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In this episode of The Mailbox Money Show, Bronson Hill sits down with former professional skateboarder, entrepreneur, real estate investor, and current mayor pro tem of Thousand Oaks, California — Mikey Taylor. Recorded right in Mikey’s own office, this conversation goes far beyond skate culture and business.

Bronson and Mikey dive into the evolution of Mikey’s career: from turning street skateboarding into a global platform, to founding and selling the iconic craft brewery St. Archer to MillerCoors, to building a real estate investment company, and ultimately stepping into public service. Mikey opens up about identity, risk, and reinvention — and how facing the end of a dream forced him to build a future with intention.

If you’re interested in entrepreneurship, investing, personal growth, or simply hearing an honest conversation with someone who’s reinvented himself multiple times, this episode is a must-listen.

0:42 - Episode Intro

0:49 - Guest Intro: Mikey Taylor's Background

1:31 - Pro Skateboarding Career Start

2:10 - Planning Life After Skateboarding

2:56 - Pros/Cons of Pro Skateboarding

5:26 - Cons: Uncertainty and Injury Risk

6:10 - Transition from Skateboarding

6:21 - Discovering St. Archer Brewery Idea

7:20 - Pressure to Prove Stability

9:11 - Sale to Miller Coors

10:40 - California Lifestyle Lens

12:49 - Reflections on Charlie Kirk's Passing

14:14 - Jordan Peterson on True Belief

16:07 - Choice: Trapped or Free Expression

17:25 - Living Authentically Amid Backlash

21:32 - Future: Politics or Business?

23:40 - 2025 Multifamily Deals Outlook

24:00 - Challenges in Raising Equity

26:17 - Housing Crisis: Deregulation Solution

29:21 - California Apathy and Exodus

31:50 - Need for Political Balance

35:02 - Connect with Mikey Taylor

Connect with the Guest:

Instagram: @mikeytaylor

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

Youtube: https://www.youtube.com/c/mikeytaylor

LinkedIn: https://www.linkedin.com/in/mikey-taylor-1607b3111/

#MultifamilyInvesting

#EntrepreneurJourney

#SkateboardingToBusiness

#AuthenticLiving

#RealEstateDeals

#CaliforniaHousing

#PersonalValues