Valuable Mistakes: How I Turned Freestyling Outside the GRAMMYs into a $50,000 Check

Always listen to your gut.

This is the second entry in our new series Valuable Mistakes, in which artists share, in hindsight, a killer mistake that proved to be valuable. Our latest feature is written by Jersey-born Jewish rapper Kosha Dillz, who has released four albums over the past 12 years, including 2016 LP, What I Do All Day And Pickle.

My name is Kosha Dillz and it turns out that the most valuable mistake of my career was actually never a mistake—I just thought it was.

2015 was a stellar year for my career. I got booked on the Vans Warped Tour, I went viral for getting hacked by ISIS, and I was coming off a strong release for my latest full-length album, Awkward in a Good Way, on Murs’ Label 316. At the same time, the album's producer, Jesse Shatkin (aka Belief), was also working with Sia.

While creating what might be his last hip-hop album with me, their song "Chandelier" reached the entire planet.

Unfortunately, as Jessie started producing records for massive bands, I found myself rapping outside the Roosevelt Hotel on Hollywood Blvd. to make some extra cash. I made some tips here and there, randomly connecting with Jared Leto, A$AP Yams and a writer from LA Weekly, but, by and large, I was mocked by all the “cool LA people.”

Knowing that things would take off that summer, I did what I had to do and made ends meet.

The same week I was selling physical copies of my album hand-to-hand while freestyling about people's weird outfits, "Chandelier" earned three GRAMMY nominations. I thought, "Here's my big chance to be in the company of all the GRAMMY schmoozing types."

Much to my dismay, when I contacted Jesse about a ticket, he informed me he only had one extra and he was taking his mom. All good. Later that week, I contacted a fellow rapper friend by the name of Mega Ran, who I knew consistently attended GRAMMY functions. If anyone could score me a ticket, it was Mega Ran. 

I decided to PayPal Mega $300, begging him to snag me a ticket. Unfortunately, I was too late. Even though he was a GRAMMY member, he couldn’t get me a ticket.

"Sorry man," he replied.


I just wanted to rub shoulders in a nice suit with the other “suits.” 

My roommate at the time, Lonnie, a former cab driver turned rehab mogul, told me, “Don’t be a bitch, Rami, you should go and rap outside the GRAMMYs!”

Given that Lonnie was the same guy who told me to get Pro Tools in 2012, which directly led to me landing a placement for my "Celluar Phone" record in a Bud Light Super Bowl commercial—a move that financially changed my life—my gut said he was right.

Everyone I knew told me it was a terrible idea and that I was making a huge mistake. But I did it anyway. 

And as insane as that all sounds, indirectly, it paid off.

I was kicked off the lot four or five times by security after freestyling about Paris Hilton, but in addition to meeting "Weird Al" Yankovic and making $40 in tips, I was able to shake hands with an agent from William Morris. Jesse didn’t win any GRAMMYs that evening, but, I thought, "At least I landed a meeting at William Morris." 

Sadly, that meeting didn't amount to much, but roughly one month later, I got an email from Chevrolet, which stated I needed a SAG card because "My face would be used in a 'We use real people, not actors' national commercial."

I literally said three words on camera ("Pretty bomb dude!") and they only caught the back of my head, but that commercial made me $50k. Right place, right time.

Thanks to some humility, I went from trying to attend the GRAMMYs to earning more than an independent, entry-level record deal.

For me, street performing wasn’t about street performing; it was about doing the opposite of what everyone but Lonnie (and my gut) thought was a good idea. If you don’t listen to your gut, you'll never win.