We caught up with the brilliant and insightful Jake Wildhorn a few weeks ago and have shared our conversation below.

Jake, thanks for taking the time to share your stories with us today It’s always helpful to hear about times when someone’s had to take a risk – how did they think through the decision, why did they take the risk, and what ended up happening. We’d love to hear about a risk you’ve taken.

I think going into the music industry itself is a risk. I dropped out of college when I started getting more opportunities to write songs and play live but it doesn’t just happen. There’s no real blueprint for this, and if there is, it’s ever-changing.

I went to LA to write for other people and came back to New York certain I’d rather write for myself. I paid my dues playing open mics around Manhattan until I could book my own gigs at real venues and even then, you’ve got to figure out how to make any money from it. There are expenses to manage, tickets to sell, and on top of all that, you’ve got to learn how to market and sell yourself as an entertainer. Then you’ve got to actually learn how to be an entertainer, which only comes with time and doing it for real.

The real product though is and always will be the songs. And you really have to sell those too. Writing creativity itself is a risk. Just being an artist and a writer means you’re creating art that’ll be judged for the good or bad by everyone. And unless you’re playing a character you can hide behind, those judgments will never not be personal in some way. Beyond writing, the record business doesn’t really exist anymore, so you need to navigate the swamp that is streaming and figure out how to get people to hear you so you can build an audience that’ll come to your shows. It’s an investment in every way possible.

If you can get past the embarrassment of failure, you’ll start to grow as an artist quickly. And believe me the foundation of every artist is built through failure and the mistakes you learn from.

I played my way through the rock clubs of NYC, starting with Wednesdays, then Thursdays, then Fridays until I became a weekend headliner. I got to tour the U.S. with the legend Gordon Lightfoot as his opener until he passed. My music’s been streamed hundreds of thousands of times, and my song Heaven Can Wait even played on radio stations across the country for a while, which was a dream come true.

Twenty-plus years ago, any one of those things might’ve made your career. But today, it’s all just stepping stones. With social media and the entire catalog of music history at everyone’s fingertips, you’re competing against the world.

Jake, 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’m Jake Wildhorn. I’m a singer-songwriter from New York. I kinda like the simplicity of saying that sometimes, because for me, I think it’s all anyone really needs to know. I’m a private person working in the entertainment industry, which is funny, considering I’m the front man. Don’t get me wrong, I love goin’ up there and playing for people, but it’s about the music for me. I guess I’ll talk about myself for this though, haha.

I grew up born and raised here in New York, split between Westchester and Manhattan. My dad’s a songwriter and my mom’s a singer, so the trajectory of my life isn’t a surprise. I grew up on early 2000s rock and all my dad’s old records from the 60s and up, so to narrow down my influences might be tough, but I was always a big fan of Rob Thomas and Matchbox Twenty, Gavin DeGraw, Linkin Park, The Eagles, The Beatles, etc.

That’s not to say I always wanted to do this music thing though. In my more angsty teenage years, I definitely thought maybe music was too obvious or I was fighting against destiny, but who am I kidding, I love making music. I found a purpose young, which is a gift. Having a dream is one thing, but just being able to do it is another. I’m fortunate. The older I get, the more I try not to take it for granted.

I guess the only other real passion I had goin’ for me was boxing, which I’ve done since I was 13. I’m 25 now and probably have a little more mileage than I should, so I’m slowing down now, haha. But with music, I’ve gotten to see the world and play my songs for thousands of people. Yeah, it’s not always easy, but man is it worth it. We’re growing every year and making more stories.

I got my second album coming around the corner and a lot more exciting stuff to follow, so it’s a good busy time right now. I just hope the songs I write feel real to people. They can take whatever they want from them, but as long as people feel something the way our favorite music did as a kid then mission accomplished.

For you, what’s the most rewarding aspect of being a creative?

There’s a connection that happens when you’re on stage between you and the audience. Whether it’s a bar, a theater, or an arena full of people, you’re giving your all to them. And God willing, there’s a moment when you feel the audience meet you in the middle. It’s like a sunrise on a sea of souls. Sounds crazy, but I don’t know how else to explain it. You just can’t get that feeling anywhere else.

In your view, what can society to do to best support artists, creatives and a thriving creative ecosystem?

Go out and see live music. There’s a lot of amazing artists who might never get the recognition they deserve and thats just life. But if you buy a ticket, or a cd, or a vynl, thats real. Artists make a cent of a cent from streaming. If you value what an they make you should support it.

Contact Info:

• Instagram: @JakeWildhorn
• Linkedin: https://linktr.ee/JakeWildhorn
• Youtube: @jakewildhorn
• Other: Jake Wildhorn on all music streaming platforms