When Portside Advertising marked its 20th year of serving businesses along the Gulf Coast, the Fairhope agency did not throw a party so much as convene a conversation. Its principals invited three long-term clients to a roundtable to look back on two decades of advertising counsel and marketing execution, and to wrestle with a harder question: where does small-business marketing go from here, now that artificial intelligence, smartphones and splintered audiences have rewritten the rules?
The discussion, held in the fall of 2025, brought together Portside founding principal Joe Brown and partner Edward Herndon with Dr. Thomas Bender of Advanced Dermatology & Skin Care; Angelo DePaola, founder of The Coastal Connection at eXp Realty in Orange Beach; and Brent Smith, who owns and operates several Aaron Rents stores along the Gulf Coast. What emerged was a candid portrait of how much has changed for local businesses trying to reach customers, and how much still depends on something old-fashioned: trust.
From Billboards and Radio to a Digital-First World
Brown has worked in advertising far longer than Portside has existed, with earlier stints that included newspaper advertising sales. But he opened the roundtable by returning to 2006, the year the agency traces as its beginning, and to a media landscape that now feels almost quaint.
“Remember newspapers? When we first started, it was all about billboards, radio, print, and television ads. There were no digital platforms at the time, no Google Ads, and Artificial Intelligence wasn’t even a thing. Now digital is everything,” Brown said.
That shift mirrors what has happened across the advertising industry nationally over the same period. In the mid-2000s, smartphones as we know them had not yet arrived, social media was in its infancy, and local businesses on the Eastern Shore and across Mobile and Baldwin counties relied heavily on traditional outlets to build name recognition. Today, many of those same businesses spend a growing share of their budgets on search ads, social media, streaming video and targeted digital campaigns. Over its two decades, Portside has moved deep into that digital world, with video playing an ever-larger role in the messages it creates for clients.
The Struggle to Build a Human Connection
For DePaola, whose business depends on relationships with home buyers and sellers in a competitive coastal real estate market, the central challenge is personal. “Everyone is on their phone. How do you create a brand? It keeps me up at night,” he said.
Brown’s answer pointed squarely at artificial intelligence. “AI is the future. You can create one video and then have AI generate 50 different versions tailored for a very specific audience, with video and audio for just those people. You are seeing more videos targeting specific markets that include an immediate purchase option. Younger people are used to it and respond.”
That capability, sometimes described in the industry as personalization at scale, allows a single creative concept to be adapted for many narrow audiences at a fraction of the cost that producing separate campaigns once required. For small businesses without large marketing departments, it can put tools once reserved for national brands within reach.
Dr. Bender described how the technology is already reshaping customer service in health care and beauty. Website chatbots, he noted, have become prominent in answering questions, booking appointments online and offering purchase options for products. “AI can take your website, find a voice, and generate a person that resembles someone real. Yet, you don’t want to appear too imposing or too aggressive,” he said.
Trust in an Age of AI and Uncanny Ads
Bender’s caution led the group into a broader discussion about authenticity. As AI-generated images, voices and video become more polished, consumers face a growing challenge in separating what is real from what is manufactured.
“I think you can tell when something AI-generated is fake, but it’s harder and harder to tell the difference,” Brown said.
The conversation turned to a phenomenon many smartphone users have noticed: ads that seem to appear after a topic comes up in casual conversation. Brown said there are phone settings users can turn off, but even then, ads seem to follow what people have searched for or mentioned. “It’s uncanny! Ads follow conversations,” he said. Whatever the exact mechanism in a given case, the experience underscores how much data now shapes the advertising people see, and why businesses must be careful not to cross the line from helpful to intrusive.
How Geo-Targeting Puts Local Businesses on the Map
One of the tools the group discussed is geo-targeting, a strategy businesses use to deliver personalized content, advertisements and offers based on a user’s geographic location. Location can be determined through GPS, IP addresses or cellular data, allowing a company to show relevant promotions to people in a specific area.
For a coastal economy like Baldwin County’s, the applications are easy to picture:
- Announcing a local store opening only to people who live or work nearby.
- Promoting products suited to the local climate, such as items that matter in a hot, humid Gulf Coast summer or during hurricane season.
- Reaching visitors while they are in town rather than spending money on audiences hundreds of miles away.
This kind of location-based marketing is becoming more prominent, and it rewards agencies that understand both the technology and the local market it serves.
Brand Trust Still Sells Refrigerators
Smith offered a view from retail, where the path to purchase has changed dramatically. “We relied on top-of-mind name recognition. You don’t need a refrigerator until the one you have stops working. Having a name people trust is important. Our market is now 40% e-commerce. People don’t feel the need to come into a store to purchase. Brand trust is key,” he said.
His point captures a paradox of modern marketing. Even as more transactions move online, the reason a customer chooses one business over another often comes down to familiarity and reputation built long before the moment of need.
Generations, Influencers and the Split-Second Impression
The roundtable spent considerable time on how differently Baby Boomers, Gen X, Millennials and Gen Z take in information, and what that means for crafting a message that works. Brown pointed to influencers as a growing force in building consumer trust.
“Young consumers follow these influencers and trust what they are selling. That’s why you are seeing big consumer product companies rely more and more on influencers to sell products over a recognized spokesperson,” he said.
Attention, he stressed, is the scarcest resource of all. “Social media is huge. People are on their phones all day. You only have a split second to grab someone’s attention. How do you capitalize on that split second? How do you get someone to see a split-second impression and stop to take a closer look at what you have to offer? That is the challenge.”
Brown added that younger buyers are increasingly comfortable purchasing without ever setting foot in a store. “The younger generation doesn’t want to go to a store. They are accustomed to purchasing online, sight unseen. Cars, furniture, and even homes are bought without seeing or touching the product. Influencers and brand recognition play a huge role in building trust. So does word of mouth, people who have had a good experience and are happy to share their experiences through social media. It’s a laying on of hands, so to speak, and it works. It’s a different world from just twenty years ago.”
AI as a Tool, Not a Replacement
For all the enthusiasm about artificial intelligence, the Portside partners were quick to acknowledge its limits. “It’s an impressive and valuable tool, but it still has its flaws,” Herndon said, and the others around the table agreed.
Delivering the right message to the right audience across such different generations, the group concluded, requires constant attention to a digital space that shifts almost daily. That is where Portside aims to earn its keep.
“The key is to build trust in your brand,” Brown said. “It’s about time management for busy people. How do you customize the message to win in the digital age that changes every day? That’s what we do. Our clients rely on Portside to understand the market and how it is responding to change, and to create effective marketing strategies and solutions that take advantage of tools and trends in today’s digital world.”
What Local Business Owners Can Take Away
The roundtable offered lessons that apply well beyond Portside’s client list. For small businesses in Fairhope, Orange Beach, Daphne, Mobile and across the Gulf Coast, several themes stood out:
- Trust is the constant. Channels change, but customers still buy from names they know and believe in.
- Video and mobile matter. With audiences on their phones throughout the day, short, attention-grabbing video has become central to reaching them.
- Know your audience by generation. A message that resonates with Baby Boomers may miss Gen Z entirely, and vice versa.
- Use AI thoughtfully. It can multiply creative output and personalize messages, but it has flaws, and heavy-handed or artificial-seeming marketing can erode the very trust businesses are trying to build.
- Word of mouth has gone digital. Happy customers sharing their experiences on social media remain one of the most persuasive forms of advertising there is.
Twenty years after it got its start, Portside Advertising is betting that the agencies that thrive in the next two decades will be the ones that pair new tools with an old-school understanding of the people and businesses in their own community.
Behind the Agency: How Joe Brown Built Portside
Portside’s story is closely tied to the career of Joe Brown, who described the agency’s roots in a 2023 interview. Brown grew up in Mobile, attended U.M.S. and Murphy High School, and continued his education at the University of South Alabama and Spring Hill College. He got his start in newspaper advertising sales in Mobile. “I liked advertising sales, made many friends, and developed good relationships within the business community,” he said.
After five years in newspaper sales, Brown joined Clear Channel Radio, now iHeartMedia, as an advertising sales representative and worked his way up to Director of Sales, selling advertising on local radio stations across the coastal market. He then went out on his own, forming Joseph Brown & Associates, a full-service firm with a local focus based in Daphne. “Most of what we did was media design, production, and media placement,” he said.
In 2017, Brown partnered with Edward Herndon and the firm took the name Portside Advertising. “Edward was early to the website design world with his company, Webjed, and he brought the needed website design experience. We became a more digitally-driven company,” Brown said.
Clients, Services and Team
Portside’s work ranges from logo design and social media management to full marketing campaigns. “If you live in the Southeast, chances are you’ve seen our work,” Brown said in 2023, naming Waterville USA, SunSouth (John Deere), UJ Chevrolet, Century Bank and Baldwin EMC among its clients.
At the time, the agency had eight project managers and specialists covering graphic design, project management, social media, digital media and video production. Brown said Portside works with clients that have their own marketing departments and those that do not. “We strive for a cohesive message with an actual plan for success. We measure constantly, and we are results-driven,” he said. “Personal service, accessibility, and responsiveness are important to us.”
He was especially emphatic about websites. “We have dozens of clients and are constantly updating and optimizing their websites. Your website is your face to the public and represents people’s image of your company. If you are not keeping your website up to date today, you are hurting your business.”
Outside the office, Brown is an avid golfer who values being within two hours of fishing and his hunting camp, and he recently added a John Deere tractor to his life. His wife, Amy, teaches first grade in Fairhope. “There’s a reason so many people are moving here,” he said. “It’s a great place to live and raise your family.”