The music business’ favorite blowhard is being matched up with a longtime label boss in a six-city series booked by WME’s Marc Geiger.

There’s two prevailing mysteries about writer, podcaster and SiriusXM host Bob Lefsetz — where does he make his money, and where does he come up with some of the outrageous things he emotes through his Lefsetz Letter, which’s he’s written since the late 1980s and freely distributed, first through fax and then through email and the Internet.

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Lefsetz’s daily columns (or “screeds” depending on who you ask) are read by the some of the biggest movers in music — Michael Rapino counts himself as a reader, as does WME’s head of music Marc Geiger. And now that Lefsetz is expanding into podcasting and a show on SiriusXM Volume (channel 106), it seemed like the right time to take the Lefsetz show on the road with music industry veteran and podcaster Jason Flom on a six-date U.S. and Canada Tour beginning Saturday at the Tsai Center at Boston University. Tickets are $30 plus fees.

“My thought was that if Malcolm Gladwell is going on the road doing podcasts and Pod Save America is selling out, there’s a good possibility that these guys, who everybody reads, have an audience of people who want to ask them questions and see what they look like in person,” Geiger explains. “Plus there are music industry people that want to see this. So we are doing a small run to see how Bob and Jason enjoy it and if the audience enjoys it, and we’ll go from there.”

While Lefsetz is sometimes brutish with his opinions and over-bearing with his thought experiments, Flom makes for a good juxtaposition, coming off as thoughtful and even keeled in a recent podcast the two taped together. Flom is of course the same Jason Flom of Atlantic Records and Capitol Music Group fame, considered to be “one of the most successful record men of the past 20 years…known for his specialty in delivering ‘monsters,'” according to the New Yorker. Flom now runs Lava Records with artists that include Lorde, Greta Van Fleet and Jesse J. He also serves as founding board member of the Innocence Project, where he’s long championed criminal justice reform issue and serves as the host of the podcast Wrongful Conviction, which is now on its seventh season.

The pair will preview Lefsetz vs. Flom on Oct. 15, for a SiriusXM segment that will air in its entirety on Volume Oct. 17 at 7pm Eastern. Flom said his event with Lefsetz will be part deep dive discussion, part heated debate over issues like the future of the music, the role of culture in shaping society and Bob’s controversial remarks on everything from the Me Too movement (“the average male is wincing, wondering whether we should take our heterosexual clues from gay people,” Lefsetz wrote in August) to the politics of Taylor Swift, where he recently explained “Democrats are wimps who believe in their hearts they’re on the right side and should win and when they don’t they whine. GROW A PAIR!”

Flom said he disagrees with many of Bob’s views, but said “when you write as many words as he does this, there’s going to be things that piss off everybody. And sometimes that’s the complaint — he writes too damn much and you can’t read it all.”

Expect Lefsetz to be both provocative and introspective, Flom says, with few softballs but plenty of room to deep dive into uncomfortable topics, covering everything from why artists need to stop complaining about how much they are getting paid by Spotify to how “men of a certain age” make peace with aloof fathers who never tell their adult children they love them.

“People know what they are getting with Bob because they read his stuff and see how he is putting himself out there,” Flom says. “Whether or not you agree doesn’t really matter to Bob. He is an extremely curious person and he’s looking for the truth, not angling for a job at a record company or anywhere else.”

How Lefsetz earns a living is a bit a of a mystery, since he doesn’t charge for his letter or podcast and doesn’t accept advertisers. He makes a little money speaking at conferences and special events and hosting his show on SiriusXM, according to friends. Does that mean he works as hard as Flom, who runs a record label, hosts a popular podcast and has given millions to charity?

“In his mind, yes he does,” jokes Geiger.

But what a helluva mind it is. Dates for the entire six-city tour are below:

Oct. 13 — Boston @ Tsai Center at Boston University (tickets)

Oct. 14 — Toronto @ Phoenix Concert Theatre (tickets)

Oct. 16 — Brooklyn @ Rough Trade (tickets)

Oct. 18 — New York @ The Loft at City Winery (tickets)

Oct. 29 — Los Angeles @ The Regent (tickets)

Oct 30 — San Francisco @ Great American Music Hall (tickets)

This story originally appeared in Billboard.