The Biggest Mistakes Small Business Owners Make: Insights from Cynthia Kay

My Favorite Mistake: Business Lessons from Failures and Success

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.

Questions and Topics:

• What would you say is your favorite mistake?
• Why do you think the partnership didn’t work?
• How did things end up playing out with the partnership?
• How quickly did those differences show up, or did they creep in over time?
• How did you try to address those differences?
• What advice do you have for others considering partnerships?
• When you say the company had grown, how many employees did you have, or what was the scale of growth?
• Can you tell us about the moment when you realized the partnership wasn’t working?
• Can you talk about some of the common mistakes small business owners make?
• What advice would you give about building a resilient organization after setbacks or mistakes?
• How do you handle disagreements in your company, especially with different generations in the workplace?
• What are the key traits that lead to success in your company?
• How do you foster a culture where people feel comfortable admitting mistakes?
• What are your thoughts on creating a learning organization?
• What traits or behaviors do you look for in people who are successful at CK and Company?
• Where can people find more information about you and your book?