596 – Marketing in the AI Era with Shannon Bailey

596 – Marketing in the AI Era with Shannon Bailey

Author: Henry Lopez February 16, 2026 Duration: 37:10

How AI is reshaping small business marketing and why clear positioning and strong messaging matter more than ever.

Show Notes Page: https://www.thehowofbusiness.com/596-shannon-bailey-marketing-and-ai/

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 Shannon Bailey, founder of Make Progress Strategies. Shannon begins by sharing her entrepreneurial journey, from a career in sales and corporate leadership to launching her own consulting firm, and what led her to take that leap into business ownership.

We then explore how AI is changing marketing. Shannon explains why AI doesn't make marketing more technical, but more strategic. As AI platforms synthesize and recommend businesses instead of simply listing search results, vague positioning and generic messaging get exposed quickly.

We discuss why small businesses may actually benefit in this shift, how earned authority now matters more than SEO tricks, and why niching down expands your reach instead of limiting it. Shannon also shares practical steps you can take today, including how to test your visibility using AI tools themselves.

If you're feeling overwhelmed by AI disruption, this conversation will help you refocus on the fundamentals: clear messaging, strong positioning, and speaking directly to your ideal client, while also offering inspiration from Shannon's own path into entrepreneurship.

Shannon Bailey is a strategist and branding and messaging expert. She is the founder of Make Progress Strategies, where she helps small businesses and nonprofits clarify their value proposition, align brand positioning with growth objectives, and build strategic marketing plans that drive action.

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


Henry Lopez hosts The How of Business-How to start, run, grow and exit a small business. It’s a practical resource for anyone who wants to move beyond just the idea of entrepreneurship and into the actual work of building something. Each week, the focus is on the tangible steps and decisions involved in a business’s entire lifecycle, from that initial launch through to managing daily operations, scaling up, and even planning a future exit. You’ll hear straightforward conversations that dig into specific topics, breaking down complex challenges into manageable advice. Often, Henry sits down with a small business owner who shares their real-world experiences-the successes and the setbacks-offering a genuine look at what it takes. This podcast is built on the understanding that running a business is a series of learned skills, and it aims to provide those lessons without fluff. Whether you're sketching your first plan on a napkin or steering an established company toward growth, the discussions here are meant to be directly applicable to your own journey. Tune in for a regular dose of clarity and concrete strategies from someone who understands the day-to-day realities you face.
Author: Language: English Episodes: 100

The How of Business - How to start, run, grow and exit a small business.
Podcast Episodes
604 – Why Partnerships Fail [not-audio_url] [/not-audio_url]

Duration: 21:45
The three root causes of business partnership failure - loss of trust, respect, and alignment - and how to prevent them. Show Notes Page: https://www.thehowofbusiness.com/604-why-partnerships-fail/ Business partnerships…
R306 – 5 Steps to Naming with Brad Flowers [not-audio_url] [/not-audio_url]

Duration: 37:06
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: https://www.thehowofbusiness.com/r306-…
603 – 5 Tips for Better Emails [not-audio_url] [/not-audio_url]

Duration: 18:35
Practical email writing techniques that help small business owners communicate more clearly, get faster responses, and reduce costly misunderstandings. Show Notes Page: https://www.thehowofbusiness.com/603-5-tips-for-bet…
602 – Why Your Business is Stuck [not-audio_url] [/not-audio_url]

Duration: 20:01
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: https://www.thehowofbusiness.com/602-why-your-business-is-stuck/ I…
601 – 2026 Franchise Trends with Giuseppe Grammatico [not-audio_url] [/not-audio_url]

Duration: 45:04
The latest in key franchise trends, including AI-driven efficiency, stronger franchisor support, and high-demand service industries. Show Notes Page: https://www.thehowofbusiness.com/601-franchise-trends-giuseppe-grammat…
600 – Create Your Own Category with Kevin Maney [not-audio_url] [/not-audio_url]

Duration: 41:50
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: https://www.thehowofbusiness.com/600-kevin-man…
599 – When Should You Outsource Your Bookkeeping? [not-audio_url] [/not-audio_url]

Duration: 34:18
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: https://www.thehowofbusiness.com/599-…
598 – Do Your Leaders Know the Score? [not-audio_url] [/not-audio_url]

Duration: 20:50
If your leaders don't know how they're measured, you can't expect consistent performance or real ownership. Show Notes Page: https://www.thehowofbusiness.com/598-do-your-leaders-know-the-score/ Frustrated with inconsiste…
597 – Why Your Business Will Sell [not-audio_url] [/not-audio_url]

Duration: 19:07
Five practical reasons your small business will sell and how to intentionally build long-term exit value. Show Notes Page: https://www.thehowofbusiness.com/597-why-your-business-will-sell/ Most business owners say they w…
595 – Plan to Succeed, but Prepare to Fail [not-audio_url] [/not-audio_url]

Duration: 21:30
Planning improves your odds of success, but accepting risk, making decisions with incomplete information, and learning quickly from failure are what ultimately move a business forward. Show Notes Page: https://www.thehow…