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Andy Grammer

Keep Your Head Up

"Pain is something that grounds a lot of the positive stuff.”

Music is something that’s always been in my life. I love it. I used to sing in school, and I’m fascinated with people who pushed through the toughest times of their art to make their dreams become a reality.

I had the pleasure of interviewing Andy Grammer on a past episode and there’s a lot he’s said that has stuck with me.

When the universe seems like it’s telling you to stop and give up, that’s when you have to push even harder and let it know you’re serious. That’s exactly what Andy Grammer did.

His dedication brought him from busking on the streets of Santa Monica to being a multi-platinum artist.

I hope you’re as inspired by his story as I was, on this 5-Minute Friday clip in Episode 573.

"It’s a sweet defiance to follow your purpose.”  

Some Questions I Ask:

In this episode, you will learn:

  • Where Keep Your Head Up comes from (1:05)
  • Andy’s Mystery note (1:26)
  • How Andy got what he wanted from the Universe (2:34)
  • About overcoming insecurities (3:51)
  • Plus much more…


Show Notes:

Connect with
Andy Grammer

Transcript of this Episode

Interview With Andy Grammer

Lewis Howes:                      This is 5-Minute Friday!!

Oh, we’ve got a big one today, guys. I was enamoured with our guest today and the adversity that he overcame to achieve his dream. Now, for those that don’t know who Andy Grammer is, you are in for a beautiful treat.

He is an American singer, songwriter and record producer. His debut album, “Andy Grammer” was released in 2001, and swamped the hit singles, “Keep Your Head Up” and “Fine By Me”. He became the first male pop star in a decade, since John Mayer in 2002, to reach the Top 10 at adult pop radio on his first two singles. And that is just the beginning, my friends.

Andy Grammer:                  “Keep Your Head Up”, even just the title, you’re like, “Mmm… I don’t know…” And what was funny is that it was, I think people could feel, the reason that that one did well, I just lost my mom. She passed away about eight years ago and that song came from being on the street without getting any real acknowledgement, success, no-one seeing you for what you think you are.

That period of my life, I remember I was rehearsing in my Santa Monica apartment and there was a knock on the door, and I went out and there was a little sticky note that said, literally, it said, “Give up the dream, your voice is terrible.”

Lewis Howes:                       No way!

Andy Grammer:                  And I remember… And there was nobody even there! It wasn’t even  someone that I could be like, “Ah, well you’re just… you just suck! Like, you’re just the worst person ever!” It was just, like, the world, being like, “Ugh… Stop!”

Lewis Howes:                       Give up. Wow.

Andy Grammer:                  And, so, I was out on the street, doing my thing, and there was a whole day that went by that I didn’t get any dollars. And I was, like, “Wow. This is really intense.” And I had my little cart, and I…

Lewis Howes:                       Zero dollars? The whole day?

Andy Grammer:                  Zero dollars! The whole day! I don’t know if it was overcast or something, or no-one was coming, but it’s such a funny thing, such a sweet defiance to follow your purpose even when you’re… The only reason you’re allowed to be there is because it’s freedom of speech. Right?

Lewis Howes:                       And you have a permit.

Andy Grammer:                  Yeah, I have a permit. I paid, like, $35 for the year to be able to just have freedom of speech with my guitar, and I’m singing to no-one! And people that are there are just not interested and they’re walking by. I packed all my stuff up, just like, “Man! Amazing! Wow, okay!” and I’m leaving and I looked up at the sky and I was, like, “Your move! Whatever’s up there! I literally will never leave! So, if you want me to be here in fifty years, just, like, singing because this is the only opportunity that I have, and I’m going hard at it, then I’ll be here. It’s your call.”

And I do believe there is something about, like, once you state your intentions, and once you put it out there into the universe, of where you’re going, then some things go, like, the secretary at the desk of the universe is, like, “Ah, no, he’s serious, we can give it to him, yeah.” Like, “He’s not going to leave, we should probably give it to this guy. He’s just going to be annoying. He’s going to be annoying until something…”

And so, after that I went home and I wrote that song. Oh, but I do believe, you know, my Mama passed away, I had zero dollars, I was living in a pretty crappy apartment, and so out of that, if you hear that guy saying, “Keep your head up,” then you’re like, “Oh, I’ll listen to what you have to say. Go ahead. What have you got?”

Lewis Howes:                       It wasn’t like everything in your life was good.

Andy Grammer:                  Yeah, it wasn’t like some sort of trust fund baby that was just like, “Everybody, it’s cool!” Yeah. Pain is something that grounds a lot of the positive stuff. You need them both to make it feel real. Yeah.

I do love to talk about this because, I don’t know if I heard enough of this when I was coming up, so in any business or art form… Oh! One of my favourite quotes is, “The reason we struggle with insecurity, is because we compare our behind-the-scenes with everybody else’s highlight reels.”

So you go through your life and you’re like, “Man, I’m on year three out here and… did Prince do this? You know, like, was Prince on the street? I don’t know. All I’ve seen of Prince is on the cover of Billboard, and I feel like maybe he just was born on Billboard.”

I like to try and be as open as possible, because I think there’s probably a lot of people out there that are really good and have something awesome to share with the world and need to know that I didn’t just go like, “Oh! It’s working!” I went, “My cover of this band that I think I like makes people stop for thirty seconds.”

And then I slowly was like, “I’m going to write ten songs that sound like that one.” And out of those ten, none of them are good, but the tenth one is kind of intriguing, so I’m going to write another ten.

Lewis Howes:                       Like that one.

Andy Grammer:                  Yeah, like this one. So then you write another ten and, guess what, number seven of those ten, you’re getting people to at least take a look, you know?

Lewis Howes:                       Yeah, just clap, stomp their feet.

Andy Grammer:                  And just over and over and over and over again. So, there’s a relentlessness to, whatever, greatness, that I think is really, really important.

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