About Legacy Vacation Holdings

Building Enterprise Value through World Class Teams

Legacy Vacation Holdings is a leading firm specializing in the acquisition of vacation home & resort services management companies. Our experienced team is dedicated to delivering exceptional results and maximizing your investments. Choose us for unmatched growth and profitability, ensuring a secure legacy for years to come. Start your path to success with Legacy Vacation Holdings.

Who We Are: Over 50 Years of Combined Partner Experience

Kyle Killian, Managing Partner

Kyle Killian is an experienced Managing Partner and Founder with a successful track record of building and leading high-performing teams in various sectors, including mid-market, non-profit, and Fortune 500 global companies.

Previously, he served as Chief Operating Officer of ThirdHome, the world's largest luxury home exchange and travel platform. Under his leadership, he implemented a robust strategy to reverse consistent financial losses and achieved the company's first profitable growth period. He was also part of the executive team at Fanatics during their rapid growth phase, which led the business to exceed $1 billion in revenue and experience a successful exit event. Additionally, he worked on successful projects with private equity portfolio companies, including Staywell, Provata, and Edgenet.

With over 20 years of experience in executive leadership, Kyle has effectively collaborated with private equity-backed, family investments, and publicly traded firms, helping them build key leadership teams for growth, success, and profitable exits or liquidity events.

Kyle's background includes serving as a Former Intelligence Officer in the US Navy with multiple tours in Iraq, as well as being an Ironman Finisher. He earned his undergraduate degree from the University of Houston and completed post-graduate studies at the Naval War College and UCLA Anderson School of Business. He is a life member of the Veterans of Foreign Wars, Military Officer's Association of America, and Association of Former Intelligence Officers.

Currently residing in the Nashville, TN area with his family, Kyle brings a wealth of expertise and strategic insight to Legacy Vacation Holdings.

Chad Rowe, Strategic Advisor

Chad Rowe is an industry leader who brings to the table 20+ years of luxury resort real estate sales, mergers and acquisitions, property management, short-term vacation rental operations, and global home exchange experience. He holds Principal Brokers Licenses in VA, GA, NC, CO, NM, as well as representation in the Turks and Caicos Islands.

Chad previously resided as Senior Vice President of Business Development at THIRDHOME, the worlds largest luxury home exchange & travel platform.

Before joining THIRDHOME, Chad served as Senior Vice president of Business Development and Principal Real Estate Broker for Natural Retreats US LLC, a top national player in the luxury vacation rental management industry. He was responsible for brokerage oversight over their national Vacation Rental, Property Management, and Real Estate interests and leading resort destination growth via Mergers and Acquisitions. During his tenure, Chad successfully acquired and onboarded seventeen (17) STR Companies around the US, encompassing over $150,000,000 in annual revenue.

Prior to launching Natural Retreats in 2010, he held the position of Director of Real Estate for Celebration Associates, overseeing the real estate development sales and marketing for best-of-class resort development projects throughout the Mid-Atlantic and South-Eastern regions. In doing so, his primary focus was pre-construction land and custom home sales.

Chad began his real estate career in 2000 when with Intrawest Corporation. While there, Chad aided in launching its real estate sales and marketing division, Playground Destination Properties. His experience spanned multiple products, lifestyle, and experience offerings across the United States, Canada, UK, Caribbean, and British West Indies.

He earned his BA in English from Randolph Macon College in Ashland, VA, where he now holds a seat on the Board of Advisors. He proudly resides in both Charlottesville, VA, and Eagle Ranch, CO, with his wife Katie and daughters Hayden and Abigail.

Advisory Board Members

Jeannie Shroads

Jeannie Shroads is a licensed attorney with 20+ years of experience in senior in-house counsel roles at a global non-profit membership association and a national vacation rental company. She is licensed to practice in Virginia and Idaho. As a chief legal officer, she managed all aspects of legal matters which included governance, litigation and contract work.

Jeannie also provides consulting and training services for peacebuilding, humanitarian, and development organizations. She received her master’s degree in Conflict Analysis and Resolution from the Jimmy and Rosalynn Carter School for Peace and Conflict Resolution at George Mason University with a specialty in Conflict-Sensitive Development and Resilience. She was the principal contract researcher of a report on Best Practices for Conflict Sensitivity in Peacebuilding commissioned by the Alliance for Peacebuilding and USAID, America’s international development agency.

Jeannie and her husband John moved to the Wood River Valley of Idaho in 2021 and is active in local nonprofits including serving as President of the Board of the Wood River Women’s Foundation.

James S. “Jim” Olin

Jim Olin has been a leader in the hospitality, resort real estate and development industries since the 1980’s. Jim is currently CEO of C2G Advisors LLC, a strategic consulting firm specializing in all facets of the hospitality industry, with special emphasis on short-term rentals and resort activities. The company also has a robust M&A operation, and has been responsible for more M&A deals within the vacation rental industry than anyone else in history. Olin was also part of a select negotiations team for one of the largest class action settlements in the history of the United States, and Jim continues to provide litigation consulting in the areas of hospitality and business economic loss. Cases range from being a corporate representative for real estate developers to slip-fall and other liability cases within the hospitality industry.

Previously, Jim was Managing Partner of The Sterling Companies LLC. He managed the merger of three of Northwest Florida’s leading privately owned resort development, resort management and real estate sales companies into one powerful regional company servicing all facets of the resort industry. Until September 2008, the company managed over 1500 rental units, employed over 50 real estate agents, and had developed high-rise condominium projects throughout Destin and Panama City Beach, Florida..

Jim is the former President and CEO of ResortQuest International (NYSE: RZT), the world’s largest vacation rental property management and resort real estate firm. Under his leadership at ResortQuest, Olin guided the network of more than 20,000 vacation rental and hotel properties in 52 premier resort destinations and developed alliances and partnerships that gave ResortQuest a truly global reach. ResortQuest had more than 5,000 employees and managed a vacation rental portfolio valued at over $7 billion. Olin also oversaw a real estate brokerage network of more than 350 agents, who traditionally managed in excess of $1 billion in real estate listings.

Olin had been with ResortQuest and its subsidiaries for ten years. He was appointed COO of the company in January 2000 and was then promoted to President in April 2002. Previously, he was President and CEO of Abbott Resorts and Abbott Realty, based in Destin. As President and CEO of Abbott Resorts from 1992 until January 2000, Olin engineered the company’s growth from 900 units to more than 2,500 units, and real estate sales from $35 million to $250 million annually. Olin also spearheaded the development and operations of Henderson Park Inn Bed and Breakfast, Tops’l Beach Resort, and Gulf Place Resort. Prior to joining Abbott Resorts, he served in various capacities within the tourism and economic development fields in Florida, beginning with the Florida Department of Commerce.

Jim is a licensed real estate broker in Florida, Alabama, Mississippi and Tennessee, and has been appointed to numerous State level committees and task forces by previous Florida Governors and Secretaries of Commerce. Jim is a member of both the prestigious Counselors of Real Estate (CRE), and the Council of Real Estate Broker Managers (CRB) – he is one of only 8 persons currently invited to membership in both organizations simultaneously.

Jim also has certifications from the National Association of Realtors as a Resort and Second Home Property Specialist (RSPS), and a Senior Real Estate Specialist (SRES). He is also a Certified Negotiations Expert (CNE), and a Fellow with the Royal Institute of Chartered Surveyors. Jim currently sits on the Board of Directors of Key Data Dashboard, and formerly sat on the Board of Advisors for Host Compliance.

Olin is a former Research and Statistics Instructor at the University of Phoenix, and holds a Masters Degree from Florida State University. He is also a founding Board Member of the Onsite Property Managers Association (OPMA) and is a frequent speaker at the Vacation Rental Managers Association (VRMA) National Conference. Jim has been married for over 40 years to his beautiful wife, June, and they have 4 children and 8 grandchildren.

Sarah Franzen

Sarah Franzen is founder and principal consultant at REVZEN, a boutique revenue management firm specializing in education, full-service revenue management, and data analytics and research for short-term/vacation rental managers. REVZEN advises, educates, and manages revenue portfolios across multiple markets, countries, and product types. REVZENylitics, the data science arm of the business, expands REVZEN's focus outside of the hospitality segment to also include any business seeking to extract insights from their data to help them understand customer behavior, design messaging, predict future trends, and make informed business decisions.

Sarah spent 7 years in hotel revenue management prior to making the transition to short-term/vacation rentals where she was head of Revenue Management (RM) and Analytics for over 8 years at Natural Retreats, a US-based, multi-market property manager. She has spoken on several podcasts, webinars, and conference stages over the years and was honored to have been awarded the inaugural "Revenue Manager of the Year" distinction at the Data and Revenue Management (DARM) Conference in 2021. She also partnered with companies like Transparent (now Lighthouse), AJL Atelier, and Hotel.School (Europe) to design/create and produce educational materials for the short-term rental space.

Sarah is co-founder of RevProf, a new, non-profit community of new and existing revenue professionals in the short-term rental industry which aims to further professionalize the discipline by supporting connection, collaboration, education, standardization, and innovation in our field. She holds bachelor's degrees from the University of Minnesota (B.M., Music and B.S. Business Statistics), and master's degrees from San Jose State University (M.M., Vocal Pedagogy), and the University of Georgia (M.B.A., Marketing).