Built by letting managers, for letting managers

Foundations was born out of years running a holiday letting business, and the frustration of never having a tool that understood the job.

Where it started

William and Jack Matthews have been involved in the holiday lettings business for almost all their lives. They cut their teeth in a family-owned agency covering North Wales. Jack oversaw day-to-day operations as managing director. William focused on marketing and growth as commercial director.

When the time came for the family to part ways with their company, it merged with one of the UK's largest letting agencies. Jack joined and rose through the ranks to become a regional director. William moved into luxury travel and events.

Five years on, they felt it was time to apply their experience to something new. They launched Oyster Holiday Cottages, a full-service letting agency built on local knowledge, personal service, and a deep understanding of what owners and guests actually need.

Running Oyster day-to-day made one thing clear: the tools available to letting managers hadn't kept up. That's what led to Foundations. When they started showing it to other letting managers, the response was always the same: "We need this too."

William Matthews

Commercial & Marketing

William leads commercial and marketing at Foundations. He's a water baby. In his spare time you'll find him sailing his Fife in Beaumaris, kite-boarding in Rhosneigr, or trying to beat his personal record for climbing all 14 of Wales' 3,000-feet peaks. Married to Emily, a yoga and pilates instructor, William has a young son, Cosmo.

William Matthews
Jack Matthews

Jack Matthews

Operations & Compliance

Jack leads operations at Foundations, and is the reason the compliance module exists. He's a passionate countryman and a keen fly-fisherman. Often found exploring the coasts of Anglesey to fish for bass, he also helps out from time to time on his father's beef cattle farm in the Llŷn Peninsula. Married to Millie, an experienced events planner, Jack has two young children, Maisie and Paddy.

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