Randy Chalker

Randy Chalker is the founder of Cairnwell Advisors. He brings nearly three decades of experience across business ownership, private equity investing, mergers and acquisitions, finance, and hands-on operating leadership.

Randy has worked with Woodlawn Partners since 2017, where he has been involved in evaluating and executing private-company investments, supporting portfolio businesses, raising capital, and working with business owners through acquisitions and other strategic transactions. He also serves as CEO of a small manufacturing company, giving him direct experience with the everyday realities of running an owner-led business—including operations, financial management, sales, hiring, and long-term planning.

Earlier in his career, Randy worked in fixed-income sales and trading at Goldman Sachs and BNP Paribas and began his career in consulting and investment banking.

Randy founded Cairnwell to bring institutional-quality financial analysis, operating discipline, and transaction experience to smaller businesses that rarely have access to those resources. He works directly with owners to improve performance, make better decisions, prepare for growth or transition, and build more valuable and durable companies.

Randy holds an MBA from the University of Chicago Booth School of Business and a BBA in Finance from the University of Wisconsin–Madison.