Meet the Skater Who Went from Uber Eats Driver to Headlining His Own Comedy Tour

You said you and your brothers all started skateboarding. How did you get into it?

Caught the bug. Simple as that. Got my first board, slept with it in my bed, didn’t skip a day if there was ever a way to avoid it. Even today, I just can’t stop thinking about it. Skate videos remain my favorite content on earth. 

What led you to going to film school in Vancouver?

To meet you! I wrote, directed and starred in a play my senior year of high school. I fancied myself a young Orson Wells on a skateboard. An “Orson Wheels” if you will. I was already making skate videos, and after the play, film school seemed like a natural step forward. My goal was always to make movies with skateboarding themes and characters. Still is. Vancouver was just where the school I could afford to go to was. I had no idea it was the skate Mecca of Canada. Needless to say, I was a bit distracted that year.  

Why did you move to New York?

Comedy. I had no idea it was the skate Mecca of the east coast. Needless to say, I was a little distracted that decade. 

What was life like in New York at first?

New York baby! Hard, fast and fun. Comedy was insanely hard for sure though. I was a new comic anyways, but it was so so much tougher to get laughs than I ever could have imagined. Luckily I had you, and we were such fanboy skaterats, all I can really picture when I imagine those times, despite how hard it was, is you and me shredding that famous NYC landscape! Best of times. Worst of times. 

Amazing times. Then you got into real estate, right?

I was less than a year into living in Brooklyn when I sat down face to face with my landlord. Just to go over my lease. I walked into his office with one goal; negotiate my security deposit down. I walked out of there with not only a lower security deposit, but a new job. He hired me to start renting his apartments. The timing was perfect too because I was in desperate need of money. He actually didn’t know that or he probably wouldn’t have rented to me in the first place. 

You kind of quit skating and comedy at that time?

I wouldn’t say quit, but compared to how much time I previously dedicated to skating and comedy, yeah, I basically quit. They require so much effort and concentration, just to maintain, let alone progress. When I got this job, I was forever dedicated to it. I never got any real success in comedy, nor did I ever truly chase it. I had also just destroyed my ankle skating. Which made that choice easy. I felt old for a pro career anyways. Through the years I kept popping in to open mics and producing indy shows. I would also keep hitting parks and filming clips when I could, but comedy and skating just kept fading further into the background, especially after my son was born. 

Then real estate brought you back to Seattle?

Yeah. We moved there to launch a real estate start up. 

What happened?

It collapsed. 

So at that point, you’re back in Seattle, you’re not skating, not doing comedy and your career just collapsed. But out of that you completely changed your life, right? Your habits, your mindset? What led to those changes?

While I was trying to get the real estate business off the ground, I fell deep into entrepreneurial self help. So much of the content I was consuming revolved around building good habits and having passion. I wasn’t passionate about real estate and I had terrible habits. I couldn’t help but think that if only I had adapted these success models, but in my comedy career, or even my skate career, I would have been successful. But it felt too late. So, I kept reluctantly and sluggishly trying to force the models onto my real estate business. 

Coincidentally, as my business was on its last breath of life, I got asked to audition for a comedy contest. I got in, and did well. After that I doubled down on comedy. I started cutting ties with my real estate career and began building healthy habits. I knew the better habits I had, the more likely I was to become a headlining comic. 

I took it one habit at a time. First I quit smoking and drinking, then started eating super healthy and exercising. Then I made habits out of writing, filming my sets, making edits, sending booking emails, networking, and I’m still stacking more habits one day at time. 

What was the main thing that led you back to skating and comedy?

Showing my son the importance of never giving up on yourself, was, and still is, my North Star. I was passionate about skating way before comedy and in my core I knew I was doomed to be thinking about skating for the rest of my life. As well as I was doomed to be wanting to perform jokes for the rest of my life. The more I’ve tried to fight those parts of myself, the worse I’ve felt. So now I don’t try to fight it and I feel great. Minus the frequent and always sudden agonizingly painful injuries. 

How did you tell your wife about your "career pivot"?  From making a lot of money doing real estate at one point, to now chasing your skate and comedy dreams?

She said “no”. That's how she handled it. And I say that to her credit. That’s actually the right answer. Half of the reason I changed so much of my lifestyle was to prove to her, and myself, that I was capable of succeeding in a career so difficult to pursue. It requires more than just being funny. She never thought I wasn’t talented enough to make it. 

What is it about Gary's content that resonates with you? Is there any big learning/takeaway you got from him?

There are more than a few game changing “Garyisms” I’ve worked into my philosophy.  Finding your passion, giving more value than you get and thinking long term. These three pillars support everything I do. 

So true. Gary always speaks about leaning into your passions and strengths. And that's exactly what you're doing. It’s quite distinct to what you're doing.

Yeah for sure. Leaning into my strengths as a comedian and skater lit the match, but I truly believe if I hadn’t already been leaning into my strengths as a salesman, a coach, a father and a husband, then the match would have gone out. Instead, it created a fire I can control and build onto.

You've had so many ups and downs in your journey. But you've always remained so positive. You've always dreamed big. Has it been hard to keep your perspective?

I don’t think it’s hard to stay positive if you have gratitude. However, having gratitude is easier said than done. In my darkest, most hopeless moments I would resent my big dreams for leading me toward inevitable failure, I would dog on my own positive spirit for being blind to the world's misfortune, and I would struggle to find anything to be grateful for at all. Luckily I always find it. Come back and ask me again after I blow it. 

Having been through so much, do you think you appreciate everything that is happening to you more now?

To say the least. If it weren’t for every single one of my failures, not only would I not appreciate what’s happening, it wouldn’t be happening period. 

Has anything surprised you about the feedback you've gotten? Surprised by what people are responding to?

I was and still am surprised people like my skating so much. I was confident being a decent skater would boost my legitimacy in the skate world, but I did not expect at 36 years old for people to be so hyped on my skate clips. That’s a dream I abandoned many years ago, but am more than happy to bring back into focus. 

What is next for you?

In the immediate future I’m pushing my first live comedy tour, check my website for dates, but I’m really excited about my web series. It's called “comedians at skateparks”. It’s my dream job. Skate all day and hang with comics, and then do shows at night. In the long term I wanna make movies and put out comedy specials. Then I want to move into your house, and be roommates again forever. My wife and son are already on board so, it’s on you to tell them you’re not interested. Go ahead, break their hearts. I dare you.

Ha! Love you, Tay. 

Love you Big Guy.