I almost called this rule “Let Your Child Play Sports” because sports had a role in the lives of so many of the entrepreneurs I interviewed for this book. Sports can be crucial to developing an entrepreneurial mind-set. That’s because kids who play sports learn how to compete, which also means learning how to lose and learning how to pick themselves up again—lessons that can be transferred to competing in business. Whatever sport your child plays, whether a team sport like basketball or an individual sport like tennis, it must be one your child loves.
And if your kid hates sports, that’s not a problem. Lots of other activities will teach her to compete, strive for success, win, and lose. Just make sure the activity is the child’s choice, not yours. You can advise your child on the pros and cons of a particular activity, but it must be your daughter’s passion that drives her; it must be your son’s choice to commit himself. A friend whose son is a serious chess player told me how he’d battled through an epic four-hour match only to lose at the end, and what he’d learned from it, and how he vowed he’d never lose to that guy again. So these lessons don’t only come from sports. Any passionate pursuit that involves competition—playing chess, auditioning for roles in plays, submitting watercolors to juried exhibitions, participating in spelling bees—forces a young person to be tested on a regular basis.
The key is learning to compete, to fight to succeed, to learn how to win, and to learn how to lose. Much has been written on how the lives of economically disadvantaged children have been transformed through chess. University of Maryland Baltimore County President Freeman Hrabowski famously turned his largely African American commuter school into the nation’s top chess powerhouse.
And much has been written about an impoverished New York City middle school, IS318, whose kids beat all the top private schools in the country in the national chess championships. As their coach Elizabeth Spiegel explains in Paul Tough’s How Children Succeed, young people grow when they can take responsibility for their mistakes and learn from them without obsessing or beating themselves up.
She says, “[W]hen they lose a chess game, they know that they have no one to blame but themselves…you have to find a way to separate yourself from your mistakes or your losses. I try to teach my students that losing is something you do, not something you are” (Tough 2012, 115–116).
Steve Jobs talked about learning from failure in his famous 2005 commencement address at Stanford. He described his greatest failure, being fired from Apple, the company he had founded, just after he turned thirty. And how that failure led him to reorient himself, be brought back to Apple, and turn it into one of the world’s most transformative companies.
How Children Succeed also quotes Dominic Randolph, head of the prestigious private New York Riverdale Country School, about the mistake many parents make in preventing their kids from failing. Randolph makes “a persuasive case that failure—or at least the real risk of failure—could often be a crucial step on the road to success.” He worried that “his mostly affluent students…were being short-changed by their families and their school and even their culture by not being given enough genuine opportunities to overcome adversity and thus develop their character. The idea of building grit and building self-control is that you get that through failure… . And in most highly academic environments in the United States, no one fails anything” (Tough 2012, 177).
Though kids can learn about competing through many different channels, in this chapter I’m going to concentrate on sports. Many of these entrepreneurs played sports competitively through high school, and a surprising number continued in college. Their moms were like me—they didn’t have their kids play sports to learn skills that would help them when they started companies or nonprofits—but looking back, we all realize that perhaps one reason our kids became entrepreneurs is that learning to compete in sports helped them understand how to compete in business.
Also—and this is really important—this is not about being a star athlete, or even a good or natural one. It’s about learning to compete and learning to deal with setbacks. I remember speaking to a loving mom who worried because her daughter enjoyed sports, loved being part of a team, but wasn’t particularly athletic. She had gone to a baseball camp the summer before, and had spent a lot of time warming the bench.
Remarkably, in the last game of the summer, deciding the county championship, her daughter came up to the plate with the game tied in the ninth inning. The bases were loaded, with two outs. Her mom gulped. Her daughter swung—and got a hit, winning the game for the team.
She wanted to go back to baseball camp the next summer, but her mom wanted to protect her from disappointment. “I told her, ‘Don’t go back. You will never repeat that moment.’ ” She worried her daughter could never live up to the expectations that dramatic hit sparked: “I told her to quit while she’s ahead. Why should she go back to camp and do worse than she did the summer before?”
This mom loved her daughter so much and wanted to protect her from getting hurt, but I wondered what message that would send. Not to follow your dream? Not to try? That failure is bad? That not trying is better? There was risk in her daughter returning to camp, but so much opportunity for growth—and for grit.
Another lesson children learn when they play competitive sports is the direct connection between hard work and results. Getting this connection leads to what psychologists call grit.
University of Pennsylvania psychology professor Angela Lee Duckworth studies what leads to success. She has popularized the concept of grit, which she defines as “passion plus perseverance toward long-term goals” or, in other words, working really hard to make dreams a reality. She studied West Point cadets, national spelling bee champs, effective teachers, business leaders, at-risk school kids, and Ivy League undergrads, and in all of them she found that grit is the best predictor of success. More important than IQ. More important than talent. More important than family income. More important than social intelligence, or good looks, or health. She says grit is living life like it’s a marathon, not a sprint. It’s having stamina. It’s sticking with your goals day in and day out, not just for a week or a month.
One of the entrepreneurs I interviewed has a particular interest in Angela Duckworth’s work on grit. Chris Wink cofounded the Blue Man Group in 1988 with his friends Matt Goldman and Phil Stanton after their small shows on Manhattan city streets got noticed. The troupe has been playing to packed audiences around the world since then and is now a global entertainment company with ongoing theatrical productions in Las Vegas, Orlando, Boston, Chicago, New York, and Berlin. In 2011, BMG won the Off Broadway Alliance Audience Choice Award for best long-running show. Chris is also one of the co-founders of the Blue School.
Chris is passionate about innovation and creativity. He invited Angela Lee Duckworth to his school to talk about grit. When I asked him about it, he told me: “Grit was one of the topics we were interested in trying to teach at the Blue School. It also resonated with our own experience of having to work incredibly hard to make our show successful. The question is, is grit teachable? Or do some people just have it? Well, one thing is certain, you won’t have it if you pursue things you aren’t passionate about. People said I was lazy when I was doing stuff I didn’t like. But when it comes to building cool shows, I’m an unstoppable force. I’m not saying all my ideas are good, I’m just saying I can’t be stopped.”
Kids with grit succeed, and all successful entrepreneurs have grit. People with grit learn that when they invest effort in something, they will see success. For many high achievers in careers such as medicine, law, and investment banking, that lesson is learned in school. Their hard work yields obvious rewards, enabling them to climb to the next level. To use the example of future doctors, the top high school students get into the top colleges, and then into the top medical schools, and then get the top internships and the top residencies, before getting positions at the top hospitals.
But many future entrepreneurs, especially those who aren’t fully engaged by school, first learn about the power of grit on the playing field. Perhaps it’s because they played sports, or perhaps it’s just common to the current generation of young people, but it seems they all keep score. They want to know if they’ve won or lost. They’re achievement-oriented, and they determine achievement by metrics. That’s true even for those who don’t seem to invest much effort in getting good grades. They all want to win: some at school, some on the playing field, and some performing. Benny Blanco, the songwriter we’ll meet in the next chapter, wanted to win rap battles, not spelling bees. The common denominator: if it’s something they care passionately about, they want to be the best at it.
In business, “the best” is often measured by money. The money is a scorecard; entrepreneurs tend to value it because it measures their success in business, rather than for what it can purchase. For the entrepreneurs I talked to, the money’s not the goal: it’s a marker for winning, creating, accomplishing, succeeding, building. For entrepreneurs who started nonprofits, money’s important inasmuch as it lets them help people and transform communities—the real fruits of success.
That drive yields much more than the momentary joy of victory. We’re so busy protecting kids from failure that they don’t learn to compete with intensity, which builds character. We’ve become the country where everyone gets a trophy regardless of effort.
Riverdale Headmaster Dominic Randolph says, “[T]here was always this idea in America that if you worked hard and you showed real grit, that you could be successful… Strangely, we’ve now forgotten that. People who have an easy time of things…I worry that those people get feedback that everything they’re doing is great. And I think as a result, we are actually setting them up for long-term failure” (Tough 2012, 56).
How can we raise our kids with grit—teach them a work ethic, keep them motivated for the long run? I think it has to do with letting them pursue something they love. If they love it, they’ll work hard. If they work hard, they’ll keep trying, despite failures, and they’ll eventually succeed. If they see the connection between hard work and success in one part of their life, it can translate into hard work, and a willingness to fight past setbacks, for a different activity when they get older.
For another angle on the way kids learn from failure, I look to the work of Stanford professor Carol Dweck (2008). She studied four hundred fifth graders who took three tests, one of which was so difficult that they all failed. She found that those kids who had been praised for their effort recovered enough that by the next test they scored 30 percent higher, while kids who had been praised for their intelligence scored 20 percent lower. She concludes that when you praise kids for qualities they can control, like effort, they learn to work harder than those who are praised for just being smart. In other words, kids who are praised for their brainpower might think that hard work isn’t necessary. Kids praised for hard work—by their parents or their coach or their music teacher—learn to work hard and to understand that they can learn and grow from failure.
Simon Isaacs describes his work as “positive social disruption.”
He climbed Mt. Kilimanjaro with a team of celebrities and global influencers to raise awareness of the need for clean water around the world. He worked to bring attention to Malala Yousafzai, the young Nobel Peace Prize recipient from Pakistan who was shot for her advocacy of education for girls. He led the Clinton Foundation’s work on agriculture and safe water in Rwanda. He founded GATHER, a company that builds large-scale nonprofit organizations or campaigns, often with funding from the Gates Foundation, and with focuses like nutrition and voting.
When I met him, we started talking about the influence of sports on kids who become entrepreneurs. I asked him if he had played a sport when he was younger. He said, “Oh, yes, I was an All-American skier on the Olympic Development Team.”
From the time he was six, Simon lived in the Vermont woods with his parents, Lisa and Henry (both artists) and his two sisters. His mom started a design agency, and she and his dad built a house that included an office and studio space.
Simon began cross-country skiing, and he started racing when he was eight. He was good enough to become an Olympics hopeful on the U.S. Development Team. “Between the ages of ten and fifteen,” he told me, “I was skiing six days a week—Nordic combined, which is both cross-country and jumping. I trained at the Olympic Center in Lake Placid during the summers. At fifteen, I decided to focus on cross-country—it was really my life.”
But for all his joy in skiing, Simon also knew great sorrow from an early age:
My mom was diagnosed with cancer when I was ten. She died when I was eighteen. My dad was also sick. But they both worked really hard to be there for us as much as they could. The illnesses would come and go, and whenever they could, they were there and involved. But there were also times we were alone. Looking back, I’m amazed how involved they were in our lives, in our school, going to my ski races, while all this was happening.
Throughout this time, with the help and mentorship of his uncle, Simon continued skiing. He spent his final two years of high school in Colorado; after high school, he went to Middlebury College, where he raced and even spent a semester training with the Italian national team. He also graduated second in his class. “I was a real nerd,” he told me.
As much as Simon loved skiing, he eventually decided that he wanted to do something different with his life. But he told me that devoting so much time to an individual sport had taught him three lessons, which he uses today as an entrepreneur:
First, you have a constant feedback loop—understanding your body, your fitness, your shape, your technique, your heart rate. You’re always trying to figure out how you can improve. I’m still that way today. I’m always looking at myself, analyzing myself, trying to evaluate myself from that perspective. I’m always asking myself, How did that meeting go? How can I be better?
The second lesson is, how do you manage defeat when you aren’t winning? How do you get yourself back up the next day, get back to the starting line and begin again? You’re not going to nail everything, so you have to view the journey as one long race. I’ve had a lot of disappointments, but I look at it as one big feedback loop, and I just say to myself, How do I get back up on my feet? I’ve learned it’s not a defeat. It’s part of the learning curve, part of the process.
The third lesson I learned is always to survey the course before the race. Before I started, I was constantly thinking, Where is everyone else going to slow down? What stretch am I going to turn this on? I’ve always done this throughout my career, tried to figure it out in advance: Where am I going to be able to stand out? Every good entrepreneur surveys the landscape, and the market, and asks, “Where is the opportunity?”
In addition to running GATHER, Simon recently launched a media company and a nonprofit incubator that will provide funding to fledgling nonprofits for space, public relations, media, and operational costs. He also cofounded Fatherly, a parenting resource in the dad space. “Because of how intense my life was when I was competing,” he said, “it’s very normal to do all this stuff, to keep this busy, and to stay on top of everything.”
Adam Braun started one of the country’s top nonprofits, Pencils of Promise, which is building hundreds of schools around the world. His older brother Scott, called Scooter, is one of the top talent managers in the country. He discovered Justin Bieber and Ariana Grande, owns a record label, a publishing company, a management company, and a tech incubator. Their sister, Liza, is a physician.
I talked with their mother, Susan, an orthodontist, to learn how she had raised two successful entrepreneurs. Susan told me that all three of her kids played competitive sports into college. When they were young, their dad coached three sports, but basketball became the boys’ main focus. Through sports, Susan said, the boys made friends from all walks of life, and their coaches provided another level of adult supervision and mentoring And although they were both good students, Susan believes it was invaluable that each of them had something else so significant in their life.
Scooter went on to play basketball at Emory, and Adam played basketball at Brown. Playing competitive sports in college forced them to become very efficient and disciplined about managing their time, Susan said, and playing team sports forced them to live up to their teammates’ expectations, while teaching them how to get along with others. She also spoke about how important it was for others to watch her sons lose—not just their teammates, but also the crowd—and for them to learn to pick themselves up, deal with their losses, move past them, and try not to repeat them. “Learning how to lose gracefully in a public way was so important,” she said, “even though it was hard for me to watch.”
I started thinking about the difference between playing team sports like soccer, basketball, and hockey compared to individual sports like tennis, golf, and swimming. Both teach you how to focus on a goal and how to win and lose; both teach you to strive and to compete; both force you to set priorities and to be organized with your time. Both team sports and individual sports teach invaluable life lessons, but they are different experiences. Team sports are more about learning to collaborate and realizing how your contribution can be critical to success, and about getting along with others. Individual sports are more about realizing there are no excuses, and that there’s nobody else to blame—or credit—for success or failure.
I told a friend my theory about the different skills individual and team sports teach kids and he said, “Maybe parents should try to get their kids to play both.” I replied, “No, that misses the point. The idea is that you expose them to everything, but then you support them in the sport they choose.” The key to having it work for your child is that it must be a sport—or some other competitive activity—that your child loves. That is one of the most important lessons in this book. You can give your child your advice about the pros and cons of any activity, but it must be your son’s passion for him to want to compete; it must be your daughter’s choice to commit herself to it.
I first met Alan in 2010, when he offered to sublet his sixth-floor walk-up in New York City’s Chinatown to my son Austin, who had just graduated from college. He was the founder and CEO of Arbitrage, a stylish clothing company, and he gave Austin a couple of really cool shirts. He’d been a basketball player when he was younger, and he told me that playing sports taught him invaluable lessons he used as his business grew: to work hard, to be prepared, and to adjust his game when the competition changed:
I was born and raised in Toronto. My parents are Ronnie Leung and Wing Chow Chan. My sister laid out a path for me to follow when she went to Stanford—my goal was to go to the U.S. Although I was always a good student, what I really cared about in high school was basketball. I also played soccer and baseball, but basketball was my passion. I was team captain my junior and senior years and won the Best Athlete award when I graduated.
Basketball was a huge influence on my life, and very important in my becoming an entrepreneur. The leadership experience from being captain helped develop my entrepreneurial spirit. Motivating my teammates showed me I could motivate employees. I even think the fact that my coach really believed in me gave me the confidence to start a business.
Playing sports teaches you preparation. I learned I have to have a game plan. I learned how to execute, how to prepare for the championship game. Because I had that experience, now I go into key meetings very calm, very prepared, ready to dominate and kill the meeting.
Being an entrepreneur is the culmination of a series of successful meetings. The feelings I have today before preparing for a big meeting are the same as I had going into a big sports match. Because of that, I’m always ready now. As an entrepreneur, you get a lot of meetings, and you have two minutes to make the investor or vendor or client your best friend. If you can’t win them over, you won’t be successful.
I was always interested in clothing and fashion. I collected sneakers and basketball shoes. I was fanatic about products I liked. And I loved great ads—I put ads all over my bedroom wall.
I went to Cornell for pre-med, but during my junior year I took a class on how to start a business. That changed my life.
When we were seniors and were thinking about life after college, all my friends needed new clothes—business attire. The only clothes guys could buy at that time were baggy and not very interesting, so I saw an opportunity to create a better-fitting clothing line for young guys.
I incubated the company my senior year of college, moved to New York, and launched my company, Arbitrage, in 2006 with two friends.
It was doing really well. We were in Saks and Nordstrom’s. Then the recession hit, which hurt a lot of retail brands. All the department stores were losing money, and they started cutting the smaller brands. I had been doing the online marketing for the company, and I realized there was a need for better advertising on the Web. So we decided to pivot.
We hadn’t raised outside capital, but had bootstrapped it, which meant we didn’t owe anybody anything. So we decided we could put Arbitrage on hold for a while and pursue other ventures. I had two business partners, who went on to other things. We’re still friends.
Alan went on to start Bread, a company that created a platform for distributing full-page ads on websites, tablets, and mobile devices. Its customers included Lady Gaga, 50 Cent, and Pepsi. It was acquired by Yahoo in 2014. He told me, “I love what I do, and I think one reason I’ve been successful is the confidence I gained and the habits I learned from sports.”
Eric Ryan and a high school pal, Adam Lowry, cofounded Method in 2001 to make environmentally friendly household products that smell great and look cool. In 2006, Inc. magazine named Method the seventh fastest-growing private U.S. company.
Eric grew up in Grosse Pointe, outside Detroit, with two younger brothers—one of whom is now an advertising entrepreneur, the other in corporate finance. He told me he’d always wanted to be an entrepreneur:
I come from an entrepreneurial family. My great-grandfather moved to Detroit to work for Henry Ford for $5 a day and then founded his own machine-and-stamping company with my grandfather. My father kept it until the eighties, when he just couldn’t compete anymore.
His mother’s side of the family also contributed to Eric’s sense of determination and hard work, according to his mom, Pam:
We were blessed. My husband and I both came from families with strong values. I was one of six kids, and my father died suddenly of a heart attack when I was sixteen and the youngest was three.
Both my parents had a wonderful work ethic—my mom worked so hard for all of us, and we all worked hard for her. Whenever I’d think, I can’t do this, I’d think, Wait, my mother had six kids—I’d better get moving! She also had a passion for her family, and that passion for family was passed down.
Eric told me that his mother’s stories really resonated with him, and so did the ones from his dad’s side:
I always loved listening to entrepreneur stories and reading books by entrepreneurs. Other kids built forts or space villages with their Legos. I built office buildings.
I was always working on a business idea. In lower school I got a machine and made and sold buttons with funny sayings. I made and sold hockey nets. I sold stationery. I had a plan to launch English-muffin pizza.
I also worked at jobs through high school and college for my spending money. I ran the middle school bookstore. I bagged groceries. I delivered pizza. I shoveled snow.
I always worked. I was a terrible student, but I really enjoyed working and thinking up business ideas. There was never a time when I wasn’t working on an idea.
It was sports that helped Eric develop the perseverance to see those ideas through. He grew up on Lake Michigan, so his passion was sailing:
I first sailed when I was in summer camp after fourth grade, and I loved it. I sailed competitively through college. My dad would drive the boat up and down the East Coast, to St. Petersburg or Newport, so I could race. He was always there to support me at regattas, even though he didn’t know anything about sailing.
It’s a very complicated sport. I tell folks if it’s windy, it’s very athletic, like rugby, but if there’s no wind, it’s more like chess.
It also teaches you a lot of independence. You have to be so well organized. You have to be a self-starter.
I wasn’t a good student, but I loved sailing and worked hard at that. I chose where I wanted to go to college based on the sailing team, and I raced at the University of Rhode Island. I raced until a couple of years ago, when I had three kids. I miss the competition.
That competitive fire helped drive Eric’s career. Unlike most of the other entrepreneurs I spoke with, whose passions were for particular areas of business, he looked around until he saw an area that needed disrupting. He realized that the cleaning industry hadn’t changed in years—the products had an unpleasant smell, and they weren’t environmentally friendly. So he decided to revolutionize the industry:
I knew I was going to start a company, but first I worked at an advertising agency. It helped me understand cultural shifts and marketing.
I spent a lot of time looking at different categories where I could start my business. I liked the idea of going into what appeared to others to be a boring category and finding a way to do it differently.
The cleaning category caught my eye. Everything looked so similar. I knew I could do better. I thought it was a big opportunity to connect your lifestyle with your home.
I thought my friends would laugh at me if I told them I was going to start a cleaning company. When I told my mom, she said, “I’ve never even seen you make your bed!” But my folks really believed in me and gave me $10,000 to get started.
I knew Adam from high school—we were both sailors. So in 1999, I told him what I was planning. He said, “I have a degree in chemical engineering,” and offered to help me, and we decided to become business partners.
It was a classic entrepreneur story. We laid out our vision. It seemed so obvious that we couldn’t believe nobody had done this before.
We gave our business plan to twenty smart people and asked them what was wrong with it, and nobody could come up with anything. We went store to store to pitch the product. We’d get twenty seconds to make our pitch in the back of a store.
We got it into twenty local stores. We hand-delivered the product. Then we went to independent premium stores, then to regional stores.
Eventually, after raising both an Angel round and Series A money from investors who, according to Eric, “believed in us more than they believed in the product,” the two cofounders had their product in eight hundred stores in the Detroit area. At that point, Eric said, what they really wanted was to get their product into a nationally recognized chain:
We met someone at Target who said we had a snowball’s chance in hell of getting it into his store. We knew we needed to get to a certain size to start making money. We were still losing money on each bottle.
At every step of the way, Eric and Adam drew on the grit they’d developed in their sailing days. They knew that if they kept doing whatever the situation demanded, whether the wind was filling their sails or not, they’d eventually see success:
Our first lucky break came in 2002, when we got a meeting with Target’s marketing department. The buyer who had already turned us down was annoyed. Somehow, they agreed to do an eighty-store sample, but there was a sales number we had to hit. We started buying our product ourselves to make our number. We’d go to a store, buy it, and then ship it back. We knew we had to make the number, and we figured we’d do whatever it took. We knew if we could get national distribution, we could afford marketing.
The buyer who didn’t like us retired. Fortunately, the new buyer loved our product. He gave us national distribution. Target is now a huge customer.
In 2012, Method had revenues of more than $100 million, and in 2013 it was sold to Ecover, which then became the largest green cleaning business in the world. Eric is still involved, and he recently built a new Method plant, which is a living example of the company’s mission and values. Everything about the new plant—its location on the South Side of Chicago, its practice of hiring local people, its wind turbines and solar trees, its rooftop greenhouse (the world’s largest) built to bring fresh produce to a food desert—was designed with sustainability and social good in mind. Eric has also started OLLY, a company that aims to do for vitamins and nutritional supplements what Method did for cleaning supplies—make them fun, green, and easy to understand.
Erika Paola Gutierrez is the founder of epgPR, a public relations firm with scores of clients. The firm does marketing, branding, and media placement in dozens of magazines and newspapers as well as on TV.
I asked Erika what had motivated her when she was young: like Eric Ryan, it was athletics more than academics. Her story is another example that it doesn’t matter what you compete in; it only matters that you learn to compete:
For eighteen years, my life was just ballet and acrobatics. I competed seriously from the time I was ten.
At first it came effortlessly. I was in third grade and walked into an acrobatics studio where girls were doing backflips. I said, “I can do this.” My mom said, “Are you sure?” I went into the class. By the end, I was doing backflips and cartwheels with no hands.
I started winning competitions. And then I really got into it. I was training for hours every day. Ballet classes, acrobatics, jazz, modern dance—I did that all through high school. Every weekend I’d be in competitions. I worked really hard at it, and I was so good at it. I loved it.
My parents were so proud. My mom, Edilia, still talks about it to this day. They both were always so supportive of whatever I wanted to do. Dad was busy at work, but he never missed a competition or a recital. Dad would always say, “Do whatever you want—anything you think you’ll be good at.” I got yelled at a lot about school, but my parents were proud about the dance and acrobatics.
I’m the middle of three children. We moved around the world for my dad’s job as I grew up—Mexico, Austin, Canada, Michigan, Miami, and D.C. I have an older brother, Carlos, who’s a lawyer, and a younger sister, Karina, who works with me part time. They’re the insanely smart ones in the family; they always got straight A’s.
I never did well in high school and didn’t focus on school. My parents were always furious with me about my studies. My mom pushed me every day to do my homework, but I just didn’t care.
It hurt my confidence level. I began to think I wasn’t smart. My mom said, “There’s no such thing as smart people. There are people who work hard and people who don’t.” My dad said, “Hard work always pays off.”
I didn’t get into a great college, didn’t study, changed majors three times, and barely graduated after five years. Education was really important to my parents, but it just wasn’t important to me then. I’m ashamed to say I just didn’t care. I regret it now.
Erika’s parents didn’t understand why the grit she’d developed in dance and acrobatics didn’t translate to her schoolwork. Eventually, though, Erika decided to apply the same hard work and tenacity to school that she’d been applying to the activities she cared about:
After college, I moved to D.C. and got a job at the Department of Labor. It was kind of overwhelming, being around so many educated people. I decided I had to change my life, and I knew that I was the only one who could do that. So I brought back my sports discipline and drew on it as if I was training again to compete. I worked my butt off studying for the GREs, and I got into Georgetown.
I got a master’s in corporate communications and public relations. I graduated with almost a 4.0, because this time academic success was my decision, and I was studying things I cared about. For the first time, I felt like one of the smart ones.
I had always been good with people, and I knew I wanted to go into an industry where I could use my strengths. I got a job with a big PR firm and worked there for six months.
I saw so many people starting their own firms, and I remembered how I felt walking into the gym for the first time. I thought that if they could do it, I could do it, too. My parents were very supportive and gave me the courage to start my own firm. That was four years ago. I’m very lucky. I’ve done very well.
Seeing how proud my parents are of me, I realize it doesn’t matter how smart you are or how good your grades were. All that matters is how much drive you have and how good an executor you are. That’s the key to being successful. It’s true in sports, and it’s true in business. If you have ambition and you have drive and you can execute, you’ll be successful.
You can’t assume things will come to you. You have to go after them. You have to force yourself to work harder than other people, and harder than you ever have. You can’t let yourself get discouraged. You can’t ever give up. I did this with dance and acrobatics for years before I started doing it in other aspects of my life.
The kids who went to high school with me probably thought I’d be a failure in life. They’d be surprised.
My dad, Carlos, didn’t have a college degree. He left Cuba when he was seven and started out driving a truck in Mexico. Twenty-five years later, he was the CEO. He told me how he always set goals for himself. First he said, “I’m going to be the manager of the trucks,” and then he said, “I’m going to be the manager of the Mexican group,” and he just kept setting new goals. Now my dad says, “We’re so proud of you. You’ve set such high goals.”
Radha and Miki Agrawal are serial entrepreneurs and identical twins. The sisters have cofounded five projects. Their biggest is Super Sprowtz, a children’s entertainment movement focused on healthy eating. They’ve produced more than twenty-five videos designed to show kids, in a fun way, how vegetables have “superpowers.” Several of the videos feature Sam Kass, former chef at the White House, and Michelle Obama.
Radha is the CEO of Super Sprowtz. She’s also a cofounder of Daybreaker, a global morning-dance movement, and Thinx, an underwear company that benefits women in developing countries (whose motto is “Change your underwear, change the world”). Miki is the CEO of Wild, farm-to-table pizzerias in New York City and Las Vegas. Miki is also the author of Do Cool Sh*t: Quit Your Day Job, Start Your Own Business, and Live Happily Ever After.
Radha told me, “We love to organize experiences that we hope will change the world. We were so influenced by our mom, who showed us, through her passion and determination and drive, how to make a difference.”
They have one sister, Yuri, who’s a year older, went to Harvard, and is a surgeon. The twins’ mom, Mire Kimura, is from Japan; their dad, Raj Agrawal, is an aeronautical engineer from India.
I’ve known Radha for a few years, but I never knew that she and her sister were known as the legendary Soccer Twins. They played soccer in high school, and played all four years they were at Cornell. Radha was a striker, and Miki was an outside midfielder. Radha told me how they got started, and how important soccer became to them:
Yuri was enrolled in a soccer program when she was five, and one day we went to see her game. Miki and I were both so excited, we wanted to play, and we ran onto the field. The coach had to stop the game.
But our parents saw how much we loved it, so they organized a soccer team for us. Then they not only drove us to practice, they organized the practice and coached our team. For eight years, my dad was our coach and my mom was an assistant coach until we started playing on higher-level teams and doing travel soccer.
We had three hours of soccer practice every day, our whole life. You have to be so disciplined. You really learn to be organized and focused. And you learn the politics of teamwork, and what it takes to be the captain. It’s not just all the work when you play sports in college—it’s all the work you put in before you get to college.
But Radha told me that grit was something she and Miki learned from their mom’s personal story even before they learned it from sports:
We were born and raised in Montreal. My mom told us that all kids go to school seven days a week. For ten years we went to Japanese school on Saturdays and Hindi school on Sundays. So we speak four languages. We didn’t come to the U.S. until college.
My mom’s story inspires me with her spontaneous adventurousness and her willingness to pursue her dreams. She went to Ottawa from Japan to go to grad school for a year, and met my dad there. He’d come from New Delhi to get a PhD. They were both supposed to return home after their education.
My mom came from a wealthy family. My dad came from a merchant family. He arrived in Canada with $5, which he spent on a winter coat from the Salvation Army. He got a loan from a bank to take my mom on their first date.
Despite knowing that her parents were adamantly opposed to their marriage—her mom didn’t come to the wedding—my mom chose love. She drove herself to her wedding, and on the way she got a flat tire and changed the tire in her wedding dress. And she married my dad.
To me, that’s hugely inspiring—that love is all that matters. My mom was always the woman who took a chance. If my mom saw a hole, she filled it. She showed me that if you want something done, you do it yourself. You don’t wait for others to do it for you.
We met Paige Mycoskie, founder of Aviator Nation, in rule 1, about nurturing kids’ passions. If Paige’s last name looked familiar when you first saw it, maybe that’s because you’ve heard of her older brother, Blake Mycoskie, the founder of TOMS, a shoe company that gives a pair of shoes to a child in need for every pair of shoes someone buys. They have a younger brother, Tyler, who works with Blake. We’ve already met their mom, Pam, who was unconditionally encouraging when Paige dropped everything in her twenties and moved back home to learn how to sew. Their dad, Mike, is an orthopedic surgeon in Arlington, Texas.
Pam told me that all three kids learned to compete and work hard when they were young. Like many other entrepreneurs, Blake and Paige grew up as avid athletes:
Sports played a big role in the kids’ lives when they were in school. Blake played tennis, and our family was always there at tournaments to support him.
Paige played all sports, but her biggest sport during high school was volleyball. Her team won the state championship. Our family traveled all around with her.
And we all supported Tyler at his paintball tournaments.
It taught them the importance of supporting each other. We told them, “We’re supporting your sibling. Your turn will come.”
We lived in a tennis neighborhood in Texas, and when Blake was seven, he just decided he wanted to play. He started riding his bike to the club every day. Eventually we got some good coaches for him.
Blake wasn’t the best, but he was always the most self-motivated. I never had to push him. He got the award for being the hardest worker on the team his senior year in high school, even though he wasn’t the top player.
Blake’s passion evolved from sports to business, and in this he was like many other athletes who became entrepreneurs. He had earned a tennis scholarship to SMU, but when an injury to his Achilles tendon forced him to quit, he started EZ Laundry, a campus-based dry cleaning business, which eventually expanded from SMU to other campuses in Texas.
According to Pam, “Blake kept looking for the next thing”:
He founded an outdoor billboard company in Nashville called Mycoskie Media, which he sold to Clear Channel. Then he and Paige competed in the second season of The Amazing Race, missing first place by four minutes. Next he started a reality cable TV network called Reality Central.
Every time Blake launched a new business, Pam told me, she and her husband reacted somewhat differently:
Mike always said, “Maybe you should think about it.” But I always said, “Wow, that’s great!”
“I was always the cheerleader,” Pam said, and she went on to tell me what I’ve heard from so many other moms whose kids grew up to become entrepreneurs:
Whatever the kids chose to do, I encouraged them. I don’t think kids realize at the time how important it is to have your family support whatever you want to do. Just because your child isn’t the valedictorian or number one player, it’s your enthusiasm and support for them that matters.
Aside from her family’s belief system and closeness, Pam thought another experience influenced her children’s approach to life:
The kids saw me struggle with, but not give up on, a big project—writing a book. I found out that I had high cholesterol, and I had to change my diet. I wanted to share how I got my cholesterol down, so I wrote a book with recipes for how to cook with less fat, Butter Busters.
I didn’t know anything about writing a book, and I didn’t know anything about the publishing industry. The kids packed up the books with me on the dining room table. We started out borrowing $60,000 to self-publish it.
Another mom might have hidden how much she was struggling, not wanting to upset her children. But Pam chose to share her experience with them. Her kids learned that everyone has to deal with problems—and that, with grit, problems can be tackled head on.
The book ended up selling one and a half million copies. Blake went on to write a book, Start Something That Matters, and for every book purchased, he gives a new book to a child in need. “He wrote about my cookbook experience in his book,” Pam told me. “When I read what he wrote, I realized that watching me struggle had had a positive impact. They thought, If our mom can write a book and get it published and have it be a big success, then we can succeed with our dreams too.”
A key difference between entrepreneurs and successful people in other fields has to do with their attitude toward failure. People in law, medicine, banking, government, and retail hope to avoid failure at all costs, but people who become entrepreneurs tend to view failure as a positive experience. They believe they’ve learned and grown from their failures, and that their failures have increased the probability of their success over the long term.
Athletes tell you how important it is to set “reach goals,” even if they don’t meet them, because it keeps them focused on the end result. Entrepreneurs know this too. They strive; they fail; they change their approach; they work harder. Athletes learn to be focused; they’re disciplined. After each failure, they try again. They never give up.
As Billie Jean King put it, “I don’t call it failure, I call it feedback.”
People often are under the impression that successful adults experienced a lot of success as children. But much of the time, that’s not true. Many became successful adults because they learned how to deal with failure. Goldman Sachs president Gary Cohn struggled in school and in his early jobs: “My upbringing allowed me to be comfortable with failure. The one trait in a lot of dyslexic people I know is that by the time we got out of college, our ability to deal with failure was highly developed. And so we look at most situations and see much more of the upside than the downside. Because we’re so accustomed to the downside. It doesn’t faze us” (Gladwell 2013, 123). In his book David and Goliath, Malcolm Gladwell observes that many other successful businessmen—Richard Branson, Charles Schwab, Craig McCaw, John Chambers—struggled with dyslexia, which helped them learn not to be afraid of failure. Many of the entrepreneurs I spoke to learned that lesson through sports.
In Building Resilience in Children and Teens (2015), Kenneth Ginsburg writes that many parents won’t address the fact their kids have failed because they want them to feel good about themselves. They think they’re helping their kids because they believe that shielding children from failure will keep them from feeling sad. In fact, it’s the reverse. We don’t do our children a favor by protecting them from realizing they could have done better.
As Dr. Ginsburg observes, “Most parents worry terribly when children fail at something…so we respond by saying and doing anything to brighten their moods. We deny it was a failure… . We blame someone else or reassure the child, ‘It just wasn’t your fault.’… Responses like these are…misguided because they send the message that feeling bad is a disaster.” He goes on to say, “Rather than cheering up a child every time he experiences failure or disappointment, we should focus on resilience. We all have failures. Resilient people learn a bit from every failure. They learn how to do better the next time. They are persistent. They use those bad feelings to motivate themselves a little more” (2015, 114).
There is a great quote from Maya Angelou about failure: “Courage allows the successful woman to fail, and learn powerful lessons from the failure so that in the end, she did not fail at all.”
Clemson management professor Wayne Stewart looked at serial entrepreneurs—adrenaline-driven men and women who start business after business (Bounds, Sporz, and Flandez 2007). He found that those who’d started three or more businesses share common traits:
I believe their attitude toward failure is traceable to how they were raised, and what their parents and their mentors—whomever they looked up to—taught them about failure: that it’s just one step on the pathway to success.
This was my son Elliott’s favorite quote, which he had on his wall during high school. He hadn’t heard people talk about grit, but that’s what it’s about. It’s Teddy Roosevelt’s famous “daring greatly” philosophy:
It is not the critic who counts;
not the man who points out how the strong man stumbles,
or where the doer of deeds could have done them better.
The credit belongs to the man who is actually in the arena,
whose face is marred by dust and sweat and blood;
who strives valiantly;
who errs;
who comes short again and again…
who at the best knows in the end the triumph of high achievement,
and who at the worst, if he fails, at least fails while daring greatly,
so that his place shall never be with those cold and timid souls who neither know victory nor defeat.
I thought I was raising a tennis player when he was in school, but as I look back, it turns out I was raising an entrepreneur. I just didn’t realize at the time that playing a highly competitive sport like tennis at a serious level nurtures the same skills.
Elliott loved all sports growing up and played everything when he was young: baseball, basketball, soccer, football. Around the time he was twelve, he decided he wanted to focus on tennis. The key words in that sentence are “he decided.” We didn’t push it—in fact, we were surprised, and it was a bit of a hard sell. (“You want to take a private lesson every week for how much?”)
But he pushed—to take more private lessons, to get into a more challenging clinic, to practice more frequently, to spend the summers in tennis camps, to start playing tournaments. We saw how focused and determined he was, and how much he loved it, and recognized that the daily grind of hours on the tennis court was what made his heart sing, so we went along with it.
When he started playing seriously, all the top kids his age were already playing regional and even national tournaments. I said, “I’m not taking you to an out-of-town tournament until you win a local tournament!” I didn’t realize I was giving him a goal and inspiring him to work harder; I just didn’t see the point.
Elliott single-mindedly fought his way up to a national ranking of thirty-five in the country in the juniors by the time he was eighteen. At first, he lost almost every match. But after each loss, he picked himself up and said, “I know what I did wrong; I’ll beat him next time.” I didn’t appreciate it then, but that was perfect training to become a successful entrepreneur: learning to lose; figuring out why you lost; determining what lessons should be applied next time; changing your strategy; not getting discouraged; and trying again.
Sports teach every athlete differently. Elliott started a very competitive sport relatively late, losing many matches the first several years. It taught him resilience, determination, focus, the correlation between preparedness and success, and especially how to deal with setbacks. On the other hand, if you’re really good, think of yourself as a star, and aren’t used to losing, you learn very different lessons. Maja Kermath told me that one of her most crucial lessons was when she lost her college tennis scholarship.
Maja was born in Communist Poland, but her family left as refugees, emigrating first to Australia and then to the U.S. She and her parents and her younger brother lived in Spokane and Chicago before settling in Champaign, Illinois. “Our journey exposed me to different people, places, and environments,” she told me. “I’m definitely a product of the American dream.”
One constant for Maja, as she negotiated the twists and turns of adjusting to a new country, was tennis. “I was always athletic,” she said. “In high school, I took two lunch periods so I could get my homework done and play tennis after school. I was the top player in the state, and I was getting straight A’s.” But she was also getting no small amount of flak:
I was always fighting a battle. I thought I knew how we could change the way things were done in order to improve them. And I would tell people in charge how they could do things better.
The school was furious with me and wanted to hold me back to punish me. But I always knew my parents had my back when I was fighting my teachers or my principal or my tennis coach. My mom sat down with the principal and convinced them to let me go ahead. It gave me the confidence to know I could do anything I set my mind to.
Tennis also gave me confidence. There’s nothing more powerful than to know you have all the tools you need to control your destiny. I’ll never forget the moment I realized this. It was quadruple match point to become the state champ, and I knew I was not going to fail. I had trained endless hours for that one shot. I knew I’d hit it. And I did.
After high school, Maja went to Creighton University and played D-1 tennis on a scholarship. That’s where she learned for the first time about failure:
Suddenly I wasn’t a star anymore. In high school, I didn’t lose a match in three years. In college, everybody was better than I was, and I kept losing.
Looking back, I know now that I was very difficult. I had a really bad attitude. I had arrived thinking I was the best thing since sliced bread, and I didn’t have the capacity to deal with that kind of failure.
The pivotal moment for me was when they pulled my scholarship. I reacted from my ego and said, “Then I quit the team!”
The thing that defined me—I was a tennis player—had just been taken away. I called my parents, and I was crying so hard. My parents told me to use what had happened as a learning experience.
It was a really painful time for me, but I learned that you have to be humble, and that you’re always replaceable. If I had to do it all over again, I’d have sucked it up, earned the respect of the coaches, and played the last two years. It’s one of the biggest life lessons I’ve ever had.
In time, the experience taught Maja not to be afraid to fail. She grew to realize that facing failure gave her courage and strength. And she needed plenty of both when she faced a critical juncture in her career. She had earned an MBA degree from the University of Illinois and gone to work for AT&T:
I kept rising in the ranks, getting promoted, and buying lots of stuff I thought I should have, including a Saab and a beach house. I always knew I wanted to start my own company. But I knew I needed to learn about how to run a company and thought I could do that by working at a great company and keeping my eyes open.
One day, I flew to another city to talk to a roomful of entrepreneurs about how they could try to land a deal with us. That evening, I got on a plane to fly home, and it was the first moment I’d had all day to be without anyone who knew me, and I just started sobbing. I was so unhappy with my life. I didn’t understand where the tears were coming from. My whole life I’d done everything everybody had asked of me—the Division 1 school, the MBA, the Saab, the house on the beach. Why was I so miserable if I had what I should want?
I decided I needed to compare how I wanted to spend my time with how I actually was spending my time. I knew I needed to change what I was doing.
I wanted to be living an inspired life, from what I was putting in my body to what I was putting on my body. I wanted to achieve wellness, and to be happy.
Maja left Los Angeles—and AT&T—for Texas. In Austin, she launched Kor180, a lifestyle brand that franchises studios featuring Pilates, cycling, and wellness. She didn’t know anyone there, she told me, but she had a “gut feeling” that Austin was the place for her to be:
From a sad moment, I created a modern wellness franchise. My dad was my first investor. He was the first person I called. I laid out my plan. He said, “Give me forty-five minutes while I talk to your mother.” He called back and said, “We’re in.”
The six months after we launched were the most difficult of my life—emotionally, spiritually, and financially. Every day as an entrepreneur, you lurch from one extreme to the other. My family got me through. They believed I could do great things and always told me that I could do anything I put my mind to. Who am I to launch the next billion-dollar business? But then again, why not me?
In David and Goliath (2013), Malcolm Gladwell says, “Courage is not something that you already have that makes you brave when the tough times start. Courage is what you earn when you’ve been through the tough times and you discover they aren’t so tough after all” (149). If you are not afraid to fail, you are more willing to risk everything for a big idea. You ask yourself, “What’s the worst that can happen?” And after you analyze the worst possible outcome, you say to yourself, “Yeah, I can live with that.”
An astonishing number of these successful entrepreneurs played sports at a very competitive level. Their dogged pursuit of excellence was a key ingredient in their later entrepreneurial success: they learned how to compete; they understood the direct correlation between hard work and results; they learned how to prepare, to “survey the course” or “review the game films”; and they learned to win with humility.
Other future entrepreneurs learned these lessons by competing in nonathletic pursuits: by acting or singing, or by entering art contests, academic contests, or sales competitions. Reggie Aggarwal learned it through debate and running for student office.
In the space of less than a decade, Reggie Aggarwal went from being a thirty-three-year-old forced to move back in with his parents after his company failed to becoming a model leader who turned the same company around and raised its value to well over a billion dollars.
Reggie’s company, Cvent, was founded in 1999 to provide companies with software to help them register people for events. Starting with $17 million in funding, Reggie grew the company quickly, and by 2000 had 125 employees. But when the dot-com bubble burst, the company had only $1.5 million in revenue. Reggie couldn’t cover his costs, and he couldn’t raise any more money.
Like many other successful founders, Reggie refused to throw in the towel. He decided it was time to pivot from fast growth to cost-cutting. He let 100 employees go, gave up his salary for two and a half years, and asked his remaining employees to wear multiple hats and even double up in hotel rooms when they took to the road on business.
“We were the walking dead for three years,” he told me. “But I powered through it for my team. I refused to give up. I had 120 investors—I couldn’t let them down. I was so focused on surviving, two years flew by.”
Cvent turned the corner in 2003. By 2008, revenue was growing at an annual rate of 30 percent. In 2011, Reggie raised $136 million in venture capital and finally cashed out his original investors, who’d been waiting twelve years. Cvent went public in 2013, and today the company operates in more than ninety countries, has 2,000 employees, and brings in annual revenues of $200 million.
When I asked Reggie how he had found the courage to persist through that hard time, he told me that he’d first learned to deal with failure as a member of his high school debate team:
I had played sports, but I wasn’t great. For me, the real competition came from debate, where I developed the single-minded focus to win. I joined the team my freshman year and really experienced the thrill of competition. It was the first time I did something I wanted to that I didn’t have to. The competition was one on one. It got me excited about learning, about winning.
He had two debate coaches, both women, who were hugely influential and became great mentors. Most weekends, he traveled with them to tournaments all over the country. Debating was his whole life for three years. He told me that he learned to analyze his losses and figure out how to improve. “Putting myself in a competitive environment trained me for the battle of business,” he said.
In his senior year of high school, he ran for student body president, and won. He also ran for office in college and was elected vice president of the student body at the University of Virginia. He found running for office similar to debating. “You put everything on the line,” he said. “You really have to believe in yourself to put yourself out there.” These days, he said, when he recruits college graduates for his business, he looks for people who have run for office.
Reggie told me that he’d never really wanted to work for anyone else, and so to earn money the summer of his junior year in college, he bought a franchise that employed students to paint houses. Little did he know what good preparation the experience would be for running Cvent:
I jumped right in, had twelve employees, and was working ninety hours a week. The first couple months, I was losing money. I didn’t want to give up and disappoint my employees. Finally, the last weeks of the summer, I got a couple big jobs, and we made money.
Reggie said his parents encouraged him, too:
When things didn’t go well, my dad would always say, “You’re measured by how high you bounce after you fall.” And my mom was instrumental in helping me push through failure. She always said, “Failure is a life experience that makes you stronger, so just learn from it, and jump into the next adventure.”
After graduating from college, Reggie went to law school at Georgetown and then joined a law firm. He found the courage to leave after meeting some successful entrepreneurs and realizing that if they could strike out on their own, so could he:
I learned they were no different from me. They didn’t have connections. They weren’t smarter. But I saw that they were willing to take a risk and willing to stick with it, no matter how tough. So I walked away from eight years in law.
My motto has been “Be persistent, be consistent.” It gave me the strength to get through the tough times for four years. It was really trench warfare.
Now nothing scares me anymore. I learned that whether you win or lose, you get confidence. That gave me the courage to power through.
Not all of the entrepreneurs I talked to were competitive: a lot of the “tech geeks” simply got really good at computers, while some of the artists were intent on perfecting their craft, or whatever their passion was. But for many entrepreneurs, learning to compete was key. It led to their desire to compete in their professional lives. And it led to their not being afraid to fail, which led to their willingness to take risks.
Starbucks founder Howard Schultz says, “The difference between winning and losing—or between success and failure—is that gray area of perseverance and will” (Graft 2012). When entrepreneurs learn while they’re young to compete—and even more important, not to fear failure—it makes them stronger. It creates indefatigable competitors.