Mastermind Talks

Jason Gaynard's journey to Mastermind Talks began unconventionally. After building a $6 million annual revenue e-commerce ticketing business (Tickets Candidate) over four years with no outside investment, he felt unfulfilled despite financial success. The turning point came when he attended a Seth Godin workshop in New York on the "connection economy"—the idea that there's massive value in connecting like-minded individuals. Jason realized entrepreneurs were among the most disconnected professionals, each working in isolation on their own ventures.

Instead of launching a scalable product, Jason started small with "mastermind dinners"—intimate gatherings of 6-8 entrepreneurs who didn't know each other. He'd cover the $600-$700 costs himself and facilitate introductions. These free dinners, held across North America starting in Toronto, became his testing ground. He built prospect lists from Canadian business magazines and cold emailed executives, initially achieving only a 5% response rate. Despite the low conversion, Jason saw the value and eventually wrote a book on his outreach methodology.

The pivot to events happened unexpectedly. Tim Ferriss was launching "The 4-Hour Chef" with no retail distribution—a crisis for a bestselling author two weeks before launch. Tim offered a "Hail Mary" package: buy 4,000 books, get two speaking engagements. Jason saw opportunity and spent $84,000 to secure Tim for two keynotes, which forced him into the event business.

For the first Mastermind Talks event in May 2013, Jason used two strategic philosophies. First, the "anchor tenant" approach: position a big-name speaker (Tim Ferriss) to attract other quality speakers and attendees. Second, "moving up the food chain": target the person most likely to say yes first, build social proof, then approach bigger names. Jason launched at $995 per ticket (friends said he couldn't get more than $1,000) and ran an "influencer blast"—getting all speakers to tweet the event to their networks within 48 hours. The event generated 4,200 applications for 150 spots. Jason personally reviewed every application to hand-select attendees, a non-scalable but high-quality approach.

The first event broke even with approximately $200,000 in revenue—not impressive on its surface, but Jason had proven the model worked and didn't need to repeat the $84,000 Tim Ferriss investment. The key insight came from an A/B test: when 100-200 prospects saw a $3,300 landing page instead of $1,000, sign-up rates remained identical, but attendee quality improved. This revealed massive pricing elasticity and led to Jason's core strategy: maintain intimate 150-person cap, increase price yearly, and focus on attendee quality over volume.

Instead of paying speakers six figures, Jason employed Peter Diamandis's X Prize model: award the best talk—voted by audience—$125,000. This turned speakers into competitors and attendees into judges, eliminating speaker costs while creating buzz.

By the time of this interview (approximately 2016, roughly three years after the first event), Mastermind Talks had grown to charge $6,000 per ticket. With 150 attendees, that's approximately $800K-$900K in pure ticket revenue per event, approaching $1 million when including sponsorships. The business has become "very, very profitable" with minimal marketing spend—Jason spent nothing on ads, relying entirely on relationships and word-of-mouth. He's leveraged his personal brand, built through association with figures like Ryan Holiday, Tim Ferriss, and Mark Echo, to attract both speakers and attendees without paid acquisition. The business operates with such high demand and lean economics that Jason can maintain his philosophy of quality over quantity indefinitely.