How Former Bar and Restaurant Workers Take Over the Reins as Owners

Pouring drinks at Chicago’s Skylark always felt more like serving an extended family for Sam Mesick, who started working at the Pilsen dive bar 15 years ago. He witnessed regulars advance through various stages—from courtship and marriage to parents of toddlers who stood on chairs to reach pinball machine buttons. Other patrons brought him dinner when he worked on Thanksgiving. 

When Mesick, who lives above the bar, heard...