From Wall Street to Rooftops: Lindsay Shappee's Bold Career Shift

Frequently Asked Questions

Why did Lindsay Shappee leave JP Morgan to start a roofing company?

Shappee describes reaching a crossroads after a corporate sales meeting where leadership preached a 'family first' culture while she was privately navigating her aunt's terminal illness, a moment that left her feeling isolated and questioning her reputation. A breakfast meeting intended as consulting turned into an operating role with partner Aaron Bernard, and the multifaceted opportunity aligned with her values around community and interpersonal relationships.

What is Family Friend Roofing & Construction's approach to growth?

The company is bootstrapped with no outside financing and has intentionally declined opportunities to scale quickly. Shappee emphasizes hiring for cultural fit over rapid expansion, arguing that scaling only for profit is 'a recipe for crash and burn.' Every project manager is required to participate in community involvement, whether networking with realtors, insurance agents, and lenders, or giving back through service.

How is the company giving back to veterans?

Family Friend Roofing partnered with Matt Maples of USA Cares to donate a Christmas roof to a veteran. That same veteran, Rico, also received a donated power wheelchair coordinated with Will Williams, a previous Rock Solid guest. Shappee describes watching Rico regain mobility as one of the most memorable moments of her entrepreneurial journey.

Who influenced Shappee's entrepreneurial mindset?

Her biological father went from working as a butcher with a toolbox in his truck to designing and building custom homes, and Shappee's first job was sanding and priming plantation shutters. Her grandmother nursed at Ben Taub Hospital, and her aunt, a lifelong nurse, launched a home healthcare venture in the Houston area with her husband, shaping Shappee's people-first business philosophy.

Why does Shappee believe in-person banking is changing?

Shappee argues that AI and technology have advanced exponentially over the last ten years, absorbing many functions of traditional banking roles. She predicts that within five to ten years there may not be as many in-person bankers, which reinforced her decision to pivot into a relationship-driven trade like roofing where face-to-face service still matters.

Why does Shappee recommend attending the Women of Wilco luncheon?

Shappee tells listeners that early entrepreneurs, nonprofit fundraisers, or anyone seeking more involvement should expect to make at least ten new connections at the luncheon. She emphasizes that Williamson County women will give their time for coffees, lunches, and Zoom calls, and that a single conversation in that room has the potential to change a career trajectory.