Why Relationships Are the Greatest Investment for Entrepreneurs with MastermindTalks Founder, Jayson Gaignard – EP 283

Justin Donald: What’s up, Jayson? So good to have you on the show.

Jayson Gaignard: It is an absolute honor, man. I adore you. So, it’s great to be here.

Justin Donald: Well, heck yeah. It’s funny, I just learned right before we went live that you really have turned down most, if not all, podcast requests. So, I’m feeling very humbled and honored to be able to have you and host you here today. So, thank you.

Jayson Gaignard: I promise you, I wasn’t saying that to stroke your ego. It is true. You will not find me on any other podcast for the majority of 2025 and the beginning of 2026. But again, when your email landed in my inbox, I was like, any opportunity to spend time with you is obviously something I’m looking forward to. And I know you care deeply about your audience. So, the fact that you think I could serve them is, yeah, I just feel incredibly honored. So, thank you.

Justin Donald: Well, thank you. I mean, the feelings are mutual and I know you can serve our audience. I am thrilled about the ways that you can serve our audience and your expertise and I’m really excited to get into your story, but I also want to get into, like, what I think your core genius is, where I believe you’re an outlier. So, we’re going to have a lot of fun talking about curation and events and thoughtfulness and like, high touch, high quality experiences. Like, I do think you are world class in that category, so I want to get into that for sure.

But you also have a story that is incredibly powerful. So, for people that don’t know you, I mean, anyone that’s looked you up or followed you knows that you’ve had your fingerprints on some of the most impactful communities, impactful membership organizations, early days with some of the biggest name people out there, people that have gone on to become household names. And a lot of that started with you and inside your communities. And so, it’s cool.

As a member of Mastermind Talks, I’ve seen it firsthand. I’ve experienced it. I’ve felt the intention and really just like precision to detail, thinking through every single bit of the programming. Like anytime I leave something that you’ve done, my team is like, oh, here we go again, because Justin is just not going to let up. He is going to be like, we need to do this and we need to do that, and why aren’t we doing this? And so, I really have you to thank for a lot of the cool things we’ve put into play in our mastermind and at our live events because I think you do it the best in the industry.

Jayson Gaignard: Well, I listen, I hope I live up to that incredible introduction. I appreciate it and I’ll be honest with you, when we hosted you at your first MMT, I was a little anxious in the lead up to it because you have such an incredible reputation amongst friends of ours. And it was an honor to have you, obviously, join us for that three-and-a-half-day live experience and just to be in a position of service to somebody like you.

So, the fact that I truly see you as a companion on the path when it comes to creating a container for people to show up powerfully and designing live experiences and that kind of stuff. So, yeah, I’m going to let what you share land. I appreciate it.

Justin Donald: Yeah, please do.

Jayson Gaignard: And I’m looking forward to seeing how we can help your audience with it.

Justin Donald: Cool. Well, let’s dive into some of this, and we’ll eventually talk about the book that you’re writing. It’s not out. It’s not ready. And I know based on how attentive to detail you are in your events that you’re going to be the same way, you’re going to obsess, you’re going to over-obsess, you’re going to obsess to the nth degree, the way many of us have when our product just never feels like it’s a finished product. And there’s always more we could do. It’s never complete. You’re going to go through that, and I think you’re going to go through that to a greater extreme than the rest of us. But I’m excited for when it is done because I know you only put out world-class content and programming.

Jayson Gaignard: I appreciate it. Well, you’re sharing that comment when I’m in the thick of it. My publisher hates me right now with all the deadlines, but…

Justin Donald: Deadlines. And deadlines are the worst when you’re trying to be in a creative flow. Oh, it is so stifling.

Jayson Gaignard: It is challenging, but constraints, people like you and I oftentimes need constraints. So, it’s been good in that regard. But similar to you, we roll around in circles with some very brilliant people who’ve put their life’s work into books. So, there’s a standard, one could say. So, I’m just trying to follow in your footsteps, and hopefully, my book makes half the impact yours does in the marketplace.

Justin Donald: Well, it’s super kind and I know that it will. And I’m really excited to dig in a bit to your story. Before we do though, I’d love for you to talk about just what MMT, Mastermind Talks, was and is, why it became your life’s work? This is early days, so now, people talk about masterminds and it’s almost commonplace that entrepreneurs are in. There’s a plethora of different masterminds.

Early days, you are one of the original. I mean, when I think of the three biggest movers and shakers in the mastermind space, you are the top three, right? And so, you, from an event standpoint, really kind of leveled up. I mean we can all say that if you think about– there are people I think that had a big name in the coaching space that started putting people together. I think you did it differently. I think you found amazing people and then you created this safe place for people to open up and dream big and hold each other accountable. And I’d love for you to talk about just the evolution of MMT.

Jayson Gaignard: Yeah, I mean, there’s definitely, the word mastermind gets thrown around a lot. And usually, it’s a way to command a higher premium for what would normally just be an event. So, yeah, we can jump into definitions and all that kind of stuff, but ultimately, I mean, the short version of it is I had an e-commerce business that was relatively successful and did that for a handful of years to the point where I realized it built a business I hated to enable me to buy things I didn’t need, to impress people I didn’t like.

I never felt in alignment with the business. We sold concert tickets and sporting event tickets, and we were the second largest wholesaler in Canada, which is where I’m based out of. But we sold millions of dollars of hockey tickets. I never went to a hockey game. Every time I’d go to a concert with my wife, I’d count the seats off in the distance to figure out how much money the artist made and that kind of stuff. So, I was never in alignment with that business effectively.

And there came a point where I realized I want to transition out of that business. And unfortunately, I was in a position where I could have sold it, but it would’ve taken a year or two for me to kind of transition out effectively. And I decided instead to scale that business down to zero. And I was like, well, as long as I have a little bit of cash left in the bank, when I’m done scaling down, then I’ll have a little bit of runway to find my next thing.

Unfortunately, two things happened that were beyond my control that landed me a quarter million dollars in cash debt in August of 2012. On September 1st, I got married to my wife, and on September 1st, that same year, my daughter turned six months old. So, there’s a saying that when one door closes, another one opens, but it sucks to be stuck in the hallway. That was a very dark and cold hallway for me at the time. And it’s one thing to be like a quarter million dollars in debt, but it’s another to be a quarter million dollars in debt and not have any cash flow, any business, any investments. I felt like I was steering a parked car at best.

Justin Donald: Oh, that’s intense.

Jayson Gaignard: Yeah, it was an interesting time, for sure. It was definitely a trying time, but I had a friend of mine, or more of a loose connection, post on social media that she had an extra ticket to go see Seth Godin in New York.

Justin Donald: Nice.

Jayson Gaignard: And I’d been a fan of Seth’s work, but never had an opportunity to kind of see him speak live. And because it was free, I knew I could probably convince my wife that I can go and went, and it turned out the theme of it was the connection economy and how there’s huge value connecting like-minded individuals. And at the time, I just felt very isolated. Again, I was kind of at rock bottom. I didn’t have any friendships.

When I got married, in advance of that, I had a bachelor party and I had two people there. I had my brother and my brother-in-law. I knew nobody. So, when I caught my flight back home, I dreamed up this idea of hosting dinners for entrepreneurs, and just being a fly on the wall of their conversations. And the first one I did, I made a commitment, I put it on the calendar, I booked the restaurant and invited. Because I didn’t know anybody at the time, what I did was I looked through a local magazine similar to the Inc. 5000 or what have you, found local entrepreneurs and said, hey, I’m doing a dinner with other Inc. Magazine alumni. If you like to join, like here’s the date and it’s on me and that kind of stuff. I don’t know what my response rate was. It was probably 5% at best.

But ultimately, I filled the dinner with eight people and I almost canceled that dinner two hours prior because I’m like, nobody’s going to see value in this. They’re going to think I wasted their time. But from an integrity perspective, I couldn’t cancel. And as people showed up, got them to sit down, I didn’t know, I was terrified at the time. I didn’t think I could eat food and keeping it down. But ultimately, conversation didn’t skip a beat for four and a half hours.

And I got clarity that being in proximity of fascinating people was something I wanted to do to some capacity for the rest of my life. And at that time, I was paying for these dinners out of pocket, and we didn’t know how we were going to make rent month over month. But the way I rationalized it was that the bank could take my car or they could take whatever measly assets I had left, but they couldn’t take my relationships.

Investing in myself and investing in my relationships were really the two safest investments I could make. And did a couple more dinners and then I had an opportunity that fell in my lap to do an event with Tim Ferriss. And that was as a result of me buying or committing to buy 4,000 books, which there’s a whole story there.

But fast forward a little bit, we held our first MMT event in Toronto, and we were planning just to do the one event. The thought behind it was, if I could focus on something for six months, then that’s going to keep me from spiraling into a dark place. So, I’ll have a project to focus on, then I’ll figure out what kind of business I’ll do in the future, whether it’s another e-commerce business or what have you. But if I could have 150 fascinating entrepreneurs at the event, in theory, I just added 150 fascinating people to my world.

Justin Donald: That’s right.

Jayson Gaignard: And that was what I was most excited about. And I always say ignorance and confidence can go a long way when you’re an entrepreneur. I had no clue how to put on an event, and as a result, it was much closer to a wedding than it was a conference and that there’s a handful of magical things that happened at that first event that were really, I can’t take credit for. It’s just the stars aligned in really beautiful ways where the speakers stayed the entire duration of the event, which created a really beautiful environment.

People just connected so deeply throughout the event, as a result of the curation that we had in place. And we decided to do a second event, in 2014, and it went off without a hitch again. And in fact, out of the 15 speakers we had out of that first event in 2013, 10 of them came back as paid attendees the following year. So, that’s how we started to shift away from talks from a stage and gurus and that kind of stuff, and more into a community. And we’ve continued to lean into that year over year for the last 13, 14 years now.

Justin Donald: Well, I love that. And as someone who also runs events, there is something powerful and palpable about having people that want to be there the whole time versus show up and leave because they had a scheduled speech. It is a totally different dynamic. And I don’t care for the show up and leave. I want, if you’re going to do it, be here, be immersed in the community, fall in love with the culture, right?

Jayson Gaignard: Yeah. It changes dynamic so much. And in fact, I mean the beautiful thing about our first event is because the speakers stayed and we keep our agendas historically, like, as a surprise, you’d be in the audience and you don’t know if the person next to you is the next person to step on stage. So, it just creates this beautiful environment. I reflect back, there’s an event we did in 2019, which was one of my favorites where we had a guy, his name is Jim Estill, who’s a brilliant entrepreneur, grew a company to $2 billion from the back of his car. And he was an attendee the entire event. He leaned in, played full out. Everybody thought he was just like a normal attendee and loved him. And then on the final day, like we brought him to the stage and he was just surprised.

Justin Donald: That’s so cool.

Jayson Gaignard: It makes a unique environment for sure.

Justin Donald: Yeah, there’s no doubt. And I joke with people that I obsess over the details and the quality of the events we do. Like I overanalyze, I spend all this time and, and it’s funny because deep down I know, if you just put amazing people like a well-curated room, if you are highly selective in your process of who gets in and you just put them in a room, amazing things are going to happen. Like, the power of the room is really the power of the people that are there.

But then you can put a little bit of like, emphasis and a little bit of pizazz into how quickly you can get there, how quickly you can uncover things, how quickly you go deep, how quickly you curate a trust-filled room. And the deeper the conversation right out of the gates and having something social to kind of kick it off and having really nice touches along the way, different things that I think you’re great at where it’s like, hey, let me recommend some people that you connect with that are like you or in a similar season or have gone through what you’re going through. That intentionality, I think, helps people open up and it helps create the heck yeah moments early into an event, which then just resonates the whole rest of the event. And I’m curious about your thoughts on some of what I just shared.

Jayson Gaignard: 100%. I mean, curation is what makes us very different than others in the space. And we get confused oftentimes with organizations like EO or YPO, which are great organizations, but they’re criteria-based organizations. As long as your business does a certain revenue figure or you have a certain headcount, you are in. And they’re great. I mean, YPO is 20,000, 30,000 members, and EO is creeping up there as well. And they serve a fantastic need.

But it’s very different than being found, like finding yourself in a community of companions on the path where there’s shared values in place. One of the realizations I made many years ago is how you run a community of 150 entrepreneurs. This is exactly how you’d run a company of the same size. And anybody who’s been in business long enough knows that when you’re hiring someone, if you don’t keep core values at the forefront of that hiring process, doesn’t matter how impressive somebody’s LinkedIn resume is, they’re ultimately going to be a bad hire further down the road.

And that is what makes an environment like ours unique is there’s three boxes that somebody needs to check in order to be considered for MMT. The first is demographics. They have to be an entrepreneur or have built something of scale in the past. The second is our value graphics, which are essentially our guiding principles for their community or our core values. So, we have a bunch of ways in the exploration process that we suss that out. But again, it’s very similar to a hiring process. And then the third is synergy. We want to ensure that those we bring into the community can be a value add based on their experience and expertise. And we also want to ensure that based on where they are and where they want to go, that the community can kind of serve them.

And if somebody checks all three of those boxes, plus a layer of validation that we do beyond that, then they are effectively extended an invitation. And the majority of people claim their invitation at that point because they know how much time, effort, and energy goes into our selection process. But it’s rare to find yourself, obviously, in an environment like that.

So, even myself, there’s only one event I go to currently, because I haven’t gone to events in so long. My social cup has been so full as a result of the work that I do. But there’s one event or mastermind that is put on by a friend of mine named Stu McLaren called Village Impact. And it’s a two-day mastermind that they put together. They bring all these incredible thought leaders. There’s that saying, if you’re the smartest person in the room, you’re in the wrong room. That is not a room I deserve to be in, but somehow, I squeak my way in every year. And they do it to raise funds for their charity.

But I share all of this because the care is palpable. Like, when it comes to the selection process as far as who’s in the room, everyone’s there for a reason. When it comes to the actual design and the intention, like you can feel it. And again, those spaces are just very, very rare. So, the type of people that come to MMT, historically, have been jaded by other events and other masterminds. They don’t really participate in many of those anymore. And we always say like, we condense decades of networking into a few short days. My life is basically trying to connect with fascinating people. Suss out like the real great ones, the ones who are trustworthy and that kind of stuff, and then put them all together at an MMT once a year.

Justin Donald: Yeah, I absolutely love that. And I mean, we could go through the laundry list of people that kind of got their start in your mastermind from Tim Ferriss to James Clear to Esther Perel to Dan Martell. I mean, the list goes on and on and on and on, and it’s really cool seeing what many people consider some of the industry experts or thought leaders in their space of our time, but imagining them way back before any of this existed, before they had a book, before they had a course, before they had a media company, before they had an anything, and to think like, well, how did they get to where they are?

Well, they had a group of people that poured into them, that they also poured into, that they shared ideas. They got uncomfortable and exposed what they were thinking, how they were feeling, what they wanted to do at risk to their own ego, and had the support, or even people being constructively critical, but helping them get to where they’ve ultimately gotten to. It’s really beautiful.

Jayson Gaignard: Yeah, I mean, it’s one of the funny things as I’m in the process of sharing my book, which is in the final stages of editing right now. So, I have beta readers, I have their eyes on it. And even people I’m working with, whether it be the publisher or illustrators, they often say all the amazing names, I guess you could say, that are found in the book. And I actually bring voice to it in the book that this philosophy I have, that be a talent scout because amazing people become increasingly amazing over time.

Dan Martell was not a big name necessarily when I met him, nor was like Tim or Esther Perel or Lewis Howes or just all these names. But when you find people, so you know them, like you find somebody, you’re like, oh, you’re a rising star. Like, you are so undervalued in the marketplace. It’s only a matter of time. And they are just fascinating. And I just forge relationships with those type of people and figure out if there’s ways I can remove roadblocks on their way to kind of stardom.

And over time, relationships compound into incredible things. And that is now, I’m, I guess, “seeing” the effect of it, 10, 15 years later. But I’m beyond excited and over the moon as far as what are these relationships going to look like when I’m 50, 60, 70. So, really looking at relationships through that long-term lens, planting a lot of seeds, never overlooking anyone, and all that kind of stuff. Inevitably, your network will grow into incredible things you could have never predicted.

Justin Donald: Yeah. And if you’re willing to offer more to other people, if you’re willing to kind of be there and serve in a way that you truly, authentically feels in that person’s best interest. If you show up with a goal of– a lot of people show up to transact, if you show up to give and to serve and to add value, you don’t do it for this. I do think that the reason you do it, like, it has meaning, it matters, but that reciprocity is a powerful thing. And people don’t forget it. Even if you are okay with them forgetting it, they don’t forget it. And it really cultivates a really dynamic and unique relationship and ultimately, friendship with a lot of those people.

Jayson Gaignard: Well, you know, I had to really sit with this. There’s a saying, I think it’s from James Clear, that the book that changes you is the one you write. And when I was writing my book, I was trying to stiff arm the idea of transactional relationships because there’s so many books in the marketplace that are about transactional relationships, and they feel icky to people like you and I. And I was going through the lens of like, I’m so above and beyond transactional relationships. I’m all about transformational relationships. Like who are those companions on the path that you’re going to grow old with?

And through the different seasons of your business and all that kind of stuff, the truth of the matter is we need both. And especially when you’re early on in your journey, you need transactional relationships. You need a good lawyer or mentors or whatever the case may be, who can help you bridge the gap from where you are to where you want to go. But there comes a point where your fulfillment matters more than your achievement.

And having a yacht sounds cool, but it’s pretty boring when you’re sitting on it alone. And I think that’s the challenge that most entrepreneurs have is they’re focused purely, if you look at it as a spectrum, purely on transactional relationships, then they start achieving those goals and then they look around and there’s nobody else there. It’s lonely at the top of the mountain, so to speak.

So, there’s this balance, and the way I like to frame it is, there’s this beautiful story about these British rowers. I have it in the book where they were trying to not only get into the Olympics, but actually win like a gold medal. And they had a pass at the Olympics and it didn’t go well. So, they had four years to train. And the North Star question that they used throughout those four years was, will this make the boat go faster? So, if it was going to the pub on a Saturday night, will this make the boat go faster? No. So, they wouldn’t go to the pub. If it was waking up early on a Sunday morning to go rowing, will this make the boat go faster? Yes. Then I guess we’re going rowing.

Ultimately, they won, I think it was the 2012 Olympics, gold for Britain, which was like the first time in 80 years. So, I think that’s one filter. If you are looking at relationships transactionally of like, will this make the boat go faster, will this help bridge the gap between where I am and where I want to go? And again, all of us need those types of relationships, but more so especially when we’re early on our journey.

And then the other spectrum, the transformational relationships, I think of it like, Marie Kondo of, when she’s decluttering a house, will this item, does it spark joy? And I look at relationships through the same lens. So, somebody like you, do you bring me energy or do you sap it away? And people like you, people like I bring into MMT, I mean, I’m on fire, after a dinner or whatever the case may be. So, those are the relationships I’m trying to cultivate more in my life. And that’s been my filter.

Even when I started MMT, we were having a hard time figuring out how do we select people because again, all the other organizations out there are criteria based, and the question I asked myself was, what do I want to have dinner with this person? And if the answer was no, I didn’t care how successful they were on paper. So, we need both of those relationships. Those are the two different kind of filters I have, but again, especially as you become more successful and your fulfillment matters more than some of those ambitions, you start shifting more of your energy to those transformational relationships that really give you energy.

Justin Donald: Yeah. And I think that the way you can create kind of like a best-in-class room is with having that incredibly low acceptance rate. So, the way we do it, the way you do it, I mean, I think it’s imperative for Lifestyle Investor, and I know you’re exactly this because I know your acceptance rate is lower than a lot of your elite institutions. You say yes because it’s the right fit and it’s not criteria based like you had mentioned.

But I also think that in the day and age now of masterminds becoming more commonplace, which I’m excited about, I think that’s great. More masterminds, better, like more people have an opportunity to get in them. I think being in some sort of a think tank that can positively impact and influence you and give you an outlet to positively impact and influence others is incredible. I think everyone should have that group, but we live in a day and age where the main criteria is, can you afford it? If you can, you’re in. And by the way, we know all the people that do that.

Jayson Gaignard: I belong to a group where that was like, behind the scenes of curation, if you can cut a check that separates the talkers from the real players.

Justin Donald: That’s right.

Jayson Gaignard: And I mean, it works, but it’s not going to create the environments like you and I are creating.

Justin Donald: And it’s a testament when people actually show up to those events because you and I and many people that are watching and listening that they’ve experienced this, where they go to an event, they go to a mastermind, they go to a conference, they go to a whatever, and they meet so many people that just aren’t the right fit for them, their values misaligned. Maybe it’s more geared towards transactional relationships. What can you do for me right now?

And you leave it like, gosh, is there anyone? Like, there’s no one here. I had to sift through all these people, hundreds of people to find this one or these two people, and they’re like, the diamonds in the rough. You’re like, yes, this is great. But our number one compliment and I can pay the same compliment to you, the number one thing I hear when someone attends one of our live events is there’s not a single person that I met that I don’t want to get more time with. Like, every single person blew me away and I just want more and I can’t believe it, and I’ve never been in a room like it, and I can pay you that same compliment of everyone in that room is doing incredible things, has a humble heart, is so eager to connect, so down to teach. It’s powerful when you find those groups. There aren’t many of them. And when you find them, cherish them.

Jayson Gaignard: Absolutely. I wholeheartedly agree. I mean, for me, I’m in service to like the container and having quality people in that. And we get this all the time, people who can cut a check easily to come to our programs and we have to, sometimes it pulls on the heartstrings because maybe they’re a nice person or other case may be, but you’re like, the fit is not there. The way, the thing that always helps me make that decision is like, I ultimately have to defend and argue for every single person in this room and give a compelling argument as far as like why I picked them and why they’re there. And I can’t, one day, be like, ah, this one was for the sake of money or what have you. Because I mean, the quality of a community comes down to the quality of the people effectively.

And to what you said, if you get that right, people look at our events, and I appreciate all the nice comments at the beginning about the event and all that kind of stuff. I think people get a little mistaken and not you, but people on the outside. Like our last six live experiences have an approval rating of 9.73 out of 10 or higher, which is a big, like, great number to throw around, and people automatically think it’s because we have great speakers or beautiful stages and all that kind of stuff. No, we’re very specific as far as like who we serve. We want to make sure it’s going to move the needle for them.

And again, our curation process is everything. So, even like, if we’re considering somebody who’s not a perfect fit, I’m like, ultimately, we’re not going to feel the pain maybe early, but we’ll feel the pain in that approval rate down the road, either by them because they weren’t a right fit because they were looking for deals and there was no deals to be had, or we created a safe environment where we kind of frowned upon that, or other people are going to rate it lower because they had an interaction with this person.

Justin Donald: Yeah. They had a poor experience because of one bad apple.

Jayson Gaignard: Yeah, 100%. So, you’re only as strong as your weakest link in this business. So, we try as best we can to, again, suss those people out far in advance.

Justin Donald: Yeah. Well, it shows, and I love finding the groups that do that because most of them do not. And like you said, I don’t care how much money you have, I don’t care how successful you are on paper. If you don’t align with our core values of who a member should be, you just can’t be in. And for us, humility does play a role. Like, we don’t want egomaniacs, and are you willing to share the gifts and talents that you have? Are you eager to learn and grow yourself recognizing that you haven’t arrived and never will arrive? It’s like those three things are so important to us.

Jayson Gaignard: Those are beautiful. I got to say, we spend 30-plus hours, if not more, really identifying like what are our guiding principles for the community. And what you just shared was so beautiful and eloquent. I just need to pause and share a spotlight on it because again, that level of thought and care is just not common in this space, whatsoever. So, thank you for sharing that.

Justin Donald: Well, thank you for the kind words. You once said this, that investing in relationships was the safest investment that you could make. And I’m just thinking for our audience, for lifestyle investors, those aspiring to be lifestyle investors, if they think about their social capital, how does that tie into an asset strategy? Like, how should that be looked at? I mean, for you it’s been magical. You’ve been able to build your organization through that. It’s also incredible because even in the moments where you were in debt and you needed more money, you still didn’t waiver on your criteria, which I think is– I mean, very few people can do that. Very, very few people can do that.

But there’s an aspect of your relationships that can make you and break you depending on how you show up. And I think for someone like you, they’ve made you. You have one of the most incredible networks that I’d love to hear how you would suggest those watching, listening to this, to think about those relationships and how to even level up their relationship game.

Jayson Gaignard: Yeah, it’s tough because oftentimes, you don’t value something until you have a rock bottom like experience. And that is the case for a lot of friends of mine and entrepreneurs that shift to valuing relationships is oftentimes, there’s a point when they look in the mirror and they realize there’s nobody who has their back. There’s a great book by Keith Ferrazzi called Who’s Got Your Back. And in it, he actually didn’t publish this in the book, but he told me and confirmed it that they interviewed a thousand people at random for that book. And they asked them one question and one question only. Who has your back? Surprisingly, 50% of those people felt like nobody had their back. Even more surprising, 68% of those people were married. So, yeah, that’s a hard one to stomach.

But one of the key features of being successful in business or entrepreneurship, specifically, is staying in the game. And I got this nugget of wisdom from a friend of mine, Phil Caravaggio, who sold his business for $200 million to private equity. And it was…

Justin Donald: Not bad.

Jayson Gaignard: No, he did well and it was like bootstrapped.

Justin Donald: Good for you. Nice job, though.

Jayson Gaignard: He has a beautiful relationship with money, too. Like he still lives in a two-bedroom rental apartment and he has all this money in the bank. So, he’s a very interesting character.

Justin Donald: That’s awesome.

Jayson Gaignard: But his frame of never getting knocked out of the game is so true, because if you’re in this business space for long enough, you see so many that unfortunately are knocked out for whatever reason. And also, you hear of people who really were able to like, stay in long enough and then they get a big exit out of the blue or what have you. And when you hit that, those rough patches, surrounding yourself with a core group of people who truly have your back is invaluable. It enables you to take bigger swings.

Like, there’s an interview between Dr. Becky Kennedy, who’s a parenting psychologist. I think she wrote a fantastic book called Good Inside, which is huge. And she was on Shane Parrish’s podcast and she talked about parents, oftentimes, when their kids enter teenhood, there’s this natural inclination from a developmental perspective to kind of separate themselves from their parents. And parents can kind of feel like useless in that phase and feel not needed effectively.

And one of the things that Becky Kennedy said, which I thought was interesting, she said, basically, kids are becoming nomadic and they need to have a safe place to come home. And as they come home, as long as there’s that tight tethering to home, then they have the courage to go out and explore and then always have a safe place to come back to. And when I heard that, I was like, it’s the same thing for entrepreneurs to some degree. If you have that core group of people that have your back, you can take bigger swings in the marketplace. So, you have a safe group of people to come back to who, again, will dust you off, pick you up, support you, fund you, give you resources, whatever the case may be. So, there’s that element of it.

And then also, to some degree, like all opportunities come through relationships. So, the more relationships, deep relationships you’re able to forge and get those people to fly in formation whenever you need them when it comes to like support or what have you, it’s an absolutely kind of invaluable asset.

So, I'm obviously a firm believer in the importance of social capital. My only hesitation, and it's so tough because like when I talk about relationships, I talk about investing in relationships and I use terms like social capital and that kind of stuff. I've always been a little reticent about it because it's easy for somebody to fall into the transactional trap as a result. So, that's the only thing to be kind of cognizant of. But, yeah, I mean, again, relationships have saved me in a plethora of ways, and this transcends beyond business. When I had health challenges at the beginning of the year, I knew like one of my biggest challenges is like telling people, because I'm going to have so many resources and connections and people that want to help come my way that I have to be very conscious of like how I manage my energy.

And lo and behold, like people showed up powerfully and beautifully for me during that time period. So, yeah, I mean, I'm obviously a firm believer in it, and I think it's an area of focus. And nothing is worse that like when you need relationships, and you realize they don't have that depth. You can't turn back the hands of time. So, it's much better to plant those seeds far in advance, invest in those relationships, and hopefully you don't need them, but should you, they're there to support you.

Justin Donald: Well, and I love the story that you shared behind closed doors at the last meetup, at the last event, about some of those people that showed up in your darkest hour, in some of your biggest struggles that were so selfless because that's who you curated as your member base, your friend base. But man, you had given so much that people were just eager to give back to you, and it was probably hard to receive.

Jayson Gaignard: Listen, I give that talk every year for the last five years because there's always more people that have showed up for me in that year span. So, like even this year, I'll have some kind of talk where I acknowledge some of the people in the room who've showed up for me in a plethora of ways. It's just inevitable that like life has setbacks and hard times that we all have to navigate and all that kind of stuff. So, when you actually pause and look around and have a peer group of people who've whether it's open the doors to opportunity or help you navigate obstacles quicker than you would be able to alone.

I mean, it's one of those things, once you start to see it, you don't unsee it. Like, that's why it's the most important thing for me because I can look back on 10, 15 years of my life and show all the different inflection points and transformations as a result of somebody I met randomly at an event or somebody who was introduced to me randomly and we became super close friends. So, once you're anchored to it, it's everly.

Justin Donald: So, for listeners that struggle to network authentically or even to network in general, but I think a lot of people they go through the motions, but they don't know how to authentically do it. What would you say are some practical steps that you recommend for building deep relationships? Not just building relationships. Being able to build the depth of relationships, both personally and professionally.

Jayson Gaignard: Yeah. I mean, when it comes to showing up authentically, I think, it's twofold. One is finding yourself in an environment where it's safe to show up authentically, and that is, again, one of the beautiful things you and your curation process, keeping humility at the forefront. I mean, it's very easy to fall into an environment where you're trying to like compete with the next guy as far as who has more revenue. The thing with entrepreneurship, the scoreboard is so clear, right? It's so easy to be revenue, headcount, capital raised, exit money, whatever the case may be. So, it's easy to get into these traps of competition. And when there's ego at play, it's what it is.

So, finding those unique rooms where they filter that out is, number one, like one of the biggest focuses. There's also another element of like your own comfort in your own skin and understanding your own value. I can walk into most rooms at this stage of my life and not feel the need to impress anybody, and like show up authentically. I remember when I was in the, like, YPO, and that kind of stuff, EO. And I remember I'd show up with like a hoodie and everybody else was in business suits, and that's the way I dressed or what have you. And there was once a joke of like, "Oh, he must be the real rich one because he's the one wearing a hoodie or what have you.”

But over time, I've gotten a lot more comfortable that I can be in any room with anyone. And I'm very confident and secure in like my own gifts. I'm not great at a lot of things. I'm crap at most things, but there are a few things that I'm pretty good at, or world-class at. And I also have that appreciation in other people. So, I love hearing what they're great at and that kind of stuff. So, I don't know if that's the answer you want but finding yourself in the right rooms where you don't have to try to joust for like why you're there and position yourself to be something more than you're not, and then again, just getting more comfortable in your own skin. And I think that's also reinforced by finding yourself in the right rooms.

Like, when people come to MMT, the one of the common things I often hear, especially if they've been exposed to other environments, is like I've had three, four conversations and we never even talked about the work that we do. Or I've been talking to this person the whole event, I don't even know anything about their business. And there's one of the people in MMT. He has a business. He has 1,500 employees. He has an enormous company out in Thailand. And I'll sit him next to anybody regardless of the size of the business. And he's just insatiably curious and like asking them questions. He just loves people, and people will never know that like he's arguably like the most successful person in the room.

But just because he shows up with that humility, and he creates a safe space, and this eagerness and curiosity that makes people want to show up authentically. So, I think there are many facets to it, but I could probably pinpoint to those two at least as far as being the most important to me.

Justin Donald: Yeah. There's no doubt that the rooms that you're in influence more than just about anything else because it influences the relationships, it influences your education. Like, I just believe, I mean, why did I work so hard to have the financial abilities I have? It’s so that I could continue to invest in myself, my education, to learn and grow, and to invest in epic experiences with friends and family, and then let's throw health there that I'm able to live a vibrant life, where health is at the forefront, right? So, it's like any extra capital that I have, any extra money, like those are the three things that I want them to go to. But the thing that influenced like if I had to look back and say what has influenced me more than anything else to help me get to the level that I'm at today, I'm very happy where I'm at.

My goal is to be very content, but to still have goals and dreams, and be driven for those. And also, that I know that there are people in my ecosystem that have goals and dreams, and I can help them drive those. But for me, the number one impact, hands down, is peer group. That's it, from an education standpoint, from a relationship standpoint, from an accountability standpoint, from just thinking at a higher level standpoint like mindset. The mindset shifts I have had being around other people playing the game of business and life at a higher level than me, wealth creation, fitness, you name it. Like that right there, that's worth the price of admission all day, every day for me.

Jayson Gaignard: Yeah, I totally agree. And I will just point out, because I do know you enough to say that you're one of the few people that practices what they preach. Like, you live it. I know you surround yourself with great people. You're on the pickleball court with all kinds of fascinating people all the time. So, you're checking two boxes, both your health and your peer group, which is good. That's high leverage, smart move. But no, I mean, it's one of those things, like, when somebody who's very early on in their journey may ask me like a question, like why should I invest in relationships? I don't even know how to put it into words. I'm just like, I'm not here to convince you. Like, do you eventually?

Maybe. And maybe not. But maybe in 10, 15 years, you'll get that glimmer of why, and then come back to me, and I'll tell you how to foster credible relationships with amazing people. But, to me, it's to not focus on relationships and keeping that at the forefront. Maybe not the number one priority because your health, to what you said, is incredibly important. But if it's not in the top two or three, I can't help you. I don't know. It's too big of a chasm for me to try to convince you that relationships are important.

Justin Donald: Well, and I can do all the convincing right now with just, look at any study out there, capturing the thoughts and experiences and commentary of someone on their deathbed. And you'll see the number one regret people have is relationship-based. And the number one wish that they had was relationship-based. It's not money-based, it's not more assets, it's none of these things. It is purely through and through relationships. I wish I would have done that. I'm forever grateful I did do that. To me, that's the greatest proof you ever need because at that point, you'll for sure be wise enough. Hopefully, you can glean that wisdom earlier in life, but at some point, like these are all people that have had much more life than you, you know?

Jayson Gaignard: Well, I mean, there's that saying, "To know the road ahead, ask those coming back.” So, yeah, I mean there's a great book, The Five Regrets of the Dying, and what you're pointing to, I think, is absolutely brilliant. There's also that Harvard study that the longest study in adult development history, which has proven to kind of time and time again that the biggest factor for longevity isn't actual like fitness or diet and all that kind of stuff. Although they contribute in a significant way, it's actually the closeness of your social ties. It doesn't mean you don't have to have a network of 50,000 followers on LinkedIn or any of that kind of stuff. But having a core group of people that you share life with is absolutely kind of critical. So, when you look into the research of what people do regret on their deathbed and in the later stages of their lives, it's almost always relationship stuff. So, that's a beautiful thing to point to.

Justin Donald: Yeah, I love that. And for those of you that you're watching or listening, and you're like, “Hey, I can't afford these groups yet,” I would say find the groups you can't afford. And if you can't afford that, then curate it yourself. I've curated a number of dinners. Jayson, you started out by curating dinners. Just start putting people in a room together, and you don't even have to pay for it. You can, like, it's really cool if you have the means. If you don't, just let people know everyone's going to split it. But don't let that be the thing that holds you back from incredible content and conversation. And if you're unsure what to cover, you can do kind of like a Jeffersonian style, or you could just go to ChatGPT or Grok and just say, "What can I do that would be a great conversation for the table?” So, I just think putting yourself in a place that you have really epic humans around you breathing and speaking life into you is the greatest gift.

Jayson Gaignard: That is. Yeah. Plus one, dude, you're crushing it. Yeah. I mean, the philosophy of if you can't get an invitation to the table, build your own table.

Justin Donald: That's right.

Jayson Gaignard: On some level, that's what I did. I belonged to other organizations, which were great, but I only jived with 5% of the membership. So, for me, I'm like, "Well, I'm just going to try to build my own table.” And fast forward 12 to 14 years, I'm now on your podcast, and I've made it.

Justin Donald: That's way too kind, but I think you made it way before this, and I cannot wait for the event in April. This is going to be awesome. I'm so thrilled. Your event is the longest event that I go to, that I make time for, and I'm thrilled about it. I can't think of any other event that I would be willing to carve out the time to be in attendance for. So, I mean, that's for real.

Jayson Gaignard: Well, I don't take that responsibility lightly. So, right after this call, I'm going to plow right back into designing the event, because we're only 102 days away, but yeah, it's an honor to be in a position of service, to have you in that space because you're such a value add. You know, you live all those core values that you look for at Lifestyle Investor. And you bring that into our room, and again, the quality and event really comes down to the people like you that really carry the culture and that kind of stuff. So, yeah, so just thank you for allowing me to be of service and thank you for allowing me to be on your podcast today.

Justin Donald: Well, thanks for the kind words, and, hey, this was an awesome session. Thanks for bringing your wisdom and sharing your gifts. Where can our audience learn more about you, more about your book that is likely coming out in June? Give us the goods.

Jayson Gaignard: Yeah, I mean, CommunityMade.com is the website for the book. That is the title of the book as well, The Truth About Success and the Relationships that Create It. So, if your focus is on allocating your energy to social capital and building remarkable relationships, I've been lucky enough to stumble my way through that over the last decade, and I've condensed it into a book. Outside of that, MMT is mmt.community is the domain name. So, that's where I spend the bulk of my time if I'm not working on the book. And then outside of that, you can find me on all major social platforms, LinkedIn, Instagram, just using my name, and feel free to reach out. I love connecting with fascinating people. And if you're listening to this podcast, probably pretty fascinating to me. So, please don't be shy.

Justin Donald: I love it. Well, as my highest and best endorsement, I've been part of 30 different mastermind groups over the years. The whole reason I started Lifestyle Investor is because I couldn't find the one that was the right fit for me that had the depth and was all-encompassing. And I started Lifestyle Investor before I ever found MMT. And so, on the short list of masterminds that I'm part of, because like you, I put a ton into Lifestyle Investor, I put a ton into the events and everything that we do, I have a short list of groups that I am part of now, and MMT is one of them that I give my highest endorsement to. So, if you have the opportunity to apply and if you are accepted, it's something I would definitely join.

Jayson Gaignard: Thank you, my friend.

Justin Donald: Yeah. Thanks, Jayson. I love ending the episode with a question to our audience. So, if you're watching this or if you're listening to this, what is one step you can take today to move towards financial freedom and really just move towards living a life that you truly desire on your terms, not a life by default like most people, but a life by design? And what's one thing you can take from Jayson today that can help equip you on that journey? Thanks, and we will catch you next week.