Starting a business is hard because it’s a fight with yourself, an internal battle – gaining the courage to get started, etc. Scaling a business is different – the challenges you face are mostly external to yourself. Each challenge has a million mini-challenges. We wanted to create a space for conversations and stories around growth and scaling. Below, you’ll find stories and insights from successful entrepreneurs across a variety of industries and markets.

Stephen Grybowski

When we started The Rock and Roll Playhouse, the goal was simple: to create a space where families could experience live music together, introducing children to the magic of iconic artists like The Beatles, Bob Marley, and the Grateful Dead. What began as a series of small shows at Brooklyn Bowl quickly grew into a national program, but that growth came with its share of twists, challenges, and valuable lessons. Read more>>

Erica Leonhard

Scaling Up Magical Dreamers Travel: From Dreams to Reality

When I founded Magical Dreamers Travel in 2021 with my business partner, I knew our journey would be full of challenges but also brimming with possibilities. My story is not just about an agency that grew exponentially; it’s about a woman who decided to bet everything to fulfill her dreams. Read more>>

Caitlin Lang

The insight that transformed my business was simple, but ended up being incredibly powerful: busy women running service-based businesses need a better way to get their branding done. Like most designers, I started with a traditional approach that required constant client involvement—providing content piecemeal, reviewing multiple design iterations over weeks or months, and maintaining endless email threads. This process wasn’t just limiting my ability to scale; it was actively preventing my clients from focusing on what they do best: running their businesses. Read more>>

Morgan Bender

My photography business grew because I never gave up, even during the challenging early days when inquiries were few and far between. Instead of waiting for opportunities to come to me, I stayed proactive—always creating content, building connections, and finding ways to grow. Read more>>

Stefanie Gass

I started my current business after my once-successful network marketing business crashed. I went from high-income months to NOTHING for about a year of my life. My husband had to sell his Harley Davidson and we had to borrow money from my son’s savings account just to get by – it was bad. The Lord knew I needed these hard, heart-breaking moments to overcome my idolatry of money and to bring me back to him. Read more>>

Cory Ferris

I started Ferris Fitness with a dream to help others overcome loss, battles with addiction, and stagnancy. I offered my training services free of charge during covid to help others. I started with recording exercises, and sending over videos with how to do it, and writing down all the sets and reps. Read more>>