Start, Love, Repeat

1

Meet the Entrepreneur

My husband, Ned, entered college thinking he might like to major in music. Then he decided to be pre-med. Then he considered astronomy. Then audio engineering. Then physics. Electrical engineering. Environmental science. Computer science. Each time his major changed, he reorganized his entire class schedule, frantically adding and dropping courses right before the registration deadline. He usually ended up with an eclectic grab bag of classes, all of which he was already behind in. He would pull several all-nighters just to catch up in his classes and then push himself at full speed for the rest of the term to get good grades.

Ned and I became friends in the middle of our freshman year. “You’re studying what?” I found myself asking him each quarter. “Why?” I was bewildered by Ned’s behavior. I had come into college knowing that I wanted to study communications and was proceeding in a straight line toward completing my degree.

“Doesn’t it sound fascinating?” he would reply. “I wanted to try it in case I want to be a doctor/scientist/astronomer/engineer/musician/person who does something cool.” Occasionally he shot back with a cheerful, “Why not?”

Watching Ned change majors and course loads more often than I changed my hairstyle drove me nuts. But I still fell head over heels for him, in large part because of his gentle persistence and infectious curiosity.

Yet some serious questions surfaced as I weighed our potential future together. What in the world would he end up doing after he graduated? Could he even keep a stable job? What would life be like with someone so lacking in focus and decisiveness?

The issue, we both realized much later, wasn’t that Ned lacked focus. The challenge was that he wanted to focus on everything, to understand a bit of nearly every field. He worried about missing out on something better if he spent too much time and energy in one area. He actually enjoyed the rush of serially dating and dumping so many majors and classes. (Fortunately for me, he had no inclination to serially date and dump humans.)

We both should have known he was going to grow up to be an entrepreneur.

When Ned eventually graduated, he had earned two separate degrees: one in computer science and another in environmental science. He promptly found a job as an audio software engineer. I felt relieved that he was finally settling down. He had a real, stable, well-paying job, and he was getting ready to make a lifelong commitment to me. The wild days of his youth had passed.

Then, six months later, Ned quit his job. He had been miserable, his soul slowly suffocating under the weight of silent coding, socially awkward coworkers, and organizational politicking. He had no idea what he was going to do next. But he knew he didn’t want to be an engineer.

Alarm bells began to ring in my head, triggered by everything my parents had ever taught me about being sensible. Ned should have been able to suck it up, I thought, to do what he needed to support himself and be a responsible member of society. Yet I was still madly in love with this unpredictable, unconventional young man. As someone who had always played by the rules, I admired Ned’s willingness to buck expectations and plunge into new arenas without a second thought. He seemed fearless, bursting with confidence and hope that he could find work that was interesting, meaningful, and fun.

But I also worried there was something seriously wrong with him. If we ever merged our homes and our bank accounts, his freewheeling, devil-may-care approach to life could very well screw up my orderly existence.

Ned wanted to do something creative with music and technology, and after a few months of brainstorming and experimenting, he and a couple of buddies decided to develop personalized children’s music. They composed and recorded their own music, and developed an algorithm that seamlessly inserted each child’s name into the songs. Their families fully funded the business. I did not put in a cent of my own money, but I contributed countless hours burning CDs (the height of audio technology in the early 2000s), sticking on labels, and stuffing envelopes.

Even then, I didn’t quite know what to make of Ned’s venture. Interesting, yes. Fun, yes. Perhaps meaningful for parents stuck on road trips with demanding youngsters. But I couldn’t imagine him becoming a personalized children’s music guru. Was he going to tour the country doing personalized concerts? What did success even look like in this industry? Most importantly, was he ever going to make any income?

By the time we got engaged a couple of years later, in 2003, Ned was on to his next business. He had realized the children’s music market couldn’t be profitable. The market was too niche, the distribution network too limited. Instead he was going to record and sell original mobile-phone ringtones.

I’m sure I gave him a look—one that has become quite familiar to both of us over the years. “They’re huge in Europe and Asia,” Ned explained defensively. “People there spend a ton of money on ringtones.” He tried to convince me that even if I was content with the “Trio” and “Samba” ringtones that had come with my little flip cell phone, millions of other people in the world weren’t.

You may be wondering how Ned and I addressed my ongoing concerns as we prepared for our wedding. We didn’t. I didn’t know how to tactfully raise the issue without sounding like I was questioning Ned’s intelligence or character. And he, of course, didn’t even realize there was a problem to be discussed.

Truthfully, my modern feminist self didn’t mind the idea of being the stable breadwinner of the family. But I also didn’t want to marry someone who would be dead weight. Despite Ned’s excellent education and obvious talent, I thought this could be a real possibility—especially as he seemed to be running away from what he disliked (working for other people) more than he was running toward something he was passionate about. Children’s music and ringtones were intriguing to him. But it seemed to me that his real motivation was to avoid being gainfully employed.

In this regard, Ned is actually like most entrepreneurs in the country: one of the top reasons company founders give for starting up is that they do not want to work for someone else.¹ As I’ve talked with entrepreneurs and their spouses around the country, I’ve found this to be a common story. Aaron Armstrong of Maple, Wisconsin, left his job because of an abusive, belligerent boss. He decided to open a music studio, from which he currently provides private lessons and trains church groups on building music ministries. Chris Bruno of Fort Collins, Colorado, was successfully leading an American nonprofit in Turkey until his vision outgrew that of the higher-ups. His day-to-day job became about fighting against the limitations placed on him, which was slowly killing his passion for building new things. He knew he had to leave, though he had no clear sense of where he was going next. He tried out a few different jobs until he discovered a passion for supporting the personal and spiritual development of men through counseling programs.

According to a number of studies, the other reasons why men and women choose to start a new venture are primarily opportunistic: they are unemployed or underemployed, or they’ve been working in an industry for ten to twenty years and feel confident enough to start their own venture in that same space.² Entrepreneurs have also reported being motivated by the opportunity to build wealth, to capitalize on a business idea, or to work in a start-up culture.³

Women are still greatly outnumbered in the start-up world, making up only 31 percent of business owners—a statistic that has increased only five percentage points in the last two decades.⁴ But for females who choose to take the plunge, being their own boss may provide opportunities that working for someone else doesn’t. Despite being more educated than the male population, women still make only 80 cents for every dollar earned by men and hold only 14.2 percent of executive positions within S&P 500 companies.⁵

For Lauren Schneidewind of Atlanta, Georgia, the lack of “equal pay for equal work” in her job at a chemical consulting business pushed her to venture out on her own. She was shocked and angered to discover that her annual salary had been $20,000 less than her male counterparts. “It was probably a 20 percent pay difference. It was not insignificant,” she told me. “And they didn’t want to make it right. I could see no path for success there. So I said, ‘If you’re not going to pay me, I’m going to do it myself.’” She decided to start her own consulting firm.

Beyond the numbers, though, many entrepreneurs seem unable to do anything but strike out on their own. They just can’t help themselves, is what many have told me. That nagging yearning to start something often shows up early and can persist through changes in employment, income, marital status, and family planning. It’s like an extra protein has been embedded in the DNA of 10–15 percent of the population, a protein that is all about creating something new and sharing it with the world. “It’s just what they do,” Dave Phillips, an executive mentor and coach who has worked with thousands of executives around the world, told me. “They’re subject to their own poison. They’re a wild bunch. They’re unpredictable. That’s why they’re entrepreneurs: they can roll with the punches.”

Dave Boyce of Provo, Utah, is a classic example of the consummate entrepreneur. Now in his forties, Dave paused for a moment when I asked him how many different jobs he has had. “I counted once for a presentation,” he began, “and I counted forty-three different things I had been a part of in my life.” From mowing lawns and delivering newspapers as a teen, to starting bands and an a cappella group in college, to serving as an executive or board member for several companies that have been acquired, Dave’s life journey has been defined by his pursuit of new opportunities. This desire to try the novel, to provide something of value to others, has intrinsically been a part of who he is for as long as he can remember.

This tendency can show up even when someone has a clearly defined job with a large company. Henry Gross had worked in sales for Bloomingdale’s for twelve years and, throughout that time, he worked his job like it was a start-up. “He treated it like his own business, working long hours, traveling often, and doing whatever he had to do to get the job done,” his wife, Nancy, told me.

They had been married for sixteen years when Henry finally decided to leave Bloomingdale’s to start a specialty store in Princeton, New Jersey, the community where they lived. Nancy had just given birth to their first child. Despite her concerns with the timing, and the even greater stress and longer hours such a venture required, she didn’t think to stand in Henry’s way. “I worried that he would be miserable for the rest of his life if he didn’t do this,” she explained. “And it would be all my fault.”