Living in the Year 1450 (Sort of), Douglas Squirrel Bridges the Tech-Nontech Divide

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