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
534: Before You Spend on Marketing... [not-audio_url] [/not-audio_url]

Duration: 20:06
You need a Marketing Strategy before you spend on marketing or advertisement for your small business. Show Notes Page: https://www.thehowofbusiness.com/534-before-you-spend-on-marketing/ Henry Lopez, host of The How of B…
533: Travel Consulting Business with Pam Lopez [not-audio_url] [/not-audio_url]

Duration: 48:35
Experiences and insights from operating her successful Travel Consulting small business and working with her spouse and other family members in a small business. Show Notes Page: https://www.thehowofbusiness.com/533-pam-…
532: Is Your Business Model Broken? [not-audio_url] [/not-audio_url]

Duration: 20:50
Is Your Small Business Model Broken? Show Notes Page: https://www.thehowofbusiness.com/532-broken-business-model/ Is your small business model broken? How can you tell, and how do you fix it? And what do I mean by a Busi…
531: Growing a Medical Practice with Dr. Rao [not-audio_url] [/not-audio_url]

Duration: 49:03
How to grow a Medical Practice with Dr. Ramesh Rao. Show Notes Page: https://www.thehowofbusiness.com/531-dr-rao-growing-medical-practice/ Dr. Ramesh Rao shares his immigrant and entrepreneurial journey and his insights…
530: Complex Decision Making [not-audio_url] [/not-audio_url]

Duration: 56:19
How to make Complex Decisions in your small business. Show Notes Page: https://www.thehowofbusiness.com/530-complex-decision-making/ Learn more about Complex Decision Making with co-hosts Henry Lopez and David Begin. How…
529: Etsy Business with Dylan Jahraus [not-audio_url] [/not-audio_url]

Duration: 39:38
How to build a Multi-Six Figure Etsy Business with Dylan Jahraus. Show Notes Page: https://www.thehowofbusiness.com/529-dylan-jahraus-etsy-business/ Etsy is the global marketplace for unique and creative goods. Etsy offe…
528: Home Service Business Millionaire with Tommy Mello [not-audio_url] [/not-audio_url]

Duration: 50:41
How to become a Home Service Business Millionaire with Tommy Mello. Show Notes Page: https://www.thehowofbusiness.com/528-tommy-mello-home-service-millionaire/ Tommy Mello shares his inspiring entrepreneur journey, how h…
527: Google Ads for Small Business [not-audio_url] [/not-audio_url]

Duration: 42:20
Google Ads for Small Business with digital marketing expert Adam Mann from Oostas. Show Notes Page: https://www.thehowofbusiness.com/527-small-business-google-ads/ From a non-technical perspective, Henry and Adam share t…
526: Decision Making [not-audio_url] [/not-audio_url]

Duration: 44:57
Embracing and improving decision making for small business owners, with hosts Henry Lopez and David Begin. Show Notes Page: https://www.thehowofbusiness.com/526-decision-making/ As the business owner, you, and perhaps yo…
525: Managing Perfectionism with Greg Chasson [not-audio_url] [/not-audio_url]

Duration: 46:48
Managing perfectionism in the small business workplace with Greg Chasson. Show Notes Page: https://www.thehowofbusiness.com/525-greg-chasson-managing-perfectionism/ How do we understand and mitigate the negative impacts…