Coat & Shoes: Golden Goose
Button Down Jacket & Pants: Filippa K
Talent: Tyler Regan
Photography, Creative Direction, and Production by: Mike Ruiz
Editor-in-Chief: Dimitri Vorontsov
Stylist: Star Burleigh
Stylist: Amana-Re Brown
Location: Las Vegas, Nevada
Blazer and Trouser: Filippa K
Necklace: David Yurman
Coat: Orttu
Boots: Saint Laurent
Dimitri: How was your photo shoot with Mike Ruiz?
Tyler: Mike’s great. He’s super talented and made it super easy. When you have someone who can not only find a good shot, but also direct the subject, it makes life extremely easy.
Dimitri: Mike told me you had a really interesting story when you were going to the photoshoot in the desert, because you are also a big animal lover like Mike. You stopped the car and blocked the highway because there was a dog crossing?
Tyler: Oh yeah [laughs] We were driving for only like 5 minutes, and we had just gotten onto the highway, and these two gorgeous huskies came running by us on the shoulder of the road. Like the opposite way of traffic. I pulled over immediately, and Mike just started running down the road after them.
It’s kind of a trend that has lasted my entire life. I’ve chased down dogs, and watched lost dogs more times than I can count. I love that Mike had the same reaction. I get it from my mom. I’ll always stop to help animals.
Blazer and Trouser: Filippa K
Necklace: David Yurman
Coat: Orttu
Boots: Saint Laurent
Dimitri: Before comedy, you were training to become a professional soccer player. I don’t know if it’s still a touchy subject for you or not, but what happened? It must have been like an injury or something, right?
Tyler: Yes, it was an injury. I would say, if you were asking me this two or three years ago, it would still be a super touchy subject. I guess it still gets to me though at random times. There’s times that it still affects me more than I would expect. Like I got all emotional during the season 1 finale of Ted Lasso [chuckles].
I just always wanted to be a pro soccer player. Played Division 1 at Cornell University, and had opportunities for professional contracts before my injury. Snapped my ankle basically in half. My pro career more or less ended before it was able to fully start.
Since then it’s kind of manifested itself as heightened pressure to do a good job with my content and to kind of reach that same potential that I feel I would have reached with soccer.
After the injury, I was just really depressed. I had no direction. I tried coaching, personal training, project management, everything. There was always film in the back of my head, cause I had done it my whole life and throughout school, but I guess I was scared of “starting a new dream” and having it go south again. Luckily I had some amazing people around me, some being content creators themselves, and they pushed me to find my passion again.
It took some time for me to really find my voice with my videos, but now I really feel I have. So circling back to the original question, for the first time, it’s not as hard to talk about soccer anymore. Before it was like “I lost soccer, and therefore my life sucks’. Now I can look at it and say “If I never lost soccer, I wouldn’t be where I am today” It can finally be spun into a positive.
Blazer and Trouser: Filippa K
Necklace: David Yurman
Boots: Saint Laurent
Dimitri: Tell me, you probably went through so many different versions before you found your voice as a comedian. I personally am able to see some Dave Chappelle in your sketches. Was he somebody that influenced you growing up?
Tyler: Oh without a doubt Dave Chappelle is a massive influence for me. Growing up I would watch him and Chris Rock religiously. Lots of other comedians too, but they were two major ones for me. Another big influence has to be Monty Python.
Top: Guess
Jacket & Pants: Orttu
Boots: Salvatore Ferragamo
Jewelry: David Yurman
Dimitri: That’s surprising because it’s not that big in the US as far as I understand.
Tyler: It’s not but Monty Python to me was the peak comedy. I’ve always loved how intelligent and dry their humor can be. You see it a lot from Noel Fielding and other British comedians too. When I write, I always try to blend a bit of Chris Rock-style humor and add it to that dry style.
It took some calibration for sure. In the beginning, my humor was probably too dry and too subtle, with too long of burns if that makes sense. Then I over-corrected for a bit. I like where I fall now though, because I am able to go either direction and the audience seems to appreciate it.
Dimitri: At which point did you find that you could do those sketches?
Tyler: During the pandemic I was kind of forced to adjust my content. I was really only on YouTube and used to use big crews and actors for the videos. Covid forced me to be more of a one-man show, and forced me to get a little creative with how I did things. It’s why I even got into TikTok in the first place.
Sweater: Aknvas
Rings: David Yurman
Dimitri: I’m really into your Karen sketches.
Tyler: [chuckles] I find that people either love the Karen stuff or hate the Karen stuff.
Dimitri: I love it.
Tyler: She’s a fun character to write for. I wouldn’t say they are my favorite videos I make. There are definitely other ones I tend to lean towards, but those ones are a good time.
Dimitri: I also love the Olive Garden sketch you just made. The one poking fun at how it’s “authentic Italian food”
Tyler: Dude so many people got mad at me for that video
Dimitri: Really?
Tyler: I always find it fascinating to learn which videos get the most people angry at me. I mean, it’s comedy, it’s subjective, and it’s always making fun of something, so you always run the risk of someone disagreeing with you. But sometimes I am blown away by just what hill people are willing to die on.
Like sure if I make a political video, I get it. You’re inviting some backlash. But when I get hundreds of DMs threatening me for making fun of Waffle House, that’s always hilariously odd.
The funny thing about it is that most of the things I make fun of, I genuinely like. That’s why I know all of the weird nuances of the place. It’s because I go there. You can love something, and make poke fun at it.
Coat & Shoes: Golden Goose
Button Down Jacket & Pants: Filippa K
Dimitri: You’ve amassed this massive fan base.Did you start with Vine first?
Tyler: I missed the Vine wave, which sucks because I love old Vines. I was still in college, and playing soccer at the time, so I just never had the time to actively create anything there.
The first platform I did anything with was Instagram. I made it while I was still a project manager to document my vacations and travels. I was able to get a couple of small brand deals on there, but it wasn’t until I started my YouTube channel that I really would say I “tried to make a real attempt at it”. I know I said it before, but I was lucky to have some people who had already become successful with their content guide me.
Dimitri: Are you still doing YouTube?
Tyler: Kind of. I have this old YouTube channel that I don’t really use anymore.It has a decent following still – something like 410K, but I don’t foresee myself going back to it. I actually started a new YouTube channel recently, which has my new style of content.
YouTube is just a tough platform to pivot on, and I spent a lot of time pivoting. Since it was my first video platform, I didn’t really know what kind of content I wanted to create, and so I kind of just created everything. That admittedly made it hard for followers to know what to expect. So then I started chasing what I thought people wanted to see, and so the content got farther and farther away from what I truly wanted to create. I renamed it TheOldTylerRegan, because that is genuinely what it is.
When the pandemic started, it forced me and really everyone to take a pause, and assess what it was that mattered most. While YouTube was successful on paper, the content wasn’t fulfilling me in any substantial way.
I started TikTok with the promise to myself that I would only make videos that I enjoyed and that if the views came, great, and if not, so be it. I’m obviously happy that it was successful – it has something like 1.5 million followers and 250 million views – but I’m happier that I’m enjoying making content again.
I am now using Instagram again and I started a Facebook page about 6 months ago too. All of the pages have the same style of content, but they all get exclusive videos. I love that finally everything feels coherent.
Necklace: David Yurman
Button Down & Coat: Golden Goose
Dimitri: The TikTok videos are pretty short right? Like 30 seconds?
Tyler: Yeah, they’re usually around 30-40 seconds.
Dimitri: For Facebook, you’ll be doing a little bit longer?
Tyler: Facebook and YouTube do get longer videos, but short form content is thriving on both of those platforms as well. I use Facebook Reels, and YouTube shorts for more daily posting, and then post a longer video weekly as well
Dimitri: Are the longer ones the same style?
Tyler: Right now they are. I even incorporate the same characters sometimes. Like I just did a two-parter about Karen going to jail. I play all of the characters still. I do want to eventually get back into using actors for some videos in the future.
Dimitri: And do different platforms get different videos?
Tyler: It’s on a bit of a video-by-video basis. The Karen videos for example tend to be enjoyed on all platforms, and so I will post them everywhere. On the other hand, some content tends to only do well on Facebook or only do well on TikTok, and so I will make those videos exclusives to a specific platform
Dimitri: You’re really giving a pretty truthful spiel about how things are done. People reading may be able to use this as almost a manual for how to grow your platform and stuff.
Tyler: Hopefully it is helpful! I had help learning the ropes when I was getting started, so it would be messed up if I wasn’t willing to lend that same hand to others [chuckles]
Top: Guess
Jacket & Pants: Orttu
Shoes: Golden Goose
Jewelry: David Yurman
Dimitri: Do you ever see yourself doing standup?
Tyler: You know I get asked that all the time, and I still don’t know. I do know a podcast is on the horizon for me, and I guess that could fill that same void if that makes sense. I probably will do stand up at some point though
Dimitri: At least once…
Tyler: At least once. You have to try everything at least once.
Dimitri: Look more into the guys that inspired you growing up. Maybe you’ll get into it. You could start selling out the Hollywood Bowl!
Tyler: If the Hollywood Bowl wants to book me, and then thousands of people want to come see me, all with me having no stand up experience, bring it on. That would be wild [laughs]
Dimitri: You write as well. What’s your preferred genre?
Tyler: I obviously am partial to comedy. I also really enjoy those mindfuck movies and horror [chuckles]. When I was in like, 2nd grade, I told my parents I wanted to be a director. My first love was music videos, but then I started making narrative driven stuff in my friend Jeff’s basement. We were still filming and editing on a camcorder at the time. When I was younger I thought more in black and white terms. Like this is a comedy, or this is a drama, but now I think the best results come from blending genres. The Office and Ted Lasso for example.They both can make you laugh one scene and cry the next.
That being said, I also do love a good full-throttle outrageous comedy. Something like Pineapple Express or Eurotrip ya know?
Dimitri: What do you love doing in your spare time besides your content.
Tyler: I love to travel. It used to be just international travel, but I just got finished with a 6-month road trip to see the US which was a wild adventure. My girlfriend and I renovated a 1976 Airstream, and took it from coast to coast. This upcoming year, I’m planning on a few more trips with it.
I also play and collect video games. A lot of vintage stuff. Plus, with my background in soccer, I try to stay active and go to the gym and all that good stuff
Dimitri: If you could give your younger self any advice, what advice would you give yourself?
Tyler: If this is like middle school or high school Tyler, the advice would be to not be too worried yet and to give yourself time to find yourself. I wasn’t fully accepted growing up, and it made me over-try for sure. Everything I did was kind of pre-planned and pre-thought-out. I would let my younger self know that going through that would eventually be a good thing. It’s good that you’re going through that. It’s good that you’re trying to figure out who the hell you are because some people never figure it out. Yes, I would say that’s probably the biggest advice. I’d also tell my younger self to buy Bitcoin back in 2009.
