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.

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.

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.

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.

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.

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.

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?

Have you ever wondered what would happen if you just quit your job with no plan for what you would do next? In this episode Sanjay talks with Jim Garrison who did just that. Thirty-two years later, Jim has a successful business and reflects on the twists, turns, and lessons he learned along the way. He also has great advice if you are thinking of making the same jump: “Don’t be afraid and start today.”

After getting his first computer at age 9, Larry Dukhovny began his life as a self-proclaimed computer geek. This passion for technology prompted his career path in IT consulting. After freelancing for six years, Larry founded MyBizGeek in 2013. Passionate about believing in yourself and the value of your service, Larry now advocates for building inner confidence to accelerate your business and attract new clients.

When it comes to personality types, there is Meyers Briggs and StrengthsFinder, among others. But Grant Nichols uses a more general term when describing himself: entrepreneurial. He constantly brainstorms new business ideas, researches their market potential, and vets the project’s viability with his friends and family. Grant founded his current business, BluWave Technologies, to help manufacturing companies increase operational efficiency.