Building & Scaling a Business without Sacrificing its Soul with Cleo Massey

What if the smartest thing you could do for your business was stop chasing what looks successful and start listening to what genuinely feels right?

In this episode of In Real Time with Millie, Millie sits down with actress, entrepreneur and Pass Around the Smile founder Cleo Massey for an honest conversation about building a business through authenticity, intuition and genuine human connection.

Cleo shares how she moved beyond the identity and pressures of the acting industry, followed the unexpected pull toward spirituality and transformed a personal blog into the thriving Pass Around the Smile community.

Together, Millie and Cleo explore the realities of comparison, people-pleasing, scaling a purpose-led business and learning to prioritise peace without abandoning your financial goals. They also unpack why community cannot be manufactured, how to distinguish intuition from fear and why chasing the wrong audience, partnership or version of success will only take you further away from yourself.

In this episode:

Why Cleo walked away from the identity she had held since childhood

Building a loyal community through consistency and real connection

The danger of chasing “cool” customers, brands and opportunities

Choosing heart over money without undervaluing your business

Setting boundaries when your personal brand relies on access to you

Navigating comparison, rejection and self-doubt

How to tell the difference between intuition and fear