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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After more than 15 years as an executive at Meta, eBay, and Target, Anya Cheng set out to launch her own venture, Taelor. Her company uses artificial intelligence and personalized styling to rent clothing to men who dislike shopping, but need to look put-together for professional and social occasions.

As she candidly shares this week, her two-year-old company has encountered a full buffet of challenges — from limited resources, both financial and human, to the steep personal transition of relying entirely on her own judgment.

Drawing from her successes and missteps, Anya offers ten actionable recommendations that every new and most established businesses should heed. Be sure to have a tablet or pen available to take notes.

Above all else, Anya’s journey underscores the grit and adaptability required to build and maintain a new business in today’s startup landscape.

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

Photo: Anya Cheng, Taelor
Posted: May 19, 2025
Monday Morning Run Time: 47:07
Episode: 13.46

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• Founder Mike Frick and His Family-Owned Company Embody All-American Values

• Lessons in Branding, Scaling, Adaptability, and International Relationship-Building

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Business owners and entrepreneurs who mess up royally might take cold comfort in Al Lewis’s Substack, BusinessBlunders.com, which regularly details the boneheaded choices and outright illegal antics of a rogues gallery of today’s and yesteryear’s CEOs and senior executives.

For most readers, Al’s independent newsletter is an opportunity to learn from other people’s mistakes, which is, as he puts it, “is a lot less costly than learning from your own.”

Among his recent posts is an article titled Lost In Love: Top CEOs who kissed away their jobs, featuring, among others, Kohl’s CEO Ashley Buchanan, BP CEO Bernard Looney, and McDonald’s CEO Steve Easterbrook.

Al is a veteran journalist and editor, having served as business editor of the Houston Chronicle and The Denver Post, and Markets Editor at CNBC.

You won’t want to miss this episode. Doing so would be a business blunder of the first order.

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

Photo: Al Lewis, BusinessBlunders.com
Posted: May 12, 2025
Monday Morning Run Time: 50:25
Episode: 13.45

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Can a timber-framed cottage built in tiny Frogholt, England, in 1450 and its current occupant and owner teach 21st-century business executives and entrepreneurs valuable insights about leadership and collaboration? Absolutely.

Douglas Squirrel, who goes by the mononym “Squirrel,” is a multi-decade technology trailblazer and business scale-up expert. He uses his home, Old Kent Cottage, which required extensive restoration help from plumbers, electricians, structural engineers, and thatchers, as a practical business case study in managing complexity and as a metaphor for demonstrating that those with diverse skills must collaborate harmoniously or risk structural failure.  

As Squirrel explains, if the many artisans who worked on Old Kent Cottage hadn’t communicated and worked together closely, the roof would have fallen in. 

It’s the same, he says, with every business.

Squirrel is a proponent of using the human power of conversation to build effective, high-performing teams that lead to “insane” profits. Along with Jeffrey Fredrick, he wrote a seminal book on the topic, Agile Conversations: Transform Your Conversations, Transform Your Culture. Squirrel is also the author of Squirrel's Tech Radar, which is available from Amazon UK.

“You should be really curious about technology all the time, because there's nothing else that's moving as fast and that is changing the landscape of your business as quickly as the technological innovations,” he says. 

Squirrel chairs the Squirrel Squadron, a free-to-join global online community of diverse technical and non-technical executives who learn from one another.

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

Photo: Douglas Squirrel, Squirrel Squadron
Posted: May 5, 2025
Monday Morning Run Time: 57:10
Episode: 13.44