586 – The Power of Play in Business with Cas Holman
The How of Business - How to start, run, grow and exit a small business.
Release Date: 10/27/2025
604 – Why Partnerships Fail
The How of Business - How to start, run, grow and exit a small business.
The three root causes of business partnership failure - loss of trust, respect, and alignment - and how to prevent them. Show Notes Page: Business partnerships can accelerate success or destroy a business faster than almost anything else. In this episode, Henry Lopez breaks down the three primary reasons partnerships fail: loss of trust, loss of respect, and loss of alignment. Drawing from his own experiences and years of coaching small business owners, he explains why most partnerships don’t fail because of the business itself but because of the breakdown in the relationship between...
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R306 – 5 Steps to Naming with Brad Flowers
The How of Business - How to start, run, grow and exit a small business.
A framework for creating a business or product name using a proven five-step process that removes guesswork and drives better branding decisions, with Brad Flowers. Show Notes Page: Naming your business (or product or service) doesn’t have to be a frustrating or purely creative guessing game. It can be a structured, repeatable process that leads to better outcomes. In this episode, Henry Lopez chats with Brad Flowers, co-founder of Bullhorn and author of The Naming Book, about how small business owners can move from a blank page to a strong, effective business or product name. Brad...
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603 – 5 Tips for Better Emails
The How of Business - How to start, run, grow and exit a small business.
Practical email writing techniques that help small business owners communicate more clearly, get faster responses, and reduce costly misunderstandings. Show Notes Page: Email is still the primary communication tool in most small businesses, yet it’s one of the most overlooked skills. In this episode, Henry shares five simple but powerful tips to help you write better emails that get faster responses, reduce misunderstandings, and improve your professional credibility. You’ll learn how to: Communicate your message clearly and quickly Structure emails so they are easy to scan ...
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602 – Why Your Business is Stuck
The How of Business - How to start, run, grow and exit a small business.
How profitability and scalability constraints in your business model keep you stuck and how to diagnose and remove them to finally grow. Show Notes Page: If your business feels stuck - you are working hard but not breaking through - you may be dealing with hidden constraints in your business model. In this episode, Henry Lopez explains why most small businesses don’t fail outright but instead get trapped in a perpetual startup stage. The root cause is often not effort or resources, but structural limitations in profitability or scalability or both. Henry breaks down the two pillars of a...
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601 – 2026 Franchise Trends with Giuseppe Grammatico
The How of Business - How to start, run, grow and exit a small business.
The latest in key franchise trends, including AI-driven efficiency, stronger franchisor support, and high-demand service industries. Show Notes Page: Franchising continues to evolve rapidly driven by advancements in AI, operational efficiency, and a renewed focus on franchisee success. In this episode, Henry Lopez is joined by franchise expert Giuseppe Grammatico to break down the most important trends shaping today’s franchise landscape and what they mean for aspiring business owners. A major shift highlighted in this conversation is the increased level of support franchisors are...
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600 – Create Your Own Category with Kevin Maney
The How of Business - How to start, run, grow and exit a small business.
How small business owners can escape price-driven competition by redefining their market and creating a new category instead of competing in crowded spaces. Show Notes Page: Many small business owners enter crowded markets and end up competing primarily on price. But according to author and business strategist Kevin Maney, there is another path: create your own category. In this conversation, Henry Lopez speaks with Kevin Maney about the ideas in his latest book “The Category Creation Formula.” The discussion explores how entrepreneurs can redefine the problem they solve and...
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599 – When Should You Outsource Your Bookkeeping?
The How of Business - How to start, run, grow and exit a small business.
When to outsource your bookkeeping, how outsourcing compares to hiring an in-house bookkeeper, and best practices for working effectively with a bookkeeping service. Show Notes Page: Knowing when to outsource your bookkeeping is an important decision for small business owners. As your business grows, bookkeeping becomes more complex, more time-consuming, and more critical to making informed decisions. In this episode, Henry Lopez is joined by bookkeeping expert Jodi Arrant to discuss when it makes sense to outsource your bookkeeping instead of doing it yourself or hiring a bookkeeper...
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598 – Do Your Leaders Know the Score?
The How of Business - How to start, run, grow and exit a small business.
If your leaders don’t know how they’re measured, you can’t expect consistent performance or real ownership. Show Notes Page: Frustrated with inconsistent performance from your managers or senior team members? The issue may not be motivation, it may be measurement. In this episode, Henry Lopez breaks down why leadership performance problems often stem from a lack of role clarity, measurable outcomes, and transparent KPIs. Without clearly defined metrics, even highly motivated leaders drift. Expectations become subjective. Feedback becomes emotional. And performance becomes...
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597 – Why Your Business Will Sell
The How of Business - How to start, run, grow and exit a small business.
Five practical reasons your small business will sell and how to intentionally build long-term exit value. Show Notes Page: Most business owners say they want to sell one day but very few actually build a business someone would want to buy. In this episode, Henry Lopez outlines five practical reasons your business will sell and the disciplines required to build exit readiness long before you’re ready to exit. A sellable business isn’t created at the moment you decide to sell - it’s built over years through intentional design. Henry shares the five core elements that...
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596 – Marketing in the AI Era with Shannon Bailey
The How of Business - How to start, run, grow and exit a small business.
How AI is reshaping small business marketing and why clear positioning and strong messaging matter more than ever. Show Notes Page: Branding and messaging expert Shannon Bailey shares her entrepreneurial journey and explains (starting at 11:10) why clear positioning and concise messaging are essential in the AI-driven marketing era. As AI tools like ChatGPT reshape how customers search for information, small business marketing is entering a new era that rewards clarity over cleverness and positioning over fluff. In this episode, Henry Lopez chats with branding and messaging strategist...
info_outlineToy designer and educator Cas Holman explores how embracing play can unlock creativity, reduce stress, and help small business owners reframe failure as part of growth.
Show Notes Page: https://www.thehowofbusiness.com/586-cas-holman-play-in-business/
Cas Holman, renowned toy designer, educator, and author of Playful: How Play Shifts Our Thinking, Inspires Connection, and Sparks Creativity, shares with host Henry Lopez how play isn’t just for children. It’s a powerful mindset for entrepreneurs.
From her early projects like Rigamajig and playful installations at New York’s High Line to working with teams at Google, Nike, and the LEGO Foundation, Cas has made a career out of turning curiosity and experimentation into design breakthroughs.
Cas and Henry discuss how small business owners can benefit from a more playful approach to work, shifting from rigid outcomes to exploration and possibility. Cas explains her “three essentials for adults to relearn play”: release judgment, embrace possibility, and reframe success.
Together they reveal how these principles foster innovation, collaboration, and agility - qualities essential for thriving in today’s rapidly changing business environment.
“The most important thing any human can be right now is flexible,” Cas shares. “A playful mindset makes us more creative, more agile, and more open to what’s possible.”
You will be inspired to integrate play into small business meetings, problem-solving, and daily business life. Transforming creativity from a childhood memory into a strategic advantage.
Cas Holman is an award-winning toy designer, educator, and author. Founder and Chief Designer of Heroes Will Rise and creator of the acclaimed Rigamajig building kits, her work focuses on the combination of creativity, design, and learning through play. Formerly a professor of Industrial Design at the Rhode Island School of Design, Cas now consults with companies and teams around the world, including Google, Nike, and Disney Imagineering, on the power of play to inspire innovation.
This episode is hosted by Henry Lopez. The How of Business podcast focuses on helping you start, run, grow and exit your small business. The How of Business is a top-rated podcast for small business owners and entrepreneurs. Find the best podcast, small business coaching, resources and trusted service partners for small business owners and entrepreneurs at our website https://TheHowOfBusiness.com