We’re pleased to shine a spotlight on Dan Shepard, a dedicated Rutland County landlord who has partnered with Pathways Vermont since 2020 to provide apartments for our Department of Corrections (DOC) Housing Program.
Dan and his business partner, Josh Mossey, have grown their rental portfolio from 50 to over 100 units since 2019. It’s a testament to their commitment to both business growth and community impact.
Today, they lease seven of those units to Pathways Vermont participants, offering safe, stable housing to individuals reentering the community after incarceration.
Dan and Josh reinvest in their properties regularly, encourage tenants to request maintenance, and even dedicate a week each year – “Deck Week” – when they roll up their sleeves and work alongside a carpenter to complete hands-on repairs and upkeep themselves.
They believe that high-quality units encourage tenants to take pride in their homes, and they work hard to keep their properties in excellent condition. Their thoughtful approach and willingness to offer some of their best units to Pathways clients make a real difference.
We’re grateful for Dan and Josh’s partnership, and for their commitment to creating safe, stable housing – a win for landlords, tenants, and our community.

“Deck Week”

