Most of us grew up believing in linear career trajectories: major in a subject in college, get a job related to it after graduating, move up the ranks until you’re a top-level employee living the good life. As the entrepreneurial spirit of the millennial generation burgeons, however, that old-school way of thinking has gone out the window. Serving as this new wave’s poster child: Natasha Case, who veered off her original path after architecture school and found her calling as co-founder and CEO of the ice cream company Coolhaus.
Her resume reads like something out of a kid’s dream: starting out as a Disney Imagineer (that’s a team member of the design and development force behind Disney’s parks and resorts—a prestigious and famously hard-to-get gig) and leading to a full-time role dreaming up gourmet ice cream confections to distribute via a food truck. What started out as an experiment in her affinity for combining food and architecture has since landed Coolhaus in 4,000 retailers, 11 trucks in major U.S. cities such as New York and Dallas, and two brick-and-mortar shops in California, not to mention a namesake book.
We had the chance to talk with Case about the value in trusting your passions, going after a job you really want and her top lessons learned from running her own business.
How did you first learn how to make ice cream sandwiches?
“Food and cooking has always been a passionate hobby. I am self-taught and always loved to explore new techniques, cuisines and dishes. I’d host dinner parties in college and actually started making ice cream sammies during my time at Disney Imagineering. Ice cream is well-suited for self-taught cooks because it’s a great canvas where once you understand the fundamentals, you are pretty liberated to explore and experiment with new flavors. It was just for fun at first, but then we noticed there wasn’t a lot of gourmet, hand-crafted ice cream companies and the flavors we were developing were more unique than the going standard at the time. We thought with a food truck, we could capitalize on this untapped niche, and do it cheaply. There really were no gourmet dessert trucks in L.A. at the time, so we were able to be first to market.”
What experiences prepared you most for being an entrepreneur?
“My background in architecture helped prepare me. Throughout my education and time at Disney Imagineering, I learned a lot about teamwork, merchandising, telling a story through visual identity and working with service-based clients.”
You’ve said you were very diligent about getting Disney to consider you for a job. What tips do you have for really going after a position you want?
“Don’t be afraid to show your dream employer how much you want the job. When I was applying for Disney Imagineering, I didn’t hear back until I followed up what must have been 15 times. Be persistent—it’s all about the follow up! Also, during the interview we talked about some subjects that weren’t related to work, like travel and foreign languages. I think my future bosses got a sense of what kind of personality and energy I would bring to the office, outside of just my resume points.”
Since you started as friends with co-founder Freya Estreller before you were business partners, how did you maintain that balance?
“To be honest, it all kind of happened at one. Freya and I were introduced and then started dating—I brought a prototype architectural ice cream sandwich to our first date! We didn’t overthink it or over discuss it, we just kind of dove head first, seeing that we shared the big vision for Coolhaus and had a complementary skill set to cover lots of terrain. We were able to grow the company quite fast because we were always working on it, hashing out ideas, coming up with flavors, etc. However, drawing the line between business and pleasure isn’t easy. You have to set rules and follow them. It’s challenging, but you have to make sure business is not always the default conversation. It’s important to step aside and have dinner without mentioning work. But when it’s time for dessert, anything is fair game. And in the end, Freya and I are happily married—just had our three year anniversary—so a business and pleasure balance can be achieved!”
When did you know it was time to leave your day job?
“For me, it was less of a choice than a necessity. Coolhaus was taking off, and there was a hiring freeze and series of layoffs at Disney as a result of the start of the recession. I saw that if I devoted more time to Coolhaus, I could capitalize on all the buzz and demand and make it a viable career move for myself. I remember Freya saying, ‘Are you sure Coolhaus can afford to pay you?’ And I said, ‘No, I’m not!’ There are no guarantees, but sometimes you just go for it. Freya worked in real estate development for another few years before joining Coolhaus full-time. It was helpful to have her stable salary—and also probably a little bit of separation—but by 2011 we really needed her day-to-day involvement to manage finance and operations.”
What is the most valuable lesson learned from your first year of business?
“Be proactive, not reactive. A lot of things went wrong in our first year because we didn’t know what we were doing. For example, the truck would break down unexpectedly and we would have to get it fixed. Now we have a maintenance routine and we experience a lot less problems!”
What is the most difficult part about being your own boss? How do you handle it?
“It can be a thankless job. A huge part of being a CEO is encouraging the right actions from your team, and constructively guiding the less-than-desirable course toward a better direction. You are always working, pushing, striving to be better at what you do and guiding them. But since you are at the top, it’s less likely that someone will sing your praises when you’ve accomplished something good—so you just have to know you’ve done well and met your own goals.”
What has surprised you most in your career?
“How much just being yourself and trusting your instincts counts for. I think there is a conception early in your professional career about conforming and playing by the rules—but people are really drawn to unique visions and authenticity. They feel connected and celebrate that kind of confidence. It’s really exciting and empowering when you realize that. It clarifies one’s sense of purpose, and you realize even more so how much opportunity is out there!”
If you could go back, what would you tell yourself after you just graduated?
“Draw your vision first—like literally, put it on paper—then work to create it.”