The Lure of Entrepreneurship

Resourceful Jewish women—some just out of college—are finding success and fulfillment in the challenging world of startups.

by Susan Josephs

For about a decade, Jessamyn Waldman Rodriguez dreamed of starting a company where women from all over the world could bake delicious breads inspired by their own culinary traditions. “I had this really good idea, but I kept thinking, ‘I’m not the person who should do this,’ ” she recalls.

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After years of working other jobs, including as a policy analyst for the United Nations, Rodriguez decided she could no longer suppress her “entrepreneurial urge.” Armed with her passion for baking and a mission to empower other women with culinary dreams, she launched Hot Bread Kitchen in 2007 from her apartment in Brooklyn, N.Y. She teamed up with two women who specialized in tortillas and sold their products to a local farmers market.

“When I started, I knew I wasn’t on the easiest path, but I realized that being an entrepreneur was the only path of professional fulfillment for me,” she recalls.

Some nine years later, Rodriguez presides over a thriving nonprofit bakery and business incubation program that produces and sells 55 different breads from its commercial kitchen while providing low-income, foreign-born women with valuable job training and opportunities for their own entrepreneurial advancement.

The entrepreneur is among a growing group of young Jewish women who have recently transformed their ideas and passions into multimillion-dollar businesses, nonprofit social enterprises, ambitious tech startups and online communities that have capitalized on the latest economic trends.

“What we’re seeing today are young women, many of them right out of college, who see entrepreneurship as a viable career option,” observes Hedy Ratner, founder of the Chicago-based Women’s Business Development Center (WBDC).

While some of these women grew up in entrepreneurial families and descend from generations of immigrant Jews who started new businesses in America, others became entrepreneurially inspired from their studies in top business schools. Still others, such as Rodriguez, gained valuable experience in other careers before becoming entrepreneurs. What they all have in common is an ability to identify a consumer need, the resourcefulness to turn a concept into a profitable reality, a deeply rooted work ethic and a commitment to giving back to their communities.

A New World

Today’s generation of young female entrepreneurs have “much larger dreams and wider concepts since we started out,” says Ratner, who founded the WBDC in 1986 and built it into the largest resource program of its kind in the country. “When I started this, women owned less than 10 percent of businesses in the United States and weren’t taken very seriously as business owners. Today, the credibility of women-owned businesses is far greater.”

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Jennifer Fleiss and Jennifer Hyman, for example, know what it means to be taken seriously. The co-founders of Rent the Runway (RTR) met as classmates at Harvard Business School and decided to start a company inspired by an idea Hyman had after her sister complained that she had a closet full of clothes but nothing to wear to an upcoming wedding. In 2009, they launched their online mail-order service that allows women to rent designer dresses at a fraction of the cost of the full retail price. As of January 2016, RTR has partnered with more than 200 top-name designers, has 5 million members and has secured more than $125 million in venture capital.

“We were both very persistent in getting meetings with designers and investors, and we were both very hands-on,” says Fleiss of RTR’s success. “Jenn and I were never afraid of doing the hard, dirty work of making sure the dresses got delivered and that everything happened on time and in the right way.”

Named by Fast Company magazine in 2011 as two of the most influential women in technology, Fleiss and Hyman belong to an entrepreneurial world that has radically shifted since Ratner started advocating for women’s entrepreneurship. Today, entrepreneurship programs have exploded in universities and business schools, while centers such as the WBDC and the New York City-based Thypin Oltchick Institute for Women’s Entrepreneurship offer workshops, mentorship and loan programs for aspiring female entrepreneurs.

And according to a study conducted by the Global Entrepreneurship Monitor (GEM), some 126 million women in 67 different economies started or ran new businesses in 2012.

Still Work to Do

Yet, that same GEM study also reported that women in the United States continue to face “covert discriminatory practices” when trying to start their own businesses. That includes difficulty in acquiring investors or struggling with social conditioning that causes women to underrate their entrepreneurial abilities.

“There’s still a lot of work to do when it comes to encouraging women to be entrepreneurs,” says Elana Fine, managing director of the Dingman Center for Entrepreneurship at the University of Maryland.

At the Dingman Center, male students far outnumber their female counterparts, and Fine believes that’s partly because women’s entrepreneurship still lacks mainstream visibility. “We haven’t yet had the female equivalents of a Steve Jobs or Mark Zuckerberg that can serve as role models,” she says of the famous founders of Apple and Facebook, respectively.

“You can’t be what you can’t see,” agrees Marjorie Feld, a history professor and the faculty director of the Center for Women’s Entrepreneurial Leadership (CWEL) at Babson College. “We need to see how other women have succeeded so we can remember that we can do it too.”

Feld believes that institutions such as CWEL, which offers programs designed to give female students “an edge in their training and networking,” should be established on many more college campuses. “If you look at leadership in top companies, it’s still largely male and white, which speaks to an urgent need for centers where women have access to mentors and role models.” She says that she’s proud to be part of the faculty at Babson College, which has the mission of empowering women to succeed in the business world.

Different Paths

But while only 10 percent of the top 100 business schools in the world have centers specifically for women, universities can still have a huge impact on aspiring female entrepreneurs. For Adi Bittan, a former lawyer who worked for the Israeli government, attending business school at Stanford University—where she found mentors and a network—literally changed her life. “One of the most important things about these schools is they show you other people who don’t seem that different from you who have succeeded,” she says. “And it encourages you to just go out there and do it, even if what you’re doing seems a little bit nuts.”

Adi Bittan presents her business plans to a panel of judges at Fortune Brainstorm TECH 2013. Photo by Fortune Live Media via Flickr.

After receiving her MBA from Stanford in 2008, Bittan embarked on an entrepreneurial path in the male-dominated tech industry of Silicon Valley; she eventually co-founded and became CEO of OwnerListens. Launched in 2011, Bittan’s company offers a mobile phone app that allows consumers to communicate with business owners directly as an alternative to posting negative reviews on Yelp and other sites. With $1.1 million so far in funding, the company has facilitated some 9,000 messages sent to nearly 6,000 businesses in more than 40 states.

“For me to start this business, it wasn’t only that I liked the idea, I had to believe there were other people in the world that could benefit from it,” says the thirtysomething entrepreneur, who interviewed hundreds of business owners throughout the country before concluding that her idea could be “a large, scalable opportunity.”

In addition to her Stanford education, Bittan learned about entrepreneurship from her father, who owned nursing and assisted-living facilities in Florida and exposed her to all aspects of the family business. “As a kid, I spent weekends answering the phones, talking to residents and handling the mail, and I watched the business grow from 200 beds to 1,000 beds. That’s where I first learned about customer service and how to find solutions to people’s problems,” she says.

Growing up in an entrepreneurial family also deeply influenced Karine Nissim Hirschhorn, the Los Angeles-based co-founder of the innovative pet boarding service DogVacay. Born in Israel and mostly raised in New Jersey, she would sit at the dinner table listening to her parents talk shop about their careers in the jewelry industry. “I was raised with this language about business, and that definitely gave me an understanding of what makes businesses work,” she says.

Now in her 30s, Hirschhorn got her entrepreneurial start when she graduated from film school in 2007 and founded a series of directing, acting and writing workshops to help pay off her student loans.

After she and her husband Aaron spent years “struggling” over how to best care for their dogs when they went out of town, they decided to start a business in which they offered to watch other people’s dogs at their home as an alternative to expensive kennels. Quickly, they started getting more business than they could handle. “We started to realize that what we were offering could be done on a much larger level,” recalls Hirschhorn of their idea “to create a marketplace and online community for dog lovers.”

Launched in the spring of 2012, by 2014, DogVacay had raised $47 million from investors, hired some 70 employees and connected thousands of dog owners with more than 20,000 carefully screened pet sitters in numerous cities across North America. Often billed as “the Airbnb for dogs,” Hirschhorn sees her business as a closer relative to child care services than the successful vacation rental site. “We take the customer service and vetting process very seriously,” she says, adding that firsthand experience of taking care of other people’s dogs also helped them build the company. “I really believe you have to live the business, inside and out, and in my case, that was being elbow deep in dog poop.”

Lindsay Pinchuk, a thirtysomething mother of two, is also living her business, the largest event company in the country for mothers and moms-to-be. Headquartered in Chicago and operating there as well as in two other cities, the now six-year-old Bump Club and Beyond has partnered with baby brands and retailers to host hundreds of dinners, brunches, prenatal fitness classes and other events where women can network and receive free products.

Lindsay Pinchuk. Photo by Edyta Grazman Photography.

Pinchuk got the idea for the Bump Club shortly before she became pregnant with her daughter. “I had a friend who was pregnant and wanted to meet other pregnant women, and she was very nervous about trying to do this on her own.”

With a lifelong knack for networking, Pinchuk remains hands-on in all aspects of her business, which includes cultivating relationships with brands and retailers, organizing events and strategically planning how to expand into other cities. Her favorite part of the job, however, will always be “when I’m sitting at one of our dinners and I see a table of women exchanging phone numbers. That’s really why I started this company, knowing we’re connecting people in meaningful ways,” she says.

Raised in Detroit, Pinchuk received a master’s degree in integrated marketing communications from Northwestern University and credits much of her entrepreneurial success to her prior career in advertising and sales for a variety of publications, including Redbook and Sports Illustrated. “My job was to find strategic advertising solutions for all these different brands. That kind of training gave me the ability to clearly target this audience of moms and be able to work with just about every baby brand out there,” she observes.

Like Pinchuk, Fleiss also gained valuable work experience in her former career. After graduating from Yale with degrees in political science and English, she worked on Wall Street as a strategic planner and founded her own online tutoring agency. “My past experience honed my problem-solving and analytic skills, which I exercise every day at Rent the Runway,” she says.

Fleiss, however, first acquired her entrepreneurial instincts growing up in New York City, where she ran her own lemonade stands and watched her father build his own real estate development company. “I saw my dad creating something from nothing and that really inspired me,” she says.

With a gift for “rallying people together and getting things accomplished,” Fleiss was immediately sold on Hyman’s idea for RTR because “I saw it was going to solve a problem,” she says, noting that their business model also reflected the trend “of renting and sharing that we were seeing with companies such as Netflix and Airbnb.”

Different Environments

Currently head of the company’s business development, Fleiss spends her days working on sponsorships and strategic marketing. Dedicated to “democratizing fashion and helping women feel their most beautiful and self-confident,” she also helps foster a female-friendly workplace where nursing mothers can retreat to a separate room and her almost 2-year-old daughter can visit. “At RTR, women can be their full selves,” she says, noting the atmosphere of her workplace “is very different from my experience on Wall Street.”

Women can also be their complete selves at Hot Bread Kitchen, where aspiring female entrepreneurs have grown their businesses and taken part in the job training programs. For Rodriguez, who manages 52 employees, “what’s been most rewarding is seeing how many of my staff members have matured professionally. Also, I love eating the bread from our incubator program … it is such tangible satisfaction to taste a gorgeous loaf of sourdough,” she says, tracing her passion for bread to “early, visceral memories of my mother baking challah.”

Rodriguez credits her success to “a clear vision, a willingness to do every kind of job and a firm belief that I can figure things out.” Growing up in Toronto, both food and social justice “were very much at the center of my family life,” she says. Her parents, both teachers, had been active in the Civil Rights Movement “and the values they inoculated me with definitely helped develop the commitments I have today,” she says.

Ultimately, Rodriguez loves that she splits her time between “paying attention to the bottom line of the business and the social mission of the organization.” And she echoes many of her entrepreneurial peers when she talks about how earning a profit and giving back to her community remain firmly intertwined priorities in her overall entrepreneurial vision.

Bittan can relate. “We really care about the business owners we serve, and changing the way that people communicate is a mission I deeply believe in,” she observes about OwnerListens. “I’ve always been a mission-driven person, where I believe it is my duty to do something productive for others.”

These days, Bittan can no longer imagine a life without entrepreneurship, even though she could have forged an “easier” path working for an established company such as Google or Facebook. That’s because “for me this is about so much more than making money,” she says. “This is about having an impact on the world.”

Susan Josephs is a freelance writer who lives in Venice, Calif.

(This article was originally published in winter 2013 and was updated in winter 2016.)

ENTREPRENEURS' WORDS OF WISDOM

Have you been dreaming of running your own business but feel overwhelmed by the prospect of getting started? JW asked seven entrepreneurs and entrepreneurial experts to share their top tips.

Jessamyn Waldman Rodriguez, Hot Bread Kitchen

Celebrate your successes—that is the only thing that is going to ensure you overcome the hardships.

Stay true to your vision—don’t be distracted, especially in the early years, by opportunities that are far from that vision.

Hire a good bookkeeper early. I still lament that I don’t have good records from my first year of sales. You’ll likely be too busy to do a good job yourself.

Jennifer Fleiss, Rent the Runway

Instead of bogging yourself [down] with the idea that you need to create a business plan in order to start a business, test your concept on the ground to see if it will resonate with consumers, and continue to iterate on your idea until it becomes the very best version of itself.

I would recommend finding a partner. Jenn and I have found that, while it is great to have someone by your side for the challenging aspects of starting a business, it is even more fulfilling to have someone there to celebrate the successes with.

Just go for it. Many people come up with brilliant ideas but don’t execute them because they think there are more risks than there actually are. If your concept doesn’t work out as planned, you will be able to find another job, so just put passion behind it and go for it.

Adi Bittan, OwnerListens

One mistake I see all the time is building something before you learn from your customer base. Get to know your customers; find out what will work and not work for them.

Don’t be afraid to fail. Failure is great because we can learn from it and do better the next time.

Find investors who have invested in women. I have also found that male mentors who have daughters are more likely to be helpful to you.

Karine Nissim Hirschhorn, DogVacay

Do something you already enjoy doing. Let your business grow from your passion.

Finding mentors and positive role models are one of the smartest things you can do when starting a business. Hearing from someone else how they did it can inspire you.

Surround yourself with people who believe in you.

Lindsay Pinchuk, Bump Club and Beyond

Don’t be afraid to ask for help. I could never run my company without help from my husband, mom and dad, the BCB team and the other moms who believe in Bump Club. It’s okay to ask for help when you need it, and take it if it’s offered.

Find a focus and stick to it. Don’t try to be everything to everyone all at once. A successful business grows organically based on a need. Identifying that need is half the battle.

Believe in yourself and what you’re doing. If you don’t, no one else will. If you do, the sky is the limit.

Hedy Ratner, founder of the Women’s Business Development Center

Do your homework before starting a business. Prepare, research and learn. But once you make the decision, do it.

Prepare to be a workaholic, especially in the beginning. Know you have to devote an enormous amount of time to developing a business and making it successful.

Make your own decisions, and don’t let others discourage you.