Tim Ensmann

Tim Ensmann is the founder of The Boutique Hotel Fund and co-founder of Second Home Stays, where he specializes in transforming overlooked properties into high-performing boutique hotels and experiential destinations.

With a focus on creating one-of-a-kind stays and lasting value, Tim has built a multimillion-dollar portfolio that blends the creativity of short-term rentals with the consistency and scale of boutique hotels. His team develops experience-driven assets that combine the best of both worlds: the uniqueness, space, and amenities travelers love about vacation rentals, and the quality, service, and efficiency that define great hotels.

Before entering hospitality, Tim built a successful career in tech and sales leadership. His background in enterprise sales at AI companies now shapes his approach to building tech-enabled, frictionless guest experiences that drive loyalty and profitability.

His most recent acquisition, The PineTree Hotel in Idyllwild, California, tripled in value within two years and became a viral success with more than 25,000 followers. Through that success, Tim proved that hospitality can be both profitable and purposeful. Today, he and his partners are scaling that model across high-demand lifestyle markets through The Boutique Hotel Fund.

Passionate about empowering investors and operators, Tim helps others create wealth and build intentional lives through boutique hotel ownership, where financial freedom meets meaningful experiences.