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:  [email protected]

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: [email protected]

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.

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 website.  

You can contact David at:  Email: [email protected]
Business Phone: (314) 721-2525
Mobile Phone: (314) 561-5078

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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/  

Thank you for watching this video!  Please subscribe, comment and share with those that need to hear it.

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Learn more about what we do at Innovative Business Advisors: 

→ Business Brokerage Services (Buy or Sell a Business): https://innovativeba.com/business-brokerage-services/

→ Valuation Services (3 Types of Business Valuations): https://innovativeba.com/business-valuation-services/

→ Coaching Services (Private, Teams, Retreats & More): https://innovativeba.com/business-advisory-services-coaching/

→ Books (You Don’t Know What You Don’t Know™ Book Series): https://youdontknowwhatyoudontknow.com/ 
 
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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.

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:  [email protected]

Website:  https://www.cutterco.com

LinkedIn: www.linkedin.com/in/brucedward

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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/ 

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/ 

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.

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 Dale Furtwengler, Founder of Cutting Edge and Author of Pricing for Profit and Generate Greater Profits With Fewer Sales.

Dale’s Bio

Dale Furtwengler is the founder of Cutting Edge, a company dedicated to helping you attract the customers you desire and the profits you deserve. Dale is the author of Pricing For Profit and Generate Greater Profits With Fewer Sales. His work has been recommended by the University of Glasgow, the University of New South Wales and the Australian Institute of Management.

Business Overview

Cutting Edge provides clients with 5 elements of a premium price strategy:

1. A clear brand promise…the result the customer will get.

2. A psychographic profile of their ideal customer…a profile based on values, behaviors and characteristics.

3. Marketing messages that attract the ideal customer and repel those who aren’t.

4. Sales scripts that convert benefits into dollars and cents value.

5. Bundling/pricing…three budget options with tips for helping clients' customers get the best result and the client higher average sales tickets.

Plus, Cutting Edge helps clients gain, and sustain, a decades-long competitive advantage with its unique approach to sales.

You can contact Dale at:

Phone:  314-707-3771

Email:  [email protected]

Website:  https://cuttingedge-business.com/

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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/

Thank you for watching this video!  Please subscribe, comment and share with those that need to hear it. 

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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.

Learn more about what we do at Innovative Business Advisors:

→ Business Brokerage Services (Buy or Sell a Business): https://innovativeba.com/business-brokerage-services/

→ Valuation Services (3 Types of Business Valuations): https://innovativeba.com/business-valuation-services/

→ Coaching Services (Private, Teams, Retreats & More): https://innovativeba.com/business-advisory-services-coaching/

→ Books (You Don’t Know What You Don’t Know™ Book Series): https://youdontknowwhatyoudontknow.com/

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.

In this episode, we sit down with the inspiring founders of the NinniCo pacifier.  NinniCo founders, Joy Williams & Jane Molina, started the women-owned company in their mom’s living room with a homemade Shopify site and turned it into a viral sensation that sold out in minutes—and today, their pacifier is trusted by families and feeding specialists around the world.

What you’ll hear in this episode:

✨ The viral TikTok moment that launched NinniCo when they had only 35 pacifiers on hand

✨ How friends, family, porch pickups, and DIY marketing fueled their early growth

✨ Why lactation consultants, pediatric dentists, and feeding therapists embraced the Ninni pacifier

✨ The challenges of scaling manufacturing and outgrowing their first mold

✨ Their disappointing Amazon experience—and why they returned to direct-to-consumer sales

✨ How they built a community of moms who value authenticity over polished marketing

✨ Their long-term vision: to become one of the top five baby brands in the world

✨ Lessons in leadership, delegation, and building a mission-driven company that supports moms and kids globally

💡 This is more than a product story—it’s a story about faith, resilience, and entrepreneurship. Whether you’re a mompreneur, startup founder, or simply love hearing how big ideas grow, you’ll find inspiration here.

👉 Learn more at www.ninnico.com

You can contact Joy & Jane at:

• Ninni Co
• [email protected]
• 314-833-9285
• NinniCo.com

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Connect with Innovative Business Advisors on Social Media:

→ Facebook:   / innovativeba 
→ Twitter:   / abnllc 
→ LinkedIn:   / innovative-business-advisors 

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.

This special episode is with 7-year-old entrepreneur, Auggie Keenum.

Augustus (Auggie) Lee Keenum is a 7-year-old son of Keaton and Kali Keenum.  He has always had a desire to create and been interested in “fine” works such as beading and sewing.  After being exposed to Trout fishing and all of the amazing insects (also a passion of Auggie) he was introduced to Fly Tying by his grandfather (PopPop).  His parents saw this joy and invested in tools and materials for fly tying which quickly turned into hours every weekend fly tying, a welcome replacement from roughhousing and TV watching. 

In the Summer of 2022 Auggie was approached with the opportunity for “Makers
Market”.  This was a great event put on by the Lake St. Louis Farmer’s Market every year, for homeschooling kids to get a taste of what it is like for a start-up business.  Auggie worked for weeks in preparation and realized this was a fun way to earn income. He showcased his organic sales skills on market day and surpassed his goal that was set during the business planning.

Between baseball, basketball, and motor bikes, Auggie is still found regularly at the kitchen table making “bugs” that he hopes to catch the next “BIG FISH” on or sell for someone else to get that enjoyment.  This was Auggie’s realized takeaway during this business launch, “I have fun making the flies and bugs, and the people who buy them have fun fishing. I hope they catch a lot of fish with my flies, or maybe one big fish. Or maybe they don’t catch anything but have a great memory. That’s all that matters.”

You can shop Auggie's flies on his Facebook page at:
https://www.facebook.com/profile.php?id=100088538287383 

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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/

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/

→ Valuation Services (3 Types of Business Valuations): https://innovativeba.com/business-valuation-services/

→ Coaching Services (Private, Teams, Retreats & More): https://innovativeba.com/business-advisory-services-coaching/

→ Books (You Don’t Know What You Don’t Know™ Book Series): https://youdontknowwhatyoudontknow.com/ 

Connect with Innovative Business Advisors on Social Media:

→ Facebook: https://www.facebook.com/innovativeba

→ Twitter: https://twitter.com/ABNLLC

→ LinkedIn: https://www.linkedin.com/company/innovative-business-advisors/

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 profit

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.

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 Julie Hamilton, Owner of Coaching PI.

Julie Hamilton has over 20 years of Human Resource Management experience and has been a Certified Fibromyalgia Coach for over 7 years.  She was diagnosed with fibromyalgia in 2009.

As a Human Resources Director, she knew the resources to use such as Family Medical Leave Act and workplace accommodations to help her with the tasks she was struggling with.  She didn’t need to worry about her job when she needed to take time off for flare days or medical appointments. She went from missing two to four days per month to missing two days or less a year.

Then after relocating to Ohio, her chronic illness made it impossible for her to work.  That is when she studied to become a Certified Fibromyalgia Coach and learned to manage her fibromyalgia.  She has gone from being in bed 90% of her life to walking three miles a day and even participated in her first 10k.  She now helps professionals who have fibromyalgia maintain their career and regain their active social life.

Her goal is to help companies create an inclusive environment for the chronically ill and assist them in implementing policies to benefit both the employee and the company.  She understands what it takes to make it work and can educate the company and the employee on how this collaboration can work.

Her company is Coaching PI.  For the past 7 years she's been helping clients 1:1 but through that coaching she learned that companies do not know how to work with their chronically ill employees.  The following is basically what she likes to talk about when she's discussing this with companies.

You know how important it is to have quality employees and how crucial retention is to your organization.  But are you wondering how to make your chronically ill employee more productive?

This scenario may have happened before your eyes – that star employee used to be very productive but recently was diagnosed with a medical issue.  Maybe they have turned into that mediocre employee – or worse, a bad employee.  If you want to learn how you can turn that employee back into a more productive employee, this discussion is for you.

You can contact Julie at:
Email - [email protected]
Website - coachingpi.com
Phone - 402-520-0255
Link to book - https://amzn.to/46nSQfb

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 guest Charis Santillie, Life Balance & Transition Coach, and host of the Charis Your Life® podcast.

Charis Santillie is a Life Balance & Transition Coach and host of the Charis Your Life® podcast.  She is also a speaker, Certified Fearless Living® Coach, Certified Fearless Trainer, and Positive Intelligence® Trainer and has been an entrepreneur for over twenty years.  She now helps entrepreneurs go from Busy to Balanced™...and Beyond.

Specifically, she supports entrepreneurs at two different stages of their lives:

1.  In the busy mid-life stage, when they are ready to ditch life's guilt and anxiety and finally find more peace of mind (In other words, they're realizing that their external accomplishments haven't brought lasting
inner satisfaction.)

2.  In the exit transition stage, when they need to design their life after business so that they don't lose their way after exit day. (This involves guiding them through the emotional journey that is often overlooked in exit planning.)

You can contact Charis at:

Email:  [email protected]
Phone:  844-444-1975
Website:  https://charisyourlife.com
Charis Your Life® Podcast:  https://podfollow.com/charisyourlife

Free Video Training 'How to Live Life on Your Own Terms & Timeline (Ditch Life's Guilt & Anxiety — Finally Find More Peace of Mind)' https://charisyourlife.com/video

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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/

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/
→ Valuation Services (3 Types of Business Valuations): https://innovativeba.com/business-valuation-services/
→ Coaching Services (Private, Teams, Retreats & More): https://innovativeba.com/business-advisory-services-coaching/
→ Books (You Don’t Know What You Don’t Know™ Book Series): https://youdontknowwhatyoudontknow.com/

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Connect with Innovative Business Advisors on Social Media:

→ Facebook: https://www.facebook.com/innovativeba
→ Twitter: https://twitter.com/ABNLLC
→ LinkedIn: https://www.linkedin.com/company/innovative-business-advisors/

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.