How Group Travel Helped Matthew Schueller Build Community

A year after his first appearance on the show, Matthew Schueller returns to catch Bryan up on an enormous year of growth — from one experimental group trip to Greece in 2024 to eleven trips and counting, and the launch of a full-fledged business, Side Quest Travel. Bryan and Matthew talk about what's changed as the trips have scaled from a fun side project into a real company with real logistics, real hiring decisions, and a real waitlist of destinations.

At the heart of the conversation is why these trips work: Matthew builds community before the trip even starts, using WhatsApp groups and monthly video calls so travelers — many on their first-ever trip outside their home country — arrive already knowing each other. Matthew opens up about his own struggles with loneliness and not feeling like he fit in, even within the LGBTQ+ community, and how that experience shaped a travel brand built to make everyone feel like they belong.

Bryan and Matthew also get into the nuts and bolts of building a hospitality-adjacent business as a first-time entrepreneur — figuring out when and how to hire, learning to set personal boundaries, and planning for a more family-friendly future as Matthew and Michael expect a baby of their own. They close on a note that will resonate with anyone building a personal brand: the hidden hours of work behind an 'easy-looking' 30-second clip, and why persistence beats talent when it comes to content creation.