In this episode of Dealmaker$, Shane sits down with Sean and Jen Degnan, the husband-and-wife team behind iTrip Annapolis — a short-term rental operation that’s become a trusted name from downtown Annapolis to Kent Island to the Eastern Shore. With backgrounds in tech, finance, advertising, and sales, the Degnans fuse operational rigor with hospitality instincts, managing everything from chic historic homes to full-scale waterfront escapes.

What makes their story remarkable is when they launched: April 2020 — at the bottom of the stock market and the start of a global shutdown. Forced into fully remote training, no in-person real estate office visits, and a total freeze in early tourism, they built their early book of business through resourcefulness, relationship-driven outreach, and sheer belief.

Shane and the Degnans dig into:

• Their Georgetown origin story and the “organized chaos” mindset that makes them perfect partners

• The leap from corporate careers to entrepreneurship — and selling investments at the literal bottom to fund the franchise

• How COVID unexpectedly accelerated their growth as staycations and remote work exploded

• Why Navy connections and deep local presence give them an edge national platforms can’t touch

• Their two-hire decision that changed everything — transforming operations and scaling from 20 to 40 to 60+ properties

• How they price, analyze, position, and onboard STR properties using dynamic tools, local knowledge, and data from 77 homes

• The difference between investor clients and emotional homeowners — and why the best STR owners treat it like a true business

• The realities of STR management: trash runs, maintenance triage, “noise monitors,” fraudulent bookings, and some wild guest stories

• Why they now have the confidence to say no — and how walking away from the wrong owners has actually strengthened their brand

The Degnans also open up about the learning curve, the toughest calls they’ve had to make, hiring the right people, raising three kids while building a company, and the freedom (and chaos) that comes with running a business you can manage from anywhere.

Whether you’re an investor, agent, STR host, or someone who loves hearing the real stories behind hospitality entrepreneurship — this conversation is packed with insights, honesty, and the playbook behind a fast-growing local brand.

This is Dealmaker$ — where real stories meet real strategy.