In this episode of You Don’t Know What You Don’t Know, we sit down with John Matthews, founder of Gray Cat Enterprises, to explore the “table stakes” every small business owner must have in place before chasing big marketing campaigns or the latest AI tools. Drawing on decades of experience leading billion-dollar divisions and two decades as an independent consultant, John shares practical strategies for dissecting your profit and loss statement, creating a local store marketing plan, managing time effectively, and building strong client relationships that last decades.

We discuss why less than 10% of owners write a real business plan, how preparation unlocks opportunity, and why mastering the fundamentals is your best defense against wasted time and money. John also opens up about his entrepreneurial journey—how he transitioned from corporate executive to trusted advisor across multiple industries, how he built credibility from scratch, and why lifestyle freedom is as important as financial success. Whether you’re running one store or building an empire, this conversation is packed with actionable insights to help you create a sustainable, profitable, and enjoyable business.

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John Matthews Bio:

John Matthews is the Founder and President of Gray Cat Enterprises, Inc. a Raleigh, NC-based management consulting company. Gray Cat specializes in strategic project management and consulting for multi-unit operations; interim executive management; and strategic planning. Mr. Matthews has over 30 years of senior-level executive experience in the retail industry, involving three dynamic multi-unit companies. Mr. Matthews experience includes:

* President of Jimmy John's Gourmet Sandwiches

* Vice President of Marketing, Merchandising, Corporate Communications, Facilities and Real Estate for Clark Retail Enterprises/White Hen Pantry

* National Marketing Director at Little Caesar's Pizza! Pizza!

Gray Cat Company Website: http://www.graycatenterprises.com/

LinkedIn profile: https://www.linkedin.com/in/john-matthews-00253a/

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About Steven Denny: Steven Denny co-founded Innovative Business Advisors in 2018 and serves as a Managing Member of the firm. Steve has been actively engaged in M/A activities in a wide variety of industries for the last 14 years and has developed specific products to assist clients in growing their profitability and enterprise value. His specialty is working with established private companies in the lower middle market with annual revenues from $1 – 50 million.

Thanks for listening to our You Don't Know What You Don't Know podcast! To sign up for podcast updates or to recommend a guest for our podcast, click here.

Excited to share my recent interaction with Notebook LM Podcast about my book, "You Don’t Know What You Don’t Know." This dives into the stories and lessons behind the writing, the power of embracing uncertainty, and why asking the right questions can lead to game-changing breakthroughs.

Thanks for listening to our You Don't Know What You Don't Know podcast! To sign up for podcast updates or to recommend a guest for our podcast, click here.

This episode is with special guests, Elizabeth Ledoux and Andrea Carpenter of The Transition Strategists.

Elizabeth Ledoux is the founder and CEO of The Transition Strategists, an international consulting firm that creates business succession plans for family and private businesses. One hundred percent of the owners who have used her company’s proprietary Transition Roadmap Developer™ to choose and mentor capable successors have positioned their companies for ongoing success and moved forward to live happy and meaningful lives.

With a career spanning over 30 years, Elizabeth has helped hundreds of business owners navigate the complex dynamics that come with business shifts. She works with individuals and families who share her belief that a business transition is only successful if it protects and supports an owner’s most important relationships.

Elizabeth is an entrepreneur who has founded several businesses, a thought leader and sought-after speaker, addressing the topics of business succession planning, challenges and opportunities in private and family business transition, business and individual growth, and the business succession journey. The Harvard Business School has recognized Elizabeth for her work linking the growth and development of the entrepreneur to company success.

She is the host of the podcast Business Transition Roadmap and co-author of three books, including the award-winning It’s A Journey, The MUST-HAVE Roadmap to Successful Succession Planning, (Sky to Sea Publishing, 2021).

You can contact Elizabeth at:

Email: elizabeth@transitionstrategists.com

Phone: 720.989-8831

Website: https://transitionstrategists.com/

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Andrea Carpenter is a UX designer turned business transition guide who's walking the succession journey herself as the incoming President of The Transition Strategists. After watching her dad navigate selling his business, she developed a passion for helping the next generation in successful families write their own stories while honoring their family legacy.

Through her work at the Transition Strategists and as 'Your Next Gen Friend,' Andrea loves creating psychologically safe spaces where rising gens can have authentic conversations about identity, relationships, and purpose beyond the family business. With her unique perspective as both a successor and advisor, she brings a refreshing blend of lived experience and practical frameworks to help others navigate the messy, beautiful path of transition.

You can contact Andrea at:

Email: andrea@transitionstrategists.com

Phone: (303) 790-0754

Websites: https://transitionstrategists.com/, https://yournextgenfriend.com/

Free Business Transition Resource: https://letstalktransition.com/iba

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About Steven Denny: Steven Denny co-founded Innovative Business Advisors in 2018 and serves as a Managing Member of the firm. Steve has been actively engaged in M/A activities in a wide variety of industries for the last 14 years and has developed specific products to assist clients in growing their profitability and enterprise value. His specialty is working with established private companies in the lower middle market with annual revenues from $1 – 50 million.

Thanks for listening to our You Don't Know What You Don't Know podcast! To sign up for podcast updates or to recommend a guest for our podcast, click here.