Zachary Green

At 27, Ji Hye Kim quit her job at a medical administration company to become a cheesemonger at Zingerman’s Deli in Ann Arbor, Michigan. Eight years later, she opened her own Korean restaurant, Miss Kim. Ji Hye is now a James Beard Award semifinalist. In 2023, her restaurant brought in $1.8 million in sales. Ji Hye passes much of that revenue on to her staff, paying them $12-$15 per hour and sharing the restaurant’s profits with them.

25-years-old Jake Spotswood is training for the pole vault in the 2024 Olympic trials. At the same time, he’s working as an IT analyst from 9-5 and as personal trainer and volunteer assistant coach for George Mason University’s track and field team. Jake also posts sponsored online content to his 90K followers on Instagram and TikTok. Jake says he’s able to balance all of these plates by sticking to a meticulous schedule every day. Even while training, he expects to earn over $100K in 2024.

In 2014, business partners Matt Scanlan and Diederik Rijsemus drove into Mongolia’s Gobi Desert with $2.5 million tied up in plastic bags. Their goal: purchase 50 tons of cashmere wool from nomadic goat herders for their new clothing company, Naadam. Today, Naadam brings in more than $100 million per year selling relatively affordable cashmere clothing. Its lowest-cost — and most popular — cashmere sweater sells for $98.

35-year-old's design side hustle brings in over $400,000 a year—how she spends her money

Chisom Okwulehie was gifted at drawing from a young age. She decided to turn her artistic instincts toward a more profitable line of work, studying architecture and public planning in college. Today, the 35-year-old mother of two earns about $163,000 a year working as an architectural designer for the Port of Authority for New York and New Jersey and running her own interior design side business for private clients, Juntero.

Brian Smith and Jackie Cuscuna’s ice cream company, Ample Hills Creamery, was a runaway success. A few years after they launched in Brooklyn, New York, they were endorsed by Oprah Winfrey and opened a shop at Walt Disney World. Then, in 2020, the company declared bankruptcy. Six months later, Smith and Cuscuna filed for personal bankruptcy. Now they’re trying again — with new investors and a bevy of lessons learned from failure.

36 year old Cesar Villavicencio — better known by his stage name, “Pixie Aventura” — has been performing as a drag queen since his freshman year of college. He’s been able to build a full-time career performing as Pixie, making $70,000 last year through performances at clubs, weddings and corporate events. Cesar says that while life as a professional drag queen requires a lot of time, out-of-pocket expenses and stamina, it’s also given him more creative agency as an artist and as a performer.

Cesar Villavicencio moved to New York City in 2009 with Broadway dreams. Now he makes $70,000 performing five nights a week as Pixie Aventura.

Annie Park was a Harvard-trained educator when her mom asked for help opening an ice cream store in Bethesda, Maryland: “I never left”

Mike Burton’s been rapping full-time on Fiverr since 2017. He’s made love songs, raps for businesses and original music for YouTube channels.