Penny Mendelsohn — known as "Penny the Roofer," the face of Roof Whisperer — is the fourth generation of the Farbstein family to lead a roofing and waterproofing legacy that traces back to her great-grandfather, who helped found the sheet metal roofers' union in New York City in the late 1800s. Raised on rooftops beside her father, David, and armed with a degree in architecture, Penny spent decades proving herself among the men who build and own some of the biggest properties in New York City — growing her father's company from 100 employees to 700. Then it all came apart. A grueling battle with illness nearly took her life, and in the collapse that followed — compounded by COVID-19 — she lost the business, and very nearly herself, while still clinging to who she thought she was supposed to be: the dutiful wife, the successful businesswoman, the daughter who'd conquered every stereotype in a world built by and for men.
Rather than stay down, Penny rebuilt McFar Contracting, a roofing company serving commercial properties across the New York tri-state area, from hospitals to high-rises. She brought her father back to work at her side, along with her nephew Ethan, the fifth generation — and today the three of them run the company as best friends first, spending their days doing the work they love and living in a daily state of gratitude. That gratitude fuels Roof Whisperer, where Penny teaches property owners how to find, fix, and prevent roof leaks, while sharing the harder lesson life taught her: that like a roof over your head, the things that hold you up — your mind, your body, your relationships, your true self — are the ones you take for granted until it's almost too late.
IN THIS EPISODE YOU’LL LEARN:
- How Penny rebuilt McFar Contracting on systems and processes instead of sheer will after losing her father's company.
- Why she teaches building owners to find, fix, and prevent flat roof leaks before costly damage spreads.
- How her simple three-step Find, Fix, Prevent process gives property owners honest answers without upsell pressure.
- Why the Roof Whisperer platform equips homeowners and building owners to understand roofing experts before they hire.
- How Penny scaled her father's company from 100 to 700 employees, then lost it all and still rebuilt.
- Why she prioritizes mentorship, leadership, and culture-building instead of headcount when rebuilding a business.
- How she brought her father and nephew Ethan together to run McFar as a fifth-generation family business.
- Why treating your health, mind, and relationships proactively is like maintaining a roof before it leaks.
- How Penny leads with kindness in a male-dominated commercial roofing industry and still earns respect.
- Why her great-grandfather's sheet metal union legacy shaped four generations of roofing expertise in New York.
about the show
Legacy Makers is an entrepreneur TV series and business documentary experience built around powerful founder stories, leadership lessons, personal branding, and the strategies behind lasting success.
Each episode takes viewers inside the minds of influential entrepreneurs, industry leaders, pro athletes, executives, and business titans to uncover the moments, decisions, challenges, and breakthroughs that shaped their journey.
Through cinematic storytelling and in-depth conversation, Legacy Makers highlights the real experiences behind success, from building a brand and overcoming obstacles to developing expertise, creating impact, and leaving a legacy that reaches beyond business.
