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GRAMMYs, MSG, YouTube. What pays the bills? None of the above.

Which One Pays the Bills? What a GRAMMY Performer Knows About Private Events

October 10, 2026

Brian has played Madison Square Garden. He performed with the Foo Fighters at the GRAMMYs. And his calendar is packed with private events for the rest of the year.

So Matt asked him the question every performer should ask: MSG, the GRAMMYs, or private events. Which one pays your mortgage?

On this week’s Coaches Corner, Matt sat down with Brian, a multi-instrumentalist he has shared stages with for years at private events and original shows. They talked about which stage actually pays the bills, what that work buys him besides money, and the one call he wishes he had taken.

The answer took two words

“Private events. Yeah.”

Brian didn’t have to think about it. He compares his original shows to Spotify royalties.

“I would say, like, original shows is, like, your royalties from Spotify. I think they’re pretty analogous.”

Private events are what scale. Brian has a five-year-old, a mortgage, and the same bills as everyone else. He has no W-2 and no day job. So Matt asked what performing at private events gives him. He answered in one word, then added a second.

“Freedom.”

“Autonomy.”

Booked as yourself

When Brian started working with event agencies, the message was always some version of the same thing.

“We love what you do, but can you do this instead?”

That changed. For the past decade, it has sounded like this:

“We want you because you’re you.”

He says that freedom is worth more than people think.

“The freedom that comes with not having to be also an actor all the time… the freedom from that is irreplaceable.”

Brian doesn’t change who he is to fit the room. He brings the same show whether the crowd is huge or small.

“I’m gonna be the same guy, given the same energy that I would playing for 35,000 people as I will for 300 guests at a really elegant black tie affair.”

And clients notice. At almost every event, someone walks up to tell him the same thing.

“We loved what you did, but more than anything, we just felt like you really look like you love what you’re doing.”

His marketing works the same way. Brian spent years trying to capture himself in polished videos. What finally worked was posting real clips of himself doing the thing at events. Traditionally, most of his work came from people who saw him at someone else’s event and hired him directly.

“I became the product and the product became me. That was the turning point.”

You don’t have to cosplay a luxury identity to get booked at the high end. You have to be so clearly yourself that nobody else can fill the slot.

Money buys back time

Matt asked Brian what his work affords him, and said up front he wasn’t talking about money.

“Honestly, when I think of the word afford now, I don’t think about it largely in terms of money. All money is enabling me to do is buy back my time to spend it with my family.”

That’s the real goal of a private event business. Not more gigs. More choice. Brian put it this way:

“The goal is to get to a point where you’re saying no to just about everything, because the yeses that you will say will fill your calendar.”

Matt pushed it one step further.

“Not even the calendar, the bank account. You have enough, right? So you can decide how much you wanna play.”

Sharpening the same sword

Brian takes the prep for his events further than almost anyone. For wedding ceremonies, he builds full arrangements ahead of time, so the videographer gets a finished soundtrack on the day.

“It’s like having a sound stage with a director, and they’re watching a live feed of the wedding, and they’re scoring them. That’s what I’m going for, that level of production.”

That extra work does three things for him at once.

“It’s made me better in every possible way. And it is also justified by price, and what makes me different. It all rolls in.”

And it feeds his own music too. The skills he uses for clients are the same ones he uses as an artist.

“I’m sharpening the same sword that I’m gonna use for my own music, all the time. It never gets rusty.”

Compare that to the musician who funds their art with a cubicle job. As Matt said on the call, that work pays the bills, but it isn’t sharpening your music muscle.

The one call he’d take back

Near the end, Matt asked what Brian would tell his younger self. Brian answered with a story.

Two days after the GRAMMYs, he got a call to be a supporting player for an artist on The Tonight Show. He had just flown home. The pay didn’t cover the flight, so he did the math and stayed home to play three bar gigs instead.

“Dumb.”

Nobody warned him. Even musicians a decade older told him it was a good idea, and that he’d get another call.

“You don’t get another call.”

“If you get behind the curtain, that’s your one chance to be in that club and be thought of by people that pull the levers.”

He also says he played it too cool around his heroes when he should have been himself.

“I should’ve been the enthusiastic person that I just am. I shouldn’t have been trying to put a mask on.”

The lesson isn’t about one gig. It’s about knowing when the short-term math is the wrong math, and having people around you who will tell you so. Brian puts it plainly:

“If you have the desire to do something, you should be trying to find other people that are already doing it and learn what they’re doing that you’re not doing.”

Today, the private event work is what lets him take those swings.

“Doing what I’m doing now with my life and my career gives me the chance to be like, ‘I could jump in the deep end and we’ll just see what happens with this one.’”

Which one pays the bills?

The big stages build the name. The private events pay the bills, buy back the time, and keep the sword sharp for the music you actually want to make.

Brian closed the interview with this:

“If it helps anybody at all, if it buys you two months of less wasted time, then job done.”


Want to build a private event business that pays the bills and gives you your time back? That’s exactly what we do inside Well Paid Musician.

Watch the full episode with Brian on YouTube.

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Matt Santry

Matt Santry is a performer and educator who's voice has been featured in commercials with top brands like NBC's The Voice, Dollar Shave Club, Febreze, and many more As a performer, Matt stays busy with private events and travels the US to work with high end clients. Founded in 2019, Well Paid Musician is a training program born from the 20+ years of Matt's experience. This program has helped hundreds of musicians from all over the US earn more from performing and break the $100K+ barrier.

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