The Deal Is Not the Dream

The Artist, the Manager, and the Little Business Nobody Asked For

Photo by Miguel Alcântara on Unsplash

When I started this band, my instinct was to pitch labels.

Every time we broke a little piece of wood off some door, I turned it into a label email.

We got a radio spin. Pitch the label. We got press. Pitch the label. We booked a decent show. Pitch the label. Every small piece of momentum became another little flare shot toward the castle.

Looking back, who knows if anyone even opened those emails. Maybe they did. Maybe some assistant saw the subject line, sighed softly, and sent us to whatever digital pasture they keep hopeful bands in. A lovely place, probably. Lots of unread EPKs and one sad picnic table.

But I thought that was the path.

Because that is what a lot of musicians believe. You make the music. You get noticed. A label finds you. The machine starts moving. Somebody with a job title and nicer shoes than yours turns your little band into something bigger.

That was the dream.

Or at least it used to be.

Over time, I started pitching labels less and less. Not because the band was doing less. The opposite. We were getting better opportunities. Better radio. Better press. Better shows. Better rooms.

But I was also learning more about how the business actually works now.

And the more I learned, the less magical the label looked.

Labels Are Like Banks

Bob Hope famously said, “A bank is a place that will lend you money if you can prove that you don’t need it.”

Lately, I have started to think about labels the same way.

They are not looking for a reason to believe.

They are looking for evidence that belief has already happened somewhere else.

There is too much music in the system now for anyone to sort through it cleanly. The denominator has gone insane. Human bands. Bedroom artists. Fake bands. AI sludge. Royalty farms. Algorithmic wallpaper. Everybody shouting into the same burning room.

So labels watch socials and Spotify the way traders watch the NYSE ticker.

Monthly listeners. Saves. Skips. Tour history. Engagement. Market reaction.

The artist becomes a stock chart with a guitar.

Romantic stuff.

The artist’s job then, if you want label attention, is to make people care.

But here is the rub: if an artist has to build the audience, create the proof, find the curators, book the rooms, shape the story, and generate the heat before the label gets interested, then the label has accidentally trained that artist to operate without one.

That is the strange little contradiction in the modern music business.

The way labels reduce their risk is also the way they teach artists to need them less.

Being Signed Is Not the Same as Being Helped

There are labels that still add real value. Of course there are.

Money matters. Staff matters. Distribution matters. Radio promotion matters. Press, sync, tour support, manufacturing, playlist relationships, legal help, strategy, access, and scale all matter.

A good label can still be a cannon.

But a small label that fronts some recording costs, tells the artist to tour constantly, provides no meaningful booking help, no real press machine, no radio strategy, no audience development, no clear market plan, and no visible lift?

That is not a cannon.

That is a hat.

Maybe a nice hat. Maybe a hat with a logo on it. But still a hat.

We have had a few of these offers.

And at first, I was tempted. We would be “signed.” Isn’t that the first big goal?

But then I looked around at friends who were already “on a label,” and I could see what that meant in practical terms. They still book themselves. They still pitch themselves. They still carry their own draw. They still handle their own relationships.

In some cases, the label fronted some money. Not all, but a little. But then it also gives orders.

Tour more. Play here. Play there. Put this other artist on the bill. Regardless of whether the other artist makes any sense.

And that is the difference artists need to understand.

Being on a label is not the same thing as being helped by a label.

A label should increase something: money, reach, access, credibility, infrastructure, leverage, opportunity, speed, or protection.

If it does none of those things, then what is it?

How I Accidentally Became the Label

Somewhere along the way, I split myself in two.

On stage, I had the band name.

Off stage, I eventually had RKM.

Rich Kolo Management.

Which sounds more official than it is. It is still just me, a laptop, a Gmail account, a little website, and the growing realization that I did not want to keep having the same conversation as the artist.

Because the artist is supposed to be grateful.

The artist is supposed to smile when the offer comes in. Shake hands. Mean it. Act like being wanted is the same thing as being treated fairly.

And for a while, I was grateful.

I still am grateful.

An offer came in and the artist side of me felt relief.

They picked us!

But another part of me started asking a less romantic question: What are the terms?

We were growing. More streams. More follows. People wearing our shirts.

And I started thinking about what I wanted to spend our fan equity on.

Because once people start following along, you owe them more than motion. You owe them judgment.

I looked around for management at first. I wanted someone else to be the uncomfortable person. Someone else to ask about the money, the billing, the set time, the guarantee, the backline, and the weird little surprise that always appears on a show like a raccoon in the walls.

Then the annoying truth showed up wearing my shoes.

I am an attorney. I know how deals work. I know the words to use. I have negotiated all kinds of things with people who did not particularly want to be negotiated with.

And I knew something artists sometimes forget:

Just because you say no to an offer does not mean the offer disappears.

Sometimes no is the first honest sentence in the conversation.

So I became… I mean, I founded RKM.

No ribbon cutting. No glass office. No sync department. Nobody saying “brand ecosystem” into a headset.

I just started doing the job under a different name.

I was management representing an artist.

They made an offer. I made a counter. Not because I was trying to be difficult, and not because I thought we were owed a parade with tiny horses.

Because this was a business conversation.

Management became the firewall between the art and the little grease fire of the business.

And then I realized what had actually happened.

I had not become a label exactly.

But I had trained myself to do label work.

RKM was pitching the band. Booking the rooms. Watching the numbers. Building the story. Finding the curators. Negotiating the offers. Protecting the artist. Turning small pieces of attention into the next slightly larger piece of attention.

I was doing the development work.

Creating proof.

And somewhere in there, I stopped worrying so much about whether some label was ever going to pick us.

I Wanted to Play Guitar. I Got a Spreadsheet.

This is the part nobody really tells artists.

A lot of us are already doing label work.

We just do not always recognize it as label work.

We book the shows. We build the bills. We make the posters. We pitch the writers. We send the songs to radio. We watch the numbers. We chase the playlist adds. We answer the emails. We figure out which rooms matter and which ones only look good in a calendar app.

Maybe we do not have the staff, the budget, or the experience.

But the work is the work.

And if you keep doing it long enough, you either get better at it or you keep paying tuition in bad decisions.

No one starts writing songs because they want to spend their nights tracking every program director change at every alternative station in the country.

But that is the cruel little joke.

If you want to do the art for a living, you eventually have to understand the business around the art.

And once you start paying attention, the business stops looking like magic.

It starts looking like work.

Patterns. Signals. Relationships. Follow-ups. Small pieces of proof that can be carried to the next person.

It also teaches you something artists hate learning.

More is not always more.

Most of the mistakes I see come down to the same thing: artists spend their fan equity too cheaply.

Too many shows. Too many asks. Too many “big announcements” that are really just another Tuesday. Too many nights where the same friends are being asked to prove they still love you by standing in the same room again.

You played a show on Saturday night. Maybe you do not need the show on Sunday.

Because sometimes all you are doing is making each subsequent show less special.

You can teach people that missing you is fine because you will be back next Thursday, and probably the Thursday after that, and possibly at a brewery with a dog costume contest.

Being active is not a strategy.

The goal is not to become a little record executive in leather boots.

The goal is to understand the trade.

Because the artist who understands nothing about the business is not purer.

They are just easier to confuse. Easier to flatter. Easier to underpay.

And easier to put on the wrong bill, in the wrong room, for the wrong money, while someone calls it an opportunity.

Curators Create the Proof Labels Wait For

So what did I focus on when I stopped pitching labels?

Curators.

People with a voice. People with a following. People whose taste had already earned trust somewhere.

Radio programmers. Writers. DJs. Bookers. Promoters. Festival buyers. Rooms with a real identity and an audience that shows up because the room told them something good might happen.

That mattered more to me than chasing another vague “keep us posted” from a label.

Because the right curator does not just notice momentum.

The right curator can create it.

A label may look at your numbers and ask, “Is there proof?”

A curator can help make the proof.

That is the difference.

Some festivals work that way. Their whole purpose is curation. Mile of Music in Appleton, Wisconsin, is the perfect example. They are not asking whether your audience is big enough to make their event matter. Their event already matters. Their audience already trusts them.

They are not trying to borrow your crowd.

They are introducing you to theirs.

That is a completely different kind of opportunity.

And if you do the job right, you pay that trust back. You show up. You play well. You follow through. You make the curator look smart for opening the door.

Then the next door gets easier.

A few listeners. A quote. A contact. A better bill. A better time slot. A little proof.

Not an explosion.

A chain of small permissions.

The Goal Is Choice

If you keep doing that, slowly, carefully, stubbornly, the strangest thing happens.

The audience is not theoretical anymore.

It has faces.

The rooms get better. The press gets easier. The radio people remember your name. The festival booker wants to hear the next record.

And when the label finally turns around and says, “Now we’re interested,” you are no longer standing there empty-handed.

You built the songs. You found the listeners. You earned the curators. You booked the rooms. You created the proof.

You are bringing value into the room.

So, what are they adding?

And whatever they can do, is it worth the money, the rights, the control, and the piece of the thing we already built?

That is not bitterness.

That is leverage.

Because if you had to become a business to get the industry’s attention, you should not stop thinking like one the moment somebody walks into the room with a contract.

And if the day comes when the label finally says, “We want you,” the artist gets to do something the younger version of himself never imagined.

He gets to tilt his head, look back at the thing he built, and ask:

Yeah. But do I want you?

Rich Kolodziej is a writer, lawyer, musician, and former trial attorney from Chicago, IL. He received his JD from DePaul University College of Law and spent over two decades in the courtroom, earning more than 75 jury verdicts. In 2019, seeking a better work-life balance, he shifted away from daily litigation — freeing up space for a secret musical project with his wife of seven years. Their band has since played Main Stages at Summerfest in Milwaukee, did a set at SXSW in Austin and rocked the Richmond International Film Festival in Virginia, with many stops in between.

If you enjoy my writing and my perspective and you’d like to support the work, you can “buy me a coffee.”