A Pep Talk from a Risk-Taker

Linda Rottenberg, the founder of a global organization helping business innovators, shares wisdom about making an entrepreneurial mindset part of our lives.  

by Sue Tomchin

If you’ve ever fantasized about starting your own business or even if you haven’t, Linda Rottenberg’s new book is an essential—and inspiring—read. Crazy Is a Compliment: The Power of Zigging When Everyone Else Zags (Penguin), challenges all of us to think and act like an entrepreneur because being nimble, adaptive and daring is an essential part of making it in today’s world—whether we work for ourselves, a Fortune 500 company, or a nonprofit organization. “Change is the only constant,” she writes. “We all need the skills required to continually reinvent ourselves,” to “take some risk or risk being left behind.”

Rottenberg is the CEO and co-founder of Endeavor, a global organization that identifies, mentors and co-invests in business innovators demonstrating potential for growth. Though it now has 350 employees and 20 affiliates throughout Latin America, the Middle East, Southeast Asia, Africa and Europe, like many start-ups, Endeavor began two decades ago with a dream that she and business partner Peter Kellner boldly transformed into reality. Rottenberg made the leap into entrepreneurship despite the objections of others, in her case, her parents, who valued “steadiness and security” and who wanted her to use her Yale Law degree to pursue a more conventional career. When she faced that “juncture between doing what’s safe and expected and doing what’s uncertain and unknown,” she chose the latter.  

Rottenberg writes about entrepreneurship in a fresh and engaging way, challenging us to see it not only as the terrain of techies in hoodies, but of anyone undertaking a bold venture—from “improving your neighborhood to selling crafts out of your basement; from modernizing your family business to proposing a new initiative in your corporation.” 

Using real life examples, she shows us that many of the assumptions about starting new ventures aren’t accurate anymore. Is writing a business plan a necessity before starting a business? No. “Stop planning. Start doing,” is her advice. She cites the experience of Connecticut housewife Margaret Rudkin. When her son’s doctor told her that she needed to give the boy a natural foods diet, Rudkin got busy and perfected a loaf of homemade grain bread. Her son loved it and so did his doctor, so she took it to her local grocer. He bought every loaf she had with her, and then ordered more. Her company Pepperidge Farms was born. 

 Linda Rottenberg. (Photo by Tim Francis.)

Linda Rottenberg. (Photo by Tim Francis.)

Do you have to risk “the farm” to start a business? No, says Rottenberg, citing the experiences of self-made billionaire Sara Blakely, founder of Spanx. She “derisked the risk” in starting her business by keeping her day job selling copy machines, while marketing her figure enhancing panty hose on nights and weekends. She didn’t quit selling office supplies until she was “confident her entrepreneurial adventure would take off.” 

Using the story of another iconic entrepreneur, Ida Rosenthal, founder of Maidenform, Rottenberg shows how times have changed. While Rosenthal built a phenomenally successful business, giving women an innovative product that enhanced their lives and their figures, she “sped up her assembly lines and browbeat her union workers,” making her company a place where people didn’t want to work. Today, writes Rottenberg, “The biggest single change in the workplace 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.”

“Quality of life” is something that also applies to the entrepreneurs themselves. While you may be tempted to work 24 hours a day, Rottenberg’s advice is to “Go Big AND Go Home.” She writes that she learned this essential lesson from her daughters. One day, she had just finished packing and was preparing to leave for a business trip. As the cab pulled up her daughter Eden tugged at her leg and said, “Remember, you can be an entrepreneur for a short time, but you’re a mommy forever.” A final helping of wisdom from a valuable and engaging book. 

(Originally published in spring 2015.)