The Find Your Grind Podcast, Episode 7: Mikey Taylor on looking beyond the expiration date of going pro


The Find Your Grind podcast is a weekly series hosted by our founders, Nick Gross, Natasha Gross, Mike Smith, and Luke “The Dingo” Trembeth. Each week, we speak with special guests on the first 10% of their personal journey, decisions that led them where they are today, and how they built their ideas from finding their grind. In this week’s episode, Nick and Dingo sat down with pro skateboarder turned real estate investor, Mikey Taylor.

Entrepreneur and Thrill Seeker, Mikey Taylor, discovered his purpose when he lost everything. The pro skateboarder hustled to fight for his passion, obtained sponsorships, and built a business model to financially support himself before he was 18 years old. At one point, Mikey Taylor was being sponsored by the biggest in the industry — DC, Spitfire, etc. However, what he abruptly learned were the loopholes and expiration date for skaters which led him to pivot into his next career juncture as an entrepreneur and real estate investor. 

As a kid, skateboarding organically entered Mikey’s life. Once his shoes stuck on that grip tape, he knew he loved it. Growing up in a small suburb, his passion of wanting to skate all day was an obscure and unpopular opinion. But he stuck with what he loved. When his parents combated and challenged him that skateboarding doesn’t pay — Mikey set himself out to get sponsored by companies. With friends, he created a three minute VHS tape, made copies, and mailed them out to skate magazines. Shortly, he was signed by Venture Trucks, Maple Skateboards, and DuFFS Shoes. He’d fortify his business plan by selling gear he received to make extra cash. By 17 years old, Mikey had secured his first ad in a magazine. And by 18 years old, he’d be on editorials and “Check Out” sections on the glossy pages. Growing up in a time when college messaging centered on the way to land a big job, he was placed in a predicament to either choose to tour with City Stars Skateboards or attend college. Mikey Taylor found compromise, and went to tour for 2 years then attended college. 

Tour became a formative time for Mikey. Within the 2 years of traveling in Europe, he gained real life experiences (like learning a new language) and information that he retained more than being in a classroom. By the time he reached his 2nd year of tour, skateboarding had become a global phenomenon and the rates/payments for skateboarders shot up. Mikey was living his dreams and enjoyed every part of it — the passion, the influence, the sponsorships — but was smart with his money through a financial advisor. However, what he abruptly learned were the loopholes and expiration date of being a pro skateboarder. A loophole in his contract caused him to lose his biggest sponsorship, but eventually would lead him into his next investment opportunity.

Mikey Taylor on the Find Your Grind podcast

Mikey pivoted by taking his influence and branding experience to create Saint Archer Brewery with his friends. Capitalizing on their clout, they marketed craft beer at the right time and demographic. One of the largest beer acquisitions, they sold the company for over $40 million dollars to Coors. Learning about being financially independent and smart, Mikey found his purpose in educating others. The biggest outcomes in his experience was learning to be specific in exactly what you want by asking questions such as “what will make you happy?” — which can be broken down to your next steps and to help you seize the moment now. Mikey understood while realizing his finances that his pro career had a timeline and he needed to configure his money so he can invest himself after. His untraditional model shows that you can DIY your career path with gut, knowledge, and mentorship.

Check out the episode in full and be sure to check out The FYG Podcast on Apple Podcasts and YouTube.

This episode’s references can be found here:

3:17 – VHS 

3:20 – Kinko’s

3:28 – Blockbuster

4:02 – Venture Trucks

4:03 – Maple Skateboards

4:04 – DuFFS Shoes

6:29 – City Stars

10:57 – Tony Hawk lands 900 

26:37 – DC Shoes

28:21 – Saint Archer Brewery

28:51 – Paul Rodriguez

38:11 – Red ocean

38:21 – Blue ocean

47:15 – FYG Lifestyle Assessment

Are you an educator or a teacher?

Find Your Grind has a variety of educational products in schools across North America.

learn more