Melissa Kaufman has never shied away from a change of course. She left her postgraduate consulting job at IBM for a marketing position at Google. She then moved to YouTube, where she managed content partnerships, before finally entering the startup realm. She was the 15th employee at fashion company Polyvore, and one of the very first at Luvocracy, an online marketplace eventually bought by WalmartLabs.

“At that point, I was sick of building other people’s companies, so I built my own,” Kaufman said. Her agency Storylark, founded in 2012, was a pioneer in influencer marketing for the Pinterest and Instagram space.

After three years at Storylark, Northwestern recruited her to be the founding executive director of The Garage in 2015. She was in Chicago at the time with her husband as he finished up his last year of surgical training. What was supposed to be a yearlong mentorship gig turned into a seven-year journey of advising student entrepreneurs. In her time at Northwestern, Kaufman has worked with over 1,000 student teams, overseeing programs like The Tinker Program and The Residency Program and co-writing an entrepreneurial guide, “Founded,” to help students design, launch and grow their businesses.

Now, she’s giving island life a try. The 40-year-old is relocating to Hawaii on May 26 with her husband and their 4-year-old son. NBN talked to Kaufman about what drew her into the entrepreneurial world, what’s kept her at Northwestern for the last seven years and what her future holds.

This interview has been edited and condensed for length and clarity.

NBN: What’s your first memory of being an entrepreneur?

Kaufman: I’ve always been pretty entrepreneurial. When I was maybe 10 years old, I had a pet-sitting business in my neighborhood. When people traveled, I would take care of mostly cats and sometimes dogs. In college, I used to sell spring break trips on campus.

NBN: What experiences did you have at your own startup [marketing agency Storylark] that prepared you to advise student entrepreneurs?

Kaufman: It was really scary and lonely. There were really high highs and really low lows. I loved having a co-founder. That was the only reason we kept going as long as we did. I’d been interested in entrepreneurship since college, and I didn’t start a company until I was in my late 20s, maybe early 30s. The Garage has been an opportunity for me to build what I wish I had in college – a place with other people interested in starting new things, the support of mentors, free office hours with attorneys and accountants, which is really expensive if you’re on your own, and people like myself and my (five-person) staff who are here for the right reasons and want to help students.

NBN: What are your favorite student startups that you’ve worked with?

Kaufman: That’s like asking me “Who’s your favorite child?” They’re all my favorite. It’s really about the student and less about the idea. What I love to see most is when a student is working on the right idea. One of our students [McCormick third-year Charlotte Oxnam], who’s working on a project called Cue the Curves, was selected by Microsoft to do a national advertisement that aired during the Grammys. And it happened because she is a plus-size woman working on making the plus-size shopping experience more positive. She hasn’t quite figured out the business model, but she's the right person to be doing it, and she’s getting access to incredible opportunities.

NBN: What’s been your favorite memory at The Garage?

Kaufman: Some of my favorite memories are getting out of The Garage. Walking the floor of SpaceX with some of our students was really cool. Just this spring break, we took a group of students from our Little Joe Ventures Fellowship [a program that annually awards grants and travel opportunities to five NU students] to Arizona. We all stayed in a big Airbnb party house and did a week of retreat. For me, it was watching the students who probably wouldn’t naturally be friends on campus all bond and come together and support each other. It gives them such a strong foundation for the rest of their lives if they all keep in touch — to have this network of really smart, interesting people who I know are going to go on to do great things.

NBN: Do you have any advice for the next executive director?

Kaufman: I hope they continue to keep the laser focus on students. The Garage is an innovation space, so it should continue to evolve with the needs and desires and hopes and dreams of our students. It’s staying here late eating pizza with our students to hear what they’re thinking about and doing, understanding where the gaps are, understanding which students don’t feel comfortable here and creating programs and opportunities so that they do. We want The Garage to be a fun, inclusive community. Everything from buying a Nintendo Switch to what snacks we put out -- the devil is really in those details and getting those right.

NBN: What's next for your career?

Kaufman: I teach an in-person high school class right now for entrepreneurship [at North Shore Country Day School in Winnetka]. I’m continuing that [at Seabury Hall on Maui]. Beyond that, I’m going to have to figure out something entrepreneurial to do.

NBN: You’re clearly adventurous. You left well-established companies to found your own startup, and now, you’re leaving it all behind for a new adventure. How did you develop that mindset, and what have you learned from it?

Kaufman: My family and I really wrestled with the decision to move to Hawaii. It’s a radical life choice. But entrepreneurship has taught me that regardless of success or failure, it’s important that you work on a new project. Who knows where it’s going to lead? I don’t know if this is the right decision. It doesn’t have to be successful, though. I hope it is, but if it’s not, you’ve just got to lean into the journey and the adventure and trust your gut sometimes.

Thumbnail courtesy of Melissa Kaufman.