Rule 4

Mentors Can Be Great

To a restless, creative kid, the world can seem rigid and rule-bound. It can feel as if everything’s designed to prevent them from exploring what’s truly interesting, or from even figuring out what that might be. But an adult who demonstrates that it’s okay to do things differently, to color outside the lines, can be powerfully validating. When that adult also trusts a child enough to hand him the tools he needs to start creating something new, he can be launched toward great things. A mentor can also broaden a young person’s view of available possibilities—many doctors’ kids go into medicine, and lawyers’ kids go into law or public policy, but a mentor can show kids a whole world beyond the world of their parents.

There are many important reasons for a child to have a mentor. Some are obvious—a mentor offers you help and guidance, teaches you, and promotes your growth. There’s another, less obvious reason—if a mentor believes in you, it will boost your belief in yourself. That can be especially important if a child is receiving less positive messages from others in her life.

A mentor’s belief in a child gives them confidence in their skills. That leads to resilience—and without resilience, it’s almost impossible to become an entrepreneur. Building something new means you won’t always be appreciated. Your early efforts might even be laughed at. You might work as hard as you can and still find that your project doesn’t catch on. Most people would take that experience as a sign that they should pursue a safer path. The entrepreneur just modifies what he has or starts a new project.

Mentors have one major advantage over parents. A mentor, unlike a parent, isn’t responsible for keeping a child safe. The ideal mentor is driven by a different impulse—to expose the child to challenges and equip her to handle them. A mentor can also give a much-needed kick in the pants that parents are reluctant to give. And a child, especially a teenager, may listen to a mentor precisely because the mentor isn’t a parent. At some point, as we all know, many kids start treating their parents’ advice with automatic skepticism, and so a mentor with the right values becomes even more important.

Most of the entrepreneurs profiled in this book had one or more mentors. A mentor doesn’t have to be famous or important. A mentor just has to be someone the child respects, someone who comes into the child’s life and shows her a new way of looking at the world, or who validates a child’s self-worth by understanding the way he looks at the world.

Fanning the Flame

Mentors are good for everyone. But if a child feels underappreciated at school, few things do more to boost his confidence than having someone who appreciates his talent, especially if that person is skilled in the area he loves most. It brings him joy and rejuvenates his spirit. If you’re not an academic star, or if your teachers find you annoying because you can’t sit still or you ask too many questions, what could be better than having someone who excels in the thing you love think that you’re incredible?

Remember Benny Blanco’s mom, Sandy, who used rule 3 in responding to teachers’ reports of her son’s difficulties at school by saying “So?” She also decided she had to find another adult who believed in Benny.

She was divorced from her sons’ father when Benny was in middle school, and the boys had a very difficult few years, but it was an important part of their development. “Ben was forced to take on a more mature role in the family,” Sandy said, “and I think it made him the compassionate, good boy that he is today.”

During this time, Sandy and her ex-husband often disagreed about whether the boys should attend a private school with a special education program, since Benny’s brother had also been diagnosed with ADHD. But Sandy told me that she was determined to keep the boys in a regular class so that they would fit into the “real world.” Which meant that when Benny got serious about music, he was a white Jewish boy going to largely Black middle and high schools. He made friends with kids from dramatically different backgrounds, and those friendships influenced his musical tastes.

He was a white rapper before Eminem made that acceptable. By his own admission, Sandy says, he was “horrible” at rapping. But instead of discouraging him, Sandy encouraged his growing love of music. She didn’t care what his teachers thought. She didn’t listen to her friends. She got him drum and guitar lessons outside school, and she found someone else who believed in him—a music teacher who said that Benny was the most talented student he’d had in thirty years. This meant everything to Benny.

By the time he was in eighth grade, Benny was winning rap contests. He sold his first song when he was a teenager. It was set to the beat of a soft-core porn video called Hip Hop Honeys, one that he insisted on showing to everyone. Sandy must have taken a big gulp. When Benny wanted to take five-hour weekend bus trips from Virginia to New York City so he could try to meet with rappers and producers, she must have taken an even bigger gulp. And when he wanted to drop out of college after a year to pursue music full time, she must have taken the biggest gulp of all before she finally agreed.

Ultimately, though, Benny’s mom let him do what he wanted, and he went all the way to the Grammys, where he earned nine nominations by his mid-twenties. Without the one-two punch of a parent and a mentor who believed in him, who knows whether Benny’s remarkable talent would have flourished? It’s clear that he understands the important role his mentor played in his life, because now Benny, who’s been nominated for the Songwriters Hall of Fame, mentors young musicians all the time.

Jesse Genet is a pioneer in the do-it-yourself world, thanks to Lumi, the company she cofounded. It’s based on an innovative photographic print process for textiles that offers an alternative to screen printing and lets people easily design their own clothes. One friend described Jesse admiringly as a “make-it-happen science geek.”

Jesse’s mentor was her stepfather, Doug, whom Jesse met when she was a teen:

I grew up in a suburb outside Detroit, with one sister six years older, so in some sense I grew up almost like an only child. My mom, Laureen Sue, was a schoolteacher. My dad was a lawyer. They divorced when I was twelve. Mom remarried when I was fifteen, a sophomore in high school.

Mom treated us like little adults, so I was always comfortable around them. Whether I was three or thirteen, she’d let me come with her. She’d say, “This is an adult place, so you have to act like an adult.” She taught me never to be afraid to deal with any situation. She trusted us and gave us a lot of freedom.

But I’d never met anyone like Doug. He was a technology developer and, unlike my parents, he had never had a normal job. He let me hang out at his shop after school. I’d do my homework there and watch how he ran his businesses. He’d humor me, let me sit in on meetings, let me be a fly on the wall. I sucked up this whole new world like a sponge. My sister was already in college when they got married, so this wasn’t part of her experience while she was growing up. She didn’t understand why I would hang out in Doug’s shop instead of with my friends. She’s much more traditional, with a master’s in engineering—ironically, she now works for me part time.

For Jesse, being trusted to create in a grown-up way was a transformative moment:

Doug was very hands-on. He’d show me how to do anything I wanted to do—build a cabinet, refinish the floors. It was all very exciting to me. And he had so many tools—woodworking, metalworking. He’d give me a demo, and then I’d go weld something. He trusted me to do it right.

Doug was the first person who wasn’t a direct family member who I asked for help and who said yes. This opened my eyes to how much you can get by asking. My dad was very traditional. Everyone in his family is a doctor, lawyer, or dentist. Everyone went to the University of Michigan. Doug showed me that rules didn’t have to be so rigid.

I’d been kind of a loner kid. I skipped my senior year in high school. I didn’t want to spend nine hours a day sitting in a class when there were so many other things I could be doing. I convinced my principal to let me take college classes. I spent a lot of time at the shop and took some online classes and some from a community college.

Although Jesse got into the University of Michigan, she chose to break the family tradition and went to the Art Center College of Design in Pasadena:

I decided to study something I felt I didn’t have an aptitude for. I was creative but didn’t know design. I knew that there was a lot I didn’t know, coming from middle-class America, and thought this was one way I could catch up. I began working toward a BS in product design.

I didn’t finish college. I met Stephan Angoulvant, with whom I cofounded Lumi. I’d been working on the concept for a while. I knew there must be a better, cheaper way to do printing.

Stephan has a lot of design talent. I have marketing talent and could translate the technology into what people want to use, and could communicate why the idea mattered. It was a good match.

Jesse started Lumi on the crowdfunding site Kickstarter in 2010, when she was still a student.

“I love what I do,” she told me, “and it’s been well received. Revenue should double next year.”

Jesse credits her mother with making her “confident and wise.” Her mom, she said, “teed up” her success with Lumi.

“But it’s only because of Doug that I became an entrepreneur,” she said. “Nobody else in my family understood my passion. I’m so happy I started spending time in Doug’s shop, even though everyone except him thought I was wasting my time.”

Encouraging Bold Choices

Kids who get plenty of recognition from their teachers and peers may not seem to have a great need for mentors. But even though stellar students and popular kids may not struggle with self-confidence, they still need encouragement to pursue their dreams. In a way, conventional success at an early point can actually hamper entrepreneurial success. An excellent student may be tempted to follow the well-worn path that is clearly laid out—the right activities, the best school, the most stable career, the highest salary. To get off this track and start laying their own tracks, accomplished kids may need a mentor’s encouragement.

Tom Scott, cofounder of the juice company Nantucket Nectars, sold it for tens of millions of dollars and went on to start other companies. Much has been written about Tom and the companies he’s started. His latest organization is The Nantucket Project, a gathering of people from all walks of life, from world leaders to small entrepreneurs, all of whom want to give back and make the world a better place.

I interviewed Tom’s mom, Jane, whom I’ve known for many years, about her son. She told me that he was always popular and a good student. But to become an entrepreneur—to avoid the safest route and take a chance—he needed a nudge from a mentor.

Tom was born in Chevy Chase, outside Washington, D.C., the third of four children, all born within five years. Jane told me that the first two kids were more difficult and took up a lot of her time and energy. Tom, on the other hand, “didn’t need a lot of parenting,” and she “kind of left him alone” because he always “seemed to know what to do”:

Tommy would do things out of the norm. He was always a leader, always the one who organized all the games, and all the others went along with it.

Tommy always wanted to work because he wanted money. His senior year in high school, we spent the summer in Truro, on Cape Cod, because his grandpa who lived there was sick. The kids wanted to stay home with their friends, so I said they could bring them. We had bought an old Boston Whaler with an engine, and Tommy took the boat thirty miles to Nantucket and started a painting company there. His first job was painting a bank.

After high school, Tom went to Brown, where he met Tom First, who became his business partner and eventually the cofounder of Nantucket Nectars. Jane told me:

They started their first company in Nantucket together while they were still in college—AllServe. Their motto was they’d do anything. They serviced boats in Nantucket that didn’t have a space on the dock. They did solid waste disposal, laundry, getting newspapers, lobsters—anything anyone needed. They brought their friends up from D.C. and Brown. They worked really hard.

After college—they graduated in 1989—they lived in Nantucket. Tom First had spent his junior year in Spain and had fallen in love with the peach juice there. The boys decided to start a juice company, and to put Nantucket in the name.

Tom First’s family was upset. They said, “This is what you’re doing with a Brown education?” They wanted him to get a real job and get on with his life.

The boys lived in their Suburban that first winter. They poured their life savings into the business. Tom First was the business side, and Tommy was the marketing/PR side. It was slow going.

About a year later, Tommy was trying to decide what to do. Lots of his friends were headed to jobs in finance, or to law school, or to business school. Tommy applied to Harvard Business School and was accepted.

He was on his way to a prestigious business school, which would lead to a job on Wall Street, at a time when that seemed to be every young person’s dream. At that point, shifting away from his struggling business and toward an MBA looked like a reasonable move. His parents were thrilled, especially his dad, a successful lawyer, who really wanted Tom to go to Harvard. All his classmates had jobs where they wore a suit to work. Rejecting an MBA to start a business, working out of your house, was almost unheard of back then. Without a mentor’s advice, he probably would have made the conventional choice.

But then, Jane said, Tom sought his favorite teacher from Brown, Barrett Hazeltine, who had become his mentor. Tom Scott and Tom First had both taken Dean Hazeltine’s course in entrepreneurship. “He was basically an ethics teacher,” Jane told me, “and he had tremendous faith in the boys. He’d helped them prepare their business plan for Nantucket Nectars.” Now, Jane said, her son sought his mentor’s advice:

Tommy asked Dean Hazeltine whether he should go to Harvard Business School. His professor answered, “You’ve got a great thing going here. Don’t waste your time going to business school. But don’t turn it down—defer for a year, and think about it. Also make sure the school knows about Nantucket Nectars.”

Jane told me that she and her husband trusted Dean Hazeltine to give the boys great advice. They agreed it was okay for Tommy to put the decision off for a year and see if the boys could make a go of their struggling business.

In the end, Tom Scott didn’t go, but he didn’t burn his bridges, either. Now the story of “the two Toms” is a case study at Harvard Business School (Lassiter, Sahlman, and Biotti 1998), and they speak there about Nantucket Nectars every year. In fact, Jane said, they were the first in a long line of superstar entrepreneurs to be inspired by Barrett Hazeltine. He taught them to live passionately, do what they love, and have the courage to do something different.

On Dean Hazeltine’s seventy-fifth birthday, his former students put together a book of tributes. Here is Tom Scott’s letter to his mentor:

Dear Dean,

I’ve recently turned forty, have two children and a wonderful wife. In other words, I’m sort of a grown-up now. Just using simple math, I’m pretty much middle-aged and have lived a significant portion of my life. One thing is certain—there is a very short list of people who have most significantly, and positively, influenced my life. I would put my parents, my high school football coach, and Dean Hazeltine at the top of my list.

Life is full of details. However, there are very few significant truths that can guide one’s life. The one I think you gave me is spirit. It is really such a simple concept. However, the message comes in some complex formula of qualities/emotions, etc. You have them. I can’t say much more than that—whatever that is, you have it and it greatly influenced me. I am very grateful. Furthermore, you are kind and make people feel good. I can only hope I can deliver some of what I learned from you to my children.

Happy birthday! But, more important, thank you!

Tom Scott

Class of 1989

While some kids had a single mentor who made a dramatic difference, most of the entrepreneurs and moms I spoke with mentioned several mentors as the kids grew up.

Alan Chan, whom we met in the chapter on competing (rule 2), cofounder of the clothing company Arbitrage and founder of the online ad distributor Bread, told me he had three mentors who changed his life:

My first mentor was my basketball coach. He picked me out from almost all the other kids, believed in me, promoted me. He chose me to play for the JV team as a freshman, which was almost unheard of in my school, then put me on varsity my junior year, so I was the team captain for two years. That made a huge difference in my perception of myself and my abilities.

A mentor can show you that there’s a big world out there, beyond that of your parents. It was another mentor who helped Alan realize he didn’t have to become a doctor:

My second mentor, Craig Frances, was even more influential in my becoming an entrepreneur. I met him the summer after my junior year at Cornell. I was supposed to be a doctor. Both my parents are doctors, as is my older sister. There was always huge pressure growing up to get good enough grades to get into medical school.

I was always on the honor roll in high school and on the dean’s list at Cornell with a 3.9 average. I felt a lot of pressure to be a doctor. But I also think that the necessity to excel was part of the driving force that made me become an entrepreneur.

By the end of my junior year in college, I had already gotten into med school, but I was also starting to be interested in business. I thought I might be able to be a doctor who also did business. I had learned a little about venture capital and private equity and thought that might be interesting. I Googled Cornell alums who were working in those areas, and then I e-mailed a letter with my résumé to eighty firms. I got only two responses, and only one interview.

Craig hired me as a summer intern, which turned out to have a huge impact on my life. He was the head of the health care and consumer products group at Summit Partners, a private equity firm. He invested in hospitals. He had gone through med school, had practiced medicine, and then quit to go into business. He said to me, “If you want to go into business, don’t waste your time and money by going to medical school.” I listened.

Coming from a parent or a teacher, that advice might not have meant much. But because it came from a mentor who had gone down the same path Alan was considering, it was powerful.

Alan went on to tell me about his third mentor, a real estate developer who was the father of his girlfriend that summer:

I saw that he had a much better work-life balance than doctors, and I knew I wanted that for myself. So I decided I was going to start a business, not become a doctor. First, I told my parents I was going to defer my med school acceptance to start my first company. After a year, they saw the writing on the wall and accepted it.

“If I hadn’t met those three men,” Alan told me, “I’d probably be a doctor today.” Having a doctor for a son is not exactly every parent’s worst nightmare, and I’m sure Alan would have made a wonderful physician. But he also always would have wondered what he had missed by not pursuing his passion. His mentors emboldened him to make what turned out to be the right choice.

The Gift of Inspiration

Some entrepreneurs were helped by a mentor in ways even more fundamental than nurturing confidence or encouraging bold decisions. For these fortunate entrepreneurs, a mentor provided not just guidance, but guiding principles—attitudes and beliefs to be drawn on over a lifetime, especially in adversity.

Elizabeth McKee Gore has never founded a start-up or a nonprofit organization. Instead, she has launched groundbreaking projects within existing organizations.

It’s scary to start an organization from scratch. But it can take just as much courage, confidence, and persistence to come up with an idea for a project, sell it to colleagues, implement it, and stake one’s professional reputation on its success. Elizabeth has done all this half a dozen times.

As executive director of global partnerships for the United Nations Foundation—admittedly not the world’s most entrepreneurial organization—Elizabeth was an “intrapreneur” who created three significant grassroots projects: Nothing But Nets, which raised $50 million, with an average donation of $60, for bed nets that offer protection from mosquitoes that carry malaria; Girl Up, which raises funds to provide girls with education, training, and mentors; and the Shot@Life global vaccines campaign. Elizabeth was also the foundation’s first resident entrepreneur, and she chairs its Global Entrepreneurs Council.

For the typical successful entrepreneur, a mentor is a professional who has already succeeded in the entrepreneur’s chosen field and now helps the younger person along. But Elizabeth’s mentor was a woman of modest means and no formal education—her grandmother, Opal. I’ve heard Elizabeth speak often of how much her grandma meant to her, but until I talked to her for this book, I didn’t realize how big a role she had played. She taught Elizabeth what was truly important. She taught her how to solve problems. She taught her to grab opportunities. She taught her never to give up:

My grandma inspired my brother and me our whole lives. I grew up in Whitesboro, Texas. My grandma lived six hours away, and I spent every summer and many weekends with her. My brother is five and a half years younger than I am and, like my grandma, he fishes every day. That’s not his job—he’s a tech salesman—but that’s his passion.

She wasn’t an educated woman, but she was always very wise—that’s why I named my daughter after her. Whenever I had a problem, I called her, and she always had a very grounding truth to share.

If there was a problem, my grandma always figured out how to fix it. I remember there was an old abandoned filling station near her home that she wanted taken down. She called the mayor’s office every day for three straight months until they finally did.

She and my grandpa were both products of the Depression and World War II. In fact, she was a riveter during the war. My grandma was always busy, but she spent most of her time on us. She’d take us to mud pie contests, fishing, youth activities, and church activities. With her, we were always going, going.

My parents started their own cattle ranching business, but most of my direction came from my grandma. I learned tenacity from her. She’d say, “Don’t sit there if you have a problem—solve it!” She also gave me her sense of community. She’d always tell me, “Use your powers for good.”

I was the first woman in my family to graduate from college. My grandma really pushed me to do that.

At Texas A&M, one of the most significant things that happened was that one of my friends had to drop out because she had a baby, and there was no support. I asked my grandma what I should do about it, and she said, “Well, figure it out.”

Those four simple words—“Well, figure it out”—contain the essence of what would become Elizabeth’s approach to work, the principle that would guide all her efforts. Elizabeth continued the story:

I researched the problem and discovered that our school was the only one in the Big Twelve without any child care. So I decided to raise money for a children’s center. I worked so hard at it, I almost flunked out of school. But it got me excited about the nonprofit world. I had been planning to work on my family’s ranch—I’d been studying animal science. But this opened my eyes to another career path.

While I was getting my master’s in financial development, because of my fundraising experience for the children’s center, I had an opportunity to raise funds for a foundation for the Bush School of Public Policy, which got me involved with the Points of Light Foundation, which took me to Washington, D.C. Then I met Billy Shore, who ran Share Our Strength, and I launched their anti-hunger initiative, The Great American Bake Sale. And that led me to the head of the U.N. Foundation, who inspired me to join her. I just let one thing lead to another.

After college, I joined the Peace Corps and went to Bolivia. It was the hardest thing I ever did. My grandma and I wrote letters back and forth. In one letter, I wrote how hard it was to get the farmers to work together and to trust me. I saved her answer: “Keep your head held high, and give ’em hell.”

That was her philosophy—have integrity, but give ’em hell. She was so committed to her community, and nothing would ever stop her from something she thought was right. She was always polite, but she never backed down.

My grandma taught me the entrepreneurial spirit. It’s why I’m able to build things today.

Where You Come In

The best mentors are often the ones children find on their own. After all, as we’ve seen, part of mentors’ value is that they’re not you! A mentor’s attention shows a young person that an adult who isn’t obligated to care for her thinks she has potential, is worth an investment of the mentor’s time, and has something special to offer.

But that doesn’t mean you can’t help your child connect with a mentor. Encourage your child to reach out to successful people in the field he’s passionate about. You can make specific suggestions, but be careful not to limit your suggestions to people you admire. One way a mentor can serve as a bridge to the adult world is by giving your child a different perspective from yours. Even though it may not be easy, you need to trust your child to make the most of that different perspective, because it’s a key part of letting him create his own perspective—the one he’ll keep refining for the rest of his life.