If you’re not called crazy when you start something new, then you’re not thinking big enough!

LINDA ROTTENBERG is the co-founder and CEO of Endeavor Global, a cutting-edge nonprofit supporting high-impact entrepreneurs worldwide. She has been named one of “America’s Best Leaders” by U.S. News & World Report and one of Time magazine’s “100 Innovators for the 21st Century.” A frequent lecturer at Fortune 500 companies, Linda is the subject of four case studies by Harvard Business School and the Stanford Graduate School of Business. ABC and NPR have called her “the entrepreneur whisperer” and Tom Friedman dubbed her the world’s “mentor capitalist.” She is author of the New York Times bestseller Crazy Is a Compliment: The Power of Zigging When Everyone Else Zags.

How has a failure, or apparent failure, set you up for later success? Do you have a “favorite failure” of yours?
Around the time that Endeavor reached its ten-year anniversary and I thought we were finally out of the woods, a forest fire swept in that nearly felled me. My husband, a bestselling author known for adventure travel, was diagnosed with life-threatening bone cancer, which somehow robbed me of my motor function. Suddenly, I couldn’t get on planes anymore and could barely even show up to

the office. I wasn’t sure if Bruce would survive and, honestly, I wasn’t sure if Endeavor would either. Fortunately, our incredible team stepped up and we grew faster than ever. Perhaps the fact that I wasn’t around to micromanage had something to do with it! But the lesson went deeper than learning not to micromanage. I gained a valuable leadership and life lesson when I returned to work after Bruce was thankfully cured. As a female CEO, I had made a point

to lead with strength and confidence. . . . Never let them see you sweat, or—even worse—cry, right? After I returned to work, that stonefaced posture no longer worked. Team members wanted to know how Bruce was doing, how our young twin daughters were doing, and how I was doing. I had no choice but to let my guard down and be vulnerable for the first time. Shockingly, rather than drive my employees away, it drew them closer. Young team members actually pulled me aside and confessed that they used to think I was “superhuman,” meaning I was unrelatable. Now that I was showing my vulnerability, they said, they would follow me anywhere. The lesson: Rather than striving to be superhuman, I would aspire to be less “super” and more “human.”

If you could have a gigantic billboard anywhere with anything on it, what would it say and why?
My billboard would say, “Crazy is a compliment!”

I was called “la chica loca” (the crazy girl) so many times when I launched Endeavor that I finally decided to own it. I hope others will too, because if you plan to try something new, especially if that something new disrupts the status quo, then you should expect to be called nuts. You can’t rock the boat without being told you’re off your rocker. The greatest asset of entrepreneurs is their contrarian way of thinking, their tendency to zig when others zag, to go in a new direction. But many people don’t give themselves permission to get going for fear that they will be called crazy. I say not only is crazy a compliment, but if you’re not called crazy when you start something new, then you’re not thinking big enough!

When you feel overwhelmed or unfocused, what do you do?

My twin daughters, Tybee and Eden, help me achieve perspective. They have greatly impacted both my personal and my professional growth. Just by virtue of being born, they changed my whole leadership style. I used to be a perfectionist, a micromanager, and a nonstop global traveler, but I had to learn to let go and occasionally say no in order to be with them. As Eden wisely pointed out at the ripe young age of five, “You can be an entrepreneur for a short time, but you’re a mommy forever!”

What is an unusual habit or an absurd thing that you love?

Perhaps my most unusual habit is (nicely) stalking people. My ability to “stalk” (investors, board members, entrepreneurs, etc.) served me well when I was getting started with Endeavor. I even waited for a potential mentor outside the men’s room once, just to get a few minutes of face time with him. [The opener was] “Hi, my name is Linda, and I’ve started an organization to support entrepreneurs in emerging markets. I’d love to come by your office for a few minutes to tell you more about it.”

Get over the sense that you might be perceived as aggressive. Women especially have to learn this. Estée Lauder was one of the greatest stalkers, and many other successful entrepreneurs got their start not with huge existing networks, but with a little well-placed chutzpah. Find a little courage and reach out to a mentor you admire. People respond to passion and a clear articulation of why you are approaching them in particular. The victim of my stalking did: He ultimately agreed to co-chair Endeavor’s global advisory board. In other words: Stalking is an underrated startup strategy!

What advice would you give to a smart, driven college student about to enter the “real world”? What advice should they ignore? People always tell recent graduates and budding entrepreneurs that they should keep their options open; “don’t close any doors.” But keeping every option open winds up leading to paralysis or, worse than that, self-deception. How many of my former classmates who took a job at Goldman Sachs or McKinsey for “a few years” before they pursued their real passions like cooking or starting their dream company are actually now chefs or entrepreneurs? Most are still banking and consulting, believing that those doors are still open. My advice to college students: Close doors.

This advice also applies to entrepreneurs who have one foot in the business and one foot out. That’s okay at the outset (heck, Phil Knight of Nike worked as an accountant for years, and Sara Blakely of Spanx sold fax machines until she was certain her idea would take off). But at some point after your idea has launched, 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 to entrepreneurs: Once your idea has gained traction, cut the umbilical cord. Your idea can’t take flight if you don’t leave the nest.

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