
A weekly podcast from Hiscox, the small business insurance experts. We’re changing the conversation around the side hustle and featuring founders at various stages of their small business journey. These entrepreneurs are pushing the envelope while keeping their values and have learned a few lessons along the way. Listen each week for conversation, context, and camaraderie. Hosted by Sanjay Parekh, produced by Edgewise.Media.
Episodes

Feb 15, 2023
Feb 15, 2023
35 min
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.

Feb 8, 2023
Feb 8, 2023
32 min
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.

Feb 1, 2023
Feb 1, 2023
31 min
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.

Jan 25, 2023
Jan 25, 2023
33 min
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.

Jan 18, 2023
Jan 18, 2023
32 min
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.

Jan 11, 2023
Jan 11, 2023
29 min
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.

Jan 4, 2023
Jan 4, 2023
33 min
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.

Dec 14, 2022
Dec 14, 2022
32 min
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.

Dec 7, 2022
Dec 7, 2022
28 min
Angel Hendrix knew that her season of contributing to her job was over and she wanted to do more, but what was next? She wanted to get into real estate without having to be a Realtor; so she took a notary class, and her business took off from there. Now Angel has several lines of business, is an example of entrepreneurship to her daughter, and is looking to hire some help to take her business to the next level.

Nov 30, 2022
Nov 30, 2022
34 min
Just because your business is thriving doesn’t mean it’s perfect for you. That’s one thing Dr. Karen Jacobson realized as she started to transition from her thriving chiropractic practice to something new. One of the hardest parts of that process was leaving the safety of what is known, for the adventure of what is unknown, and answering the question many entrepreneurs struggle with: When do I take the leap?
