Who we are

Spyglass Vantage is an owner-side advisory firm focused on unlocking real estate value through hospitality.

We help investors, owners, and lenders evaluate, reposition, and optimize hospitality assets — from stand-alone hotels and resorts to hospitality-driven mixed-use environments and experiential destinations.

Hospitality can be a powerful competitive advantage. It can also introduce complexity, capital risk, and operational challenges when misaligned with investment strategy. Most hospitality underperformance is structural — and Spyglass Vantage exists to remove the barriers that limit asset performance. We bring clarity at the intersection of capital, concept, and operations — ensuring hospitality investments are intentional, right-sized, operationally viable, and value-enhancing.

Our work spans the full lifecycle of hospitality integration:

  • Early insight and investment evaluation

  • Strategic planning and partner selection

  • Owner-side implementation and oversight

  • Performance improvement and restructuring advisory

We are independent, operator-agnostic, and aligned solely with the owner’s interests. Our role is not to sell brands, concepts, or services—but to help owners see the full picture and make informed decisions that protect and grow asset value.

As Spyglass Vantage grows, we partner with like-minded advisors who share the same owner-first philosophy, deep domain expertise, and commitment to disciplined execution.

Founder - Jared Flagg, CHAM

Jared Flagg founded Spyglass Vantage on the belief that hospitality-driven real estate value is created at the intersection of capital strategy, development execution, and operational performance. His career spans all three, offering owners and investors a rare, integrated perspective on optimizing asset value.

Prior to founding Spyglass Vantage, Jared served as Managing Director of Asset Management at Silverwest Hotels, where he helped build an institutional-quality hotel investment platform and brand-approved management company from the ground up. Over the course of a decade, he directed more than $500 million in hospitality assets, including ground-up developments in Colorado’s ski markets and the repositioning of iconic resorts in Hawaii. His role spanned the full investment lifecycle—from underwriting and acquisition through development, operations, and disposition.

That leadership role was informed by a career spent in nearly every seat at the hospitality real estate table. Earlier, Jared worked in resort development and ownership with Lowe Enterprises and Destination Hotels, supporting a $1 billion portfolio of destination assets and helping drive meaningful growth in revenue and profitability. He gained deep operational insight working alongside independent management teams while asset managing the same resorts he helped develop, bridging the gap between ownership objectives and on-the-ground execution. Prior to Lowe Enterprises, he worked on the capital side as a commercial lender with Comerica Bank, underwriting and managing real estate credit.

Across these roles, Jared has led through both expansion and disruption, including hospitality restructurings during the Global Financial Crisis and portfolio stabilization efforts during the COVID-19 pandemic. These experiences reinforced the importance of alignment — between concept, capital, partners, execution, and operations — and shaped his ability to diagnose complex hospitality challenges, reposition underperforming assets, and deliver durable investment performance.

Jared holds an MBA from the University of Colorado, a BS in Mathematics/Economics (summa cum laude) from UCLA, and is a Certified Hotel Asset Manager (CHAM).