Pushing Past Fear and Betting on Yourself with Salon Owner & Content Creator Reagan Kaalekahi

Most people wait.

They wait for the “right time.”

They wait until they feel ready.

They wait… and never actually go for it.

In this episode, I’m sitting down with Reagan Kaalekahi—entrepreneur, content creator, and founder of one of San Diego’s most sought-after salons—to talk about why waiting is the fastest way to kill your dreams, and what it really takes to build something when the fear is loud and the path isn’t clear.

This isn’t just for salon owners. It’s for anyone ready to:

- Stop second-guessing and start betting on yourself

- Push through fear and uncertainty to create the life you want

- Learn how to invest in your own growth, even when it’s uncomfortable

- Build a personal brand that pulls in the right clients, opportunities, and collaborators

- Balance business growth with family life without losing your mind

- Take risks that actually move you forward

Reagan shares his journey from cutting hair in his parents’ garage to running a thriving business, plus the hard lessons and mindset shifts that made it possible.

If you’ve been stuck on the sidelines waiting for a sign—this is it.

Connect with Reagan:

📸 Instagram: @longhairswag

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