While he now performs in multiple bands, teaches, runs a stage production company and curates a monthly studio session, trumpeter-singer-ukulele player Sam Thousand credits his hustle to his background as a teenage door-to-door vacuum salesman.

“When you have the opportunity to engage with people and to talk with them and show them why they’re actually in the market for your product, then it becomes an easy sell …” Trump said. “As an independent artist, I’m self-managed, self-produced and my own publicist and booking manager.”

After a soft release in November, Trump (born Samuel Harris III) debuted his first album, “Purple Skies,” in January. It’s a culmination of not only years of songwriting, but also reflections on his family and friends both close to and far from Chicago.

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