In short
Jai Howitt reflects on building two $1M+ businesses in his early 20s, then walking away to design a more abundant life focused on connection, fulfillment, and travel. The episode centers on choosing better career/life decisions (where you live, what you work on, who you spend time with), treating failure as learning, and letting go of ego/external validation to invite more money and opportunity.
Guest backgrounds
Jai Howitt is the founder of Art of Mondays, which runs “founder residences” around the world. He previously built an agency and an e-commerce brand; the agency grew from solo to a 13-person team, reaching about $1M/year in 14 months, then nearly collapsed due to payroll/over-spending before becoming profitable again. He also describes a childhood shaped by being one of seven kids, feeling insecure about fitting in (body image, being “second or third”), and being homeschooled during a 2011 RV road trip across the US.
Key claims
“There’s never a failure, mate—only experiences.” Spend more time deciding major life choices than rushing into careers. When you’re chasing, you repel; when you let go, you attract. Pedestals and highlight reels distort reality; “be the most interested in the room.”
Notable examples
Boyd (an inventor/entrepreneur) challenges Jai with “How’s it going to change the world?” Jai’s shark-fishing “failure” moment with his dad; a seminar mentor’s claim that people who lose the most money fail more and learn more; Jai’s agency “identity” office and later letting it go; his “be loud for validation” example that backfired socially.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOThe Importance of Growth and Learning
0:16 to 1:18
Jai discusses the significance of personal growth and choosing paths that serve us.
“Do you like to be that worst in the room or how does that dynamic feel with you?”
Lessons from Boyd
1:18 to 4:10
Jai shares profound insights learned from an eclectic inventor named Boyd.
“A few years ago, you met an old inventor named Boyd.”
Choosing Your Path
4:10 to 6:00
Explores the importance of making conscious decisions about career and life direction.
“and could really impact a lot of people.”
The Cost of a Bad Hire
6:00 to 7:20
Discussion on the significance of careful hiring and its long-term impact.
“more time deciding on these things and then pursuing them.”
Embracing Failure
7:20 to 9:31
Jai emphasizes the value of failure as a learning opportunity in life and business.
“But then we stay in that job for a decade.”
Growing Up in a Big Family
9:31 to 14:02
Jai reflects on his experiences growing up as one of seven children and its impact on him.
“And Dave goes, there's never a failure, mate.”
Seeking Validation and Self-Worth
14:02 to 14:50
Explore the early experiences of seeking validation and self-worth.
“you find other ways to try to seek that validation or that self-worth.”
Navigating School and Sports
14:50 to 17:38
Discussion on fitting in during school and experiences in sports.
“And that made me want to be, I played a lot of sports growing up too.”
Reflections on Bullying and Belonging
17:38 to 19:39
Reflecting on experiences of being picked on and finding acceptance.
“it wasn't full-blown bullying, but it was still like you were picked on a little bit, probably made fun of.”
Family Adventures and Homeschooling
19:39 to 21:39
Discussing the impact of family decisions and road trip experiences.
“and won teacher's income most of our life as well.”
Show all 35 chapters
Teenage Reflections and Life Priorities
21:39 to 23:12
Looking back on teenage priorities and experiences during travel.
“We missed a few in the middle in Alaska and stuff, but we did most of the States, a lot of driving.”
Living a Life of Travel and Reflection
23:12 to 25:46
Exploring the lifestyle of travel and its impact on self-reflection.
“And so it doesn't, it's one of those weird things, is like hindsight's always a beautiful thing.”
Building a Business and Learning from Failures
25:46 to 28:00
Insights into building an agency and learning from early business failures.
“So a lot of it actually, it doesn't matter what I'm doing if I'm alone, but often it's walking.”
Lessons from Rapid Growth and Financial Struggles
28:00 to 29:40
Discover the challenges of scaling a business and the personal impact of financial strain.
“So we grew, you know, zero to a million bucks a year in 14 months, I think it was.”
Transitioning to a Flexible Work Lifestyle
29:40 to 31:20
Learn about embracing flexibility in work and the realization of personal priorities.
“You spoke about this onion and the layers of the onion.”
The Impact of Office Identity on Personal Growth
31:20 to 32:50
Explore how attachment to office identity can affect one's sense of self and business decisions.
“And so I basically said to myself, the next thing, I'm not going to operate in the same way.”
The Burden of Identity and Imposter Syndrome
32:50 to 34:30
Understand the struggle between identity, self-worth, and the challenges of imposter syndrome.
“You said the office space, you loved what it did for you, for your look or something.”
The Burden of Identity and Imposter Syndrome
35:47 to 36:49
Understand the struggle between identity, self-worth, and the challenges of imposter syndrome.
“tape religiously for over three years now, and this may sound dramatic, but it has quite literally changed my life.”
The Burden of Identity and Imposter Syndrome
36:58 to 37:09
Understand the struggle between identity, self-worth, and the challenges of imposter syndrome.
“That's G-R-I-F-F-I-N and you'll get 15 % off your entire order.”
Ego and Personal Growth as a Founder
37:10 to 41:40
Discuss the role of ego in entrepreneurship and the importance of humility and connection.
“Let's get sleeping better and let's get right back to the show.”
Perception vs. Reality in Social Media
41:40 to 42:00
Learn how social media can distort our perceptions of others and ourselves.
“And equally, you might take someone that is doing, you're perceiving them to be doing worse than you.”
Understanding Admiration and Pedestalling
42:00 to 44:59
Learn why we admire others and how pedestalizing can hinder personal growth.
“But we kind of shut it off and create these divides.”
The Balance of Abundance and Letting Go
45:00 to 47:48
Discover the importance of letting go in order to invite abundance into your life.
“and it gives off quite a disgusting smell.”
The Pursuit of External Validation
47:49 to 51:07
Explore how seeking external validation can lead to disappointing outcomes in relationships.
“And then a byproduct is you'll have that life.”
Building for Yourself: A Founder's Journey
51:08 to 53:19
Learn the value of creating projects that resonate personally while meeting market demands.
“Mostly because I really care about progression and learning and I want to push myself constantly.”
Finding Your Purpose Through Action
53:20 to 56:00
Understand how taking action can lead to uncovering your true purpose in life.
“It's like you're trying to put a triangle into a square.”
Pursuing Your Personal Legend
56:00 to 57:43
Discover the importance of pursuing your true purpose and overcoming uncertainty.
“But you may or may not, but you don't truly know.”
Finding Direction in Life
57:43 to 59:08
Learn strategies for moving forward when you feel lost in life.
“Seeing your face light up when we got on this topic was gold.”
The Role of Mentors
59:08 to 1:02:17
Explore how mentors can influence your journey and the qualities to look for.
“Have you used them in your, in your life or has it kind of been a bit more of a solo journey for you?”
The Importance of Relationships
1:02:17 to 1:04:52
Understand how romantic relationships can provide support and grounding in business.
“You've been staying with me for however many days now, like four days or however long.”
Communication in Relationships
1:04:52 to 1:07:16
Examine the need for open communication to maintain relationship health during business challenges.
“I had another answer that I'm just wording.”
Navigating Business and Relationships
1:07:16 to 1:10:07
Discuss how to balance business ambitions with personal relationships without overlap.
“And so that's probably more of just really open communication.”
Navigating Relationships and Business
1:10:07 to 1:13:10
Exploring the parallels between relationships and business decisions, emphasizing the importance of growth without pressure.
“might have happened like that potentially yeah i funny there's a lot of similarities to how i would pursue ideas, which is when you start in one direction, be committed to that path.”
Building a Life You Love
1:13:10 to 1:14:58
Discussing long-term goals and the importance of human connection in a rapidly evolving digital world.
“Obviously, Art of Mondays is the main focus business-wise.”
The Art of Mondays Overview
1:14:58 to 1:17:30
An introduction to Art of Mondays, its mission, and how it connects ambitious individuals through community and networking.
“Karma of course but don't do it for karma, just do it because you want to do it and things progress.”
Transcript
Automatic transcript. May contain errors.0:00How do you invite more money into your life? You've got to be willing to let it go. This is Jai. He built two million dollar businesses in his early 20s and then threw it all away to build a life filled with abundance, not just with money, but more importantly, in connection, fulfillment and lots of travel, which is where Art of Mondays was born. Please welcome to the show, Jai Howitt. Do you like to be that worst in the room or how does that dynamic feel with you? I really care about progression and learning. I want to push myself constantly. Like that's inherent need for growth is kind of this part of my blueprint.
0:30And so if I can see ways to increase the rate of learning, I will seek those out. You can choose to do anything in this world. Why do we spend so much of our lives in careers or pathways that don't serve us? Failure is such a big one that we've been taught to believe is a bad thing. I was fishing with my dad and I like hooked the shark and then the shark got off and I was like, ah, I lost the shark. I failed once again. And dad goes, there's never a failure, mate. There's an experience that stuck with me ever since that point. You met an old inventor named Boyd. He was 79, looked like Einstein and partied harder than anyone my age.
1:03We were showing him these products that we were working on and excited by, like a film camera brand. And he just kind of stopped me as we were talking. And he goes, this is all great, but how's it going to change the world? I got goosebumps talking about it. I remember that moment. I was just like...
1:18A few years ago, you met an old inventor named Boyd. He was 79, looked like Einstein, and partied harder than anyone my age. What did you learn from Boyd? Boyd, what a guy. He's one of the most eclectic men that I've met. and at the time I was dabbling with a couple of different ventures. I had a creative studio agency thing and an e-commerce brand. I was traveling to the States with my co-founder at the time and we'd just done a few weeks hopping around and we landed in LA and he lived in this three-story kind of mansion thing and we found him on Airbnb and basically his daughter runs the account and she would just vet people that came in just to find interesting people to go and stay with him because he liked to meet people and he wanted to talk to people.
2:16And so he asked us a bunch of these random asked questions. We answered them all and they're like, yeah, you can stay. And so we shared this double bed together to stay there. But Boyd, we didn't even see for two days. The first two days, he lived in the house we didn't see. That's social. And eventually we met him and Albert Einstein was the image that came straight away and just started talking about all sorts of out there things just straight off the rip. But something that I really admired about him is that he was what I would really define as an inventor. He'd created the first ever daily planner, like physical book before the internet, that eventually went public and was sold in all the physical stores everywhere.
3:00um and then he invented uh the co-invented the fat gel grip that goes on the pens in you know that you write with in primary school uh and a wine glass that was like had a thumb in print and it was like unbreakable and stuff like that um so he'd studied in like really traditional advertising you know the kind where you'd lock yourself in a room for 14 hours until you come up with some you know slogan for a billboard you know that's that was a sort of traditional advertising and we were showing him these products that we were working on and excited by and we were also talking about doing like a film camera brand and bringing back the film cameras, it was a few years ago and he just kind of stopped me as we were talking and he goes, this is all great, great products but how's it going to change the world?
3:46And I remember in that moment, I got goosebumps talking about it I remember in that moment I was just like, oh yeah I suppose the world doesn't need another blanket or a film camera and that was a seed that was planted and for so long I think I just began this search for finding the thing that, yes, was an incredible business and could create a lot of freedom in my life and the people around me but also really changed the world and could really impact a lot of people. I think, you know, I mean this is right at the start of the conversation, we can get into all the stories but being young and wanting to carve this path of freedom and getting into business young, you kind of, oftentimes it's for selfish purposes at the start.
4:29You know, maybe you want to make money, maybe it's ego. And I think as you develop in your life, in your career, you kind of realize that there's so much more that matters. And it's not just about you. Do you think he taught you more about what meaning actually is or made you think more about, you know, there's the overarching term of thinking bigger, but perhaps it's more about thinking better because, you know, understanding the reasons behind the thing, like saying, is that going to change the world? Come on. Let's fucking create something that changes the world. Did it make you think in a different way what Boyd told you those days you were spending with him?
5:12Yeah. To me it was you can do anything. You can choose to do anything in this world. and so why do we choose to do things that either don't align with us, we don't care about enough, aren't helping people, like why do we spend so much of our lives in careers or pathways that don't serve us? Naval talks a lot about these three decisions in your life are like the most important decisions, where you live, what you work on and who you spend your time with and for so many people, they spend so little time deciding those things. You know, you spend a few weeks deciding what job or career path you might go down, um, and accepting a role, right?
5:53But then you spend 10, 20 years in that. So the, it's, it's not comparable. So he says you should spend a lot more time deciding on these things and then pursuing them. And I think it was more along those lines. It allowed me to connect those dots of like, um, you know, not so much thinking bigger. I love that too, but it was, you get to choose. So why not choose the thing, you know, that you can spend your life on? It's also zooming out enough as well and realizing that the decisions that we're making are actually impacting a lot more of our life than we may think. It's like altering the course and it might only seem like a little bit, but it actually ends up being quite a big altering part of your life.
6:41It changes your life, which is not a bad thing. And, you know, my favorite Steve Jobs quote is you can't connect the dots looking forward. You can only connect them looking backwards. So it's actually not really about where you end up, but recognizing that the decisions that we make now actually do change our life quite a lot. It can make us think, I really like what you said there about how we might spend three weeks looking for the best job and put out our applications and take and review what we've been offered. And then we let three weeks, we kind of, in a sense, rush into getting a job so that we can have a job.
7:21But then we stay in that job for a decade. Surely if you spend three weeks, three months or six months to make sure it's the right thing, knowing this is going to be a decade plus journey that's worthwhile i wonder if it's it should be more one-to-one like how long you're going to spend in that role you should spend deciding on it and stephen butler talks about that with hiring yeah yeah he was saying like he spends six months hiring every every hire takes six months when they do their whole application and they take them through a whole hiring process that takes six months and his thought about it is if i don't spend six months hiring then i will hire someone, train that person.
8:08It may well be probably the wrong hire. Then I have to fire that person. Then I have to rehire again, train again, and then hopefully they're good. Whereas if we just make sure we hire the right person, we know that we're spending the right amount of time hiring, uh, training the right person so that then they're equipped for the role and we don't have to worry about it. And so it's like that. It's kind of like, what's the source thing? Like what's the actual thing that is in the core of the onion? Like let's spend more time on that, not the rest. Yeah. They say the cost of a bad hire is worth 15 times their salary or something like that.
8:48And I love the onion analogy too. The thing I was going to say on like your career and spending time in a certain direction. I think it's probably less about, you know, of course, if you're like, if you want to spend 10 years in a certain career path, you're not going to spend 10 years deciding on that path. I think it's more about the ability to change often, you know, progress often, step up often. And so only spending a year in a certain direction and then stepping into this, and maybe it's only a slight pivot into something else, but the ability to do that regularly, because as you said, the connecting of the dots, it's thousands, hundreds of thousands of micro decisions that led you to be here today sitting in this chair.
9:30Do you think it's having the humility to be able to change as well? So not being like, not letting the ego get in the way of realizing potentially you made a decision or you took a bet and it didn't work and having the humility to actually pivot course correct as opposed to staying stuck in something that's not serving you just basically because of your ego and you don't want people to perceive you as a failure yeah failure is such a big one uh that that we've been taught to believe is a bad thing and uh it reminds me of uh i used to film a bunch of youtube videos when i was like 18 on on cocos when we moved back there and there was this uh i was like vlogging on a gopro and i was fishing with my dad and i like hooked this shark and then the shark got off and and i think uh i was i was filming and i was like ah i lost the shark i failed i I failed once again.
10:26And Dave goes, there's never a failure, mate. There's an experience. And it was like, that stuck with me ever since that point. And I think failure is really talked about a lot, or really should be talked about more, but it's the root of everything. You need to be comfortable doing that because it leads to all the goodness in life. If you weren't willing to fail, you wouldn't change. And I think progression is like a core human trait, brings a lot of fulfillment, at least for me. my experience yeah yeah uh one of my old mentors i remember i was in a seminar in a room it was like a high a high ticket like business event for two days and he had a pre-event survey and we had to fill out like different things about our our position where we're at and one of the questions on the survey was how much money have you lost interesting question right yeah and um and everyone was ticking the boxes it was like it was like under ten thousand dollars under a hundred thousand dollars over a hundred thousand dollars over a million over ten million um and like it was basically in business how much money have you lost and i was so confused about why the question was even there in the first place and then we got there on day one and he pulls up all the results and he goes, people might be wondering why I asked this.
11:51And he said, he pointed up at the ones that have lost the most amount of money. He's like, they're the first people I'd go into business with on that list. He's like, cause they've failed more times. They've learned a lot more. Wow. And it was an interesting thing where he actually pivoted. In business, we can feel bad about, you know, having investors on board or losing money or failing and, you know, things not going to plan. But in reality, when things are going smooth sailing, you're not really looking for the lessons. So you're not really growing. It's masked with a trophy. But when you fail, you're forced to look within, so you actually grow.
12:28And so failing fast is just as important as acting fast. For you, though, like we're talking about this kind of having the humility to be able to change and, you know, have this essence in us that makes us course correct and pivot. You are one of seven and you feel like growing up, you always felt like you had something that you needed to prove. Was this something that you had from such a young age? Talk to me about that feeling and yeah, a bit about younger Jai. Yeah, yeah. So I'm number two of seven kids, same parents, very close with our family. and now we're all kind of spread around the world.
13:11But when we were back together, we'd just be kids again. For me, being number two, it was great because my older sister, she was the one that fucked everything up and tested all the waters and I could just kind of coast. But I totally had a chip on my shoulder and I've spent a lot of time thinking about where that came from. and part of it is like the competitive nature of having to you know fight for food on the table at dinner time right because the food is inevitably going to run out you can't go back for seconds and there's so many people trying to eat um and also just wanting probably craving that attention from our parents you know when there are seven you know kids alike they want to be the the star of the show and so when parents attention is on the youngest kids and you're just kind of there um you find other ways to try to seek that validation or that self-worth.
14:07And so I remember in school, I was the kid that really wanted to fit in, but I also really wanted to be contrarian and against the grain and different to everyone else. I didn't want to just settle for who everyone else was. So I don't know, I never really found my place. I think it took me a long time to find that, and that's why I turned into video games. It was a big part of my life growing up. I was obsessed over video games and it was like my own little world I could transport myself into. And then eventually phased out of that and I guess that turned into the game of life and business and led me down this path.
14:44But yeah, it all stemmed from the big family upbringing, I think. Why did you feel like you were always trying to fit in? What was making you not fit in? Having to try to fit in? if I if I am really honest uh it was probably it's probably body image you know I was a skinny kid I was I was young when I was young I was uh didn't hit puberty till I was like 18 or 19 so I was actually pretty short squeaky high-pitched voice looked like a girl with with long hair so there was probably a bit of like you know I got tees and stuff like that but it wasn't you know it wasn't full-scale bullying or anything like that it was kind of this middle ground where I like just wasn't quite enough.
15:25And that made me want to be, I played a lot of sports growing up too. I was always like second or third. I, uh, in, in class, um, you know, I was fairly academic, but I was usually second or third. And so it was probably this pursuit to try to be the best or be the best in the things that I do that drove me. Um, and I wonder, yeah, reflecting back on if that was, was the core of it. Were you second or third through to ability or was it work ethic? Did you work quite hard during school? Were you trying to work quite hard with sports and all of the things that you were doing? Or was it just so happened to be you always ended up second or third?
16:04That's a good question. Sports, I just like loved. So I just like wanted to actively do it. But I wasn't the kind of kid that was like super disciplined. I was pretty lazy, I think would be a word I was used. I hated studying. I remember my parents were quite strict and they'd sit in front of your desk at home, do your homework two, three hours in the afternoon. And I'd do everything but that. Often at school, same thing. There was a period of time where I was in an accelerated math and science program and it was online. So we had our own separate room and we're on computers and we would just do everything we possibly could to just play games.
16:44And we would block out the teachers. Teachers can see your screen. We'd block out whatever that software was. We'd use VPNs, we'd put peanut butter on there. We thought it was a camera in the room, but it was actually just a motion sensor. We would just do anything we could to just mess around. And I think that disengaged learning stemmed from just doing things I didn't actually want to be doing. And I'm just such a big believer in, you know, if you flunk the English exam, but you crush it in math, then do more math. Like, why would you not lean into your strengths and spend more time there. And the schooling system has brought us up in such a way to make us generalists, to make us conform to a system.
17:26And I think maybe that also leads into some of the passion I have now for alternative education. So it's not so much that it didn't serve me. I think it just opened my eyes to other things, yeah. Let's touch on this little piece you said before about it wasn't full-blown bullying, but it was still like you were picked on a little bit, probably made fun of. It wasn't full-blown bullying, but then you obviously didn't fit in as well. It's this weird in-between period where, because if it's full-blown bullying, you're more called to do something to change, but you probably just were in this middle stage where you're putting up with it, I guess you could say.
18:04Was that quite challenging if you actually just sit and think about it, like feeling like you're left out? Is that quite a challenging thing growing up, going like, why am I different to everyone? yeah i wonder if that's what may be really close on the family side um because obviously there wasn't any of that in in the family and really where the chip on the shoulder probably came from it's like oh i'll show you guys you know i i think there there probably is a part of me growing up and even still today that's like there you go in the back of my head that's like you know i'd love to go back 10 years high school reunion and see what everyone's doing and show them what i'm doing you know and yeah I also try to be aware of that and not let that control me and and try to be every person is equal and and and there's something to learn from everyone but um I don't know it was just something I just dealt with you know you just you just kind of kept moving forwards and um and for me uh it shaped the early kind of high school years by the end of high school, a lot of the, because I was trying to hang out with a popular group of kids and they're all the ones that end up going off the rails, you know, and, um, yeah, yeah.
19:18And so by the end of high school, they either left or moved up the coolest schools or whatever. So it was kind of more, more of a core crew that was, uh, much more settling and accepting and sort of found my, found my groove there. So, um, if I didn't have that, I wonder what would have happened, you know, if I didn't find people that supported me. Another part was my parents were both school teachers and won teacher's income most of our life as well. So we didn't have a lot of money growing up. And part of the drive maybe came from wanting to create a different life for myself too, and they really wanted that for us.
19:59And so they would be at every single personal growth seminar under the sun, Tony Robbins. Everything they could spend any money they had on, they would, which is a really amazing thing for us, but kept us in a state of scarcity too. Like it was a weird, again, in the middle. So yeah, I'm just learning this as I'm talking to you all of these times that we sort of landed in the middle, but just made me want to be the best at something. How old were you when your parents decided to take you out of school, hire an RV, and go road tripping around the US? That was 2011, and I was year eight. And it was the only chance they saw to take the whole family because my older sister was year 10, and then you start getting into upper high school and you don't really want to take kids out of school.
20:51So we lived on a farm out in the countryside in West Australia, and they sold the farm. We'd been there 15 years or something. They sold it and they used that cash to, we moved to the US for six months. We bought a little RV, all 31 feet, but little when you've got nine people inside it. And we just set off on this crazy ass journey around the US. Something my parents really loved was adventure and instilled that in us too. And so we spent, we were homeschooled the whole time. Though most of the time that was just scribbling a few pictures on a piece of paper. and saying, oh, look at all this stuff we're doing.
21:28It was more of like a life experience homeschool, I think.
21:34But yeah, that was lots of stories there. We got to see a lot of the States. We did almost all of them. We missed a few in the middle in Alaska and stuff, but we did most of the States, a lot of driving. And funnily enough, I found myself, I was like, I had an iPod Touch at the time, I was 14, and I used to just stay up until 3am just to message my friends back home who were like 12 hours they just finished school at 3pm and I would sneak into mum and dad's room in the back and turn on the little verizon wi-fi router sneak back into my bunk and just be on my phone until three four in the morning on the ipod and so I I don't regret any of it but I reflect back and I wish I was more present.
22:20I wish I was more involved in that trip as a family. But you were 14. Yeah. Yeah. I think it's, it's an interesting thing. You, your priorities are just completely different. I catch myself doing that too. I kind of look back and go, I wish I did this more. I wish I did this. But then at the same time, I'm like, think about what life was like then. There wasn't much perspective. There wasn't much. You just wanted to play video games and play sport, at least for me, and hang out. And you didn't really have, like, the worries were, for me, were, like, the girls at school. Like, you know, you didn't really have worries.
22:59You didn't have, like, there might be some, like, things you wanted, but really you didn't. At 14, a lot of people don't really have the desire to, they don't have a direction or anything. It's like, I'm not fucking doing it in grade 8. Yeah, yeah, yeah. And so it doesn't, it's one of those weird things, is like hindsight's always a beautiful thing. Do you feel like this, like you obviously do a lot of travel, you go around at the moment you're doing, I mean, even with Art of Mondays, right, you're doing all of these residency houses. What do you call them? Founder houses? Founder residences. Founder residences.
23:35And they're all around the world in these super inspiring, like awesome places. And you'll be one by the lake, one in the snow, wherever, right? and for me whenever I go to those places I find it's very it's they're very inspiring environments are you more so reflecting planning when you're in those things and you're spending time alone are you reflecting on the life that you've lived are you planning are you kind of just trying to soak it all in how's your mind when you're kind of spending that alone time in those little residencies that you've been doing well the residencies themselves are not alone at all There's 10 to 15 people.
24:17Are you talking about when we're on them, but I find time to escape? You find time to yourself. Because like, obviously, when you're doing the residencies and you're with all these people, you're having fun. And if you're running the event as well, you've got like some element there that you have to control. But I'm assuming that in these residencies, you do get some time alone. And you sat there to reflect or to think about life. and you know you write I've noticed you do some you're writing you write some really cool captions on your Instagram so I can tell you're quite a reflective and introspective person when you spend those times alone in inspiring places what typically comes to your mind is it more present stuff is it more reflection of the past or do you like to look forward oh yeah good question all of my life has been future based typically almost never reflecting never go through my camera on look at old stuff like a lot of people do it was it's always and I you know I just told myself maybe it's because the ambition or because the things I want to do or because I'm the chip on the shoulder just wanting to be better and for a long time my greatest fear was unfulfilled potential, you know?
25:25Um, so it's funny, funny you ask that because a lot of my life has been looking a little bit less in the future and more in the now present right now, um, which I'm getting better at. And we do do like offline days and things like that at the residency. So we get more of that. I recharge alone too. So I need it. I need to spend that time. So a lot of it actually, it doesn't matter what I'm doing if I'm alone, but often it's walking. So I'll, uh, love walking, usually listening to something because I get inspiration there as well. Sometimes I'll just write stuff down as a result. I want to write a book one day, just like my own philosophies on life and what I think are true in the world and see if other people resonate with those too.
26:07So just jotting down thoughts and notes, it's in a messy little... My creative mind is all over the place. It doesn't have to be organized. It's just brain dumping stuff. And that's usually the same if I'm journaling too. It's just getting stuff out of my mind and onto paper so I don't have to keep thinking about it. So, yeah. Yeah. You have this, like, life design kind of approach where, you know, you're trying to really optimize your life in a different way. It's not just hustle bustle anymore. I mean, even yourself now, you're literally living on the road, traveling around, exploring different places, don't have, like, a home base.
26:48When did all of that change for you, where you started kind of looking beyond just the hours you were spending on your business and kind of optimizing your life for a more, you know, in a lifestyle way? When I was 20, I started building this agency. I was sort of freelancing content and I wanted to build something bigger than myself. So I settled into West Australia and niched into this, you know, creating ads for brands. and it took off you know like it moved pretty quickly it was a lot of many many months of failures prior to that many say 50 sales calls with unknown every single one and a lot of rejection and failure leading up to that point but when it kind of all converged and made sense it grew quite fast you know we went from just me in my studio apartment to a team of 13 people full-time in-house the warehouse studio that we're working out of two minutes from my house and just making all of it up.
27:46And for me, it was all about learning. It was like, I just wanted to be a more experienced person and human and take that into whatever comes next. And everything you said before, it's easy. When everything is going well, it's easy to get caught up in it. So we grew, you know, zero to a million bucks a year in 14 months, I think it was. First, like serious business, first time serious founder. and I made a lot of mistakes. I wish I had got more guidance, but the biggest one came probably year two or three where we just started bleeding money left, right, and center. We had payroll was way too high, paying our people.
28:31There were several times I had to come up with 15, 20 grand in like three days to make payroll, several times, and that really shapes you as a person, as an operator, and got through those times. You just go back to the drawing board. You reach out to every lead you've ever had, every past client you've ever had and you make it work. But what I missed was I was trying to hold this front. No one in the team knew. My family didn't even know. We were still paying 100 grand a year for this warehouse studio with insurance and all the other costs. and so that year you know we made over a million dollars but we spent 1.2 and that was totally my fault I was the only one responsible for that and what then happened eight ten months too late is I had to let go of staff um you know the warehouse which I held a lot of identity to I really loved that space and what it said about me and had to let go of that um we leaned down and we got profitable again, sort of in that third, fourth year.
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29:35And it became a good business again. You know, I was back in the work, but it was a good business. But my heart wasn't in it. You spoke about this onion and the layers of the onion. And for me, I read The Way of the Superior Man. And in there, there's a chapter that talks about a man's purpose at that point in time is like a layer of an onion. And you peel back the layers, you get closer to your true purpose. And I read that. I was like, brain booster's a layer. You know, I need to shed this thing. I need to move forwards and and that's what then progressed into the next which is a whole nother story you know we could talk about it but um your original question was uh along the lines of being okay with change is that what it was transitioning from hustle bustle full-time work work to having a bit more of a freedom i guess approach to it where you're a bit more flexible with your calendar, with your workload, um, and the lifestyle component of your life.
30:30That's kind of incorporating business into life. I think that was the catalyst because I'd gone from my calendar was rigid, rigidly set out every single day, especially when you've got a bunch of calls and meetings and team and, um, and I hated it. I hated the constraint, at least me personally, it's not the way I could work. and I operated like that for years, you know, and I was in the office oftentimes until late at night and I just thought it's what I had to do to make it work and it probably contributed to a lot of it working but coming out of that, I was like, I don't want to spend my life like that.
31:10I feel like there's either different business models or ways, it's just choice at the end of the day. You can find leverage in many, many ways by hiring people, by automating things, by content and media. And so I basically said to myself, the next thing, I'm not going to operate in the same way. And so when Art of Mondays came onto the scene, it was after several months of travel, no income, just sitting in that space of patience and I'll find the next idea. And burn through all the cash I had, I was kind of getting to that point of like, shoot, I need to do something now. um and but but leaning into that i did it differently now i'm like i'm i'm known in the team as like the dude that doesn't want to take meetings you know i've got one recurring meeting every week with my co-founder evan and that's a really important one and a couple with like direct reports in the team but besides that there's none and so now my time is spent more in creative blocks and i still work hard but mostly because i love the work and we spend a lot of time traveling we've been full-time on the road since uh the start of this year and the previous two years have been sort of six months on the road and just designing life differently i'm just a big advocate for um i don't want to use the word balance because i think that's a commonly pulled thread but just the ability to live a life that you don't want to escape from and it's the reason behind the name art of mondays it's like i believe how you feel on on Mondays, it tells you a lot about how you feel in your life.
32:45And for a lot of people, it's a pretty clear signal, but they ignore it. So, yeah. You said the office space, you loved what it did for you, for your look or something. You're like, I loved letting go of the office and what it did for me. How it made me look, yeah. How it made you look. Yeah. What do you think you were holding on to there and what was this office doing for you, which is leading you to spend six figures a year on it. Yeah, yeah, yeah. The funny thing is we barely actually used it that much because in the summer it got way too hot to even shoot in there. So we had to shoot before 9 a.m.
33:22and after like 6 p.m. in summer. For me, when you have a friend or your family or anyone come by and see it, the first thing they say is like, wow, this is amazing, you know, and you're only, whatever, 21, 22, and it gets to your head, you know, you become, you attach your identity to the thing, even though it's got nothing to do with me. And so whether I liked it or not, and no matter how much I tried to escape it, I knew that it was like a persona online too. I knew it could attract clients and it was a great like marketing tool too. So I was kind of on two sides of it. But it really, it made it really hard to let go off i knew the cost of there i knew we were we're in the raid i knew we're going you know like south quickly but i was like just trying to save it you know trying to hold on because i probably loved the feeling of being recognized being you know that that kid with the with the studio and the basketball hoop and the table tennis and the and the young creative team yeah yeah yeah yeah totally it was like it was finally like i was recognized for for me i was worthy of something, you know, and that Jai in high school or primary school was finally recognized for something.
34:41So did you ever feel leading onto that? Did you ever feel like you're an imposter being like showing up that front, but then feeling a different way? Yeah. All the time. Even still. Yeah. I felt underqualified in so many areas and it kind of actually works to your advantage sometimes this is a really conscious thing I did when I started the agency because I didn't feel worthy of charging whatever it was thousand two thousand dollars a month for content I was like why the fuck would anyone pay me to do that even though I had some skills I probably was talented enough to pull it off but I recognized my ceiling and I was like shoot you know I'm limiting myself I need to push past this.
35:25And so I started, I just went to the extreme. I was like, well, I'm going to charge people eight grand a month then. Just beyond what I even thought was fathomable, which allowed me to detach almost from my own identity. So that was kind of funny. But so yeah, one of our first clients we landed was like eight grand a month retainer. They stayed with us for two years. That was like the backbone of the agency. I've been using nose strips and mouth tape religiously for over three years now, and this may sound dramatic, but it has quite literally changed my life. I have a deviated septum, which means I can't really breathe out of my nose properly.
36:01And for a long time, I would wake up feeling extremely tired. My brain was foggy. I had zero energy. And come to find out, when you're snoring and breathing through your mouth all night, you're not truly allowing your body to rest. Your mouth isn't made for breathing. your noses and we can go without food for weeks. We can go without water for weeks, but we can only go without breathing for minutes. I think it's important that we prioritize breathing correctly. I use Dream Recovery's mouth tape and I also use their brand new Second Wind nasal strips every single day. I apply them just before bed and this nasal strip stays on well throughout the day.
36:41The next day it is 2 p.m. right now and I am still wearing this thing from last night. Right now, if you go to the link in the description or the show notes below or go to dreamrecovery.io and use code GRIFFIN, you can get 15 % off your entire order. That's dreamrecovery.io or go to the link in the description or the show notes below and use code GRIFFIN. That's G-R-I-F-F-I-N and you'll get 15 % off your entire order. Let's get breathing correctly. Let's get sleeping better and let's get right back to the show. We see this like ego piece play a massive role, especially for young founders. Because I was the same.
37:23Like I remember being like, oh yeah, like 18 years old, valued a company,$800 ,000, got investors on board. And it was this piece that, you know, you can get attached to that identity and letting go of that makes you feel like people are going to treat you differently. my realization was was like no one actually gives a fuck like no one cares um it was this realization of you do something cool they'll talk about it for a little bit and then they move on you do something bad they'll talk about it for a little bit and then they move on and the people talking about it are literally only the people that know you and the great thing about that is is no one fucking knows you in the scheme of things.
38:07You might even have 100 ,000 followers, 200 ,000 followers, a million followers. There's 8 billion in the world. No one knows you, mate. You're actually irrelevant. And the thing that teaches me this is when I'm in planes and we're flying over cities and you just see all these lights and every single light is a person or a family using that light so they can see. and you just see thousands of them everywhere you see a building and every light's on and you go every single one of those rooms has at least one person in there and for me it's this like ability to be able to remove myself from any pedestal that i'm creeping up on like let's just get rid of of all of that has ego played a big role for you did you have some sort of like ego death in this sense where you had to transition from that business and leave it behind leave the office space and like was that quite a challenging transition for you yeah uh yeah i'll talk about in a sec i wanted to bring back to what you said about just being on the same playing field as anyone else and you've said this even um before where you know you might have a fan who knows you and has seen your podcast and your and your videos and they you do is they say, hi, I'm Tim.
39:30And you say, hi, I'm Chris, even though you know that they know who you are. So I love that as like an approach and a technique. And I think the more that we can bring that into all areas of our life, because you're right, like some people may know us and recognize us, but in the grand scheme of things, who are we? We're all people. We're all just people. Yeah. And by our experience of someone or our perception of someone, it can change the way that we respect them or treat them but the problem is is is that experience or perception is only what we've seen it's actually not them and the thing with social media and people listening to this podcast you know they might be fans of the show and listen to me for hours every single week and i fucking love all of you guys are listening to this for hours every week and sharing and commenting and telling your friends about it and putting a new story, like leaving reviews, all these things are so amazing.
40:28But the reality is, is what will happen is when you listen to so much of it, you start to value that person more because you've heard so much about them. And so people that you follow online can creep into something like a pedestal, like they are better than me or they are above me, which is not the case. And I was working really closely with a mentor, Jim Fortin. I'm going to interview him over the next month. He changed for my life as a young guy. He taught me that whole B2 have concept. Oh yeah. Yeah. And, and he was, I was doing a, I was on a coaching call with him and, and he was explaining how he's like, no one is better than you.
41:14He's like, like, no one's better than you. Like don't compare someone's highlight reel to your reality. and we can do that quite often we can see what someone's presenting and label that as that hot the whole version of themselves when in reality it's such a small segment of them and then we take their whole highlight reel perceive it as their reality compare it to our reality and then go fuck they're doing so much better than us or they're so much better than us when it's actually not the case. And equally, you might take someone that is doing, you're perceiving them to be doing worse than you.
41:52And you can be like, oh, I'm not going to learn anything from them. They're down there. It's like, well, no, you could probably learn something from someone, everyone. But we kind of shut it off and create these divides. This guy said something to me once that is along those lines. And he said, he just came out to me and he goes who do you admire right now like who what content are you consuming who's the person and at the time i just read green lights by matthew mcconaughey and i was like whoa i like matthew mcconaughey i like his stuff he's like you know the reason that you compare yourself to him or you you admire this person you put them on a pedestal is actually just because you see yourself in them.
42:37You have the potential to be the same as this person. And so when you flip that perception and you realize, and then I'm like, well, yeah, maybe, maybe I'd like to be able to act or be really confident and be seen and be in the spotlight, which is typically something I've reserved myself and more introverted. And it's because I like those qualities and I believe I can be those. And that's why you put someone on a pedestal. Oh, this is fascinating. You, you only pedestal someone that has what you want or that has what you want, you have, or you lack. It's kind of like if there's a missing part of you and you're not in a victim mind, you can admire them or pedestal them because you want that thing kind of envy it.
43:25It's like you, you love that they have that. And I want that. Um, so they, so you can pedestal them in that front because they have something that that you don't have. And the reason you don't have is because it's probably hard to get and then obtained it. So you can like pedestal them in that front. Um, a victim, what they would do is go, they would flip it and go subconsciously. They realize that they, they don't have the thing, but they will trick themselves that that is actually a bad thing. And then they'll project it like that is a bad thing. And so they won't have any desire to probably obtain it because it's quite hard to get.
44:03and they're not willing to do the work. So they'll just, instead of doing that, they can just project it to make themselves feel like they're okay, even though they don't have the thing that they're lacking. But then the pedestalling is like, it's kind of like, I don't think there's value in pedestalling anything because I think from an energy standpoint, it makes things hard to get because things that are on a pedestal are hard to get. um and so if we can remove all of that it's the same with that money conversation we're saying on the walk the other run the other day it was talking about how when you are more willing to get rid of something you're more willing to invite it in it's kind of like in the ebbs and flows money comes and goes and it's the same with when we're chasing anything in life whether that's women whether that's the dream like business that we have the amount of money that we want to make when we are chasing something, people can kind of feel it and it gives off quite a disgusting smell.
45:02It's like when you need that sale, you just need it. The needy salesman, no one likes a figure guy. The best periods of sales always come when you don't need it. And it's also a position in negotiation too. Actually, there was a moment I was at this, call it a conference, it was like a personal expression development thing. and it was actually Alex's one that we saw the other day and one of the questions I had for him at the end was like how do you invite more money into your life? How do I raise this ceiling of what I believe I'm capable of? And he said you've got to be willing to let it go and that really stuck with me too because as you just said it's like the tide comes in and comes out you need to be really willing and abundant enough to let it go out invest in yourself and the things to be able to call it back in the less you hold it so tight, the more that will come in.
45:58So if you want the thing, you've got to be willing to let it go. Yeah. And I wonder if that's true for everything. I wonder what that means specifically, just so I can wrap my head around it. Like if you're, because it sounds cool. I want to unpack it a bit so I can understand it truly. Like if you want the thing, you've got to be willing to let it go. So does that mean that you don't have the thing, you desire it, but you can't attach yourself to the thing? Is it kind of like, I wonder how you actually apply that? Yeah. I think particularly the things that you feel a blockage around, like you feel like there's a ceiling or you find yourself just banging your head against the wall when you try to do a certain thing.
46:45A lot of time that would be money and business. Yeah, limiting beliefs, things like that. um so then it's really relevant because you actually need to you know let release control in order to achieve the thing um yeah i wonder what else that relates to i'm thinking like relationships and stuff like that i wonder if i wonder if there's a space there yeah i feel like there's this this element of uh there's this element of of peace that comes with not feeling like you need anything as well. But yes, you get more in. I like to look at these, some of the things that I get fascinated by is the things we want, we seem to try and do things in the short term to get them.
47:32But the reality is, is when we try and do something to get something in the short term, typically it results in none of it in the long term. And so it's this weird dance where you kind of have to be the person that's on the other side of the thing. So like be the person that you want to be and do that thing. And then a byproduct is you'll have that life. It's that be do have approach. It's the same thing of going like what's a good example? Okay, great example. I have had a problem with external validation over the past five years feeling like I need to validate myself externally and so I'll make most of my decisions based on what other people are going to say or think really common if you're in like the social media world as well yeah yeah and I would say before social media it was probably a problem I'm getting a whole lot better at it, especially working really close with Jim this year.
48:32So probably like, yeah, this year, since the very start of this year, end of last year, I've been a lot better with this. But I want external validation. So what I might do, and so I want external validation and I don't want to be alone. I want to have friends and friend groups because I don't want to get old and not have any friends in my life, right? These are the things that I want, right? And so what I might do to get that is be extra loud in rooms so that I can be center of attention. Because then when I'm center of attention, I'm not alone because people are seeing me. And then I'm also getting validation because I'm sharing something that might be good.
49:15And they're going, oh, wow, that's so cool. So I'm getting external validation. but who likes that guy that's very loud in the middle of it and he um is saying everything about him and not letting not understanding anything about anyone else and i imagine it triggers people because the same thing we talked about before which is maybe they want to be able to be the spotlight and then you're not allowing they see that and be in you yeah so then when they when they leave they're like fuck that guy drained me i didn't even get to share anything so in the pursuit of not wanting to be lonely and wanting to be validated, I overextend myself to the point where I actually don't get validated.
50:00In fact, I repel the people. So then I result in having no friends and I'm not getting validated. However, if I went in there, asked questions, and you'll see this happen all the time, was curious, listened, shared where it was appropriate, it was bubbly, really made them feel heard, they will then leave that conversation and go, fuck, Chris is a nice guy, hey? And then they message and want to hang out more. And when I get the message, I'm getting validated because they're thinking of me. So in the pursuit of trying to, and I hope this makes sense, it's making sense in my mind, but in the pursuit of trying to do something, trying to get an outcome, we are thinking too short term and it's actually resulting in long term, the opposite of what we actually want.
50:51And so being able to be the person that is likable, not trying to be liked is the thing that is an important distinguishment. A nice frame of that is to be the most interested in the room, not the most interesting. yeah that's fascinating how do you go navigating rooms where people are doing say better than you do you feel like that's a space you like being in you're naturally having a founder's home founders homes and things like this yeah you're meeting a lot of awesome founders and stuff do you do you like to be that worse in the room or how does that dynamic feel with you Personally, yes. Mostly because I really care about progression and learning and I want to push myself constantly.
51:40Like there's this inherent need for growth is kind of this part of my blueprint. Not everyone's like that. Everyone has different makeups and that's just something I've learned about myself. And so if I can see ways to increase the rate of learning, I will seek those out. And so that's why I like to be in those rooms. instead of being a big fish in a small pond, be a small fish in a big pond. So I think that probably is a large part of why I'm so aligned with the company that we're building, which is just bringing together such brilliant minds at all stages of their journey too and creating a space for them to belong.
52:17It's effectively creating a space for myself to belong and to just live in this creation and ideas and being curious. And, um, so now I'm a really big believer in almost building for yourself, being your own customer. Uh, but it took me 10 years to figure that out, you know? Yeah. That's interesting though, because a lot of people would say against that, like stop trying to build for yourself because no one actually cares about what you care about. I, I would have different advice if you're a first time founder versus like a more seasoned one, because first time founders are inclined to miss that.
52:53That's probably the space, you know, me a little bit younger where the ego would get in the way and I would go down this path thinking people want it but actually no one fucking wants the thing. You just, you know, you think they do. So, yes, you do need to let the market tell you what they want but building for yourself, assuming it's something people want and that's been validated and proven, then you can go all in on that because, you know, it's going to feel like play and not work and it's going to be easy to do, yeah, consistently, authentic. Yeah. Do you feel like that allows you to... build this life by design in a sense where you've got a bit more flexibility and freedom with your calendar and what you're doing by by virtue of doing the thing that you is for you in a sense you are able to build a life by design that serves you a lot better totally yeah yeah yeah yeah i i see that and i i really like that we were talking about it on the on the drive to the gym about calendars and like trying to force something.
53:54It's like you're trying to put a triangle into a square. Sometimes we try and do something because that's the right thing to do, but it doesn't serve us. And I like this idea of being able to create something around you and your life and that serves you. Do you feel like there's this element of like purpose that comes into play here? Do you think that purpose can be quite a fluff term that is thrown around? Do you think it actually is something that serves you? And is it something that you've gone and searched and unpacked? Oh, that's a tough one because, I mean, we grew up in this era of start with why and, you know, you find your icky guy and find your purpose.
54:38And I believe in all of these things, I think, when you can find the intersection. But often it's hard to fabricate. It's hard to just sit down and be like, oh, yes, this, then this. I should do this. That's really hard to do. So actually just by starting and doing something and progressing forwards in some area and then trying something else and then trying something else then leads you to the point where you have enough awareness, enough experience and you can find the thing. So that was my path. That's probably all I can speak to. But I think having it there, you always know. If something isn't right, if there's somebody in your team that's underperforming and you need to fire them, you always know.
55:15There's this intuition. there's this gut feeling we're just not willing to face it and so um i would just go out on this journey try a bunch of shit see if you like it try you know stick with it long enough to to really give it a crack and then you know moving to the next thing it's it's this thing around like you don't know what to do like let's figure out what you don't like to do yeah let's just try and do a bunch of stuff uh this ties really well i a line that i read in the alchemist the other day i'm gonna find it on my phone here great book um i read this i read this page in the book here we go and it said this line it just fucking blew my mind and i was trying to conceptualize it a bit but it says the closer one gets to realizing his personal legend the more that personal legend becomes his true reason for being the closer one gets to realizing his personal legend the more that personal legend becomes his true reason for being i elaborated on i believe in my notes somewhere i said this hits me while reading the alchemist when you i haven't read this and pre-read this let's hope it makes sense when you first start out you may or may not know what your purpose is.
56:37Paulo refers to it as personal legend. But you may or may not, but you don't truly know. Frankly, it's just a dream, an idea, a buzzword, a cool concept. You're not truly embodying that purpose until you start getting closer to it. And when you get closer, clearer, and more certain on it, it doesn't become just an idea anymore. It becomes your life. You make all of your decisions around it. Your life's meaning evolves around it. It's one sole mission on this earth to find, and you won't find it by doing nothing. You need to go through enough uncertainty and challenge for it to be certain and clear.
57:13Such a common DM I get is I feel lost and I don't know what to do. What I can tell you for certain is that doing nothing is only going to get you further away from finding what that thing is for you. Just do something, anything, because what's the point otherwise? Life is made for living, not just surviving. The more I progress towards my personal legend, the clearer and more profound it becomes. Things start to make sense. Life starts to get exciting. And for that, I say, let's fucking go. Oh, dude. Seeing your face light up when we got on this topic was gold. Well, purpose is like a bit of a fluff word.
57:51Yeah. It doesn't hold any weight, I don't think. But when you feel something, like you fucking know. and so like the more you get closer to it the more crystal clear it gets and that's where it gets exciting i think it can be hard though when you just don't know what to do like you're just lost you just don't have a clue like that's the starting piece though you just have to move in a direction and yes you know the direction you move is pretty important as we talked about before like what you do really matters but if you actually are starting from ground zero nothing like fucking lost, just move in a direction.
58:29And I love, I used to look for reference points. So I'm not like trying to do this thing that no one's ever done before, because it's like, well, now you're really floundering. But find someone who's done the thing you're trying to do, someone you admire, someone. And I know we talked about, even though there's admiration, they're still on the same page, but that's kind of the point. Like go find that person that you want to be like and believe you can be like and move in that direction and let them be the guiding light and find an idea related to that. It'll just, it'll put you in the right path.
58:58Yeah. What do you think about mentors and people, um, that, you know, maybe have walked the path you're trying to walk? Do you think they're quite profound and powerful for you? Have you used them in your, in your life or has it kind of been a bit more of a solo journey for you? Largely solo. Uh, the mentorship has usually been more tactical. Like if there's a, uh, problem I'm trying to solve, huge shortcut. like if you can go and pay someone for their time and you know save yourself six months of moving you know trying the wrong thing and they've already tried it and told you no that didn't really work of course still make your own decisions but we've done that a handful of times it's been really impactful um and arguably the self-learning has taken me longer to come to certain certain decisions so i think the important thing is just learning from the right people being really critical of the people you learn from.
59:50When I listen to podcasts and stuff, often I find it really hard to listen to people until I know more about them. And not just from a credibility standpoint, but I want to know they have a life that I also would like to live. I don't want to take, I don't want to consume content from people that I wouldn't trade places with. Yeah, that makes sense. And I guess for me, I would agree with that. I think coach and mentor are two different things um i see mentor is more holistic like i want a mentor that has a life i want to live and this is something i still haven't found i i i don't one of my biggest goals for 2025 is find a proper mentor when i look at that as a bit more holistic like like i see a coach be someone that can help me with a specific thing like if someone's really good at business but he's like fat he can't be a mentor priorities fundamentally are very not aligned with what i'm trying to do in fact i don't i struggle to even listen to anything that they're saying but if he's really really good at business he can help me out in business but he's not a mentor yeah i don't look up to him i think his priorities are very off but a mentor for me is someone that has, he's thrived in the areas I want to thrive in.
1:01:17He's thrived in business. He's fit and healthy. He's got a loving partner. The way his wife looks at him is a great indicator on that too. Yeah, who he is. You can tell when the people I've met in my life where their partner just looks at them in awe, that is a massive desire for me. Like I want my partner to just properly love me and people around us can see that. It's not fabricated. It's not fake. It's real. And I look at these areas and I just go, like that will encompass a lot more. When the kids come up and they're running up to him and they're cracking jokes and they've got character about him, you can tell.
1:02:04You can tell a lot about a man with their kids. I can totally imagine you like finding the person that could be a mentor and asking to go to the house and then just like studying the way they interact with wife and kids. I think it's cool. It's a good indicator. I want to touch on this partner piece. You've been staying with me for however many days now, like four days or however long. And you're with your partner and it's so cool just watching. You know, sometimes I'll like just drift away and just like let you guys do your thing. And it's really, really cool. And I can just see this really awesome dynamic going on.
1:02:43How important has relationships been on this journey, having, you know, a romantic partner in your life throughout this business journey and just growing up in general? Thank you for saying that. Yeah, Alina's awesome. I hope she looks at me in the way that you just described, you know, in awe, and I do the same with her, the way that she holds space and moves through life with so much grace as well.
1:03:10I've seen both sides of this because for a lot of my life, I've felt like I can move faster alone and go further alone or people can't keep up, you know, for example, just because of the rate of change that I want to move at. And so a partner can actually be very grounding and they're the ones that pull you back into presence rather than the future as we talked about before. And so that's something I've really valued in our relationship and also just so many similarities in the things we like and so we can jam out over that. She's had a really incredible journey over the last year and a half going from studying medicine to quitting uni and just picking up a camera and now being full-time in the creative field, supporting herself.
1:03:54So that has also been really amazing to watch and be a part of. And so we can kind of go back and forth on that stuff. And I think that brings a lot of fulfillment in the process too, because not everything is just business as much as people in business feel like it is. And it may be the first priority for a lot of men. But the relationship then, it creates this other space. It creates this, again, I'm coming back to the word balance. I'm going to use it. But it really does, right? Like it allows you, especially when you're traveling too, it allows you to change your state and lean into other areas and it makes it sustainable, I think is the point there.
1:04:31So yeah, constantly learning and evolving too. I think being a great partner is its own skill set that you need to lean into and teach yourself. And admittedly, it's an area that I want to work a lot more on. I suppose it's the short answer there. So I hope that answered your question. have you found it hard to navigate because there can be so much challenge in business and have you have you struggled or has it been an interesting thing navigating that making sure that they can be separate and it doesn't bleed out into your relationship yeah totally yeah the obvious thing there is like the inability to switch off sometimes sometimes you're in work mode and your mind's full of stuff and then being present with your partner.
1:05:26I had another answer that I'm just wording.
1:05:37Can you frame it in a different way for me? Yeah. Just the making sure that your business doesn't bleed into the relationship is quite hard. I just find that it can be this balance. Where I'm trying to get at with this is it's this dance. There's this discussion in the traditional media landscape and in society that men should be more open and vulnerable and honest with their partners. And I'm not sure if I entirely agree when it comes to high operating men that are potentially putting out fires or trying to make world changing things and really make proper impact. It's not a smooth sailing journey.
1:06:22And I also don't think that we need to onboard those challenges, maybe not all of them at least, onto our partner and make them aware of it all. And so I'm just wondering how this dance is between challenge in business, trying to achieve so much great, and how much of that bleeds into the relationship or are you trying to make it separate, etc.? And for me personally, and not everyone's like this, but I separate the two in the sense that I don't do business with romantic partners. That's kind of been just a rule that I, a line I drew for myself. But that's not to say you wouldn't help each other out of love and out of wanting to give and help your partner achieve their dreams and vice versa.
1:07:11There's crossover in that sense, but it's never in a transactional way. It's never in a business partnership. for me personally that's worked because then the relationship can be its its own thing you know and you can give that its own attention and and i think that polarity has been helpful for me um and in the in the tone of like your right business is so fluid and dynamic and challenges fires on one day and ease on other days. And so that's probably more of just really open communication. Like they have to understand and that expectation really has to be set from the start. I think it's almost harder if you've been with someone for several, you know, so many years before you start in the world of business and then they have to see you change and that makes it really hard to change with you.
1:08:01Yeah. So I've been fortunate. I mean, we've been together a couple of years, but I was already on this journey, so I was just really honest from day one with the things that I'm doing in my life and what I need as well and where I can give, and she did the same thing. So, yeah, the answer there is communication, totally, and honesty, yeah. Was most of your business journey, or at least you're 27 now, was most of your 20s, were you single or were you in relationships? Most of it in relationships. I've had three long-term, one in high school, one for majority, like the first chunk of building things.
1:08:40And then that was like a year and a half period, which is also great because there's a lot of growth. You just like throw yourself in the deep end and learn a lot. And then, you know, the last couple of years has been in a relationship too. So I guess I've seen both sides, advantages to both. But it's a hell of a lot of fun when you have someone that you can, you know, by your side that you can jam out with. and enjoy the process together. Yeah, I think it's the pinnacle. I just look at it and I just go like, that's just so cool. I think the more I'm making more money and doing better in business, I guess you could say, it's a weird thing where I just go like, what means more?
1:09:23Like what actually means more? Is it making an extra 100 grand a month or is it making a close partner to share all of this with it's like it's like fuck like that's that's the shit but then it's like finding the right person is that whole battle where you're in this dance of just going like artists don't want to spend time on if they if they don't feel like the right one and so you just go like where this dance of like do you do you lean in to like put yourself out there and and like go on all these dates and all this stuff or do you just focus on you and do your thing and then they'll just pop up in your life like i'm assuming it might have happened like that potentially yeah i funny there's a lot of similarities to how i would pursue ideas, which is when you start in one direction, be committed to that path.
1:10:23And, um, and it must tick the boxes for something you can do for a very long time. Or in the case of relationship, you know, if you do find yourself being attracted to someone, make sure they tick all your boxes. Don't settle for anything less than that. And then just see where it takes you. You know, there's so much, um, I don't know if it's society or culture or there's like, you have to know exactly, you know, you have to know if you're going to marry this person, you have to know if you're going to be with them for the rest of your life. And for me, I think having that expectation creates like this kind of head-to-head force sometimes.
1:11:00So that of course is the end goal, but without the expectation of it. And you can grow together. What's your take? Yeah. I struggle. I normally sit in that first lens. It's a fucking waste of time. But in the sense of like, what if you pursue a business that is a waste of time, but the learning and experience that you got from it and you enjoy the process too, created, crafted you as a person. Yeah, it definitely crafts, but there's an emotional piece to a relationship that you can be more logical in business. True, yeah. I would much prefer to go through logical pain than emotional pain. Yeah.
1:11:44It's a big, it's a big, it's a big, I feel it though. I know what you mean. I think, um, it's such a big thing. You're like, you're like, I will stop every, I like just stop. I'll like, like if I just think I would, I think it's more important. And so I actually think it's a bigger decision. How much pressure do you then put on yourself to find the one? Well, I don't put any, because they have to be. Well, I don't put any pressure in it. I just like, I don't put any pressure on it and I'm not looking. Yeah. I'm definitely not looking, but I envy it. I'm inspired by it when I see it. I'm like, fuck, that's just so cool.
1:12:29Like, I'm like, I just go like, well, at the end of the day, what's the point without it? I don't know. It's just like, yeah, I think it's fucking awesome. So, yeah, I think it's. But that's the difference, right? I agree with your, like, what's the point of pursuing? If you know for sure it's not going to be, you know, then don't pursue it. I agree with that. But if there's a potential for it and they tick the boxes and you can and you will and you're willing to, then it's a beautiful thing because you can grow together. And so, yeah, there needs to be that filter. There needs to be that lens.
1:13:03But there doesn't need to be the hard stop expectation, if that makes sense. I get it. Yeah. What do you think is next for you, though? Obviously, Art of Mondays is the main focus business-wise. You're nomading at the moment, traveling all around the world. What's life look like for you? What are you trying to do in the business and life? And what does kind of closing out the rest of the year look like for you? For me, I believe there's two narratives in the world that I really care about. One is that there's going to be more people building things for themselves, wanting to create freedom in their own lives, whether that's a business or just monetizing something they care about.
1:13:45And two, the world's going more online, technology, AI, like it's advancing so rapidly. That in-person core human connection is just so important. You know, taking it back to ancestral time, sitting around the campfire with your community, right? And so they're the two big bets that I'm making. And I believe we can influence culture and breed this new wave of thinkers and entrepreneurs who want to build lives that they love. And that's the game that I'm playing, so that's a really long game. It's not the rest of this year. That's 10, 20, 30, 50 years. But I can follow different curiosities within that.
1:14:24And so it involves a lot of travel just because I like doing it. I get inspiration from outside myself. That's why we do it. We get to meet a lot of folks. Our communities are all worldwide as well. So we get to drop in and meet people too. and I just want to keep following that curiosity I think and see where it leads me and just focus on the process because I think if you focus on creating value in the world and actually really just helping people and with no expectation of anything in return, it's like this ripple effect and greater things happen. Karma of course but don't do it for karma, just do it because you want to do it and things progress.
1:15:03So that's the space I'm playing in and want to make more content share that with the world I want to have more interesting conversations I want to be more curious uh and uh that about sums me up I think that's awesome and if people would get involved and check you out what what's kind of we we obviously didn't talk about art of mondays and what it is specifically but if you give us a bit of a rundown on what art of mondays is the founder sports club what what all the pillars are and if people were interested that how that how they could get involved with things yeah the short way of describing it is we create spaces for curious and ambitious people to belong so we do that in a few different ways we have like a founder sports club so people uh will introduce you to three other founders in your city every month to go play sports with it's like a new way to network something i'm passionate about how many people do you have around the world?
1:16:00We have 5 ,000 on the paid membership now and we're in 150 cities and that's really rapidly sort of growing. And then going a layer deeper, we have what we call a sort of private community and that's really highly vetted group, curated group of lifestyle founders and who want to go deeper, you know, want to spend time in rooms and spaces with others just like them because I think it's a lonely game business oftentimes it is I'm sure you felt that too and so within that we do a bunch of stuff we have like co-living houses we're doing about one a month at the moment we'll probably do two a month next year at the rate of growth and online spaces and calls and just ways to connect with other like-minded humans and and get more out of this this thing we call life so it's kind of a it's funny I thought so many people would come in for like the really tactical business side like oh yes I can learn from people who've done the thing I'm trying to do I can move faster I could potentially make more money as well um but actually it's so much more about just finding your friends and your people and that's why people stick around so um that's what we have right now and um yeah I'm just thinking off the rip here I've never actually really publicly shared uh the art of mondays stuff but we can whip up a landing page with the art of mondays.com forward slash chris and and take care of your audience because I think there's a lot of synergy.
1:17:23Like I loved what you're building here at the podcast. And if anyone does want to get involved, we can help them out that way. Awesome. I'll leave all of your, your details in the show notes description below. I just want to commend you. I feel like, you know, we connected a couple of years ago now, whenever it was, and then we met up in person last year. It was, it's already just however, however it was in, in barely heads. and I think there's something about you that you have this really calm nature and I really respect it. There's something about an energy where you can be really calm but also switched on and I just love it.
1:18:03You can spend so much time, it's easy and it's really inspiring. So thank you for being who you are. Thank you for sharing your light and your story and I really appreciate it. Thanks, dude. I'm really grateful to be here and spend some time in your world too, you know, living with you for a few days and getting to do this and be out here in Austin. So it's awesome. So good. Screenshot this, guys, if you made it to the end and tag Jai. And we found out that Americans aren't called Jai and they don't actually know. Yeah, they all call me Jai. Everyone doesn't. J-A-I. J-I. Jai. I'll leave all of Jai's details in the show notes in the description below as well as artofmondays.com forward slash Chris.
1:18:44Chris, yeah. And you guys can check that out for yourself. Definitely go and check it out. It's honestly awesome. Founder Sports Club. There's like, well, you said 150 cities. It's like, it's a bargain. It's cheap. And it's, but it's like so, so good. Cause you can literally connect with other founders, people crushing it, doing similar things to you in your city. So you can feel a little less alone when you're trying to do stuff that's for you, not for everyone else. Please just sell first and try out Art of Mondays today. Actually, we've got an app dropping in like a couple of weeks, so that's going to be really fun too.
1:19:17Oh, it does. By the time this pod comes out, I don't know. Yeah, awesome. Sounds good. Thank you guys so much. Leave us a five-star review on Spotify or Apple. It'll help the show grow, help us keep getting awesome people just like Jai back on the show we're going to sign out for this week. Let's go. Bye-bye, and I'll see you guys next week. See you guys. Star Wars The Mandalorian and Grogu is now streaming on Disney+. What are you waiting for? Hop on. The must-see galactic adventure comes home on Disney+. This is the way. Our only chance is to work together. I like this kid. Always wear your seatbelt.
1:19:54Star Wars The Mandalorian and Grogu. Now streaming on Disney+. Read PG-13.
From the publisher
From building two million-dollar businesses in his early twenties to walking away from it all for a life of freedom and meaning, Jai Howitt’s story is all about letting go of what feeds your ego so you can build what truly matters.
Key Discussion Points:
How growing up as one of seven kids shaped his drive
Building and losing businesses that looked good but felt empty
Letting go of ego and the need for validation
Designing a life you don’t want to escape from
How to fail fast, pivot, and keep moving forward
Follow Jai:
https://www.instagram.com/jai.journeys/
Art Of Mondays - get $500 off your annual membership:
https://www.artofmondays.com/chris
Follow Chris:
https://www.instagram.com/morechrisgriffin/
Timestamps:
00:00 - 04:45 Building million-dollar businesses and burning it all
04:46 - 10:12 The shark story
10:13 - 17:30 Growing up one of seven with something to prove
17:31 - 24:50 Early struggles with validation
24:51 - 32:15 Family road trip
32:16 - 39:40 The warehouse, ego, and identity traps
39:41 - 48:05 Letting go
48:06 - 55:30 Chasing validation
55:31 - 1:07:20 Designing a life you don’t want to escape from
1:07:21 - 1:19:00 Purpose and failing fast
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