Taylor Watson: Why Impromptu Car Performances Can Launch A Legendary Music Career

As a part of our interview series with leaders, stars, and rising stars in the music industry, we had the distinct pleasure of interviewing Taylor Watson.

Taylor Watson is an American singer-songwriter and social media star with over 2 billion views on her social media platforms. Her signature pop music is blended with sharp-witted hooks, sticky melodies, and unapologetic attitude. In 2021, Taylor began working on her debut EP with a number of heavy-hitter producers including GRAMMY® winners Rami Yacoub (Ariana Grande, Britney Spears, Demi Lovato) and Skylar Mones (Dua Lipa, Kesha, Carlie Hanson). Her latest single is “Not My Type,” produced by The 87’s (Iggy Azalea, Steve Aoki). Oozing danceable synths that underscore a fresh perspective on love, “I’m so fucking glad you’re not my type” is a tag Taylor penned to encourage listeners to stop romanticizing their “type” of partner if their “type” isn’t a good one. The unconventional love song is surprisingly self-aware, brutally honest, and endearingly romantic all at once. Taylor Watson is a powerful and dynamic new force in music who continues to prove that there’s no one quite like her.

Thank you so much for joining us in this interview series! Before we dive in, our readers would love to learn a bit about your “origin story”. Can you tell us the story of how you grew up?

Of course! My origin story is actually pretty cool — I was an unplanned surprise baby to a 21-year-old single mother from Florida, who was living in Colorado at the time. When she found out she was pregnant, she drove all the way home back to Orlando with her mom (my nana) to go back to school — law school, like Elle Woods before Elle Woods was a thing. On that drive down, the only CD’s they had in the car were James Taylor CD’s in the car — so that’s how I got my name, Taylor. My mom crushed law school, taking me with her a lot of the time, and became an attorney before meeting my dad — well, the man she married who adopted and raised me. So yeah, that means I’m technically half adopted. We moved from Florida to Colorado when they got married, where I grew up with my parents and two younger brothers until I took off to chase music dreams in Nashville.

Can you share a story with us about what brought you to this specific career path?

I was born to sing and make music, I mean literally, I was humming and baby-gibberish singing along to the radio before I started talking. But I guess when I realized this could be a career for me was in high school. I started playing guitar and writing my own songs, and my mom suggested I start busking (playing next to an open guitar case on the street for tips). That was a wildly intimidating thought, so I refused for a while. But I also absolutely hated my mall job, and so one day my mom offered to pay me $50 to go busk for 3 hours in Boulder. It was a guarantee, and so I did it. And not only was I able to draw crowds and make money, I actually really loved it. After that, I didn’t need my mall job or any other job — every weekend I would go play on the streets of Boulder for hours. I was making between $20-$200 an hour at one point, as people would hire me off the street for private events in addition to street tips. I was able to pull the magician’s crowd in after his set, and I started sneaking my songs in with the covers I played to see which of my songs the crowds liked. People started asking where they could get my songs, and that’s what prompted me to become a recording artist.

Can you tell us the most interesting story that happened to you since you began your career?

Oh god, the most interesting? Honestly, I’ve had a really wild career path…so I don’t know if this is the most interesting, but the story of how I met my first producer is a great one. I was 16, and I’d come to Nashville with my dad on one of his business trips to see Music City. While he was in meetings, I’d play my songs for the wives or friends of his business partners. One of them loved my voice and my songs and insisted I meet his friend Paul, the producer. I had no idea Paul was Paul Worley, a multi-Grammy winning producer and executive known for discovering and developing some of the biggest female artists in country music, from The Chicks to Sara Evans and Martina McBride. I was just 16 and excited to meet anyone who could produce my songs. So, we met at this little Greek diner near his office, which was under construction at the time. We talked for a while, and then he asked me if I had any songs recorded that he could hear. Nope. He asked me if we had offices we could go to so he could hear me live. Nope. So he said once I had that, he’d take the time to listen and give me his honest feedback. But I didn’t want to do a back and forth when I had him right in front of me. We had a rental car, so in the dead heat of a Nashville summer, I made him and my dad sit in the front seats of the car while I sat with my guitar and performed for this legendary producer from the backseat. I’ll never forget him watching me in the rearview because he had a crick in his neck, and after each song he’d just say, “do you have another one?” I played him 5 or 6 songs while he just sat and listened, and then told me he wanted to work with me. He told me I had great tone, and songs beyond my years, but I was “green.” He said he’d show me the ropes, help get me with great songwriters to help hone my craft and start producing me when I was ready. That meeting changed my entire life.

It has been said that our mistakes can be our greatest teachers. Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I got the opportunity to audition for The Voice at a producer call in Nashville (basically a smaller group of people invited to audition for producers rather than a cattle call). At the time, I was driving an old Jeep Liberty with a solo broken key (it couldn’t go on a key ring). I had equipment in the back of my Jeep that I was supposed to bring to the studio the next day, but it was cool outside, and I had it covered so I figured it would be okay for a few hours. At one point, while we were all sitting in the hallway, I heard someone yell out, “did anyone lose a Jeep key?” I jumped up, and there was my key, broken key ring hole and all. I threw it in my bag and proceeded to practice and then do my audition. When I left, I couldn’t remember where I parked, so I hit the lock button to find my car and hopped in without checking the back. The next morning, I went out to my car to head to the studio, and…the key wouldn’t work. I was completely locked out and had to call a AAA locksmith, but couldn’t find my AAA card. I had people blowing up my phone about my ETA and the equipment (it was a really bad look) and I didn’t want to admit I’d left the equipment in my car, so I was making excuses and panicking. In a frantic move to find my card, I decided to dump out my entire bag on the counter to see if it had fallen out of my wallet…only to see another Jeep key. The thing is, I didn’t have two Jeep keys. I went outside with the new key and realized I HAD DRIVEN SOMEONE ELSE’S CAR HOME. Someone with a same year, make, and model Jeep — with a broken key — had dropped it, and I had assumed it was mine without checking. I called the venue, and the owners of the Jeep had already called, but thankfully not filed a police report because the only car left in the lot was my identical Jeep. We had to meet up to swap cars and I was able to get the equipment to the studio…but really late. It’s not the deepest lesson, but I guess the moral of the story is either don’t leave equipment in your car; or double check your car if you’re driving home with a lost-and-found key.

What are some of the most interesting or exciting projects you are working on now?

My first full record is pretty much done, and I am so insanely proud of it, it’s my whole world right now. One single is already out (“That Bxtch”) and the next two are scheduled to drop on August 26th (“Not My Type”) and October 14th (“Last Night”). I’m in love with this whole project, and the fact that it’s a full 12-song project makes me so happy. I love the single drops and the EP approach, but I grew up on records. Big, long, records where everybody knew the hits, but real fans knew the deep cuts, too. If I had one hope for this record, it would be to watch that happen. Every track details a different life experience of mine, and so many of them are interwoven that if you can put it together, they tell a really brutally honest story. The next single, “Not My Type”, is a really unconventional love song about my partner and I, so it’s particularly special to me. After that one, “Last Night” is one of my favorite songs I’ve ever written and makes me cry every time I listen to it. While you can listen to that song as a breakup record, it’s actually about seeing someone alive for the last time. That’s why I’m releasing it in October, for Mental Health Awareness Month.

We are very interested in diversity in the entertainment industry. Can you share three reasons with our readers about why you think it’s important to have diversity represented in music, film, and television? How can that potentially affect our culture?

Absolutely, this is something I’m wildly passionate about. One of my brothers is gay, and it made me hyper-sensitive to how the LGBTQ community is represented in media. The lack of representation of gay relationships on TV and the casual bullying of that community for so many years is honestly so damaging. For me, the first and biggest reason we need diversity in the music, film, and TV we create and consume is that these arts are the most widespread and accepted depictions of reality we have, and therefore play a huge role what we perceive as normal and acceptable. Actors, artists, and writers have a way of becoming our cultural sails, steering the ship in one direction or another. We’ve come so far as a society in terms of social equality and acceptance, but we have so much further to go. If we scale back the diversity in our media, I believe that will negatively impact the speed of our social progress as a society. Another huge reason is to inspire and include everyone, so that no one’s dreams feel out of reach. Every kid of every race, sexual orientation, and gender deserves a successful role model to turn to. I’m a straight white female — I had plenty of role models to aspire to, plenty of examples of people “like me” who made it big. But for so many people, for so long, that hasn’t been the case. Women of color had to fight harder for their place in film and TV, and were still paid less. The representation and inclusion of all types is so crucial to create a healthy, accurate depiction of the world where everyone feels necessary because they are necessary. And that plays massively into mental health, as well. Gay kids who don’t feel okay at home should be able to turn to the cultural compass of media and see a world in which they can grow up and not only be included and accepted, but celebrated. That alone is worth it. (I’m giving examples, but of course lots of different minorities can be interchanged into these examples). A third reason, which should be blaringly obvious, is that there simply is diversity in art whether or not it’s acknowledged. And therefore, it has to be acknowledged. Some of the biggest contributors to music, film, and TV are people of color and members of the LGBTQ community. To not give the origins of the arts their fair space on the proverbial stage is simply and honestly just wrong, on every level.

What are your “5 things I wish someone told me when I first started” and why? Please share a story or example for each.

1. “You’re going to write more bad songs than you are good songs. That’s okay. Keep writing.” Ruts and dry spells are part of being a creative. I used to catastrophize dry ruts. To the point I “gave up” on being an artist for literally years thinking I just wasn’t good enough. And then quarantine hit and I wrote like 200 songs with my writing partner. And there are lots of them that aren’t worth a listen. But the ones that are great, are the best stuff I’ve ever written. Sometimes you just have to clear out all the shit to get to the gold.
2. “Everyone wants you to succeed.” That’s a weird one, but true. Artists, writers, and creators who succeed are cash cows to everyone who works with them. Your co-writers want that song you guys wrote to be a massive hit. Managers want an incredible artist, agents want a big booker, labels want you to walk in and blow them away. They are all looking for winning talent, and if you have their ear and their time, don’t think about it any other way. Their job is literally to find and sign the best songs, talent, and entertainers. And the only thing they have to do their job with, is time. So hustle hard to get in front of them, and then get out of your head. They’re hoping you come in and win. You already have a leg up. I made excuses as to why something wasn’t as good as it could be, instead of hyping it up for a win, because I was trying to mitigate doubts that weren’t even there in the first place. They want a winner, show up like a winner and keep hustling until you win.
3. “Keep showing up.” This business weeds out those who can’t take it. Slowly but surely, people give up, move on, or diversify instead of continuing to hone what they’re best at. They fall out of the community; they lose their touch because they get tired or discouraged. It’s okay to be tired or discouraged, but if you don’t show up, you are the nail in your own coffin. Your “class” of competition gets smaller the more you show up when other don’t or can’t. The people who make it are the ones who keep showing up. When I moved to LA to be a music supervisor, my first boss didn’t have a job for me. I kept hitting him up about it every single day until one day he finally let me pitch songs for a project. He told me if one of my songs got picked, I could come in and do the work and get the credit on it. My song got picked, so even though there was “no job for me,” I landed a one-off. After the song was licensed, placed, and credited…I continued to show up at his office every day and work. He looked at me and just said “fine.” Within a month, I was helping run backline and book major talent for a major network show. Because I just kept showing up.
4. “Record with as many people as you can.” Some people say not to record as an artist until you’re ready. In my opinion, finding your sound and vibe as an artist comes from trial and error. You might find that what you like to listen to isn’t actually what you like to write, or that what you’re best at writing you don’t feel is you as an artist and you need to push yourself out of your box. For years, I wrote country and pop country. But I felt like I wanted to sing pop, alt pop, or maybe even indie rock…the covers I enjoyed performing and the music I drove around listening to. It wasn’t until recently I started bouncing around and recording with lots of different producers, instead of just writing and then taking my favorites to a producer. I tried a new approach of being track-led verses acoustic-guitar led, and that’s a huge part of how I got this record and this sound. Prior to this record I worked with a lot of writers, but not a lot of producers. I wish someone had told me to experiment earlier.
5. “Ask for opinions from people you admire and respect, but ultimately, trust yourself.” It’s important to surround yourself with people who have your best interest at heart, experience (and ideally success) in your field, and sound advice. But no one will fight for you harder, guide you more genuinely, or be more true to your journey and destiny than yourself. I’ve had people tell me I needed to be pop country, dress in cut offs and cowboy boots, use pedal steel in my music, and then I’ve had people tell me I need to be more pop, to do something crazy like Katy Perry, to sing in a higher range, sing in a lower range, write happier songs, write sadder songs…I mean the road to success is wide, and people will all have opinions about which road you should take. But ultimately, this is your life, and your career. And the one that rings most true to you is the one you will ultimately pull off best. That’s your true north. Find that first, and then incorporate the opinions of others after to see what best serves your best version of you.

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

If you feel like you’re burning out, diversify in a way that still supports your ultimate dreams and goals. Don’t lose focus, keep on the track as best you can, but find something you’re passionate about that can elevate and coincide with the thing you feel burned out on. For example, if you’re burned out on writing, but the idea of production excites you, start learning to produce…it may be an exciting challenge and change of pace that fires you up again, and it’s something that can elevate your writing. Maybe even inspire new music. If you’re burned out on the politicking and the networking that often goes with being an artist, isolate with some creatives — go to Joshua Tree with a guitar or something and get back to the roots of what got you to where you are already. Appreciate how far you’ve come for a second before you bum out on the work it’ll take to further. Create the next thing you’ll be excited to talk about at one of those stuffy events, and when you’re ready to jump back in, they might even be fun again. If you’re burnt out on trying to be an artist because you’ve suffered rejection, go help other artists with their projects and get inspired, or better yet, jealous. Observe what’s working, let the epiphany that you still want that life too drive you back to your own project. I don’t really encourage “taking a break” entirely from your dream because all we have is time. Sure, spend a couple days on the beach if you’re just looking for a vacation, rest and recharge is valuable. But if you’re burning out on your dream, your dream actually needs your attention, not to be shut out. It’s like a relationship. If you’re burning out on your marriage, don’t run off and have an affair or start a new family somewhere else. Go take a class together or find a way to spice it up, fall back in love, do what you need to do to make it work. Having big dreams is like being married, you have to take care of your relationship with your dream. Find something to supplement it that’s different enough that it feels like a new challenge, a new focus, or getting back to the root of why you wanted that dream, but still supports your end game. I know tons of creatives who get successful, and then depressed, because what made them successful was the creation process (writing the music, being in the studio, etc.) but the leg work of making that product successful is a lot of tedious or challenging work that they don’t love as much as the creation process. For those people, I’ve seen them get fired up just getting back to the creation before they dive into the hustle and grind of making that creation successful.

You are a person of enormous influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

I’m passionate about ending human trafficking by any means possible. O.U.R. Rescue and Free A Girl USA are doing incredible work in this space, and if anything, I would just encourage everyone to put anything they can into bringing awareness, condemnation, and change to this rampant crime. There is so much more we could be doing as a society to work together to protect each other, and until it’s no longer happening, we are no longer doing enough. I don’t know what that movement would look like, but I know I can direct people to organizations who are already making incredible impact and could make even more impact with support from the masses.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I’m grateful to a lot of people who helped get me here, I couldn’t just single one out. Paul Worley gave me my first shot, my first guidance, wisdom, and opportunity. I wouldn’t be where I am without him, period. My parents, who pushed me to busk in Boulder and audition for every solo growing up and who let me move across the country alone at 16 to pursue my dreams…I wouldn’t be here without their trust, love, and support. My boyfriend, and main writing partner, who reignited my love of writing and performing after I’d burned out and nearly given up. He pushed me to embrace my dream instead of being too scared to go after it again. I wouldn’t have made this project or had the confidence to go after a new genre and make this project without his help and support. My producers, cowriters, and A&R friends and family…there are so many people I wouldn’t be here without. I could write an entire article just uplifting the people who led me and encouraged me and believed in me — when I didn’t even believe in myself — to get here, where I am now today.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

You have already won. If you’re alive, talented, and have opportunity in front of you, you’ve won. If you have stories to tell, and the ability to learn the skills you want to master, and the fire and the drive to do it, you’ve already won. I used to be obsessed with the outcome, the finish line, the achievement. I wanted the stage, the trophy, the recognition, more than I wanted the actual prize. The actual prize being something I was proud of that could take me those places. The actual prize being something I already have. My partner and I’s saying is “we already won”, Because even if we aren’t where we want to be yet, we can get there. And just the word can is a win. We believe we can. We know we can. We will. And just in that, we already won.

Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why? He or she might just see this, especially if we tag them. :-)

Taylor Swift. Her prolific writing, brilliant mind, and the way she expresses herself and uses her platform… I’m such a huge fan, of her music and just of how she handles herself. She’s an icon and I respect and admire her so much. To get to talk to her, pick her brain, and engage with someone with such a masterfully built and inspirational career would be life-changing. (I actually have a recurring dream that we are friends and hang out. As someone who hopes to have super fans one day, I have no shame in being a super fan.)

How can our readers follow you online?

Instagram: @taylorwatson

TikTok: @taylorwatsonoffical

Twitter: @iamtaylorwatson

This was very meaningful, thank you so much! We wish you continued success!