In 2014 Jennifer Fitzgerald (NYO 08-13) co-founded the insurance shopping platform Policygenius with fellow alum Francois De Lame (JOH, NYO 04, 06-08, 12-14). Their goal was to improve the process of buying insurance by creating a platform centered around the user, making it easy for consumers to comparison shop and understand exactly what it was they were buying. 

This year, she’s been named to Fast Company’s eagerly anticipated list of the 100 most creative people in business, in part because of a recent outdoor ad campaign for Policygenius that played on the New York subway’s “Poetry in Motion” series. Ads with cheeky blank verse appeared in several major metropolitan areas in the U.S. – and yes, on the New York subway. 

One example: "Poetry / is hard / because / you never know / when to / begin / a new line. / But you must, or / it's just / a regular sentence. / Thankfully comparing / life insurance online is easy. / Maybe do that instead."

Jennifer launched the campaign not only to attract attention, but also to save marketing dollars – “insurance” being one of the most expensive key searchwords. “Nobody’s going to stop and engage with an insurance ad on Facebook,” she told Fast Company.

The creative stroke is probably not surprising from a woman who also does stand-up comedy in her spare time.

Fellow alum Paul Arnold (SVO, SFO 08-12), one of Jennifer’s investors, says of her: "Jen is the real deal. I like her because she a great person. But I invested in her because she's an innovative founder and a brass-tacks operator who makes things happen."

Jennifer was recently profiled in Forbes as one of a handful of women entrepreneurs who have raised $50m in funds. In 2016, she was named to Built In NYC's list of the top 50 women founders in New York.

This week, she answered a few of our questions. What’s harder – entrepreneurship or stand-up comedy? This is your chance to find out.

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Your recent outdoor ad campaign in major metropolitan areas featured humorous poetry. Did you help compose the poetry? How confident were you that the campaign would work?

The riff on the NYC subway's "Poetry in Motion" series was my idea, but I didn't compose the poetry. Our creative director did – and did an incredible job. I was pretty confident the campaign would stand out on the NYC subways because I hadn't seen it done before, and I knew our creative team would do an exceptional job in the execution. 

You do stand-up comedy occasionally. What’s harder: entrepreneurship or comedy?

Entrepreneurship is a thousand times harder. If you bomb on stage as a comedian, you just let down yourself and the fifteen people in the audience, who will soon forget how terrible you were. If you fail as an entrepreneur, you let down your employees, your investors and even your own mother (she was one of Policygenius’s early angel investors). 

What’s the last book you read?

The last non-business book I read was "I'll Be Gone in the Dark" by the late Michelle McNamara about her obsessive search for the Golden State Killer. I'm a true crime junkie and this was a fascinating story about the persistence of a small group of people in their decades-long hunt for the killer. The author unexpectedly passed away before the book was published, and just a short time later the police caught the killer when a genealogy website yielded a familial link to the killer's DNA sample. The last business book I read was "Inspired: How to Create Products Customers Love." It's become one of the go-to books for tech product companies.  

What's your favorite McKinsey memory?

There are too many to pick just one. My mini-MBA in Kitzbühel in 2008 was a special time – I met people there who are still probably my closest friends today. I enjoyed being a roast master at the Partner election dinners of people like Chad Slawner and Jed Finn. Oh, and it was great to roll off the study where I and everyone else on the team put on about 10 pounds of stress weight. That was a very happy day. 

What’s your weirdest party trick / talent?

I am practically unbeatable in music trivia. Play a song that came out between 1960 and the 2000s in any popular genre – pop, rap, rock, country, etc. – and odds are I can name the artist. Play 20 songs and I'm pretty sure I can go head to head against anyone and come out the winner. This is a pretty useless skill except in pub trivia.

Where do you see yourself in five years?

In five years, I'll still probably be working on Policygenius, and living somewhere overpriced in Brooklyn!