Rob Kessler, a Second-Generation Entrepreneur, Marks a Dozen Years of Innovation, Success, and Struggle

Like father, like son, entrepreneur Rob Kessler is a talented and ambitious business owner. His company, goTIELESS, has just passed a dozen years of marketing a brand of shirts with proprietary inserts [Million Dollar Collar] designed to be worn without ties.

Rob is the son of Richard Kessler, who for 35 years reigned as the diamond engagement ring “King” in Wisconsin and was one of the very first guests this podcast showcased when it launched in June 2012.

Among the insights you’ll hear listening to Rob are:

• Adapt or die

• Bet on yourself

• Start lean

• Serve obsessively

Rob’s path has been different than his dad’s. You might say he’s still a diamond in the rough. Yet Rob’s experience, as he shares this week, offers a study in entrepreneurial persistence, innovation, and market adaptation.

Monday Morning Radio is hosted by the father-son duo of Dean and Maxwell Rotbart.

Photo: Rob Kessler, goTIELESS
Posted: May 26, 2025
Monday Morning Run Time: 42:53
Episode: 13.47

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