SA 066: Jayson Gaignard on How to Build Authentic Relationships

Jayson Gaignard

Jayson Gaignard, entrepreneur and author of Mastermind Dinners, talks about starting a business and being in debt and how he changed his mindset to being value-driven; building a business he’s proud of, and how to build and cultivate authentic relationships.

Guest Bio:

Jayson Gaignard is a Canadian entrepreneur, networking specialist, and author who founded MastermindTalks, an invitation-only conference for entrepreneurs, in 2013.

Jayson dropped out of high school at the age of 17 and began working as an auto mechanic. In 2004, Jayson founded VIP Services Inc., a Toronto-based full-service concierge company. The company evolved into an online ticket seller and changed its name to Tickets Canada, which generated $5 million in annual sales.

In 2012, Jayson began curating dinners in Toronto, Canada with small groups of entrepreneurs that focused on relationship building. The invite-only dinners became MastermindTalks—larger conferences for entrepreneurs geared toward health, wealth, self-improvement, and networking. Past MastermindTalks speakers include Tim Ferriss, James Altucher, A. J. Jacobs, Esther Perel, Dave Asprey, Guy Kawasaki, and Marc Ecko. Forbes described Jayson as one of the top networkers to watch in 2015.


Some Questions We Ask:

  • When he hears the word successful, who’s the first person that comes to mind and why?
  • What does success mean to him?
  • Does he see this blue-collar mentality towards entrepreneurship from those coming from a blue-collar background in a lot of the entrepreneurs that you talk to on a constant basis?
  • Being a family-oriented guy, does he believe that we can balance drive and presence? Whether one’s an entrepreneur or just a person who has the drive and also wants to be there. Is there a balance there and how do we achieve it?
  • What books have most influenced him and why?
  • If he could have dinner with one person he admires, past or present, who would it be and why?

What You’ll Learn In This Episode:



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