What happened: Jayson was a thriving entrepreneur—by outward accounts. Inside, he was lonely and isolated from others. He’d spent years working on his business and no time building relationships. After attending a workshop led by Seth Godin on the importance of connecting people, he cold calls big names from the pages of Profit Magazine until a handful RSVP to his dinner party. Inspired by Godin, he hoped to curb his loneliness and figured some company couldn’t hurt. A mix of nerves and imposter syndrome took hold; two hours prior to the event, he nearly cancelled. But in the end he didn’t. Eight entrepreneurs attended the first Mastermind Dinner in Toronto. Jayson is humbled and inspired by the company of like-minded leaders; he wants to continue bringing them together.
What we learned:Regardless of industry, entrepreneurs need a safe space to connect and remove the mask.
How we evolved:Jayson’s dinner was designed to make friends, not launch a company. It would go on to become one of the most exclusive communities for entrepreneurs in the world.
2013 A Business By Accident
What happened:Jayson borrows funds to buy 4,000 copies of Tim Ferriss’ just-released book, The 4-Hour Chef, part of a promotion that secures Ferriss as a speaker. Without much in the bank it was risky, but he jumped at the chance to re-create Mastermind Dinners on a bigger scale. He had no plans to start a business. Jayson and his wife Kandis turn MMT into an event that takes place over two days in Toronto. It was a TED Talk-style lineup with 15 speakers. On the final day, a big deal CEO was slated for the keynote Q&A. Jayson, embarrassed, stopped the session mid-way while volunteers herded people out of the lobby一the speaker couldn’t be heard over the din of conversation outside the room. Guests siphoned off into intimate groups, and even speakers stayed the full duration instead of ducking out after their time slots. Techvibes.com called MMT Toronto, “A two-day long dinner party in good company.”
What we learned: MMT closed the divide between the stage and the audience. Even the so-called “experts” mingled as guests, accessible for more casual chats, which was a huge draw. Entrepreneurs crave meaningful connections as much as content. MMT could fill that need. It had real business potential.
How we evolved: Conferences are everywhere, but real community is scarce. MMT would make meaningful connections possible, still leveraging community wisdom.
What happened: MMT Toronto, Part 2. To scale the concept of Ted Talks for entrepreneurs, Jayson and Kandis picked a big, historic venue. They made one change by adding small dinner parties the night before. Tables of six gathered at surrounding restaurants, and these intimate groups eased the awkwardness of meeting 150 strangers at once the following day. People let their guard down—and let loose.
It was the end of the night. Esther Perel found a piano in the venue’s lobby and accompanied by Jesse Elder on keys, broke into song — a rendition of Leonard Cohen’s Hallelujah. Everyone joined in. It was the perfect finale, and we couldn’t have planned it. Now we live for these unscripted moments.
What we learned: Mozart was right: “Music is not in the notes, but in the silence between.” Our differentiator wasn’t our agenda.
How we evolved: It was a matter of scalability (bigger crowds, bigger venues, bigger names) versus intimacy (curated company and unique, private locations that would still lure impressive guests). We chose intimacy.
What happened: MMT travels to its first international destination, Napa Valley. Less than two months out, inspired by the generous return policy at Zappos, Jayson and Kandis offered full refunds, plus $1,000 incentives. In the events industry, this is unheard of, but MMT has become more than an event. Cancellations weeded out indifference and boosted engagement for the right members, a highly curated group chosen by Jayson—good people who also happen to be good at business. Even with the lure of Yountville’s Michelin star restaurants and sprawling vineyards, refunds were risky. One person cancelled, begrudgingly, because of scheduling conflict. (He would have cancelled anyway).
What we learned: Attendees were mostly renewals or referrals. People came for the content and stayed for the Community. We had the right people, and a catalyst for future curation.
How we evolved: We leaned more into experiential events instead of one-way content. Great people. Fantastic food. Settings and content designed to inspire spontaneous creativityーbecause the best learning often happens between sessions. MMT would never be "just a conference."
2016 “I don’t know what I’m getting, but I’m going”
What happened: MMT Ojai sells out four months in advance—without a public agenda or named speakers. In previous years, guests voted on the top presentation, which came with a $25,000 prize. External speakers with high booking fees never won; members did. This time, sessions included member-led roundtables with some surprise guests. Gary Vaynerchuk was among them. Everyone was smitten with the serial entrepreneur and Chair of VaynerX, who showed up, seemingly out of nowhere, and herded everyone into a cavernous barn on the property. He was gracious enough to lead a three-hour Q&A under its vaulted rafters. Members knew none of this before they arrived. It was our highest-rated event to date.
What we learned: Members trusted us to provide value, even when they didn’t know what to expect.
How we evolved: Every event became a blank canvas. Locations change annually to create intrigue and strengthen the community through shared experiences that are both surprising and utterly unique. (In terms of scalability, this makes no sense but candidly, it keeps us from getting lazy.)
What happened: MMT partners with Defy Ventures, a non-profit that helps people transition out of the prison system. Four students from the organization’s entrepreneurship program received scholarships to attend MMT Carmel. A young man introduced himself: “I just finished 20 years for murder.” For a moment, the air left the room, but members focused more on his future plans than past mistakes.
Defy’s students are accomplished entrepreneurs. Like Coss Marte, who lost 70 pounds in solitary confinement after a doctor said his cholesterol levels could kill him before his release. Marte’s training regimen became a business, Conbody, now a trendy fitness bootcamp. On the final morning, MMT Member John Ruhlin had an idea—a charity auction to raise funds for Defy Ventures and a fellow member undergoing cancer treatment. Throughout the day, 25 items were donated, from coaching sessions to celebrity dinners. The group raised $300,000 in the first 15 minutes.
What we learned: When our Community flies in formation, it can be a powerful force for good.
How we evolved: A mindset shift for member curation meant focusing more on impact than outward success. Members now encourage and inspire each other to use their companies as catalysts for positive change.
What happened: At MMT Park City, one renowned member wasn't invited back. He pleaded ignorance when his inappropriate behavior wasn’t tolerated, saying the group’s values weren’t explicit. Jayson and Kandis grappled with defining core values and realized the Community should write its own. In Park City, members rallied to draft a set of guiding principles and vital behaviours. We didn’t need to create values—the Community was already living them—we only needed to uncover them.
What we learned: Curating a community of 150 people is like building a business of the same size. Hiring and firing decisions are based on values.
How we evolved: The Park City session defined our Guiding Principles, including a commitment to proactive generosity and endless curiosity. We still live by them to this day.
What happened: MMT Cabo broke the record for our highest-rated event. Members gave top marks after hearing from Jim Estill, who turned a small IT company into a $2 billion behemoth, then paid it forward. Estill told the Community about the Syrian families he welcomed to Canada in 2015. After watching the devastation of Syria’s civil war unfold on the news, he personally sponsored 300 refugees, covering expenses for their first year of settlement, as well as English classes and housing, even hiring some at his company.
What we learned: For the first time, we considered removing the cap on membership to grow the community’s positive impact. We hit our stride. Then came the pandemic.
What happened: On March 11, the WHO declared a global pandemic, and by early April, MMT Palmetto Bluff was postponed a full calendar year, to June 2021. Members were offered full refunds. If even 30 percent had taken this offer, we might have bled out. At a time of fear and uncertainty, while companies endured mass layoffs, no one gave up their spot. MMT had no revenue and no live event. All we had was our Community, and it was enough.
What we learned: The pandemic brought an incredible demonstration of loyalty that reaffirmed the strength of our Community. Even when nothing was stable, MMT was a guiding light.
How we evolved: The whole business pivoted to digital offerings, turning a three-day live event into ongoing, holistic support. Our core offering remained intact, but our format changed dramatically.
2021 Cast of Characters
What happened: MMT launches its first yearly membership model: one, three and five-year packages are built—some members jokingly ask for a lifetime option. Immediately, the Community was bought-in. With Covid-19 still restricting travel, MMT Palmetto Bluff was postponed again. Again, after being offered refunds, all members kept their spot.
What we learned: Good relationships are like good investments; they compound over time. This commitment to long-term value is reflected in our annual membership model.
How we evolved: Jayson and Kandis hired a full-time team for the first time. Staffing up was a risky move during a pandemic, but necessary to reimagine the business, re-establish format and scale the membership model.
Our virtual gatherings were lifelines at a time of forced isolation. Still, live events will always be our bread and butter.