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Building Meaningful Connections: The Journey Of The Greatest Connector with Jayson Gaignard | Ep. 163

BDD 163 | Building Connections


Never did anyone go wrong with building relationships and meaningful connections. Jayson Gaignard, known as The Greatest Connector, hosts the most exclusive events called the Mastermind Talks (MMT) where he connects and brings brilliant minds together. Jayson shares his amazing journey to success – from a soaring business to being buried in debt. Find out how Jayson was able to rise up again to claim a newfound victory by building connections.

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Building Meaningful Connections: The Journey Of The Greatest Connector with Jayson Gaignard

BDD 163 | Building Connections
Mastermind Dinners: Build Lifelong Relationships by Connecting Experts, Influencers, and Linchpins

Our guest may be the greatest connector of our time. He hosts the most exclusive events for entrepreneurs and brings brilliant minds and thought leaders together all around the world. His MastermindTalks conference or MMT has a lower acceptance rate than Harvard. I was honored to slip through the cracks and attend and it was one of the most epic conferences I’ve ever attended in my life. He’s the author of the bestselling book Mastermind Dinners. He’s been featured in Forbes and Business Insider. He’s an inspiration and I’m fired up to welcome Jayson Gaignard to the show.

I hope I live up to that introduction. I didn’t realize that before and now I’m anxious.

I want to start with a thank you because it’s special what you brought together and you’ve learned. From an experience standpoint, I always talk about the first impressions in going all the way through. Jayson, most conferences you go to, you barely know the organizer. You connect with a few people. I remember the first time we talked. It was 40 minutes. You genuinely cared and you talked to everyone before they get into your conferences and then you just kept going out. I get an iPad and I was like, “Look at this. I got an iPad.” You kept the conversations going into the conference. Before we get into your story, tell me a little bit about how you map the experience and how you got into that because it’s unbelievable.

I’ve been very experience-driven. It’s easy to focus on experience in the position that I’m in because I genuinely care about the people I serve and that’s key. I had a business before in the eCommerce space where I didn’t like the business and I didn’t like the people we serve so I didn’t care about experience. At MastermindTalks, we have 150 people and for context, we’ve had 18,000 entrepreneurs apply for an event that’s capped at 150 people annually. These are some of my favorite people on the planet. It is not lip service. I always say that we have 150 people at MastermindTalks. I’d have 135 of them at my wedding. I spend 90% of my social time with people in the community. We wrapped up a couple of small weekends where we were living a road life for two days.

Next, we’re going on a Disney cruise. There are 26 families going on this Disney cruise. I genuinely care about the people I serve and that’s foundational. It’s hard to preach best practices on experience design and that stuff if you don’t care about the work you do and people that you serve. That’s first and foremost. I had an idea to focus on customer experience in year one of our event because I didn’t have a lot of capital. We’ve grown MastermindTalks to this point without spending a penny on traditional advertising. There’s a saying that advertising is the tax you pay for being unremarkable. We’ve grown organically through word of mouth. It was sparked with that first event where my goal was to offer the best experience possible and capture that on camera. If I can capture that on camera, then I’ll never have to sell the event ever again because I’ll have social proof. For context, I had no event experience. I always say that ignorance, confidence and hard work can go long way when you’re an entrepreneur. I had no clue what I was doing. MMT is closer to a wedding than it is a conference in the sense of the curation and the seating arrangements and that stuff.

I remember that at the end of our event, there was a lineup of people lining up past the washroom. I’m like, “Why is there such a big lineup? Maybe I’ll tell them there’s another washroom elsewhere.” This was going on during the final dinner. I went to go see why and it was a lineup of people trying to leave testimonials. In that event, without me soliciting, we’ve got six hours of testimonials. We’ve never had to force that ever since. It’s been an area of focus and there are a thousand things that have reinforced it. There’s a great quote by Danny Meyer that says, “Business is like life. It’s all about how you make people feel. It’s that simple and it’s that hard.” There’s a great quote by John Paul DeJoria, who’s the Founder of Patrón tequila and Paul Mitchell hair salon products. He has a saying, “I don’t want to be the order business, I want to be in the reorder business.”

All this stuff plays into the whole notion of just designing a beautiful customer experience and the byproduct that is the word of mouth and all that stuff. I’ve got to give the hot tip from Joey Coleman. Joey came out with a book on the topic of the first 100 days. He delivered that talk at MastermindTalks in 2013 and he’s one of the best talk voted by the audience. Not only did he win the best talk beating my big-name speakers like Tim Ferris and all these well-known TED speakers, but he also had twice the number of votes of the second place winner. He ran away with it. His message is, “If you get the first 100 days of your customer’s life cycle right, you’ll have a customer for life.” He does a good job of talking about different ways to do that. All of that stuff culminated into me being very conscious about the customer experience. It’s funny because it’s a never-ending thing. Even though I get a lot of praise from a customer experience perspective, I’m like, “You don’t even know the things that we could be doing.”

Joey connected me with the MastermindTalks. Joey was a guest on the podcast. We were speaking at an event in Phoenix so we got to know each other. He connected me with it and never lose a customer again. He’s amazing on what he does. That’s something I noticed and it’s every touch point. You’re constantly sharing videos after we’ve already had the experience or continuing and going. That’s so important. I think what you said is more of, “If you don’t share your struggles, people won’t buy your successes.” We need to set the context to understand because you are very humble, Jayson. You’ll get onstage and be unbelievably humbled. Let’s set the stage. Both of us came from the grounds. You went into huge debt. I took over a million dollars in debt. I had to sell our house. I was on an air bed with my wife. It’s okay to share that because that’s where it started. I’d love to hear your story. Share it with the audience because it brought you to where you are now.

We’re setting a $250,000 in debt and I had a mattress. It’s all perspective. I thought it was rock bottom, but I guess not. I dropped out of high school. I started a service-based business, which can be a little interesting to scale. I pivoted into an online product business which we grew to about $7 million a year over four years with no outside investments. I was living my model of success. I was traveling the world, making a ton of money. With all that money and all that free time, I start to ask myself questions like, “Why am I here? Will I be remembered? How many people show up to my funeral?” I was not happy with the answers I was giving myself. I discovered that I was pursuing entrepreneurship for seven years and I built a business I hated to enable me to buy things I didn’t need and to impress people I didn’t like. I just realized I was not in alignment. I was on the wrong path. Even though I could have positioned the business for sale, once I realized my heart wasn’t in it, I had to get out.

[bctt tweet=”Investing in relationships is the safest investment you can make.” via=”no”]

I’ve had a few moments in my life like that and there are pros and cons to that. A lot of my friends were like, “What are you doing? Just coast it out for another year and get somebody to take it over.” I couldn’t do it. I became comfortable with scaling the business down to zero. Unfortunately, I was never good at hiring. Because that business cannibalized from the inside out, I started to pull myself out right away too quickly. The two things that were beyond my control on the way down were the nails in the coffin. When the dust settled, I was a $250,000 in debt in August of 2012. I had no business, no cashflow, I didn’t know what I was going to do next. My daughter turned six months old. I was struggling with that on many levels. I got married to my wife. When one door closes, another one opens, but it sucks to be stuck in the hallway. I was in a very dark hallway at the time. We were already in the Bahamas. We were getting married. I’m like, “We’re pulling through and we’ll make this happen.”

Truth be told, there’s a saying that a man’s loyalty is tested when he has everything and a woman’s loyalty is tested when her man has nothing. I never forget that. I jokingly say, “The general choice is she’s stuck around.” There are times when she could have jumped ship and she didn’t. I didn’t know what I was going to do next. All I knew is I didn’t want to do the same thing as far as pursuing something for the sake of money. Somebody posted on Facebook about an opportunity to go see Seth Godin in New York and participate in one of his little workshops. I’ve always been a big fan of Seth’s work and philosophies. I had no other obligations at the time so I said, “I’ll take the ticket.” I got there and it turns out that the theme of it was a connection economy. There’s huge value connecting like-minded individuals. At the time, I felt very isolated. I got back home and oddly enough, above 300 meters from here, I held my first dinner. I was planning to do one dinner. I just wanted to bring together a fascinating group of entrepreneurs and be in their presence because I was down and out.

The common misconception about me because Forbes is calling me one of the top networkers to watch and I have all these praise and accolades when it comes to relationships. The truth of the matter is, when I got married in 2012, I had two people show up to my bachelor party. I had my brother and my brother-in-law. I knew nobody. All the relationships that I have fostered have been in the last few years. How I filled it was we have a magazine in Canada called Profit Magazine, which is very similar to Inc. They list the top businesses locally and that stuff. They have this Profit 500 list. I reached out to a bunch of people who called and said, “I’m doing a dinner for all the Profit Magazine alumni. If you want to come out, here’s the date.” I got a 5% response rate at best and I almost canceled two hours prior because I’m like, “Nobody is going to see value in this. They’re going to think I completely wasted their time.” Thankfully, I didn’t cancel because I felt that I couldn’t because people were already on their way.

I went through with dinner. It turned out to be a big success and I got clarity that connecting people and being in the proximity of people who were doing amazing things was something I wanted to do to some capacity for the rest of my life and not necessarily as a business because I wasn’t monetizing these dinners. I’m always paying for them out of pocket. People thought it was crazy because I didn’t know how it was going to make rent the following month. The way I rationalized it was that I was considering bankruptcy. I was at the lowest I could go financially. The bank can take my car, they could take whatever measly assets I have left, but they couldn’t take my relationships. Investing in my relationships are the safest investment I could make back then and I still think it’s true to this day, which is why I still doubled down on relationships. I had that dinner, it turned out to be a success. I did multiple dinners, I had an opportunity to do an event with Tim Ferriss that fell in my lap.

You spent $84,000 of someone else’s money that you made a deal.

I was doing these dinners. I’m waiting for the house of cards to fall. Tim was coming out with the books. Tim Ferriss had two books under his belt at that time. The 4-Hour Workweek, which is a huge success. It was on the New York Times bestseller list for five years and The 4-Hour Body, which was also in the New York Times bestseller list and he was coming out with a book called The 4-Hour Chef. He discovered about three weeks before the book launched, that he was going to be banned from all retail distribution like Barnes & Noble, Costco, Walmart and everybody. The reason for that is he was the first big name author to publish on Amazon. The traditional publishing world, on some level, wanted to make an example out of him. Tim is one of the best book barkers I know so he scrambled and created these book bundles. If you bought five books, you get additional resources. If you buy 25 books, maybe he’ll do a webinar with you or something. He had this Hail Mary package that if you bought 4,000 books, he’ll do two speaking engagements.

BDD 163 | Building Connections
Building Connections: It’s hard to preach best practices on experience design if you actually don’t care about the work that you do and the people that you serve.


At the time, I was one of the first people to see his package. He was only offering one and I said to myself, “I have a great friend of mine who does these big events in Canada.” They have 2,000 or 3,000 people to show up to their events. I’m like, “It’s a great opportunity.” I sent them an email. This email is a great opportunity for anybody because Tim doesn’t speak that often and he’s never spoken in Canada up until that point. I ended up emailing him directly and I said, “I’ll take the package.” He said, “I’ll follow up later with the details and all that stuff.” The hairy part of the situation was that I had to come up with $84,000 within three days. I had 72 hours to send in the wire, which I wasn’t aware of initially. That was difficult on many fronts not only because I came off from a failed business and I was in survival mode. This is an industry I have no context and I have no experience in any way. I was raised in a family where you don’t ask for anything from anybody. I grew up around a very proud father who did everything on his own and took a lot of pride doing everything on his own. I’ve learned that it’s not the way to go through life, but I still have my hangups as far as asking for help because all my past businesses were built on credit cards. I’ve never raised money before.

I reached out to three friends. The first one said, “That sounds awesome. Come back to me with some numbers,” and I’m like, “Sure.” This is an industry that I had no context as far as how it works plus, I’m not a numbers thinker as an entrepreneur. I have a gut feeling around certain things to double down. I’m like, “Let me loop back with you.” The second person said, “It sounds awesome. Let’s start a business together 50/50.” I’m like, “That sounds great.” I have one more person to call. The third person said, “Come to my office tomorrow to pick up the check.” I didn’t talk any further. I hang up that phone. The following morning, I was supposed to show up at 8:00 AM but I was there at 6:00 AM because I was afraid that he’d call me and be like, “I have a change of heart or something.” I’m like, “I’m already outside. You have to give me that money.” He gave me the check. I deposited it and sent the $84,000 to Tim. I went from $250,000 in debt to $334,000 after I got that $84,000. That was the beginning of MMT. I didn’t have money to pay speakers initially so I took a page out of the X prize model, which was a prize for the best offers voted by the audience.

I brought in fifteen speakers and did a $25,000 prize and it worked out beautifully on many levels. Because I didn’t want to fall in the same trap as the business prior, I want to handpick the people that I got to serve so people had to apply. I was very lucky that we had a lot of applications only because of the caliber of speakers that we were able to attract. As I may have mentioned, ignorance, confidence and hard work can go a long way. I posted about the event publicly. I tried to get event planners to plan the event for me and they wouldn’t take it on because they were like, “There’s not enough time. It’s going to be a failure.” I was so scared to post this out to Facebook and to my social network because I’m like, “People are going to think that it’s going to be a flop.” It turned out to be a big success and has been quite an evolution over the last several years.

I want to unpack some stuff. First, you talked about how you were all isolated. I remember in one of your podcasts, CommunityMade, which is my wife’s favorite podcast. She loves going through the story there. It’s the email that gets open, “You are not alone.” That gets opened more than anyone else. Everyone feels that and it’s so interesting. When you think about experience or marketing, how do you make people feel that they belong and they’re together? That’s what you did so well. When I came here, I only knew two or three people and it is nerve-wracking. It was one of the first times that I didn’t wear a yellow tuxedo because I had fear. I was isolated. Now, I got over it. I wear it at airports, I wear it wherever I am. It was your event and I knew the people that I was around. I was worried about being judged and that’s that isolation and being alone. What have you learned from that because it goes so much into the experience and what you’re trying to provide for people is making them feel that belong?

Any industry that creates a sense of belonging in the community or wherever the case may be, that’s not going out of style ever. Especially with the way we’re leaning into stuff like social media and that stuff on how we’re getting more disconnected from that face to face. There are a ton of studies and tons of research. You made mention of the article ProBlogger teamed up with aWeber. This is back in 2012 and they discovered that there was one email subject line that worked across industries. It worked for male enhancement, it worked for personal development, potty training, selling cars and that was, “You are not alone.” Oddly enough, there’s an author named Keith Ferrazzi who wrote a book, Never Eat Alone. He wrote another book called Who’s Got Your Back. In that book, he interviewed 1,000 people at random and asked one question only, “Who has your back?” Surprisingly, 55% of people felt that nobody had their back. Even more surprisingly, 60% of those people were married. There are the writings on the wall. If you can create some brand experience where people can feel a sense of belonging, feel seen, feel heard and feel appreciated.

I look at the foundation of experiences and it overlaps beautifully with my relationship with my wife. When things are not going right, it’s always because she doesn’t feel seen or she doesn’t feel heard. If you want to have a client base that is wrapped around your finger, make them feel seen and make them feel heard. I’ll give you a case in point. We’ve had this success in the industry. We’ve had 18,000 applications. We get about 300 to 400 nominations a year, which aren’t included in that. That’s alumni that say, “I know somebody who’d be a great fit for one of your 75 spots.” Do you remember our MastermindTalks when we did those forums where it had a headshot of everybody and you circled your relationship like, “Did you know this person? Do you not know this person?” The number one reason why people come at MMT is not the content. Content is abundant. If you want to hear Tim Ferriss speak or Jim Collins speak, just watch their talks on YouTube. Content is abundant, but the community is scarce. The one thing about a relationship is, it’s a hard thing to quantify.

[bctt tweet=”Content is abundant, but community is scarce. ” via=”no”]

It’s easy to say, “This workshop did X, Y, Z for my business.” From an ROI perspective, it’s harder to say this relationship. That relationship may pay dividends a year from now, five years from now, ten years from now, you never know. Sometimes we don’t connect the dots looking backward either so it’s rather difficult. We tried to start capturing this and get a good understanding of what your baseline relationships are and what are they a year later so we can track not only how many people you met but how much deeper do those relationships get and all that stuff. All this to say, they included my name in those forums. Surprisingly, 17% of people in that room, 185 people who are clients of mine consider me as their best friend. The total for those two categories was over 50%, the other 30% was a teardown. I’m one of their best friends. The whole notion of experience of design is very much along the whole lines of that foundation of having people feel seen and heard. It is the foundation of relationships in general whether that’d be intimate or business relationships.

You must have a system. I’m thinking about all of these entrepreneurs and I think of myself. We have 100,000 plus fans come to our games. It’s so tough to keep that knowledge database of knowing them and being able to deliver that experience. You have a philosophy, the biggest fan and cheerleader philosophy, which I love because all we do is talk about fans. That’s the name of our company, Fans First Entertainment. How do you do that? What’s your system to the biggest fan being a cheerleader when your database is growing every day?

We have 150 people. We’ve had a couple of hundred other people go through MMT. It’s starting to get overwhelming, but it’s not at the scale of what you’re dealing with. We’re much more on the high touch side of things, but I can give you a little bit of an idea of a couple of things. There are two things that may prove helpful right now. One is the importance of relationship intelligence. You can reframe this as client intelligence. We call it relationship intelligence because the lines are blurred like friends and clients. They’re the same in my world. What are some of the things that you can capture on a person? It’s what they care about and who they care about is important. Important dates and milestones are important. Those are the two key ones. I teach a super-connected workshop, which is all about relationship building.

Instead of saying, “What’s your goal over the next year?” We’ll ask, “If we were to meet a year from now with a bottle of champagne, what are we celebrating?” We get a good understanding of where they are and where they want to go. If we can help them move the needle in that regards that’s a way of investing in that relationship, we also try to find out obstacles. If I asked one of my clients, “If we were to meet a year from now, what are we celebrating?” They say, “Hitting the New York Times for my book. I’m launching a book and I want to hit the New York Times.” The follow-up question to that is, “In order for you to hit the New York Times, what is something that you need to solve or overcome?” I get a clear understanding of their goal, a clear understanding of their pain point. I’m trying to remove or eliminate that pain points so that they can achieve that goal.

The final thing is their unique ability. I’m always trying to solve people’s problems through other people, connecting people. Those are the super connector ones, but fundamentally what every business can benefit from is capturing what they care about, who they care about and important dates and milestones. There are lots of different ways you can do that. It can be through intake forms. We’re blessed to be in the position where we can make people jump through hoops as far as how many questions they have to answer. You can pepper small things in there. We have these intake forms, which can be the basic stuff like name, email address, best mailing address and all those things. We would ask a question like, “What’s a $20 indulgence that you can’t live without?” They would say what it is. When we did our event in year two, when everybody went for a break and they came back to their seat, that indulgence was waiting for them. Whether it was Häagen-Dazs ice cream, McDonald’s fries or Krispy Kreme doughnut. That just took going the extra mile. There’s a saying, “Going the extra mile is never crowded,” and that’s our philosophy.

If you capture important dates and milestones and you capture what they care about and who they care about, the ways you can invest in those relationships are abundant. The beautiful thing is, you can get it from them directly. You can also get it through their social media. This can be done by you. There’s a friend of ours, John Goodman. They have 1,300 clients and somebody on his team has a specific Facebook profile where it says, “Jen, whatever her last name at their company name or dash their company name.” She’s friends with all their clients. Relationship intelligence updates the CRM and sends an update to John all the time. There are ways to build systems and processes around it, but those are key and biggest fan philosophy. That’s one of the six ways that I’ve discovered. You can invest in relationships. One is the common way to invest in relationships as resources. Understanding if somebody is here, they want to go there and provide them with resources or connections. That’s the basic way that most people do it. Another way is gifting. It’s a great way to invest in relationships. I’ll give you an example. Have you ever get a bad Christmas gift and somebody says, “It’s the thought that counts?” If they put thought into it, it wouldn’t be a crappy gift. A bad gift makes you feel unseen and the good gift makes you feel seen and heard. That’s the core fundamentals of gifting.

BDD 163 | Building Connections
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That’s another vehicle to invest in relationships with best clients. Good marketers are great at putting themselves in the shoes of their prospects and I’ve taken that same approach to business. I put myself in the shoes of one of my client. Let’s use the whole idea that they’re coming out with a book. If you put yourself in their shoes, what are some of their fears? I’m not going to sell any books. I’m not going to get any reviews. I’m going to get reviews and they’re negative reviews. What are some things you can do in that situation? You can promote the book for them. You can buy maybe a bundle of books to support them. You can be the first to leave a positive review on Amazon. I don’t care what author you are if it’s through your ninth book, you always look at those reviews for the first couple of days at least. Those are just other ways. You’re trying to find somebody’s most vulnerable moment and be their biggest fan to offset that. That is one of the best ways to invest in relationships. This all transcends into investing in your client base as well.

Another one is good old-fashioned gratitude. Gratitude goes a long way. There’s a book called The 5 Love Languages and I know gifting is one of them. I love gifts. I don’t keep them all. One thing I always keep is the notes. I always keep notes of gratitude. Those go a long way and they cost nothing. Coco Chanel said, “The best things in life are free, the next best things are very expensive.” Gratitude goes a long way and the last thing is taking all of these things. Gifting, gratitude, resources, biggest fan and applying it to their inner circle. If you want to care about somebody, care about who they care about. I recorded a video with my daughter because we’ve been all over the world. We’ve been to the state of some of the nicest Four Seasons properties you could imagine and it’s my daughter’s favorite hotel by far. This is your real house, but her favorite hotel is called the Chelsea Hotel in Toronto. It is a two-star hotel at best. It sucks, but we go there every time we come to the city because when we go to check in, they have a little check-in area for kids where they walk up these steps. There is a little chest with these little plush toys that cost $0.20. She gets a plush toy and then she gets the ring as big as a gong. That’s her favorite hotel.

Her favorite restaurant is a restaurant called Swiss Chalet. We’ve eaten beautiful five-star meals, but she loves this place that is equivalent of Denny’s in the United States. The reasons she loves it is because of the way they make her feel during that experience. There’s another chest where she needed to pick a toy or wherever the case may be. Her favorite grocery store is a grocery store I’m not a fan of and it costs too much money. Even though I’m not cheap, but if you can get it half price somewhere else, why would you go there? The reason she loves it is because they have little carts for kids that says, “Customer in training.” It’s a little cart and she started pushing those carts when she was three. If you want to care about somebody, care about who they care about. I know you get this. You applied it in your business. You’re well-known and widely respected for the stuff that you do. It’s amazing how many people know you and know what you do so I subscribed to all this stuff.

Thank you. We’re just trying things out. You went through it, but what are some of the fears? I was going back to when I released my book and that was one of those lonely times ever. You’re putting out a book, you’re throwing yourself out of the world, it’s scary. The people that are reaching out and sending notes made such an impact on me. From a business standpoint, I always talk about the friction points in an experience. What are the challenges? For a baseball game, you get nickel-and-dime. That’s why we made all of our tickets all you can eat and all that type of stuff. What are your biggest fears? Whether you have a restaurant, whether you have anything, what are the minor fears? Coming to a ballpark, parking is a little fear like, “Are we going to find spots? What time are we going to get there? Are we going to find a seat?” We have challenges because people can’t find seats. How do you overcome those fears and think about the experience? For you, Jayson, the videos leading up until the event were outstanding.

Here’s one thing that I would suggest looking back at it. I would’ve loved to get a call maybe from another member and say, “This is what’s coming up.” Thinking about that, luckily, I did know Joey. I called Joey Coleman, I talked to Tucker Max like, “Here’s what to expect. Let’s meet up that first night.” If you came up, I’ll tell you about the experience. If you came up and gave me a big hug the first time we saw, that’s unbelievable. It’s also helping with that process moving in and that was my fear. I went to your thing alone. I didn’t have anyone. At first, I was sitting at the bar. I didn’t know anyone. If every company looks back, what are the fears people have in experiencing your product, whether it’s small or big? How do you eliminate those?

Mapping that stuff out is crucial even just from a vocabulary perspective. Instead of using the word fear, use anxiety. When people’s anxiety rise, how can you address that? Those are great opportunities to make micro-investments into that relationship with your customer or your client base.

As members, I would love to call a first-year person and, “Here’s what I experienced.” They’re your biggest fans now and it’s vice versa. I’m thinking about that for people that come to our games that have never been to a Savannah Bananas game. I tell them what to expect like, “Get there early so you can get a seat. Go to this.” How helpful that would be in how many people? Don’t think you’re getting away from games, Jayson, because we’re going to our first game. You should be mentally prepared. Truth and dare, which one would you like first? What is your truth first? When you’re talking about fears, this is the real truth. What are some of your biggest fears?

In the context of business, this drives me unconsciously. I’m always terrified. At the good old days of MastermindTalks, I hear it a lot about other events. We’ve done a ton of things. Even the whole notion of scale, we’ve stayed the same size and increase the quality people and all that stuff. It always scares me that there’s ever rumblings at all the good old days of MMT. When it first started, it was better because you hear about other events and other companies and that terrifies me. You’re most successful when you’re most vulnerable. It’s easy to become very complacent and that notion always keeps me on my toes.

It’s expectations now too. When you first started, no one knew what to expect. We have our core group with our whole staff when they are in the first season and we never knew what to expect. All the games were selling out and there was a story every night and everyone talks, “That first year was so magical.” How do you recreate the magic of all those unexpected things that happen?

I did a behind the scenes tour of Apple in their Apple University. They shared this philosophy of surprise and delight. Every time you delight somebody, it becomes expected the following time. This is the never-ending hamster wheel that you always need to be running on. For us, there’s an expectation like last year’s format is going to be the same this year so we changed the venue. It’s a lot of work and some would argue unnecessarily like, “Why not just do it at the same venue?” We did that event in Park City at the end of September, we could have done that exact same event the following week because we had all the systems in place. We had all the meals lined up and all that stuff, but the reason we changed venue is that we redesigned the event from scratch and it creates a whole new experience. We hope that you can’t compare one year to the next coming in with these expectations every time.

Don’t think you’re getting away from the dare. We’re not skipping the dare. It is a game that we do at our ballpark called sing in the blank. What we do is we’ll have two people with a mic and we’ll play a song and as soon as it stops, you have to finish those song lyrics.

There are so many songs now if you look at the Spotify Top 50. It’s all disgusting rap songs. I’m a fan of rap, but some of it is harsh when you have a six-year-old daughter. I picked all these oldies that have great messages like Lean On Me. We sing that song all the time. It’s that I’m not as good on the spot.

I was going from your quote, “You never know the value of relationships until you need them.” When you hit rock bottom, which we all do, you’ll be left with two things: the integrity of your word and the strength of your relationships. Never tarnish your word and always invest in your relationship.

I’m going to incorporate that into my talks when I get off the stage. I’m going to have Lean On Me playing.

[bctt tweet=”Seven seconds of courage can change your life. ” via=”no”]

In the end, that’s all we have. When I pick songs, they are strategic. I want to go to the starting point, Jayson. My word for the year is the connection. What can they do to have a deeper connection with people? I’m going to segue into this a little bit. What I felt at your event is what you talk about. You had a pyramid and we cut through all the surface questions and get right to the root. I remember Philip McKernan talking about your greatest pain. It’s your greatest gift and bringing out your wounds in childhood. I’m sitting in a group and grown men are crying next to me. Then I’m on a bus going to a skeet shoot, which has me in a yellow tux. I cannot do skeet shooting. I didn’t hit anything. You’re connecting with these people in a real way and you brought on that deep connection. If you’re not hosting a conference and if you’re starting out right now, how can you get closer and connected?

There ared a couple of things. One question I get a lot is, “How do you connect with big name people?” That is a very common question that I get. Richard Branson and Bill Gates, they’re not looking for any more friends at this point in time. The best time to become friends with Tim Ferriss was back in 1997 before he wrote The 4-Hour Workweek. I’m a firm believer in investing in people like you would in business because amazing people become increasingly amazing over time. Having done this heavily, I can share hundreds of case studies of people that have grown exponentially over the years. Getting back to investing in people, we can all remember a time when somebody believed in us when we didn’t necessarily believe in ourselves. To find those rising stars and investing in those relationships and watching them grow is everything. That’s the one thing. Removing the allure of connecting with all these big names who are some great people that already in front of you that you can support it and find those rising stars, to me, it’s still a foundational principle that I apply all the time.

The other thing I’d add to that is when people have this whole notion of connecting with big names. I always point back to the whole dating world. There’s this thing from the dating world that like, “Would you date you?” It’s the whole concept of mate value. You want to surround yourself with people who are assets and not liabilities, people who are batteries and not black holes. People who can help us, whether it be personally, professionally, spiritually, emotionally, whatever the case may be. The one thing I always like to point to before you start trying to reach out and be friends with everybody is investing in yourself. There’s a great quote from the book So Good They Can’t Ignore You and that’s my philosophy. I have very much a long-term view when it comes to relationships. There are a lot of big names that I can connect with all the time, but I play the long game. To me, I just work on my own platform and write my own books and get better in every single way that I can be. When there is an opportunity to meet somebody, it feels that I’m a peer and I’m an asset.

I’ll give you a great example of this. I was at an event. I was speaking with Gary Vaynerchuk at this event. I never met him before up until that point. While he was onstage, I drink his talk. Two people run on stage to get a selfie with him. Gary loves this stuff. He wasn’t angry or anything. It was this VIP evening and I was having dinner at the back of the room and I didn’t know Gary. He was walking around nearby and there are two speakers sitting next to me. One of them was like, “I want to go and take a picture with Gary.” I’m like, “You go do that.”

Part of me wants to do the same, but I’m like, “That’s not how you build a relationship.” We don’t build a relationship by going up to somebody like, “Can I take a selfie?” Because on some level, you’re saying you’re not on their level. My friend went to go take a selfie and I was sitting there and then Gary was moseying by and turned to me and extended his hand to me. He was like, “I’m Gary.” I was like, “I know exactly who you are.” It just goes to show the importance. Those two people that ran on the stage, he’s never going to see them as a peer. Play that long game, amazing people become increasingly amazing over time and be so good they can’t ignore you.

You mentioned being a battery and don’t be a black hole. That as well is abundance creates energy and envy and scarcity drains it. If you bring energy, you lift people up. You mentioned gratitude, Jayson. In 2016, my word for the year was care. I had to hold myself accountable to that. I said, “I’m going to write a thank you letter every single day.” I started doing that and it hasn’t stopped. It’s how I start every morning and it’s over a thousand. It made a bigger impact on my life. You give to someone else without wanting anything in return. What happened from that is these connections because I’m not just saying, “Thank you.” It’s real. You have to make an impact on my life to do that.

Gratitude and energy, those are starting points for me and it sounds that for you too. You’ve got make sure that you understand that you’re not trying to get value from someone right away. You are playing the long game. The talent scout part I love too because it’s finding people that you don’t go to the top and reach out then. Anybody that reaches out to me now, whether they’re in school and they want to talk, I talk to them. I’m like, “I want to be there.” Mark Cuban did the same thing. I’ll never forget that I sent an email to him and he wrote back within an hour. I was 25 years old and I was blown away. It’s those little things that make an impact.

My wife’s biggest criticism of me is I will almost take a call with anybody. I always make sure it’s during the dead time like when I’m driving an hour and a half long drive to Toronto when I come to the city. I’ll make all of those calls within that short period of time. You never know the impact that you can make on somebody. Even having a conversation, not necessarily giving them any light bulbs. It can go a long way and that’s a way of investing in somebody when they’re most vulnerable in the early stage. Amazing people become increasingly amazing over time.

Invest in yourself. We have another quick game called flip the script. Jayson, you are now the host of Business Done Differently. You can ask me one question.

What is one thing you’ve done in the last few months that makes you feel proud?

My first thought always goes to family and then it goes to our team. I’m going to go family here because here’s something that I’ve changed. I’m obsessed with our business. I’m obsessed with our people. I care about them more than anything. My word this year is connection and the person I should be the most connected with is my wife and my son, Maverick. I changed my schedule. I go in early and I leave the office at 3:00 and I spend the whole afternoon with Emily and Maverick and that’s it. I don’t have email on my phone, I don’t have social media on my phone. I took it all off and I spend time with them. I’m proud of that because as someone who loves what we do so much, that’s something that I’m proud that I’m getting better at it.

What is one of the hardest things you’ve had to say no to?

BDD 163 | Building Connections
Building Connections: We can all remember a time when somebody believed in us when we didn’t believe in ourselves.


I’ve turned down three very well solid speaking appearances at good opportunities because of what we had for family commitments. I’ve said no to a lot of things. We’ve said no to LA producers that want to do a show on us because I don’t think our time is ready. I’ve said no to a lot of things from a business. I’m going to throw it back on you.

One of the bigger ones is an investment in the business. It’s very common in the business world to take on investment and scale. Similar to you, I have very similar values in the sense of the importance of family and time. I know what is needed and what needs to be sacrificed in order to grow a business and achieve hypergrowth and have an ROI for investors and all that stuff. It’s something I’ve turned down in the past and it was difficult than it wasn’t difficult because I’m clear about my priorities.

A lot of people see all these flashy things, whether it’s money, whether it’s an investment. We want to be able to own what we’re doing, be able to control, be able to take care of people, have our own pride and not change the purpose of our company and what we’re doing. We make sure that our people come first. We have to say no to those things. We’re on the same page. You said that if you want better answers in business, you need to ask better questions. You just gave two wild questions. I’m usually ready to rock and roll. It’s usually similar questions about the show, the experience. Are there some other great questions that you’re asking? One of the worst questions you can ask is, “How can I help?” They don’t know you enough. They should know you to be able to offer that, which you do. What are some of the other great questions that you’ve been hearing or that you asked?

It’s very common. Even friends of mine who were great at relationships began operating system autopilot, “How can I help you?” If I reach out to you, that doesn’t make you feel heard or seen. It does the opposite. It should be my role in this relationship to pull out to you how I can help you. I can say, “I can help you with this.” If there’s something you’re struggling with and that stuff. The champagne moment question is an amazing one, which is, “If we were to meet a year from now with a bottle of champagne, what are we celebrating?” You can contextualize that. You could say six months, you could say a bottle of cognac. There are different ways, but it’s a great way. Every time I asked that question, it makes people smile and it gives a way better answer than just, “What’s your goal?”

How often do you ask that question of yourself? How often do you ask, “What’s my champagne moment in six months, in nine months, in a year?”

I’m very clear about what those things are. I have my year booked out. One thing is that every time is like MastermindTalks. I hope MMT is another success and we have one of those a year. Your audience can go to We have a question list there that they can download. I don’t think it’s an email opt-in thing. Mastermind Dinners is the book I wrote. One of the things I talked about in the book is the importance of great questions and we’ve been cultivating questions a lot. If you go to, you’ll get access to a list of them.

If you’re trying to build experiences on how people feel, you’ve got to ask the right questions. You can’t just ask, “What do you do?” The question is so brutal. Some favorites quickly here. What’s a favorite book that you keep coming back to?

Seeking Wisdom: From Darwin to Munger. It’s on Charlie Munger’s quote. It’s a book written by a guy named Peter Bevelin. It used to be a harder book to get ahold of. You couldn’t get it on Amazon. It is amazing. Charlie Munger is the right-hand guy to Warren Buffett. It’s a beautiful way of thinking proximately being cognitive biases. It’s one of those evergreen books that you can reread every year and see it from a different perspective.

What’s your favorite part of your morning routine?

Drive my daughter to school.

What’s your favorite way to unwind at the end of the day?

Laying down with my daughter in her bed and putting her to sleep every night.

What about a magic moment? What’s one moment you’ll never forget? One that stands out when you think of something that made you happy.

I got a standing ovation at MMT at our first MastermindTalks event. That was a terrifying event. It was a terrifying event for me. I went to go speak on the stage to do the morning address. I had Tim Ferriss, Marc Ecko and all these people I consider superstars and mentors. That was the largest audience I had spoken and I was terrified to go onstage. We started late twenty minutes late because I was so scared at the back of the room. There’s a saying, “Seven seconds of courage can change your life.” To me, it’s almost like when I went skydiving. I’m terrified of heights. We only need seven seconds of courage for that door to open. You jump out once and you’re out, you’ll have no choice but to make it work. The same thing happened when I had to go on stage. I walked on the stage and I’m like, “Now I’m here. I’ve got to talk.” It worked out. At the end of the event, we had a couple standing ovations and that was memorable.

[bctt tweet=”You’re most vulnerable when you’re most successful.” via=”no”]

That’s a question I ask almost everyone and it’s amazing where they go because it’s always an emotional thing. It’s getting over a challenge. It’s special moments and it brings them there. When my son was born and the scares we had with that, I remember all these special moments and it’s amazing. Thanks for sharing. You said, “You can’t change the people around you, but you can change the people you’re around.” It’s well said and there was nothing other than I’m putting that in there because it’s a great quote. What’s one thing you’ve done to stand out in business and in life?

I follow my truth. I’m not trying to make that as hunky-dory type of thing. I have some unconventional views on business and scale and all that stuff. The common philosophy in businesses is “Grow as fast as you can, make as much money as possible.” I realized that didn’t make me happy. Just staying true to who I am and have no desire to scale and size. I want to scale and impact and scale trust ultimately with my community. Those are the areas of focus for me. That’s not something that everybody agrees to and not everybody is going to subscribe to. That’s my truth and sticking to that is a great way to stand out. It’s great to be yourself.

Have a deeper impact with fewer people and people are like, “No, you need to have so many people.” It’s that deep impact that makes a difference. You’ve got a lot of advice in your days from a lot of good people. What’s something that stands out?

Business is like life. It’s all about how you make people feel. It’s that simple and it’s that hard. I don’t want to be in the order of business, I want to be in the reorder business. On the personal side of things, Jim Rohn’s philosophy is “You’re the average of the people you spend the most time with.” Another one is “Some people are in your life for a reason and some for a season.” Understanding that you can keep people in your heart, but you don’t have to keep them in your life. I’ve had to make some difficult decisions when it comes to relationships and even with family. That’s an important thing for me to remember where I got those things from. I have an Evernote with 800 quotes. People are like, “When you speak, you speak in quotes.” They’re so powerful like a little snippet of text.

That’s what people remember. They remember the quotes. I want to go for the final question here. How do you want to be remembered?

My philosophy was like, “All that matters in life is how many people show up to your funeral.” I have a love-hate relationship with that notion now. I remember I went for surgery two to get my nose fixed because of the boxing incident. I was talking to the nurse and then I in mid-word and then I went out. I woke up eight hours later and I’m like, “That’s how death is.” You go out at any time, but you don’t know. There’s no countdown. I want people to show up at my funeral and I want to be remembered, but it’s released that hold a little bit. Part of me doesn’t care anymore. I just want to focus on the relationships I have and make as much impact while I’m here.

I hope I’m remembered as somebody who cared immensely about people, didn’t see people from a transactional perspective, supported a lot of people, helped them achieve their goals and helped them get clarity in general. Many people I know are confused and stuck into biases and other people’s opinions. One of the most beautiful things in creating the community of MMT that I’ve seen is a handful of people that go through it. They get in alignment with the work that they do, the relationship that they have, the life they want to live. To me, that’s beautiful. It’s a mixture of that stuff. When I’m dead, I don’t know anyway.

I read David Burkus who’s part of the group. He wrote a piece that goes, “With all our goals for next year, just show up.” I’m going to show up. I was like, “That’s brilliant.” Be there and be present and show up. Do the right thing and you’ll be remembered. I did it in my book. I started my book with my eulogy. At 33 years old, I wrote my eulogy, which was tough. Be there and things will take care of themselves and that’s brilliant. Jayson, I can’t thank you enough for showing up. We went down some crazy stories. You tried to sing a little bit, which was a disaster, but we had fun. I know this is going to offer so much unless there’s an offer a lot to me. Thank you. We have They have some resources. Where can anyone else learn more about this and this amazing thing you’re doing?

MastermindTalks, CommunityMade is this podcast I have where I do seasons on different topics. Season one was about scale where I share my viewpoints. I also bring other people who have different viewpoints. We could present them both then you make a decision off that. Season two is all about relationships. If you want to learn about the six ways to invest in relationships and all that stuff, which can be seen as stuff when it comes to relationship building and also building strong relationships with your client base customer experience. There’s a lot of overlap there and that’s and on all the traditional social media channels I can be found.

Jayson, I appreciate you. Thanks.

I appreciate you too. Thank you.

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About Jayson Gaignard

BDD 163 | Building Connections

Just a few years ago, I was stuck on the entrepreneurial ‘hamster wheel’ building a business I hated, to buy things I didn’t need, to impress people I didn’t even like. I was successful on the outside, but the heaviness of that success left me yearning for the lightness of being a beginner again.

I was bankrupt on every level..Emotionally, spiritually, financially, even physically since I had built my business, like so many of us do, at the expense of my health. Add to that, I had just moved to a town I didn’t like, entered a marriage I wasn’t ready for, and was having an incredibly hard time adjusting to being a new father. But rock bottom became the solid foundation on which I rebuilt my life. Fast forward to today, and my life is virtually unrecognizable from what it was only a few short years ago…

The whole experience made me burn boats in search of something new..Something fulfilling. I didn’t know what this would be at the time but by the end of our first MMT event in May of 2013, I knew I had found it.

The speed in which I’ve turned my life around is thanks to one thing, and one thing only… My relationships. The rarely spoken about truth when it comes to success is that nobody does it alone.

I’m not self-made. I’m community made.

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