G53: James Chapman

James Chapman is the Founder and CEO of Plain Sight, a social networking platform for like-minded people to connect with each other in virtual and physical spaces.

But this wasn’t his first foray into intentional networking. In 2015, he began an evening workspace for side hustlers to collaborate with each other, which led to the idea for his current startup. In 2017, he started and ran Detroit Demo Day, which has since provided over four million in funding to small businesses throughout the City of Detroit, the majority of which have been minority and women-owned. 

Chap has spent the bulk of his career creating spaces for ambitious people to come together, and it’s his way of giving back to the communities that helped him.

“I’m only where I am, really, because of the meaningful connections that I was able to make along the way, and what if I would have missed out on those? Like what if I didn’t have somebody to make introductions for me? And so, that’s what led to the idea for Plain Sight, is trying to solve that problem for people who are in shared spaces, hyper local, to be able to make meaningful connections with each other based on their needs.”

What Brett asks:

  • [01:45] What was it like for you as a young chap?
  • [12:54] How did you learn to get a hold of the less productive behaviors that were modeled for you as a kid, without losing the behaviors that can help?
  • [18:35] Tell me about your sister and your mom
  • [27:08] Was it always basketball? What energized you in this early stage of your life?
  • [32:30] What happens after you start dipping your toe in the entrepreneurial world?
  • [38:45] Tell me about working with Dan Gilbert.
  • [41:40] What has this last year been like for you?

Lessons for intentional living:

  • James learned a critical lesson in 2020: you have to make time and space to focus on your mental health. “Like that’s the number one thing that I’m going to be carrying into this year. Take your meditation practice seriously, take your fitness seriously, who you have conversations with and who you allow in your circle, and the energy that you allow people to bring upon you, take all of that very seriously. I deleted Facebook. I got rid of some friends out of my life that no longer serve a purpose in my journey and my development. And I was unapologetic about all of it.”
  • Too many people, kids especially, are labeled as either good or bad. But it’s kind of bullshit. Everybody is dealing with different things, and we all handle stress differently. Inversely, people don’t know what they don’t know — what you call “acting out” might be a valuable coping mechanism for a deeper issue. Changing this in our society is going to require intentional role modeling, especially from parents and teachers. We need to cut the labels out of our vernacular, start talking to people, and genuinely listening to learn about what’s really going on. It’s going to take a lot of time and practice, but I can’t imagine a greater gift to give the next generation.
  • James’s mentor taught him to bet on the jockey, not the horse. Because, if you find a jockey who’s obsessed with a problem, they’ll end up figuring it out.