Bob Andrews’s career in the music business started out as a lark. While the Nashville native was toiling away at a drum shop for seven bucks an hour, his friend Ken Coomer was drumming for alt-country heroes Uncle Tupelo. “I saw that Ken was having a good time on the road all of the time, and I thought it might be cool to do that, to travel around,” says Andrews. “So I bullshitted my way in.” He wrote to the band’s manager, Tony Margherita, touting his abilities as a drum and guitar technician; around the same time Uncle Tupelo’s road manager quit, and Andrews landed the gig. He moved to Saint Louis, where Margherita was based, in 1993.

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Within a couple years he’d gone from stringing guitars–for Uncle Tupelo and then Wilco–to pulling strings. In 1995, when Margherita moved to Chicago, Andrews took over as manager for another of his bands, the Bottle Rockets. “I didn’t really know what I was doing,” he admits. “I was just kind of faking it.” But since then, Andrews has moved to Chicago as well, and in recent years he’s emerged as something of an innovator in the industry. He’s now one of the principals at Undertow Chicago, a management company, record label, and booking agency that’s tackling its multiple functions with unusual synchronicity. When a band is successful enough to need a label, a booking agent, and a manager, three separate parties normally handle those tasks–and if they don’t communicate well, the band suffers. But in the last year and a half Undertow has developed a model where one team–Andrews and booking agent Meggean Ward–can theoretically take care of everything.

In 1997 he waded in further when Nadine couldn’t find a U.S. label to release their first album. A mutual friend, Mark Ray, operated a modest studio and rehearsal space called Undertow; Ray, who earns his living as a designer at an ad agency, laid out the artwork and lent them some equipment and the name, and that year Undertow released its first album, Nadine’s Back to My Senses. The record sold 1,000 copies in the U.S., mostly at shows, and in 1999 Undertow decided to release another.

Dawson’s not worried about anything like that happening with Undertow. “I completely trust Bob,” he says. “There’s not a doubt in my mind that he would never do anything that would hurt the band, whereas with pretty much anyone in the music business there’s always a thought that this person is going to screw me over eventually.” He also appreciates Undertow’s integrated approach. “At this point there’s not much difference between management and the record label because they’re all trying to target the same stuff. I don’t think [Bob] needs to make phone calls as manager and then go ahead and make phone calls as label guy. It’s the same thing now.”