127: Jayson Gaignard Was $250K in Debt. Relationships Helped Him Rebuild

The beautiful thing about relationships is they compound into incredible things. People look at my peer group now and they're like, oh, you know this person or you know that person? And I'm like, I do, but they weren't this person or that person when I met them 10 years ago or 15 years ago. That individual and I have compounded, and their work and their notoriety and their time in the spotlight has compounded as well. So if I reflect back on that event, I probably had a hard time kind of navigating that room, as I can still have challenges. But again, I have systems and processes to help me.

Welcome back. This is From Startup to Grownup. My name is Alisa Cohn, and today I'm thrilled to Jason Gaynor to the podcast. Jason is an entrepreneur and the founder of MMT, an invite-only community for entrepreneurs. He's also the author of a new book called Community Made. Jason and I had a great chat about how he built a successful business and then realized he hated it. He found himself a quarter of a million dollars in debt and searching for what was next. That journey ultimately led him to building MMT and making relationships and community the center of his work. We talked about how he got the idea for building his business around intentional relationships and his strategy of 8 seconds of courage to get yourself to do hard things. We also talked about how to make the most of conferences and large events, including the preparation and follow-up, which most people miss. And we also talked about how to avoid comparison and jealousy when you surround yourself with highly successful people. There are a ton of practical tools here for founders and leaders, so please enjoy my fantastic conversation with With Jason Gaynard. Jason, welcome to the show. I'm so excited you're here.

Not as excited as I am. It is truly an honor. I've known you for many, many years and I've listened to a lot of your episodes. So to now be on camera with you is an opportunity I'm very grateful for.

The spotlight's on you. Well, that's so kind of you to say. And I'm so excited because you're really, in some ways, you're an entrepreneur's entrepreneur, right? That's the way I see you. You're an entrepreneur, you're a community builder, you're an author of the new book. I'm gonna show it right now. Community Made. Community Made, everybody. The Truth About Success and the Relationships That Create It. And this for you like the work of a lifetime. And I think I just want to start because you're an entrepreneur, you know many entrepreneurs, and my observation of entrepreneurs is that very often, especially driven people, are either running towards something or running away from something. And I myself often have the energy of like running away from the things in my past that, you know, I want to like somehow overcome or something. Do you think in your mind's eye, are you running towards something or running away from something that's kind of driven the whole business that you built?

This feels like a coaching session. I like it. I love it. I'm loving this direction. You know, it's a great question. And honestly, James Clear has a saying that the book that changes you isn't the one you read, but the one you write. And this book is somewhat memoir-esque. It's very practical and tactical in nature, but it does have a little bit of a tinge of memoir to it. And I share this because the writing process really forced me to unearth a lot of different things. And specifically, it's not by chance that I found myself in the community building space as a result of a childhood where I felt like I didn't necessarily belong. And being just relationally focused is also as a result of Again, just this isolation I had at a very kind of young age. So these traits have carried me on. And I always said that I stumbled into the relationship space and the community building space. But as I force myself with a little bit of reflection, it is very clear that I'm trying to create, you know, a space for others that I didn't necessarily have for myself. So probably a little bit of both.

Yeah, that's totally beautiful. You know, it's funny that James Clear said that. I think also I would add the sort of the axiom, we teach what we need to learn.

Yeah, that was section 3 of my book.

Yeah.

Yeah, I've referenced section 3 Which is all about how to ask for help because it is such a challenge for me. And yeah, so I think there's truth to what you just shared as well.

Yeah. So Jason, you talked a little bit about your backstory, but let's dive into that right now. I mean, really, you had a very compelling backstory in terms of like how you grew up and in particular sort of your experience a little bit in, let's say, in and out of school. And then your first business collapsed and you were in debt. Give us a little flavor of that so people understand where you're coming from. And then we're gonna talk about what you built.

Yeah. So real quickly, I dropped out of high school. I wasn't much of an academic. I was just waiting for my day that I could kind of leave and lead into some kind of career. I come from a long lineage of physical laborers. So I thought that was going to be my career path, something, you know, whether it be construction or whatever the case may be, I stumbled into being a mechanic and did that for a couple years. And then inevitably, I decided one day to quit and lean into entrepreneurship. And I started a business geared towards running errands for people. So our slogan was, if it was legal, moral, and would save you time, we take care of it. So I do anything and everything for $50 an hour. I broke up with people's girlfriends and Dropped off their stuff. I watered people's trees. I chauffeured people around, and I did that for a handful of years. And when people thought of the word concierge back in the day, they thought oftentimes of hotel concierge. And when they thought of a hotel concierge, they thought of concert tickets. So concert tickets started to become a big part of the business, so much so that we ended up pivoting into an e-commerce business, which became the second largest ticket wholesaler in Canada. And after six seven years doing that, the business was doing great financially. But I realized I built a business I hated to enable me to buy things I didn't need to impress people I didn't like. I take my wife. To concerts and I wouldn't listen to the music. I'd count the seats and be like, oh, I wonder how much revenue they made off this concert. And we sold millions of dollars of hockey tickets and I'd never been to a hockey game. So it was clear that I wasn't necessarily in alignment with the work I was doing. And I had this vision of— I couldn't sell the business because I was so unfortunately integral to it. I didn't build the right systems and didn't have the right people in the right seats. So I became comfortable with the idea of scaling the business down to zero and then finding the, the next thing. Unfortunately, 2 things happened that were beyond my control that landed me a quarter million dollars in cash debt in August of 2012. September 1st, my daughter turned 6 months old, and on September 1st, I got married to my wife. 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 rather tough hallway for me at the time. And I had met a person at an event a year prior who had posted— while I'm just like in the depths of despair and not knowing what I'm going to do with myself— she had a ticket to go see Seth Godin in New York. And I'd never had an opportunity to see Seth in person. I've always been a big fan of his work. And it turns out the theme of the workshop was the connection economy and how there's huge value connecting like-minded individuals. And for me, I just felt very kind of isolated when I got married to my wife. She doesn't like me sharing this, but I had 2 people at my bachelor party. I had my brother and my brother-in-law. I knew nobody. So I had this grand vision of starting these dinners just to be a fly on the wall of these conversations between fascinating entrepreneurs. And on my flight home, I ended up booking a restaurant because I'm like, I'm going to weasel my way out of this idea and all the doubts will start creeping in. So at least I'll book the restaurant and I'll send the first invitation. And ultimately what I did was I went through almost like an Inc. 5000 list of local businesses. And I said, hey, I'm doing a dinner for other folks on this list, if you want to join us. I probably had a 5% response rate at best. But thankfully, I had my 8 guests. And the night of, I almost canceled the dinner 2 hours prior, because I'm like, nobody's gonna see value in this. They're gonna think I completely wasted their time. But I quickly realized that being in proximity of just fascinating people was something I want to do to some capacity for the rest of my life.

Yeah.

And not necessarily as a business, because I was actually paying for these dinners out of pocket, which Which on some level was a little crazy given the financial situation we were in, but I was planning to probably declare bankruptcy. And for me, I just kept on telling myself the bank could take my car, they could take whatever measly assets I had left, but they couldn't take my relationships. So investing in myself and investing in my relationships were really the safest investments I could make. And a couple weeks later, as I was kind of continuing to try to do these dinners, Tim Ferriss was coming out with a book called The 4-Hour Chef.

Yeah.

And I was lucky enough to meet him a year prior, but he was the first big-name author to almost get banned from all retail distribution. Barnes& Noble, Walmart, everybody. And this was a big deal, especially because he was already a well-known author. And the expectation is that every book he does is going to hit New York Times. And if you can't hit retail, you're not going to hit New York Times effectively. So what he did was— and he was the first author I've ever seen do this, but it's a common practice amongst authors now— he created this book bundle campaign that if you bought 50 books, maybe he'd do a webinar, and maybe you get a blender at 100 books, or whatever the case may be. Well, he had this long shot package that if you bought 4,000 books, he'd do 2 speaking engagements. And at the time I thought of a friend of mine who does events and I said, hey, this could be a great opportunity for you. And the minute I clicked send on that email, I said, you know what, this is probably a great opportunity for anyone. So I emailed Tim directly and I said, you know, I'll take the package. Worst case, I could probably sell off the speaking engagements because it was 4,000 books and it came with 2 speaking engagements. Yeah, I had no frame of reference if that was a good deal or not. Turned out to be a great deal. Yeah, actually. And after I pulled the trigger on that, I decided to do an event with Tim and just saw it as a chance for me to do what I do in the dinners, but on a larger scale and was planning to just do the one event. As a project of sorts, because I was spiraling into a dark place. And then we had our first MMT, which was much closer to a wedding than it was a conference, because I was very ignorant as far as how to put on an event. But yeah, it turned out to be something special. So as a result, we decided to do a year 2, and then a year 3. And now we're 13 years in.

Wow, it's so organic the way you talk about it. And there's so much I want to unpack. Like, even just going back to, you know, you're sort of saying you're at these dark moments of your life, like you're just feeling dark, right? So you had a baby that was relying on you, you had a wife you had to support, and you You were feeling like this sort of concierge business was not the business for me, and it just, it didn't feel like the right thing, but it was making a lot of money. I guess I just want to say that, like, actually, I think it's very unusual to decide, I'm just gonna quit, especially because you were not thinking, I'm gonna quit and go into dentistry, like my real life or my real love or anything like that. You were just like, I'm just gonna tail this down. But also, you were in a dark place. It's hard to, like, act as your own agent in those moments. How did you find it in you? To take those actions.

You know, that's a great observation and it's something I sit with. I mean, I think I had a natural trait to cut things off and burn the boats, and that could be for better or for worse. Now, this turned out to be a great story that, you know, I burned the boats of that business and went all in in this, like, to what you said, almost like an abyss. I didn't know what was next, which is very different than being like, okay, I'm gonna jump from this business to that business or this business to that career.

Yeah.

But that was just a natural kind of tendency of mine. At the time, thankfully, it very much kind of worked out. But it was one of those things, if I look back on just how I operate in the world, when I do feel something is out of alignment, I don't want to delay that anymore because I can fast forward into the future. And for me, something that has always been really, really helpful as far as a decision framework is— and I know Jeff Bezos coined the term like a regret minimization framework, where the idea is basically you're on your deathbed and what are some of those regrets that you may have? And as a result, how can you mitigate those regrets? by making the hard decisions, you know, far in advance. So that has always kind of served me. And whenever I feel again out of alignment and there is a clear path, or even if there's not a clear path, but at least clear the path I'm on is not going in a good direction, then I know I have to make a change.

You make a change. And then when you were kind of like, let's say, on the plane, like flying to this event to see Seth Godin— Seth Godin, of course, being, you know, a world-famous marketing expert, and I would say, you know, leadership guru, and I think, you know, sort of Yoda for a lot of people. You were going there. What were you hoping to find? Because a lot of people, I think, are seeking inspiration. But gosh, that's like a big pain to get on a plane and then go someplace and like, what, to sit at the guru's feet? Like, what were you hoping for?

Yeah, it's a good question. If I look back on some key inflection points of my life, you know, oftentimes they were decisions that didn't make complete sense. Like, I couldn't necessarily vocalize that like, this makes sense for me to do, but they're almost like there's this gut intuition And the tug, you know, the buying the 4,000 copies of Tim Ferriss's book and committing to do MMT. And so many moments, again, as I was writing the book, like bringing that stuff to surface, it made me actually just very appreciative for my wife, for her level of support. Because the amount of times I'm come out of the blue and I'm like, hey, I'd like to hop on a flight tomorrow to go support a friend, or I'd like to hop on a flight next week to go meet this person. So yeah, that's just been a kind of a common theme of sorts, and it's inevitably kind of thankfully worked out for me.

Yeah. So it's like some way, whether it's impulsive or your intuition talking to you, it's like you sort of feel into like, this is the next thing for me to do.

Yeah.

It's gonna be good for me.

Yeah. I wish it was something more concrete and tangible. Trust me, if I could break it down to a secret sauce, I would. I'd love to monetize that.

Yeah, I know. Exactly. I think we're all trying to find our own inner voice and it's really hard because is that my really my inner voice or is that just an impulse? Is that like an addiction or like an impulse?

The one thing I'll say about Seth, again, I've always been a fan of his work, but a year prior to that, I went to an event that fundamentally changed the trajectory of my life. And that was an event that Tim Ferriss put on. So I was in that ecommerce business, I was unhappy. And I was a fan of Tim's work, The 4-Hour Workweek really set me on a completely different path. And he posted that he was doing an event in 2011 called Opening the Kimono. And it was geared towards authors who want to become New York Times bestselling authors. And I never had an intention of ever becoming an author, which feels very ironic now that I'm holding a book. But I never had intention of becoming an author, but it was $10,000 to go for 2 days. And I'm like, at $10,000, there's probably gonna be some really interesting people there. And that event fundamentally, again, just shifted the trajectory of my life when it comes to relationships. The people who I met at that event who were quote-unquote not big names at the time, who've gone on to become some of the biggest name authors or biggest people in media and publishing, is absolutely wild. And I just— being in that environment was really eye-opening. So I think that probably planted a little bit of a seed that finding yourself in those type of rooms can just be really, really powerful. So to be in a room with Seth To me, I'm like, there's— I'm sure there's something I'll pick up here. And lo and behold, he gave me an idea that set me on a 10-plus-year journey.

Right. So when you were at that first event, I mean, it's great to say that they then became, you know, big deals in the future, but there they were in the room with you, kind of nobodies at the time. Did you also sort of start building your skills in like how to talk to people in that kind of an environment, or were you always just kind of, I can be gregarious when I want to be?

Well, I appreciate how you're positioning me. I still have challenges oftentimes speaking to people, but I've come up with systems. To kind of support me with that. But no, that initial event specifically that I went to in 2011, I mean, I had never gone to an event or found myself in a space like that ever. So dealt with the debilitating anxiety that can come with that and the imposter syndrome. And, you know, I was coming from an industry that, you know, wasn't well represented in that room. Again, a lot of people were authors and had big followings and those kind of things. So I ended up navigating it in the way that felt most kind of genuine and authentic at the time. And, you know, the beautiful thing about relationships is they compound into incredible things. People look at my peer group now and they're like, oh, you know this person or you know that person. And I'm like, I do, but they weren't this person or that person when I met them 10 years ago or 15 years ago. You know, that individual and I have compounded and their work and their notoriety and their time in the spotlight has compounded as well. So yeah, if I reflect back on that event, I've probably had a hard time kind of navigating that room, as I can still have challenges. But now, again, I have systems and Yeah.

Well, that's very pregnant. We're definitely gonna talk about your systems and processes for sure. But after you left that Seth Godin event, all from the plane on the way home, you're like, okay, I'm gonna do something. It sounds to me like you were like, I get it. So sort of like I have a small, not a big epiphany, but a small epiphany. The epiphany is it's important for me. And also I love the idea of being in the room with smart people, being quote unquote a fly on the wall, but in one way or the other, setting up a context where I can be in the room. And if there isn't something in my head, Home base to do that. You were living in Toronto at the time, right? You live in Toronto now, but I was yeah correct Toronto at the time. Okay, and so here in Toronto, what am I going to do? I know I'll start my own event kind of a thing. So it's like you then invite people and you kind of began to realize there's really some gold in here for me to surround myself with successful people. Is that fair to say?

Yeah, I mean I just remember that first dinner vividly. I've done hundreds since, but I mean I lost track of time and I initially was so worried that once we finished introductions, like how do I initiate? Initiate conversation, like how do I get people to talk and all that kind of stuff, and realize the power of just that container of being amongst companions on the path. Everybody was an entrepreneur, they shared that as a commonality, but all different industries, all different stages, and just hearing them— I mean, I said less than anybody else at that table, I can assure you. In part, that dinner, it wasn't about me, it was about them. But I just saw the power of curation and invitation and welcome and holding that container and what can happen within it that I just knew I wanted to continue to lean into it, but I had, again, no frame as far as what could be possible from a business perspective. Again, I was just really doing these for reasons other than just like they felt great and it felt like I was on the right path.

Yeah, it just felt like, again, you were sort of following your intuition and your instinct to sort of like keep going. So I think it'd be really helpful to talk a little bit about tactics and techniques then, because there's— first of all, you know, you convened your first dinner. I have another friend, John Levy, who convened his first dinner. Yeah. And it was like, I invited Nobel Prize winners and who came was the hairdressers, right? Like, so like it starts, it can sometimes start small. And you also said, I got like a 5% acceptance rate. If people want to begin to kind of curate their own aspirational network and they don't already have companions on the path, they don't have access necessarily, and they're going to kind of resort to, I don't know, I'm going to call an event and like cold email people. What specific suggestions do you have for them?

Yeah, I mean, if you're in a position where you have access to resources, you can buy speed. So going to an event specifically, maybe there is some level of curation, can really condense decades of networking into a few short days. So that is the quickest way to the mountaintop. Not every one of these events you can buy access to. So sometimes you can get creative. If you're in a position where you can be of service and volunteer, that's another vehicle as well. Tim Ferriss, when he moved to Silicon Valley, he volunteered at a local, like, startup event, which inevitably he would just book the speakers and take care of the speakers when they were at the event and that kind of stuff. And he forged a handful of relationships, but one of them was with the gentleman— his name escapes me— from Chicken Soup for the Soul, Jack Canfield, who ended up introducing him to his agent, which then became The 4-Hour Workweek, which then led to his success. So again, you look at somebody like Tim now, you realize, like, he had very kind of humble beginnings. And again, in a position of service. So there's those type of ways if you want to embrace really the power of tapping into spaces and those kind of things. But there's a saying that, you know, instead of waiting for a seat at the table, build your own table. So that's effectively what I did to some degree. I did both the events but also started to curate my own dinners and bring people together. And again, very similar to the spirit of what Seth Godin really shared at that event. That is obviously another vehicle. But I think one of the things I'm trying to embrace more of now, because it's just so, so powerful, is actually just reaching out to people cold who are outside my peer group and sharing my appreciation with them. This is something that I've done— I did a lot early in my career. As my set of relationships have kind of grown, I don't say I've gotten lazy, but I stopped that practice because my social cup is full. But it's something I've started to embrace again, and this has actually really been amplified by my friend Andrew Wilkinson. He owns a company called Tiny, and he's very successful at what he does and all this kind of stuff. But the amount of doors that have opened for him just from cold outreach is absolutely wild. He's a beautiful example of somebody who really, really leans into that, and it's paid kind of dividends. So those are definitely some small ways. But I think also what would be beneficial is, you know, for me, I'm always looking at spotting rising stars. Like, for example, For example, I'm looking for a creative director right now and got a handful of applications. And one of the applications that I got, I was like, I can't hire you for this role, but if I can invest in you, like, I have no doubt you are going to be a shooting star. So, you know, again, if I look back at all those moments in my life where I met people who were striving to be world-class at something and had grit and humility, what they've grown to in 5 years, 10 years, 15 years has truly been amazing. So there is this element of like the long game of relationships as well. So there's a handful of things, but I'll say it feels weird to be interviewed by you, but I like respect you immensely in the context of relationships. So I hope we can turn the camera on you every once in a while. I don't know if you have anything else that you would share in this regards.

Well, I like what you just shared. So your point about going to events where there has been some sort of curation, I think that's so important. And sometimes that curation looks like it's expensive, right? And I, in my earlier days when I was younger, I would be put off by that kind of thing. And now I kind of lean into, oh, if it's expensive, it will only have people who can kind of afford it. And so that means they've like, you know, kind of accumulated some level of success. And so I have leaned more into those kinds of events. But then I also would say that it's also helpful to partner with other people. So finding a friend or a colleague where you have different connections.

Yes.

And saying, let's host a dinner together, and you bring your interesting friends, and I'll bring my interesting friends. And I've done that, especially a lot more lately with our mutual friend Dory Clark, but then other people as well. And what I love about that is it makes you feel less, you know, uncomfortable, like, oh my God, I'm inviting her to this dinner. But you're like, no, I got a partner in crime. But also, kind of by definition, you meet people who are kind of a warm— let's say a warm connection in a way, and that can also kind of grease the skids.

Yeah, I think that's absolutely brilliant. There's a friend of mine— do you know Ramit Sethi?

Of course, yeah.

Yeah, so Ramit and another gentleman, Michael Fisherman, many, many years ago, Probably 8 years ago. For a couple years they did this. They hosted a dinner monthly at one restaurant in New York City, the exact same table. It seated 6 people, and Ramit would invite 2 people and Michael Fishman would invite 2 people. And they did this dinner, and then at the end of the year they did a larger gathering of everybody who was invited at those dinners.

Yeah.

And again, they did it for a couple years, and I went at this alone, uh, when it comes to like hosting dinners and that kind of stuff. But I think it's a great thing to spotlight is you don't need to do it alone. That's the thesis of my entire book, oddly enough. You don't have to do it alone, but here I am. So I think that's a brilliant way is finding somebody who's similar to you, ambitious, relationship-focused, and divide and conquer and do these together, whether that is a dinner or a small event. I think it's brilliant.

Yeah. Thank you very much. And also, I wanna come back to this other thing that you mentioned, which is about how you have your systems to like work inside of large rooms because it's all very well and good to say, like, what comes to my mind actually is a very expensive event that I've attended. multiple times called TED, you know, the TED, the technology conference, whatever you wanna call it. And it's like, actually attracts a lot of very interesting people. Interesting, both accomplished and entrepreneurs and tech people, but also artists and musicians. I mean, really very interesting people. And it's massive. It's really big. And they have these like little name tags and you're like, I don't really know your name. I can't see your name from here. Like, I don't know who you are. And it can be overwhelming and intimidating. I'd love to jam with you about like how you've learned to work a large room because that's something that I've really worked on too.

Yeah.

What is your advice for going to A large gathering and kind of quote unquote working the room?

Yeah, so for me there's an element of like intention, but also like removing expectations. Some may go into an event and be like, hey, I want to connect with 15, 20 people, and that can serve as a good way to stretch yourself. Otherwise you may find yourself in your hotel room when you could be at the mixer or what have you. Truth be told, that can be a challenge that I face. As a rule, if I am going to an event, at a minimum there's no No work planned that duration. I try to show up at least a day before and stay at least a day later. I think the pre and post an event is so, so critical that like you need space to either metabolize and follow up with people and that kind of stuff. And even on the front end to just kind of settle and prepare. I don't know, you and I just mutually attended an event and we were kind of going back and forth as far as how we make the most out of it. So again, I'm very curious to know, you know, how you navigate these things as well. But in an event where— I haven't been to TED, so I don't know what it's like necessarily to navigate an event where there's 1,000, 2,000 people. That is probably—

3,000.

3,000. Yeah, a different beast. I tend to find myself or look for opportunities where I find myself in intimate rooms, whether that's an intimate workshop of 18 people or an event maybe up to 150 people. The larger events— and TED is a little different because from what I understand, this is from an outsider perspective and hearing from friends, there's lots you can do. There's evenings planned, morning activities, all that kind of stuff, which is not the norm. Sometimes when you think of like large conferences with 1,000, 2,000 people in Vegas or what have you, programming may be 9 to 5, which leaves— there's lots of opportunities to like host a morning coffee or a morning workout or schedule a dinner. And I've done those. Like, I'll see if there's a good local restaurant nearby. I could book a table for 8. It's low stakes. And if I meet people at the event, I could be like, hey, I'm hosting a dinner this evening, and then fill up the dinner that way. That is a great way, but in a larger event like TED, my assumption is that there's some kind of Rolodex that's provided in advance. That's always good to consume. Again, when there's 3,000 people, maybe a little challenging, depends how they structure it. But when possible, if there is a Rolodex, I try to consume it. Not— and this I think it's important— when you're reading through the Rolodex, it's easy to be like, oh, I want to connect with this person or that person, and almost like discredit certain people based on their profiles. That is an enormous Like, you need to be able to go into every conversation with curiosity, and you never know who somebody knows or who they may become and all that kind of stuff. And we've all been to those events where, like, you may be talking to somebody and they're looking over your shoulder because somebody popular walked by or what have you. So it's not good politics. But when I am going through a Rolodex, what I'm trying to see is, like, what are some commonalities I may share with this individual? Or if I look them up online, who are some common connections that I may have so that if we do meet, We don't have to stay surface level and be like, hey, World Cup, am I right? Or like talk about the weather. I can actually be like, oh, I stumbled across your profile and I saw you are into baking. Sourdough is a big thing for me in 2018. Now I'm into pizza, whatever the case may be. And like pull those threads of commonality, because when you pull those threads, you move from small talk to something deeper and more meaningful. So I'm just looking for like, how can I pull those threads effectively? And then I'll make notes kind of in advance. And then as I'm navigate the event and I'm having interactions with people, obviously leaning into those conversations, and we could talk about that. But to me, I almost frame it like 40-20-40. 40% of my energy is on the pre, 20% of my energy is during, and 40%— probably you should make it a higher percentage— is on post, because follow-up is such an important feature. I strive to plant a seed of relationships and end every interaction on a high note. And if I can do it by email, if I need to reach out to that person a year from now, 2 years from now, 3 years from now, I can pick up from where that conversation left off even if we haven't stayed in touch. So for me, the, the follow-up is really, really important. And also follow-up works really well because sometimes you'll go through a Rolodex and be like, oh shoot, I didn't meet this person, I didn't connect with them. But then you can say that in an email like, hey, we were both at this event, you know, we didn't cross paths, you look fascinating, or whatever the reason for your outreach. And that can plant a meaningful seed of a relationship as well. So those are some of the things that I do at a high level. But I will just say, for that 20% during the event, I try to lean in, playful out, try to engage in conversation. Don't try to go back to my hotel room. It's very easy sometimes to like label yourself an introvert and use that as— and I'm not saying other people do this, I'll say I do it— to be like, oh, I need to go rest and recharge. No, my intention is to like lean in as much as I can, say Yes to everything I can during that time because it's only a few days.

Yeah, I think that's brilliant. You know, you and I were prepping. You sent me a beautiful voice note before the event saying, oh, here's how I think about it. You know, 20/40— I think you actually said 30/40/30 or something. I was like, okay, the math is quite— yeah, I know, I know. Plus, which it was like, is the math right here? But okay, fine. Either way, you emphasize the point of preparation and then post. You said post, post, post. And this event that we went to together, because of that, you really inspired me to really push myself to do the post because I have no problem being present with people in the room. I'm labeling myself an extrovert, but then after I can either crash or— here's the, my observation about all events. All events are like, we love each other so much. And then you go away and that afterglow fades very, very quickly. If it fades for you, it fades for everybody.

Yeah.

And so the point is to use that afterglow to make sure that you really push yourself to connect, connect, connect after. And that way you have, I mean, by the way, these days it's like email, WhatsApp, text. I mean, all the things which can be challenging. But really pushing yourself to do that, that follow-up. But Jason, I want to ask you another question because a lot of people, whether they're introvert or not, suffer from social anxiety. I myself suffer from social anxiety. You know, I'm hosting a dinner actually on Wednesday night and I'm actually like— by the way, I'm the host of the dinner, guys, just to be clear. I'm the host of the dinner. And also I'm a co-host, but it turned out like I invited everybody because my co-host was like super busy. So that's not a problem. But like, I'm just saying, I literally know every single person coming to this dinner and I'm kind of friends with them. And nonetheless, Nonetheless, I feel my social anxiety. How do you handle social anxiety?

Yeah, so that's a great question. You know, for me, when I picked up my girlfriend who later became my wife for our first date, I had questions prepared. Not on pieces of paper, but I prepared because I didn't want an awkward lull in that conversation. So I share that because I still lean into relationships with some form of preparation, not because I I don't want it to feel rehearsed or any of that kind of stuff, but I really do want to kind of settle in and have things in my back pocket, threads I can pull just to, again, drive something kind of meaningful. So preparation has always been a thing of mine. It can go to the nth degree as well. I know if I'm hosting a dinner, I can prep the day of, or I can start prepping 3 weeks out. And if I start prepping 3 weeks out, I can torture myself for 3 weeks. Yeah, for 20 days, I guess you could say, in the lead-up. So I try to stagger things that like, okay, I'm going to start prepping for this like day of or the night before and those kind of things. So the idea of preparation has helped me kind of tremendously. And I also have enough reps at this point to know that there's this— I remember when we did our first MMT, we started 13 minutes late because I was standing at the back of the room and I had all these individuals in the audience talking to each other, heroes, bestselling authors, just people I look up to. And I'm like, I'm gonna step on stage and I'm gonna Disappoint all these people. I've never spoken in front of a group of people, let alone like, again, heroes. And for me, it took me back to was this idea of when I went skydiving. So I'm terrified of heights. So I came up with this genius idea that if I go skydiving, that'll eliminate my fear of heights. Apparently, that's not how it works. I'm still terrified of heights. But regardless, have you gone skydiving before?

No, God forbid.

Absolutely not. Well, you're skydiving, basically you're taking this airplane up in circles to get to kind of elevation. And then all of a sudden, so you're anxious, what have you, and all of a sudden the door opens and you feel like this wind trying to like suck you out of the plane. And I remember I was terrified, but I remember telling myself 8 seconds of courage can like— is all you need. Like once you're out of this plane, you will figure it out. And the first time I stepped on stage for MMT, it was very similar. I was at the back of the room and I couldn't get on stage. And I just remember telling myself 8 seconds of courage, just get on stage. And once you're on stage, you will figure it out. So it's this balance of like preparation, and then also when the time comes, it's just— it's go time. And that has kind of served me. But as you said, you've navigated this as well, so I'd love to hear if you've navigated it in different ways.

Well, that's very— the 8 seconds of courage is very powerful. By the way, let's all agree that hosting a dinner is actually lower stakes than skydiving, folks. So let's, let's assume that you can probably do that.

I think that's debatable. It's— I think it's debatable.

Yeah, I'm gonna add I'm gonna add a few things to what you said. So first of all, in, especially in large groups, I do all this and I love it, you know, hosting a smaller dinner or, you know, a morning workout or whatever that is. And just being like, hey, everybody who's probably also anxious, come to this thing and it'll be a smaller group. The second thing is finding smaller groups. And usually the conference will, not usually, but sometimes the conference, certainly TED does this, like breaks you into smaller groups. But even if they don't, go early. When you go early to the thing, it's at 3 o'clock, but you show up at 2:55 or or 2:45 or whatever it is, you will have a smaller group because obviously you'll be the first, second, third one there, and you'll be able to talk to people kind of in these smaller groups. The other thing I would add is that find things which are interactive. So the event that we just went to, as we just were mentioning, the one in Victoria, there were 2 talks. One I really wanted to go to about storytelling, but I went to the other one because I knew— in fact, you and I had an interaction there— I knew that the other one was designed to be interactive. And my goal was to meet new people. So like, what's your goal? Your goal is to meet new people. Find context to meet new people. And the last thing I would say is that when you're in a large group and it's all like, oh my God, everyone here knows each other. It's a large group.

Ah!

Find one person and then be like, I'm gonna find the gold nugget in this person. Like, I'm not gonna meet anybody of the people here, but this one person, I'm gonna intend to find our commonalities, To hear their story, to see that they're the most beautiful person in the world. And I genuinely take that on, and that helps me both be interested in them, make their day, have actually a great conversation, and have a contact. And oh, by the way, it builds my confidence.

Brilliant. I wrote these down as notes for my next book. You know, so I actually had the exact same thought when it came to the announcements of those breakouts. I looked at the one on speaking and I was Like, I know this is going to be interactive in nature and it's going to be great from a content perspective for sure, but I'm going to have an opportunity to deepen or connect with 2 or 3 different people most likely. And that was going to be much more powerful to me than sitting listening to a talk, which I can most likely consume in an audiobook or in a podcast. So I love the focus on that and also the spirit of the smaller groups, finding those smaller groups obviously much easier. I mean, we take this We have this principle when it comes to designing MMT where we do dinners the night before the event actually starts, which are highly curated dinners of 6 people with the spirit that if you're coming in and feeling a little anxious and that kind of stuff, you'll be able to leave that dinner feeling like you have wingmen and wingwomen in your corner when you walk into the main conference room on day 1. So the fact that you create that yourself when you go to an event, I think, is brilliant. It's a great observation.

Thank you so much. So everything we're talking about, folks, is like the idea of I think two things: being intentional and strategic. You can be intentional and strategic and still be sincere. That's an important principle. And then the second piece is actually it's hard. It's hard. You know, people think I go such a social butterfly. Oh da da da. No no no no. I grew up a very shy kid, and I'm still like I deal with social anxiety and whatnot. And so I would say my meta skill is that I've learned to be comfortable being uncomfortable. And to tolerate the discomfort. And something you say in your book is, growing pains are temporary, not changing is a weight you'll carry forever. So I know that you're kind of on this path too. Could you maybe riff on that a little bit?

Yeah, 100%. Like, all good things in my life have come from discomfort. That's the truth, is finding those moments of tension. And I can feel it in my body. I'm feeling it right now as I kind of relive these moments and knowing that Every good thing has happened as a result of me persevering through that. So that can almost be used as a signal that like, oh, something important is on the other side of this. I need to kind of push through. But again, I struggle with the social anxiety as well. And it's hilarious to me that like oftentimes the people who are those who build community or bring people together for dinners and that kind of stuff, I understand why people oftentimes will put us on pedestals and be like, oh, you're such a great people person, you're so gregarious, and that kind of stuff. And that may come through as I get more comfortable, you know, and everybody's gelling and all that kind of stuff. But that is not my starting point. It's a bit of an uphill battle, so to speak. But yeah, I think anchoring to the truth that every great thing in my life is as a result of me overcoming and pushing through that discomfort, it's just a good thing.

Yeah, it's a good thing, and it's important to build that muscle. So I'm curious if you could maybe riff about maybe some of the things you're thinking of that, like, every good thing has come out of my own ability to tolerate discomfort and deal with coming out of discomfort. And second is maybe talking about the other side of this. So we've been talking about how do you build relationships and how do you put yourself in the right rooms and how do you, you know, even like host dinners and get uncomfortable. But like, then why? So like, then what happens on the other side? So sort of 2 questions. What are some things that have made you uncomfortable that have been like blossoms for you? And then what specifically around relationships has been so meaningful? Meaningful to you?

Proposing to my wife. I mean, it's endless. There's so many things. I mean, hosting that first dinner— actually, if I scale back, going to that event in 2011 where I did not feel like I was part of that community whatsoever, and that I was kind of buying my way into that room. And even while I was there, it was beautifully designed and nobody was, you know, meant to make you feel any lesser. That's how I kind of carried throughout that. And again, just that single event has been a significant inflection point in my life, to the pushing through the discomfort of hosting the dinners to hosting the first MMT to buying those 4,000 copies of Tim Ferriss's book. So there's just a plethora of things. And then when it comes to the relationship side, I mean, that is even more endless. I mean, as I navigate anything personally or professionally, gosh, I'm just thinking of something right now I'm going through personally, family-wise, that like I have a peer group of people to lean on who've been through something similar to help me navigate. And that's priceless, like absolutely priceless. Like, yes, I can buy access to therapists or specialists or whatever the case may be, but to have somebody who's had firsthand experience and truly a companion on the path and who's there for you and who checks in on you— I mean, it's funny, there was maybe 2 years— no, it was earlier this year in January. I decided to host an event very last minute in Kelowna, British Columbia, and decided to do a dinner on like 2 or 3 days notice. And I reached out to 8 friends. They're all very, very busy entrepreneurs. I thought many of them probably wouldn't even be in town. All eight said yes, and all eight showed up for dinner. And I remember feeling like the wealthiest man alive—that like they were willing to drop everything to show up at this dinner. So there's a bunch of tangible stuff as well that I can point to. I mean, gosh, when we navigated the pandemic, our business went to zero overnight. Over the course of 18 months, our revenue was down 92%. I would not have survived from a business perspective and probably still be here if it wasn't for. The support of friends. I mean, people just showing up in powerful ways, lending us money, giving us money, opening doors. I had one friend connect us with a bank that gave us a million-dollar loan, which made no sense on paper because our finances were absolutely horrible. So every single thing in my life that is good, I can point back to a relationship.

Yeah, that's so beautiful, and it's so true, and it makes you feel tangibly wealthy kind of thing. And then there's also tangible outcomes that come out of it. Yeah. Jason, so what exactly is MMT?

So MMT effectively is an invite-only community for entrepreneurs, generally entrepreneurs who find themselves on their second mountain. So these are individuals who may have had success in a certain arena, and now they're on to what's next. And the format, one could say, of MMT is we have a 3.5-day live experience. We have entrepreneurs that fly in from all over the world, and we— I always say that the essence of our events is great people, great great experiences with beautiful kind of learnings that happen intertwined throughout the event. And then outside of that, we do our best to keep our community connected digitally throughout the year. I had that initial event in 2013, and in the lead-up of that event, I was very, very lucky. We had 4,200 entrepreneurs apply to attend for an event that's capped at 150 people. And that was as a result— I'm no fancy marketing genius by any stretch, but thankfully the speakers actually stepped up up and shared the event on their social feeds and all that kind of stuff, which resulted in people applying. I see.

And was this the first event you had with Tim Ferriss? Correct.

Yeah.

Okay. So like, and Tim shared it on his social or whatever. I mean, you have big name speakers who were draws.

Correct. Yeah. So we originally were called Mastermind Talks because what I was striving to be for that first event was almost a TED Talks for entrepreneurs. And because I didn't have money to pay the speakers because I was broke, as you know, the beginning of my storyline, I I took a page out of the XPRIZE where I created a prize for the best talk as voted by the audience. And that's how I had Tim as that kind of the anchor speaker. But then that's how I got Lewis Howes and Mark Ecko and TED speakers to come compete effectively. And yeah, in the lead-up we had all these people apply and I had to stop myself because I had a hard time figuring out how I was going to curate the room because I belonged to organizations in the past like EO or YPO, which are But they're criteria-based organizations. As long as you're an entrepreneur and EO and your business does X amount of revenue, you're pretty much in. And although these organizations are great, I think you and I have both spent time with people that you like, very successful financially on paper, but I wouldn't necessarily want to go for a walk with this person or share coffee with them on a Sunday morning. And for me, when I was going through the applications, I was struggling really hard with like, what is the specific criteria that we're going to use for curation? And ultimately what I decided on was probably the least scientific way to go about it. When I had an interaction with somebody for a phone call, at the end of the phone call, I'd ask myself, would I want to have dinner with this person? And if the answer was no, I didn't care how successful they were on paper, I wouldn't extend an invitation. And I didn't know if this level of curation would pay off, but it turned out to be one of the things that makes MMT as a space rather unique. And there's a lot of—

You talked to all the 4,000 people on the waitlist?

No. So they submitted a form, like an application. And like, I came up with this— you should know, I announced this event, I think it was February 6th, 2013, and the event was May 22nd, 23rd. That makes no sense. Don't do that. If you ever host an event, don't do that. I actually reached out to an event planning company because I'm like, I don't know what I'm doing, I'll hire somebody. And they said, your event is so soon, like, we don't want to take it on because it's going to make us look bad. So I share that because when the applications came in, those that kind of piqued my interest, because you— I mean, you'll get a bunch of people applying, obviously. So it wasn't, you know, 4,200, like, qualified individuals. But ultimately, those I thought were rather interesting, I'd hop on a call with them. And the event actually didn't sell out in the end. It was close to selling out, but I just— there's only so much time to do these phone calls. But the exploration process we have at MMT and that curation process is one of the things that makes MMT rather unique. And if I could distill the essence of MMT to anything, it used to be just an event where I would often say it's like great people, great food, great experiences in a beautiful setting with learning intertwined throughout the event. Because the best learning doesn't always happen in the conference room. It happens in conversation, happens over yoga, happens over dinner and that kind of stuff. So trying to create a space that delivers on both like content but connection time and space and all that kind of stuff is always this art that we're leaning into year over year. So we have a live experience component to what we do, which is through 3.5 days. Everybody's an entrepreneur. They've all gone through our curation process. And then throughout the year, we do a couple of different things to kind of keep our community together. Because of the intimacy of the group, we cap MMT roughly at 150 people. And because they're worldwide, oftentimes there's not a lot of in-person interaction that takes place throughout the year. So that's one of the, I'll say, the drawbacks of the model. If I could wave a magic wand and have everything, it would be the live experience and a lot of in-person stuff throughout the year. But yeah, you can't have it all.

Yeah, you can't have it all. And so I think that's really powerful. And so really, you know, again, it sort of started as, you just wanna picture that like your path has been in some ways many organic, like I'm gonna try this and try this and sort of ease your way into it. And now you have this business which has a structure as you just called out. You know, you have the live experience, you have the curation of entrepreneurs, you have sort of the mingling of folks in some way, shape, or form online. You also do, let's call them mini events, again, online on Zoom throughout the year, with interesting speakers. So like, this is now— it's got a system, it's got a framework, it's got like a rhythm in some ways. Yeah. And you're the leader, right? You're the figurehead, you're the leader, you have a team. I'm just really curious how you've grown as a leader over the past years in evolving MMT.

You know what I would say? One of the distinctions I made a handful of years ago, which was a really important one for me, was how you run a community of 150 people is exactly how you run a company of the same size. So the importance of having very clear core values— our curation process at MMT is really just a hiring process. Like, it's very, very similar to what you'd apply in your business. And then once you have people within your organization, you either coach them up or coach them out based on their— your core values. So my greatest leadership hasn't happened necessarily from me being an entrepreneur in my own business. It has been more as the curator and the person who holds container for the community. And that has had many, many beautiful moments over the years, and it's had its challenges as well. So how you step up in those moments— I mean, the pandemic was a masterclass, I think, for everybody in positions of leadership, because it's easy to be a leader in the good times. But when, you know, you're navigating something like the pandemic where there's a lot of uncertainty and the ground is shifting below your feet, that's when you really get to see your true colors, one could say, as a leader. And I can reflect on that specifically and how I showed up for the community in ways that I feel truly proud of. I can't say that about a lot areas of my life. So lots of my learnings in leadership have come from running this community for the last 13 years.

So talk more about that. Talk about how the pandemic, you know, sort of tested you, and talk a little bit about like moments that you wouldn't want to do over and moments that you feel like they really were your glowing best, either in the pandemic or throughout the process of building MMT.

Yeah, so when it comes to, you know, I think there's certain things about leadership in those moments where you feel proud proud of oneself and the decisions you made where they may not be out in the open and you may not get publicly rewarded for it. I won't be on the COVID of Forbes for some of these decisions, but—

Yeah.

We were— just to paint a bit of a picture— 2019, we were coming off a very successful event in October. In September of that year, we bought our family home. It was going to be our forever home, 57-acre farm that we were going to, in essence, just make into our sanctuary. I actually started a new business to complement MMG. MMT, oddly enough, in January of 2020, which was designed to be what we do with MMT but on a local community scale. So we were going to build a community in Toronto and one in Denver and one in Austin. So I launched that in January 2020, and then March hits and the new company evaporates overnight because nobody wants to meet up in person. MMT on some level somewhat evaporates overnight as well.

Yeah, because of COVID right? In 10 years from now, when people have forgotten the pandemic, we'll mention March 2020. The time of COVID Yeah.

So people of our generation will never forget 2020. Exactly. March 13th for me specifically. So yes, the COVID pandemic just basically, you know, shut down the world effectively. And our business kind of went to zero as a result. And our event, we had an event lined up for June of 2020, which was already sold out. So we had probably $2 million of like prepaid revenue for this event. And what a lot of people were doing at the time in our industry, whereas they were pivoting to virtual events instead and said, hey, I know you bought, you know, this event. We can't do in-person for obvious reasons, so we're just going to do virtual instead. And I refused to do that. I said, we're going to move the event a full calendar year out, and you can either take a full refund or transfer your spot to next year. Now, I was expecting at the time maybe 20-30% would ask for a full refund because back then in March 2020, people were navigating layoffs. There was so much uncertainty as far as what was on the horizon. Thankfully, every single person decided to transfer their spot. We didn't have a single person take a refund, which was huge. That was an enormous vote of confidence and like just something I'm incredibly kind of grateful for. But I share this because we chose not to do our event virtually and just treat it as the same. Instead, I said, you know, I sold you a live experience. I'm committed to delivering you a live experience whenever that can take place. And that was, you know, almost a $2 million decision, one could say, when we were about to lose our house and all that kind of stuff. So that was one of those moments from a leadership perspective, like, I felt that that was the right thing to do from just integrity. And I still look back at that moment with fond memories because it was effectively the right thing to do. And I could have been more selfish at the time and looked at kind of self-preservation. And then, you know, in spite of what was going on, the pandemic, I doubled down in service. I kept on saying to myself, we're going to go down, we're going to go down in service. And I held like a couple days a week, these webinars on like how to navigate the stimulus response from the Canadian government, the US government, and rent relief and all this kind of stuff. So yeah, it was a very trying time on multiple levels as an entrepreneur, as somebody in a position of leadership. But it's, you know, all these years later, I can look back on it as a fond moment. When it comes to not so great leadership moments of mine, I think one of the biggest ones is, and it's almost a consistent theme, I tend to struggle with hard conversations. I know you're fantastic at this and have frameworks and those kind of things. Now, I wouldn't say fantastic at this, making it sound like you and I have had hard conversations. She's not like that. She is lovely. But no, I'm a people pleaser by nature. I mean, I would people please in my youth to keep the peace. So like, I'm always kind of anchored to that as an operating system. However, when you are are in a position of leadership, you have to make hard decisions. You have to sometimes hurt feelings in service of the company, of the culture, of, in our case, the container. And sometimes those decisions took a little too long, and I wish I could have done them kind of sooner. So especially if you have somebody in your company, or in our case, in our community, that culturally may not be a right fit, but you're having a hard time having that conversation about, you know, removing them or firing them effectively, I can be someone who I'm getting better at it, but it's still, it's still very much a challenge.

Yeah, for all of us, right? If you're leaning into that, I mean, I am good at that in some— I mean, I have frameworks for that, but also I've seen the downside of waiting too long, both for my clients and also for myself. And it's, you know, as they say, it's not like wine doesn't get better with age.

Yeah. And I think that is one of the things that, like, once you do, you regret not making that decision sooner, and then you see the compounding Repercussions within the organization. And finally, you do make the decision, and all of the, like, the headache and the heartache that would have been completely alleviated if you just had the courage in that moment, that 8 seconds of courage to have that hard conversation. So, and then once you, once you feel that, it feels so much easier when you're faced with that decision again to be like, I know what the road ahead looks like, and I can anchor to that pain that it's going to be far more painful than having this hard conversation right now.

Yeah. Totally. Jason, I know, I mean, I could talk to you forever. We're sort of winding our way to closing this, but I have a question that's been on my mind that I'm just really curious about. You do surround yourself with very successful people. As you said, you kind of find people early in some ways and they become successful, but also you cold email people and, you know, they show up and you become friends with them over time. And, you know, now you're at a certain— let's say you're a certain status and that people want to flock to you. luck to you, all successful people. And how do you manage— do you ever experience like comparison envy or jealousy of people who have achieved things? How do you think about that and how do you manage that?

Yeah, jealousy is something I don't experience. The only— and I've been public about this— the only thing I've ever been jealous of is Dean Jackson created a framework called Who Not How, which I think is absolutely a brilliant framework. Dan Sullivan and Ben Hardy and I ended up writing a book on it, but it's so simple in nature but so powerful in practice that I've vocalized that, like, that's the only time I've been jealous of something. But outside of that, I love seeing people win. I mean, once you actually get to truly see people— I guess I'm vividly thinking of a friend specifically right now who, like, outwardly is very successful and deserves every ounce of success in the world. When you understand his origin story, when you understand what he had to overcome to get there, and And that's almost inevitable across the board. I won't say it's an absolute, but it is very, very common. So as a result, I remember even we did an event in 2018 where we did this exercise called Step to the Line. Have you ever heard of the exercise before?

Yeah, you did it again in 20— the last time I was there. Yeah, so Step to the Line, tell everybody what it is.

Yeah, so the idea— and this may not originate with this individual specifically, but it was very powerful when we did it and we brought it into MMT. Used to support a great organization called Defy Ventures, which helps men and women transition out of the prison system into entrepreneurship. And they would bring 40, 50 entrepreneurs into a level 3 maximum security prison to do these coaching days with these individuals who were incarcerated and had like business ideas and that kind of stuff. And it was such a beautiful experience. But one of the things that they did as an activity to get you to bond was they did this step to the line activity where they Basically took a piece of masking tape and put it across the gymnasium, and then they had 2 lines on either side of that. And one side was the volunteers, and the other side was all of those that were incarcerated. And the facilitator would say a statement like, I grew up in a home where I heard, you know, gunshots before the age of 10. And like, all of those who were incarcerated would step to the line. Very few of the volunteers would step to the line. And just going through a sequence of questions like that, you really realize like the privileges that you have, and you really get to see people in a very short period of time. I share this because we applied a very similar activity at our MMT event, and the facilitator who has done these in prison, you know, for many, many years said that she came into that environment almost prejudging people based on their success, not realizing how many had very traumatic, like, upbringings and had to overcome a lot when she was doing that step-to-line activity. So I just share this because, again, And it's hard for me to be jealous of someone when you realize oftentimes that, like, more often than not, there's a lot that went into getting to where they are. And also, success is one of those things it's easy to take full ownership for. I used to have a friend like this who, like, chalked up his success purely as a result of hard work. It would make me so angry because there's obviously lucky breaks and that kind of stuff. And when I look at, like, friends of mine who may be crushing it in one domain and Maybe I'm not crushing it in that same domain. Oftentimes, A, I'm not investing the same amount of energy in that domain, so that's one thing worth noting. But B, I think it's also a function of time. Like right now, maybe it's not my time. Maybe it's 5 years from now, 10 years from now, as long as I stay committed to this path. So I know that's a long-winded answer of talking about jealousy, but I think it's so critical, especially if you are going to be relationally focused, to not get into those relationships feeling like you're competing. And it's tough. When you're in the business world, it's tough because the scoreboard is public. It's how much capital you've raised, it's how many locations you have, what's your headcount, and that kind of stuff. So it's easy to have these externalized kind of scoreboards to kind of point to, but it totally deteriorates the notion of any meaningful relationship if you approach it in a way where you feel like there's this comparison or this competition or even this jealousy. It can just really be a cancer.

Yeah, for sure. Do you have any specific advice If someone is prone to that kind of jealousy or cancer?

You know, that's a great question. I wish I could answer that in a very thoughtful and concise manner. I just reflect back on my own journey. I didn't come out of the womb as like this all-loving Jason Gaynard. There was, you know, jealousy and comparison for a long period of time, and the notion of competition was the fuel that drove me in my earlier years of entrepreneurship. It was a dirty fuel, and it's not something you want to run on forever, but it did serve, you know, a certain kind of phase of my life until I just realized, like, again, it wasn't serving me. And it wasn't just costing me and my own peace and well-being, it was costing relationships as well. And as a result, and getting to know people again intimately and pulling on those threads and seeing their struggles and everything that they had to overcome to get to where they are, it was hard not to change. I don't know if you have any additional kind of feedback there. It's a hard one for me to give, like, very concrete advice As far as how you overcome it. I'm sure there's an expert out there in the world, but I'm not it.

Yeah, well, I think that the things you said are really powerful. And I think what I'm also experiencing from what you said is like kind of the inner healing of finding your own life's work and being on your own path, and the inner healing of sort of expressing yourself in the ways you want to express yourself. And there's a way in which it's like you can then put your eyes on your own paper, if you will, and follow your own path because you know your path is leading you to where you want to be.

Yes, I think that's really wise advice. And again, like, every time I look at something, there's moments where I'll find myself in comparison, and then I will say like, oh, you know, I wish I was as famous as Joe Rogan. Joe Rogan has like 2,400, let's say, podcast interviews. I have zero. Well, there's the problem. And when I get to 2,400 episodes, then I can complain about not being as popular as Joe Rogan. So it's one of those things, getting clear on what that path is for you and being committed and Not being subject to the shiny objects of like, oh, this person's crushing it in this domain because there's opportunity costs. Like if I now deviate to go in that direction, if I stay in my lane and just continue to compound, it's gonna compound into wonderful things. So I think that's sage advice.

Yeah. Beautiful, Jason. Jason, just a couple more questions. What do you wish you had known earlier on your journey?

Oh boy. I think it would be pertaining to health and specifically I know I've been using the word compound a lot in this conversation, but it's very true. You know, the compounding nature of stress and anxiety and where that can lead when not addressed kind of in the moment. I am, for the last 18 months or so, have been navigating those compounding effects, and it's challenging to unwind that at this stage of my life as opposed to if I would have started this journey 20 years ago. You know, as entrepreneurs, there is this culture of the hustle culture and hard driving. And, you know, you don't want to— there's FOMO, you don't want to miss out on anything. And again, this notion of comparison feels like you should have already kind of arrived. And one of the challenges I have is like most of my friends are 10 to 15 years older. So there's also this element of like they're more successful, but then I also take age out of the equation. So I think that is something I wish I was more aware of and took action on earlier, was this notion of balancing off that hard-driving kind of entrepreneur. Because even I was talking to somebody who was in the Navy SEALs, and him just talking about like how their deployments work, he's like, we're not deployed for a year, like we're deployed for an 80 or 90 day window, and then we have 90 days like to rest. And you just think at like the highest level of performance, Olympic athletes and all that kind of stuff, rest is absolutely critical. And I think, yeah, that's a lesson I'm learning now the hard way.

I hear that totally. Health is wealth. And very powerful to also have those insights.

You're a beautiful example of that.

Thank you. Last question, what advice do you have for founders as they embark on their journeys to grow into leaders?

I think no matter what you strive to achieve in life, your success will often be contingent on the relationships that you carry. Proximity is truly power. And if your goal is for financial wealth, then be very conscious about those relationships. If your intention is to be the best father in the world, then like, you know, look at your relationships through that lens and curate kind of accordingly. So similarly, if your focus is on becoming a great leader, study great leaders, find yourself amongst great leaders. I'm reading right now Teddy Roosevelt's biography. Teddy's no longer with us, but to be a fly on the wall of his journey, one could say, and see those hard decisions he made has just through his life has served me as just great inspiration even though I never met him. So there's the mentors that you can surround yourself with and the peers that you can surround yourself with. And there's huge value in that. I think that's the best thing you can do. But there's also, you know, in this time of an abundance of content, you know, vying for your attention, wildfires here and wars going on over there. If you can try to own your focus as much as possible and if leadership is your area of focus, there's lots of great ways to be inspired. There's— I think we're in a leadership crisis. from a political standpoint, even in a business standpoint oftentimes, but there's some great ones out there and do everything you can to immerse yourself with their ways of being.

Beautiful. Jason, thank you so much. What a great discussion. The book is Community Made: The Truth About Success and the Relationships That Create It. Check it out. Go to Amazon and other places to buy this book. Jason, what a fabulous conversation. Thank you so much for joining me.

I appreciate you.

Thanks for listening to From Startup to Grownup. If you like what you heard, give it a review on Apple Podcasts so other people can find it. And if you know of a founder or someone else who is meant to be on this podcast, drop me a line through my website, alisacohn.com.