In this episode of Dealmaker$, we sit down with Sean and Jennifer Degnan—the powerhouse couple behind iTrip Vacations Annapolis. With a blend of corporate expertise and entrepreneurial spirit, they left behind careers in tech, finance, and media to build one of the most trusted short-term rental agencies in Maryland.
From managing high-end homes in historic downtown Annapolis to scaling a full-service hospitality brand during a pandemic, the Degnans share how they turned a personal passion into a thriving business. We dig into their strategy for maximizing property income, delivering five-star guest experiences, and supporting investors who want to break into the short-term rental game.
You’ll hear how they divide roles as co-founders and spouses, what they’ve learned about Annapolis’s rental market, and how they’re redefining what it means to be a hands-on operator in a tech-enabled world.
👉 For more info: https://annapolis.itrip.co 🔔 Subscribe for weekly episodes featuring top real estate pros, dealmakers, and builders of bold businesses.
Timestamps: 0:00 – Intro 2:35 – Their origin story: Georgetown to Annapolis 9:40 – Launching iTrip during COVID 15:00 – Business strategies that actually work 24:20 – Managing investor-owned properties remotely 31:15 – Scaling while keeping it personal 39:50 – Signature deals and top-performing rentals 45:05 – Rapid-fire Q&A 49:00 – Final takeaways + how to connect
Whether you’re an agent, investor, or someone fascinated by the business of short-term rentals and real estate entrepreneurship — this one’s for you. 👥 Guests: Sean & Jennifer Degnan 📸 Instagram: @itrip_annapolis 🌐 Website: annapolis.itrip.co
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