AT 21 YEARS old, Jesse Head already runs not one but two coffee trailers. She launched the first one, The Wandering Bee, at the age of 19 when she was barely a year out of high school. Then, sensing the business of mobile lattes and dirty sodas was growing faster than she expected, she invested in a second custom-built trailer, The Flying Pig. “I wanted to do something where I could be my own boss. I didn’t see any reason to wait,” she says. Her accomplishments seem less surprising once you learn where she comes from. Entrepreneurship is practically the family trade.
Before she started whipping up foam-topped energy drinks, flavored lemonades, bubble teas, and spruced-up espresso drinks like her personal favorite Honey Bun Latte, Head was logging hours at her family’s novelty bent pencil company, Bentcil. It was founded nearly five decades ago by her grandfather, Tom Killion, who invented a bent pencil product while teaching a plastics class at Ben Davis High School. Both her father, a farmer, and mother are business owners. And her sister runs Oinking Acres Farm Rescue & Sanctuary next door to Head’s family farm in Brownsburg. At first, that was where she set up shop, catering to customers attending events and flower u-pick sessions. Today, she travels throughout Hendricks County for pop-ups and private events. “People will come up to the trailer and say, ‘Oh this looks so fun. I would love to do this.’ I tell them to go for it!” Head says. “I mean, it’s a lot of work. But if you have a good business model and a smart plan that you can stick to, then you should be successful.”
