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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
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