Lindsay Shappee, co-owner of Family Friend Roofing & Construction, shares her journey from a nearly two-decade career in banking, most recently at JP Morgan, to entrepreneurship in Williamson County. In Episode 83 of the Rock Solid: Round Rock Business Leaders Podcast, hosted by Bryan Eisenberg, Shappee details the personal and professional factors that led to her decision to leave Wall Street for rooftops.
Shappee's story resonates amid a broader trend of corporate professionals reassessing their careers and priorities. She describes a pivotal moment during a corporate sales meeting where leadership emphasized a "family-first" culture while she was privately coping with her aunt's terminal illness. This dissonance, she explains, left her feeling isolated and questioning her reputation. Reflecting on the weekend she decided to take leave, Shappee shares: "When I thought I felt so alone, and I thought I had hit rock bottom, there were some really unhealthy thoughts that were going in my head... The more time I spent by myself in my own space, trusting the very inner voice, it just said, 'This no longer serves you.'"
The transition began with a breakfast meeting with Aaron Bernard, who initially sought her consulting expertise but instead offered her an operating role in roofing and construction. Shappee and three partners bootstrapped the company, emphasizing intentional growth over rapid scaling. She also discusses the impact of technology and AI on the banking industry, predicting significant changes in the next five to ten years that are reshaping in-person relationships.
Community involvement is central to Family Friend Roofing's philosophy. Shappee highlights early investments with the Round Rock Chamber and the Five Point Board of Realtors. A notable partnership with Matt Maples of USA Cares resulted in a Christmas roof installation for a veteran, coordinated alongside Will Williams and a donated power wheelchair. Shappee also serves on the executive committee of the Ascension Seton Williamson Foundation and the Chaparral Women's Club advisory board.
Her career shift is rooted in a family legacy of caregiving and entrepreneurship. Her grandmother was a nurse at Ben Taub Hospital, her aunt launched a home healthcare venture, and her biological father built a custom home business from a butcher's toolbox. These influences shape Family Friend Roofing's operating philosophy: bootstrapped growth, intentional hiring, and mandatory community involvement for each project manager.
Shappee also previews the upcoming Women of Wilco luncheon with the Round Rock Chamber, describing it as an event that can change careers. The episode offers insights into the emotional cost of corporate burnout and the value of community-focused entrepreneurship.
