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James Chapman is Founder and CEO of Plain Sight, a company that helps you make the right connections at events and workspaces, or connect online from anywhere.

James started as an aspiring NBA player from Chattanooga Tennessee. He made it to the NBA’s D-league, but that’s where that dream ended, and the next season began. Basketball’s loss was entrepreneurship’s gain. James started loading boxes for FedEx. His hustle led him to new opportunities, and eventually starting two different businesses. All along the way sharing his amazing hustle inspiration on Twitter, later turning the collection into a book, aptly named #TheHustle. But it was a chance to work with legendary Detroit businessman Dan Gilbert that led to his 3rd startup journey, Plain Sight.

James has a great story. You’ll want to listen in.


…you got to keep showing up, no matter what…
~ James Chapman

In this episode James and Dan discussed:

  • growing up a passionate athlete
  • going from the basketball court to the warehouse
  • hard lessons from his first startup
  • insights from running a coworking space
  • his connection to Dan Gilbert
  • why Plain Sight has no profile pictures



“ we launched this five months before the starter was global pandemic.
~ James Chapman


“ there are some pretty crappy people in the world that legit do not like you because of something that is beyond your control…the color of your skin.
~ James Chapman