Raised in Connecticut, Josh ventured west to the Silicon Valley after high school to attend Santa Clara University. Armed with a BS in Economics, and a keen interest in real estate, Josh launched his career in commercial real estate brokerage in Palo Alto. After two years in the brokerage business, a client hired him to help develop, build and sell 160 condominiums ($60M in sales) at The Boulders in North Lake Tahoe, California. At The Boulders, Josh further honed his knowledge of construction, marketing and sales, and ultimately founded Boulders Realty to act as Broker of Record for the project. During this period, Josh met his future life partner, Erin Flanagan, and they married in 2007. With Josh’s background in real estate and Erin’s in marketing, they formed a strong team that appealed to the owners of Calistoga Ranch, and in 2008 they were hired as Director of Real Estate and Marketing Director, respectively. Six years later, with 140 fractional memberships and six residences sold ($72M in sales), the real estate offering at Calistoga Ranch is complete, and Josh is now applying his experience accrued over 13 years in real estate sales, marketing, development and customer service as Broker Associate at Coldwell Banker.
One of Josh’s passions is meeting new people. Inquisitive by nature, his demeanor is both analytical and approachable which, along with a strong work ethic, enables Josh to strike the perfect match between the clients and their dream properties. Josh has a deep love for Napa Valley, not just as a tourist destination, but as a warm, inclusive place to raise a family. Erin and Josh now have two young children, and are permanently settled in St. Helena where they are raising their family. When Josh isn’t working or being a Dad, you might find him on a surfboard, a snowboard, or a bike.
Erin was raised in Colorado and attended the University of Kansas, earning a BS in Journalism. Upon graduation, she set her sights on the west coast and moved to San Francisco where she worked in media buying for J. Walter Thompson. Having grown up in the mountains, Erin was drawn to the Lake Tahoe area where she worked as a leasing agent for the Village at Northstar. She went on to become the Marketing Manager for the Hyatt at Northstar, and during that time met her future husband, Josh Dempsey. In her position as Director of Marketing at Calistoga Ranch, one of the Napa Valley’s most exclusive resorts, Erin managed the PR, print and online advertising, website, client outreach programs, photo and video shoots and direct mail efforts. With such an extensive background in real estate marketing, she brings a unique perspective to JD Napa Valley and a keen eye to marketing initiatives effective in selling your property.