Notes from Mastermind Dinners by Jayson Gaignard

Superconnector Jayson Gaignard shares the least sleazy networking advice I know – invite awesome, interesting people to dinner! Applying the lessons from this book has lead to loads of new relationships that I still cherish to this day. If you like connecting good people, you'll love this book.

Mastermind dinners reviewRating: 8/10
Finished: 2015
Related Books: How to Win Friends and Influence People

Buy the book on Amazon here / See all my lessons from books and smart people HERE.

The Short Summary Of “Mastermind Dinners: Build Lifelong Relationships by Connecting Experts, Influencers, and Linchpins” by Jayson Gaignard

Superconnector Jayson Gaignard shares the least sleazy networking advice I know – invite awesome, interesting people to dinner! Applying the lessons from this book has lead to loads of new relationships that I still cherish to this day. If you like connecting good people, you’ll love this book.

Lessons Learned

Money and happiness scale very differently. The heaviness of being successful left me yearning for the lightness of being a beginner again, and this is where the self-sabotage began. I knew that as long as I had a Plan B, which was a business that took care of all my wants and needs financially, I would never follow through with Plan A, which was to create a business that would light me up every day.

In the “connection economy,” there is tremendous value in being the catalyst connecting like-minded individuals.

For my first dinner I invited eight entrepreneurs who didn’t know each other (but in my opinion should) and helped facilitate connecting them. About fifteen minutes in, one of my guests turned to another and said “You and I need to talk.” When I overheard those words I had instant clarity that connecting people was something I wanted to do, in some capacity, for the rest of my life.

Although I had no “direct” financial benefit from organising the dinners, yet when I saw so much value being created I knew it was bound to come back to me someday.

Investing in my relationships was the safest investment I could make, and I believe the same is true for you.

Always invest in your network. In the end they’re all you have.

A candle loses nothing by lighting another candle.

If you hear about someone’s success and you aren’t euphoric about it – if you’re angry, hurt or there is a feeling of tightness inside of you, you’ve just guaranteed that you’ll never reach that same level of success.

If you don’t have the courage to be vulnerable at times you’ll never be able to reach a real level of depth in your relationships. If you don’t share your struggles, people won’t buy your successes.

I wish that I could buy people at what they think they’re worth, and sell them at their true worth.

I would rather have intimate relationships with the vital few than the trivial many.

Would you be friends with YOU? A common mental exercise in the dating world is to ask “would you date yourself?” If you’re single and seeking a confident, independent, physically fit partner… look in the mirror. Like attracts like.

“The best time to plant a tree is twenty years ago, the second best time is now.”

Work on building your story. There are things that I do in my life specifically to have a better story.

If I could boil my success down to one thing it’s that I have always surrounded myself with people who were one or two steps ahead of me. My model has always been that if you’re the smartest person in the room you’re in the wrong room.

I tend to prefer table sizes of four to six people. 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.

Before brainstorming who you would like to invite be clear as to “why” you are putting on these dinners in the first place, and why you want certain individuals there. There is no wrong answer, but just be clear. I will preface this by saying that a warm outreach is always better than a cold one. Simon Sinek says “people don’t buy what you do, they buy why you do it.”

“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.

Tips For Effective Outreach Via Email

Email can be a very tough channel for outreach but there are other options if you’re creative. For example, with the rise of email, there has been a huge decline in direct mail. As my good friend Brian Kurtz says, “the least cluttered mailbox is the one you grew up with.” Receiving something in the mail has become novel, and is a great way to stand out.

People will reward effort. If you send an email to someone with very little research, very little personalization, and an unclear ask, you’ve done more harm than good. Conversely, if you put a lot of effort into really personalizing your approach you’ll have a much better chance of eliciting a response.

Subject Line: It doesn’t matter how much research you’ve done or how much effort you put into your email if the five or six words you use in the subject line of your message don’t hook your prospect. Use your creative muscle and brainstorm a few options. Ask yourself, “If I received 500+ emails a day, would I bother to open this email?”

Notice how all the subject titles are open ended. An overwhelming amount of email subject lines are not open ended, so using an open ended subject line helps you cut through the noise. Also notice that they all elicit curiosity – “Adam told me to reach out to you…” Which Adam? Why did he tell you to reach out?

Depending on your subject line your receivers may think your email is spam. To avoid this, try to include something specific to them. Using their name in the subject line can also be a rather powerful hook.

The 9-Word Email: The format of this email is just as it sounds, an email in nine words. The reason the strategy is so powerful is because it’s very quick for the recipient to read, which in turn elicits a quick response. In a world where 65% of emails are read on a mobile device first, the shorter the response the prospect needs to give, the better.

Email Example: “Hey Steve! You may remember me, I’m… (blah, blah, blah). I’m holding a dinner on Tuesday with 10 people, and XYZ restaurant at 7:30pm and wanted to know if you wanted to come…” There are a solid 3–4 reasons why Steve may say no to that email. Instead, you would be better positioned to say: “Hey Steve! I’m planning to hold a dinner next week with a group of ____ (Best-selling authors, entrepreneurs, artists, etc…), interested?”

By eliciting only a tiny commitment off the bat you increase your chances of opening up dialogue, which is the core goal of reaching out in the first place. Also there’s a cognitive bias in play here. Once somebody says ‘yes’ to something small, they’re more likely to say the same thing when asked for something big in order to be congruent with their initial response.

Six months later I sent personal videos to a select group of individuals from that event that I wanted to stay in touch with, and the response was overwhelming. Here’s a quick snapshot of how powerful this form of outreach can be – and

Coming from someone who receives a couple hundred emails at a time in a single day, it’s easy for an email to get lost in the clutter. Don’t assume a lack of reply means they weren’t interested.

Whenever faced with an objection follow up with a question like “Under what circumstances would you say yes?”

Practical Tips for Organising Excellent Dinners

  • The night before the dinner I send a very quick reminder email with all the pertinent details (time, restaurant, address, and a link to a Google map) and my cell phone number should they need to let me know if they’ll be late or if something comes up.
  • Cut the cost by co-hosting your dinner with someone who values networking as much as you do.
  • A byproduct of using Eventbrite is that it guarantees the people attending are ‘invested’ in the dinner which makes them much less likely to cancel last minute.
  • A fun game is Phone Stacking. 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.
  • Sit the most interesting and outgoing person near the center of the table so everyone can easily hear them.
  • Place yourself in the center position so you can act like a “conversation cop” to “pull people into the conversation.”
  • Then, a few hours before I send a personal text message to the attendees, which serves as check-in and quick reminder. It’s often appreciated, and a bonus is that they now have your phone number readily available should they be late for any reason.
  • Open by explaining my relationship with everyone at the table, and why everyone is there. I then like to follow up with some ground rules, which may include the following: Confidentiality – Confidentiality is a big thing, especially for entrepreneurs. Setting the tone that everything shared in the room should not leave the room will really help people open up and share. People often overlook setting this agenda at the beginning because they ‘assume’ people won’t share outside of the dinner. Never assume.
  • End time – It’s important to state an end time in advance. Sometimes you’ll hit that three to four hour mark and people may need to leave but don’t want to be seen as rude. State in advance that the dinner is done by 9:30 pm (or whatever your set time is) 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.
  • DON’T FORGET: Before the night is over take a picture of the group. It sounds cheesy, and I didn’t do this myself for the longest time because it felt stupid and ego-centric, but trust me when I say you’ll regret it if you don’t. You can use these photos for social proof, to post on social media sites and to tag your guests, or as part of a follow up email.

Once you set the tone for the dinner, start with your formal introductions. You should go first because it’s an opportunity for you to lead by example. The more open and vulnerable you can be during your introduction the more people will follow that vulnerability throughout, and the deeper the connections will be. Vulnerability is the key to deep connections. Oftentimes in ‘networking’ settings it’s a game of posturing and surface level B.S. You have an opportunity to create an environment of real and raw connections (and people will never forget you for it) so don’t take this opportunity lightly. Some intros I like to use include: Top Professional or Business Achievement (brag) Top Personal Achievement (brag) A bold goal (something they are trying to accomplish in the coming year) “Thorns and roses” – This is one of my favourite openers especially when you’re dealing with business owners. You state something going well in your life or business (a rose), something that has the potential of being great (a bud), and something that is a pain (a thorn).

At our MastermindTalks events we do a lot of facilitated networking. And to do that we use some ice breaker cards, which include some of the examples below: Complete this statement: “I lose track of time when…” What have you done in the past 3 months that makes you feel proud? As you have gotten older, what has become more important and less important to you? If you could study with any expert in the world, who would you work with and what would you study? If you could invite 3 people (living or dead) to your home for dinner, who would they be and why? (For the full list of 50 questions, visit the book resource page at

Once the dinner is done it’s a pretty awesome feeling. Depending on the group (and how private they are) I will either send an email introduction to them all right after or introduce them all privately on a Facebook message. I’ll thank them for investing their time, and will often include one or two points from the dinner in the email, like “I loved John’s advice around…” or “I really resonated with…”. I also carry a small notebook during dinners for notes. If someone brings up a website name or article in the course of conversation I’ll follow up with a resource list in that group email.

After your dinner you can generally expect one or two people to reach out and ask “How can I deliver value to you?” I used to say “Don’t worry about it” or “If I think of something I’ll let you know,” but now I always ask them if they could connect me with one other really interesting person. Amazing people know other amazing people, so introductions like these can be huge when building your network or trying to find guests for future Mastermind Dinners.

Before I go through step one and get both parties to agree to the introduction 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.

A nice touch is to loop back to the group a year later and email everyone again saying “Happy anniversary!” or “It’s been one year!” as a follow up to check in on everyone and see if you can spark conversation. Be sure to include the picture you took.

This framework can be applied in various ways. The obvious ones are breakfasts and lunches. These are more cost effective to hold than dinners and can work better for some people schedule-wise. But every once in awhile, go beyond a meal meet-up. Become a world class facilitator of experience.

I recently held an axe throwing event for entrepreneurs and it was fantastic. An experience like this takes bonding to a new level because it puts everyone on a level playing field.

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