The Business of Being Derek Webb
How one working-class musician rewrote the rules, walked away from the industry—and built a 30-year career from the ground up.
Derek Webb doesn’t need your record label. He doesn’t need a booking agent. And he definitely doesn’t need your radius clause.
What he does need—and what he’s spent the better part of three decades obsessively building—is a direct relationship with his fans. Because in Derek Webb’s world, intimacy isn’t a luxury. It’s the business model.
“I’m not famous,” he told a room full of students at Middle Tennessee State University. “I’m a niche within a niche. But I’ve been making a living at music for 30 years.”
That longevity is no accident. It’s the product of relentless reinvention, creative audacity, and a willingness to treat the so-called rules of the music industry as nothing more than polite suggestions.
From Trunks to Email Lists
Webb got his start in the early ’90s in Houston, selling CDs out of car trunks and touring on credit cards. His band, Caedmon’s Call, eventually signed to Warner and dominated the Christian music scene. But even as the band found success, Webb began questioning the labels that had been slapped onto his art.
“There’s no such thing as a Christian iPad,” he says. “Christian is not an adjective that makes sense for objects. It’s a marketing term.”
In 2003, frustrated by the limits of traditional promotion, Webb tried something radical: he gave away his album for free—in exchange for an email address and a zip code.
At the time, the industry was still suing fans for piracy. Streaming didn’t exist. Giving music away for free was blasphemy. But Webb understood something the suits didn’t: data was worth more than dollars.
In three months, he went from 5,000 email addresses to over 100,000. And when he noticed he had 2,000 fans within 20 miles of L.A.—a city he'd never successfully played—he booked a no-guarantee show in the basement of the Knitting Factory. He sold it out. Then played a second set on the sidewalk for the 200 people turned away.
That night changed his career. And it was just the beginning.
NoiseTrade: From Idea to Exit
What worked for Webb could work for others. So in 2008, he launched NoiseTrade, a platform that let artists give away their music in exchange for fan data.
NoiseTrade helped launch bands like The Civil Wars and The Lumineers. Eventually, it was acquired by PledgeMusic (RIP), and Webb found himself exiting a company he built on the same principles that had reshaped his own career.
His big takeaway? “First-party data is still king.”
The House Show Hustle
While most artists dream of selling out stadiums, Webb makes his money in living rooms.
“I play 6–8 house shows a month. No sound check. No venue cut. Just a room full of people who care.”
Tickets are $20. He sells out almost every night. Hosts volunteer their homes for free. He plays two weekends a month, makes $6,000–$10,000, and never gives a penny to Live Nation. He also sells merch—QR codes on the kitchen table—and stays long enough to shake hands and say thanks.
The result? He’s built something bigger than a fanbase. He’s built a community.
Patreon, Emails, and Intimacy at Scale
Webb now makes his primary income from Patreon, email, and direct-to-fan relationships. His emails are hand-typed. No templates. No images. Just him, being real.
“I’m in the intimacy business,” he says. “I tried all the best practices—beautiful email designs, perfect templates. My open rates went down. Then I started writing like it was 2am and I was emailing a friend. My numbers doubled.”
He’s fiercely loyal to ConvertKit (now Kit), combs his list every six months, and deletes deadweight. “I used to have 100,000 emails. Now it’s more like 40,000—but they’re healthy. They open. They click. They care.”
Survival Songs
Webb’s latest record, Survival Songs, was born out of both love and fear. He has queer and trans loved ones, and in the current sociopolitical climate, he’s afraid for their lives.
“I can take the heat. I’ve toured with drag queens. But this is my family.”
He went home and wrote the entire album in a week. Tracked it on a $400 Tascam 12-track in a borrowed Airbnb. Mixed it himself. Total cost: $650.
“It’s the best record I’ve ever made. Not because it’s perfect. But because it’s the most true.”
Faith, Fallout, and Rewriting the Story
Webb isn’t afraid of controversy. He used to be a leading figure in Christian music. Now he’s a progressive provocateur with a penchant for challenging the same systems that once fed him.
“I’m not the guy who wrote those old songs anymore. But I trust that younger version of me did the best he could with what he knew.”
He reposts his hate mail. Uses right-wing outrage as marketing fuel. When Matt Walsh called him dangerous, Webb’s response was simple: “What a gift.”
A Final Word
Every month, Webb thinks about quitting. But then he has an idea. Or his kid inspires a song. Or he plays a house show that reminds him why he does this.
“This is a lemonade stand,” he says. “You have to reinvent it every month. That’s the work.”
All things DW can be found here.
This story is part of A Minor In Reality, a series on the messy, magical leap from 0 to 1. Built for founders—both for-profit and nonprofit—these are real conversations with real builders.