Mastermind Dinners Blab - Ovi Negrean and Jayson Gaignard

Key takeaways from our interview with Jayson Gaignard,  the chief mastermind of Mastermind Dinners.

“If you're the smartest person in the room you're in the wrong room.” @JaysonGaignard Click To Tweet

It was a great first Q&A and Jayson shared a lot of nuggets of wisdom about how you can connect with top people in your field, how to grow your network and, in turn, grow your net worth. Because ‘your network is your net worth‘.

And here’s my review, for nugget.

Mastermind Dinners is a no-nonsense, no BS, tried-and-tested, experience-based book. And I loved it. Jayson Gaignard wrote it in an honest, friendly tone and gave away the blueprint for how he used this exact method to go from a quarter-million US dollar debt to a successful business.

So get ready for many knowledge nuggets (visual quotes from books).

When you hit rock bottom in life, you’ll be left with two things: the integrity of your word, and your relationships. Never tarnish your word, and always invest in your relationships.

Gaignard did hit rock bottom at one point. After a successful event ticketing business but a bad partnership, he was left with a large amount of debt and didn’t know how to proceed. This was when he decided to pull a Hail Mary and invest tens of thousands of dollars into the top package of Tim Ferriss’s book launch bundle.

For about $40,000 he got a few thousand books and the promise of 2 speaking gigs from Ferriss himself. To the untrained eye, this might seem a risky investment. But Gaignard knew that even if he could not monetize this himself, he could re-sell both those 2 speaking engagements and the books, so he would not lose money.

Entrepreneurship is about thinking about massively positive outcomes, but also planning for plan B and C and preparing for any downsides.

Gaignard understood early on that even if he goes bankrupt, nobody can take away his relationships. So he decided to invest in that: meaningful relationships with people he can learn from.


Mastermind Dinners gives you a clear blueprint of how you can run mastermind dinners yourself.

So what are mastermind dinners? They are, well, dinners, of usually around 6 people who share an uncommon commonality; something that not everybody has, something that is quite specific, but they all possess.

Sure, you can also have such dinners with random people, but uncommon commonalities unite people, give them common grounds and understandings, and support everybody in helping each other as much as possible.

The bedrock of building genuine relationships is trust. Trust comes from honesty and vulnerability. “Honesty, vulnerability and integrity are expensive gifts, don’t expect them from cheap people.


A scarcity mindset is zero-sum.

So make sure you only invite people with an abundance mentality. People that are willing to share and help others.

Here are a few things to keep in mind when planning your dinner:

  • You must be sure there is at least one commonality among your guests.
  • Make sure you don’t select people at both extremes of the unifying commonality.
  • You don’t want to invite anyone with a conflicting interest.
  • Ideally, keep the number of people low, six ideally.

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.

Even though Gaignard usually hosts these dinners for entrepreneurs or best-selling authors, they work for anyone. How should you go about selecting your guests?

Let’s say you want to host a dinner for a group of speakers, and you have a list of ten prospects. Start small by inviting the person who would most likely give you a ‘yes’ (oftentimes this is the person who is least in ‘demand’ and has the smallest influence). Once you get that person on board, move on to the second most likely person to give you a ‘yes.’ … You work yourself up the chain, building social proof along the way. … The second approach to use when sending targeted invites is getting the big fish, also known as the anchor tenant, right away.

When making these decisions, be authentic, because: “Make no mistake, authenticity builds credibility”. Credibility can be established with credentials, or by being transparent that you have no credentials.

When you start reaching out to your guests, do an in-depth research to find a unique angle to reach out to each individual. “Don’t forget to ask yourself one of the most important questions of all: ‘what is in it for them?’”

You may be reaching out for business purposes, but you may be able to connect based on a common interest outside of business.

In today’s digital age, sending a gift or a physical card in the post will make you stand out. No matter what contact medium you choose, the success of the outreach is often directly proportional to the amount of effort you put into it. “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.


Be prepared for rejections as well, but “whenever faced with an objection follow up with a question like ‘Under what circumstances would you say yes?’”, because “oftentimes the difference between a ‘yes’ and a ‘no’ is a ridiculously small concession.

Read the full book for more specific and actionable advice about reaching out; emails that get opened and get a positive response; picking a venue; how to best order food and wine; how and who should pay; credit card roulette; timing; sitting arrangements; staying in touch once the dinner is done; and much more.

One thing I’d like to leave you with is one of Gaignard’s favorite exercises, the one he likes to start the dinners with. It’s called thorns and roses. “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). This exercise forces people to open up a little more than a brag so some pushback is to be expected sometimes (as far as people not going as deep as they could). As long as you go first people often open up pretty easily afterward.

And remember:

It’s better to take imperfect action than no action at all.”

See it’s main nuggets: