How Will Dailey Makes a Living as a Middle-Class Musician

Will Dailey’s music career began with a spatula and a tennis racket.

As a child, the Boston-area native would lead imaginary orchestras while listening to the classical music, show tunes, and Placido Domingo records his mother would play. The tennis racket was Dailey’s guitar until he got the real thing at age 12.

Now 38, Dailey has put out a number of albums over the past decade. He’s shared the stage with Dave Matthews, John Mellencamp, and Neil Young, collaborated with award-winning producer T-Bone Burnett, and had his music placed in a variety of TV shows and movies.

And in December, the three-time Boston Music Awards winner for Best Male Singer-Songwriter added two new BMAs to his collection: Artist of the Year and Album of the Year, the latter for his August 2014 release “National Throat.”

Yet despite all of this success, Dailey still considers himself a middle-class musician.

That’s not him criticizing his career to date, or some softball way of complaining that he hasn’t yet made it big. On the contrary: Dailey views middle-class musicians as vital to the economy, the music industry, and to art in general.

Music’s Middle Class

Being a middle-class musician is also an artistic choice, Dailey says. It’s a role he inhabits with pride. And with a clear vision and purpose.

“No one asks when you sit at these big music companies, ‘Do you want to be great? Or do you want to be famous?’ Because I would say, ‘I just want to be great and make things,'” he explains. “Being famous is a totally different art. It’s something else. You need a whole management system just to do that. It requires a certain set of skills that I didn’t want to have to work on or maintain.”

As a self-employed musician, Dailey is allowed to be the master of his own journey. He couldn’t say the same thing three years ago.

In 2011, after recording his sixth album, “Will Dailey and the Rivals,” a major label signed him to a five-record deal. But what would seem like a musician’s dream come true turned into a nightmare for Dailey.

He describes his relationship with the label as calamitous, and for the first time since kicking off his music career in 2004, Dailey felt his efforts were slipping backwards.

“The partnership just wasn’t healthy for me as an artist,” he says. “Their system was in turmoil, and I couldn’t make art amidst their turmoil. It was too corporate and too volatile… All of my champions got fired or transferred. I ended up working with someone who didn’t know me… It just wasn’t right for me.”

At his request, Dailey was released from his contract and freed to make an album on his own terms. In a sense, he was back where he started in 2004 — on his own in an ultra-competitive industry. But now he had a decade of experience to draw from, thousands of fans he’d worked hard to win, and some powerful new tools at his disposal.

Modern Patronage

In early 2013, Dailey rallied his fans, releasing a mission statement explaining his decision to fund his next album via PledgeMusic – a website similar to crowdfunding platforms Kickstarter or Indiegogo. PledgeMusic calls itself a direct-to-fan site, not a crowdfunding site; it’s focused solely on raising money for musicians, allowing them to pre-sell, market, and distribute music projects directly to fans.

Dailey considers the rise of such sites an important and liberating turn of events for middle-class musicians. Their existence allows everyday citizens to become patrons and funders of the art of their choosing.

“It’s the most exciting time to be making music,” says Dailey. “Music used to be made on a ‘golden ticket’, where people believed that if the right person heard you, great things could happen to you. What matters now are the customers you have as an artist — and I don’t mean just social media.”

Crowdfunding and the direct-to-fan movement have empowered fans and artists alike, he says, encouraging modern-day patrons of the arts who can share in the process of making great works of art.

“No one said Van Gogh was an incredible artist when he painted ‘Starry Night’,” Dailey says. “Van Gogh’s brother is the reason that it and Van Gogh’s other paintings exist. He funded his brother’s career. It’s the same thing now with music. The people have the power to create art.”

With backing from fans and patrons, Dailey raised enough money to record and produce an entirely independent record. The resulting album, “National Throat,” debuted in the top 20 on the Billboard Heatseekers chart when it was released in August. His latest music video, for the track “Castles of Pretending,” was debuted by the Wall Street Journal.

Dailey has had his share of ups and downs, but he’s shown how one can carve out a living as a successful middle-class musician. Here’s some of Dailey’s advice for musicians hoping to build a sustainable and rewarding career.

The Bread and Water Period

If music is in your blood and your sights are set on a career in the industry, be prepared to pay your dues and experience some lean times.

“The first thing I would say to artists in this business is that, just like any startup, there is a bread and water period,” offers Dailey. “And that could be anywhere from a year to five years.”

“If you are always working hard, and pushing it, you will yield results,” he adds. “But it’s not an overnight thing at all.”

Creating Art Still Requires Money

The cost of making an album can vary, but it’s rarely cheap. Dailey spent about $30,000 to create “National Throat.”

In addition to allowing fans to pre-order the album, Dailey offered dozens of other premiums fans could purchase to support the album, from lyric sheets he typed out on his 1931 typewriter to personalized cover songs to the opportunity to sing on the album.

That money paid for many things, including an audio engineer, mix engineer, mastering engineer, studio time, a CD duplication house, a vinyl duplication house, a Web designer, an artist to create the album artwork, another individual to do the album layout, and a small army of musicians.

Meanwhile, the process of crowdfunding an album can be intimidating, but also liberating. Dailey says to approach it with the right frame of mind: It’s not about how many followers you have, it’s about having the right followers, he says, and this is particularly true when raising money for an album.

Don’t worry about reaching thousands of people — worry about reaching the right people.

“This is very important, because we are taught that the more followers we have on social media, the better,” says Dailey. “No. You need the right people… 100 people is more important than 1,000 who don’t support you.”

It’s Not About the Golden Ticket

Many musicians still believe that having a long-lasting career as a musician requires that their music be heard by the right music industry executive, who will then take care of making everything else happen.

That approach, however, is no longer the only path to success, thanks to sites like PledgeMusic.

“Prior to this time period in music, it was about a golden ticket and maybe hiring an entertainment lawyer to shop you around, but now it’s all reflected in your hard work,” says Dailey.

Diversify

Dailey says diversifying your income streams is critical to making a living as a musician. “Diversifying is the key to staying afloat,” he says. “Everything is on the table. I have friends who are touring musicians, but they have a large group of students they give lessons to. There are always options for doing music full-time.”

He says his main income sources break down to: live performance, sales, royalties, producing other artists, publishing, sync with TV & film, exclusive specialty items (pledge items, for example), grants, and endorsements — and that they’re all important.

“To pay too much attention to one over the other leaves you defenseless in such a fluctuating and volatile industry,” Dailey says. “The key to survival is hustle, which, for me, comes from an obsessive love of the process of creating music.”

Taking Care of Business

As a solo artist, Dailey needs to manage and pay other musicians as if they’re employees, whether they’re touring bandmates or session players.

“I pay musicians per show and per session. I keep it on a flat rate, but they get paid no matter what the gig is, even though I don’t get paid for some gigs — like promotions, showcases, or in-store performances,” he says. “If it gets tight I communicate that to them.”

Keeping track of finances and tax information is challenging, Dailey admits. “It’s a weak spot. I have a system that works, but it could be better. I have a great accountant and she really cleans house once a year.”

His best tip: Using just one credit card for the business. “It gives us one report every quarter and we lead with that,” he says. “A business manager would be nice, but it is an expense that takes money out of my pocket right now that I still need for living and operating costs.”

There Are Few Days Off

Even with all of the awards and collaborations with famous artists, Dailey has yet to feel as though he can sit back and coast on his success, or not work hard each and every day.

If becoming a musician is your aim, he says, be prepared to work hard for the long haul, even after you’ve achieved a level of success.

“It’s the same thing for anybody who is starting a business — you have to work and work and work,” says Dailey. “There is no day where you sit back and say ‘Okay, I have enough money.'”

That work ethic isn’t about being greedy or constantly pursuing more money — it’s about always behaving like you’re operating a business, a livelihood that needs to be looked after and tended to regularly to maintain ongoing success.

“Some months are tight,” says Dailey. “It definitely happens. But you keep going forward. I will do this full-time until I can’t give it my all anymore. I found the one thing where, when it gets really tough and I get kicked down, I can get back up, year after year.”

“I’m still driving myself to gigs,” he adds. “We’re still a band in a van.”