Side Hustle to Small Business

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.

From ”unemployable” to 27 years in business

When Steve Zehngut earned a degree in film and began working in the entertainment industry, he realized it wasn't for him. He transitioned to a graphic design agency, which wasn't a fit either. Was Steve unemployable? No. He was just a misplaced entrepreneur. In 1995, Steve left the corporate world for good. He founded Zeek, which has grown to become Southern California's leading web, interactive, and mobile development agency.

Taking advantage of every learning opportunity

Maddy Osman draws on past experiences as she manages her SEO content agency, The Blogsmith. Growing up with an entrepreneur dad, she understands that owning a business requires intentional boundaries. Her previous job in the Groupon sales department taught her that rejection isn’t personal. Freelance writing for a Chicago lifestyle blog sharpened her SEO skills. Maddy uses these lessons learned to improve — both herself and her business.

Coordinating win-win solutions for his project teams

Todd Ward combines his design background and general contracting experience as an independent owner’s representative and project manager. He assists his clients with their building projects — anything from development, to new construction, to remodeling. Todd attracts repeat customers because he knows the only way you can reach a win-win solution is if you know what winning means to the other side.

Counting on family for inspiration, support, and purpose

Family plays a critical role in Nathan Hamilton’s life. His loved ones have been with him at every step of his business journey as he’s grown In A Lifetime Photography, based in Houston, Texan. Nathan’s uncle taught him film photography in high school. The birth of his daughter prompted him to start a side hustle to gain a flexible schedule. Today, his wife and two kids encourage him to dream big, have fun, and get rest.

Pitch Perfect: How Rob Friedman became the Pitching Ninja

Though Rob Friedman trained and practiced as a lawyer, his passion was coaching and playing baseball. In 2014, he dove into the world of content creation. His niche? Not just baseball, but pitching specifically. Pitching Ninja was born. Since starting Pitching Ninja, Friedman has amassed over 400,000 Twitter followers, 100,000 Instagram followers, and appears on TV networks like Fox Sports and Peacock as a Pitching Analyst.

Taking the Stage: Courage, Confidence, and Charisma

ShaVonne Davis is a former classroom teacher who channels her love for theatre arts into her small business, Acting with Mrs. Davis. Acting With Mrs. Davis is a Theatre Arts Education Company that provides after-school programs, classes, workshops, and education consulting. ShaVonne teaches her students culture, self-confidence, and creative expression and understands that when you do good work, success will follow.