Episode overview

Caitlin Judd joins Steve Grace for an open conversation about the experiences that shaped her path from Melbourne’s eastern suburbs to Miami, through a brief corporate career, and into building Lady Brains as a platform for female founders. The episode explores mentorship, the gender funding gap, and the balance between ambition and self-compassion.

Melbourne to Miami: the exchange that changed everything

Caitlin was studying a bachelor of business marketing and media at Monash when she spotted an exchange program to the University of Miami. None of her friends had considered it. She went anyway and describes the six months as living three years in half a year. She fell in love the first weekend, stayed for nearly two years, sold high-end art on Fisher Island, worked for a glossy magazine, tried acting, and created a behind-the-scenes segment at the second biggest theatre in America, complete with sponsors for hair and makeup. She was 21.

The corporate hiccup and the entrepreneurial pull

Back in Melbourne, Caitlin took a “real job” in corporate marketing in the manufacturing industry. It lasted two and a half years. She describes it as a hiccup, not a sliding door moment. She knew while driving to work on autopilot that it was not right. By 25, she was back out on her own, freelancing and supporting female entrepreneurs in the wellbeing sector. The entrepreneurial pull had always been there.

Lady Brains and the power of community

Caitlin built Lady Brains as a podcast and community for women in business. It became both a personal growth tool and a platform for exploring angel investing and the gender funding gap. She talks about how the podcast gave her access to conversations and networks she would not have found otherwise, and how creating something from nothing is the most rewarding and wild adventure.

Self-compassion alongside ambition

Caitlin is honest about pushing her independence too far. The same drive that got her to Miami at 21 can become exhausting. She talks about practising self-compassion, kindness, and the understanding that if things are meant to happen, they will. You still need to be open and willing, but you do not have to force yourself through the world.