Support a Passion
Almost all the successful entrepreneurs profiled in this book have one experience in common—they had their parents’ (especially their moms’) support to pursue a passion, generally one they engaged in outside of school. Whether that passion was sports, computers, music, video games, selling things to neighbors, or even protesting, it made them great future entrepreneurs.
Lots of the moms I talked to didn’t “get” the activities their kids were into. But they also knew that their own interest or understanding was beside the point. What they went out of their way to support wasn’t so much the activities themselves as the spark it brought to their children’s eyes.
Your own children’s passions may not be the ones you would have chosen for them. Their passions may not even be something you understand. But that’s actually a great thing, even if it doesn’t always feel that way. It means your kids are exploring their passions in ways that are most meaningful to them, rather than following in your footsteps or trying to please you.
Letting children run with their passions isn’t really about helping them fulfill their childhood fantasies. It’s not about helping a kid become an astronaut or a billionaire or president of the United States (though all those are possible). The true benefit is that, even if a child’s passion doesn’t turn into a profession, they learn the joy of diving deeply into a pursuit, discovering all it has to offer, and making connections with others who are also passionate about it. Kids learn that good things happen when they do the things they love. And if they keep exploring, they find ways to improve or add to or expand or reinvent or promote the things they love—and that’s how companies and organizations get started.
It doesn’t really matter what your child’s passion is, as long as your child is passionate about something. And the most important thing you can do is nurture that passion. If you do, your child will devote lots of time to it. That’s what it takes to become truly accomplished at something.
Glenda Chasen has two sons, Michael and Joel, an entrepreneur and an endodontist. Michael graduated from American University and then got an MBA from Georgetown. In 1997, he started Blackboard, an online educational technology company that he later sold for $1.5 billion. He then went on to cofound SocialRadar, a tech start-up that developed a location-based social app.
When I talked with Glenda, she told me that growing up in the 1980s, Michael had a passion for computers, which were just becoming popular, although most people had no idea that they eventually would transform society. When Michael was in fourth grade and wanted to spend lots of time on the computer and playing video games, she nurtured those interests.
Glenda told me that she had been somewhat alone in this—the other moms encouraged their children to engage in academic pursuits “worthy of their intellect,” as Glenda put it. Her friends told her that Michael was wasting his time. But she resisted the peer pressure and continued to encourage him as he played video games. He had a passion for gaming, she said, and he loved computers, so she not only let him spend lots of time on video games, she also told him he was wonderful for doing that. By embracing his expressed interests, she helped lead him to success.
Glenda did the most important thing parents can do if they hope their children will become entrepreneurs: nurture their passion. Sports, art, chess, music, drama, fitness, computer games, volunteering, church…it doesn’t really matter, as long as they are passionate about something.
Jon Chu is a screenwriter and director best known for directing Step Up 2: The Streets; Step Up 3D; Justin Bieber: Never Say Never; G.I. Joe: Retaliation with Bruce Willis and Channing Tatum; and Now You See Me 2 with Daniel Radcliffe, Jesse Eisenberg, and Mark Ruffalo. When I talked to Jon, he told me about his early life and how his parents supported his passion, once they understood how much it meant to him:
I grew up in Silicon Valley in the eighties, surrounded by people creating stuff, where engineers were the heroes.
My mom came from Taiwan, and my dad from China. They were both around twenty when they came to the U.S. They met when my mom was going to the College of San Mateo and a friend introduced her to my dad. They started a little restaurant in Palo Alto, Chef Chu’s. It’s been there over forty-five years and has become a neighborhood institution.
I was the youngest of five, and the oldest was only six years older than I was, so we were all very close. My second brother, Howard, is autistic, and so my family became okay with going with the flow. If we all went to a play and Howard didn’t want to stay, we left. We learned to adapt. Today my oldest brother, Larry, who graduated from UCLA, helps at the restaurant, which he’ll take over some day. My older sister Chrissy is in real estate. Howard is at home with the family. And my sister Jennifer is married and raising two kids.
My grandma helped at the restaurant with the accounting, and she used an abacus. Her feet were messed up from having been bound when she was a girl in China. My parents would tell us to look at her to realize how far our family had come in just one generation. They’d always say, “America is the greatest place on earth—if you work hard, you can achieve anything.”
My parents never let us work at the restaurant. They would tell us, “We didn’t have many opportunities growing up, and we want you to do everything we didn’t.”
My mom kept us super busy. I took music lessons on almost every instrument—drums, saxophone, guitar, piano, and violin. I also took tap dancing lessons and played tennis.
Every weekend we would go to San Francisco to see a show—musicals, ballet, symphony, theater. My mom thought we were royalty. My brothers and sisters took etiquette classes and ballroom dancing to learn the foxtrot and waltz. She had a pretty clear idea of who she wanted us to be—the Kennedy family!
My brothers and sisters and I were in all the school plays. I had the most encouraging parents. They came to everything we were in and always supported us. At the time, I thought we were really good, because that’s what my mom kept telling us. Looking back, we were actually really bad, but I didn’t know it then.
Somewhere amid all that exposure to the arts, Jon discovered his calling:
I’ve loved making movies for as long as I can remember. When I was in second grade, my parents gave me the video camera to shoot our family videos while we were on vacation. I had to figure out how to use it. I loved it. I was cutting stuff and editing on the VHS.
I started an illustration company when I was in third grade. When I was in fourth grade, I saw an ad in a Sharper Image catalog for a $200 mixer. Suddenly you could take music from the stereo and put music on your VHS videos! I had to have it.
I called my dad at the restaurant and begged, and I talked them into buying it for me. When I got it, I cut together my vacation video and put music in it and showed my family. My parents started to cry. I knew then that I wanted to do this for my whole life.
I wasn’t the best musician, even though I played lots of instruments. I wasn’t the best at drawing, even though I loved to illustrate. And I wasn’t the best actor, even though I’d been in lots of school plays. Making movies connected all my interests, and from the very first time, I knew it’s what I wanted to do forever.
But even when parents are as supportive as Jon’s, they can have a hard time seeing the value of a child’s favorite activity. It’s easy to worry that what a child loves has become an unhealthy obsession, one that will limit, rather than expand, their options:
My freshman year in high school, I convinced a lot of my teachers to let me turn in videos instead of writing papers. One night, very late, when I was supposed to be asleep, my mom came into my room and saw me working on a video.
Mom said it had to stop.
I started crying. “This is what I love,” I said. “You can’t make me stop!”
The next day, when she came to pick me up after school, she gave me a bunch of filmmaking books and said, “If you want to do this, you have to study it and learn everything about it.”
From then on, my parents supported me. In fact, my whole family has supported me.
For many parents, the most important part of supporting a child’s passion is giving them a chance to figure out what that passion is. And often the hardest part is accepting it, even if it isn’t something you would have chosen. While he was still in high school, Jon started a video company, and by then his parents were behind him:
I’d shoot people’s weddings and bar mitzvahs. Customers from our restaurant would find out that Chef Chu’s youngest son wanted to make movies, and they would bring in beta computers to let me try. They weren’t interested in keeping the computers and would give them to me because they were nice, and they knew how much I wanted them. It’s also an indication of how supportive my parents are that so many of our customers would give me their slightly used computers.
In Outliers, Malcolm Gladwell argues that it takes ten thousand hours to become really accomplished at something. Jon, with all his experience making movies in high school, was a living example of the ten-thousand-hour rule:
By the time I went to USC film school, I was way ahead of the game.
My senior year, I shot a movie. Seventy people worked nonstop for ten days. I didn’t have the money to feed them, which you’re supposed to do during a film shoot. So my mom, my sister, and my sister-in-law drove to L.A. and cooked for all of us for ten days.
It was only a short film, but it changed my life. It had its public debut at the Tribeca Film Festival, and it got me an agent and a manager.
I invited my family to the premiere. My parents asked me what I’d be serving, and of course I had no idea. So my family got boxes and boxes of food and champagne, and they brought it to the theater, and they served it to everyone.
That’s the kind of support I always have from my family. To this day, everything I tell my parents, everyone in the restaurant will know tomorrow. They put posters of all my movies on the walls. And everyone knows if you bring in a movie ticket from one of my films, you’ll get a free drink at the bar.
And then Jon told me something I heard many other entrepreneurs say about their parents, in almost the same words:
I never worry about not working, or make a decision based on fear, because I know I have their support. Having that self-assurance means I have no fear, and so I can create what I want.
My parents’ whole life was to give to us, and they’ve had an amazing journey. They came here not speaking a word of English. They thought they could work hard and achieve the American dream, and they did. And their support and sacrifice allowed me to get into Hollywood with no connections.
I also talked with Jon’s mom, Ruth. She was one of the more involved moms I spoke with. Ruth had encouraged Jon’s passion with everything she had, even though filmmaking wasn’t necessarily what she’d had in mind for him:
I have antennae on top of my head. I always know what’s going on.
I always supported what Jon wanted to do. He was full of imagination. I have a clear picture of him at four years old, dreaming about something, telling fantasy stories, happy, singing the songs from Aladdin and The Lion King.
With school, sports, and music, he was really busy. Anything he wanted to do was okay with me, except when he played the CDs with bad words. That’s where I drew the line.
He never tried to do things the regular way, and I never tried to stop him. When he was eleven, he wanted to be in the Palo Alto Little Theatre production of Pacific Overtures. They said, “You have to send in a résumé.” He asked what that was, and I explained it was a piece of paper saying who he was. So he took a piece of paper and put his school picture on it and started drawing the Phantom of the Opera because he said that’s what he wanted to be when he grew up. Everyone laughed when they saw it at the audition, but he got the part. I went to the show for eleven performances.
Like most other parents, but especially because they’re immigrants, Jon’s parents wanted their son to have an even better life than theirs, but they never imagined it would be in film. Other parents might have told their son to put his camera away and focus on his schoolwork. But once Jon’s parents realized that film was his passion, they supported him completely. Getting him equipment and, later on, feeding his cast and crew were a big help, but the message Jon took from those efforts was even more important—he always knew his parents believed in him.
For some moms, the best way to provide support is to say, in effect, “I trust that you know what you’re doing, and I believe you can succeed at whatever you put your mind to.” In my interviews with entrepreneurs and their moms, I heard over and over that granting a child freedom and trust can be every bit as powerful as directly supporting a passion. That was the case with another USC-trained filmmaker, Jason Russell.
Jason, the second of Paul and Sheryl Russell’s four children, was born and raised in San Diego. He’s the family’s only entrepreneur. His brother and one of his sisters help run the Christian Youth Theatre, founded by their parents, now in forty cities. Another sister is a Hollywood hair stylist.
In 2003, with Bobby Bailey and Laren Poole, Jason visited Africa, and subsequently cofounded Invisible Children, a nonprofit advocacy organization created to stop Joseph Kony and his Lord’s Resistance Army (LRA) in Uganda from kidnapping children and forcing them to become soldiers. To this end, Invisible Children produced five hundred videos and twelve documentaries, all directed by Jason, including Kony 2012, which was intended to pressure the U.S. government to increase its efforts to capture Kony. With 83 million online views over a period of two weeks, Kony 2012 became the fastest-growing viral video of all time, and Invisible Children eventually became the largest youth movement in the world, with 3.4 million “likes” on Facebook, second only to the Olympics.
Jason told me he had always wanted to direct movies, but his earliest passion was directing plays:
I think because I was the second child, a lot of the pressure was taken off me. I grew up in a very fun atmosphere because my parents had started a children’s theater, and all our friends came through the theater. Our whole life was at rehearsals. We practically lived at the theater and, to this day, most of my closest friends are people I met there. I met my wife when I was seven and she was six, and we were dance partners.
From the time I was in eighth grade, I knew I wanted to be a movie director, and I knew I wanted to go to USC film school. So from the time I was fifteen, my dad let me help direct shows to gain experience. I did go to USC and majored in filmmaking. Jon Chu was my freshman roommate, and we took all our film classes together.
All the mothers I spoke with had in common their trust that their children would do the right thing. But there was a wide range in terms of how many rules their children were expected to follow. As Jason told me, his parents were stricter than others in some respects, yet in others they gave him an enormous amount of freedom:
When I was growing up, my parents were very traditional, and we had no TV in our home. Later we got one, but we could only watch on weekends. Otherwise, my parents kept it in the closet. This inspired us to make up our own games. We had to let our imaginations lead the way. I think this turned out to be important.
My parents were always very trusting. Their rule was you have to be home by midnight, but if you’re going to be home later, you have to call them. So that’s what I did. Usually, I was home by twelve o’clock, but sometimes I’d call and say, “I can’t be home until three o’clock tonight,” and they’d say okay.
I made them a promise when I was thirteen, and I got a promise ring. I promised I wouldn’t do drugs, drink, or have sex until I was twenty-one. And because I wanted to keep the promise, I didn’t do any of those. They trusted me to keep the promise. They never worried about me drinking at parties.
My parents were also always very strong communicating their values. It was never about grades or how much money you should make. They always told us, “Follow your dream. Find what you’re most passionate about. We just want you to do your best and be happy in the life you choose.”
I had a lot of freedom. If we wanted to go on a skateboard ramp or climb a tree, they would help. I think I had stitches at the hospital twelve different times. The day I turned sixteen, I got my driver’s license, and one week later I wanted to drive to L.A., and they let me. Shortly thereafter, I wanted to drive to Mexico with friends, and they let me. And then I wanted to spend time in New York with a friend, visiting my brother, and they let me. They trusted me, and I trusted them.
We would debate everything in a loving, healthy way. I felt I could tell my parents anything, and there was never any judgment.
Jason told me that the freedom his parents gave him also enabled him to go to Africa, which is how he ended up starting his nonprofit:
In 2000, I visited Africa with a friend and loved it. My mom was always supportive. Even when I told her I wanted to visit a war zone, she said, “You need to go. You need to fly. You need to follow your heart.”
After college, I bought a camera on eBay and asked a bunch of my friends to go back to Africa with me. Two said yes—Bobby Bailey and Laren Poole. While we were in Uganda, I met Jacob, one of the young boys who lived in terror that he’d be kidnapped by Joseph Kony’s Lord’s Resistance Army and forced to become a child soldier. I promised Jacob I’d do everything in my power to stop the war. That’s what I did. Kony is on the run. We won’t stop until he’s been caught.
I also talked to Jason’s parents, Sheryl and Paul. Here’s what Sheryl told me:
I have four kids, and they all have different personalities. We always told them, “Everyone can do something to make a difference in the world in their own way.”
From a young age, Jason had a tender heart for people less fortunate. We’d go to Mexico, and he’d see children on the street selling Chiclets, and he’d want to give them all his money.
When Jason was in fourth grade, he got paid for performing in a play. He took his money and bought a camera and started filming. He’s been doing it ever since.
We homeschooled each of our kids for two years, separately, when they were in seventh and eighth grade. That’s when their bodies and emotions changed, and we didn’t want them to feel peer pressure to take unsafe risks. They all went back to public school for high school. Jason used that opportunity when he was homeschooled to spend a lot of his extra time acting.
Obviously, Sheryl was willing to go to great lengths to keep her kids safe and healthy, which makes it all the more impressive that she continued to support Jason’s passion even when it led him to dangerous parts of the world:
When he was at USC film school, he went with a friend on a trip to Africa, and he knew he wanted to go back. So at graduation he said, “I want to do a documentary about the conflict in southern Sudan.” Even though it was a war zone, I felt if he wanted to go, he should. But I told him that first he had to do some groundwork and meet with different people so he would have contacts there. I talked to someone who gave him the name of an African woman who worked in a school in Uganda. So he and his friends went there, and she took them to northern Uganda, and that’s where he met Jacob and Invisible Children started.
In my conversations with entrepreneurs’ mothers, I discovered one reason why entrepreneurs are not afraid to fail—they don’t get punished for experimenting. What Sheryl told me reflected that approach:
When Jason was in sixth grade, he put soap bubbles in his aunt’s Jacuzzi. She was hysterical. I told her, “You’re going to look back on this someday and see him as a creative film director, not a hoodlum!”
We always say, “If you get an idea, you’ve got to try it.” We had a rule—to say yes as often as possible. Whatever their dreams were, or whatever they wanted to accomplish or wanted to try, as long as they weren’t putting themselves in harm’s way, we would say yes.
With his parents’ support for his passion from the time he was in the fourth grade, Jason was able to combine filmmaking with his wish to make the world a better place, and his efforts were instrumental in getting the U.S. military involved in the hunt for Joseph Kony.
Entrepreneurs tend to be ardent types, but not every future entrepreneur develops a single all-consuming passion at an early age. Lots of future founders move from one enthusiasm to another as they grow. This kind of restless curiosity is a common trait of people who go on to create their own paths in life. That’s why supporting exploration, including the possibility of false starts and detours, can be as valuable as supporting a child who’s already found a true calling.
I’ve known Joel since 2008, and he has a special place in my heart. Even though he’s the same age as my son Elliott, Joel had started a business much earlier. When Elliott wanted to invite eighteen young entrepreneurs to Utah to ski for a networking weekend, which later became Summit Series, he cold-called Joel, who was the first person to sign on. Joel’s also one of the nicest people I know. He sold half of his company, VideoBlocks, which sells stock video clips, for $10 million in 2012. His sister, who’s two years younger, is also an entrepreneur, with her own fashion business.
Joel was among a few entrepreneurs I spoke with who had a passion for selling things, as opposed to the thing itself. He was running little businesses from the time he was a toddler.
“I was three years old when I started selling gravel,” Joel said. “I would walk to people’s homes, take their gravel from their driveway, knock on their door, and try to sell it to them. People started calling me the Rock Man. It was crazy, but my folks were so supportive. They never said it was stupid. I loved selling things. My dad was probably standing behind me, passing my customers a dollar bill.”
His dad, Kent, is a lawyer; his mom, Judi, a contractor. When Joel was five, the family moved from the D.C. suburbs to southern Virginia. Every year for the next seven years, they would build a new house, move in, sell it, and then start building a new one. Joel acquired a strong work ethic at an early age; he and his sister were given the job of sweeping.
“We weren’t allowed to cut corners,” he said. “The floor had to be clean enough to eat off of. It taught me the value of hard work.”
Joel went on to tell me about the ventures that followed his stint as a door-to-door gravel vendor:
My next project was selling the little knickknacks I collected from our house. My dad went with me to the local community store and convinced them to let me sit out front and sell them.
By the time I was eight, we lived near a golf course, and I knew where all the old golf balls would be at the end of the day. I would collect them, clean them up, put them in egg cartons, go to the parking lot where the golfers parked, and try to sell them.
Then I decided it wasn’t scalable, and I wanted to be able to sell even when I wasn’t there. So I took my little red wagon and made a sign that said JOEL’S GOLF BALLS. Then I made another sign that said HONOR SYSTEM: 3 BALLS FOR $2 and set out a Pringles can for the money. The can got stolen, so that’s how I learned to protect my assets. I got a mailbox with a lock on it and put the sign on that.
I left the wagon at a spot after the ninth tee. I would go every night and collect my money, usually $20 a day. It was $10 for a sleeve of three new balls at the pro shop, but my used ones were only $2 for a sleeve. People loved it, but the pro shop got upset and took my wagon. My dad was furious. He went over there with me and made them give me back my wagon. After that, I got a big chain and lock and tied my wagon to a tree.
I clearly remember the first time I heard the word “entrepreneur.” I was on the tenth tee and heard some guys talking. One said, “That kid’s an entrepreneur.” I thought it was a curse word. I ran home and asked my mom, who told me what it meant. I was eleven. I loved that word!
Because Joel had always been encouraged to pursue his interests to the fullest, he was ready to pounce when something new came into his life, and he quickly combined a couple of his passions into a business venture:
When I was twelve—it was in 1997—I got my first computer. It blew my mind! Suddenly I could sell my golf balls to the world, and nobody knew how old I was.
I found eBay. I was big on Hot Wheels cars at the time. I started asking around, and I discovered there was no system to keep track of them. I found a guy who had designed software to manage inventory. I paid him $1,000 to repurpose the software so people could use it to manage hobbies and collections. Before I was thirteen, I was a PowerSeller on eBay, selling thousands of dollars a month of the software.
Nobody knew my age. I realized how powerful it was to be anonymous on the Internet. I had over two thousand transactions with positive ratings. My parents were very supportive. They would drive me to the post office to pick up checks and then drive me to the bank. They never questioned how I was spending my time.
Although Joel stumbled into his next venture, it led to what he does today:
When I was in eighth grade, we took a family trip to Hawaii. I had bought myself a video camera because I thought Hawaii would be so relaxing, and I wanted to share that.
So I took some footage. My ever-supportive parents let me shoot the video, even though it must have seemed ridiculous.
I found a guy who’d made a CD of Hawaiian luau music. I paid him for the rights to the songs. I brought home a couple of trash bags filled with sand and made a Hawaii relaxation video, with scenes of beaches and sunsets, and the luau background music.
I sold the videos on eBay along with little bags of sand. The amazing thing is that it really got me into video, which ended up being my business. I also decided that people would buy anything.
And then Joel told me a story that shows how mastering something often leads to noticing what’s missing, a discovery that can be the basis for a company. He was in high school and was interested in technology, video, and sales, but when he sought advice from his guidance counselor about whether to plan for a career in journalism or business, he wasn’t able to get satisfactory advice. So he approached Kidz Online, an educational nonprofit, and asked for financial backing to conduct videotaped interviews with top performers in various fields.
Over the next two years, he shot 150 interviews with CEOs and VIPs all over the country, including one in 2003 with Arnold Schwarzenegger, who had just announced that he would be running for governor of California. Joel found the interview interesting, but he realized it was visually boring. He asked himself how the Discovery Channel managed to make such arresting videos; it dawned on him that a captivating video requires more than a talking head:
I decided I needed shots of the Hollywood sign and other interesting visual things. But they were cost-prohibitive. And that was my Aha! moment. I realized if I needed this stock footage, others would need it, too. I took some of my savings and purchased a good video camera. I started shooting footage of Washington, D.C. I put it on eBay. People started buying it. I did this all through high school.
Joel’s realization about how to improve his work hadn’t come about as a direct result of his shooting Hawaiian relaxation videos—but that’s the point. Because his parents encouraged him to pursue his interests even when his activities didn’t have a clear reward, they made it possible for him to make the discovery that launched his career.
Some parents resist the idea of following a child’s lead. They think it means simply being permissive or letting a kid run wild. But Joel, like a lot of the entrepreneurs I talked with, described a balance between firmly established parental expectations and the freedom to pursue individual interests:
My parents definitely had rules. They made me learn how to type and wouldn’t let me hunt and peck. They said I could only watch TV on the weekends. And I couldn’t play video games.
My parents also taught me the value of money. I had $2 a week allowance. I wanted a remote-control car, but it cost $20. They told me I’d have to save up for it. Everyone else at school had Rollerblades, and my parents wouldn’t buy them for me. They said, “If you want them, you have to save your money.” It made me angry at the time, but it really made me appreciate the value of money.
My parents didn’t pay for college. I went to Babson on student loans and from the money I was making running my company. And because I paid for college, I never missed a class. I’d calculated the cost of each class at $500. If I was tempted to skip a class, I always thought, There is nothing I could possibly do during this hour that’s worth more than $500.
Joel’s parents also supported him in his academic choices, even when those choices weren’t the ones they would have made for him:
When I applied to college, I knew I only wanted to go to Babson because I’d read it was the best program for entrepreneurs. Then I decided I wanted to defer my acceptance for a year, to build my business. Again, my parents were supportive, even though it was a big ask. I had never been a normal kid, and they’d always agreed with what I wanted, but I knew they were really excited that I’d been accepted by my first choice and that I was going to college. When I broached taking a year off, they said, “We’ve always supported what you want, and we’re not going to change now.” It was very liberating.
So that’s how I spent the year. In 2003, right after high school graduation, I took the year off and really launched Footage Firm. I’d go to a city, film it, go home, edit it, put it on eBay, make some money, buy a ticket to the next city, and start again. I did this thirty times.
After that year, I went to Babson to learn more about business. Because of my company, my education was much less abstract—when I studied accounting, marketing, and finance, they were directly applicable to what I was doing with Footage Firm. And after class, I’d go back to my room and work on my business, filling orders and selling film footage.
In 2007, when Joel was twenty-two, the Small Business Administration voted him Young Entrepreneur of the Year in recognition of Footage Firm. In the same year, he was included in Business Week’s “25 Under 25” list. Also that year, the summer before his senior year, he worked for an investment bank. At the end of that summer, he received an offer for a six-figure job that would begin a year later, after his graduation from Babson:
I had to decide whether to take that offer or move back home with my parents and build my business.
Again, my parents were supportive. They told me, “If you think this is what you want to do, you should do it.”
Some of my friends told me I was an idiot to consider turning down that offer. They said, “Only one out of ten businesses succeeds!”
I looked at the worst-case scenario and decided if I could get a job offer once, I could probably get a job offer twice.
A chance encounter with my son Elliott helped him choose.
I was still trying to decide in April 2008, a few months before I graduated, when Elliott Bisnow called to invite me on the first Summit trip. I really appreciated the support my parents had given me. So when Elliott said he was going to put together this group of young entrepreneurs, I didn’t think he’d pull it off, but I said yes because I loved his passion. And he did pull it off. So I went to Utah. There were eighteen of us, each under thirty years old. It was the first time I’d spent so much time with other young entrepreneurs like me.
After that, there was no turning back. It really solidified my decision. I was so inspired after meeting the other young entrepreneurs at Summit that I decided to take a year to try to start a multimillion-dollar business. I turned down the investment bank.
My classmates thought I was out of my mind. But I was determined to prove them wrong, and so I worked like crazy.
It turned out Joel made the right decision. In 2013, he was named to Inc. magazine’s list of “30 Under 30” for disrupting the stock footage industry with a Netflix-like subscription model.
Joel is still working at his company, renamed VideoBlocks, which has more than ninety thousand customers for its stock video clips. He’s working to make his business worth even more, and his parents are still supportive.
Paige Mycoskie is the creator of Aviator Nation, a popular line of vintage-style clothing (we’ll meet her brother, TOMS founder Blake Mycoskie, later). When I talked with Paige’s mother, Pam, she told me that while growing up in Texas, Paige had always been really creative and loved art of any kind.
“Whenever I took her to the toy store,” Pam said, “she always chose art supplies. She drew rainbows and hearts when she was a little girl, and that’s where the stripes came from on some of her clothes, especially the kids’ line.”
In 2006, when Paige was in her mid-twenties, both sets of grandparents gave her $100 apiece for her birthday, and she told Pam that she was going to take that $200, buy a used sewing machine, and fulfill her dream of starting a clothing company. At the time, according to Pam, Paige didn’t even know how to sew, but she returned home to Texas from the apartment she’d been renting in California, and she brought her sewing machine with her, saying, “I’m just going to stay home for a couple months to sew.”
Paige sewed almost nonstop for three months, “working long hours every day,” Pam recalled. “She started making her own patterns, cutting things, sewing things on T-shirts. She made fifty garments.”
How many other parents would have been excited to see their twenty-something daughter move back into the family home to teach herself how to sew? But Pam went out of her way to help Paige pursue her dream.
After Paige had sewn enough garments, Pam drove back with her to Los Angeles and helped her find a place to live. When Paige brought her fifty garments to Fred Segal, a high-end store with a fashion-forward clientele, the store’s buyer took them all.
Three years later, Paige opened her first store on Abbot Kinney, a trendy street in the Venice area of L.A. She now has five stores selling her surfing-inspired clothes and is negotiating to open several more. Her clothing line is also in Bloomingdale’s, and she designed a special line for the Gap. In 2013, GQ magazine named Paige among the year’s best new menswear designers.
UnderArmour founder Kevin Plank grew up in Kensington, Maryland, a D.C. suburb with a small-town feel. Kevin was the youngest of five boys who spanned thirteen years. His mom, Jayne, worked full time. She was the first woman elected to the Kensington City Council, and later she became the city’s first female mayor. After fifteen years with the city, she went to work in the State Department during the Reagan administration, when Kevin was eleven.
Jayne told me that the family’s life was often “chaos,” but she tried to spend special time alone with each of the boys on a regular basis. She trusted all five of them to choose what they wanted to do, and she supported them in whatever choices they made.
“They all had very different interests,” she said, “and they all found their passions.”
Because Kevin was the youngest, he traveled with his mom to work-related conferences, and helped her with her inaugurals—and he knew she valued his assistance. As he grew older, since she had already become so busy by the time he came along, Jayne trusted him with even more freedom than she’d given his older brothers.
“We didn’t organize our kids’ time,” she said. “They went over to their friends’ homes or hung out at the park across the street. I gave them quarters so they could turn on the lights at the basketball court to keep playing after it got dark. And they’d bike downtown to get their hair cut.”
All the boys loved sports:
Boys playing sports, working hard, with a coach looking out for them, is the best. But all of my boys pursued different sports. I always let them determine their own goals. One quit school for a while. I said that was fine. I agreed he shouldn’t be in college until he figured out what he wanted to do.
While Kevin was in college, his father died. In five years, Kevin also lost three grandparents. It was a rough period for everyone in the family, but Jayne, with her characteristic ebullience, said her motto became, “Embrace adversity and get over it.”
Jayne gave all the boys freedom to choose what they wanted to do, and supported them in whatever choices they made. She told me that Kevin had always figured out how to make his own way in life, and she thought that was great. Today, Bill, the oldest, is a builder who also runs martial arts schools; Stuart is a developer and high school football coach; Scott is a real estate developer; Colin is a movie producer and writer; and Kevin, the baby, runs one of the largest athletic apparel companies in the world.
Kevin was especially passionate about football. At the University of Maryland, he started playing without a football scholarship, but worked hard enough to earn one, becoming special teams captain.
“You know what D.C. is like in August,” Jayne said. “You don’t perspire. You sweat!”
And Kevin got tired of sweating through his cotton T-shirts during his twice-a-day summer football practices. He’d had a little T-shirt company when he was in high school—he and his friends would tie-dye shirts on the back patio and then sell them at football games and music festivals. So he decided to find a fabric that his skin could breathe through; he drove to all the fabric manufacturers he could find, first in Baltimore and then in New York.
He worked all the time, Jayne told me. He had been driven from the time he was young to make his own way. “His education was an inconvenience on his continuum to success,” she said.
Kevin launched UnderArmour from his family’s basement. It’s now a multibillion-dollar company, one of the largest sellers of sportswear in the U.S., and has transformed what athletes wear.
The outcome of all that trust in Kevin and his brothers, Jayne told me, is that “they got over their humps and bumps on their own and all became successful. Being proud of my children’s success is the best reward. I’m very fortunate.”
Alexis Jones is a thought leader of the women’s movement, an expert on Generation Y, and the founder of I AM THAT GIRL, an online empowerment community for young women, with 150 local chapters and over 250,000 members. Alexis has spoken to more than 100,000 young people in person and reached more than five million online. When I talked with her, she told me what her mother, Claudia Mann, helped her learn:
I was taught really young that it’s good to make mistakes. Every time I messed up, my mom would say, “That’s awesome. What did you learn? It’s not real life to think there’s one right answer and one wrong answer. It’s easy never to step out of your comfort zone, and it’s easy to not fail.” My mom taught me that if you can learn from your mistakes, you’re on a completely different track.
My mom’s only rule was “Don’t ever lie to me.” She told me, “Don’t underestimate what I can handle. Talk to me.” So there was no need to be rebellious. She trusted me to make good decisions. She told me, “These are your freedoms, as long as you keep up your end of the bargain—getting good grades and getting a scholarship.” Mom would say, “I trust you,” and that was huge. I didn’t want to screw that up. My girlfriends were all lying to their parents. I didn’t have to.
Kids will meet expectations. Even when I was twelve, Mom would say, “Let’s negotiate. Tell me what you want.” I thought it was so cool that I had a say and that I got to participate.
I think things are different for girls. There are a lot of intangibles we need to know, like learning to communicate very directly, and even little things, like shaking hands, looking people in the eye.
I have four brothers, and my mom was always fighting for me to have more independence. My parents were divorced, and my dad was more protective. When I was nineteen, I spent the summer traveling alone in Europe. My mom said, “I think it’s time for her to have an adventure.” My dad said, “What are you doing?”
Like many budding entrepreneurs, Alexis pursued a number of passions until one really clicked:
I started modeling when I was thirteen. My mom said, “We’ll do this as long as it’s fun.” My mom never put a focus on how I looked. She always said, “Pretty doesn’t pay the bills.” If someone said, “She’s so cute,” my mom would say, “Yes, but she’s also very smart.” I got on the cover of a magazine, and when I showed her, she said, “Great. Did you finish your calculus?” She always kept it in perspective. She told my brothers and me the most important thing that people could say about us was that we’re kind. If I got a compliment, she always said, “Thanks, but my kids are great human beings, and that’s what’s important.”
Sports were huge for me all through high school. I played volleyball and soccer. Eventually the modeling agency wanted me to give up sports to concentrate on modeling. They told me I was looking too strong.
I asked my mom what I should do, and she said, “Whatever you want. You choose.” I chose sports. She said, “Great.”
I was good in sports, but not great. And modeling was an avenue, not a passion.
I told the director of the modeling agency, “I’d rather be smart than pretty, and I want to go to college.” And he said, “You are wasting your prettiness. Get out of my office.”
I was also a camp counselor in the summers, and I loved telling stories by the campfire. Standing up and telling stories—that was a place where I shined in a way I didn’t shine in other areas. My mom wanted me to try everything. And once I tried storytelling, and then writing, it was all over—I knew I’d found what I loved. Which led to acting, which led to my public speaking today. One passion led naturally to the next.
For Claudia, supporting her daughter’s sense of freedom and choice never meant supporting laziness or a lack of focus. Alexis learned to work hard, like all the other entrepreneurs I talked with:
I was raised with a strong work ethic. I worked for a while in the entertainment industry. When I auditioned for a role, I’d tell them, “You can find prettier, you can find thinner, you can find more experience, but you will never find someone who works harder than me. I will be the first one here and the last one to go home.”
I got cast for everything. My mom told me, “Put yourself in a race where nobody can compete with you.” I took that advice. By sticking with activities I loved and working harder than anybody, I’ve been fortunate to achieve a lot of success.
My dream was to go to college, but we couldn’t afford it. My mom said, “Never use a lack of money to walk away from your dreams. If you want it, make it happen.” She told me, “Not having money is a terrible excuse for not following your dreams.” Whenever I said, “I don’t have something,” my mom said, “Then go make it.”
Alexis’s mom supported her daughter in her chosen pursuits, from sports to modeling to storytelling to acting and finally to public speaking. She let Alexis choose her own path and make her own decisions, had confidence in her, supported everything Alexis wanted to do, and taught her daughter that financial limitations should not stand in the way of reaching for her dreams.
As we just saw in the story of Alexis Jones, parents can greatly influence their children’s attitudes toward work. Many parents, aware of this responsibility, put a lot of effort, not to mention anxiety, into making sure their kids get the right messages. But in my interviews with entrepreneurs and their moms, I found that often the parents who made the deepest impressions were not those who constantly talked to their children about the importance of finding meaningful work, or who arranged their lives to accommodate their children’s passions. In many cases, the deepest impressions were made by parents who took a more subtle approach of recognizing what their children wanted to do and giving them the space to do it.
I’ve known Wendell Gunn for decades; we worked in government together thirty years ago. I spoke to his wife Linda about their son Greg, a Rhodes Scholar and one of the country’s most successful African American tech entrepreneurs, who built and sold his educational software company, Wireless Generation, for $450 million.
Greg started to read when he was four years old. According to his mom, Linda, he also always liked math and computers:
When Greg was only eight, and the first Apple computer came out, Greg insisted we get one. From then on, he learned about computers on his own, writing programs.
It may sound like a small thing, but when Linda and Wendell bought that computer, they didn’t just give Greg a tool he could use to explore his passion. They also showed him they would provide tools he needed to advance his skills. Sometimes that meant letting him assemble Legos and play video games, even when other parents saw those activities as a waste of time.
As Linda also told me:
Greg was always a leader. The other two kids weren’t like that; he just seemed to be born that way. All the neighborhood kids would defer to him when they played games. I didn’t raise Greg to be an entrepreneur; our kids have always done the leading, and we did the following; we support them in what they want to do.
It’s true that Greg is the oldest, and was an “only” until he was five. When there weren’t a lot of kids around, he spent his time mostly with adults. He also had strong internal motivation, a gift he seemed to come by naturally. His younger brother now works with him and his sister is pursuing her dream, poetry. According to Linda, he showed great grit and determination in whatever he was doing:
In high school, Greg wanted to get a well-rounded education, and he also started running track. He previously hadn’t been interested in sports. Even though he wasn’t a superstar, he always wanted to do his personal best in everything.
Apart from computers, Greg had another great passion—education. In high school, he had a tutoring program to work with kids who were struggling in math. After graduating from the University of Chicago with a degree in physics, he took a gap year and taught in a tech-intensive magnet school.
After going to Oxford University as a Rhodes Scholar, he went on to MIT for an MBA and a master’s degree in computer science, and started thinking about how to combine his two loves: education and computers.
With a friend he’d met at Oxford, Greg cofounded Wireless Generation, an educational software company that provides assessment and instructional products for three million children. After he sold Wireless Gen, he was named Entrepreneur in Residence at City Light, a venture capital firm that invests in high-growth U.S. companies.
Linda and Wendell Gunn had no idea their son would grow up to be an entrepreneur. But by supporting him wherever his interests led him, they left him free to pursue his passion to unexpected heights.
Robert Stephens founded Geek Squad twenty years ago in Minneapolis. He was twenty-four, and he had a bicycle, a white shirt with a nerdy black clip-on tie, and $200 of start-up capital. He built Geek Squad into a global brand with 20,000 employees and, after ten years, he merged the company with Best Buy, staying on for two years as chief technology officer before leaving to pursue new ventures.
The child of Depression-era parents, he grew up outside Chicago, the youngest of seven. His mom married at fifteen (she told his dad she was sixteen) and started having kids immediately. Robert is the youngest by five years, and he’s the only one to go to college. His siblings include a bricklayer, a mechanic, and a truck driver. His dad spent twenty years in the Navy. Robert told me that he and his six siblings never wanted for anything, but they definitely weren’t spoiled.
I find it fascinating that most of the entrepreneurs I talked with told me that their place in the birth order, whatever it was—oldest, youngest, somewhere in the middle—had contributed to their independence. Wherever they were in the family, and regardless of how many siblings they had, they thought their situation was perfect. As the youngest, Robert thought his parents had loosened up enough by the time he was born to give him more independence than they had given the others. They were the opposite of helicopter parents. He could build a raft, float down a creek, and come home in time for dinner with no questions asked.
Unlike other entrepreneurs I talked with, Robert had a passion for fixing things as he was growing up:
When I was three years old, I took off all the doorknobs in the house. When my parents saw me, I had them laid out neatly on the table, all organized—doorknob, screw, doorknob, screw. My parents weren’t angry, though they did tell me to put them all back.
This became part of our family mythology. I was the fix-it guy. That’s who I was—“Robert can fix anything.” It gave me a sense of pride and self-esteem. I loved taking things apart, finding out how things worked. I took apart a radio. I really could fix anything.
When I was twelve, I had a job repairing TVs in the neighborhood. Back then, lots of people had a fear of technology, but I didn’t.
My parents got me a chemistry set and a lot of Lego sets. I spent a lot of time alone, in creative play, building rockets or making the sandbox whatever I wanted it to be.
Looking back, I think my parents were very thoughtful about how they supported me. I think that’s key—recognizing and allowing my essential personality to emerge, and then giving me room to develop. I had freedom, but with fences. And my parents were always okay with whatever I wanted to do: “Sure, I’ll drive you to computer club.”
I was a really fast typist, so in high school I typed papers for people. I charged $20 per paper, and $25 with a bibliography. Then I started offering to write the papers also, for $45. I was making $250 a week. I kept a database, tracked the grades, rewrote papers to turn a B into an A. I did this for three years. My dad said, “This isn’t ethical.” I said, “I’m not cheating. They are.”
Then I typed up Rolodexes for businesses like beauty salons and hardware stores and sent out cards for them. They didn’t have an organized database. When I was seventeen, I got a job delivering mattresses. Then I built a database and a tracking program for them on my Commodore computer because there was no computer system. That was my pattern—I’d get a menial job, and then I’d start organizing it better. And then I started repairing computers.
Robert Stephens is a classic example of someone who turns a childhood passion into entrepreneurial success: the boy who loved to fix things started a company that fixes things. His parents consistently supported his passion and trusted him to make his own choices, and he learned to believe in his own abilities. And when he was ready, the fix-it guy made his entrepreneurial dreams real.
Each of the entrepreneurs profiled in this chapter grew up in a home where parents supported their passion. That might sound simple, but it’s not as easy as you might think, and it’s also not as common. In ways large and small, supporting a child’s passion means letting the child take the lead in her own life. This is hard for parents! We know so much more than our children do about the world and how it works, right? And besides, we want to shield them from making mistakes or getting hurt. So we give them advice that we think will help them in their journey: help them get into the right college, help them get a career where they can support themselves. But our desire to help, based on our knowledge of how the world worked when we were growing up, may backfire if it prevents our kids from spending time on something they love.
So there comes a point when “supporting” your child means “stepping back.” I’ll end this chapter with some things I learned from writing this book about my own experience, as our two boys grew up and became who they are today.
Each of our sons had a passion outside school while they were in high school and college. And although I didn’t realize it at the time, there was a serendipitous aspect to Elliott’s playing competitive tennis and Austin’s writing music. It was only when I started to speak to the moms of successful entrepreneurs that it hit me: both of them had passions in areas that my husband and I knew nothing about.
If they had been interested in politics or media or law or economics—areas in which my husband and I had worked—we would have gotten involved. We would have tried to help and offered advice. But we knew almost nothing about tennis or music. So Elliott had to decide without help from us where to train, which coach to work with, what racquet to use, what tournaments to enter. Austin had to decide without our advice what instruments to learn, who his piano, guitar, drums, and voice coaches would be, what music software to get, what microphone and mixer to buy, what songs should be on his album, and what producer to work with.
And that was a good thing. They had to take control, make decisions, figure it out for themselves. It wasn’t a conscious decision on our part, but looking back, it was lucky that it worked out that way. I didn’t know it at the time, but now I know that all children should be allowed to figure out their own passion, that parents should nourish and support and encourage that passion, and that parents should largely stay out of the way so that it becomes truly theirs.