How I ended up in business

I was a musician.

I didn’t have an aversion to learning the ins and outs to business, but I also didn’t think I would ever need to.

Like many musicians, I figured one day I would be discovered by an A&R rep. It seemed natural. Everyone who saw me play guitar couldn’t help but feel I had a promising future ahead of me.

But I became desperate. My way wasn’t working. I needed to find a new way.

I was struggling immensely. I was behind on my mortgage payments, working five jobs, living with a room mate straight out of hell. I would go to open mic night on Tuesdays just to get away from the gong show at home.

Aside from the open mic, rehearsals, and the occasional gig, there was no time for music. I couldn’t engage fully in my passion.

It was wonderful that everyone thought I was a talented musician. And awful that I couldn’t figure out how to make a living doing what I loved to do. I was fearful of being judged and being told that I should give up and get a job.

Sobbing in My Blue RAV4 with 2 Flats

So, I was struggling and exhausted. I felt like a loser. Working five jobs will do that to you.

And I needed to figure out a way to get out of that mess. The mess I had created.

I was about to give up. I honestly felt like I was at the end of myself. One Sunday, I ended up sobbing, in my blue RAV4 with two flats, after church, in front of an Italian restaurant, after enduring repeated, embarrassing, punishing failures spanning months and even years.

Shortly after, I was introduced to the world of business. And I got something I had never gotten before. I got that I needed to have a long-term mindset. To be consistent. To add value to people. I got that I needed to legitimize my career and get help from people with skills I did not have.

Now I was a man with a plan.

A $100,000, Multi-Year Lesson

As it turns out, you can’t learn how entrepreneurship and business works overnight.

It was great that I was excited about new possibilities. But I couldn’t see the steep learning curve stretching out ahead of me.

I made more than a few expensive business mistakes, costing me over $100,000 cumulatively. I call this my “expensive business education” now, but back then this was devastating.

I mean, can you imagine feeling sure about a music industry tech startup one day, investing whatever money you had, sincerely believing you’d end up a millionaire…

…And losing it all the next?

This really happened, though it didn’t happen overnight. It unfolded over the course of three years.

When that happened, I can’t remember feeling a thing. I was empty.

The Difference I Get to Make

But regardless of the expense or time it took, one way or another, I got my business education!

Then it was a matter of distilling what I had learned into usable strategies, tactics, and principles for musicians — musicians who know what it’s like to put their best foot forward for months and years and end up with nothing to show for it.

The coolest part about all this is not that I can build businesses (even though that is cool).

The coolest part is a) the personal growth I gained from going on that journey, and b) the musicians I get to impact.

When I see that light bulb pop up over a fellow musician’s head, I couldn’t feel more excited. There’s nothing that gives me a greater sense of satisfaction than knowing I’ve made a difference in someone’s life.

Founder of Music Entrepreneur HQ. Download your free guide: