Linda Rottenberg: Part 1 of an interview by Bob Morris

RottenbergNamed one of “America’s Best Leaders” by U.S. News and one of TIME’s 100 “Innovators for the 21st century,” Linda Rottenberg is considered among the world’s most dynamic experts on entrepreneurship, innovation, and leadership. Her pioneering work also earned her a host of nicknames: ABC and NPR declared her “the entrepreneur whisperer,” Tom Friedman dubbed her the world’s “mentor capitalist,” Business Insider named her “Ms. Davos,” and for years she was known as “la chica loca” (the crazy girl) for insisting that entrepreneurs existed not only in Silicon Valley but also in emerging markets around the world.

Rottenberg is co-founder and CEO of Endeavor, the premier organization focusing on the scale-up phase of entrepreneurship. Headquartered in New York with 50 offices across the globe, Endeavor identifies, mentors, and co-invests in “high-impact” entrepreneurs: those with the biggest ideas, the likeliest potential to build companies that matter, and the greatest ability to inspire others. Since 1997, Rottenberg’s network has screened 40,000 candidates, handpicked 1,000 Endeavor Entrepreneurs, and helped them grow to provide 400,000 jobs and generate $7 billion annually.

Linda is also author of a New York Times bestseller, Crazy Is A Compliment: The Power of Zigging When Everyone Else Zags, published in October 2014. A graduate of Harvard University and Yale Law School, Linda lives in Brooklyn with her husband, author and New York Times columnist Bruce Feiler, and their identical twin daughters.

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Morris: Before discussing Crazy Is a Compliment, a few general questions. First, who has had the greatest influence on your personal growth? How so?

Rottenberg: My twin daughters, Tybee and Eden, have greatly impacted both my personal and professional growth. Just by virtue of being born they changed my whole leadership style. I used to be a perfectionist and a micromanager but I had to learn to let go and say no occasionally in order to be with them. As Eden wisely pointed out at the ripe young age of 5: “You can be an entrepreneur for a short time, but you’re a mommy forever!” It is for this reason that I encourage Endeavor employees and entrepreneurs to “go big and go home,” rather than choosing either-or.

Morris: The greatest impact on your professional development? How so?

Rottenberg: When Edgar Bronfman became chairman of Endeavor, he unwittingly became a mentor, both guarding my back and pushing me forward. And he did it without any recognition. One reason mentorship has become so central to who I am is that I’m forever trying to help others who find themselves in the same situation as when I felt most alone and someone stepped into the breach to help me.

Morris: To what extent has your formal education been invaluable to what you have accomplished in life thus far?

Rottenberg: At Harvard, I majored in social studies which taught me to care about the world and think holistically about its problems. It also introduced me to Joseph Schumpeter, the Austrian economist who argued that a nation’s “fiery spirits” (a.k.a. entrepreneurs) are its most powerful economic change agents as forces of “creative destruction.” I developed a passion for social activism and entrepreneurship then and there. And Yale Law School confirmed what I probably already knew, that I didn’t want to be a lawyer! Fortunately, my professors recognized this and gave me an opportunity in Latin America that led me first to join Bill Drayton’s Ashoka and eventually to co-found Endeavor with Peter Kellner.

Morris: Years ago, was there a turning point (if not an epiphany) that set you on the career course you continue to follow? Please explain.

Rottenberg: It was actually in the back seat of a taxi in Buenos Aires that I encountered my “crazy moment” and decided to start Endeavor. I was talking to my taxi driver and I learned that he had a Ph.D. in Engineering. So I asked him, “Why are you driving a cab? Why don’t you become an entrepreneur?” He said, “Become a what?” It turns out that the word “entrepreneur” was barely understood, let alone used, in the Spanish vocabulary. More importantly, there was no network, there were no mentors, and no access to capital there – all of which are critical to starting a business. So I partnered with a friend, Peter Kellner, and started organizing groups of successful entrepreneurs and business people who could help mentor promising entrepreneurs in Latin America. One of my proudest moments is when I learned from the editor of a leading Brazilian dictionary that, thanks to Endeavor’s efforts, the word empreendedorismo, or “entrepreneurship,” was being incorporated in the next edition.

Morris: What do you know now about the business world that you wish you knew when you went to work full-time for the first time? Why?

Rottenberg: I wish I had known how underrated stalking is as a startup strategy! My ability to ‘stalk’ (investors, board members, entrepreneurs, etc.) served me well when I was getting started with Endeavor. A certain amount of chutzpah is just as important as capital. I even waited for a potential investor outside the men’s room once just to get a few minutes of face-time with him. Get over the sense that you might be perceived as aggressive (women especially have to learn this). Find a little courage and reach out to a mentor you admire. People respond to passion. The victim of my stalking did: he ultimately agreed to co-chair Endeavor’s global advisory board.

Morris: Here are several of my favorite quotations to which I ask you to respond.

First, from Lao-tse’s Tao Te Ching:

“Learn from the people
Plan with the people
Begin with what they have
Build on what they know
Of the best leaders
When the task is accomplished
The people will remark
We have done it ourselves.”

Rottenberg: Entrepreneurs often want to be their own bosses, but no one can do it alone. You need a robust team of mentors, partners, and employees on the ground. We honor this principle at Endeavor in two ways: first, by connecting our entrepreneurs with a rich network of role models from which to learn and grow; second, by insisting that the businesses we support are embedded in their local communities and help grow the local economies.

Morris: From Howard Aiken: “Don’t worry about people stealing your ideas. If your ideas are any good, you’ll have to ram them down people’s throats.”

Rottenberg: I couldn’t agree more with Aiken! I’ve found that at every turn, someone (or, more likely, everyone) will call you and your idea crazy because if it’s any good it will disrupt the status quo. The job of the innovator is to push past naysayers and find a way to drive forward. Often the toughest naysayer is YOU. Before you worry about how to convince others that your idea is the greatest thing since sliced bread, make sure you have fully convinced yourself.

Morris: From Richard Dawkins: “Yesterday’s dangerous idea is today’s orthodoxy and tomorrow’s cliché.”

Rottenberg: Whatever their field, entrepreneurs are fundamentally in the business of disrupting the status quo, of forging a new path and envisioning a different future. But once their “crazy” ideas catch on and become the new norm, their work isn’t done. Though people are naturally resistant to change, change is the only constant. If you want to stay ahead today, you have to continuously reinvent yourself and your business or risk being left behind.

Morris: From Isaac Asimov: “The most exciting phrase to hear in science, the one that heralds the most discoveries, is not “Eureka!” (I found it!) but ‘That’s odd….’”

Rottenberg: The first step to becoming an entrepreneur does not happen in a laboratory, a conference room, or even a pitch session. That “crazy” moment happens in the mind. And not the part of the mind where the light-bulbs go off and the ahas are heard. It happens in the part where the darkness resides and the doubts cry out. It happens when you are exposed.

Morris: Here’s a brief excerpt from Paul Schoemaker’s latest book, Brilliant Mistakes: “The key question companies need to address is not ‘Should we make mistakes?’ but rather ‘Which mistakes should we make in order to test our deeply held assumptions?’ Your response?

Rottenberg: If you’re an entrepreneur you must be prepared to make mistakes, some of which are outside of your control. That said, contrary to popular opinion, most entrepreneurs aim to be risk-minimizers, not risk-maximizers. They take smart, calculated risks. Instead of betting the whole farm on an as-yet untested idea, they’ll wager a few chickens.

Morris: In your opinion, why do so many C-level executives seem to have such a difficult time delegating work to others?

Rottenberg: In the early years of leading Endeavor, I had the reputation of being a bad delegator. I was deemed mercurial, meddling, and reluctant to give up control. At the same time, I was being asked by various entrepreneurs for advice on managing a growing team. In my opinion, delegation is an especially hard skill for entrepreneurs to learn because many start out by breaking away from the crowd and striking out on their own. But, while a great idea is born from originality and individuality, it is implemented through collaboration and teamwork. I consider one of my greatest accomplishments to be learning how to let go and to let others co-own an idea.

Morris: The greatest leaders throughout history (with rare exception) were great storytellers. What do you make of that?

Rottenberg: A truly resonant message has the power to launch a revolutionary movement. The greatest leaders in history understood that the most effective (and cheapest) way to move mountains, armies and minds is by inspiring others towards a common vision. Entrepreneurs, especially those with what I call “diamond” and “star” personalities, are charismatic evangelists who capture the imagination of everyone they meet as they talk about revolutionizing people’s lives. They tell compelling stories.

Morris: Most change initiatives either fail or fall far short of original (perhaps unrealistic) expectations. More often than not, resistance is cultural in nature, the result of what James O’Toole so aptly characterizes as “the ideology of comfort and the tyranny of custom.”

Here’s my question: How best to avoid or overcome such resistance?

Rottenberg: The best way to overcome popular resistance is by not resisting it but instead working with it. As much as I like to encourage bold risk-taking and counter-cultural thinking at the beginning of a new venture, I also believe that entrepreneurs should periodically gauge public opinion and actually follow the crowd—after all, it will drive market demand. A great idea is useless if no one buys into it.

Morris: In recent years, there has been criticism, sometimes severe criticism of M.B.A. programs, even those offered by the most prestigious business schools. In your opinion, in which area is there the greatest need for immediate improvement? Any suggestions?

Rottenberg: Business schools are big on the business plan. Most people think that once you have your crazy idea, you should put it on the page to make it seem more real. You should add numbers, buzzwords, projections, graphs, etc. But in my opinion, those people are wrong. Research on a thousand Endeavor Entrepreneurs found two-thirds did not write formal business plans when starting their ventures, more than 80 percent launched their first product within six months, and nearly half changed their business model at least once. Stop planning and start doing. They key idea is that you can plan all you want, but it’s more important to take action!

Morris: Looking ahead (let’s say) 3-5 years, what do you think will be the greatest challenge that CEOs will face? Any advice?

Rottenberg: In an increasingly unpredictable world, CEOs will need to know how to best handle moments of instability. One thing I learned when working in unstable economies over the years is that stability is the friend of the status quo; chaos is the friend of the entrepreneur. When Endeavor surveyed two hundred entrepreneurs to identify their strengths and weaknesses, the most commonly selected strength was “I see opportunities where others see obstacles.” Instead of fearing chaos, leaders need to learn to embrace it. Entrepreneurs who succeed in times of turmoil manage to contain their fear or anxiety. They don’t succumb to the agitation around them; they stay calm, recognize the opportunities that the disruption around them creates, then seek to exploit them. They respond to challenges not with panic but with strategic precision.

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Linda cordially invites you to check out the resources at these websites:

Her website

Twitter link

Endeavor link

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