Growth

What do Henry Ford, Sam Walton and Wendy Kopp all have in common? They all became mega-successful entrepreneurs. And before that, they were all called crazy.

I too was called crazy. For years, I was known as la chica loca for suggesting that high-impact entrepreneurs and high-growth businesses could be found in emerging markets outside Silicon Valley.

Today, that idea has morphed into Endeavor, a global network of over 1,200 entrepreneurs leading 850 companies that have collectively generated half a million jobs and $8 billion in annual revenues. If I had given into the naysayers, I would have killed not only my own crazy dream but also the dreams of a thousand other aspiring entrepreneurs taking on the status quo in their countries.

This is how I learned that the biggest barriers to success in the entrepreneurial age are not financial, educational, or cultural — they are psychological. You don’t need a Silicon Valley zip code, a string of VC backers, or a hoodie to be an entrepreneur! In fact, the largest demographic launching new businesses today are not young techies but women and baby boomers.

Since entrepreneurship is essentially about undertaking a bold new venture, being challenged and misunderstood is part of the process. You can’t rock the boat without being told you’re off your rocker!

Ok, so you’ve fended off the naysayers, overcome inner fear, embraced uncertainty and given yourself permission to go ahead with your crazy idea…Now what? Below are some of the counterintuitive rules I’ve gleaned over two decades of helping entrepreneurs around the world get their idea off the ground and into the stratosphere…

1. Close doors

If the first step to becoming an entrepreneur is about managing mindset, the second is about managing risk.

Our image of entrepreneurs as swashbuckling daredevils who go all in on day one is wrong. Sara Blakely, the creator of Spanx, kept selling fax machines until she got booked on Oprah; Phil Knight of Nike kept his accountant job while selling sneakers out of his Plymouth Valiant. In the year that it took to get Endeavor off the napkin, I wrote grant applications for other organizations on the side to earn extra money.

Contrary to popular belief, most entrepreneurs are risk-minimizers, not risk-maximizers. Even the biggest maverick of all, Virgin’s Richard Branson, prefers “contained disasters,” small bets with limited consequences if things backfire.

But at some point after your idea has taken off, the hedging has to stop. You can’t build a significant business with one foot out the door. Entrepreneurs often cling to their conventional work like a security blanket — out of fear rather than necessity — even after they can afford to pursue their venture full-time.

My advice: Once your idea has gained traction, cut the umbilical cord. Your idea can’t take flight if you don’t leave the nest — which brings me to rule #2…

2. Fire your mother-in-law

A few years ago, I asked our in-house research team at Endeavor to examine the best and worst performing entrepreneurs in our network to see if we could detect any patterns of success and failure. We learned that three-quarters of our entrepreneurs cofounded their businesses with a partner, and 70 percent of these partners were people close to them — a best friend, a sibling, a spouse, an in-law.

So what happens when family and business mix? Things usually start off swimmingly, but then trouble brews. Cash problems arise, and cuts need to be made. Or business booms, and one partner seeks to expand while the other prefers to stay small.

Endeavor entrepreneurs aren’t alone in this struggle. More than 80 percent of American businesses are family-owned, and the figure goes up to 90 percent outside the US: from the sons of IKEA founder Ingvar Kamprad to the wives of Rupert Murdoch, from Beyoncé’s dad to Usher’s mom (“I never fired my mother,” Usher told Oprah. “I relieved her of her duties”).

To keep bedroom issues out of the boardroom, I suggest drawing up a “startup prenup,” delineating each partner’s role, responsibility and ownership. In case someone wants or needs to pull out, devise a contingency plan for an amicable exit — and skip a lifetime of awkward holiday gatherings.

 3. Surround yourself with a circle of mentors

That’s not to say you don’t need a support system. If you want to go big, you can’t go at it alone.

The image of the individualist innovator is irresistibly romantic, deeply entrenched, and completely misleading. Entrepreneurs need help. Lots of it. And it shouldn’t all come from the same person. Save monogamy for your private life, and seek multiple professional partners.

Just as people are changing jobs more frequently in today’s economy, they should be changing mentors. You need mentors for every stage of your career who are at varying stages of their careers. To me, the right model is a 360-degree approach: a circle of advisers who can give you a rotating mixture of tough love, specialized advice, fresh insights and clear direction for when you need it the most.

You need mentors for every stage of your career.

If you are going to surround yourself with mentors, however, you can’t be afraid to reach out to them. A few years ago, Tory Burch invited me to a speed-networking event where I sat across from a young clothing designer, who couldn’t stop gushing about how much she admired Tory. Finally, I suggested that the person she should be telling all this to was Tory herself — who happened to be standing on the other side of the room. The young designer stammered, “What — Am I supposed to just go up to Tory Burch?”— “Yes,” I enthused, “that’s why you’re here!” At the end of the evening, I saw the same designer chatting with Tory and proudly handing her a business card.

You can’t play your cards right if keep them close to your chest.

4. Be flawsome

Once you’ve gotten yourself a circle of mentors, go one step further to make the circle complete: Become a mentor yourself…starting with your own employees.

Lead by example. For years I thought I had to adopt a hardline leadership style. Then, one day my husband read a speech I was to deliver before the company, and promptly tore it up: “Less super, more human,” he explained. In trying to sound authoritative, I ended up seeming unreal and unrelatable. No employee can get behind a leader who doesn’t come across as a genuine person. Forget trying to be awesome all the time, and settle with being “flawsome.”

Once you cop to some personal flaws, then adopt that attitude toward your company: You and your employees will inevitably make mistakes in the course of doing business; how you respond to those mistakes can end up influencing, and even defining, your brand. Danny Meyer, the celebrated New York restaurateur behind Union Square Café, Gramercy Tavern, and Shake Shack, sought to develop a reputation for impeccable service and hospitality among his staff. So, when he heard that a loyal diner at Gramercy Tavern had found a beetle in his salad, Danny felt stripped of his honor — but not of his humor. The next day, he sent the same customer, now lunching at Union Square Café, a complimentary salad adorned with a piece of paper that said ‘RINGO,” and accompanied by a server who explained, “Danny wanted to make sure you knew that Gramercy Tavern wasn’t the only one of his restaurants willing to garnish your salad with a Beatle.”

Vulnerability, once the Achilles’ heel of a fearless leader, has now become a sign of strength. Instead of bellowing from on high, today’s effective leaders encourage creativity to bubble up from below. Instead of being invincible, they allow themselves (and others) to be flawed. Instead of trying to be Super(wo)man all the time, they unleash their inner Clark Kent.

5. Eat the elephant one bite at a time

In Air Force survival school, cadets are taught to conquer moments of confusion with a memorable axiom: You eat an elephant one bite at a time. If you try to eat a 1,500-pound pachyderm in one sitting, you’ll ei­ther give up or get sick. The key to survival is to take it slow — Chew. Swallow. Repeat.

The same applies to entrepreneurs. We think of entrepreneurship as a big, scary thing, involving blind leaps of faith and sweeping acts of disruption. In fact, it’s about achieving daring dreams through prudent steps. It’s about destabilizing the world without destabilizing yourself. It’s about both embracing risk and mitigating risk.

The takeaway here is to persist when the path gets rough. Stay calm; narrow your options; get the right people on board (and get rid of the wrong); make targeted changes; accept failure.

Go slowly, but keep going.

Linda Rottenberg

About the Author


Linda Rottenberg


Named one of “America’s Best Leaders” by U.S. News and one of TIME’s 100 “Innovators for the 21st century,” Linda Rottenberg is Co-founder and CEO of Endeavor. Dubbed by Thomas Friedman as the “best anti-poverty program,” Endeavor supports 1,200 entrepreneurs in 25 countries leading 850 companies that collectively generate 500,000 jobs and $8 billion in annual revenues. Rottenberg is also the NYT bestselling author of CRAZY IS A COMPLIMENT: The Power of Zigging When Everyone Else Zags. A graduate of Harvard University and Yale Law School, she lives in Brooklyn with her husband, author Bruce Feiler, and their twin daughters.