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
551: The 5 Stages of Entrepreneurship [not-audio_url] [/not-audio_url]

Duration: 23:18
From Self-Employed or Solopreneur through Serial Entrepreneur—what does it look like and what does it take, to go from running a one-person operation to managing a portfolio of successful businesses and creating a lastin…
550: Super Communicators with Charles Duhigg [not-audio_url] [/not-audio_url]

Duration: 44:35
Super Communicators - how to unlock the secret language of connection with journalist and the author Charles Duhigg. Show Notes Page: https://www.thehowofbusiness.com/550-charles-duhigg-super-communicators/ In this episo…
549: Human Resources with Claudia St. John [not-audio_url] [/not-audio_url]

Duration: 49:08
Small Business Human Resources management with Claudia St. John. Show Notes Page: https://www.thehowofbusiness.com/549-claudia-st-john-human-resources/ Are you struggling with hiring, retaining top talent, or building a…
548: 2024 Top 5 Episodes [not-audio_url] [/not-audio_url]

Duration: 13:36
Highlights from 2024 Top 5 Episodes, based on unique listener downloads. Show Notes Page: https://www.thehowofbusiness.com/548-2024-top-5-episodes/ Discover the most popular episodes of 2024, based on listener downloads,…
547: Lessons from The Art of Shaving with Eric Malka [not-audio_url] [/not-audio_url]

Duration: 45:31
Lessons from The Art of Shaving: starting, growing, and selling The Art of Shaving company. Show Notes Page: https://www.thehowofbusiness.com/547-eric-malka-the-art-of-shaving/ On this episode, Henry Lopez is joined by E…
R504: Strategic Planning for Small Business [not-audio_url] [/not-audio_url]

Duration: 28:04
How to create a Strategic Plan for your small business. Use a Strategic Plan to set your goals, objectives and initiatives for your small business. Show Notes Page: https://www.thehowofbusiness.com/r504-strategic-plannin…
546: Power Washing Franchise with Aaron Harper [not-audio_url] [/not-audio_url]

Duration: 55:54
How to own a successful Power Washing franchise small business with Aaron Harper. Show Notes Page: https://www.thehowofbusiness.com/546-aaron-harper-power-washing-franchise/ On this episode we dive into the world of fran…
R255: Overcoming Fear with Ruth Soukup [not-audio_url] [/not-audio_url]

Duration: 30:34
Overcoming Fear to start and grow your small business, with Ruth Soukup - author of "Do It Scared: Finding the Courage to Face Your Fears, Overcome Obstacles, and Create a Life You Love". Show Notes Page: https://www.the…
545: Take Control of Your Time with Andrew Hartman [not-audio_url] [/not-audio_url]

Duration: 50:02
How to take control of your time, and trade stress, overwhelm and anxiety for peace, freedom and clarity, with Andrew Hartman. Show Notes Page: https://www.thehowofbusiness.com/545-andrew-hartman-take-control/ Andrew Har…
544: Top 10 Productivity Tools [not-audio_url] [/not-audio_url]

Duration: 9:13
Henry's Top 10 Personal & Business Productivity Tools. Show Notes Page: https://www.thehowofbusiness.com/544-top-10-productivity-tools/ In this episode of The How of Business, host Henry Lopez shares his current top 10 p…