Confessions of an Entrepreneur's Wife

In January 2004, we sold our airplane. A private plane may sound like a rich person's luxury, but Bill and I had been pilots for years, depending on our single-engine Beechcraft Bonanza the way most families use a second car. We flew to visit relatives and take vacations; it was often cheaper than buying three commercial tickets. When Bill started The Switch, we joked that when it came time to sell the plane, that's when he would bail on this whole start-up thing. We laughed about it, but I was serious. For me flying was a stress outlet, a quick way to visit my family, and a source of income. (I wrote frequently about aviation.) My father, who had died 10 years earlier, taught me to fly and left us the money to buy this plane. It was a huge part of my identity.

And yet, when it came time to sell, the decision was easy. Neither of us had time anymore to stay current with our flight training. And the plane cost nearly as much to maintain when it sat in the hangar as when we were flying it. Money was tight because I was essentially not working and Bill didn't have a big corporate CEO salary. Even though I knew selling was the right thing to do, I couldn't bring myself to go to the hangar and say goodbye. I let Bill fly it to the broker.

Sell, Sell, Sell...Stop Selling

Up to that point, the company had been through ups and downs, but what happened at the office affected me only indirectly. There were moments when Bill landed a big new account, like 7-Eleven, Target, or Costco, and we went out to dinner to celebrate. And also times when he warned me that it might all collapse, and I frantically created an emergency budget for the household. But the company's next problem hit me even harder than it hit Bill.

In the spring of 2004, Bill hired a friend of ours to handle operations. Of course, I had heard from countless CEOs in interviews about the risks of hiring friends, but I wasn't worried. Doug was himself an entrepreneur, having helped start a software company. We lived in the same neighborhood and I saw either him or his wife, Claire, nearly every day. We baby-sat for each other and volunteered together at the school, where we had children in the same third-grade class. Doug and I talked frequently on the playground; he was one of the few people I felt comfortable being completely honest with about the company-caused stresses in my personal life.

I was thrilled when he joined The Switch. I hoped that in Doug, Bill would find a supportive and entrepreneurial partner, someone to share the load so that Bill could spend more time at home, or at least be more relaxed. But that didn't happen.

Before long, Bill decided that Doug didn't have enough industry experience for the job. They talked about it, and Bill hoped the situation would somehow resolve itself, but he warned me that it might not. I worried over the ramifications a bad outcome would have in our small community. Bill reassured me that it was just business, but it sure didn't feel that way to me.

The members of the board finally insisted that Bill fire Doug. This time, Bill was able to think of it as simply a company event, but for me it was worse. Doug was angry and the accusations he made were ugly. I felt terrible that it hadn't worked out, but I also felt betrayed by a friend.

There must have been some juicy gossip among the parents on the school playground, but I unloaded only to my closest and most tightlipped friend and then clammed up. Another friend mentioned that she was helping Doug in his job search. I suggested that she get Bill's side of the story, but she said, "I don't want to know the details. The guy has to support a family and I just want to help." It was a good reminder that there was more to Doug than just our recent experience. I focused on adopting the same open-minded attitude and wished her well.

Ever moving forward, Bill turned to his biggest challenge yet. The company was once again running out of capital, and a Texas investment firm that had promised $1.5 million had delivered only $800,000. By now he was familiar with how to eke out operations with no cash--factor the receivables, pay only production and payroll expenses, and string out everything else. I began to realize why it was that the most successful CEOs I had profiled had come from sales backgrounds. I had always thought it was because a CEO can sell the product like nobody else. But it's so much more than that.

As I watched Bill set off on another fundraising search, I realized that a CEO sells everyone. When he asks for money, he's selling potential investors on the product. He told me once about a VC breakfast he went to early on. He described the other CEOs who were there and the companies for which they wanted funding. Some had great ideas, Bill said, but out of a half dozen who presented, salesman Bill was the only one who came right out and asked for the money. And the only one who got it, he learned later.

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