.

INVOLVING FAMILY IN WORK

I am fortunate enough to have a fellow businessperson as a spouse. More than that, Mariquita and I worked together at two different companies before we were married and have hugely overlapping personal and professional networks. Mariquita also happens to be incredibly smart and level-headed. As a result, she has been my most helpful adviser on a number of tough situations at work.

I know a number of CEOs whose spouses aren't in the business world—and no one's young kids are in that world (yet!). The typical reaction is to completely separate work and home and not discuss work “after hours.” This kind of separation might work well for some people but I don't think it could ever work for me. As time marches on, our personal lives and personal time increasingly bleed into our professional lives and professional time and vice versa.

My solution has always been to involve family in work, as much as is possible or practical. If I'm doing a little work at home and my kids ask me what I'm doing, I try not to just say “work” or “email.” I try to pause and explain what I'm actually doing in ways that they can understand. If I have a tough day at work and we're talking about “what happened today” around the dinner table, I don't mind telling everyone why I had a tough day. I try to explain why Daddy has to take yet another business trip and what I'm going to do in Place X.

I'd like to think that if I had a spouse who was a teacher or doctor that I'd be able to do a modified version of the same with her as well. Again, at best, we spend half our waking hours at work and half with our family, so we might as well make sure that our family knows what we do—and is proud of it.

BRINGING WORK PRINCIPLES HOME

As Mariquita and I wrote in our contribution to Brad Feld's book Startup Life, a marriage is the ultimate startup: building a shared environment with shared values and shared resources and working toward a shared goal. You and your spouse are co-founders in the most important type of organization—a family—and a constantly changing one at that, with kids arriving, growing up and having continuously new and different needs. A family needs to be led and run, consciously, thoughtfully and with a clear division of roles and responsibilities.

Mariquita and I work together to set goals for ourselves individually, our kids individually and our family as a whole—just like you would in any organization. We hold ourselves accountable to what we are trying to accomplish with regular check-ins. It isn't all work—the play part of the family is critical as well—but being intentional about what we are trying to build as a family takes time and has been an important commitment for us. The work principles of setting goals and budgets, creating an Operating System and following through on commitments, have helped us build our family life in really positive ways.

Similarly, I have been struck over the years by the realization that there are some real similarities between being a CEO and being a parent. To be clear, I don't think of my kids as employees (although there have been moments when I've wanted to put one or the other of them on some kind of formal performance plan). Just as important, I don't think of my employees as children! Skills required to be good at both jobs are very similar.

Here's why: Success as a CEO or as a parent requires core interpersonal competencies. For example:

• Decisiveness. Be wishy-washy at work and the team can get stuck in a holding pattern. Be wishy-washy with kids and they run their agenda, not yours.
• Listening. As my friend Anita says, you have two ears and one mouth for a reason. Listening to your team at work—and also listening for what's not being said—is the best way to understand what's going on in your organization. Kids need to be heard as well. The best way to teach good verbal communication skills is to ask questions and then listen actively and attentively to the responses.
• Focus. Basically, no one benefits from multitasking, even if it feels like a more efficient way of working. Anyone you're spending time with, whether professionally or at home, deserves your full attention. The reality is that the human brain is full of entropy anyway, so even a focused conversation, meeting or play time, is somehow compromised. Actually doing other activities at the same time destroys the human connection.
• Patience. For the most part, steering people to draw their own conclusions about things at work is key. Even if it takes longer than just telling them what to do, it produces better results. With kids, patience takes on a whole new meaning but giving them space to work through issues and scenarios on their own, while hard, clearly fosters independence.
• Alignment. If you and your senior staff disagree about something, cross-communication confuses the team. If you and your spouse aren't on the same page about something, just watch those kids play the two of you off each other. A united front at the top is key!

I assume that entrepreneurs who have families have gone through a lot of this chapter's experiences themselves, so I'll close with one very clear and unambiguous piece of advice. If you're a single entrepreneur, make sure you (1) make time for a social life so that someday you can have a partner and/or family and (2) before you commit to a permanent partnership—and certainly before you decide to have kids—make sure you think long and hard about whether you're ready for the changes that will invariably come and impact you and your business. If you're ready to move ahead, be intentional about changing your work life to make room for home.