For many family-owned businesses, succession planning is something that gets pushed aside until circumstances force it into focus. For Flake & Co., that turning point became the catalyst for building something new.
After a serious health event in 2019, John Flake began thinking more intentionally about the future of the business and the importance of creating a path forward for the next generation. His daughter, Jessica Flake Dearnley, already had extensive experience in commercial real estate and a strong financial background, but the structure in place at the time did not allow for a transition into ownership.
Rather than forcing a fit within an outdated framework, John and Jessica made the decision in 2020 to launch a new chapter under a familiar name: Flake & Co. The name itself carries legacy, but the company was built as a true startup — one created intentionally, from the ground up, with a long-term vision for growth.
That distinction matters. Flake & Co. was not inherited as a finished operation with systems, staff, and structure already in place. It was built through experience, leadership, and a willingness to create a business designed for the future rather than relying on the past.
The story reflects a broader truth for closely held businesses: successful succession does not happen by accident. It requires planning, the right people, honest evaluation, and a structure that supports both continuity and growth. When those pieces are missing, even strong businesses can struggle to make the transition smoothly.
For Flake & Co., the result was not simply a leadership handoff. It was the creation of a company positioned to grow with purpose, rooted in experience but built for a new generation.
