music career bets

How to advance your music career by taking little bets

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Building your music career shouldn’t require you to put yourself in debt. Use these three strategies to create affordable experiments to launch your act and your career.

“How can I succeed in music when I have little or no resources?” That’s one of the most common questions we get when we teach, lead music business workshops, or do presentations.

Being a musician today means being scrappy and resourceful. In a word, it’s about being entrepreneurial. One of the more inspiring stories we know of a start-up business that went from zero funds to a profitable business comes via a taco stand. The lessons you can draw from Guerrilla Tacos’ story also apply to your music career.

Going from $167 to success with “little bets”

Wes Avila started his business from practically nothing and built it into a success. Avila wasn’t making enough money working as a sous chef, so he came up with an idea on how he could earn more. But, rather than go all-in on the untested idea, he decided to make a little bet. He figured that if he could buy a small food cart, he could create and sell his unique tacos directly to customers on the street. He took his last $167 and bought a taco cart and the necessary ingredients and set out to test his idea. He called his business Guerrilla Tacos because he couldn’t afford the city permits. This required him to set up his cart in alleys and out-of-the-way places to avoid the authorities.

Although he got caught a few times, customers (and even the police who had to fine him) loved his tacos. Eventually, he made enough to purchase the necessary permits. By the time he purchased a full-sized food truck, he already had a solid, fanatical customer base, had honed his recipes, and knew his business model worked. He eventually got noticed by prize-winning food critics for his innovative recipes and it wasn’t long before he opened a brick-and-mortar restaurant. Since then, he has continued to expand with a coffee shop and, most recently, a restaurant in Japan.

Avila’s strategy of making “little bets” is one you can emulate with your music career by making small, affordable bets on yourself at each stage of your development. Each small test should grow your fan base, prove out which ideas work, and eventually give you the funding to grow.

There are at least three strategies we can draw from Avila’s story. Much of what he did comes from some of our favorite non-music business books, Little Bets by David Sims and Decisive by Chip and Dan Heath. If you choose your bets wisely, you can find out which ones are working for you and grow your music career based on actual successes.

1. Take little bets on your music career

In Little Bets, Sims suggests that ideas are great but they’re only valuable if you can test to see if they actually work in the real world. That’s exactly what Avila did when he bought his small food cart and took to the streets. He discovered pretty quickly which taco recipes worked and which didn’t based on what people ordered, and he adjusted his menu as he learned what they liked.

Use the same method by creating as many inexpensive real-world tests as you can to try out your ideas before you invest significant resources into them. There are dozens of low-cost — and even free — ways to get your music distributed, create and sell merch, generate royalties, and get publicity without paying a single dollar. Many services take a cut from the sale after the customer buys, so you can be profitable from the first dollar you make because it costs nothing up front. (These techniques are outlined in detail in our book, Making Money With Music, and they’re perfect for testing out your ideas.)

Making Money With Music

Most music businesses fail, not because the music is “bad” or the musician is flawed, but because the musician spends too much time or money without first testing out their ideas, music, merch, and more to see if they get traction. The time to place a bigger bet is after you find out what is actually working, and that’s easy to do with modest investments in merch and free or cheap music distribution.

Also, sometimes the world gives you suggestions of what to do next. For example, we never thought about licensing our own music until Disney came to us asking whether it could license one of our songs for a TV show. That led to us doing a lot of research before finalizing an agreement. That experience led us to proactively license other music in our catalog. Do what you can to make the most of every opportunity that presents itself.

2. Conduct small experiments (aka “ooching”)

The book Decisive introduces a concept called “ooching,” which means conducting small experiments. These experiments should not only be cheap or free, they must have feedback and metrics so you can evaluate the results of the experiment quickly and easily.

Avila used ooching as he honed his taco recipes. He’d attempt a new creation and see if it sold. We musicians can do this as well — not only with our music, but our website, merch, patronage rewards, and more.

For example, before our band, Beatnik Turtle, decided to take on our year-long “Song Of The Day” challenge years ago, we tested out, as a group, whether we could write and record six songs in one day. When we realized we could (and how much fun it was), that’s when we started seriously considering writing enough music to release a song every day for one year.

3. Use tripwires and time limits

Experiments can waste time and resources if you don’t know when to end them. Decisive lays out two techniques to help you avoid this: set a “tripwire” and/or set a time limit. A “tripwire” is an objective, easy-to-recognize trigger you can set — in advance — that will indicate if something isn’t working so you can stop and back out before you’ve sunk too much money and time into your experiment. Alternatively, you can set a time limit. If you cross a time deadline without seeing the result you were looking for, then it’s time to stop what you’re doing, reassess, and try something else.

Our band tried the tripwire method when we first started playing out live to see if our original songs worked and whether the covers we chose got the reaction we had hoped. We didn’t leap directly into booking shows at local venues. Instead, we signed up for open mics and open band nights. These required us to play just three songs and were perfect for testing different mini-sets to see which covers got the best response and which of our originals caught people’s attention. Only when we tested out all our mini-sets did we have enough information and felt confident to proceed to book our first big gig.

— — —

When you try out new ideas, remember to keep an open mind throughout the process. Look for results rather than successes and failures. Each experiment can teach you something, and what looks like a failure can give you a new idea or new way to do things. You know, the first hard pretzel was created because an inattentive apprentice baker overcooked the dough. Although he was nervous about the result, everyone found it delicious. Imagine if he had thrown it out instead of letting people taste it!

Authors of the critically-acclaimed modern classic, The Indie Band Survival Guide, Billboard Magazine called Randy Chertkow and Jason Feehan “the ideal mentors for aspiring indie musicians who want to navigate an ever-changing music industry.” Their latest book, Making Money With Music (Macmillan) and free Making Money With Music Newsletter, help all musicians — from startups to pros — build a sustainable music business so you can make money in today’s tech-driven music environment.

How to 
Make More Money With Music, the Complete Guide

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