David Smith

Founder & Managing Principal

David Smith is an experienced hospitality industry investment professional and investment banker, and a recognized supporter of the growing outdoor accommodation industry. As an advisor and principal, he has structured over $1.5 billion of hospitality real estate transactions, including several of the largest equity and debt financings in the outdoor sector.

Prior to establishing Outside Capital, David was a Senior Director at Whitman Peterson, a Los Angeles-based real estate private equity firm and a leading investor in traditional and alternative hospitality strategies. David was previously a Senior Director at RobertDouglas, where he represented prominent ownership groups, brands, and management platforms in North America, Europe, Asia, and Australia in the structuring of hotel real estate and M&A transactions. Prior to joining RobertDouglas, he worked as a credit analyst at Macquarie Group in New York City.

David is a graduate of the Master of Management in Hospitality (Real Estate) degree at Cornell University and earned his undergraduate degree from the University of Sydney in Sydney, Australia. He has also studied at the Hong Kong University of Science and Technology. He is a member of the Cornell Hotel Society, the Urban Land Institute, and serves as an advisory board member of the American Glamping Association and Saira Hospitality.

JamieRose Briones

CHIEF DEVELOPMENT OFFICER

JamieRose is a multi-disciplinary executive and an experienced development consultant focused on experiential hospitality destinations. As a specialist who is passionate about developing and enhancing outdoor hospitality offerings, she has advised companies like Four Seasons, Belmond, Marriott's Tribute Portfolio, Sagra, Vulcan Inc, and the Investment Corporation of Dubai.

Prior to joining Outside Capital, JamieRose was a Principal and the Executive Director of Strategic Advisory at Luxury Frontiers, leading a team of adventure tourism experts who help clients navigate the development of new products in the outdoor sector and define distinguished hospitality experiences for their guests. As a brand builder, JamieRose was also responsible for growing the Luxury Frontiers brand itself, heading the award-winning firm’s marketing and PR efforts. 

Originally in finance working at Citi in New York City, she strategically transitioned to outdoor hospitality via graduate school and lodge operations. JamieRose served as General Manager of Abu Camp in Botswana’s Okavango Delta to attain a comprehensive knowledge of low-volume, environmentally low-impact yet high-revenue adventure lodging operations. While in Africa, JamieRose also served as a Service Coordinator for Wilderness Safaris—defining, auditing, and enforcing the standards for the service, branding, and training for various 3-, 4-, and 5-star camps throughout Botswana, Zambia, and Namibia.   

JamieRose earned the Executive MBA in Hospitality Administration degree from Ecole hôtelière de Lausanne and her Bachelor’s degree in Business Administration with concentrations in Finance and International Business from New York University's Stern School of Business. Having lived on 4 continents, she has also completed site inspections of 120+ luxury and lifestyle properties across 20+ countries, building a wide and deep understanding of the modern hospitality landscape and guest profile.

Doug hercher

Principal & Managing Director, RobertDouglas

Doug Hercher is a Founding Principal at RobertDouglas and has over 30 years of investment banking and capital markets experience in the hospitality and real estate sectors. He has held senior leadership positions at JLL, Lehman Brothers, Sonnenblick Goldman and Cushman & Wakefield, where he was responsible for more than $50B of transactions throughout North America, Europe and the Caribbean. Doug has written for and contributed to articles in publications such as the Wall Street Journal, New York Times, Hotel Business, Bloomberg and Real Estate Forum, as well as speaking at the Federal Reserve Bank and numerous other industry conferences. A graduate of Colgate University and the Columbia University Graduate School of Business, Doug is a resident of Brooklyn, NY and an enthusiastic traveler and outdoorsman.

ruben Martinez

Co-Founder, Glamping Hub; Founder, The American Glamping Association

Ruben Martinez is the Co-Founder of GlampingHub and the American Glamping Association. Glamping Hub is the largest transactional glamping booking platform with properties listed worldwide.

GlampingHub now offers over 35,000 listings with offices in Denver and Seville, Spain. Ruben completed both his undergraduate degree and his MBA with a focus in International Business at Regis University. He is an affiliate faculty member at Regis University teaching Innovation and Entrepreneurship in the MBA program. Ruben lives in Colorado with his wife and two daughters.

Barry Olson

Former Managing Director, Goldman Sachs

Barry Olson was most recently a Managing Director in the Real Estate Principal Investing Group of the Merchant Banking Division, before retiring from the firm after a 24-year tenure. He and his teams were responsible for sourcing, underwriting and structuring commercial real estate debt and equity investments. Barry was instrumental in starting and heading or co-heading several debt platforms within Goldman Sachs which were responsible for the origination of investments in commercial real estate projects totaling over $80 billion in total capitalization. He also served as a voting member on the Real Estate Investment Committee. Previously, Barry worked in Commercial Real Estate lending at Bank of America and headed the Real Estate Syndications and Mezzanine Debt platform for JP Morgan Chase in Texas. He received a BBA from the University of Wisconsin and an MBA from Southern Methodist University. Barry is a member of the Urban Land Institute (past chair of a product council) and has served as Board Member and Chairman of the Giving Gala of the Dallas Real Estate Council.

Kevin osterhaus

President, Graduate Hotels

Based in Nashville, Kevin Osterhaus is the President of Graduate Hotels, where he oversees global operations and marketing of the brand’s collection 35 U.S.- and U.K.-based properties. Kevin was most recently Chief Operating Officer for Ennismore International, overseeing global operations for The Hoxton brand of lifestyle hotels. Kevin’s leadership experience in lifestyle and boutique hotel operations also includes prior roles as President for SIXTY Hotels and Executive Vice President of Operations for Standard International. He previously spent over a decade with innovative brands in luxury destination travel, including Destination Club Management and ClubCorp where, among his leadership posts, he served as Managing Director for Miami Beach’s famed The Villa Casa Casuarina.

Bernie siegel

Former Partner, KSL Capital Partners

Bernie Siegel is a former partner at KSL Capital Partners, a leading investment firm in the travel and leisure businesses with deep experience in hotels and resorts, clubs, skiing, and resort real estate. During his extensive career in the hospitality industry, he was also served as Executive Vice President of Lowe Hospitality Group, and as chief investment officer of its wholly-owned subsidiary Destination Hotels & Resorts. Bernie previously was Managing Director Hospitality Division of Secured Capital Corp, and also held real estate positions at Marriott Corporation and Pannell Kerr Forster. Bernie is an active member of Urban Land Institute and Cornell Society of Hotelmen. He holds an M.B.A. from the University of Colorado and a B.A. from Cornell University's School of Hotel Administration.

Rob stiles

Principal & Managing Director, RobertDouglas

Rob Stiles is a Founding Principal at RobertDouglas, with more than 25 years of domestic and international experience in the hotel and travel industries. At RobertDouglas, Rob co-leads the firm’s outdoor hospitality investment banking activities, and has structured & raised nearly $500 million of growth capital for leading brands including Autocamp, Collective Retreats, and numerous other start-up platforms. Rob serves on the International Advisory Board of HOTELS Investment Outlook magazine, is the founder of HICAP, Asia’s premier hotel investment conference based in Hong Kong. He has a Bachelor of Science degree with a focus in development and finance from Cornell University’s School of Hotel Administration.