Jason Feifer: The Entrepreneur’s Storyteller

Jason Feifer

Reached by phone at the midtown Manhattan office of Entrepreneur magazine, Jason Feifer confesses that he’s in the middle of a “crazy afternoon.”

Perhaps that’s to be expected. Feifer is not only the editor in chief of Entrepreneur, but he’s also the host of not one but three podcasts, as well as a frequent event speaker. He recently served as emcee at Babson’s Centennial Celebration, feeling at home before a crowd enthusiastic about entrepreneurship. “It was great,” he says. “I really appreciate Babson’s welcome of me.”

In a brief moment of calm during his crazy afternoon, Feifer took time to talk about the enduring power of print, his need to find new opportunities, and what he admires about the many entrepreneurs he has met. “I find entrepreneurs are the best kinds of problem solvers,” he says. “I love how they think. They are really good at breaking down a situation and coming up with counter-intuitive solutions. I find that inspiring.”

The Famous and the Unknown

As a speaker, Jason Feifer serves as a shot of caffeine at gatherings. At Babson’s Centennial Celebration, he filled the stage with energy and excitement, even stopping at one point to snap a selfie with fashion designer Diane von Furstenberg, one of the event’s many featured speakers. “It’s very cool to meet famous entrepreneurs,” he says. “I use their words of wisdom all the time.”

From von Furstenberg, Feifer took one message in particular to heart—that every successful person, no matter how much he or she has accomplished, still feels like a “loser” at least once a week. “I love that,” Feifer says. “I’ve already repeated it 10 times to other people.”


As much as he likes meeting famous entrepreneurs, though, Feifer says that the stories of hard-working, unsung entrepreneurs, those who never end up on magazine covers, leave a lasting impression on him. “Those everyday stories of companies facing challenges really stick with me,” he says. “Everyone goes through so much of the same things.”

One memorable entrepreneur whom Feifer has interviewed is Sam Calagione of Dogfish Head Craft Brewery. Years ago, the Delaware brewery had a hit beer, the 60 Minute IPA, that was easily the brewery’s biggest seller. That popularity posed a problem, however, as Calagione worried that his brewery would be known for only one type of beer. If tastes changed, he would be sunk. “Often the thing that makes you win the first inning makes you lose the game,” Feifer says.

Calagione decided to limit production of the best-selling 60 Minute IPA so that customers might seek out the brewery’s other beers instead. That was a gutsy decision, painful in the short term, but the brewery continued growing in the years to come. This year, Boston Beer Co. purchased Doghead for $300 million. “Entrepreneurs play the long game, even when it hurts,” Feifer says.

Embracing Change

After talking with many, many entrepreneurs, Feifer says what he probably admires most about them is their ability to embrace change. He knows that’s not easy to do. “Like anybody, I can react negatively to change,” he says. “As much as I preach embracing change, I fall victim to that negativity.”

Accepting change is something Feifer must regularly do as the editor in chief of a print publication in our digital age, though he says a well-made magazine can still stand out from the web’s cacophony. “I see a lot of value in continuing to do a print publication. The kind of storytelling people value is done best in a less distracting environment,” he says. “Right now, I see a lot of reader engagement, and our ad sales have been way up this year.”

But Feifer knows that print remains an industry in flux, and that’s a big reason he does his podcasts: Pessimists Archive, which looks at the fears of new technologies through the years; Hush Money, which examines tricky money situations in our lives and careers; and Problem Solvers, which explores the daunting problems that business owners and CEOs have faced.

“I want to be where the new opportunities are,” Jason Feifer says. “I love storytelling. I love how I can use my voice and connect with an audience in a totally different way. It’s a thrilling new medium. To be a person who survives in a changing enterprise, you have to be ever changing as well.”

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