How I Made It: Bob Lefsetz went from failed music manager to one of the most influential voices in the industry

The gig: Bob Lefsetz is not your average music blogger. In fact, referring to him as merely a blogger probably does him a disservice. He’s more of an industry guru.

Unlike most music publications, the Lefsetz Letter — Lefsetz’s independently produced email newsletter featuring his irreverent, often boisterous take on the business of popular music — is read by just about everyone who’s anyone in the music industry.

Lefsetz’s pointed analysis of industry trends, along with his free-ranging thoughts on topics as diverse as politics and tech, have helped him become one of the most influential voices in the music business.

Lefsetz makes all of his writing available for free online. And in lieu of charging a subscription fee, he earns a comfortable living parlaying his notoriety into paid speaking arrangements and writing for publications such as Variety.

A dream: Lefsetz, 64, grew up in Fairfield, Conn., in the late 1960s when he says “music defined the culture.” He enrolled in Middlebury College in Vermont, and after getting an A on an English paper titled “Consolidated Stuffed Nose Or That’s the Way the Joint Rolls” about Thomas Mann’s novel “Confessions of Felix Kroll, Confidence Man,” he decided that he wanted to be a music writer and dreamed of working for Rolling Stone in San Francisco.

“I called my mother and told her I wanted to be a writer and she laughed,” he said.

But when a creative writing professor told him his writing was lacking, he became discouraged and vowed to stop writing altogether. After graduation, he moved to Utah and became a ski bum for a few years before enrolling in Southwestern Law School in Los Angeles. He landed a job as a music business attorney in L.A., figuring his law degree would give him a leg up in an industry that in the 1970s was run by lawyers.

An epiphany: Lefsetz eventually wound up as the U.S. manager for U.K.-based record label Sanctuary, overseeing heavy metal acts such as W.A.S.P. and Iron Maiden. After being fired over a disagreement with W.A.S.P. front man Blackie Lawless about which song to release as a single, he found himself running out of money and flipping through a copy of Billboard Magazine at a burger joint on the corner of Pico and Sepulveda when he came to a realization.

“I’m reading this and I go, ‘This is terrible, I can do a better job than this,’” Lefsetz said. He did some research and decided to start a newsletter providing the kind of thoughtful industry-wide analysis he believed the music trade magazines were missing. “I woke up my girlfriend and said, ‘Hey, I have this idea.’ And she said, ‘Well, you should do it.’”

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Perseverance: The year was 1986, and to get the newsletter off the ground, Lefsetz charged a brand-new Macintosh computer to his credit card. He entered 3,000 names and addresses taken from a music industry directory into a database program, printed copies of the newsletter on his dot matrix printer and mailed three free issues to each address soliciting a subscription.

The newsletter was made up of six to eight typed pages dissecting the music business. Once he gained paid subscribers, he worked diligently to grow his readership.

“No one has the perseverance I have,” Lefsetz said. “When I took people’s money for subscriptions and I told them the newsletter would come out every two weeks, it came out every two weeks, to the day.”

Despite his relatively low profile in the industry, music executives quickly took notice. “Generally speaking, only the most successful people in the music business subscribed,” he said.

Bob Lefsetz says that people read his newsletter looking for his honest opinion and ability to cut through music industry hype. (Glenn Koenig / Los Angeles Times)

(Glenn Koenig / Los Angeles Times / Glenn Koenig / Los Angeles Times)

Going online: In 2000, Lefsetz took the newsletter online and did away with the paid subscription. Around the same time, file-sharing service Napster was putting huge swaths of the record labels’ music catalog online for free, and Lefsetz recognized the coming sea change. “I certainly know that I alerted everyone in music business to tech when they were completely out of the loop,” he said.

As his subscriber base grew online, so did his status as true music biz insider. Lefsetz can now be found hanging out backstage at the Aspen Live music summit or trading emails with such prominent music executives as Lucian Grainge and Jay Marciano. Today, most of his income comes from paid speaking opportunities at industry conferences and events. (He declined to reveal how much he charges).

“I’m not part of the fraternity of writers,” Lefsetz said. “I’m also not in the world of journalism. I hang with the musicians and I hang with the business people.”

Why you gotta be so mean? Lefsetz is nothing if not opinionated. And he isn’t afraid to upset anybody, including some of the industry’s biggest acts, with what he writes. Criticisms leveled in his newsletter have sparked a number of high-profile public feuds, including with Gene Simmons, Kid Rock and most famously, Taylor Swift.

When Swift was a budding country star, Lefsetz championed her authentic songwriting and the two exchanged a few emails and phone calls. But after a poor performance at the Grammys in 2010, Lefsetz wrote what he says many in the industry had been telling him — that Swift couldn’t sing.

In response, Swift released her hit single “Mean,” written allegedly about Lefsetz.

Lefsetz doesn’t regret writing about Swift and says that people read his newsletter looking for his honest opinion and ability to cut through industry hype.

“This is show business, not show friends,” he said.

Power of the pen: In an industry where Lefsetz says everybody is on somebody’s payroll, his greatest asset is that he’s not beholden to any label or publication. When he questions executive salaries paid to figures such as the legendary concert promoter Irving Azoff, he means it. And when he urges readers to check out a YouTube video of up-and-coming country-folk singer John Moreland, he’s just as sincere.

“We live in a world where the biggest stars in America wouldn’t come out in the election,” Lefsetz said. “So I’m being a guy who speaks truth to power. That is my opinion and that is the power of the pen.”

Lefsetz says his only goal is to expand his readership, increase his influence and maybe enjoy a few of the perks that come with being an industry insider.

“I do it as an artist would do it, not as a businessman would do it,” he said.