Introduction

An Entrepreneur’s Spirit

From an early age, I was fascinated by the concept of an office.

My father was a professor at Howard University, and he had an office at home as well as one at the university. While he worked at home, I’d hang out in there watching him do his “cool office things.” I’d mimic his office moves, trying to get his attention. I had never seen the office at the university, so I had to imagine where he went during the day and what that office was like.

Each weekday morning, while my father worked at his university office, I went to preschool, where I’d set up an office of my own. I recruited my fellow preschoolers in creating and running a tiny workplace. Of course, most of what we did, we had to pretend. No one was going to give us a stapler, for example, so we had to imagine a block as a stapler. My preschool mindset was “We’re going to produce,” and our preschool office mostly accomplished a lot of busy work, which is what—I found out later—real office work often is.

I’m pretty sure I was the boss. I didn’t know about CEOs or any of that, but there were five or six kids who were working for me. We were working together because girl leadership tends to be about flexibility and flux, usually not as rigid and hierarchical as boys tend to be in their play. But I was still the boss.

While I was running my preschool company, I had a side hustle going too. I had a boyfriend, Stevie, beginning in preschool through first grade. We dated for a pretty long time, even by adult standards. At the end of first grade, one of our daycare supervisors said, “You two have been dating longer than any of us have, so it’s time for you to get married.” On a beautiful June day, a sixth grader married us. I was very much in love, and we would “kiss,” which meant we would stand several feet apart and then lean toward each other, close our eyes, and eventually find each other’s face. It was a little precarious, but we enjoyed it.

The other kids found this behavior fascinating and would ask us to do it all the time during playtime and recess. Eventually, I grew tired of being simply a show for spectators, and for the first of many times to come, my entrepreneurial spirit kicked in. I saw an opportunity.

I told the other kids, “Look, if you want to see us kiss, it’s going to cost you.”

For big kids, third grade and up, the cost was twenty-five cents. For the younger kids, it was a sliding scale of five to ten cents, or whatever they had. Stevie, being a true romantic, had some moral qualms and emotional concerns about selling our love. I was able to mollify those concerns by buying us candy and ice cream with the proceeds. It didn’t make him completely comfortable, but it kept him cooperative in the business.

Fearless from an Early Age

The striking thing I remember as an adult looking back on my childhood self is that I was rarely afraid. If a fifth grader rolled up and said, “Kiss,” I had no problem looking right up at him and saying, “That’ll be twenty-five cents.”

On the other hand, I was also bullied. At the time, my family was living in an all-white neighborhood and I was going to an all-white school. The kids in our respective grades were fine, and friends helped protect me, but the kids in the older grades often hurt me and beat me up. More than once, teachers looked the other way. I took it upon myself to learn how to fight, and before long, I’d gotten to the point where I could fend off three bigger boys on my own. I broke a kid’s nose with a roundhouse kick. There was a lot of blood! Through it all, deep inside me was the strong will to stand true to power. As an entrepreneur, I draw on that will to stand true to power each day. I help other entrepreneurs find their will to succeed and bring great products and services to the world too.

If you’re reading this and thinking, I didn’t start a business in preschool. I don’t even know what a roundhouse kick is. I’ll never be an entrepreneur. I’m already behind, don’t worry. I may have been precocious about business as a child, but I didn’t fully learn how to tie my own shoelaces until I was in the fourth grade. And like many girls, when I hit puberty, I lost some of the sheer gumption and badassery of my seven-year-old self. It took time to regain her bravery and power.

Let me tell you something else: although I love technology and found my niche in Silicon Valley, I was never particularly strong in math and science, and I’m the worst coder in the world. I did, however, play a lot of video games. When I heard an internationally famous female leader in tech speak live for the first time, she said, “Most of the female engineers I know played video games as kids.” I played Space Invaders, Ms. Pac-Man, Centipede—all of them. My brother and I played Donkey Kong on our Atari 800. I became increasingly comfortable with computer interfaces, although an Atari 800 wasn’t quite what we’d consider a computer today. In addition to the joysticks, it had a keyboard.

One day I was bored, and I figured out that we could get into the command prompt of the Atari and teach ourselves Basic—a simple computer programming language. We were just screwing around, but I’m sure that early exposure sparked my desire to be a tech entrepreneur, and I’m grateful for it.

Doctor, Lawyer, Entrepreneur?

I never lost my interest in technology, but my parents had other plans. I was encouraged to be a doctor and discouraged from other pursuits. I wanted to be a kindergarten teacher, but my parents, both educators themselves, saw the concerning trends in American education and encouraged both my brother (now a pilot) and me to consider STEM occupations. As far as they were concerned, my future as a doctor, ideally a specialist, was decided.

There tends to be a strong drive toward identifiable, high-income professions for immigrants and minorities. Kids who seem like they might be able to go the distance are encouraged to become doctors or lawyers. If the people who influence them know what engineering is, they might become engineers. Becoming an entrepreneur or launching a startup doesn’t even cross the radar.

Christie Chirinos cofounded and was the general manager for Caldera Forms, which creates plugins for WordPress. In fact, the Caldera Forms plugin has been downloaded 1.5 million times and reached the top 0.5 percent of WordPress plugins in the world. Christie started early as an entrepreneur and didn’t get much encouragement from her mother. She now works with me as the VP of Technology at my newest company, Do Big Things, and told me her first startup story:

Entrepreneurship is about community. My first business and business website went live online when I was fourteen. I started offering piano lessons to the neighborhood kids to help fund my own music lessons, which my mother couldn’t afford. I often think about how my immigrant, single mother reacted to this. She didn’t say, “Wow, you’re an entrepreneur!” She said, “You’re not going to make a lot of money as a music teacher.” Immigrant families don’t see entrepreneurship the way that other families do, because immigrants have historically engaged in necessity-based entrepreneurship, not opportunity-based entrepreneurship. Necessity-based entrepreneurship is when people start businesses because of a lack of other work options—for example, not having a work permit or not being a desirable person to hire because of a language or cultural barrier. To my immigrant mother, there was nothing positive about my piano lessons business, because I was doing it because my family didn’t have enough money and because I couldn’t get a real job. Shifting immigrant communities’ perspective on entrepreneurship to recognize the potential of opportunity-based entrepreneurship to provide financial stability is important. This way, immigrant entrepreneurs will be encouraged and nurtured more.

Part of that tendency is the drive toward safety. There’s not a lot of safety in entrepreneurship. Being a doctor or lawyer feels, to many, like a safe profession. You’re definitely going to be respected in society, and you’re probably going to make money. For many entrepreneurs, especially women and minorities, that concept of “I need a safe profession” is one of the biggest obstacles—what I call speedbumps—they have to overcome.

I crossed my first speedbump in college. I began my studies in biology but left the first class with a deep inner knowing that this was not my destined path. I changed my major to ethics, politics, and economics, choosing to study subjects that were more in line with my interests.

Like many college students, I sought a job on campus to help cover my expenses. I wanted a high-paying job but also one where I could learn a useful skill. I headed to the library and applied for the job of computer assistant. I had recently set up my own Mac SE (while a male friend watched—I was scared!), so I thought I knew ALL about...