LU 320: How Entrepreneur Jayson Gaignard Went from $250K in Debt to Hosting an $84K Event with Tim Ferriss (podcast) With Jayson Gaignard

Hey everyone! In today’s episode, I share the mic with Jayson Gaignard who is a Canadian entrepreneur, super-connector, author and Founder of Mastermind Talks (MMT), an invitation-only conference for entrepreneurs.

Tune in to hear how Jayson pulled off an $84,000 opportunity to host an event with Tim Ferriss, how you should be hosting successful masterminds and how Jayson reaps the many ROI benefits from strong relationships he’s nurtured.

Jayson Gaignard


  • [00:41] Before we jump into today’s interview, please rate, review, and subscribe to the Leveling Up Podcast!
  • [01:35] Jayson’s story and what lead him to where he is today.
  • [02:23] The business that landed Jayson a quarter of a million dollars in debt.
  • [03:24] A transformational experience at Seth Godin’s workshop.
  • [04:15] When Jayson first started to host his Mastermind Dinners.
  • [05:48] How Jayson pulled off an $84,000 opportunity to host an event with Tim Ferriss.
  • [07:55] Transition and evolution of the Mastermind Talk events.
  • [08:40] The economics and profitability of the Mastermind Talks business.
  • [09:43] An overview of the complete Mastermind Talks experience.
  • [11:29] Jayson’s focus on scaling community trust rather than business revenue.
  • [14:02] The intimacy and strong relationships within the MMT community.
  • [17:05] Unforeseen benefits and case studies from Jayson’s Mastermind Dinners.
  • [18:38] Jayson’s $10,000 leap of faith attending Tim Ferriss’ event, Opening the Kimono.
  • [21:37] The process Jayson follows for nurturing relationships and staying in touch.
  • [23:24] Why Jayson capped Mastermind Talks to 150 people initially.
  • [25:27] The five types of connections: fringe, fans, community, connectors, and core.
  • [29:48] Jayson’s reason for disliking the question “How can I help you?”
  • [31:26] Making the most out of a mentor relationship; uncovering their incredible value.
  • [31:57] Why Jayson turns down the opportunity to go to Richard Branson’s island.
  • [35:35] Top 3 Do’s and don’ts of hosting a successful mastermind dinner.
  • [39:29] Two schools of thought: charging for mastermind dinners or not.
  • [42:06] One new tool that Jayson has added to his life.
  • [43:56] Jayson recommends the book Seeking Wisdom, by Peter Bevelin.

Resources From The Interview:

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