My guest for Episode #306 of the My Favorite Mistake podcast is Betsy Pepine, a serial entrepreneur in real estate and the founder of Pepine Realty. Betsy leads a top-producing real estate team consistently recognized by The Wall Street Journal and has built a family of companies that includes a property management firm, title company, real estate school, and a nonprofit.

EPISODE PAGE WITH VIDEO, TRANSCRIPT, AND MORE

She’s also the author of the 2024 book Breaking Boxes: Dismantling the Metaphorical Boxes That Bind Us, which explores the limiting labels and roles we assign ourselves—and how to break free from them.

Betsy’s favorite mistake was starting her brokerage with no clear plan. What began as a solo effort out of her home unexpectedly turned into a team, and eventually a company—but without intentional structure or culture. That all came to a head when her trusted assistant resigned right before a long-overdue family vacation. Her assistant’s honest feedback—about the lack of family, growth, and purpose—was a painful but pivotal wake-up call. Betsy responded not by retreating, but by reading leadership books on her cruise, hiring a coach, and reinventing her company with clear values and a defined mission.

In our conversation, Betsy shares how she rebuilt Pepine Realty around core values like family, impact, and growth. She talks about initiatives like creating a nonprofit to address housing affordability and designing career paths that include a rare salaried-agent model in real estate. We also discuss the power of learning from mistakes—including how her team shares “learnings” each week in a psychologically safe environment that accelerates growth and prevents repeated errors.

Betsy’s story is about far more than real estate—it’s about leadership, self-awareness, and responding to failure with action. Her perspective will resonate with anyone building a team or culture where people feel seen, supported, and inspired to improve.