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Kyle is a serial entrepreneur with over three decades of experience building, operating, and advising technology-driven businesses. He is a Fractional Chief Technology Officer (fCTO) and Operational Maturity Consultant known for his ability to bridge business strategy, technology, and security to drive scalable growth and operational clarity.
For 29 years, Kyle owned and operated a Managed Services and technology consulting business, working closely with business owners and executive teams to modernize infrastructure, protect intellectual property, and turn technology into a strategic, process driven advantage—not just an expense. That experience led to the development of a value-add Technology Package for multifamily properties that creates new revenue streams, supports revenue-sharing models, and measurably increases asset value.
Kyle comes from an extraordinary military family. He is the youngest of thirteen, with a father who served in World War II and the Korean War, and seven siblings—along with Kyle himself—who served in the U.S. Armed Forces. Kyle spent nine years in the U.S. Army as an Information Systems Security Officer, where he developed deep expertise in cybersecurity, risk management, and mission-critical systems.
Following his military service, Kyle was recruited by the Department of Energy to work at Los Alamos National Laboratory, where he served as a security engineer and was frequently called upon to solve complex, high-stakes technical & national security challenges.
Today, Kyle applies that operational, security, and technology background to commercial real estate investing, where he focuses on broker relationships, capital raising, and integrating technology as a force multiplier for asset performance through Wentworth Holding Group.
Our Team
Josie Wentworth is Co-Founder and Managing Partner of Wentworth Holding Group and manages acquisitions, investor relations, and marketing.
Prior to Wentworth Holding Group, Josie served as a Manufacturing Engineer for Applied Materials in Austin, TX as well as a Product Marketing Engineer for NEC Electronics DRAM division in Santa Clara, CA. Once children arrived, it was decided that one should be home to raise children, the most important job on the planet! During the decade-long adventure of child-raising, Josie's passion for learning and education led to the decision to Classically homeschool for a season and later accept a lead teaching role on the faculty of Founders Classical Academy.
After several years of teaching, Josie used her knowledge of educational methods and design theory to transition to a corporate environment as a Senior Instructional Systems Designer for a government entity. In this role, she establishes project management processes, designs mobile applications and virtual instructor-led training products, employs instructional technologies such as Learning Management platforms, and authoring tools to deliver high quality, cost-saving products for stakeholders.
Josie is a limited partner in 292 multifamily units in Oklahoma and South Carolina, as well as general partner in 203 senior living units in Texas and Florida. She is involved with the WHG acquisition process, including identifying profitable properties by underwriting and conducting financial analysis to assess potential returns, risks, and market conditions. Additionally, she is actively engaged with investor relations, providing regular updates, and ensuring compliance with legal and financial obligations essential for fostering trust and ensuring the success of investments, delivering optimal results for investors.
Eric Upchurch
Advisor
Eric Upchurch is an Army Special Operations veteran who has a passion for educating the military community on how to create long term wealth through real estate investing. Eric has been a General Partner in 4,809 units and a Limited Partner in 4,621 units, co-authored a bestselling book titled Military House Hacking, is an accredited investor, and has been involved in over $165M in multifamily and storage assets. He has been involved in sourcing, capital raising, risk capital, asset management, investor relations and served as a Key Principal.
While serving our nation, Eric completed 5 combat deployments, and earned a Master’s Degree in Aeronautical Science all while managing a 27-man squad, deployed around the globe. Eric now serves as Co-Founder of Active Duty Passive Income (ADPI) and as Chair of National Fundraising for non-profit, Veterans Community Project.
Eric resides in California with his wife of 19 years and two boys.
Rod Khleif is an entrepreneur, real estate investor, multiple business owner, author, mentor, and community philanthropist who is passionate about business, life, success, and giving back. As one of the country’s top real estate trainers, Rod has personally owned and managed over 2,000 properties.
As an accomplished entrepreneur, Rod has built several successful multi-million dollar businesses. As a community philanthropist, Rod founded and directs The Tiny Hands Foundation, which has benefited more than 100,000 community children and families in need. Rod has combined his passion for real estate investing and business development coaching with his personal philosophy of goal setting, envisioning, and manifesting success to become one of America’s top real estate investment and business development trainers.
Any potential investors should not construe Rod Khleif listed as a “senior advisor” to mean Rod Khleif or his team have analyzed or endorsed any particular investment opportunity.
Rod Khleif
Senior Advisor