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E204:The rise of community and the evolution of networking with James Chapman

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James Chapman is the Founder and CEO of Plain Sight, the best way to make connections wherever you go both online and in-person. He has dedicated the bulk of his career to creating space for ambitious people to thrive and come together. In 2015, he launched an evening workspace for side hustlers to collaborate which led to the idea of Plain Sight. In 2017, he started and ran Detroit Demo Day, which has lead to over $4mm in funding throughout the city of Detroit. The majority have been minority- and women-owned businesses.

Episode highlights:

  • What James credits for his success.
  • How James built up $1mm for a new business using networking.
  • How building relationships has changed due to the pandemic.
  • How James reinvented his business’s direction in 2020—after building it around people connecting in-person.
  • How connections happen with virtual events—what James has discovered.
  • How a rigidly structured connection is different for participants from a looser structure.
  • What has changed with communities in the last year?
  • What James recommends avoiding when building a community.
  • Best advice: Jump. Don’t wait.
  • Habit that contributes to success: Taking mental health seriously – including meditation.
  • Recommended tool: Twitter
  • Recommended book: The Motivation Manifesto by Brendon Burchard
  • Run time: 33:20



  • “They would rip up resumes… if they couldn’t pronounce their name.”
  • “With an early-stage business, people are betting on the jockey more than they’re betting on the horse.”
  • “Anybody can put together a pitch deck.”
  • “A meaningful relationship can’t be one-sided.”
  • “It’s made us a better company.”
  • “There’s that buffer space between attending an event and not attending an event.”
  • “It’s cool if you’re doing it while you’re in your pajamas.”
  • “I need community now more than ever.”
  • “Try to make sure you’re giving before you’re asking.”


  • Make sure connections benefit both parties.
  • Two words to make virtual connections better: curtation and intentionality.




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