Entrepreneur in Residence Spotlight: Grace Van Hollebeke ’19

Two-time founder Grace Van Hollebeke ’19 (CALS) began her entrepreneurial journey as a junior. Three years after graduating, she sold her first company; three years later, her second. Today, she is head of brand and partnerships at Tern, the all-in-one platform for travel advisors.

At each step of her journey, the Pillsbury Institute for Hospitality Entrepreneurship played a pivotal role — whether through education, collaboration or access to industry professionals who became clients, mentors and investors in her businesses.

“Pillsbury was the place where the concept of a startup became feasible to me,” she says.

Now she is paying it forward.

The entrepreneur

A communications major, Van Hollebeke landed a copywriting internship at JetBlue the summer after her sophomore year and found herself “writing funny, pithy content. At the end of the summer, I was like, ‘Travel is incredible. How do I get more involved in this?’”

As she looked for a travel-related job on campus, she came across MilesAhead, a travel agency startup founded by Rob Karp ’19 and run by students from the Nolan School of Hotel Administration. She offered to redo their website; soon after, she joined in a part-time marketing capacity. “By the time I graduated, I was COO, overseeing operations for the company,” she says. “I spent my junior and senior years working with them out of the Pillsbury Institute, which was amazing.”

In addition to providing needed workspace, Pillsbury offered access to its Entrepreneurs in Residence and industry contacts (many of whom she would conveniently “bump into” at the Statler lobby bar after class).

“I met with a lot of these folks and explained how we were selling luxury travel to high-net-worth individuals. A good number of them became clients. They were like, ‘This is amazing — these innovative kids are doing luxury travel. I need a travel advisor; I’ll use them.’ We got a lot of clients that way.”

Working with MilesAhead, Van Hollebeke experienced the thrill that comes with entrepreneurship. “You’re moving an entire business, making real changes, owning decisions,” she says. “It gave me the understanding that I kind of loved it. That was what gave me the idea to start my own company.”

The push came from Teaching Professor Andrew Quagliata at the SC Johnson College of Business. Prior to taking Communication for Entrepreneurs, Van Hollebeke had applied MilesAhead to class projects so she could work concurrently on the business. He wouldn’t accept that; for his class, she had to propose a new business.

“That forced me to think about problems and pain points in the industry, which got me thinking I could start a business,” she says. “And I came up with the idea that became TripKit, my first company.”

After graduating, Van Hollebeke worked at MilesAhead by day and on TripKit, a digital concierge platform for luxury travel advisors, by night. In February 2020, she left MilesAhead to work full time on TripKit. And then the pandemic hit, causing her to rebuild and regrow the company. At the same time, she completed an accelerated one-year MBA program at the University of Notre Dame’s Mendoza College of Business.

While at Notre Dame, Van Hollebeke had the idea for what would become her second company, Lucia, “the second take on my first business,” she says. “Instead of having a bunch of assistants for the travel industry, which is essentially what TripKit was, I decided to build a freelancer marketplace that still had all these assistants doing services work, but they were no longer my employees; they were independent contractors. That made for a much more flexible business.”

She sold TripKit in 2022 and then raised capital and built out the tech infrastructure for Lucia. “Over the next three years, I really grew out that business. We raised over $1.2 million and had over 500 contractors working on the platform. We funneled hundreds of job requests through the platform in a given year,” she says. Lucia was named one of PhocusWire’s Hot 25 Travel Startups for 2025.

That year, Lucia was acquired by Tern, which had been one of its biggest customers. Lucia is now fully integrated into Tern’s ecosystem, and Van Hollebeke is Tern’s head of brand and partnerships.

“It’s an incredible business,” she says. “I have literally never worked harder, never had more of an impact across the industry.”

The Entrepreneur in Residence

Van Hollebeke, who is passionate about mentoring the next generation of travel-tech entrepreneurs, has been an Entrepreneur in Residence since 2023.

As a recent graduate, she offers a perspective closer to the experience of current students than most other EIRs. “In many ways, I feel like I’m still a student myself, trying to figure things out,” she says.

When she meets with students, “I try to be very blunt and honest with them. I poke holes in their ideas to get them thinking. There’s a confidence that comes from responding to feedback and evolving a business that lets people then go forth and pursue it.”

“I try to get students to come to realizations on their own,” she says, “because a lot of entrepreneurship is learning as you do things. There’s no fast track.”

Van Hollebeke has spoken to classes, participated in coffee chats and judged the Hospitality Pitch Deck Competition.

“Being an Entrepreneur in Residence has given me so much,” she says. “It forces me to reflect on the work I’m doing, but it’s also really fulfilling.

“I got so much out of Pillsbury. If I didn’t have that genuinely safe and thought-provoking space when I was a student, I don’t think I would have become an entrepreneur. So, to be able to help others do that is just so meaningful.”