Side Hustle to Small Business

Keeping her side hustle while starting a new full-time job

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.

How a pandemic-forced pivot paid off long term

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.

Selling sneakers as a side hustle? Possible and profitable

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. 

How simplified product offerings helped business Liftoff

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.

Opening his own business and breaking industry standards

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.

Mixing arts and philanthropy with Kentucky bourbon

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.

Cheers! How Melissa Zeman creates community with wine

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.

Sell it like a mango? Donald Kelly can teach you how

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.

From designing video games to getting funded by Mark Cuban

Rob Kischuk started his career designing video games for Facebook in the days of FarmVille. When Rob was laid off, along with 90% of his team, he asked himself, “What now?” Since then, Rob has started four software-based businesses, one of which acquired funding from Mark Cuban at a serendipitous Super Bowl Shark Tank watch party. Throughout his 10 years in the startup world, Rob has learned to take risks: you never get what you don’t ask for.

Accepting feedback, iterating, and getting better

Born in France to entrepreneur parents, Nicolas Billaiche learned the value of having a community of fellow business owners. But when he left his corporate career in sales and founded eStreamly, he was bombarded with opinions. Nicolas didn't take this constructive criticism personally but used it to inspire action. With the help of his business partner, he's learned to accept feedback and adapt his game plan but ultimately trust his gut.