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Podcast Episode

My Most Expensive Mistakes in the Music Business [EP.9]

A solo episode on the Rhythm Changes Podcast

On the Rhythm Changes Podcast, I present 6 of my most expensive mistakes in a long-form version of an upcoming PechaKucha presentation.

My PechaKucha script: my most expensive mistakes

1/20 My name’s Will. If I had to tell you what I do in four words, I’d say: I make profitable music. But I’ve made some expensive mistakes so far in the music business.

Tonight, I’ll tell you about three kinds in particular:

  1. Opportunity cost – the cost of not doing something
  2. Dollar costs – cash coming out of the bank account
  3. Unrealized income – money that I didn’t make

2/20 The first mistake I’m sharing with you tonight comes from when I was part of the Gabriel Dubreuil Trio, pictured here. This is from the Duncan Showroom, the first time we ever played on Vancouver Island.

But here’s the thing: we did not sell enough tickets for this 3-day weekend trip, to be worth the opportunity cost of us taking that time, the total cost of which was:

3/20 $1,000. That’s probably the opportunity cost of the working day that us three guys missed.

Back then, we hadn’t made any systems to reliably turn people out for shows when we traveled. We sold less than 50 tickets across that whole 3-day weekend!

4/20 The takeaway from this is: audience comes first.

When you’re planning where to play, you can’t just show up and expect people to be there. You need to work hard in advance to connect with people.

Fortunately, we got better at that over the years, but this was the first time we messed it up.

The second mistake is to do with my band Early Spirit.

5/20 It’s a flight. Our band flew to Moncton to play a Francophone music showcase.

We had to shoulder all the costs. We had to pay for our own flights, our own accommodations and food, and a registration fee.

How much did that all add up to in costs to play there?

6/20 $4,000. The real part of the mistake, though, was that we got zero dollars of business out of this showcase!

It was a shock because we got several gigs from a similar Francophone showcase in Vancouver.

We thought we could just do it again, but it didn’t happen for whatever reason, and we were out four grand.

7/20 We reached too far. We thought we could extend something that already worked, but we skipped two things:

  1. We didn’t consider how different it was to meet all-new people in a city on the other side of Canada
  2. We thought we had it made; we didn’t expect to lose money

It’s tough to blow a couple grand when you’re starting a band.

Now, all 6 of my mistakes to share tonight are in ascending order of dollars.

8/20 The third one here, there’s just no excuse for. This is the web domain earlyspirit dot-com, which the band let expire on my advice.

I thought, “Well, we don’t need that anymore. We just use earlyspirit dot-CA, so let’s let earlyspirit dot-com go.”

Now, Huge Domains here are re-selling it. Guess how much they are re-selling it for?

9/20 $3,595 USD. That’s over $4,300 CAD. I’m sure we could have captured most of that if we just held onto this domain.

It would have been a tiny cost, less than twenty bucks per year, to just keep renewing it, but I chose not to.

10/20 Domains are like plots of land. You can’t just be giving away plots of land when you’re trying to build some wealth with your project.

I’m passionate about local economies, city ecosystems, and how communities build wealth – especially music scenes.

You can really take every little opportunity to prosper, but I did the exact opposite of that with this one.

11/20 So that’s some mistakes I’ve made with other bands, now here’s one from my solo artist career.

I make music under my own name William Chernoff, and when I put out my first album called Aim to Stay – that’s the artwork.

I paid for a publicity campaign to get press reviews and radio airplay.

What was the cost of doing this all-in?

12/20 $5,000. Why so high? I had to make CDs so that the publicist whom I hired could send out CDs to people in the media.

This upped my budget a lot, and together with the publicist fees, it was a lot more than I could justify in sales – let alone considering the pandemic’s effect on my income at the time.

13/20 I’ve built my whole career so far on doing things a different way, but here I just did it the regular way, even though it didn’t make sense for me.

And I could’ve known that this wasn’t the right fit personally. This expense was too much for an early-career jazz artist. But I don’t regret it because now I understand how publicists work.

14/20 This 5th mistake comes from when I worked at North Shore Celtic Ensemble, NSCE the group you see here.

I worked for them part-time starting at age 18. And they paid me a very part-time $200 per month. Per month!

I turned that into a mistake – an unrealized income – over a period three years, of:

15/20 $14,400. Now how did I do that? Well, somebody else was working there when I started and NSCE paid them $600 per month.

So of course I didn’t know that at the time, but that’s a $400 per month gap for three years – 36 months – and that multiplies out to $14,400, my biggest ever mistake.

16/20 Communicate needs in a negotiation! That’s what I could’ve done. I didn’t know the lay of the land at all back then.

I could have found out what other part-time employees in my field got paid and had the opportunity to add some income here.

But I was totally unaware at 18 that I had to do this. Or that I could do this.

17/20 That’s my biggest mistake in dollars. But it’s not my biggest one overall: that’s this sixth and final one.

It’s something I’m still working through, and starting to get over, thanks to some fun studio sessions that I’m doing right here in 12TH ST Sound in New West.

I need to learn to be kind to myself.

The biggest mistake I’ve made is not being kind to myself.

The cost?

18/20 This one can’t be measured. The extent to which I’ve made life more difficult by being mean to myself, beating myself up, and not getting help through feelings of depression.

I can’t account for all of that.

I was so focused on developing my work that I ignored the personal issue right in front of me.

19/20 But don’t worry, this isn’t a cause for pessimism. I’m excited!

I’ve identified this problem now. I have more help than ever: friends, family, a marriage, and professional help available.

And I can’t wait to see what I’m capable of as I gain confidence and be kind to myself.

I can’t wait to see what that brings.

20/20 Sure I might have had

  • Some empty tour dates
  • A showcase that didn’t turn out
  • An expired domain
  • An expensive album
  • A part-time job that didn’t pay much

But none of that matters if we’re not kind to ourselves and each other.

That’s ultimately the most important lesson I’ve learned from any of my most expensive mistakes in the music business.


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By Will Chernoff

William Ross Chernoff—known as Will to friends and colleagues—is a jazz musician, podcaster, YouTuber, and writer. He records and performs under his own name, William Chernoff.