The Book That Inspires a Rising Star Entrepreneur

It turns out that Jennifer Fitzgerald of Policygenius is a fan of American history.

Colleen DeBaise By Colleen DeBaise

It's a surprising addition to the list of inspirational books for women entrepreneurs. (Photo credit: Unsplash)

It’s a surprising addition to the list of inspirational books for women entrepreneurs. (Photo credit: Unsplash)

I recently had the good fortune to sit down with Jennifer Fitzgerald, co-founder of buzzy insurance startup Policygenius, for a long conversation about rejection, sexism and other obstacles she’s overcome in her entrepreneurial journey (to date).

Fitzgerald is a rising star in the New York tech scene. Quartz ranks her 44th on its Founders Index of 250 female founders. Forbes notes she’s one of only five women in fintech (finance technology) to have raised over $50 million. In 2014, Fitzgerald launched Policygenius with the goal of making insurance shopping easy for millennials who don’t have the time or inclination to meet with brokers in-person.

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Jennifer Fitzgerald of Policygenius is inspired by Team of Rivals: The Political Genius of Abraham Lincoln by Doris Kearns Goodwin. (Photo: Courtesy of the company)

Jennifer Fitzgerald of Policygenius is inspired by Team of Rivals: The Political Genius of Abraham Lincoln by Doris Kearns Goodwin. (Photo: Courtesy of the company)

So where does a next-generation leader like Fitzgerald get her inspiration?

It turns out, she’s a fan of history — particularly, Abraham Lincoln. She recently read Team of Rivals: The Political Genius of Abraham Lincoln by historian Doris Kearns Goodwin that illuminates Lincoln’s rise from obscurity to the presidency. “It’s great,” Fitzgerald says. “It was how he built his cabinet, his team, through the most trying time in this country’s history.”

Indeed, the book details how Lincoln beat out three gifted rivals for the presidency — William H. Seward, Salmon P. Chase and Edward Bates — and then proceeded to bring his disgruntled opponents together to form the most unusual cabinet in history. As a result, he was able to marshall all of their talents to preserve the Union and win the Civil War.

“It’s kind of a cliché. Every CEO I know has read that book,” Fitzgerald says, “but it’s really good. It has a lesson in leadership.”

The book comes in at No. 8 on this list of 52 books recommended by Fortune 500 CEOs — somewhat surprising, considering it’s not a traditional business book, like Jim Collins’ Good to Great or Michael Porter’s Competitive Strategy. Many fans of the book, however, say that Lincoln’s ability to manage people is instructive and inspiring. After all, CEOs who can create great workplaces (think Zappos’ Tony Hsieh) and communicate their vision effectively (think Apple’s Steve Jobs) are often the ones who reach the highest pinnacle of success.

Fitzgerald says she keeps all this in mind as she works hard to make her workplace positive and collaborative for her 140 employees. She recently moved into a new open-floor-plan space in Manhattan’s Flatiron district, where a “Legend” wall is covered with photos of staffers who have won the company’s quirky Michael Jackson Legend Award for excellent performance. The company has weekly meetings, a training program for new hires, quarterly problem-solving workshops, and an annual off-site meeting. The company also hosts events for relationship building, such as special programs during New York’s “Pride” week for LGBTQ employees.

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These days, Fitzgerald says she spends a good chunk of her time making sure the company, which was recently valued at $130 million, hires people who are a good fit. “We are hiring a lot across the company, so I spend a lot of time speaking to candidates, sitting in on interviews,” she says. Employees are expected to follow the company’s six core values or mantras, including “live by the golden rule” and “life’s too short to be salty.”

Before starting Policygenius, Fitzgerald studied improv with the Upright Citizens Brigade — something she recommends to other CEOs. “If you’re a CEO or a founder, a lot of your job is sales and storytelling,” she says. “You’re continuously motivating the company, getting them excited about your vision and strategy. If you are uncomfortable speaking in public, that’s gonna be very tough to do.”

I mention that Doris Kearns Goodwin, who wrote the book on Lincoln, has an extraordinary gift for storytelling and making history come alive. “Absolutely,” she agrees. In fact, if Fitzgerald were to have dinner with anyone, alive or dead, Lincoln would come first — but Goodwin would be a close second.

Read my full interview: This Founder Didn’t Let Rejection or Sexism Stop Her From Building a $130 Million Insurance Startup

Posted: November 29, 2018

Colleen DeBaiseThe Book That Inspires a Rising Star Entrepreneur