Executive InsightsChris Bakes headshot

Thoughts & Perspectives from Chris Bakes

Real‑world stories, personal commentary, and everyday insights on business, family, sports, tech, and whatever else deserves a good conversation.

 

These are the stories I’d tell you over coffee — business lessons, family moments, real-world insurance insights, and the occasional obsession with Teslas, baseball, or whatever else grabs my brain at 4 AM.

 

Business Leadership

Chris Bakes and his sons Brayden and Ryan during the 2026 Illinois State Redbirds baseball season.

5 min read

Baseball, Business, and Fatherhood: The Long Game Continues

The end of a baseball season is never easy. No matter how it ends, you always find yourself looking back. The wins, the losses, the stretches where...

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The featured image behind Chris Bakes's Executive Insights essay on allies, family, and the team behind every win.

3 min read

Winning Is a Team Sport: The Allies Behind Every Goal

I was traveling recently to watch my boys play baseball and, like I usually do on long drives, I had an audiobook playing. This time it was Winning...

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A split-era collage showing a Blockbuster store, VHS tapes, and a flip phone transitioning into a Tesla in self-driving mode, AI tools on a laptop, and modern smart rings.

4 min read

From Blockbuster Nights to AI Running My Day: The Evolution of Tech

The Evolution of Technology and What It Means for the Next 45 Years Last weekend I was cruising from Chicago to Eastern Kentucky in my Tesla in full...

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Chris Bakes's twin sons in their high school baseball uniforms, the image behind his Executive Insights essay on baseball, business, and fatherhood.

4 min read

Baseball, Business, and Fatherhood: The Long Game

Friday, February 13th is opening day for my twins, and it’ll be the first time I get to watch them take the field together in a college uniform....

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