Our People

Ryan Gibson is a Founder of Oakdale Capital Management. An entrepreneur and investor with more than twenty years of experience, he has founded, scaled, and invested in businesses across healthcare, technology, real estate, and business services, bringing an owner's mindset and a long-term perspective to every partnership.

Prior to Oakdale, Ryan founded and helped build several successful businesses, including SimpleBills and Cornerstone Caregiving. His experience across multiple industries and market cycles underpins Oakdale's emphasis on thoughtful stewardship, disciplined decision-making, and enduring relationships.

Ryan is a graduate of Baylor University and currently resides in Waco with his wife and six children.

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Michael Hillman is a Founder of Oakdale Capital Management. With more than two decades of experience leading and growing businesses, Michael brings deep operational expertise and a disciplined approach to building enduring organizations. His background managing complex businesses has shaped Oakdale's focus on thoughtful growth, strong leadership teams, and long-term value creation.

Before founding Oakdale, Michael co-founded Cornerstone Caregiving and previously served as an owner and operator within the Visiting Angels system, where he co-owned and managed fifty locations, including several of the nation's highest-performing agencies. He also co-founded AxisCare, helping establish one of the industry's leading software platforms for home care providers. Michael's experience scaling businesses and developing high-performing teams continues to inform Oakdale's investment philosophy and partnership approach.

Michael holds multiple degrees from Baylor University and resides in Waco, Texas, with his wife and three children.

Brent Wilson is a Founder of Oakdale Capital Management. A lifelong entrepreneur, Brent has spent his career building businesses that solve meaningful problems and create lasting value. His experience founding, scaling, and operating companies gives him a practical perspective on the challenges founders face and the partnerships they value most.

Prior to founding Oakdale, Brent was an owner and operator within the Visiting Angels network, where he helped grow one of the nation's largest home care franchise organizations. He also co-founded AxisCare, a leading software platform serving the home care industry, helping transform how care providers manage and scale their operations. Brent's entrepreneurial background shapes Oakdale's commitment to partnering with exceptional management teams, investing patiently, and supporting businesses through every stage of growth.

Brent holds multiple degrees from Baylor University and resides in Waco, Texas, with his wife and three children.

Nate Robertson is the Chief Investment Officer of Oakdale Capital Management. An investor and trusted advisor with more than 16 years of experience, he has spent his career partnering with entrepreneurs, management teams, and business owners to navigate strategic decisions, allocate capital, and create lasting value.

Before founding Oakdale, Nate advised clients on mergers, acquisitions, and corporate strategy across a diverse range of industries at Harris Williams, developing a deep appreciation for the importance of alignment, disciplined thinking, and enduring relationships. His experience working alongside founders and operators continues to shape Oakdale's emphasis on disciplined decision-making, aligned partnerships, and creating enduring value. 

Nate holds degrees from Duke University and the University of Georgia and currently resides in Waco with his wife and three children.