Interview With Gabriel Caballero aka The Don

Most barbers overlook one of the most meaningful roles they can play in their clients’ lives—being someone who doesn’t just shape how they look, but how they show up in the world. Gabriel Caballero, a proud Montreal barber, business owner, and content creator, has turned his chair into an unexpected matchmaking hub by simply doing one thing: showcasing his single clients after a fresh cut and letting people know they’re available.What started as playful social media posts turned into real dates, real connections, and a community that trusts him far beyond hair. But before any of that, Gabriel had his own journey—finding his path to barbering, building a business from the ground up, and bringing his unique personal background and culture into everything he does. He reps Montreal hard, and that pride in his city and roots shapes the energy of his shop and the way he connects with people.In this episode, we talk about how Gabriel became a barber in the first place, what pushed him to open his own space, and how his life experiences influenced the way he approaches clients—not just as heads to cut, but as real people with stories, insecurities, and hopes. His videos aren’t about creating celebrities—they’re about showing who someone really is after they’ve been given a little boost of confidence. That simple idea has led to clients meeting people, going on dates, and walking out of the shop with more than just a new look.We also dig into what it means to build genuine relationships with clients—how to balance being a professional with being someone people open up to, and how emotionally involved a barber can become in the lives of the people in their chair. Gabriel shares how he stays grounded as a business owner, avoids burnout, and keeps his content authentic instead of performative.At its core, this conversation is about the human side of barbering, entrepreneurship, and connection—how a guy from Montreal followed an unconventional path, built something of his own, and ended up helping people feel confident enough to put themselves out there.Whether you’re a barber, a creator, or just someone who believes confidence changes everything, this episode shows how being yourself—and helping others feel like themselves—can create opportunities no algorithm could ever fake.Chapters00:00 Introduction and Podcast Experience05:00 Maintaining Energy and Boundaries09:59 Transition to Barbering Career15:07 Client Feature Videos and Responses19:54 Managing Social Media Presence25:06 Dating and Social Media Engagement30:20 Attractiveness and Compatibility36:14 Appreciation for Latin Culture and Identity41:29 Promotion and Contact Information