Billy Reilly, The Fastest Bartender…Winning (and Working) at Life
By Lori Welch Brown
Billy Reilly, The Fastest Bartender…Winning (and Working) at Life
I thought I had a strong work ethic, but this month’s Personality Profile, Billy Reilly, is making me rethink my game. After an hour phone call, I felt like I had been bowled over by the world’s fastest bartender (which by the way, he has held that title) not to mention most gregarious Irishman in the DMV. As a self-proclaimed Army brat, Billy lived in 22 different states (as well as one foreign country) before his dad settled the family in Virginia back in 1969. After college, like many new grads, he started bartending and realized he was not only good at it, he was GREAT at it. I won’t say what year, but let’s just say he was a bartender before mixology was a thing. His first gig was at Kilroy’s in Springfield (he thanks the Thomas family for his start there). He went on to work at many of the area’s hottest establishments. For those of you looking for a throwback moment—think Lulus, Samantha’s, Champions, and Ha’Penny Lion. He had his foot in both the DC & VA markets and fondly remembers DC in its ‘wild west’ days. For Billy, bartending was his sanctuary, his safe space. “When I got behind the bar, I had to leave all my crap at the door. I became everything to everybody—psychologist, entertainer, friend, etc.—it was about them, not me.” One of Billy’s working credos was to work until they no longer had to introduce themselves—reminiscent of that famous Bostonian bar, Cheers, a place where everyone knows your name and they’re always glad you came.
A game changer happened for Billy in 1992 when he flew out to Vegas to join 900 other bartenders in a worldwide bartending competition where he took first prize for fastest bartender and second place overall. Things exploded for him as the event got worldwide coverage—all of the sudden he was the industry ‘go to guy’ for radio shows, interviews, etc. In 1995 he entered and won the Fastest Bartender contest, and in 1999 bought the organization that ran the competition. He expanded it across 11 states before selling it in 2013. BREAKING NEWS—Billy and his new business partner, Chris ‘Diddy’ Hollowell are the new owners of the Fastest Bartender contest with the goal of taking it national. “I’m feeling it. It’s my time and I couldn’t be more excited to be back,” says Billy.
If you’re thinking this guy is legendary, here’s further proof—he’s been in the Guinness World Book of Records—twice! First for completing the longest bar shift (240 hours). The feat was pulled off at Champions in Georgetown and raised $25k for a local charity. The night ended with friends, family, and cheering fans carrying him out on their shoulders. “That was my most memorable night—I was at the height of my craft.” His second record breaking stint was longest shift on a rooftop which he maintained for 14 consecutive days and raised over $26k.
Slinging drinks was his night gig, and during the day, he was Sales and Marketing Director for a couple of the area’s biggest beer distributors. He quickly grew a reputation for being the ‘go to guy’ for organizations looking to grow their business which ties into one of the companies he spearheads today—Shamrock Solutions. He is the ‘go to guy’ for small-medium size companies looking to expand their market. “If you can create a memory, you can create a business, and that’s what I help people do. Whether or not people like me, they know I’m the guy who gets stuff done and that makes me very happy,” says Billy. Friend and client, John Wood, owner of the historical 29 Diner in Fairfax happily agrees, “Billy is a chaser of the American dream. He is up before you, will work harder than you and opens doors everywhere he goes. People want and need him around when they want a loud, booming voice for their cause, product, brand or event. He has a vision and will create the buzz, the circus-type atmosphere needed to get your business seen.” Bar icon, friend, and Union Street General Manager, Al Chadsey, refers to Billy as the closest thing to P.T. Barnum he has ever seen. “When Billy gets behind something, he is the ultimate promoter.”
Words like goals, respect, hard work, and pride roll off of Billy’s tongue—they’re not just interview speak. It is evident they are part of his daily vernacular. Clearly he is a very disciplined guy (three black belts, btw), and at 55 years old, feels he is at the highest point of his game. To say he is excited for this next chapter is an understatement. He boasts 6,000 bartenders among his contacts and friends—many of whom contact him on a regular basis for advice or just to catch up. He is proud of his bartending community. If you were to ask Billy what he does for a living, you’d likely get an answer like “I shake hands. From the bar back to the owner, everyone is important and I love them all.”

All records and titles aside, he is most proud of his two teenage sons. “I didn’t do everything right, but I do everything for them,” says Billy. “I can’t teach them ambition/drive, but I can create a template of things to do right.” His crowning glory was the day the lightbulb went off for his 17 year old who realized why dad enters every establishment through the back door, “You never stand in line anywhere, Dad. Everyone knows you.” He doesn’t stand in lines or pay cover charges and gets tickets to any event he wants from BBQ to black tie. Billy has spent his life fostering those kinds of relationships. “I wake up every day asking myself the same question. Who can I help today?” Billy was the first person John called when he landed the deal to purchase 29 Diner. “Billy is larger than life—he is a personality that everyone knows and he has a relationship with everyone he knows.”
In the spirit of St. Patrick’s Day, let us not forget that Billy is very proud of his Irish heritage. “He thinks he is half Leprechaun,” laughs Al. Where will you find this larger than life force-of-nature Irishman on St. Pat’s Day? Sitting at his favorite pub when they open at 7:00 a.m. to toss back a shot of Jameson and raise a Guinness in honor of his biggest fan, his grandfather, William Francis Reilly. “My grandfather taught me if you wake up today, give thanks to God. And, if you made it through the day and back into your bed, you give thanks. What you do in between, however, is up to you. I’ve always taken that to heart,” says Billy. “In my world, there is no second place. I’m okay with someone beating me, but it means I was outworked, and I’m not okay with that. I’ll figure it out and try harder next time.” For Billy, it’s not about winning a competition (although he has been there, done that), it’s about winning at life.
After he honors his grandfather, he’ll join a group of 30-40 of his closest friends to spread some Irish cheer, and there will likely be some singing involved. “March 18th is always a rough day,” laughs Billy.
Thank you for the terrific article about my long time friend Billy. He’s always had it in 5th gear and I doubt that’ll stop anytime soon.