What happens when one of the best pro skateboarders in the world trades his board for a business plan and then a city council seat?

Today, I sat down with Mikey Taylor, a man who has lived many lives. From being a world-renowned skateboarder to co-founding a brewery that exited for $80 million, to now managing over $300 million in real estate assets and serving as mayor pro tem of Thousand Oaks, California. I mean, where do we even begin?

But what struck me most wasn't just his success, it was his transparency. Mikey opened up about his identity crisis after retiring from skating, the wake-up call in his marriage, and the emotional cost of chasing success at all costs. We talked about how he rebuilt everything from the ground up, this time with his family at the center.

We dive deep into:

🔥What it really takes to build and exit a successful business

🔥The secret sauce behind building a brand people actually connect with

🔥How to invest in real estate without becoming a full-time landlord

🔥The identity shift that comes with letting go of who you were

🔥And why being vulnerable is the most powerful thing you can do online

Mikey reminded me that people don’t connect with perfection, they connect with the journey. The mess, the struggle, the rebuild. And man, this episode cracked something open in me too.

Whether you're building your brand, launching a fund, or figuring out who you are beyond your job title, this conversation is for you.

Tap in. You’ll feel this one.

Key Moments:

1:30 - Who Is Mikey Taylor?

4:13 - Trading a Skateboard for a Business Plan

9:04 - Betting on California Real Estate

13:33 - From Beer Idea to $80 Million Exit

24:03 - The Power of a Mentor

29:04 - 80M in Four Years

35:00 - Letting Go of the Hustle Myth

40:47 - Delegation Is the Only Way

45:04 - $140M Under Construction with a 20-Person Team

52:30 - Merging Missions, Building Momentum

57:25 - TikTok Taught Me This

1:02:06 - The Hardest Part of Running a Fund

🚩SUBSCRIBE 🚩 to my Youtube Channel Here: @hannahbhammond

Connect with Mikey Taylor:

IG: https://www.instagram.com/mikeytaylor/?hl=en

YouTube: https://www.youtube.com/ ⁨@mikeytaylor⁩

Facebook: https://www.facebook.com/RealMikeyTaylor/

2025.09.25: Never Swallow The Worm