Mastermind Dinners by Jayson Gaignard: Summary & Review

Mastermind Dinners is a book on how to host mastermind dinners that expand your personal network and produce career opportunities.

Exec Summary

  • Try to get high-value people to attend: if you can, you can leverage that into getting more high-value attendees and a higher attendance rate overall.
  • Do as much research as possible before the event: to organize the event well and prepare for the conversations you’ll have.
  • Send post-dinner follow-ups: to continue the relationships.


About the Author: Jayson Gaignard is a Canadian entrepreneur, networking specialist, and author who founded MastermindTalks, an invitation-only conference for entrepreneurs.


Note: This section had no official title, he transitions straight from the Preface to the subchapters. So, I’ve grouped all of the subchapters before the first official chapter (twelve in total) as the Introduction.

The book opens up with the story of how Gaignard was earning great money (22 times the national average income, to be exact), but unhappy.

Then, he went to an intimate gathering with Seth Godin where the theme was the “connection economy” (the theory that there is tremendous value in being the catalyst connecting like-minded individuals). And at that event, he gave thought to the idea of how isolating entrepreneurship can be and decided to start Mastermind Dinners.

When he hosted his first dinner (with eight invitees that didn’t know each other before then), Gaignard says that the conversation didn’t skip a beat for four hours and for the first time in a long time, he genuinely lost track of time. And he knew then that connecting people was something he wanted to do for the rest of his life.

At the time, each dinner was costing him around $600-$800 and putting him further into debt, but he believed no matter what assets and belongings got taken or repossessed, the bank couldn’t take his relationships.

He believed investing in relationships is the safest investment he could make and that the same is true for everyone else.

A few more ideas here:

  • Conduct quality control for your events: he later hosted his first MastermindTalks events and accepted many applications from entrepreneurs. But he rejected any entrepreneur he wouldn’t want to have dinner with (regardless of their business size or revenue).
  • Adopt an abundance mindset: and use it to encourage collaborative frames. Choose to believe that there’s enough in the world for everyone that you can give without losing. After all, a candle loses nothing by lighting another candle.
  • Be a talent scout: wanting to connect with big names often comes from ego. For a better return, connect with people who have great potential (a high social ROI), invest in them, and watch their success explode.
  • If you’re a creator, adopt a philosophy that aligns with the 1,000 True Fans Theory: which is that anyone who produces content or works of art only needs 1,000 true fans to make a living. Quality over quantity.

Chapter 1: Mastermind Dinners

Mastermind Dinners are the highest value “connecting” activity that Gaignard does and it comes in two forms: local dinners and location dinners.

Both are generally focused around these three areas:

  • Reconnecting with old ties (catching up and keeping relationships healthy)
  • Introducing people who can benefit from knowing each other
  • Connecting with people who you’ve been meaning to connect with for some time (if you invite eight people and all eight show, you’re killing eight birds with one stone)

Gaignard tries to host these gatherings as often as possible, but since many of these dinners can have mix of people from all three categories above, he has to be very mindful of the synergy within the group.

Focusing more on the two types of dinners now:

  • Local dinners: these are dinners hosted in your local area. They enable you to build roots locally and give you the benefit of having a go-to restaurant that you can regularly make good use of. The downside is that these dinners can make it harder for schedules to align.
  • Location dinners: nonlocal dinners. They’re great for reconnecting with old ties when traveling or connecting people with a common interest.

For location dinners, Gaignard recommends holding these when you go to another city for an event because:

  • People going to an event share some form of common interest by default: and that common ground will benefit the group’s synergy
  • Many events offer a list of attendees or some sort of access to an online community before the event: so it’s easy to create a list of people to reach out to
  • It catches people outside of their normal routine: hosting a dinner for a group of people who are traveling is an easy way to stay clear of their normal day-to-day routines, commitments, and responsibilities they may have

Planning the Perfect Dinner

Keep these in mind:

  • Commonalities: make sure there is at least one among the guests, there has to be at least one unifying area of conversation. But, avoid extremes (such as having the owner of a million-dollar company at the dinner with only owners of startups) and conflicts of interest (such as inviting direct competitors together).
  • Group size: the smaller the group size, the more intimate the dinner feels, the more ground you can cover, and there’s an all-around better chance there will be a flow to the conversation. Gaignard prefers table sizes of four to six people.

Finding Dinner Guests

Things to keep in mind:

  • Social proof and authority-endorsement improves your response rate: work to build it by working to getting big names to come to your gatherings, but start small with “not so big” names.
  • Be clear on why you’re putting on the dinners and why you want certain individuals there: there is no wrong answer, just be clear.
  • Go for warm reach-outs whenever possible: reaching out cold with no influence or social proof to high-status people can be time-wasting. Instead, use a mutual friend
  • When sending invitations, go for a targeted, personalized approach: a “spray and pray” email blast is an approach that gives less attention to the synergy at the table
  • When sending invitations, go for a “working up the food chain” approach: if it’s a list of ten prospects, start small by inviting the person who would most likely give you a “yes” (oftentimes this is the person least “in demand” and with the least influence). Then, once you get them on board, move to the second most likely person to give you a “yes”, mentioning that the prior person will be attending as well. Continue this approach up the ladder to the prospect with the highest influence, building social proof and authority endorsements along the way.
  • Or, go for an “anchor tenant” approach: focus on getting one big high-status person to come to your event, then mention their name when inviting other prospects on the list to come.

Chapter 2: Authentic Marketing 101

Here, Gaignard reiterates the Simon Sinek quote, “People don’t buy what you do, they buy why you do it.” (See Start with WHY.)

Be honest, raw, and authentic. And focus on selling the “why”.

Creative Outreach to High Profile People

First, double-check that you need to reach out to that high-profile person at all.

Gaignard: “…ask yourself, if I am unable to connect with this person, are there alternative people who could help me reach the same desired outcome? By widening your options you will realize there may be several people who you can contact instead who will help you get to exactly where you want to go, with a lot less effort.”

Then, follow this process:

  1. Do your research: “by doing in-depth research you may be able to find a unique angle to use to reach out to that person. You may be reaching out for business purposes, but you may [also] be able to connect based on a common interest outside of business.”
  2. Check if you have any friends in common: “Check platforms like Facebook and Linkedin to see if you have any mutual connections. If for some reason you don’t find any common connections, broadcast out to your network.”
  3. Choose the best medium for outreach: pick the least “noisy” one you can find. For example, their email might be monitored by gatekeepers (personal assistants) so it may make more sense to try reaching out via Twitter.
  4. Reach out strategically: much of the appeal of your gathering is in how you present it.

There are two main ways Giagnard does his reachouts: the “9-word email” and video/audio email.

The 9-word email goes like this:

Email: “Hey Steve! I’m planning to hold a dinner next week with a group of ____ (Best-selling authors, entrepreneurs, artists, etc…), interested?”

That’s the whole body of the email (it’s one sentence that’s around nine words in length).

If they say “yes” that’s a small win and you can respond with email #2, which would include a date and a time. 

The video/audio approach is simply a process of sending a short video or audio message in an email which helps you stand out.

From here, if there’s no response follow up. And if they reject/object, ask something like, “Under what circumstances would you say ‘yes’?”

Chapter 3: The Magic Is In the Details

Choosing the Perfect Restaurant

“…once you have one or two go-to restaurants it’s a huge weight off your shoulders logistically. Also if you bring a consistent stream of business to a restaurant, they will treat you like gold and there are other ways you can leverage the relationship (including some kind of discount, financial kickback, or concessions).”

Things to consider here:

  • Location
  • Menu diversity (try to find restaurants that are vegetarian and Paleo-friendly)
  • Meal cost
  • Noise level
  • Availability of private rooms (and private room minimums)
  • Table location

Chapter 4: Do Your Research (Again)

“A networker does research on companies; a relationship builder does research on people.”

There are two main schools of thought when it comes to doing research on people:

  1. Only do the bare minimum (and nothing more): some benefits are that it forces you to be present and it forces you to ask very poignant and interesting questions. (If you do a ton of research on an individual it may feel like the conversation has already been “had,” which can make things very stale. It’s the difference between connecting with the person vs the persona.)
  2. Aim to know as much about the group as possible in advance (the more you know the better): some benefits here are that you don’t leave the serendipity of great conversations to chance, you’re able to discover and utilize uncommon commonalities to forge deeper connections. And by discovering everyone’s issues, you can arrange the seating so everyone is seated next to someone who can potentially solve their challenges.

Pre-Dinner Communication

First, Gaignard generally tends not to share the guest list with the attendees because it can lead to false perceptions and expectations. (Guests may research the other guests beforehand and prejudge the quality of the dinner or attendees based on whatever they find online.)

So, the night before the dinner he’ll send a very quick reminder email that only contains the most pertinent details (time, restaurant, address, and a link to a Google map) and his cell phone number should they need to let him know if they’ll be late or if something comes up.

Who Picks Up the Tab?

You have a few different options:

  • As the host, you pay for everyone’s dinner: you can also get a co-host who values networking as much as you do to split the total bill with them.
  • Guests pay for their own meals: you can mention it in the original email invitation or set up a way for people to pay in advance (and with that second option, people are less likely to cancel last-minute since they’re financially invested)
  • Find a sponsor: find a company that’s willing to sponsor your dinners.

Seating Arrangements

For larger groups, you can pair people up based on synergy or uncommon commonalities.

Almost everyone experiences the paradox of choice trying to “choose the right spot.” This alleviates that worry for them.

Chapter 5: Your Mastermind Dinner

Last steps:

  • Call the restaurant to confirm the reservation
  • Send a personal text message to the attendees a few hours beforehand: which serves as a check-in and a quick reminder
  • Arrive at the restaurant anywhere between 25 to 60 minutes in advance: to ensure you get the right table (if you haven’t been able to select the table in advance) and greet anyone who arrives early

Kicking Off the Dinner Right

The initial introductions can be as casual or as structured as you’d like.

One way to go about it is to start by explaining your relationship with everyone at the table and why everyone is there. Then, follow up with some ground rules.

Here are some sample rules:

  • Confidentiality: everything shared in the room should not leave the room.
  • Order wine by the glass only: “…if bottles of wine are on the table people will drink it. If they need to order by the glass, they won’t order as much. This helps both to keep the cost down and lessen the possibility of someone having a little too much to drink (which can happen).”
  • No cell phones: optional, but helpful for encouraging more and better conversations
  • Order early: ask the group to order within a few minutes of “housekeeping” and introductions because it’s not uncommon that an hour after the dinner has started, people are in such deep conversation that they have yet to look at the menu.
  • End time: state in advance the time the dinner is done but that everyone is more than welcome to stay longer. (This allows those who need to leave early to do so gracefully while others can stick around.)

Then, once you’ve set the tone for the dinner, start with your formal introductions.


Send a thank you email and start introducing everyone to each other.


  • Work on yourself first, then focus on the networking tools and strategies out there

Gaignard: “Ryan Holiday spoke at our first MastermindTalks event, and the central idea of his talk was that if your product is crap, good marketing will just help people realize your product is crap quicker than they would have otherwise. The same idea applies to relationship building; it doesn’t matter what tools you use or how good your strategies are…if you’re inauthentic, selfish, or egotistical, good strategies will just allow others to discover who you really are more quickly.”

  • On an extreme growth mindset negating jealousy or envy

Gaignard: “I have some amazing friends (who are also incredibly successful). The only reason that I do is because when they succeed, I cheer for them. I’m thrilled for them. I don’t say to myself, ‘Why do they have that, and I don’t?’ I know that I have different plans and energies and I’m not committed to doing the same things. If I was committed to the same things, I know I could probably accomplish similar results.”

  • More wise points from the book

“When you hit rock bottom, you’ll be left with two things: the integrity of your word and your relationships.”

“Honesty, vulnerability, and integrity are expensive gifts, don’t expect them from cheap people.”

“At the end of the day, it’s not how many friends you can count, it’s how many friends you can count on.”

“Get comfortable with the uncomfortable because unfaced fears become your limits.”

“Even leaders need a tribe.”


  • Would you be friends with you?

Gaignard: “Maybe it’s time you did a personal balance sheet. Entrepreneurs list their assets and liabilities for their business on a regular basis, so why not do it for yourself on a personal level? List your strengths, weaknesses, what makes you unique, and the ways you can provide value to others.”

I’d recommend starting with these two articles to see how many traits you can check off as well as what to look for in others:

  • On the value of social proof and working to achieve it

Gaignard: “At a recent large dinner I hosted in NYC I sent out thirty-four invitations. Out of that group, thirty-two people said yes and showed up to that dinner with not a single cancellation. That’s a 94% acceptance rate on a dinner that consisted of multiple New York Times bestselling authors, online influencers, and well-known industry leaders. I say this because two years ago this definitely wasn’t the response I was getting. I was lucky to get a 5% response rate to my invites and had to deal with several last-minute cancellations on more than one occasion. What changed? Social proof. And the only way to get social proof is by putting in the work. Sean Stephenson says that ‘if you want to experience success, be prepared to face dead-ends and false alarms. They’re meant to shake off the wannabes.’ So start small.”

  • In the social exchange, your reach-out is costing them time, so respect it

Gaignard: “You may not be reaching out to them for money, but you’re reaching out for an even more precious commodity – their time. We live in a world where there are two currencies: money and time. That’s why they call it ‘paying’ attention…Put yourself in your prospect’s shoes: where are they when they receive your email? What other distractions or demands may be happening at that time?”

Real-Life Tips

  • Hold a dinner for speakers

Speakers want to be connected to like-minded individuals and event organizers rarely do anything for their speakers while in town. So, it’s very easy to put something together and be a hero.

  • Test open-ended subject lines

Since most subject lines are closed-ended, an open-ended one (that includes an element of personalization) can help your email stand out.

For example, “John, I’m doing a dinner with a group of entrepreneurs…”

  • Recognize when to switch gears in your journey

If you build high-value connections well, it won’t make sense to expand your network forever. 

At some point, you’ll get more value from focusing your time and energy on deepening your current relationships further than finding new ones. 

  • Utilize facilitated networking when necessary

For example, using ice breaker cards, being conscious of people’s body language at the table, keeping an eye on who’s dominating the conversation and who’s not talking enough, and so on. 

Don’t leave it to the group to figure out on its own how to thoroughly enjoy themselves. If it’s a group that needs it, help facilitate a great time.

  • Take a picture of the group at the dinner

The uses for such pictures go further than only building memories, it can help build your network faster too (such as by using it in a follow-up email, posting on social media as social proof, and so on).

  • Ask permission before making an introduction

An unexpected introduction can put high-value people in a tough spot as it forces them to add yet another thing to their to-do list they didn’t plan for. And many busy people often don’t have time to reply to the email itself, much less set up a call to meet someone new that they’re not even sure they want to meet.


  • The connection formula seemed inaccurate

Gaignard makes the case that you can’t have a connection without honesty (to communicate effectively and hold the relationship together), vulnerability (to reach a level of depth in your relationships), and integrity (to build and maintain a good reputation).

But, truthfully, you can’t have a connection without power awareness. Without it, you’re at risk of being too honest (and as a result, oversharing), too vulnerable (and coming across as weak), and your goodness of character/integrity coming across as nice guy syndrome.

So, a better mix might be to say you can’t have a connection without knowledge of power dynamics, emotional intelligence (which includes relationship management anyway), and honesty to your own value system. (See “10 Traits of High-Value Men”.)

  • Some punctuation mistakes

And that brought down the book’s credibility for me a bit, but only a bit.

  • Mixed information

Gaignard says that at the dinner, once you’ve set the tone, you should start with formal introductions. And go first so you can lead by example, being open and vulnerable so others will be open and vulnerable in their introductions that follow.

But, two of the three introductions he uses and recommends are centered around social climbing.

From the book:

  • Top Professional or Business Achievement (brag) 
  • Top Personal Achievement (brag)

That can set an example (and maybe even a competition, depending on their attitudes) where people feel the need to “prove their value” in their introductions as well.

  • A couple power unaware moments

For example, Gaignard at one point says:

Gaignard: “You need to be the gatekeeper of your network. I am VERY protective of my relationships and very respectful of people’s time. Because of my associations I am asked on a daily basis for introductions…I make sure there’s a strong and compelling reason as to why I’m doing the introduction in the first place. I’ve learned to ask ‘What is your desired outcome with the connection?’ This question stops half of those who reach out to me dead in their tracks and forces them to get really clear about what they want or need. You wouldn’t believe how many people request a connection to somebody else with virtually no clarity as to what they want out of it.”

When I read this, I thought to myself, “Were they stopped dead in their tracks because they had no clarity or because of the way you phrased the question?”

That phrasing begins to frame the receiver as if they’re only looking to get something out of the person. It makes them look like a taker.

So, better might’ve been another type of phrasing.


  • Gets the WIIFT Rule

A quote straight from Gaignard himself:

Gaignard: “Don’t forget to ask yourself one of the most important questions of all – ‘what is in it for them?’ It is baffling how often this question is overlooked. If you’re reaching out to someone cold, there must be some kind of clear benefit for them.”

  • Fun ideas for making dinners and gatherings more memorable

For example, with a group that you know well, you can play Credit Card Roulette:

Gaignard: “Everyone at the table puts their credit card in a pile and hands them to the waiter who then puts them into a napkin or glass. The waiter pulls out the cards one by one, and the last card removed is stuck taking care of the bill…The key is telling your guests in advance and allowing people who want to pay for their own bill to opt out.”

Or, Phone Stacking:

Gaignard: “When at a dinner, people are often on their phones – so grab them and stack them face down in the center of the table. The first to pick up their phone pays the bill for all.”


This book delivered as far as giving a solid overview of how to host mastermind dinners. 

However, it was too much of an overview and, therefore, felt like it was lacking content. 

I wish there were more details such as how to hold conversations at events that make attendees eager to get to know you better, willing to become an ally in your network, and happy to come back to your future dinners. 

With the book being so short, for me, this book also fell short of the extra step that could’ve taken it to a higher rating. 

Get the book here.

Or, check out the best books on social skills.

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