How I Unexpectedly Made Money As A Musician: Or Pasta Thrown At Walls

How I Unexpectedly Made Money As A Musician: Or Pasta Thrown At Walls
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A few months after deciding to become a full-time professional musician, I came to the conclusion that there isn’t a right way to “make it” in the music business. No one has the formula for why certain records stick, and few artists and industry professionals (Amanda Palmer, Gregory Alan Isakov, and Judd Greenstein, for example) truly understand how to explore the emerging intersection of disruptive technology and crowdfunding and streaming platforms and crossover collaboration and call it what you will, it’s a mess.

I have spent the past three years trying everything. Most of it isn’t working: My social media numbers are laughable. I am considered to be twenty pounds “too cute” for mainstream indie rock. And I live on multiple lines of credit.

It’s hard. Most days I think about quitting.

But I don’t. Because for every ten noodles that did not even make it close to the wall, I remind myself that one got closer than the rest.

With that in mind, I wanted to talk about something that appears to be working: a model of touring I probably didn’t invent called Holly’s Pop-Up Model of Touring.

This is where I drive and fly and take trains all over the world to play lo-fi concerts almost anywhere but in a club. In the past twenty-eight months I have booked over 200 shows in caves and chocolate factories, churches and schools, recording studios and tumbleweed-trellised backyards, sensory deprivation flotation tank centers and the headquarters of NASA’s active ISS mission control (different venues, believe it or not!).

The list goes on and on, and it includes stops in Kosovo, Albania, and Montenegro. That’s right. Earlier this year I set up what may have been the Balkan’s debut all-American indie-country-opera pop-up tour.

The first iteration of that tour, The Holly & Ken Road Show, thirty-nine shows in forty days throughout the United States, was 14,000 miles of sheer madness. In five weeks we generated $27,000 in revenue (after expenses). If you’re not inadvertently thinking about how much any producer from Hamilton makes in like, a minute, you might consider that thirty grand is a lot for independent artists performing for ninety-minutes a night for forty nights to an average audience of thirty people.

Here are a few things worth mentioning about these tours:

1. Keep your audiences small. Counterintuitive, I know. Pop-up shows are, by nature, intimate and memorable and fun. The quality of engagement with people attending these shows can be off the charts. This translates into more merchandise sold at the end of an evening, and more people caring about what you do the next time you release a record, or come through town on tour again.

2. Let your fans do more for you. What significantly improved the Road Show’s bottom line was a sophisticated economic concept I once again most likely did not create: Tiered Ticketing Because We Need It To Make More Art. This is where you offer a reasonable base ticket price of say, $20, but give people two additional ticketing options: a Ticket + Love For The Road for $40 and a Ticket + Lots and Lots Of Love For The Road for $100.

I’m finding that people buy the more, and often, MOST expensive ticket. Even though all the tickets are the same! But why would they do that, Holly? Well, because they understand. How difficult it is to make a living as an independent artist. How often the very best ones of us eventually stop thinking about quitting and quit.

Giving people opportunities to do more for you is not asking for charity. It’s proof that what you’re doing is worth something.

3. Feed people. People love food as much as they love cats on the Internet. Considering that, this summer I decided to head out on tour with the perfectly melancholy Nashville-based songbird, Emma Swift AND a French-trained chef and founder of Underground Fine Dining, Dustin Brandt.

While Dustin serves a locally-sourced, seasonally appropriate, space-inspired tasting menu to a group of twenty to thirty guests, Emma and I sing a little bit. (Go ahead, think about that one episode of Portlandia with the chicken.) After the dishes have been washed, Dustin drives ahead to the next city, and Emma and I stay behind for another concert. We meet up with Dustin the following day, dinner is served, more singing, and so on and so on.

4. Be strategic with your routing. The United States is big. Instead of trying to cover every metropolitan statistical area, I thought it might be more reasonable to spend more time promoting more shows in a fewer number of cities. Having two to three days in one place not only breaks up some pretty hellacious drives, but it gives us opportunities to perform at radio stations and in record stores, hang up posters and pass out flyers, busk in pedestrian-heavy zones, fire up the social media, tour artisanal moonshine operations, flirt with cute baristas, meet with local city officials, score keys to the city, who knows!?

5. Collaborate. People want to be involved with creative projects, but they often don’t know how to get started. Simply talking with business owners you respect about what you’re doing will open up opportunities to work together.

I may have a leg up on this because I have a former career as a fundraiser, but I’ve been able to connect Dustin with local, organic farmers in each city to source all of the produce, dairy, and meat we will serve to our guests. Ann Arbor’s Zingerman’s Family of Businesses and San Francisco’s Ritual Coffee are helping with non-perishables, while Austin’s Deep Eddy Vodka and Topo Chico are crafting fancy cocktails at our events.

We have independent business owners like Daniel Sklaar with FINE & RAW Chocolate, Pamela Aflalo with Nutty Bunny Non-Diary Desserts, Stephen Judge with Schoolkids Records, Erica Belfiore with Zenality Yoga, and Ardent Recording Studios generously opening their facilities after-hours. There are former art museum curators, thespians, interior designers, visual artists, yoga teachers, and satellite-imaging analytic business development professionals welcoming us into their homes on school nights. With fifty people they’ve mostly never met. And, of course, the many fellow musicians like Robyn Hitchcock, Shelby Earl, and Amy Nelson joining us for sing-a-longs along the way.

Cross-promotion and pollination is a real thing. Be sincere and you will not go wrong.

6. Send thank you notes. With chocolate. For everything. Always.

My closing thought, so inspired by this profound teaching by Ira Glass, is that I want fewer of us to quit. (Unless you’re like, no really, it’s time to quit.) I’m not there yet, so I’m going to keep going. And I want to sweetly invite you to be a part of it. Also, I believe in you. And all the things you want to do. Be in touch. Maybe we can make pasta together one night.

For more information about Dream Dates, a national pop-up dinner and house concert series with Emma Swift, HOLLY, and Chef Dustin Brandt, visit

Photos: Daniel Marty

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