YOU DON'T KNOW WHAT YOU DON'T KNOW

Mastering the Basics: Building a Profitable & Sustainable Business with John Matthews of Gray Cat Enterprises

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. =================================================================== 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/ [http://www.graycatenterprises.com/] LinkedIn profile: https://www.linkedin.com/in/john-matthews-00253a/ [https://www.linkedin.com/in/john-matthews-00253a/] ======================================================================= 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 [https://zcform.com/l6B8j].

AI is Awesome - My interaction with Notebook LM

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 [https://zcform.com/l6B8j].

From Strategy to Transition: A Business Journey - The Transition Strategists

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 [elizabeth@transitionstrategists.com] Phone: 720.989-8831 Website: https://transitionstrategists.com/ [https://transitionstrategists.com/] =============================================================== 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 [andrea@transitionstrategists.com] Phone: (303) 790-0754 Websites:  https://transitionstrategists.com/ [https://transitionstrategists.com/], https://yournextgenfriend.com/ [https://yournextgenfriend.com/] Free Business Transition Resource: https://letstalktransition.com/iba [https://letstalktransition.com/iba] =============================================================== 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 [https://zcform.com/l6B8j].

Interview with David Weiss, Jenkins & Kling, P.C. – Everything You Need to Know About the Corporate Transparency Act

This episode is with special guest David Weiss, Corporate Attorney/Partner with Jenkins & Kling, P.C.  David has represented small and medium-sized businesses, nonprofit corporations, and individuals for over 30 years in such areas as enterprise formation; governance and disputes; business succession planning; contract negotiation and enforcement; mergers and acquisitions; commercial transactions; real estate; homeowner and condominium association representation; and estate planning. David routinely represents clients in the boardroom and, after first-chairing over 60 trials, provides strategic guidance in litigation involving business disputes, shareholder and corporate governance matters, and homeowner and condominium disputes.  Client industries include manufacturers and distributors, marketing and advertising agencies, restaurants and other B2C enterprises, architects, engineers and medical professionals, homeowner associations, real estate ventures, national and local professional organizations, and non-profit organizations.  A firm believer in giving back to the community, Weiss has served in a variety of capacities, including currently serving on the Board of Trustees of his alma mater, Webster University, Christian Hospital Foundation, and the St. Louis County Parks Foundation. Weiss also has shared his legal knowledge through seminars, broadcasts and through his ever-popular eLawLines.com [https://linkprotect.cudasvc.com/url?a=https%3a%2f%2feLawLines.com&c=E,1,aWOGPKnEp5KMzhbnVP-1Xnau_bl0jkjex5ooLOXiZa4bPpoLOHaSjgQR3X9o8v5dlm0Q62vOhtu55C1SN9KkXlKpnNGhSwt36U7YokwLNm1cdXCfCw,,&typo=1&ancr_add=1] website.   You can contact David at:  Email: dweiss@jenkinskling.com [dweiss@jenkinskling.com] Business Phone: (314) 721-2525 Mobile Phone: (314) 561-5078 ===============================================================  If you would like to be a guest on the You Don’t Know What You Don’t Know™ Podcast, or know someone who would make a great guest, let us know at: https://innovativeba.com/contact/ [https://innovativeba.com/contact/]   Thank you for watching this video!  Please subscribe, comment and share with those that need to hear it. ==========================================================  Learn more about what we do at Innovative Business Advisors:  → Business Brokerage Services (Buy or Sell a Business): https://innovativeba.com/business-brokerage-services/ [https://innovativeba.com/business-brokerage-services/] → Valuation Services (3 Types of Business Valuations): https://innovativeba.com/business-valuation-services/ [https://innovativeba.com/business-valuation-services/] → Coaching Services (Private, Teams, Retreats & More): https://innovativeba.com/business-advisory-services-coaching/ [https://innovativeba.com/business-advisory-services-coaching/] → Books (You Don’t Know What You Don’t Know™ Book Series): https://youdontknowwhatyoudontknow.com/ [https://youdontknowwhatyoudontknow.com/]    ===========================================================   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 [https://zcform.com/l6B8j].

Bruce Ward, Financial Advisor – Cutter & Co., Unique Financial Planning with a Focus on Helping Business Owners

We engage in conversations with successful business owners to learn the little things that made the journey of building their companies special. Then we discuss how they plan to hand off their business to the next generation of leadership.  This episode is with special guest Bruce Ward, CFP, CHFC, CLU, RICP, Financial Advisor with Cutter & Company.  As a Coast Guard officer and trained navigator, Bruce learned three guiding principles:  Where are we? Where are we going? How do we get there?  Bruce continues to apply these principles as a financial advisor. First, he begins with a comprehensive review so he can clearly understand your current situation. Next, you’ll discuss where you envision your situation next year, in five years, and beyond to determine realistic financial objectives. Finally, you’ll work together to create a customized strategic plan that will be implemented and will be “course corrected” along the way to help you reach your financial objectives.  Creating a financial strategy that is unique to your goals is an exciting process that, when complete, provides comfort and satisfaction knowing you’re working toward a future for you, your family, and your business. Bruce is there every step of this fulfilling, lifelong journey providing information, tools, support, clarification, and advice to help keep you on course and in command of your financial future.  Bruce’s clients include:  ·         Business owners who want to maximize the value of their business and then successfully exit that business. ·         People who need a comprehensive retirement-income strategy to help ensure retirement will work for them. ·         Families wanting a tax-efficient investment portfolio to avoid paying taxes, under current tax law, on the growth of their money.  Bruce’s clients value his flexibility, personalized approach, and the choices he provides to help them feel in charge of their money and less stressed about retirement.  You can contact Bruce at:  Phone:  636-779-1634 Mobile:  314-960-3221 Email:  BruceWard@CutterCo.com [BruceWard@CutterCo.com] Website:  https://www.cutterco.com [https://www.cutterco.com] LinkedIn: www.linkedin.com/in/brucedward [http://www.linkedin.com/in/brucedward] ===============================================================  If you would like to be a guest on the You Don’t Know What You Don’t Know™ Podcast, or know someone who would make a great guest, let us know at: https://innovativeba.com/contact/ [https://innovativeba.com/contact/]  Thank you for watching this video!  Please subscribe, comment and share with those that need to hear it.   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. For support, business inquiries, or if you have a question or comment about buying or selling a business, getting a business valuation, or growing your business with classes or coaching please visit: https://innovativeba.com/contact/ [https://innovativeba.com/contact/]  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 [https://zcform.com/l6B8j].