The smartest entrepreneurs aim low when picking a mentor

Rent the Runway co-founders Jenn Hyman and Jenny Fleiss have advice for fellow entrepreneurs.
Rent the Runway co-founders Jenn Hyman and Jenny Fleiss have advice for fellow entrepreneurs.
Image: Reuters/Shannon Stapleton
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You can learn a lot from the Mark Zuckerbergs and Elon Musks of the world, but not much of it will be practical.

Sitting in Starbucks or in your day job at a big company, your dreams of starting a business feel very distant from the experience of these founders-turned-cultural-icons. But if not billionaire founders, who else should early-stage entrepreneurs follow?

According to the founders of Rent the Runway—the luxury-clothing rental company that earned $100 million in revenue in 2016, and is reported to be valued at $1 billion—while the nation’s top CEOs have lessons worth learning from, the smartest entrepreneurs aim lower when searching for mentors.

CEO Jenn Hyman and her co-founder Jenny Fleiss explained this perspective, rooted in their own experience, at the 2017 Project Entrepreneur NYC Summit, a meet-up of over 200 women founders co-hosted by Rent the Runway Foundation and UBS.

“When someone is too senior, or too far away from the stage that you’re in, they become inspirational, but they stop being helpful,” Hyman said. “[W]hat Jenny and I needed at the beginning of our company was tactical help. I mean, I remember that we didn’t understand or know in the early days how were we going to pay our employees, how do benefits work, how do you pick what PR firm to work with.”

The entrepreneurs who were most helpful to Rent the Runway in its early stages, Fleiss said, were those who just a few years earlier had lived through the exact problems she and Hyman were asking about.

As an entrepreneur seeking to be taken seriously—and, sometimes, funded by top-level entrepreneurs—it’s easy to feel stupid asking such tactical questions to people who are far more senior, and successful, than you and your company are, says Hyman. This problem is particularly challenging for women, and especially women of color, who are significantly less likely to receive venture-capital funding than their male counterparts. This is why Hyman and Fleiss created Project Entrepreneur, a network for women helping other women scale their companies.

Often, the best way for an entrepreneurial mentor to help another founder is to just pick up the phone, answer basic questions, and connect her to powerful people. Hyman offered the example of a seed-stage founder she had met with just days before the event. She helped re-write her fundraising deck and plans to go with her to pitch investors, sales being one of Hyman’s strong suits and something the founder she’s mentoring, a scientist by training, struggles with.

That’s the type of assistance that founders who’ve met with early-stage success are in a great position to provide. “To be in the [most successful] moment of building a company is actually when you’re most able to help other entrepreneurs,” Fleiss said. 

So, rather than being paralyzed by one’s lack of connections to crazy-successful founders who’ve long-surpassed the startup stage, entrepreneurs can take comfort in the reality that their most effective mentors are far closer in reach.