Side Hustle to Small Business

Heather Gibbons is a wife, mother, twin sister, and musician. She’s also the co-founder of INMO Creative, a full-service creative agency based in Atlanta. As Heather and her business partner, Simon, establish their agency in its first year of business, they focus on the “simple things.” Together, they’re committed to building a solid foundation of systems and processes that aligns with their beliefs, values, and mission.

With a creative writing and data analysis background, Lauren Ramsey brings her skills to the table as the founder and Chief Engagement Officer at Betsy Bash. Founded in 2010, Lauren and her team help local businesses get more leads and make more sales using social media. She’s taken her business from her hometown of Houston to her new home in Chicago, but her passion has stayed rooted: helping small businesses make a bigger impact.

Jennifer Bourn has been self-employed for 17 years. She started her creative services agency, Bourn Creative, in 2005 and added on a side hustle, teaching courses and workshops in 2017. When Jennifer’s best friend offered her a full-time job, Jennifer was intrigued but also had conditions. She would accept the job, but her side hustle had to stay up and running. A compromise was reached, and now Jennifer has the best of both worlds.

Michael Cox has been in the corporate sales recruiting world for 20 years. But when his recruiting side hustle yielded more profit and control, Michael realized he could open his own business. He founded Zag Worx in late 2019. Starting a business in the wake of a global pandemic with few companies hiring, Cox was forced to innovate. He transitioned from full-service recruiting to offering highly-specific services tailored to his client's needs.

Chris Casseday always loved collecting shoes. Not just shoes in general, but really, really nice sneakers. Twenty years ago, he began selling collectible sneakers on eBay. As his experience and sales volume grew, he founded 513 Kicks. Since 2017, Chris has managed 513 Kicks solo while working full-time as a Director of Operations. For Chris, selling sneakers isn’t just a hobby. It’s a fun — and profitable — side hustle. 

Joe Casabona started Podcast Liftoff in 2017. He helps his clients transform their podcasts from a hobby to a revenue-generating machine. In 2022, Joe realized that he was providing too many services to his customers. Instead of a jack of all trades, he wanted to be known as the guy who eats, sleeps and breathes podcasts. He adapted his product offerings and is now learning that, when it comes to your business, sometimes less is more.

During his 26 years in the web design industry, Wayne Pelletier designed thousands of websites. He also learned the patterns that cause frustration and communication breakdowns between web designers and their clients. So when Wayne started his company, Resonant Pixel, in 2020, he employed a different business model that broke the mold of standard website services. Instead of a lump-sum investment, his team uses a subscription-based model.

Morgan Hancock is full of ideas and energy, and her work life reflects those qualities. She’s a commercial real estate agent, US Army veteran, mother of two, and passionate advocate of the arts. Most recently, Morgan founded Bourbon with Heart, a nonprofit with a mission to leverage the influence and popularity of bourbon to raise funds for local charities while also providing a first-class arts experience for Kentuckians.

In 2009, Melissa Zeman said, “Someday, I’m going to open a wine shop that focuses on community.” She got to work, and ten years later, Melissa opened Bottles Up!, a wine shop and experience in the Lakeview East neighborhood in Chicago. Through in-store events and collaboration with other local vendors, Melissa’s business model has centered around “retail-tainment” — creating, educating, having fun, and, most importantly, connecting.

Growing up in Jamaica, Donald Kelly saw his family members and neighbors selling goods and services on every corner. Naturally, Donald believed that to be an entrepreneur, you had to first and foremost be a salesperson. Since then, he's gained life and business experience while moving to the US, starting a podcast, and writing a book. But Donald still draws on his childhood experience selling mangoes in Jamaica as a metaphor for successful sales.