Offsite Interview Series: Steve Bryant
As part of an ongoing series to gain insight into new perspectives, we explore the bright minds of other makers, creatives, and innovators that may be off your radar. We’re doing this by interviewing people behind the pioneering businesses and ideas, both new friends and old.
October 26, 2015
Today I have the pleasure of speaking with fellow Offsite alumnus Steve Bryant, a writer and editorial strategist based in New York.
Steve was the founding editor of InsideHook, a daily lifestyle guide for “adventurous and discerning men.” He was also an original editor of Thrillist, a former Hollywood Reporter columnist, and an occasional writer for Esquire.com and NYmag.com. He now runs his own consulting business advising on editorial strategy and branded content.
Aside from his editorial endeavors, he’s also well versed in the events world, as the founder of Rental Car Rally — an overnight, costumed roadtrip in which teams compete for prizes and cash. (Yes, it is as awesome as it sounds and you should certainly check it out yourself).
Given our upcoming roadtrip, we thought Steve would be great to kick off our interview series, perhaps giving us some inspiration for life on the road, and also provide some insight into his own creative process.
Thanks for joining us, Steve.
Steve: Thank you so much for having me. Gonna be a good time.
Derek: Alright let’s dive in — so when did you discover you wanted to be a writer?
Haha, oh, I don’t know probably when I discovered I didn’t like math. Honestly, I don’t remember exactly. I didn’t want to take other classes in college so I ended up taking a lot of literature classes and just got really into it.
Was there a turning point when you realized you wanted to make it a career?
Yeah, actually. I was working at a startup in Virginia, which is kind of an oxymoron. I think this was around 2001. I really wasn’t happy and had decided I was going to quit. I was going to move to Taiwan to teach English, but then I realized I didn’t really want to go to Taiwan and teach English. It just so happened that a family friend was running a magazine in Richmond, so I got in touch with them. I had a lot of fun doing the magazine thing and then one thing led to another.
What’s your approach to telling a good story?
Ha, first have two drinks. I think, number one, you have to flatter the listener or the reader or the viewer. A predominant emotion should be one of hospitality to the people that are talking to you or reading what you wrote. I think that when you’re younger, you know when everyone thinks they’re a really smart kid, you might have the intuition to show off a little bit and try to show people how much you know. I think that in order to tell a good story, it’s less about showing off and more about taking the reader or the viewer or listener along with you. So I think that’s probably the number one thing.
Obviously you’ve written quite a bit in your day, can you share a piece you did that you’re most proud of?
I would say I’m actually most proud of a piece I’m working on right now. It’s not actually assigned anywhere, just a pitch. I just got back from Calgary where I was interviewing a young poker player named Jamie Staples. This kid is 24 years old, and he not only plays poker online, but he also stream casts his games on Twitch.
He has about 2500 average viewers, which is REALLY interesting, from A LOT of perspectives. I mean he’s playing poker on Twitch, which is a video game platform — you’ve got Call of Duty, HearthStone, World of Warcraft. It’s not known as a place where poker players spend their time.
But he’s understood — I don’t know if it’s intuitively or if he researched it — that the entertainment value of poker, of actually showing people what he’s doing, teaching them, is ultimately more valuable than the money that he wins playing poker itself. So that’s something I’m working on and I’m very proud of the story and finding it.
Are you a poker player as well?
I am a very poor poker player, so you should definitely invite me to your next game.
I’d love to explore the story behind Rental Car Rally. Can you tell us a little more about how it got started?
Rental Car Rally is a overnight road trip in costume, from one city to another — New York to Montreal, Los Angeles to Tombstone, AZ, New York to Detroit, San Fransisco to Yuma. It really got started in 2008 when I talked to my friend Franz, who I had just met. I was doing a Wii Tennis tournament at Barcade out in Brooklyn, and Franz was running a water gun assassination tournament called Street Wars. So we were both doing super kooky things. He was like “we should totally work together.” I said, “we totally should.” “You have any ideas?” “Absolutely none.”
So we sort of talked about our lack of ideas for a while and then I said I always wanted to do something with cars, Cannonball Run always looked like a lot of fun (The Cannonball Run is on old movie with Burt Reynolds and Farrah Fawcett, and actually based off a real life thing). He said yeah me too, but only problem was that we didn’t really have any money. Back then in our 20s it was difficult to find the money to even rent a car. So instead of doing a cross country race like Cannonball Run, we decided the easiest thing to do for people like us was doing an overnight from one city to the next, and only took one day.
What’s the best costume you’ve ever seen?
Oh man, haha. This group, the Party Pirates, they literally bought a school bus and painted it red. They took out all the seats and they basically made the interior a bunk house type of thing, and decked it out in curtains and pirate regalia. They drove that bus across the Mojave, all the way from LA to Las Vegas.
So it seems like you have a knack for creating these out of the box, novel experiences. Where do you get your inspiration?
I don’t know, I think it’s kind of like everybody else. I like certain things and I have certain interests and curiosity. When you have interests and you follow that interest and make it a passion, and you’re curious about all the elements that go in to it, I think the ideas come that way. I don’t think anyone ever got a great idea because they were bored or because they didn’t want to learn more about the world.
On that note, I’d like to transition and learn more about your day to day and a little more about Steve. What keeps you motivated?
Ha, probably looking forward to a good drink at the end of the day. I think the awful two answers, that are absolutely true — anyone reading this is probably gonna be thinking ‘what a weirdo,’ — are a drink and fear. I’m just absolutely afraid of not accomplishing the things that I want to accomplish. I think I came later in life to the idea that I could do anything that I wanted to. And I feel like I’m still doing that climb, so climbing and accomplishing and doing things that I love, and doing them well, is what keeps me motivated.
What does your morning routine look like?
I actually just got back into it, thank God. I was in Toronto and Calgary and got a bit out of it, which unfortunately happens when you travel. But this morning I got up, I made coffee because I didn’t set the coffee timer last night, because I’m a genius, and while the coffee was brewing I meditated for 10 minutes. This is actually a new thing for me, it’s kind of fun. I don’t want to wake up and check email and that sort of thing.
So that’s like 6am, I meditate for a few minutes and more or less work from 6 to 9 on whatever writing project I’m doing. Then I take a shower and go down the street to this little diner. There I’ll have a bowl of oatmeal with fruit and a side of bacon, which is really ridiculous because they pretty much cancel each other out. The rest of the day is whatever meetings and projects I have. Its really important for me to get up early though, and start the day off right.
What do you do to find clarity? We discovered you have a meditative practice, but what do you when you’re losing focus?
Usually just leave the computer. It’s just so hard, it’s so hard, right? Don’t you find it hard to do? Especially when you end up going back and forth through email and you have so many tabs. The challenge is always that every single individual action you take on the internet is itself very simple — it’s just a click. But you can go down a deep hold of clicks, you click that one thing and you know that it’s going to lead to another 20 more. Next thing you know it’s been minutes and you’re stuck in this time hole. It’s difficult and I struggle with it every day.
Oftentimes that has to be a physical thing, like go for a run or walk or ride my bike. It’s really difficult to go from being on a computer and inputting things and receiving things to doing something where you’re just receiving. I can’t go from being on a computer to reading a book.
What is one thing you strongly believe in that most people may not believe?
You know, I feel like everybody took my thing. But I’d say I think that you have to expect the best from your fellow humans, because even if they do evil things, that we’re all just coming from a place of insecurity and quite frankly probably fear of dying, and that’s what makes us do things that are awful to each other. But I don’t know, I kind of think that a lot people believe that now. All the millennial folks are all just so overwhelmingly positive that it’s difficult to really fly the positive flag anymore because everyone is positive.
Lastly — this one really irks me — do you believe that a hot dog is a sandwich?
…Yeahhhh. It’s kind of a sub type of a sandwich, right? Because if it wasn’t a sandwich what would it be? I don’t know that there’s any other genetic phylum that it would belong to. You have open sandwiches too, are open face sandwiches hot dogs? No. Somehow I think the scientific taxonomy system bypassed the culinary world and I’m pretty sure they could probably do some rearranging.
Where can people find you?
If they’re inclined, they can go to thatstevebryantguy.com. Oddly enough, that domain wasn’t taken. I got it for a song.
