Mastermind Dinners

Mastermind Dinners Plot Summary

Introduction

I still remember the first dinner I ever hosted. My hands trembled as I arranged the place settings, wondering if anyone would even show up. I had invited eight entrepreneurs who didn't know each other but shared similar challenges. As they began to arrive, I noticed something magical happening—connections forming before my eyes. Fifteen minutes into that evening, one guest turned to another and said, "You and I need to talk." In that moment, I realized I had stumbled upon something transformative. Meaningful connections are the invisible currency of our modern world. When we hit rock bottom, we're left with just two things: the integrity of our word and our relationships. While many focus on accumulating wealth or achievements, those who truly thrive understand that strategically cultivating deep relationships creates more lasting value than any other investment. Through intentional gatherings, carefully curated guest lists, and thoughtfully facilitated conversations, anyone can build a network that elevates not just their career prospects, but their entire life experience. The journey begins with understanding that authentic connection isn't about collecting business cards—it's about creating spaces where vulnerability, honesty, and genuine care can flourish.

Chapter 1: The Rock Bottom Journey: Finding Value in Connections

For years, I appeared successful on the outside. In my early twenties, I had both time and money freedom running a multi-million dollar e-commerce company. Yet something was missing. I found myself asking difficult questions: "Why am I here?" "Will I be remembered?" "How many people will show up to my funeral?" The answers troubled me deeply. Despite earning 22 times the national average income, I wasn't 22 times happier or healthier. In fact, at 23, I had developed kidney complications from stress. It became painfully clear that I had built the wrong business, attracting the wrong customers. I lived in constant anxiety, making money to buy things I didn't need, then worrying about those very things. The heaviness of success left me yearning for the lightness of being a beginner again. This realization led to self-sabotage. I knew that as long as I had my business as a Plan B, I would never pursue what truly mattered—creating work that lit me up every day. Throughout late 2011 and early 2012, I consciously decided to scale my multi-million dollar business down to zero. Unfortunately, events beyond my control accelerated this process catastrophically. When the dust settled, I found myself starting a new chapter with my soon-to-be wife and six-month-old daughter, facing a quarter-million dollars of debt with no business and no cash flow. Many entrepreneurs face similar dark moments. As Colin Collard wisely noted, "When one door closes, another one opens, but it sucks to be stuck in the hallway." Transition is brutally hard. Yet these moments of adversity often contain the seeds of transformation. For me, that transformation began in October 2012, when a friend offered a free ticket to an intimate gathering with Seth Godin in New York focused on the "connection economy"—the theory that tremendous value exists in connecting like-minded individuals. What I learned in that gathering fundamentally changed my approach to relationship building. I realized that there is no life path quite as isolating as entrepreneurship, with everyone working in their own silos. This insight became the foundation for what would ultimately rescue me from financial ruin and transform my life completely.

Chapter 2: Mastermind Dinners: Creating Your Connection Framework

After returning from Seth Godin's gathering, I decided to start hosting what I called "Mastermind Dinners." For my first dinner, I invited eight entrepreneurs who didn't know each other but shared similar challenges and complementary expertise. Truth be told, I almost canceled two hours before the event, convinced no one would see value in it and I'd be wasting everyone's time. That familiar voice of doubt was deafening. But the little voice in my head reminded me to "get comfortable with the uncomfortable" and let my discomfort guide me. Thankfully, it was too late to cancel. The dinner turned out to be a tremendous success—conversation flowed effortlessly for over four hours, and for the first time in a long time, I genuinely lost track of time. When one guest turned to another fifteen minutes into the evening and said, "You and I need to talk," I had instant clarity that connecting people was something I wanted to do for the rest of my life. Without knowing exactly where they would lead, I continued hosting these dinners. Though I had no "direct" financial benefit from organizing them, I witnessed so much value being created that I knew it would eventually return to me. These dinners added to my existing debt—I was spending between $600-$800 each time—but deep down I understood that while the bank could take my car and whatever measly assets I had left, they couldn't take my relationships. A few months after my first Mastermind Dinner, an opportunity arose to organize an event with Tim Ferriss. This felt like a chance to scale what I was already doing with my dinners. When Tim created a promotional package for his new book that included two keynote talks in exchange for purchasing 4,000 books (valued at $84,000), I immediately reached out despite having nowhere near that amount of money. I had less than two days to raise the funds. That morning, I emailed three friends. The first wanted to discuss numbers and projections, the second suggested starting a new business venture together, and the third offered to loan me the money with no questions asked. I chose the third option. When I later asked this friend why he loaned me the money when I had nothing but debt and a foggy business idea, his answer was crystal clear: he wasn't investing in the business; he was investing in me. The resulting MastermindTalks event was a huge success. We received over 4,200 applications for just 100 spots. I personally vetted every application and held phone calls with each ticket purchaser, refunding those who weren't the right fit—even though this meant returning over $43,000 when I was still deeply in debt. This level of curation paid off tremendously, as one attendee later described: "MastermindTalks felt like an enlightening two-day long dinner party in good company."

Chapter 3: The Art of Strategic Invitations and Guest Curation

The success of any Mastermind Dinner begins with who you invite. While many networking events follow a "spray and pray" approach—sending mass invitations hoping some will accept—I've always preferred a more targeted, methodical approach. I genuinely care about the synergy at the table, and this starts with careful curation of the guest list. There are two powerful concepts I use when sending targeted invites: working up the food chain and securing anchor tenants. The "food chain" approach means starting small—first inviting someone who would most likely accept (often the person with the smallest influence), then using that acceptance to approach the next person, gradually building social proof as you work your way up to bigger names. The "anchor tenant" strategy involves securing the biggest name first, which can then attract others who want to connect with that person. I unconsciously used both strategies when building MastermindTalks. Before our first event, I had little influence and virtually no brand. When the opportunity to work with Tim Ferriss appeared, I used him as an anchor to attract other speakers, especially those who wanted to connect with him. This approach helped build credibility by association—a kind of "rub-off effect" where you gain trust through osmosis. When people trust someone like James Altucher or Tim Ferriss, and they see you in their circles, that same trust transfers to you. When curating your guest list, ensure there's at least one commonality among attendees. This could be that they're all entrepreneurs, athletes, artists—it doesn't matter, but there must be a unifying area of conversation. However, avoid selecting people at extreme ends of the spectrum within that commonality. Don't put an entrepreneur with a $100 million company at a dinner with people running startups. The wants, needs, and pains of these businesses are vastly different. Also, never invite people with conflicting interests, like direct competitors. Your goal as a host is to create an environment where guests feel comfortable opening up and sharing. Having competitors at the same table will inhibit conversation flow. The size of your dinner also matters significantly. I've tested many different group sizes and found that tables of four to six people work best. Smaller groups create more intimacy, allow you to cover more ground in conversation, and increase the chances of natural flow. With six or more guests, you'll need to take a more active facilitator role, as one or two people will typically dominate the conversation, and you might need a private dining room to manage noise levels. Remember that authentic outreach is always better than cold contacting. Use commonalities as bridges—mutual friends, organizations, platforms, or events. Check Facebook or LinkedIn to see if you share connections with potential guests. As a host, your goal isn't to impress with fancy restaurants or big names, but to create an environment where meaningful connections can flourish naturally.

Chapter 4: Facilitating Meaningful Conversations and Vulnerability

The magic of Mastermind Dinners happens when conversations go beyond surface-level networking and into genuine connection. As host, your role as facilitator is crucial in creating this environment. When kicking off your dinner, I recommend explaining your relationship with everyone at the table and why you've brought them together. Then, establish some ground rules that help create psychological safety. Start by addressing confidentiality. Make it clear that what's shared at the dinner shouldn't leave the room. This reassurance helps people open up, especially entrepreneurs discussing sensitive business issues. Next, handle practicalities like ordering by the glass rather than bottles (to keep costs reasonable and prevent overindulgence), setting a clear end time (allowing people to leave gracefully when needed), and getting food orders out of the way early (so conversation isn't interrupted later). The formal introductions set the tone for the entire evening. You should go first, leading by example. The more open and vulnerable you are during your introduction, the more others will follow suit. Vulnerability is truly the key to deep connections. In typical networking settings, people engage in posturing and surface-level conversation. Your dinner offers a rare opportunity to create an environment for authentic connection. I use several introduction formats that encourage openness. One favorite is "thorns and roses," where each person shares something going well in their life or business (a rose), something with potential to be great (a bud), and something painful or challenging (a thorn). This exercise gently pushes people beyond comfortable bragging points. Other powerful icebreakers include questions like "I lose track of time when...," "What have you done in the past three months that makes you feel proud?" or "As you've gotten older, what has become more important and less important to you?" Once introductions are complete, conversation should flow naturally, but this is where your facilitation skills become essential. Stay alert to body language—notice who's making pacifying gestures, who's dominating the conversation, and who hasn't spoken much. There's no perfect formula for facilitation; your role is simply ensuring everyone shares stories and experiences while thoroughly enjoying themselves. With genuine care for those at the table, facilitation becomes intuitive. Before the night ends, take a group photo. This might feel cheesy at first—I avoided it for the longest time—but you'll regret not having this record. These photos provide social proof, give you content to post on social media (tagging guests), and make excellent additions to follow-up emails. They also serve as visual reminders of the connections made that evening. The true impact of facilitating meaningful conversations extends far beyond the dinner itself. When people experience the rare opportunity to be truly seen and heard in a supportive environment, they remember not just what was said, but how they felt in your presence. This emotional connection forms the foundation of relationships that can transform careers and lives.

Chapter 5: The Logistics of Perfect Gatherings

The success of a Mastermind Dinner often hinges on details that many hosts overlook. Choosing the right restaurant is crucial—I put tremendous thought into this decision. For local dinners, having one or two go-to restaurants simplifies logistics and allows you to build relationships with staff. When you bring consistent business to a restaurant, they'll treat you like royalty and may offer discounts or other concessions. When selecting a venue, consider your guests' needs: location convenience, menu diversity (ideally vegetarian and dietary-restriction friendly), meal cost, noise level, and table positioning. For a location I'm unfamiliar with, I often arrive over an hour early to select the perfect spot. These details matter because they create the environment where connections can flourish. Before the dinner, research your guests thoroughly. A networker researches companies; a relationship builder researches people. Learn about their business, ideal clients, family, interests, and challenges. This knowledge serves two purposes: First, it allows you to make strategic seating arrangements, placing people together who can solve each other's problems. Second, it helps you identify "uncommon commonalities" that forge deeper bonds. These uncommon commonalities are powerful connection points. Business owners represent only 3% of the general population—that's an uncommon commonality right there. Business owners with seven-figure businesses represent the top 4% of all business owners—an even stronger connection point. The deeper the uncommon commonality, the deeper the potential bond between guests. Communication before the dinner is equally important. Upon acceptance of an invitation, send a calendar invite with all specifics. The night before, send a quick reminder with pertinent details (time, restaurant address, map link) and your cell phone number. A few hours before the dinner, send personal text messages to attendees as a final check-in. These small touches show attention to detail and care. Deciding who pays for the dinner in advance prevents awkward moments when the bill arrives. I typically cover all costs when I host, not just to build reciprocity but because it feels right to me. Alternatives include having guests pay their own way (referred to as "dutch treat" in the invitation) or finding a company to sponsor the dinner. From a business ROI perspective, these dinners are incredibly valuable—for roughly $10,000, I can host almost 25 dinners, connecting with over 150 amazing people. For larger dinners, consider assigned seating based on synergy or uncommon commonalities. This eliminates the "paradox of choice" anxiety guests might feel when deciding where to sit. As Wayne Dyer said, "Go the extra mile, it's never crowded." This level of care becomes your competitive advantage as a connector. The logistics may seem overwhelming at first, but remember to start small. Your first dinner doesn't need to be perfect—it just needs to happen. With each gathering, you'll refine your approach and build confidence in your ability to create meaningful experiences for your guests.

Chapter 6: Leveraging Connections: Follow-Up Strategies

The impact of your Mastermind Dinner extends far beyond the evening itself through thoughtful follow-up. After the dinner concludes, I typically send an email introduction to all attendees, thanking them for investing their time and highlighting one or two valuable points from the conversation. I'll often include a resource list based on websites or articles mentioned during dinner. This simple gesture reinforces the connections made and provides additional value. Following a successful dinner, you can generally expect one or two people to reach out asking how they can deliver value to you. I used to deflect these offers with "Don't worry about it" or "If I think of something I'll let you know." Now, I always ask them to connect me with another interesting person. Amazing people know other amazing people, so these introductions can be invaluable when building your network or finding guests for future dinners. When facilitating introductions between dinner attendees, respect the "double opt-in" approach. This means reaching out to both parties individually to confirm mutual interest before making the introduction. One of my biggest pet peeves is receiving a vague email saying something like: "Jayson, meet David. I think you two should know each other." This puts me in an awkward position, adding another task to my already full plate while providing no context for the connection. Be the gatekeeper of your network. I'm extremely protective of my relationships and respectful of people's time. When asked for introductions, I first determine if there's a compelling reason for the connection by asking, "What is your desired outcome?" This question forces clarity and stops many casual requests. Although this behind-the-scenes work often goes unnoticed, proper vetting ensures every introduction you make has real potential for mutual benefit. For extra impact, follow up with the entire group a year later with a "Happy anniversary!" email. Include the group photo and ask how everyone is doing. This unexpected touchpoint can reignite conversations and deepen connections that might otherwise fade with time. Remember that the true value of these dinners compounds over time. Each connection made can lead to collaborative projects, new business opportunities, and friendships that transform your professional and personal life. By hosting regular dinners and following up thoughtfully, you're not just building a network—you're creating an ecosystem of mutually supportive relationships that grow more valuable with each interaction. The most successful people understand that your network truly is your net worth, not measured in financial terms but in the quality and depth of your relationships. Through consistent, intentional gatherings and thoughtful follow-up, you build social capital that generates returns far beyond what any traditional investment could offer.

Chapter 7: Beyond Dinners: Creative Connection Experiences

While dinners form the foundation of my connection strategy, the framework can be adapted to create various meaningful gatherings. Breakfasts and lunches offer more cost-effective alternatives that might work better for some schedules. However, to truly elevate your connection-building efforts, occasionally venture beyond meals to become a world-class facilitator of experiences. I recently organized an axe-throwing event for entrepreneurs that proved tremendously successful. Experiences like this take bonding to new levels because they place everyone on equal footing. When you have gatherings with highly successful individuals, sometimes certain people are placed on pedestals. Getting everyone to do something outside their comfort zone—something they're not particularly skilled at—creates a recipe for authentic bonding. Other creative gatherings might include behind-the-scenes tours of local businesses, cooking classes, or even skydiving adventures. These unconventional experiences break down barriers faster than traditional networking events because they trigger emotional responses that accelerate trust. When people share novel experiences, especially those involving mild discomfort or learning, they form stronger connections than they would through conversation alone. These shared experiences become reference points for future interactions, creating inside jokes and shared memories that cement relationships. Consider your unique skills, interests, and access when designing these experiences. Perhaps you have connections at a local theater that could provide backstage access, or you know a craft brewery owner who could host a private tasting. The more exclusive or unusual the experience, the more memorable it becomes for participants. Remember that your role as facilitator is to create an environment where connections can flourish organically, not to force networking or transactional relationships. The beauty of this approach is that it allows you to connect with people in ways that reflect your authentic self. If you're passionate about hiking, organize a trail excursion followed by a meal. If you love art, arrange a private gallery tour. These activities showcase your genuine interests while creating spaces for others to connect through shared experience. As with Mastermind Dinners, the success of these creative experiences depends on thoughtful curation of participants, clear communication, and attention to details. The extra effort required to organize these unique gatherings is repaid many times over through the depth of connections formed and the distinctiveness of your personal brand as a connector.

Summary

At the heart of every successful life lies a fundamental truth: our relationships determine our opportunities, growth, and fulfillment far more than any other factor. When we hit rock bottom, as the author did facing overwhelming debt with a new family to support, we discover that our relationships and the integrity of our word are the only true assets we possess. Through strategic gatherings—particularly the Mastermind Dinners described throughout this journey—we can transform our circumstances by connecting with others in meaningful ways. The power of these connections comes not from collecting business cards or expanding LinkedIn networks, but from creating environments where vulnerability, honesty, and genuine care flourish. Whether hosting intimate dinners, facilitating group experiences, or making thoughtful introductions, the essence remains the same: authentic connection creates value that transcends traditional metrics. By investing time in researching potential guests, creating comfortable settings for open conversation, and following up thoughtfully, anyone can build a network of relationships that provides support during challenges and amplifies opportunities during growth. Remember that your network truly is your net worth—not measured in dollars, but in the depth and quality of connections that enrich your life and the lives of those around you.

About Author

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Jayson Gaignard

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