Meet The Team

FOUNDER

Matthew Blesso is a real estate developer, entrepreneur, and community builder dedicated to creating regenerative living environments that foster wellness, connection, and harmony with nature. He founded Blesso Properties in New York in 1996, leading transformative projects that combine innovation, sustainability, and social impact. To date, the firm has completed 17 developments across New York, Panama, and Costa Rica, earning eight design awards, breaking multiple pricing records, and being featured in leading publications worldwide. Matthew also founded Tántalo Hospitality Group in Panama in 2010, which owns and operates two of the country’s most iconic cultural destinations that unite art, design, and entertainment. In Brooklyn, he co-founded 3rd Ward, a creative hub that became a catalyst for entrepreneurship and artistic collaboration. Through all his ventures, Matthew champions a vision of development that elevates both people and planet, shaping communities where social impact and profits thrive side by side.

DIRECTOR OF DEVELOPMENT

Raymond Brealey is Partner and Director of Development at Shift Living. He brings more than 24 years of experience leading complex real estate projects across Costa Rica. His background blends civil engineering, construction management, and disciplined risk control to deliver on time and on budget. Raymond has completed more than 100 projects spanning residential communities, hospitality, mixed-use, and infrastructure. Before Shift, he held senior development roles in Costa Rica where he oversaw pre-construction, permitting, procurement, and field execution for large-scale programs. He holds a BS in Civil Engineering, an MS in Project Management from the University of Texas, and an MBA. At Shift Living he directs the full development lifecycle, from master planning and contractor selection to cost optimization and delivery, aligning technical execution with the company’s regenerative mission.

DIRECTOR OF DESIGN & INNOVATION

Matthew’s wife, Ginger, harnesses her expertise from Pratt, Parsons, and the Art Students League to lead interior design, art curation, and furniture design, ensuring all design projects align with Shift's vision. Ginger is currently exploring Bio-Design, using living organisms for sustainable, innovative materials.

SALES DIRECTOR & MARKETING STRATEGIST

Oscar is a seasoned real estate marketing consultant based in Costa Rica, with over 20 years of experience in sales and marketing, media management and experiential production. He brings a distinctive blend of creative vision and operational expertise, shaped by his background as a founder and leadership roles in some of the most prestigious master-planned communities throughout the region.

SALES AGENT & COMMUNITY BUILDER

Dustin has over 20 years of experience in management, destination real estate, and sales, combining a strong work ethic with a relationship-driven approach to business. Outside of work, he enjoys spending time with his family, surfing, hiking, mountain biking, and exploring the outdoors. For him, life is about maintaining balance, staying active, and appreciating the simple moments.

MARKETING ASSOCIATE

Jessica holds a degree in Digital Marketing and joined Shift in 2025 as a Marketing Associate. She supports a variety of marketing tasks across the company and was drawn to Shift by its strong sense of community and positive work culture. Outside of work, she enjoys listening to jazz with friends, reading, and exploring anything related to fashion.

OFFICE MANAGER

Mari brings over four years of experience in hospitality, tourism, and administration, overseeing Shift Esperanza’s daily operations and managing USA bank accounts while supporting the leadership team. Originally from Nicaragua, her passion for sustainable design aligns perfectly with Shift’s vision. Outside of work, Mari is an avid reader and enjoys exploring Human Design.

ACCOUNTING MANAGER

Jennifer is a CPA currently pursuing Master's degrees in Project Management and Tax Advisory. She has experience working with companies across the Caribbean, the U.S., and India, with a strong focus on Transfer Pricing in the tech sector. She joined Shift inspired by its values and unique mission in Costa Rica. Outside of work, she's a proud mom who enjoys reading, podcasts, good food, and volunteer work.

FARM MANAGER

Holding a degree in Biosystems Engineering, Emanuel joined Shift in 2023 as the Farm Manager, leveraging his deep agricultural roots from Costa Rica and extensive experience in both agriculture and the electric industry. Working at Shift gives Emanuel a chance to apply this knowledge by helping the project restore healthy ecosystems, conscious food production, protection of water resources, residue management, and positive social impact.

NURSERY AND SOIL FERTILITY MANAGER

Originally from Heredia, Daniela is an agronomic engineer passionate about permaculture and sustainable agriculture. At Shift Esperanza, she manages the nursery and soil fertility at Finca La Esperanza, combining her love for nature with holistic living. Outside work, Daniela enjoys hiking, birdwatching, yoga, and exploring Latin American literature, philosophy, and culture.

LEAD LAND DESIGNER

Sam Kenworthy is a water systems enthusiast and landscape manager with over a decade of experience in the tropics. Experienced in working in a wide variety of environments, he enjoys the challenge and process of designing around problematic landscapes. Dedicated to continued learning and improving his skill sets, he is passionate about self-sufficiency, water management, generating more and better yields, and well-executed design for human ecosystems.