New York, New York – September 15, 2025 – Castle Peak Holdings, (“Castle Peak” or “CPH”), the investment firm behind Trailborn Hotels & Resorts, today announced the appointment of David Goldstein as Managing Director of Strategic Operations.
At Castle Peak, Goldstein will be responsible for creating value by integrating performance improvement initiatives, CapEx projects and organizational design across the firm’s real‑estate portfolio and affiliate operating businesses. He will play an integral role in the firm’s asset‑level business plan execution, investment lifecycle planning, and corporate strategy.
“Dave’s proven track record consists of unique cross‑disciplinary expertise that allows us to continue delivering memorable experiences to our guests, and differentiated, unlevered value creation to our capital partners,” said Ben Weinberg, Co‑CEO and Co‑Founder of Castle Peak. “We are thrilled to welcome him as we continue to strengthen our execution machine and platform‑building capabilities to position our firm for long‑term scale and success.”
Goldstein brings over two decades of executive experience in hospitality operations, asset management, and private‑equity‑backed platform oversight. Most recently, he served as Head of North America Hospitality on the Strategic Operations Team at KSL Capital Partners, where he led asset repositioning, operational performance initiatives, and capability building across a diverse portfolio of hotels, resorts, and platforms, including Hotel del Coronado, Grand Wailea, Miraval Resorts, Fairmont Grand Del Mar, and the Monarch Beach Resort. Goldstein also served on the Board of Directors at several hospitality development companies, including Davidson Hospitality Group, Outrigger Hospitality Group, Tortuga Resorts, and Hersha Hospitality Trust.
Throughout his career, Goldstein has been instrumental in creating value at scale, spearheading CapEx projects, and designing organizational systems. His experience spans acquisitions, due diligence, and integration, having worked on over $10 billion in transactions across landmark properties and hospitality platforms.
“Dave’s arrival marks another important step in Castle Peak’s evolution. His deep experience in aligning operational excellence with brand and real‑estate strategy will allow us to accelerate Trailborn’s momentum and expand our ability to deliver authentic, elevated experiences in the destinations that matter most to our guests,” said Mike Weiss, Co‑CEO and Co‑Founder of Castle Peak. “We’re excited to have his leadership as we continue to scale thoughtfully and build lasting value for our partners.”
Goldstein holds both a Master of Tourism Administration and a Bachelor of Business Administration from The George Washington University School of Business. He is an active member of the Urban Land Institute and its Recreation Development Council, the Hotel Asset Management Association, and the American Hotel & Lodging Association, and serves on the Board of Directors at the International School of Denver.
Launched in 2021 by two Goldman Sachs alums, Castle Peak created a unique playbook to scale niche real‑estate platforms, combining fundamental supply‑demand imbalances, deep sector expertise and a “one at a time” approach to deliver outsized outcomes. Since the firm debuted Trailborn Hotels & Resorts in 2023, the outdoor hospitality brand has seen rapid momentum. In 2024, Trailborn entered into a long‑term agreement with Marriott to add the brand’s portfolio to Marriott’s system. In just over a year, the brand has opened five distinct properties, including Trailborn Rocky Mountains & Trailborn Rocky Mountains Outpost in Estes Park, Colorado; Trailborn Highlands in North Carolina’s Blue Ridge Mountains; Trailborn Surf & Sound in Wrightsville Beach, North Carolina; and most recently, Trailborn Grand Canyon in Williams, Arizona, with more locations coming in Mendocino, California and Jackson Hole, Wyoming.
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