We caught up with the brilliant and insightful Billy Sullivan a few weeks ago and have shared our conversation below.
Billy, thanks for joining us, excited to have you contributing your stories and insights. We’d love to hear the backstory behind a risk you’ve taken – whether big or small, walk us through what it was like and how it ultimately turned out.
A recent risk that I took was taking a 6 week long cross country trip across the United States on shoestring budget ($1700) to busk in different cities/towns and explore the country. As a 20 year old musician pretty early in my career and limited in my travel/life experience I thought it might be a really cool opportunity to try out. I took my 2003 Toyota forerunner as my vehicle and home, took the seats out of the back, put a mattress in for sleeping, and I got myself a planet fitness membership for the showers.
As some background leading up to the trip, I had taken a smaller 2 week trip last year down to Nashville with the same setup to busk on the streets, and after that experience I found myself wanting more. I wanted to see what it was like out west as an east coast guy who’s never seen real crazy scenery.
My general philosophy that’s drawn me towards these adventures has been one of the value of risk taking. After really considering the fact that I am going to die, it makes me want to take all the risks I can and live life to it’s full potential. I know when it comes to my life, even if something is hard and there’s a high chance of failure, I will almost always regret the risks that I didn’t take and not the ones that I did. Better to fail in spectacular fashion than to succeed in cowardice. So with that idea in mind I decided I wanted to explore and make some music along the way.
So to begin, on day one of my journey, April 21st, my first stop was a visit at my buddie’s house in Norfolk Virginia a good 5 hours south. This was a great first stop as I was feeling really emotional just before leaving, so getting to hang out with a good friend for a day was just what I needed to start things off right.
After that, day 2, I headed off to check out Chapel Hill North Carolina with the intention of busking. After doing some research it seemed like this might be a good spot to busk, it’s a college town and there is a bluegrass and folk scene in the city (styles I’m very well versed in), and good night life. Long story short, it sucked for busking. It’s kind of interesting because before I got my equipment and guitar out to busk I scouted the area on foot (something I always do with new locations I play in to get a feel of the area and find a good spot to play), and the one thing that was striking to me is that no one would look me in the eye when crossing paths on the sidewalk. It was actually a bit uncanny. It was all college aged students, so maybe it’s just a young person thing and I’m out of touch, but I found it to be really unfriendly and closed off. It was quite weird, and that’s saying something coming from a New Jersey resident where people are known to be quite rude and unfriendly. I found a street corner with a lot of foot traffic, played for a good 3.5-4 hours and made 13 bucks. So the next day I decided it was time to move on.
Next stop, Asheville North Carolina. Now once I got into Asheville it took me about a day to settle in and force myself to get out and busk (it was at this point, the first big wave of laziness hit me), but once I did busk I was glad that I did. It was a great place to play bluegrass and country as the folks out there loved it.
After spending a good 2-3 days in Asheville busking and hiking some good mountains and trails, I decided it was time to move on, but before I left, I decided to go to a bluegrass jam at a local bar advertised online. Now this jam was really cool, there were only three other dudes who went to it, we got to play on a little stage, and these guys were super-pickers. The only thing that was less than ideal is they were very cliquey and a bit unfriendly. It’s weird because that’s been my vibe of North Carolina, a general unfriendliness that’s hard for me to put my finger on. Maybe they can tell I’m a northerner. Anyways it was a pretty good time.
Next stop, Nashville Tennessee. So remember when I mentioned I took a trip to Nashville last year? Well on that trip I actually met a really talented singer, and we ended up busking together. It took me several attempts to get her out to go busking as she would agree and then blow me off with an excuse last minute, which was really annoying, but once I did convince her to busk it was a great experience. Anyways, I had called her a couple weeks before this current trip to let her know I would be in Nashville and she told me to let her know when I would be around so we can busk. My expectations where definitely set low knowing that she is a super unreliable person, but I still gave her a phone call when I got into Nashville and she hit the hang up button before even letting it ring out. I knew she was an inconsiderate and unreliable person, but that just put me in a real sour mood. I decided, well I’ll just busk anyway. It turned out that I wasn’t really feeling it. It was extremely crowded as usual (which is generally good for busking), but on broad Street there were three other buskers, and the cheapest parking I could find was 20 dollars. So between getting blown off by the girl, all the competing buskers, and the 20 dollar parking I decided I’m just gonna move on.
So that night, I settle into my favorite place to sleep, the wonderful TA Travel Center parking lot and I ponder where I want to travel to next. I look at the map of Missouri and finally settle in on Jefferson City. I knew nothing about the city, it was just a random place that I decided I would go.
So after driving through Kentucky and a piece of Illinois and getting some beautiful scenery of the Ozark mountains, I arrived in Jefferson City. The first night I was a little tired from driving and the weather was overcast so I decided I would do some Uber Eats and Doordash driving to make a couple of bucks and settle in. I’m glad that I did because it was an experience. The first delivery I picked up gave me a very warm impression of the state. Right away people where chatting me up with a smile on their face which was really cool coming off the unfriendliness of North Carolina.
One of the coolest people I met that night was a customer at Taco Bell as I was waiting for my food. Right off the bat he asked me “how are you doing tonight?” and I told him that I was doing well, just Door Dashing. He then went on to tell me he used to do some delivery driving for a chemical company before his “ego death”. Now once I heard that I was immediately intrigued so I asked him to elaborate. He went on to say that when he was in the Air Force at 28 years old he got into an accident where he lost a portion of the front left part of his brain. Now the left side of your brain is responsible for things like logic, planning and organizing and the right side is responsible for things like creativity, intuition and emotional intelligence. So this was really interesting to learn about that guy, and it made sense that he was right brain dominant since he has was really social and had extremely positive energy to him. He went on to tell me that right after the accident he lost 5 years of recent memory, so even though he was 28, it was like be 23 again. Another interesting thing is he became really suggestible after the accident and ended up working some bad jobs and being taking advantage of. He said even 5 years later, he’s still in the process of remapping his brain, but he’s better about that now. He said he’ll also get really obsessive interests and study certain topics like chemical engineering or steamboats for days at time. It was a fascinating encounter and I felt like I was best friends with this guy, even though he was a stranger and we only talked for 5 minutes. It’s amazing to me how intelligent and well spoken he was given he was missing a part of his brain. I do kind of wish we exchanged phone numbers because I would love to hear more about his story, but I’m happy with the with the encounter that I did have.
Missouri went on to have plenty more positive encounters as I did deliveries for the second day as it was also rainy. Everyone seemed to be really open to me, and would share alot about themselves which was super charming and friendly.
Around day 3 is where things get sort of interesting. This is when I decided to do some busking in town. So in the center of town I started setting up in front of an art shop. It was a Monday so the shop wasn’t open; and before I even played my first note an 82 year old lady came up and expressed tons of gratitude that I was going to be playing music. She then went on to tip me 20 dollars and asked if I had had supper yet. I told her no and she said she would get me some. About 10 minutes later she comes back with spud and midwest sandwich I forget the name of, so I sit down on the bench to eat and she told me about her religion, how she was a Christian and how that has helped her in life and I told her about my cross country trip.
After chatting with her for a little bit, she asked if I would like a Bible and I said yes. So she goes to Hobby Lobby and comes back 15 minutes later with a Bible and highlights two sections that are really good for young men who want to be successful. So I think I just met the sweetest old lady in the country. Super kind and considerate, so that was a great experience.
Now in our conversation she asked me if I knew the art store owner Jim. I told her no and she said he is a super nice guy who’s also a musician and a Christian. Keep that in the back of your mind because Jim comes into this story a little later.
So that night that I played was overwhelming positive. Tons of people voiced their gratitude and tipped generously. Later, around 8 pm I was talking with this homeless man I had met and befriended and he asked me if I knew any Grateful Dead songs. I told him “yeah, I’ll play ya Friend of The Devil!” So I’m playing this song, and about halfway through, the art store’s speakers that face the road where I am start blasting pop music to drown me out.
This forced me to stop playing because presumably Jim has decided to drown my music out. The music was so loud that the speakers were literally distorted. So at this point I was pretty agitated and just decided to pack up my stuff. On my way back to my car a business owner asked me if would like to play a gig on his patio which I was thrilled to be offered, so that was a bit of silver lining to the inconsiderate end of my night.
The next day I decided that I wanted to busk at the same spot again, and if I wanted to do that I would have to confront Jim. So I walked into the art store and spoke to Jim. I told him that I was playing music on the sidewalk the night before and someone blasted the art store speakers and that I would like to have a chat with whoever did that. Now to my surprise Jim responded with this: “Oh someone must’ve hacked into my speaker system… Ya know people can hack into Bluetooth speakers and garages, it happens”. I knew he was full of shit and so did he, but there was nothing I could really do at that point. I just said that who ever did that was super inconsiderate and disrespectful. We then argued lightly over who owns the sidewalk and it didn’t really go anywhere. There was not much more to discuss after that and I left feeling a little unsatisfied. I think I solved the problem though because that night I busked directly across the street, and no speakers where blasted, so he must’ve got the message. Overall though I was proud of myself that I confronted him. It was a character building opportunity to learn how to confront someone respectfully. It wasn’t an easy thing to do, but it solved the problem.
So after a great second night of busking, I decided to move on to my next location, Lincoln Nebraska. To put it simply. Lincoln was awesome. I busked in the Haymarket section and had some of my most profitable nights at $260 on my best. I met another John Hartford fan when I was playing “In Tall Buildings”, which never happens, as bluegrass musicians aren’t well known among the general public, so that was really cool. One random sort of weird and funny encounter I had when playing was with a woman who was drunk that enjoyed the music. She initially came over and tipped $5 staying and listening, and then snatched the mic in the middle of my song and screamed “USA, YEAH!!” Before walking off. It was pretty rude, but at least she tipped. Then about 5 minutes later, I saw dollar bills falling from the sky, and everyone who caught them were putting them in my bucket. In confusion I looked up and on top of the building was that girl who screamed in to my mic throwing tons of money to me. She requested a song I didn’t know and then yelled “TRUMP 2024!” before throwing a bunch more money off the building to me. Pretty bizarre, but I guess I have no complaints since she was tipping very generously.
The next leg of the trip is to Colorado and unfortunately starts the most disappointing part yet.The disappointing thing about Colorado is that 2 friends that I had planned to meet up with had bailed on me. I planned to meet up with a family member and she ended up bailing as well and I got sick on top of that. I had fun hiking and exploring though. It was too cold to busk but a good time.
After that I hit Moab, Utah and Sedona, Arizona. Both of which were super pretty. Sedona had some good busking so I stayed for a few days.
Next stop was San Diego California. Now California was one of my least favorite states I visited. Very empty on the eastern side (which I like) but extremely crowded and congested at the coast. Gas was $5.50, the drivers were worse than New Jersey and it had tons of junkies and homeless. The first place I busked was the Pacific Beach boardwalk in San Diego. This was a pretty good spot with lots of foot traffic. Now when I set up I was parallel to the ocean with my speaker facing down the boardwalk, and across from me were some hotels with balconies. So about 30 minutes into my set I hear from one of the hotels balconies, “GO HOME!! PRACTICE AT HOME!!” I just ignored it. I know that’s the best way to handle hecklers. The story gets crazier though, because a couple hours later when I was in the middle of playing a song the dude from the balcony got right in my fave and started screaming at me. He started with “I PAY 500 DOLLARS A NIGHT TO STAY IN MY HOTEL AND I’VE BEEN HEARING YOU PLAY FOR 3 HOURS!!! GO HOME!! WHO’S EVEN LISTENING TO YOU? WHERE’S YOUR VENDOR’S PERMIT? WHAT ARE YOU DOING?” Now with this level of hostility it’s a shock I didn’t punch this guy in the face, especially considering he was trying to intimidate me by getting in my personal space; but somehow I channel my inner stoic, stayed calm and repeatedly said, “I’ll talk to you after the song, get out of my personal space.” What’s funny is that other people on the boardwalk during this whole encounter were very supportive of me and started complimenting my playing and tipping 5s and 10s while this crazy jerk was in my face. An amusing contrast. Eventually I just started singing because the guy wasn’t moving and that seemed to do the trick. So he stormed off angrily saying he was gonna call the cops. I wasn’t doing anything illegal so I was happy for him to get out of my hair.
That night ended pretty smoothly with a fun overall time. That night though when I was sleeping in my car in a travel center someone opened my door and stole my wallet. I won’t give you all the details but long story short the problem got solved but it was a bit of a nightmare. Next, I hit Santa Barbara to busk and that went well, I busked in Santa Fe, New Mexico which was great aside from some older buskers who tried to drive me out of town. I breezed through Texas, Oklahoma and Arkansas having some of my first sleepless nights from brutal humidity and buggy air, stopped along the Gulf of Mexico in Florida to relax for a few days before visiting my brother in Atlanta, Georgia. My last and final stop was the Blue Ridge Guitar Camp in Brevard North Carolina which was a really nice way to end my journey.
Overall, I took the risk of going on a long cross country trip completely self sufficient. It really sucked at some points, but overall it made me a tougher and more resilient person.
Billy, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?
I am a musician who plays various genres such as bluegrass, folk and rock music. My story is pretty simple, my dad taught me how to play guitar when I was 9, and I’ve been exploring ever since. I am most proud of my skills as a lead guitarist and my song writing. As for the music industry, I’m still figuring out how to get consistent gigs so I don’t know if I’m fully qualified to speak on that aspect. I’ve played a good amount of gigs, but I’m still working on making it full time.
Is there a particular goal or mission driving your creative journey?
If I could summarize the goal and mission of my creative journey in one word, it would be authenticity. Playing guitar and writing songs seem to be the best outlet for me to express myself. The goal of life is really just a push towards authenticity and finding yourself.
Are there any books, videos or other content that you feel have meaningfully impacted your thinking?
Meditations by Marcus Aurelius and lots of general youtube videos on the philosophy of stoicism. Learning about this one philosophy completely changed my life and liberated me in the sense that it helped me realize that other people’s opinions should not dictate my own confidence in myself. As a sensitive person, I’ve always been really angered and hurt to extreme levels when other people have rejected, disrespected or disapproved of me. My school experience was one ripe with getting bullied and generally not fitting in. Now these things used to upset me and I used to want to get acceptance and approval from others, but after taking stoicism to heart I can really accept myself for who I am and appreciate myself based on my good qualities and virtues, not what other people think of me.
This philosophy really extends to making music as well. As a musician, if you care too much about what other people think, you might just give up the dream entirely and not even try to share your art out of the fear of criticism. But if you realize that your art has value on its own and that other people’s opinions are irrelevant, it liberates you to truly and authentically express yourself. As an artist you are always going to encounter haters and naysayers, so having this safety blanket of stoicism to keep you grounded in reason, logic, virtue and truth is extremely helpful.
Contact Info:
- Youtube: https://youtube.com/@bluegrassbilly?si=4ySKQLWGitKLc91m
- Other: https://open.spotify.com/artist/1mHoeFAB4p392ItqeSmsLn?si=Q-WMpxR8T_mVwg2gfCP_8w
