Stu Utgaard was the Twin Cities’ biggest dealmaker in the ’80s and ’90s, a master of M&A. Then he made his own acquisition, Sportsman’s Warehouse, and built a single store into a $718 million retail chain. So how did Utgaard wind up buried under $31 million in personal debt?

What would lure Mark Jacobs (Irwin Jacobs’ son) from Manhattan to Winona to run an old-fashioned door-to-door business? The chance to apply entrepreneurial liniment to a tired, aching brand.

Since meeting in the early 1980s and building Northwest Airlines’ WorldPerks frequent-flyer program, Mark Lacek and Peter Brennan have started five businesses, with a sixth on the way—nearly all devoted to helping businesses keep their customers coming back.