John Cain is a father and serial entrepreneur living his passion and empowering change-makers through Relentless MV. John and team have created a truly unique event that marries keynotes of world-class achievement, epic experiential adventures in a renowned location, a limited and referral-based attendee list, and a 3-day format to foster lasting connections. John visits the show to share more about his success-built-on-failure journey that led to Relentless MV and where it is going (literally) in the future.

“I grew up in a very low income setting and learned early on that…we’re in America…if you have a good attitude and work hard, surround yourself with the right people, and have optimism, work ethic, determination, resourcefulness you can reach great heights. You can accomplish amazing things.”

– John Cain

John is also the father of a young daughter and baby boy. We collaborate on parenting tips and John’s girl is joining my boy’s 2020 burpee challenge!


John Cain is a serial entrepreneur who has built, turned around and scaled various companies including a FinTech business, boutique hotel and whimsical, farm to table restaurant. His current passion project is Relentless MV, a unique keynote and experiential based event on Martha’s Vineyard for entrepreneurs, executives and change-makers.

John has a self-professed low tolerance for excuses and a lifelong passion for self improvement. As the proud father of a young daughter and as of just recently a baby boy, John is now not only working on himself but doing so from the perspective of a parent and coach of two Relentless children.


  • Unique and exclusive networking
  • Epic experiences
  • Empowering service to others
  • Purple cow extreme value
  • Failing forward
  • From nothing to everything




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