In this episode of The Art of Succession podcast, host Barrett Young interviews David Forster, a serial entrepreneur who successfully built and sold three companies ranging from landscaping services to a retail bike shop. Listeners gain valuable insights into how relationship-focused leadership, proper systems, and life transitions drive successful business exits and career pivots.
From The Farm to First Business Exit
David's entrepreneurial journey began with his farm upbringing, leading him naturally into the landscape industry. His first real business was a landscape maintenance and design company started in his early twenties to provide for his new family. Despite having no formal exit strategy, David built the company through exceptional work ethic and a relational approach, treating employees and customers as equals. After four successful years, an unexpected dream led to selling the business to a local competitor who valued their unique customer relationship approach and company culture over just the contract base.
Learning and Growing Through Multiple Ventures
After working for someone else and maturing personally, David started a second landscape company focused on residential design and build projects. This venture taught him to price properly, think systematically, and build intentional processes from the start. The business grew to similar team size but double the revenue of his first company. Around the four-year mark, feeling burned out, David discovered cycling during a week off and realized he wanted to share that stress-relief experience with other business owners, leading him to open a bike shop.
The Bike Shop Years and Life-Changing Events
David ran his bike shop for over seven years, learning retail operations, inventory management, and building community around cycling. However, his world changed dramatically when he became a father at 40 after discovering he and his wife had the MTHFR gene mutation affecting fertility. Tragedy struck when his wife's sister died unexpectedly two weeks after their daughter was born, followed by David's father's death nine months later. These profound losses forced David to reevaluate priorities, recognizing that retail hours weren't compatible with being the father and husband he wanted to be.
Transition to Fractional COO
David sold the bike shop to another dealer and eventually embraced fractional COO work after initially resisting the idea. His approach typically begins with a 6-12 week deep dive to establish core systems, followed by either training internal team members or providing ongoing part-time support. David focuses on overcoming team resistance by addressing consultant skepticism upfront, emphasizing he's there to make lives better through systems that create freedom rather than restrictions. His philosophy centers on checklists and processes that allow both new employees to learn and experienced ones to maintain focus when interrupted.
Listeners can learn more about David Forster by connecting with him on LinkedIn or on his site www.systemsoversweat.com, where he offers templates for role descriptions and system clarity tools.
