September 2011

CH2's Bachelors of the Year ALUMNI: A Q&A With The Guys Who Took The Title

Author: Special To C2 Magazine

In remembering some of the fonder moments of the last few years at CH2, we would be remiss not to mention the Bachelor of the Year contest. It was, after all, the shameless exploitation of these good-hearted young men that put CH2 on the map. But just so you don’t think we are completely self-serving and evil, it also enabled us to write a big check to the Island Recreation Center every year.

We decided to catch up with the guys who took the title to see what they were up to and find out if winning The Bachelor of the Year Contest had any long-term negative effects on their psyche.


BEN WOLFE: Bachelor of 2011
Photography by Mark Staff

Has some lucky lady tied you down or are you still hanging onto the Bachelor title?
I’m presently still hanging on to the title, but I did finally take off the sash after I got wicked tan lines this summer.

Are you still on Hilton Head Island?
Sure am!

What are you up to these days?
Working as the Director of Performing Arts at Hilton Head Prep…..and planking.

What’s the strangest thing that happened to you as a result of winning the Bachelor of Year contest?
When the magazine was out, I would have people stop me in the grocery store and say: “Where do I know you from?” Then, I’d turn, give them puppy eyes and say: “Mommy?”

Any words of advice for this year’s contestants, for example, tips on how to win?
Be yourself, have fun, and don’t sound like a tool on the videos.


TROY AHYO: Bachelor of 2010
Photography by Mark Staff

Has some lucky lady tied you down or are you still hanging onto the Bachelor title?
No. Still a bachelor. Perhaps this year?

Are you still on Hilton Head Island?
Yes. I love the island, my friends and so many great people that live here.

What are you up to these days?
I still work in the online world. I am consulting with a couple of start-ups and doing marketing for a select group of companies. I started kiteboarding almost a year ago and I am obsessed. If there is wind, I am out. Besides that, I spend time with my friends enjoying what HHI has to offer.

What’s the strangest thing that happened to you as a result of winning the Bachelor of Year contest?
Hmmmm. Strangest thing? I can’t really think of anything strange. But the best thing about winning was all of the great people I met and of course, all the great exposure of being in CH2. It was fun for awhile when people that I did not know, would come up to me and say they recognized me.

Any words of advice for this year’s contestants, for example, tips on how to win?
My advice is to make winning a full time job for one week. Recruit a few team leaders who have large circles of influence and have them push hard to get people to vote. You have to ask most people at least five times to vote before they actually do. My family and a few select friends championed my campaign and never gave up until the contest was over. Don’t expect a couple of posts on Facebook to win you many votes. You have to work a lot harder than that.


JACOB RAEHN: Bachelor of 2009
Photography by Anne

Has some lucky lady tied you down or are you still hanging onto the Bachelor title?
No one has tied me down yet, but maybe, just maybe, I’m finally getting to the point where that would be alright.

Are you still on Hilton Head Island?
Unfortunately no. I am living in Columbia South Carolina, but still return to the Island as much as possible because it will always be home to me. In addition, Columbia is HOT. Famously so apparently. So ya’ll had better enjoy every minute of that ocean breeze!

What are you up to these days?
I just started my second year of law school at the University of South Carolina School of Law. This kind of further explains my answer to question number one. I’m a student again, with very little free time to call my own and mountains of homework. I spent this past summer working for a law firm in Columbia, and now I’m repping on campus for one of the textbook publishing companies. My Hilton Head life of leisure has really digressed since 2009.

What’s the strangest thing that happened to you as a result of winning the Bachelor of Year contest?
I was pretty good about keeping the “former bachelor” title under wraps when I moved up to Columbia for school a year ago. The whole, new people, new identity, fly under the radar, etc. And I did a pretty good job for a while… Until my Contracts professor this past spring found out and wrote about the Bachelor competition in one of her hypothetical problems for class. I was doing the problems an hour before class started, and low and behold I got to number three and I knew I was done for. Class started an hour later and sure enough she called on me to answer number three and my class of 80 students got a real good laugh. So maybe not the strangest thing, but definitely the most embarrassing since it’s a little hard to answer questions about “hypothetical cover” and “partial performance” when there’s an entire room of people laughing at you.

Any words of advice for this year’s contestants, for example, tips on how to win?
At some point during this competition Maggie Washo is going to embarrass the mess out of you. You’ll know the exact moment I’m talking about when she asks you to put food coloring in your hair, wear an apron while holding a feather duster, or is shaming you into wearing an Austin Powers costume. Roll with the punches and it will be one of the best times you’ll ever have. As far as winning, use your parents, siblings, and their friends, because they are the ones that get really excited about your chances to win and will spread the word like wild fire.


CHRIS WELLS: Bachelor of 2008
Photography by John Brackett

Has some lucky lady tied you down or are you still hanging onto the Bachelor title? I’ve been in a relationship since January and things are going well. I think I’m the lucky one. She’s pretty awesome.

Are you still on Hilton Head Island? Yes, 14 years and counting.

What are you up to these days? Working hard and always looking forward to that next vacation.

What’s the strangest thing that happened to you as a result of winning the Bachelor of Year contest?
Being recognized as the B.O.Y. was just weird for me. To this day, I find it strange when someone comes up to me and asks…. “Hey, aren’t you that guy? You know, the Bachelor of the Year.”

Any words of advice for this year’s contestants, for example, tips on how to win?
I still don’t know how I won so I’m not sure I have any words of wisdom on how to win. I know my friends and family had fun w/ the process and I’m sure behind the scenes they were pretty viral w/ everything. I’ve got some great friends and they just ran with it.

Advice: Have fun w/ it and don’t take it too seriously.


JIMMY LEPPERT: Bachelor of 2007
Photography by John Brackett

Has some lucky lady tied you down or are you still hanging onto the Bachelor title? Actually, just this past weekend, my girlfriend and I moved in together. We’ve been dating for six months and I am having the time of my life- she is brilliant, stunningly beautiful, athletic, and has a great sense of humor. I am a better man with her in my life.

Are you still on Hilton Head Island?
I’m a New Englander now- living in Cambridge, Massachusetts.

What are you up to these days?
In terms of work, my passion is in building the capacity of individuals and teams to learn at a rate that enables consistent and ground breaking innovations- particularly across traditional disparate boundaries in organizations and sectors.

I work out of three organizations: the Academy for Systemic Change- a start up project taking effective systemic change efforts to scale, Massachusetts Institute of Technology’s (MIT) Sloan School of Management where I am a Research Affiliate, and the Society for Organizational Learning a non-profit global network of practitioners and researchers.

What’s the strangest thing that happened to you as a result of winning the Bachelor of Year contest?
Being recognized in a small town in Virginia as the bachelor of the year.

Any words of advice for this year’s contestants, for example, tips on how to win?
Relax and have a great time.

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