Eight Questions with Jesse Tyler

Springfield’s fourth- or fifth-best person to invite to a party is taking to the streets to cycle across the United States raising money for a good cause.

Written by Lillian Stone | Photo by Kevin O’Riley

Jun 2016

Jesse Tyler.

Hanging out with Jesse Tyler makes for a pretty good time. Earlier this year, 21-year-old Tyler spent several months battling to win 417 Magazine’s “Best Person to Invite to a Party” title. After Tyler failed to place in the top three, a friend created a Kickstarter campaign to fund his consolation trophy. When the campaign closed, 12 backers had pledged $164 to honor Tyler’s fourth- or fifth-place finish. The result was a gleaming trophy nearly six feet tall. The trophy—currently on display in Tyler’s home as the shiniest thing he owns—features a woman in a “victorious stance” and the rear half of a horse. Campaigning for next year’s awards, however, has been put on hold in favor of a new adventure. He’s taking a passion for sustainable giving on the road with a cross-country cycling tour this summer.

This spring, Tyler quit his job at local e-commerce agency Classy Llama to embark on the adventure of a lifetime. He is currently crossing the country on a cycling tour along with friends Dakota Graff and Giancarlo Ospina. Their goal? To raise $50,000 for local nonprofit I Pour Life’s 10x10 program. The program benefits women in the impoverished community of Korah, Ethiopia. The team departed from New York City in May and is planning on arriving in Seattle in early August—a journey of about 3,500 miles. All personal expenses during the trip are funded by business sponsors, so the entirety of individual donations go directly to the women in Korah. What does it take to traverse the country by bicycle? In Tyler’s case, it takes a little training and a great sense of humor.

417 Magazine: Have you always been a giver?

Jesse Tyler: I’ve always been interested in the idea of moving toward social business: the idea of business that could give back. I started a T-shirt company my senior year of high school in 2012, and I brought that with me when I first moved [to Springfield]. It was called Take Heart Apparel, and it’s something I started to give to different nonprofits. [Editor’s note: Tyler closed Take Heart in April 2016.] Twenty percent from everything we sold went to different missions organizations. I never actually took any money from that. It was always solely for the purpose of giving to these causes. 


417: What do you hope to get out of this ride?

J.T.: It’s an exercise in, “What am I capable of? What’s the most I can do physically and mentally?” I like the challenge of it. But really, we’re mostly geared by the actual giving. Take Heart Apparel, for example—I did that for the past three, almost four years, and we were able to give a few thousand dollars every year, which is pretty amazing. But by doing this ride, we’re able to give $50,000 in the course of three months. So if I’m comparing those things, I have this amazing opportunity to get a really huge return on the investment of my time and skills. So I’m excited about it in a practical sort of way, but I’m excited about the adventure side of it, too. I do really look forward to traveling, seeing the country, meeting people. But, as cliche as it might sound, the giving aspect is the biggest motivation and the thing I’m most excited about.


417: Are you nervous to take on such a big ride?

J.T.: Definitely. There are so many different things that could go wrong. It’s nice to be in this technology age where, at any given moment, I can Google my location, and Google will tell me where to go and how long it’ll take. But, at the same time, you’re so concerned about getting mauled by a timber wolf or a grizzly bear. I think I might be the first, but I know it’s possible, so I don’t rule it out. 


417: How is this ride tied to I Pour Life?

J.T.: I Pour Life is a local nonprofit with initiatives here in Springfield, in El Salvador and in Ethiopia. I got connected with I Pour Life through Take Heart, and connected Take Heart to their local initiative. So when we were preparing for this ride, we were considering what causes we wanted to give to. Giancarlo had actually gone to Ethiopia with I Pour Life, and he got to see their 10x10 program firsthand. It was on his recommendation that we would give to the 10x10 program and to the women in Korah. The 10x10 program is a sustainability-focused program, and it’s women-led. It’s a family empowerment program. It targets women who are suffering from leprosy and at risk of losing their children. The program focuses on 10 women with leprosy at a time. In 10 months, it teaches them a trade and supports them with the medical treatment and the loans they need to launch their own businesses. So the way it works for us, it’s $1,000 per woman, and when donations come in to us, 100 percent of it goes into the field. We’re trying to sponsor 50 women, so $50,000 is our goal.

“As cliche as it might sound, the giving aspect is the biggest motivation and the thing I’m most excited about.” —Jesse Tyler

417: Tell us about your devastating loss of the “Best Person to Invite to a Party” title. 

J.T.: I was looking through the [Best of 417 voting] list, and there are dozens and dozens of different categories. One of them was “Best Person to Invite to a Party.” I thought to myself, “That’s hilarious.” I was like, “I’m gonna ask everyone I work with and all of my Twitter followers and Facebook friends to vote for me.” So I posted on Twitter, posted on Facebook. I let ’em know, if you’ve been to a party with me, you know that I’m a pretty good person to invite to a party. I’m a good time. Just throw my name in there. And I didn’t think anything would come of it. But then I made it to the finals and I was actually serious. It suddenly went from this joke to, like, man, I really want to win this thing. I was pretty fixated on the idea of my name being published somewhere with the words, “Best Person to Invite to a Party” next to it. It became really the most important thing in my life. It was all I wanted. This was it. The pinnacle of my existence.


417: What qualifies you for this distinction?

J.T.: My constituents would be the ones most qualified to answer that, but I could name a few things. I bring a lot of positive energy. There’s always a surprise. You get me in a room with a bunch of people, you know, anything could happen once I’m there. 


417: When you didn’t win, a friend made a Kickstarter to get you a trophy. Was there an incentive for donating to the Kickstarter campaign?

J.T.: I made selfie mugs over the past year. As a joke, I took a selfie and put it on a mug. And then I took a picture of me holding that mug. Then I sold the mug, and then, with that money, bought another mug. I went 13 mugs deep. If you donated $15, you would get a mug with a photo of me holding the last mug and my trophy.


417: How are you prepping for 2017’s campaign?

J.T.: The first part of it is getting invited to more parties. I don’t get invited to a tremendous amount of parties, and I think that’s what might have hurt me. There weren’t enough people who really saw what a good party attendee I am. I’m using my position as Fourth or Fifth Best Person to Invite to a Party in all of 417-land as a platform. I needed to get my name in the mix. It’s become, I guess you could say, a household name in the 417 region. So that when someone’s making their party list, they see my name and they consider adding me. I’m also trying to get invited to more weddings. One thing that I’ve considered is setting up a few more friends, maybe setting up some blind dates so I have a few more weddings to look forward to. That’s really the ultimate party if we’re being honest. The free food, the free beer. I mean, you really can’t beat it. And that’s where I shine, at weddings.


417: How long have you been preparing for the ride?

J.T.: I bought my first road bike last summer. So I’ve been cycling for about a year and have never been a serious cyclist. I just casually ride. I ride with friends, ride to work every now and again, but have never done any kind of touring. I wouldn’t even say cycling is a part of my identity. So the ride was more of something that was achievable, and it seemed like it’d be a fun idea. It didn’t come from me being really passionate about cycling.


417: Tell me about your team.

J.T.: I’m riding with Dakota Graff, who is a barista at The Coffee Ethic, and Giancarlo Ospina, who is a student and also works for I Pour Life. 


417: Would you say they’re your best buds? 

J.T.: Yes, definitely. I met Giancarlo when I first moved to Missouri. He was a fellow student, and he became my business partner for Take Heart. For the past two years we’ve been doing Take Heart together, and we do pretty much everything together. And Dakota was one of our friends; we knew him from hanging out at local coffee shops and had many mutual friends. We knew he loved cycling and is a great photographer and writer. We thought he would be a great addition to our trip. He brings a lot of experience and knowledge where we lack it.


417: Are you training or preparing for the trek in any way?

J.T.: Not as much as we should, but we’re pretty much transitioning to almost exclusively riding our bikes. I try to park my car and ride my bike wherever I can. And then on weekends we like to go on bike-camping trips where we’ll go maybe 50 miles in one direction, camp somewhere, and then go 50 miles back.


417: Where did the idea of a charitable cross-country cycling tour come from?

J.T.: We like traveling. We like seeing new places, going camping. When I first started using a road bike often, I thought it would be really cool to do a touring ride. We follow a lot of people who do that sort of thing, and we really liked the idea of doing camping and travelling, but the means of a bike brings this level of physical exertion and the slow pace in which you get to see things. So we were really drawn to the idea of doing a cycling tour to get kind of an adventure.


417: Are you planning a trip to Ethiopia to visit the women you’ve helped?

J.T.: I hope so. I’ve wanted to go, but it’s hard for me to justify it, to say, “Is it better for me to pay for the flight and go and travel, or is it better just to give that money?” And I think, after the ride, it will make a little bit more sense to go and kind of wrap up the campaign. But I really do hope to be able to go and be able to meet the women that we’ve helped to support. I think that would be probably one of the most special things in my life if I get to go and meet the women that we are able to sponsor and to help.


417: When you didn’t win in the Best of 417 contest, a friend made a Kickstarter to help you get a trophy. Tell me about that.

J.T.: I had met for coffee with one of my friends after I knew that I was in the top five. I was telling him about the big competition and my hopes to win. And I was telling him that I thought it’d be really fun, if I got between first and third place, that I would get myself a trophy. And this would be the biggest surprise that I had ever brought to any party. I would buy myself a trophy and say that it had come from 417 Magazine. And I would bring it around to the big party for the winners—I don’t know if there is a party, I didn’t get invited. And people would say, “Oh, where’d you get the trophy?” And I’d say, “Oh, you didn’t get one?” And I’d flaunt this trophy everywhere I went at the party. Then I told him, “Man, I didn’t get it,” and he built a Kickstarter.


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