Short-term rentals reward operators who think like hoteliers—not landlords.

In this episode of Dealmaker$, Shane sits down with Sean and Jennifer Degnan, co-founders of iTrip Vacations Annapolis, to unpack how they built a full-service hospitality business in one of the most regulated and competitive rental markets in the region.

After leaving careers in tech, finance, and media, the Degnans turned a personal interest in hospitality into a scalable operation managing high-end homes throughout Annapolis. They share how launching during COVID tested every assumption they had, and why systems, communication, and guest experience became non-negotiable pillars of their growth.

The conversation explores:
• How Sean and Jennifer transitioned from corporate careers to entrepreneurship
• What separates professional STR operators from casual hosts
• Maximizing owner returns without sacrificing guest experience
• Navigating Annapolis regulations and market constraints
• How they divide roles as co-founders and spouses
• Supporting investors who want passive income without passive oversight
• Scaling a service business while keeping standards high

This episode isn’t about quick wins or side hustles. It’s about treating short-term rentals as a real operating business—one that demands discipline, transparency, and constant attention to detail.

Whether you’re an investor evaluating STR opportunities, an agent advising clients on rental strategies, or an entrepreneur curious how modern hospitality businesses are actually built, this is a practical, behind-the-scenes conversation with operators who’ve done it the hard way.

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