Playing Monopoly In Real Life with Josh Hatter

Josh Hatter is the Founder and Chief Executive Officer of Curated Vacation Properties (CVP), a boutique short-term rental and property management company headquartered in Charleston, South Carolina. Since founding CVP in 2016, Josh has grown the company into a 3-time Inc. 5000 honoree (2023, 2024, 2025), with a portfolio of 140+ active listings, 400+ bedrooms, $13M+ in annual bookings, and $150M+ in real estate under management. CVP’s long-term target—CVP 2030—is to scale to $10M in EBITDA by 2030.Josh is also the Founding Director of KEYS Collective, a 501(c)3 nonprofit mastermind that equips professionals with the knowledge and support to transition from corporate employment to hospitality real estate ownership. KEYS Collective provides education, mentorship, and peer support with a goal of helping 1,000 individuals achieve financial independence through STRs, B&Bs, and boutique hotel investments.In addition to his leadership at CVP and KEYS Collective, Josh is Managing Partner at Phoenix Capital Management (PCM) and CEO at Trouvaille Collection. PCM manages $15M in real estate and equities with a focus on coastal STR investments. Josh is co-founder and CEO of the Trouvaille Collection brand of boutique B&Bs, including two 9-bedroom properties in downtown Charleston,SC and a 16-key boutique hotel in Savannah, GA.Prior to his transition into real estate, Josh held executive and senior leadership roles in the federal contracting and defense sectors. He served as Vice President of Capture at ISHPI and held various leadership roles at SAIC and General Dynamics Information Technology, where he helped drive over $15B in contract awards and developed strategic business development processes across NAVWAR and other various DoD/Federal markets.