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 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 the 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: When and why did you decide to write Crazy Is a Compliment?

Rottenberg: In my experience, some of the biggest obstacles to becoming a successful entrepreneur aren’t financial or structural—they are internal and psychological. A few years ago, I set out to write Crazy Is A Compliment to help people overcome those mental obstacles to success. It’s important for dreamers to believe in themselves and their ideas, to fend off the skeptics and find others who will share in their dreams. Once you understand that being called “crazy” is a compliment, you realize that you can get beyond other people’s opinions and zig when others zag. Nowadays, everyone has to learn to think and act more like an entrepreneur, and my book serves as a roadmap to getting started.

Morris: Were there any head-snapping revelations while writing it? Please explain.

Rottenberg: While I started out writing a book to help everyday people learn to think and act more like entrepreneurs, I found that deep down I was also writing for my twin daughters Tybee and Eden. I especially wanted to prepare them for the world they’re about to enter, where careers paths are no longer straight; ladders have tumbled; and rats are less willing to run someone else’s race. They inspire me to go home every day so, as much as this book is for regular people, it also became a very personal pursuit.

Morris: To what extent (if any) does the book in final form differ significantly from what you originally envisioned?

Rottenberg: When I first sat down to write the book, I didn’t know exactly what the end-product would look like but I knew what I didn’t want it to be – it wouldn’t be a how-to manual for writing a business plan, an academic primer on the history of entrepreneurship, an inspirational graduation speech filled with feel-good bromides or a story of one person’s journey to success. Instead, I was going to try to offer an entrepreneurial roadmap, mined from my research and experience. What surprised me, however, was the sheer number of stories that I had never heard of – Veuve Clicquot, Pepperidge Farm, Burt’s Bees – that don’t often get told because they don’t follow the standard narrative of a college drop-out techie in a hoodie living in Silicon Valley. As I got deeper into my research, I felt an intense desire to bring these lesser-known stories to life.

Morris: Please explain the title.

Rottenberg: I was called “la chica loca” 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, you should expect to be called nuts. You can’t rock the boat without being told you’re off your rocker. Entrepreneurs’ greatest asset 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!

Morris: You identify four species of entrepreneur. What are the defining characteristics of each? First, Gazelles

Rottenberg: This is the classic entrepreneur of myth and reality, someone who starts a new business venture and aims for it to explode into a white-hot phenomenon. They are fast moving and jump high.

Morris: Skunks

Rottenberg: Skunks are also called intrapreneurs – those who start something new inside an existing large company. These are entrepreneurs who go out of their way to stink up the joint!

Morris: Dolphins

Rottenberg: Dolphins are contrarians in the non-profit and public sector, community groups, and social service organizations. They fight for change and new ideas that the establishment is slow to adopt or reluctant to even consider.

Morris: Butterflies

Rottenberg: Butterflies are the fastest growing group of all. These are small-scale or lifestyle entrepreneurs: the plumbers, yoga instructors, freelance writers, organic farmers, and artists. Forty percent of the American adults are working on their own, and 24 million more are expected to be self-employed in 2018.

Morris: Here are the names of five entrepreneurs. Which species? How so? First, Benjamin Franklin

Rottenberg: A politician, statesman, scientist, inventor, printer and author…is there anything Ben Franklin couldn’t do? For this reason, it’s almost impossible to categorize him as a single species. He is both a butterfly, who single-handedly produced some great inventions, and a dolphin, who shaped and guided the birth of this great nation.

Morris: Sam Walton

Rottenberg: A gazelle. We think of one-stop shopping today as a no-brainer business model but when Sam Walton first had the inspiration to create a discount store at age forty-four, his brother dismissed it as “just another of Sam Walton’s crazy ideas.” Walton is a great reminder that gazelles do not necessarily have to be technopreneurs.

Morris: Mary Kay Ash

Rottenberg: A skunk-gazelle. Mary Kay started out as a saleswoman for a household goods company where she had the innovative idea of hosting parties to encourage people to buy her wares. She then struck it big on her own, taking a bet on a new cosmetics formula that she marketed into a billion-dollar business.

Morris: Ted Turner

Rottenberg: A dolphin-gazelle. Turner was a pioneer in the media world, launching the first 24-hour cable news channel and the first superstation, among many other bold ventures, which sometimes overshadow the great philanthropic and environmental work he also did on the side.

Morris: Ron Popeil

Rottenberg: A butterfly. Popeil managed to build a personal brand for himself by coming up with dozens of gadgets and gizmos as well as the marketing slogans to sell them on TV. As a result, he is recognized today as the father of the infomercial. Popeil is a great example of how tiny butterflies can have an outsized impact even without a massive company behind them.

Morris: As I indicate in my review of the book for various Amazon websites, there are dozens of passages throughout your narrative that caught my eye. For those who have not as yet read the book, please suggest what you view as the most important point or key take-away in each of these passages.

First, Suzanne Senglemann (Pages 22-25 & 202-203)

Rottenberg: Two “skunks” at Clorox who combined their jobs into one, Suzanne Sengelmann and Mary Jo Cook, eventually went on to create Clorox Green Works, a line of eco-friendly cleaning products. Despite their fear of failing as high-profile female executives, they eventually grew the Green Works line into a $60 million a year business, and demonstrated that you can’t wait for others to give you permission to take those big risks.

Morris: Thomas Edison (30-32)

Rottenberg: When Edison first started out with his “crazy” idea for the light bulb, skeptics were unmoved. They called Edison a con man and taunted him to prove his bulb could really work. Despite the naysayers, Edison pushed on, demonstrating the importance of sticking with his “crazy” idea which would go on to turn him into one of the world’s most well-known entrepreneurs. The key here is to fan the foolish fire no matter what!

Morris: Richard Branson (43-44)

Rottenberg: Richard Branson wrote in his own book, Losing My Virginity, “If you are a risk- taker, the art is to protect the downside.” When we honored him at one of our annual Endeavor galas, he told the story of his ill-fated foray into soft drinks, Virgin Cola. In Branson’s telling, Virgin Cola was a disaster, but it was a “contained disaster.” It was the result of a calculated entrepreneurial risk that didn’t threaten the Virgin brand. In short, he didn’t bet his entire farm, but instead wagered just a few chickens, wisely taking the risk out of risk-taking.

Morris: Friends and Family: In business and on test-driving ideas (49-53, 116-120, and 163-164)

Rottenberg: One of the biggest lessons when it comes to working with friends and family is to have the confidence to fire your mother-in-law if need be. The way to keep issues with loved ones out of the boardroom is to create what I call a start-up prenup, a document that puts the rights and responsibilities of each partner on paper. Just as it can seem inconceivable for a young couple in love to plan in case of divorce, so it can seem awkward and insulting to draft a formal contract between a parent and a child or two best friends from childhood. But too often I’ve seen the dreadful alternative. My advice is formalize your partnership agreement. It’s OK to start a business with those you love, but make sure you have a plan if the love goes away.

Morris: Edgar Bronfman, Jr. (65-66)

Rottenberg: Edgar Bronfman, Jr. became the board chair of Endeavor in 2004. At the time he told me that Endeavor needed to grow much faster. He said that we needed to move from being “charming” to being “relevant” and challenged me to expand from eight countries to 25 by the year 2015. I’m pleased to say that we will meet that goal by the end of this year! Edgar has served as both a mentor and role model, providing just the right mix of prodding and pushback.

Morris: Entrepreneurial personalities (89-109)

Rottenberg: I’ve worked with many entrepreneurs over the years and have found that they often fall into one of four categories:

o Diamond: Visionary dreamers leading disruptive ventures
o Star: Charismatic individuals building personality brands
o Transformer: Change makers reenergizing traditional industries
o Rocketship: Analytical thinkers making strategic improvements

Morris: Jeff Bezos and Amazon (126-127, 157-158, and 208-209)

Rottenberg: Jeff Bezos is the quintessential rocketship. In 1994, he was a senior vice president at a New York financial firm when he realized he wanted to be part of the Internet movement. But instead of leaping into his passion, Bezos followed a methodology, which eventually led him to start Amazon. Once under way, he continued his focus on data, analysis, and efficiency. He sweated the small stuff. He built Amazon into a company known for its efficiency that, while a boon to consumers, sometimes chafed employees. Bezos thrives on conflict. He prefers an adversarial work atmosphere to one based on cohesion. Rocketships may have formidable minds, but sometimes they give those around them headaches.

Morris: Agility (136-141)

Rottenberg: From a programming concept known as Agile, this leadership approach involves dividing workers into small teams, meeting daily to review progress, experimenting liberally, and succeeding or failing quickly. Today agile is standard practice in a hundred countries, and its techniques also have flooded into management suites, from Google to Facebook to TED. Agile leaders encourage their teams to adjust and experiment constantly. Second, agile leaders organize their workers into small, self-managed teams. Third, they are not afraid of the F word: failure.

Morris: Mentors (157-177)

Rottenberg: The image of a completely self-reliant entrepreneur is irresistibly romantic, deeply entrenched, and completely misleading. Far more than others in business, entrepreneurs need help. Lots of it. A survey we did of Endeavor Entrepreneurs showed that in their opinion, the most valuable contribution to their success – outside of their team – came not from those who provided financing but from those who gave good advice. These days, you need one set of mentors early in your career and a different set later. You need mentors for leadership, mentors for brand building, and mentors for dealing with that pain-in- the-butt colleague who’s holding you back. You even need mentors who are younger than you to help you see what’s coming.

Morris: Purpose-driven workplace (181-203)

Rottenberg: Products, profits, and paychecks are not enough anymore. These days, society cares how you treat your own workers. Customers want to know you promote the same values inside your walls as you do outside; job hunters want to know you care about them before they send in an application. Your culture is your brand. You need to create an organization where your employees believe in what you do.

Morris: Culture Club (190-194)

Rottenberg: I became obsessed with finding the right way to let the wrong people go because for a long time I was not so good at finding the right people in the first place. To put it another way, I used to be bad at hiring, so I had to become good at firing. My experience with entrepreneurs has led me to believe that there are better and worse ways of doing this.

First, working with founders in emerging markets, I learned that most people live and work in small worlds. Your employees are also your former classmates, your neighbors, etc. Second, in the age of social networks, even an ex-employee is still a spokesperson for your brand. Nothing defines your culture more than how you treat people, even those you no longer need or want around.

Morris: Get Going (206-212)

Rottenberg: A lot of people will tell you the first step to starting something new is to have an idea. I don’t agree with that. To me the first step starts long before that. It’s a commitment to looking at the world through rainbow-colored glasses. The first step to acting like an entrepreneur is to look not at the writing on the wall but at the spaces between the writing. It’s in the gap between what’s being said (or done) and what’s not being said (or done) that entrepreneurs thrive. The way to get going is to find the courage to take your dream out of your head and put it to the test in the real world. Don’t just think it; act on it.

Morris: Go Big (212-216)

Rottenberg: The second key skill you’ll need to bring change to the world will really test your creativity, as well as your sanity, your patience, and your resolve. It has to do with how to take your dream and make it as real as possible. It doesn’t really matter what your dream is, “going big” means doing it to the utmost. To do that, you need one thing: other dreamers to share your dream. If you learn to make your dream a team effort, you’ll find the key to growing big.

Morris: Go Home (216-221)

Rottenberg: The most important lesson of all: Go home. Make time for the ones you love. The easiest thing to think about living like an entrepreneur is that these skills apply to only one part of your life: your job. That’s a mistake. In the same way that entrepreneurs are redefining many of the traditional rules of the workplace, they’re also helping to break down one of the most stubborn boundaries of all, the one between work and family. While it’s popular to say you can have either a successful career or a meaningful personal life, I’d like to suggest you can aim for both.

Morris: Of all the great innovators throughout history, with which one would you most want to share an evening of conversation if it were possible? Why?

Rottenberg: I would love to sit down with Veuve Clicquot, whose story particularly captivated me when researching for the book. As a young widow, she was left to manage the family vineyard, subsequently revolutionizing the champagne industry, becoming an international luxury brand and getting both the Russian and French armies wasted. Even as far as entrepreneurs go, she took an unusual number of risks, from fraternizing with the enemy to smuggling goods and running a blockade. I would love to know how she mustered the courage to do all of this. At the very least, we would share a great glass of champagne!

Morris: In your opinion, what are the defining characteristics of a workplace culture within which entrepreneurship is most likely to thrive?

Rottenberg: In the first two sections of my book I talk about what it means for entrepreneurs to get going and go big. But there’s a third component to living like an entrepreneur. It begins when you focus on a series of larger questions: What purpose am I trying to achieve? What’s the meaning behind what I’m doing? This calls for creating a purpose-driven workplace that doesn’t just maximize efficiency but is infused with values. Today, entrepreneurs are at the forefront of a new era in which organizations put talent at the heart of their business models. And they have no choice. Having grown up surrounded by entrepreneurial freedoms, workers expect flexibility. They insist on collaboration. They demand meaning. Creating an environment that brings out the entrepreneurial instincts in your workforce – a worldview we might call “employeeship”- is key.

Morris: Let’s say that a CEO has read and then (hopefully) re-read Crazy Is a Compliment and is now determined to establish or strengthen a workplace culture within which personal growth and professional development are most likely to thrive. Where to begin?

Rottenberg: The first major issue I feel you need to consider when focusing on today’s workers: You have to know what motivates them. If you think it’s primarily money, think again. The biggest single change in the workforce of the entrepreneurial age is the list of priorities workers bring to the job. Paycheck is on the list, but it’s increasingly crowded out by a host of new considerations: impact, freedom, quality of life. The days when leaders could rely on their natural charisma and brilliant ideas to compensate for creating brutal places to work are over. Employees today have higher expectations; they are looking for what I call “psychic equity,” which is especially true for the bookend generations (older workers and younger workers). Neither generation rates money as the most important form of compensation and, if they can’t find that package, they’ll walk. In other words, make your workplace more entrepreneurial and flexible or find your workers fleeing to launch enterprises of their own.

Morris: For more than 25 years, it has been my great pleasure as well as privilege to work closely with the owner/CEOs of hundreds of small companies, those with $20-million or less in annual sales. In your opinion, of all the material you provide in Crazy Is a Compliment, which do you think will be of greatest value to leaders in small companies? Please explain.

Rottenberg: Over 17 years with Endeavor, I’ve noticed a few key traits that successful entrepreneurial leaders learn to do right. Agile leaders encourage their teams to adjust and experiment constantly. In today’s age of (over)sharing, the best leaders also have to be more open and accessible. To be effective, you also have to be aware of how others perceive you and cop to your flaws every now and then. The final lesson to successful leadership may be the most challenging and most important of all. Expose yourself. Allow yourself to be vulnerable—less super and more human. These “Leadership 3.0” practices, as I call them, are critical to being an effective manager when you’re getting started in today’s world.

Morris: Which question had you hoped to be asked during this interview – but weren’t – and what is your response to it?

Rottenberg: One question that I never dreamed of getting but that has started to creep up comes from readers who ask me, “So how do I become crazy?” They have seen how being crazy can actually propel one’s professional career and they lament that they are not entrepreneurial enough to compete with the Mark Zuckerbergs of the world. And that is both probable and desirable. You can be “crazy” on a much smaller and more significant scale – on the 5-inch course between your ears, to paraphrase the great golfer Bobby Jones. To me being crazy is a combination of being curious and courageous: Having the intellectual pluck to ask why? then why not? and finally what if? Being an entrepreneur means looking at the world not as it is, but as it could be.

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To check out Part 1, please click here.

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

Her website link

Twitter link

Endeavor link