If you’d rather get this advice in a podcast, listen here. ‍

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Over the years, MMT Community taught me the value of investing in long-term relationships. I believe you can overcome any challenge and achieve anything with the right people around you. It all started with the right people around one small table. It started with a dinner party. 

Seth Godin inspired me to become a catalyst at his workshop back in 2012, where the focus was bringing like minds together to form lasting connections. I felt very isolated at the time and decided to run with Godin’s idea—truthfully, I just wanted to make some friends. I decided to host a small gathering for entrepreneurs.

First, I booked a private dining space at The Spoke Club in Toronto, small enough to encourage intimacy and avoid the noise of a big dining room. The next step? Paralyzing nerves. 

I was terrified, worried my guests would think I’d wasted their time. The negative self-talk grew stronger the closer I came to show time. Two hours before dinner, I nearly cancelled. Good thing I didn’t. To my surprise, everyone showed up. Drinks were poured. Conversation flowed. I said less than anyone, partly because I was so bloody nervous, but mostly because it was about them and not me. I witnessed the magic of bringing brilliant minds together in one room. Over years, I watched meaningful connections grow over time. Relationships and business partnerships formed at our first events endure to this day.

Now, MMT is one of the most exclusive communities for entrepreneurs in the world, and we’re having dinners—hundreds, in fact, and counting. 

Hosting dinners is the highest-yielding network growth activity that I do. When you become a catalyst and connect amazing people with other amazing people, the benefits are exponential. After 2020, the pandemic year that separated us, we understand the importance of community more than ever. Once we can gather again, we’ll be craving connections. 

Here, I’ve broken down every step to host and curate a strategic, network-building dinner that will spark long-term relationships and bring lasting value for you and your guests. One dinner can be life-changing.

It comes down to why, who, where, when and how. (And what to do about the bill). 

‍WHY

The ‘why’ for my first dinner wasn’t apparent right away. Entrepreneurship is isolating, which was a big reason for me––I wanted to surround myself with like minds. After dinner I realized that connecting other fascinating people also mattered to me. What’s your ‘why’? Do you want to reconnect with people you haven’t seen in a while? To expand your network? To strengthen it? To help others meet key contacts? 

There’s no right answer, but there is an ideal guest count. At a dinner for eight or more, you won’t have lots of time with everyone. Conversations tend to splinter off. What big dinners do is plant seeds with more people, and sometimes that’s the point.‍

Higher guest counts (8+) are better for aggressive network growth, with two benefits: 

• ‍First, building trust and rapport at scale. Relationships are like bank accounts; you never want that first interaction to take you into overdraft. I want thousands of people in my network with enough baseline rapport to ask for an introduction without overstepping. Dinner invites plant those seeds.
• Second, it allows for little moments with everyone, so you can handpick those to nurture a bit deeper. When conversations splinter off, it’s easier to get more face time with the people you gravitate to the most (it’s also easier to pull them aside and invite them for drinks afterwards).  ‍

If you want to deepen relationships, keep your guest count to six or less. As the host, you’ll be able to follow the whole conversation. Smaller tables tend to foster one singular narrative thread involving everyone. Hosts don’t have to worry that they’re missing out on another interesting topic two seats down. ‍

Part of your ‘why’ is likely about credibility. As humans, we tend to think in hierarchical social structures, so hosting a dinner will naturally lead people to hold you in higher esteem. When I started, I had close to zero social status. But being in proximity to Ryan Holiday, Tim Ferriss, Mark Ecko and the like has upped my game. ‍

So, where do you crave credibility? My friend Shep Gordon is credited with inventing the celebrity chef movement—repping clients like Nobu, Emeril Lagasse and Wolfgang Puck. When I hosted a dinner for him, some of that status rubbed off on me, and I gained loads of contacts in the restaurant industry. You might host a theme night for your industry, or throw a party in honor of someone you admire in the same field. 

After shaping the party’s ‘why’, find its people. 

WHO

A carefully curated guest list is what makes any dinner successful. Invites depend on your reason for hosting, but there is one more crucial factor. The stronger the unifying commonality among your guests, the better the bond. 

I call this the power of uncommon commonalities. Here’s what I mean:

Entrepreneurs are rare. We make up less than 10 per cent of the working age population in America. Already, when I host a group of entrepreneurs, everyone has something unique in common, more likely to get along. That said, there is a big difference between the pains and celebrations of a big company versus a start-up.  

I was once invited to an exclusive event with a very eclectic group of people. I found myself sitting next to Travis Kalanack, then CEO of Uber. A few seats away was Eric Schmidt, then executive chairman of Google. Sure, we all run companies. But Travis was running one of the fastest-growing companies in the world. Eric is known for growing Google into the behemoth it is today. Both are billionaires (I am not). We live in vastly different realities. It was difficult for us to have a meaningful conversation, let alone a long-term relationship. 

The closer the commonalities that people share, the faster they can foster deep and meaningful relationships. You can move through those first stages of intimacy a little quicker knowing something is shared. Maybe you’re both parents or artists, or maybe you both served in the military. The deeper the uncommon commonality, the deeper the bond. ‍

The key to curation is hitting that sweet spot, where your guests have enough in common to hit it off, but not so much that they’re direct competitors.‍

Two people in the same industry with companies of similar size might be weary of each other. You want to create an environment where your guests can open up and share—conversation won’t flow if they’re worried about revealing proprietary secrets. 

Once you land on a guest list, the rest is a piece of cake. Next is figuring out where to eat it. 

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WHERE

The more people you invite, the harder it is to find the perfect venue. 

Still, the four most important factors for picking a venue are the same:

1. Accessibility

Think about where the bulk of your guests are located before picking a venue in the middle of nowhere, or an urban center where parking is impossible. I once asked my assistant to pick a restaurant in San Diego. I didn’t realize until I was en route that it was taking the last exit before the border to Mexico. Be more conscious than I was. Consider major highways, parking, public transit, and how busy the area will be at that time of day. Your job as host is to design an incredible experience, starting with the commute.‍

2. Value‍

I’m always looking at restaurants with great reviews, an average of 3.5 stars minimum across the major aggregate sites. I avoid pretentious places that are over-hyped or overpriced. Wherever you choose, watch out for minimums. At one place I considered, there was a $110 per-person charge. Turns out, they’d accounted for four drinks each. I told them if my guests were consuming an average of four drinks each, I’d have bigger liability issues. Sometimes, minimums are negotiable.

3. Dietary restrictions

This can be fun to navigate. I have some friends who are vegan, paleo, halal, you name it. I always pick restaurants with wide menu selections. In general, one of the most flexible cuisines to work with is Mexican. Most dishes contain lots of interchangeable ingredients, making substitutions and omissions easier.   ‍

4. Intimacy

‍A table of four to six can be hosted almost anywhere, ideally at a booth or table tucked away in a corner. With eight or more guests, consider a private dining room to better control the setting and potential distractions. Private dining rooms are intimate, but can be harder to book, so do it well in advance. They also tend to be more expensive and sometimes require prix fixe menus. 

Ask in advance about ordering a la carte instead of the prix fixe option. I work with my wife to plan many events, and she once had a great idea to order a bunch of food to share, family style. This creates the illusion of a feast with food service staggered throughout the evening, and it controls costs. 

Next, pick a date. Naturally, this depends on availability at your venue, but there’s lots more to consider before booking. ‍

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WHEN‍

To pick a date, look at your guest list. For entrepreneurs who are parents, weekdays tend to work best. In my world, weekends are reserved for my family. If your group is made up of young, single professionals, Friday or even Saturday night might work.

Some prefer to steer clear of after-hours conflicts altogether and host a breakfast or lunch. I prefer dinners because there is no time constraint. You can allow for two hours but still linger at the bar afterwards. So, while breakfast and lunch are often easier for your guests to commit to, they probably can’t stay as long given meetings and workday commitments.  ‍

One of the best times to host is in tandem with a conference or an event where everyone attending already has something in common. ‍

And there are other benefits:

• A list of attendees or at least speakers is released in advance, making it easier to find contact information for people who are available and in town. 
• Conferences catch people outside of their regular routines. They don’t have day-to-day responsibilities like Wednesday yoga or after-school pick-up. 
• Drastically changing your environment, it’s been said, can radically change behavior. Disrupting schedules can make people more open. Maybe you’ll be more likely to hear ‘yes’ when ‘no’ would have been the default

Once you decide on when, schedule it. Your likelihood to follow through goes up when you put it in your calendar right away. 

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HOW‍

There’s so much to cover here, from invitations to seating plans. I carefully curate all of my seating arrangements, choosing placements based on shared interests––those uncommon commonalities––to make everyone more comfortable.

I’ll start with a story about one of my early dinners:‍

At the time, I’d built an incredible network of peers across North America, even globally, but I wasn’t plugged into my own city. I had a young family establishing roots in our town, and I wanted to support local business and get to know the people who shaped the community. That became my ‘why.’  ‍

I hosted a dinner on a Wednesday in July. Seasonally, that’s not a bad time, with no major holidays and most people slowing down schedules for the summer. The venue was a distillery turned event space, which I chose because it was outside the city and had just opened. None of my guests had ever been, meaning everyone would share a new experience together. It also ensured intimacy because we were the only ones on the property. The guests all had local roots, doing what I considered to be fascinating things. Industries varied, but they were all people I was drawn to.  ‍

Here’s a behind-the-scenes look at that dinner.

Watch this video to go behind the scenes with me at a recent dinner in Toronto.

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Preshow

First, I scheduled it. Putting it in my calendar made it real. Then I booked the restaurant. In this case, a venue and a catering company—more than I usually do, but I really wanted to impress these local entrepreneurs.  

I started a guest list from scratch since I knew almost no one locally. I had to pull from my fringe network, meaning posting on social media and emailing existing contacts. I was able to do this because of a principle I follow: always be collecting.

When I host an event, I generally ask guests if there is someone who should be on my consideration list. This does a few things: it creates a short list for my next event and options for alternate invites in the case of last-minute cancellations. After hosting events for years, I’ve built up quite the fringe network. Now, when I post something like: Hey. I’m hosting a get together for artists/entrepreneurs/local business owners (or whomever), who should I invite? I get 40-70 names in response. 

‍At the time, I didn’t have as much social capital. I asked myself: If I were a notable entrepreneur living in this city, where would I be? I looked at local business associations, newspaper archives, regional business magazines and local award recipients, as well as runners up. 

At this stage, I considered partnering with connectors. These are the people who show up to everything, often publicists, lawyers, journalists and others who benefit from wide networks. If a full-on partnership (or co-hosting) seems too much for you, suggest that your influencers invite some of their own guests. (Be clear about the kind of guest you’re looking for). ‍

Once you have a list, there are two approaches for invites. The first is to send email blasts and pray that enough interesting people reply. The second is more targeted. It’s also the one I prefer because I genuinely care about the synergy at the table. ‍

I want to hand-select every guest. Going this route, you could either focus on anchor tenants or work your way up the food chain. I stole both concepts from Ryan Holiday’s Trust Me, I’m Lying, which is a book about PR tactics that I use to plan dinners. 

Working up the food chain means starting small. If you’re in PR, send your story or an anonymous tip to a blogger. They get a story; you get an outlet. Then, send that story to a bigger outlet, and so on and so on. Suddenly, your story is news. If you’re party planning, send your first invite to the person with the smallest contact list, then build up social proof as you invite bigger players.

By social proof, I don’t mean name dropping. This can backfire. I always assume the person will follow up to ensure the big name is attending. I only drop names of mutual friends. If I’m going to drop anything else, I’ll use achievements, mentioning that one guest raised $300 million recently, or is a multiple New York Times bestselling author. 

Another more tactical approach is the anchor tenet, catching the biggest fish first. If you land Nordstrom, for instance, other retailers will follow. Granted, this takes more work, but all your energy is focused on one major goal. 

I used multiple strategies to build MMT. I got Tim Ferriss to speak at my first big event through a promotional opportunity. Once I landed Tim, I knew I could land other speakers. I could also reconnect him with his friends or people he’d been meaning to reconnect with. It was tough to land Tim, but the rest of the guest list grew naturally.‍

Now for the invitations. The key to a compelling invite is a strong ‘why.’ Simon Sinek made this idea famous: “People don’t buy what you do, they buy why you do it.” My friend Simon Bowen made a slight change. He says: “People don’t care about what you do unless they are the reason why you are doing it.”

‍For my gathering of local leaders, the invite described an event that wasn’t about me. I said I wanted to connect the fragmented entrepreneurial community in our town. I was just the catalyst. I also mentioned to each person why I invited them specifically—I’d been a customer, or I loved their work. And I explained how the dinner would benefit them. ‍

Keep track of your invitations. I always keep Google Docs handy, listing everyone’s reply status and when to follow up. ‍

Once guests accepted, I sent intake forms. This handles logistics like dietary restrictions and helps with assigned seating as guests list interests, hobbies and accomplishments. And of course, a space to nominate other guests to future dinners (always be collecting). ‍

The day before, I sent out an email reminder to build anticipation and ensure no last-minute scheduling conflicts. I also sent out more personal details I learned about my guests from their forms. ‍

On the day of the dinner, I texted every guest individually from my personal number, both to confirm again and to make it easier for them to communicate with me directly.

An hour before the dinner, I went to the restaurant. I like to meet the servers, learn the layout, and pick my table (if you get there early enough, you can usually do this and pick a quieter spot). I also prepared my opening remarks and assigned seats based on what I’d learned from the intake forms. ‍

As people arrived, I greeted as many people as I could at the entrance. Walking into a new environment can make people anxious, and this helps them feel welcome. 

‍Once seated with drinks, I made opening remarks. I mentioned the dinner duration, highlighted menu items, then reminded everyone about the why before introducing people one by one. ‍

I used to ask guests to introduce themselves—not anymore. Many accomplished people are not good at this. They get nervous and ramble or they stay super humble and undersell themselves. So I sing praises, giving context as to why they are invited and how I know them: Jim was my first-ever mentor. I came across Angela in a Forbes Magazine article. Because the group is curated, there’s already a feeling of safety. I reiterate my no solicitation and strict confidentiality policies. This is key to creating an environment where guests can be vulnerable. If you want to catalyze lasting connections, vulnerability is key. 

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Showtime

I am notorious for not eating at my dinners. I’m busy ensuring guest meals are right, drinks are ordered, and conversation is flowing. I hover around like a pit boss at a casino. Much like a pit boss, I look at body language. Is one person dominating the conversation? Is another person awkward or shy? I try to intervene casually. ‍

Then, between entrees and desserts, I moved to closing. I thanked everyone. Then I announced the Champagne Moment question. “If we were to meet a year from today with a bottle of champagne, what are we celebrating?” 

Answers give everyone in the room a snapshot of one another’s goals, even for people they hadn’t already chatted with. And it offered a great topic for follow-ups—even that same night. 

Afterwards, guests wound up at the bar to discuss how everyone could help with each other’s champagne moments. 

Of course, you could pick another question. Entrepreneurs love a good ice breaker. I have a list of ice breaker questions here.‍

If possible and the setting permits, get a group photo. This is a nice memento. More than that, amazing people tend to get more amazing over time. I think of Earnest Solvay, a Belgian chemist, who held a conference in Brussels in 1911, now considered a turning point in modern physics and chemistry. He took a photo. Of the 29 people in it, 17 went on to win Nobel Prizes. The photo is now part of history.  

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After show

I sent thank-you notes to each guest. I mentioned moments from the dinner, including each one’s champagne moment answers. It’s a good practice to include the group photo if you took one, and with everyone’s permission, share email contacts. You can also put everyone in a Facebook group chat, making it easier to send friend requests. 

If you want to nurture deeper relationships, pick a handful of people to invite to another event in the future.

Keep following news alerts and updates on your guests. When someone achieves their champagne moment, you can follow up in a group email to celebrate. If you really want to impress them, send a bottle of champagne. ‍

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WHO PAYS?‍

There is the small matter of the bill. I always pay, but that doesn’t mean you have to. Decide in advance to avoid the awkwardness of your server asking about separate checks.

To cut costs, you might co-host a dinner and split it or have guests pay.‍

If you prefer your guests to pay, mention it in the invite by calling it a “Dutch treat.” Set up Paypal or Eventbrite if you’re monetizing your dinners. Asking for payment also ensures people are invested, less likely to cancel. ‍

Or get a sponsor. In the case of MMT, one could say my company is a sponsor. For roughly $10,000, I can host 20-25 dinners and reconnect with 120 people or so. I wouldn’t think twice about spending that budget on marketing, with no guarantee of returns. For me, dinners are a better option for that budget line. ‍

If you know your guests well, credit card roulette is a fun option. Ask your server to put everyone’s credit cards into a bowl, removing them one by one and reading the names aloud. The last card removed belongs to the person who pays the bill. This can be a riot. Make sure everyone agrees to this in advance and give people the option to opt out if they prefer to pay their own bill.  ‍

Another game is phone stacking, putting cell phones in the middle of the table to help everyone be more focused and present. The first person to cave and pick up their phone pays the whole tab.

Whew! You made it! And that’s just my advice for a dinner party. You could host a cooking class, axe-throwing or an escape room using these same principles. Activities tend to put people on level playing fields, with everyone out of their element (not many people throw axes or escape from rooms based on clues in their spare time). Still, dinners will always be closest to my heart.

Why not host your own? Or leave the work to us and sign up for MMT today.‍

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Jayson Gaignard is founder and head curator at MMT. Named a Top Networker to Watch by Forbes.com for his work building community, Jayson has planned hundreds of events and screened thousands of potential dinner guests. Here, he shares everything you need to know in a step-by-step guide to hosting a dinner party, adapted from his book, MasterMind Dinners: Build Lifelong Relationships by Connecting Experts, Influencers, and Linchpins.