Mikey Taylor sits down for a wide-ranging conversation that traces an unlikely path: hard-charging pro skateboarder who turned his parents’ neighborhood into a legendary skate house, built signature product deals and royalties, launched (and exited) a craft brewery after Rob Dyrdek crumpled up the business plan, founded real-estate firm Commune Capital, and became mayor of his hometown—all while reordering his priorities around faith, marriage, and kids.

They dig into the real economics of extreme sports, how young athletes (and their parents) should think about sponsorships, social media, and long-term money, why most pro athletes still go broke, the difference between building to exit versus building a machine, contrarian California real-estate investing, and the practical systems Mikey uses to protect family time while running multiple businesses and serving in local politics. Honest, tactical, and grounded.

Chapters

00:00 – Sean Malto’s text & the legendary 2007 skate house

04:30 – Skater → founder → investor → mayor

09:20 – How extreme athletes actually make money

13:00 – Parent playbook + the hard “no” on kids and social media

18:00 – First pro checks, royalties & the early money discipline

25:20 – Rob Dyrdek’s 10-year rule on business

31:00 – Building to exit the right way (vs. cash-flow machines)

39:00 – Why become mayor when there’s zero upside?

43:30 – Contrarian California investing + favorite markets

51:00 – Athlete money playbook: control lifestyle or lose it all

56:30 – The hard reset: God → wife → kids → business

1:03:40 – Definition of success + final 10X challenge