Letting Go to Grow: An Entrepreneur’s Leadership Evolution

Join Aaron Burnett as he sits down with Kara, founder of Pepper’s Personal Assistant, to explore what it truly means to design a business that supports your life — not the other way around.What began as a creative solution during her son’s half-day kindergarten has grown into a 25-person team serving busy executives across Seattle. Along the way, Kara evolved from accidental entrepreneur to confident leader, implementing EOS, building a trusted leadership team, and stepping fully out of the day-to-day.Today, she runs her company while traveling the world — living proof that entrepreneurship can create both impact and freedom.In this conversation, you will hear about scaling a service business, building one-to-one trust with clients, leading W2 employees with intention, and how EO Accelerator and EO helped shape her journey. This episode is about growth — in business and beyond.About EO Seattle:Entrepreneurs’ Organization is a global community of 20,000+ entrepreneurs across 220 chapters in 61 countries. EO helps business owners connect, learn, and grow through shared experiences that support their business, family, community, and personal journeys.This podcast features real entrepreneurs sharing real challenges and solutions.No pitches, no sales—just honest conversations about the moments that shape successful businesses.