“They said they had it but they didn’t use or update it,” he says. “Not once in two and a half years, and that is so typical for most companies. People do the exercise once and never look at it again.”
Treating a persona as a one-time assignment is a fatal flaw. If you lose track of how your customers’ needs evolve, you lose connection with them.
Stories turn strategy into connection
Once a business knows who it is speaking to, it has to decide what to say. For Plebon, the answer is simple: tell your story.
He points to Mid-Day Squares, a Montreal startup founded in a condo kitchen that became a national snack bar brand by turning their wins, failures, and even fights into a public narrative.
They caught on by letting people behind the curtain, serving as a case study in how authenticity builds loyalty.
“They told their story — the good, the bad, the ugly. Their therapy sessions. Moments where they almost gave up. And people plugged into it,” Plebon explains.
Every entrepreneur experiences triumphs and setbacks. Sharing these moments, rather than just the successes, creates an emotional bridge to their audience.
“That’s what attracts attention,” Plebon notes. “People don’t just want the widget. They want the story behind it because that’s what makes them connect.”
Simplifying AI use
For already-overextended entrepreneurs, learning to use AI can feel like another burden.
“People get overwhelmed because they think they need to understand every tool,” Plebon explains. But what matters is how you use the tool.”
By using AI tools in his own work, Plebon says he’s saved time building detailed personas and testing whether content resonates with them.
“I can ask AI to act as a customer and review content,” he explains. “It pulls things out you missed, and it just makes things so much easier. What used to take a week can now be done in an afternoon.”
But generating better and faster results, Plebon says, is only possible when the person guiding the tool uses judgment. AI can refine your voice, but it can’t invent the story behind your business.
Adapting to a field in constant motion
Given how quickly digital marketing evolves, Plebon often tweaks his course content to stay current.
“Every semester I have to update 30 per cent of my course because things change so fast,” Plebon notes.
For those new to marketing, that rapid pace can feel discouraging. But even as tools and trends change, the foundational elements never lose importance.
“Tools and platforms will keep changing,” Plebon notes. “What matters is how you use them. Your insight. Your practice. Your story. That is the part that will always matter most.”
In the face of constant change, Plebon advocates for a focused approach to digital marketing.
“You can’t be everywhere and you don’t have to be everywhere,” he explains. “If you know who you’re talking to and you tell your story with consistency, you’ll find your stride.”