My guest for Episode #279 of the My Favorite Mistake podcast is Cynthia Kay, author of Small Business Big Success: Proven Strategies to Beat the Odds and Grow a Great Business.

Episode page with video, transcript, and more

As a business owner for over 35 years, Cynthia Kay has attracted well-known and respected customers from the global Fortune 100 to smaller forward-thinking businesses. Along the way, she has developed practical, actionable strategies for businesses from starting up to stepping out. 

As a former board chair of the National Small Business Association, she had advocated for small businesses and spoken to diverse audiences across the country. She has also mentored business owners as a member of the American Academy of Entrepreneurs. 

In this episode, Cynthia shares her journey as a business owner and the lessons she's learned along the way. Cynthia discusses her favorite mistake—starting her business with a partner who wasn’t a good fit. Despite planning out the financial and operational aspects, she overlooked the importance of aligning on working styles, values, and approaches to growth. Over time, their differing perspectives, particularly around scaling the business and relinquishing control, created tension. This led to the eventual dissolution of the partnership.

Through this experience, Cynthia developed the idea of a "business prenup," emphasizing the importance of thorough communication and alignment before entering into partnerships. She also offers advice on leadership, hiring, and building a resilient organization.

• What would you say is your favorite mistake?