“I almost blacked out playing piano for a song with Brandi Carlile. It was during her show on Cayamo, the music cruise. While Brandi and I are friends, I know she doesn’t want some guy coming out and wrecking the momentum of her set. Before we started, Brandi said, ‘Andy, everyone’s on your side. We’re all cheering for you.” She was trying to calm me down.

I had just sold Sixthman–the company that runs Cayamo–and had time on my hands. Why not learn how to play the piano? I asked Brandi the key of her song ‘That Wasn’t Me’ and told her why I was trying to learn it. She replied, ‘I play in A. You’re playing it next year with me on Cayamo, so get ready.’ Terrified, I practiced every day for months. Then it was just Brandi and me on the Cayamo stage. No band to blend in with. Nowhere to hide. We started. For a few seconds, I forgot where we were in the song. Brandi looked at me and smiled, moving close for the rest of the song. We made it through, then Brandi hugged me. It was scary, amazing, and just beautiful. I’ve watched the video of that song so many times, telling my kids to play it at my funeral. I may never have a better life moment than that. I love creating unforgettable experiences for other people, but that one was mine.

I learned about relationship experiences from my stepdad. He was legendary in hotel hospitality, working with some of the country’s nicest hotels. We moved a lot for his job, sometimes staying in the hotel until we found a house. I was 17 when we lived in the Caesars Palace penthouse in Las Vegas for a month. We had room service every night; the hotel dry cleaned our clothes, including underwear and socks. My twin brother and I walked through the casino lobby at seven every morning going to school–passing people gambling, smoking, and drinking. We went to five high schools in three states. It wasn’t fun, but it forced me to be adaptable and make quick connections. I also became entrepreneurial.

In college, I left a bar one night with five bucks. I needed a ride home and was hungry. There was a pizza place around the corner with a $4.99 large pepperoni pizza with delivery. I ordered and rode home with the driver, eating my hot pizza. I was done by the time I got home and gave the rest of the pizza to my roommates.

A few years later, I managed the band, Sister Hazel. My favorite part was building relationships between the band and their fans. Hearing fans’ stories and giving them a chance to meet the band gave me the energy to do the other stuff. We started The Rock Boat cruise in 2001 for a deeper connection with fans. We sold out the cruise in 2005 and were going to make enough profit to keep us in business. I had a baby with a second one on the way. Things were looking good. Then Hurricane Katrina hit. Carnival gave our ship to FEMA, and The Rock Boat was canceled. Carnival refunded our money for the ship, but I had more money obligated to the bands and expenses. There were no investors. This was all on me. For a few days, I thought I was done. 

But our guests started calling, saying ‘keep my money. Just don’t go out of business’. Or ‘This is my favorite week of the year. Please don’t let it stop’. Ten guests ended up loaning us the money to rent the ship the next year. They took a chance and kept us going. That’s when I realized this is more than a cruise or music festival–we’re in the community-building business. 

The Rock Boat expanded into other music cruises and events. Now I have Topeka that creates music vacations. People see us going for impossible things and feel connected to us. Sometimes we get it right–sometimes we don’t. When we don’t, we fight like hell to figure it out. That gives people a chance to get to know us on a deeper level. They see how much heart we have.

When I took a few years off after selling Sixthman, I didn’t just learn piano. I got curious about the challenges and social issues around Atlanta. I met with nonprofits, learning from those doing good work. I’ve mentored social entrepreneurs and worked with families living in public housing –trying to understand the financial, physical, and emotional barriers. It’s finding real solutions to hard problems. I enjoy this as much or more than anything I’ve ever done. And I love what I do.

I used to say on Cayamo that if we all lived in the same town, we would be best friends. Watching people connect is still what brings me joy.”

Andy

Here’s the link of Andy playing with Brandi.