Blake Dailey

Blake Dailey is an Air Force veteran and has bought, renovated, and managed a $20M+ portfolio of 8 Boutique Hotels across Lake Tahoe, Panama City Beach, the TN Smoky Mountains, and the GA Blue Ridge Mountains. He oversaw the construction management of upwards of $10M in renovations on the projects.

Blake also owns and manages Tremont Lodge & Resort, his 130 unit Hotel and resort where Boutique Hotel Con will be hosted. Blake will be speaking on the art of finding hotel deals, as well as scaling hotel operations and management.

Ben Wolff

Ben Wolff is a hotel developer, operator, and marketer building the next generation of outdoor, wellness, and experiential hospitality brands. He co-founded Onera, a nature-immersive landscape hotel brand behind two of the top-performing properties in the Texas Hill Country, and is developing Baya, a farm and wellness hotel brand set to open its first location in Miami in 2027.

Ben also leads Oasi, a hospitality growth and marketing firm that helps independent hotels increase demand, direct bookings, and profitability through strategic marketing and revenue management. He shares these proven growth strategies with hotel owners through the Modern Hospitality Accelerator, a coaching program focused on building stronger brands and long-term pricing power.

Kyle Fugatt

Kyle Fugatt is a former electrical engineer turned real estate entrepreneur, co-founder of Cherokee Rose Homes and The Mallard Hotel, boutique hospitality brands nestled in the Blue Ridge Mountains of Georgia. Since launching his first short-term rental in August 2021, Kyle has scaled to managing more than 100 units—including three boutique hotels—alongside a team of over a dozen professionals.

Kyle specializes in creative finance, boutique hotel operations, portfolio growth, and streamlining systems to create exceptional guest experiences. His hands-on leadership and problem-solving mindset have made him a go-to resource for hospitality owners looking to scale their businesses while maintaining a personal touch.

Diana Ossa & Josh Dobken

Diana and Josh are architects, real estate investors, and boutique hotel operators who combine design-forward thinking with investment strategy. With over 15 years of experience in architecture, construction management, and operations, they’ve built a portfolio of 30+ furnished rentals and boutique hotels. Their flagship property, Terra Palm Springs, has earned international acclaim—including features in Forbes, Vogue, and Travel + Leisure’s 2025 It List. Diana and Josh will be speaking on design-driven development and how to maximize returns through strategic renovations and guest experience.

Steph Weber

Steph Weber, a branding and marketing powerhouse, STR and micro resort investor, Host of the Branded & Booked Podcast, and STR co-host. She is the CEO of The Weber Co where she’s helped over 100 small businesses scale to 6 and 7 figure brands and now focuses on hospitality. Together with 3 other couples, they are building Cabins on the Cumberland, a micro resort and event venue. She and her husband also built a 6-figure co-hosting company in just one year. With 10 years of experience working as a brand and marketing strategist, Steph brings new energy to the world of short term rentals and boutique hotels, helping investors and guests experience destination properties with rave-worth experiences. Steph lives in Indianapolis with her husband, Collin, and two boys. Together, they spend as much time outside as possible, camping, hiking, and exploring.

Tony Stancato

Tony Stancato co-hosts the Michigan Short Term Rentals Podcast (nearly 200 episodes) and the annual Michigan STR Conference, sharing the real trajectory of scaling a hospitality business. He started in single family vacation rentals and moved upstream into boutique hotels, where he and longtime friends acquire and reposition underperforming properties. They founded Book N Gather to manage the portfolio.

Jan Freitag 

Mr. Jan D. Freitag is the National Director, Hospitality Analytics, for the CoStar Group (NASDAQ: CSGP).

In his role, Mr. Freitag comments on the trends that shape the U.S. hotel industry. He is a sought-after public speaker and is frequently quoted in trade publications and the general news media such as The Wall Street Journal, New York Times, Associated Press, Bloomberg, Forbes, etc. He is a trusted source of timely insights for investors, owners, and operators.

Mr. Freitag is a member of the American Hotel Lodging Association Investment Roundtable and the Hotel Development Council of the Urban Land Institute.

He holds a bachelor’s degree, with distinction, from the School of Hotel Administration, Cornell University, and received his Executive MBA, with honors, from Vanderbilt University.

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