Along with John Mayer's manager Irving Azoff, Cahill helped put together Dead & Co., a touring band consisting of former Grateful Dead members Bob Weir, Mickey Hart and Bill Kreutzmann, along with Mayer, Oteil Burbridge and Jeff Chimenti.
"We had the benefit of deep state Grateful Dead folks who would not let me fuck up and they would tell me where the bodies are buried and help us," continued Cahill. "Our first mandate when we started working with them was to protect 50 years of equity in the music space, from the songbook to how they deliver on stage. We approached it by protecting what was built and by working with some of the great people that are already around it."
Cahill went on to explain that there was reticence from the protective following of Deadheads, but those involved in creating Dead & Co. had the benefit of seeing the rehearsals and the chemistry between Weir and Mayer.
"We knew that the community, if they give it a chance, would embrace it because it was authentic and real and you couldn't deny what [Dead & Co.] were doing up there," said Cahill. "It was and is magical."
Cahill went on to confirm that the idea for Mayer to play with the former members of the Grateful Dead came when Mayer performed with Weir while filling in as host on the The Late Late Show before James Corden took over in 2014.
"John doesn't get enough credit," Cahill told the audience at the Montage Hotel in Beverly Hills. "He showed up ready with a binder on the first day of rehearsals for Dead and Co. I think it was three pages per song and he knew 20 plus songs cold, and in Dead world a song can be a 20-minute exercise. It shows his respect for the materials, respect for the guys and how serious he took it."
Cahill, who left Roar management with co-founder Greg Suess in April to start Activist Artists Management, was also asked about specifically working with bands who excelled at live performances.
"Most of your acts are known for their live show. Is that what you look for first?" Steinberg asked.
Activist Artists Management has recently signed highly coveted live band The Lumineers and Cahill had a hand in putting together a package with long time client Dwight Yoakam, Lucinda Williams and Steve Earle calling the tour LSD.
"One hundred percent. We are a boutique management firm. We're very hands on. We have a small group of clients that we throw the kitchen sink behind," Cahill responded. "We won't even take a signing meeting if we haven't seen the act live."
Cahill also worked for years with Zac Brown, who recently left Activist Artists Management.
"You discovered Zac Brown early on and he is not your typical country star. From the beanie to the beard, he's not your stereotypical superstar," said Steinberg. "How did you know there was more than meets the eyes?"
"Zac, if you meet him, you know right away that he is a force of nature," said Cahill, who connected with Brown after his appearance on cruise ship festival, Rock Boat. "Zac would play for four hours and then go to the bar and play another five hours. He created a bit of a legend and everyone was aware of not just his artistry, but how hard of a worker he was."
"You were involved very early before that first record [Zac Brown] broke. You took them all the way to selling out three nights at Fenway Park in Boston and then he left you. As a manager, how are you not curled up in the fetal position after losing an act like that?" Steinberg asked.
"Any manager that acts like that's not a punch to the stomach would be full of it, particularly when you believe in somebody," Cahill answered. "The interesting way that losing a client manifests is that you wake up the next day and you're no longer selling or preaching the gospel of that client."
Cahill added: "I was very proud that when Zac went in-house [with his management] that nobody [at Activist] lost their job. In fact, we had a couple of hires that we brought in."
"I think a lot of people pretend it's not part of the normal business, but I don't think there's any manager, even a promoter that hasn't lost their share of acts. It is part of a long-term career," said Steinberg.
"If you're in the game long enough, you're probably going to have this happen," Cahill replied. "We'd all love to be [John] Landau and [Bruce] Springsteen. I think in this era it's more difficult to have that kind of relationship, but it's what we all aspire to."