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Music Star Judah Holiday: “If you don’t believe in yourself, no one will; It sounds fluffy but it’s actually a real strategy”

If you don’t believe in yourself, no one will. It sounds fluffy but it’s actually a real strategy. It affects everything we do and at times I still struggle with it. When you believe and are in that mindset, opportunities tend to show up. That’s what I’ve found at least. I had the pleasure to interview […]


If you don’t believe in yourself, no one will. It sounds fluffy but it’s actually a real strategy. It affects everything we do and at times I still struggle with it. When you believe and are in that mindset, opportunities tend to show up. That’s what I’ve found at least.


I had the pleasure to interview music star Judah Holiday. Born and raised in New York City, Judah discovered his musical talents early. He began playing drums at age seven, then moved on to guitar in order to explore his natural affinity for melody. After writing his first song at age 14, he steadily built up a body of work showing the strength of his melodic talents. Throughout his early 20’s he became a regular in the Lower East Side music scene, playing regularly at the legendary CBGB Gallery, Crash Mansion, 169 Bar and Recoup Lounge. Now, based in Miami, Holiday taught himself how to record and produce his own music, working daily to perfect his craft. He is inspired by music icons like James Taylor and Neil Young, as well as by more contemporary artists such as Gavin DeGraw, Coldplay, and Matt Kearney. The official video for his new song “All That I Got Tonight” is out now, along with his new song “Shout Out Loud”.


Thank you so much for joining us! Can you tell us a story about what brought you to this specific career path?

I was a very bad student but a very big dreamer. I used to fail school but write great songs. I think from a young age I knew that I needed to continue being bad at school so that I could eventually be a struggling artist. If I got to that stage where I would be accepted as an artist, I’d take it from there. I guess I realized for a very long time without admitting how much I loved music and saw that life for myself.

Can you share the most interesting story that occurred to you in the course of your music career?

I met Kevin Rudolf in a really interesting way! He was selling some guitars and a friend of mine knew him so he asked me if I was interested in buying one. I got the gear list and said that I was interested in the cheapest one which was I think a Martin DX1. I only said this to actually meet him and hopefully see if I can play a few songs for him. The following day I came back ready to buy that guitar and I totally transformed that situation into putting me in the limelight. I was ranting about my songs, etc. After making that initial connection with some persistence and borderline harassment, he finally said, “Okay, let’s work together!” Woohoo! The coolest part, which I now sometimes take for granted, is he has become a dear friend and is executive producing my album and me as an artist.

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

I just finished recording my debut album which doesn’t have a title yet. I am really pumped to share my music with the world. I just released my third single “Shout Out Loud” and it is doing really well! People are responding really nicely to it!

Who are some of the most interesting people you have interacted with? What was that like? Do you have any stories?

I would say that my producer Alex Bilo is a very interesting and hysterical character. Working with him is like autocorrect on an iPhone. Before you have a chance to mess up he already has me back on track. It was a real treat working with him on this album!

Which people in history inspire you the most? Why?

Neil Armstrong. He was the first man to walk on the moon ever, meaning there was no previous information on what that experience was like. He literally was the first to do something out of this world and not knowing what something is going to be like, especially walking on the damn moon, is a pretty fearless and noble thing to take on.

How have you used your success to bring goodness to the world?

I donate monthly to the Humane Society of the United States to help animals in need. We have two rescues and they are so amazing. Nava and Frankie. I love them.

You are a person of great influence! If you could start 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 would probably create the first online Woodstock so people disabled or unwell could watch their favorite bands perform from the comfort of their own home. It could all be streamed from their individual location. (I want 10% for that Idea!)

Which tips would you recommend to other artists to help them to thrive and not “burn out”?

Just like an addict does, take it one day at a time or if you’re hungry, eat an elephant one bite at a time. Things will turn up with persistence.

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

  • This won’t happen quickly. Anything good/great takes time. In hindsight, it’s obvious.
  • This process won’t always be fun. Sometimes it feels like work or will burn you out.
  • You will doubt yourself. The struggle is real in this business and there’s a lot of talented people and good music out there. There’s always going to be people in your ear. Trust your gut.
  • If you don’t believe in yourself, no one will. It sounds fluffy but it’s actually a real strategy. It affects everything we do and at times I still struggle with it. When you believe and are in that mindset, opportunities tend to show up. That’s what I’ve found at least.
  • Winning feels better than you think. Because of the contrast of losing all the time, which is a natural part of winning. But when a “W” shows up, it means a lot.

We are blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. 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 just might see this, especially if we tag them 🙂

Gary Vaynerchuk. He came from nothing and made something. He was an underdog but won. I call him a won-derdog.

How can our readers follow you on social media?

Follow me everywhere @judahholiday

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