Book Jayson Gaignard through The Keynote Curators
Biography
Jayson Gaignard is an entrepreneur, author, community builder, and keynote speaker whose work challenges one of business culture’s most persistent myths: that successful people are self-made. For more than two decades, he has built businesses and cultivated meaningful relationships among entrepreneurs, helping leaders move beyond transactional networking to create communities grounded in trust, generosity, vulnerability, and genuine belonging.
Jayson Gaignard began experimenting with small businesses as a teenager and launched a personal concierge company at 19. After meeting a mentor who encouraged him to think bigger, he transitioned into e-commerce and became Canada’s second-largest concert ticket wholesaler. By 24, his company had achieved its first million-dollar month. Yet despite the financial success, he found himself deeply unfulfilled and eventually decided to wind down the business. The process left him more than $250,000 in debt, forcing him to rebuild both his career and his understanding of what meaningful success looks like.
That experience became the foundation for Mastermind Talks, or MMT, an invitation-only community for impact-driven entrepreneurs that Gaignard founded in 2013. More than 20,000 entrepreneurs from around the world have applied to join the community, which is limited to approximately 250 members annually. Through carefully curated gatherings and shared experiences, MMT helps entrepreneurs become better leaders, partners, friends, and contributors to their communities.
Jayson Gaignard is the author of Mastermind Dinners and Community Made: The Truth About Success and the Relationships That Create It. His work explores how people can identify the right relationships, nurture them with intention, build trust, and master the vulnerable art of asking for help. He also created the Community Made podcast and founded the Reach and Influence Mastermind, a peer group for entrepreneurs committed to sharing their hard-earned wisdom.
Named by Forbes as a “Top Networker to Watch,” Gaignard has delivered keynotes for organizations including Entrepreneurs’ Organization, Young Presidents’ Organization, and the U.S. military. Drawing from business success, financial collapse, personal struggle, and more than a decade of building high-trust entrepreneurial communities, he offers audiences a candid and practical perspective on relationships, resilience, leadership, and the power of asking for help. His central message is clear: extraordinary success is rarely achieved alone. It is community made.
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Videos
Speech TopicsExpand each topic to learn more
Why We Resist Asking for Help, and How to Break Through
Everything you want may be on the other side of a single ask. Yet it’s hard for almost all of us. There are patterns behind the resistance, and they run deep. Most leaders struggle to ask for help, and eight patterns explain why. Many wait until they reach a breaking point before circumstances force their hand. But you don’t have to — once you can name the resistance, you can do something about it.
You’ll leave with the ask you’ve been avoiding, the words to make it, and the system that turns your network into allies before the next crisis.
How to Turn the Connections You Have Into the Relationships You Want
You’re already in one of the most powerful organizations in the world. But access is just that. Access. You got in the room, but how you navigate on the inside is on you.
The challenge? Your calendar is already full. So investing the time to deepen relationships starts to feel like one more thing.
You’ll discover how to invest in those relationships with intention, how to nurture them at scale, and the small habits that compound into something extraordinary over time, without becoming another full-time job.
You’ll walk away with a clearer map of your current network, a system for staying meaningfully connected to the people who matter, and a clear next move for the connection you’ve been meaning to deepen — and haven’t.
How to Trust When the Stakes Are High
We’re taught that trust is a soft skill, and that it’s intuitive. This works most of the time — until it doesn’t. The cost of getting it wrong rarely shows up in the moment. It shows up years later, in the partnership that should have been a non-starter, the hire that nearly broke the company, the investment that went sideways.
You don’t need more instinct. You need a scorecard. A five-part framework for evaluating people when the stakes are too high to guess.
You’ll come away with a framework you can apply to your next big decision, a sharper read on the relationships already in your life, and the confidence to trust faster where it’s warranted — and slower where it’s not.
Testimonials
Booksby Jayson Gaignard
Mastermind Dinners: Build Lifelong Relationships by Connecting Experts, Influencers, and Linchpins
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Blog Posts
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Resilience Is a Cultural Contingency Plan, Not a Personal Trait
Every event planner knows the moment when resilience stops being a theory. At 7:12 a.m., the group chat lights up. The keynote’s flight is delayed. The ballroom doors open in 48 minutes. The sponsor wants...
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Are your values just posted on the wall? Keynote speaker McKain explains why living your values, not displaying them, is what keeps customers loyal.
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