The Black Crowes Catastrophe

We all make mistakes. As a society, it feels like you can’t talk about your mistakes and that you should be embarrassed by them. You have meeting after meeting where you talk about all your wins, how it’s your best quarter, how you brought in that new client, whatever it may be… But it’s all a lie. No one is perfect, and no one is working at 100% all the time. 

If you don’t receive our newsletters, you can subscribe here. For those of you who do- you know that I like to include a week of failures, where I list out all of my shareable mistakes. I’m happy to admit that those are typically my most well-received emails, and I think that’s because it resonates with people. We’re told that failure is not an option, but when someone is vulnerable about their imperfections, we’re reminded that we’re all human and making mistakes or failing is OK. 

Recently on the “Why Are We Shouting?” podcast I discussed my biggest business blunder. It was during the beginning of my career in entrepreneurship, it involved a very famous band, and I lost the most amount of money ever. If you want to hear the whole story you can listen online, but here’s the good, the bad, and the lesson. 

The Good 

It was 2005, I had just graduated from law school in Los Angeles and launched my first business where I managed bands. I did everything from publicity to booking to sending them out on tour. I wanted to focus on the paperwork side of the business to allow the artists to do what they do best – create music. I had a relatively well-known client, who I had no business managing. I was brand new to the world of entrepreneurship, and I didn’t know what I was doing. One of my clients, Tim, was a singer-songwriter who had a pop-rock band of four people. They had a ton of fans and a lot of hopes and dreams. One night, Time and I were chatting, and he said: 

“You know, Jill, I’d really love to do a show in Chicago with The Black Crowes.” 

He wanted to play with The Black Crowes, and I truly wanted to impress my brand new client. I wanted to prove to them that I knew what I was doing. So, I went online, looked up The Black Crowes booking agent, and found them! It was surprisingly easy to do. I reached out and said I loved the band and I wanted to book them for a show in Chicago. Almost immediately, an agent, Ryan, responds. We set up a call, and I booked the band! My band was going to open up for The Black Crowes in a month outside of Chicago. Ryan emailed me a contract, and it was done. 

The Bad 

I was so excited to tell my client. I called him, we met at a bar, and I told the band all about it. We were all so pumped! We celebrated the night away. Until the next day, Tim called me and said:

“I don’t want to play a show with The Black Crowes” 

What was I going to say? I was a brand new manager of an up-and-coming band with a brand new company. So I say “No sweat.” 

I called Ryan, the agent, and told him that we are no longer interested in doing the show, and he said “that’s ok… We accept money by check or credit card,” and then he hung up. I had no idea what he was talking about. Several days later, he emailed me saying that there was a cancellation clause in the signed contract. The cancellation clause included a cancellation fee of $5,000. I felt terrible, I had just started this company, and I had no income. How was I supposed to pay for this? So I asked him- I do not recommend doing this.

“He (Ryan) suddenly became that Hollywood music agent that, you know, you hear about or see in the movies. He just said to me, figure it out. And he hung up on me. So I did. I figured it out.” 

I had to dip into my life savings. I collected the $5,000 and mailed the checkoff to Ryan. 

The Lesson 

That check was tough to write, and this memory hurts to talk about. You might be wondering why I didn’t have the artist pay since Tim was the one who canceled, or why I did go to court and dispute the contract. Those are valid questions, but at the end of the day, I was young, naive, I didn’t read the contract, and it was my responsibility to fix it. In my excitement as a new entrepreneur, I looked at everything with rose-colored glasses. I skipped the bad stuff and only focused on the good. 

“I’m such an optimistic entrepreneur anyway, that I usually still to this day, love to skip the bad stuff and get to the good stuff, because that’s where the good stuff lives, right?” 

Of course, anyone could listen to this story, and say “you should’ve read the contract,” “you shouldn’t have entered into this anyways,” but to paint the scene, I was in my twenties and starting a brand new company. I was so excited to be on the phone and build a connection with someone who managed such a famous band – it felt good. Because it felt good, I overlooked all the red flags. 

The lesson I learned was to follow my gut. Life is filled with failures, but with time, patience, and a finely tuned gut – we can avoid some of those big mistakes. Failure is inevitable, but as long as you’re able to own up to your mistakes and learn from them, I consider that a success.