Jon Oksenholt – Chairman, CEO & Founder
Jon Oksenholt is the Chairman, CEO, and Co-Founder of Oksenholt Capital and its affiliated companies. In total, the “Oksenholt Companies,” which are primarily majority-owned and founded or co-founded by Mr. Oksenholt, have over $1.3 billion in assets under management (as of June 1, 2024), 500+ employees, 25 offices, and generate over $80 million in gross revenue. Mr. Oksenholt has established businesses across various asset classes, including hospitality, where one of our lodging brands has been consistently recognized as a fast-growing Owner-First company, including by Skift in 2023, where it was listed as a top 10 North American Vacation Rental Manager; real estate, where Mr. Oksenholt started his investment career with a $10,000 investment and has since built a vertically integrated group of real estate companies; technology companies, which include digital media and marketing, global staffing, business consulting, e-commerce, and native retail. Mr. Oksenholt also owns businesses in development, property management, and asset management, which are primarily dedicated to the infrastructure necessary for a fully integrated family of real estate companies.
Mr. Oksenholt is also an avid philanthropist with a history of supporting children and education and believes in giving back 10% as tithe each year. He is deeply committed to continuing to build his companies on the principles of meritocracy, excellence, solutions, integrity, and innovation. Mr. Oksenholt also believes that experience is overrated and has often been known to promote promising individuals to senior leadership positions and has been known to hire people in unusual ways including people he has met while dining out.
Mr. Oksenholt holds a B.A. from Walla Walla University and a J.D. from the University of Washington.
EJ – Investment Partner, Oksenholt Capital Group
As Investment Partner, EJ Oksenholt collaborates with bankers, attorneys, contractors, and property management professionals to source, structure, and oversee diverse real estate investments. With experience spanning acquisition analysis, deal structuring, and project execution, he ensures each venture is strategically positioned for long-term value and strong returns. His entrepreneurial approach is complemented by meticulous attention to detail and a commitment to building lasting partnerships. Beyond his work in real estate, EJ is an avid collector of fine timepieces, reflecting an appreciation for precision, craftsmanship, and enduring quality.
Atharva – Co-Founder, Flow
Atharva drives the company’s strategic direction, product development, and client success initiatives. With a background spanning technology, marketing, and business analytics, he combines data-driven decision-making with creative problem-solving to deliver high-performance websites, marketing solutions, and technology platforms for the vacation rental industry. Atharva works closely with clients to design and implement systems that optimize revenue, enhance user experience, and strengthen market position. His leadership reflects a blend of entrepreneurial vision, operational discipline, and a commitment to measurable results.
John – COO
John brings deep operating and investment experience across multiple industries, with a proven track record of scaling vacation rental management platforms. Most recently, he spent four years as an executive at a private equity-backed company, where he served as a key leader and deal partner in growing the business from its first acquisition into one of the largest vacation rental management companies in the United States, overseeing nearly 6,000 homes. In this role, John helped build the company’s core operating platform, led acquisition integrations, and managed a portfolio of local brands—establishing the foundation for scalable, sustainable growth.
John’s leadership approach centers on investing in people: coaching and developing talent, creating opportunities for growth, and empowering teams to take ownership and perform at a high level.
Prior to entering hospitality, John held roles across strategy, business development, and finance, giving him a broad and balanced perspective on operational execution and long-term value creation. He is excited to bring this experience to our hospitality portfolio and support the continued growth of its diverse platforms and collection of brands across Food & Beverage, Health & Wellness, and Lodging.
Bob – Head of Hospitality
Bob brings over thirty years of executive experience in restaurant and hospitality operations, leading teams and managing performance across some of the industry’s most recognized brands. His career includes senior leadership roles with McDonald’s, Burger King, and Dunkin’, where he established a strong record of operational excellence, financial growth, and team development. Bob specializes in optimizing systems, driving process improvement, and fostering a culture of accountability and engagement. His leadership reflects a balance of strategic insight, operational discipline, and a commitment to delivering exceptional guest experiences and measurable business results.
Bobby – National Director of Sales
Bobby brings more than twenty years of experience in the vacation rental management industry, combining a deep passion for hospitality with strong operational and commercial leadership. He began his career in short-term rentals as General Manager of Myrtle Beach Vacation Rentals, Inc. in South Carolina’s Grand Strand, where he developed a strong foundation in both guest experience and business performance.
He later joined TurnKey Vacation Rentals, where he helped launch the company’s expansion into Nashville, TN—scaling the market by hundreds of properties and contributing to TurnKey’s growth into one of the fastest-growing vacation rental management companies in North America. From there, Bobby went on to lead the largest vacation rental sales team in North America as National Sales Director at Vacasa. Throughout his career, he has also served as a trusted deal partner, supporting growth through strategic relationships, market expansion, and execution.
Across both high-growth startups and major industry leaders, Bobby’s leadership style has remained consistent: lead with a smile, support the team, and strive for excellence together. At the core of his work is a genuine commitment to helping others—whether guiding property owners or connecting families with the perfect vacation experience. He looks forward to partnering with the talented teams at hospitality division and supporting continued growth across the company’s diverse portfolio.