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: 50

The How of Business - How to start, run, grow and exit a small business.
Podcast Episodes
R361 – Start and Grow Without Investors with Tyler King [not-audio_url] [/not-audio_url]

Duration: 43:44
How to start and grow a small business without investors. Show Notes Page: https://www.thehowofbusiness.com/r361-tyler-king-without-investors/ Bootstrapping a software business without venture capital or angel investors…
619 – Presentations That Close Deals with Dean Curtis [not-audio_url] [/not-audio_url]

Duration: 39:27
Increase Close Rates with consistent, professional in-home sales presentations for home improvement and home services businesses, and Dean Curtis of Ingage shares the principles and tools that help small operators win mo…
618 - Buyer Due Diligence [not-audio_url] [/not-audio_url]

Duration: 24:34
Buying a Business? Do Your Due Diligence! Show Notes Page: https://www.thehowofbusiness.com/618-buyer-due-diligence/ Buyer due diligence is your primary protection when purchasing a small business, and on this episode He…
617 - Remote, Hybrid, or In-Office? with Claudia St. John [not-audio_url] [/not-audio_url]

Duration: 38:49
Deciding between remote, hybrid, and in-office work is one of the toughest calls small business owners face today, and HR expert Claudia St. John shares how to choose the model that fits your team while staying legally c…
616 - Parkinson's Law for Small Business [not-audio_url] [/not-audio_url]

Duration: 21:28
Why work expands to fill the time available, and how small business owners can use deadlines, time blocking, and clear outcomes to get more done in less time. Show Notes Page: https://www.thehowofbusiness.com/616-parkins…
615 - AI and Cybersecurity for Small Business with Mordy Hackel [not-audio_url] [/not-audio_url]

Duration: 47:33
Technology expert explains how small business owners can leverage AI as a force multiplier while protecting their data, systems, and intellectual property from emerging cybersecurity risks. Show Notes Page: https://www.t…
614 - Growing a Family Business with Kaiden Routh [not-audio_url] [/not-audio_url]

Duration: 39:34
How he earned his way into leadership, developed a capable management team, and transformed a hands-on family equipment dealership into a scalable business that no longer depends on him for every decision. Show Notes Pag…
R346 - The 6 Traits of Entrepreneurs [not-audio_url] [/not-audio_url]

Duration: 20:41
Do you possess the innate characteristics, the 6 essential traits, required to become a true entrepreneur? Show Notes Page: https://www.thehowofbusiness.com/r346-6-traits-of-entrepreneurs/ How to honestly assess whether…
613 - Conflict Resolution Principles with Jeremy Pollack [not-audio_url] [/not-audio_url]

Duration: 51:03
How understanding the neuroscience behind conflict can help small business owners become more effective leaders, build healthier teams, and transform workplace conflict into collaboration. Show Notes Page: https://www.th…
612 - What a Waymo Ride Taught Us About Innovation [not-audio_url] [/not-audio_url]

Duration: 30:46
A Waymo driverless vehicle ride sparks a discussion about AI, innovation, technology adoption, and why small business owners can't afford to wait for perfection before embracing emerging technologies like AI. Show Notes…