The Ryan Hanley Show - He Quit the Best Job in the World. Then Built Something Better. - Jon Brod

Episode Date: February 4, 2026

Start your free trial of Ro.am today: https://ro.am/influencer/ryan-hanleyJon Brod had a job most people would kill for: a marketing executive at the NBA who helped launch the Toronto Raptors. But he gave it all up to become an entrepreneur. In this episode, Jon shares the hard-won lessons from his journey, from the court to the startup world. We discuss how to calculate risk, the power of market positioning, and why the most successful people are the ones willing to be uncomfortable. If you're an entrepreneur or a leader looking to make your mark, this episode is packed with actionable insights and the kind of contrarian thinking that separates the good from the great.Get a demo of the #1 remote office software in the world: https://ro.am/influencer/ryan-hanleyConnect with Jon BrodLinkedIn: https://www.linkedin.com/in/jonbrod/---Spartan philosophy, built in the black-ops lab of business: https://www.findingpeak.comFinding Peak podcast: https://linktr.ee/ryan_hanleyThis show is part of the Unplugged Studios Network — the infrastructure layer for serious creators. 👉 Learn more at https://unpluggedstudios.fm.Our Sponsors:* Click the link http://kalshi.com/r/SB60 or download the Kalshi App and use code SB60 to sign up and trade today!Advertising Inquiries: https://redcircle.com/brandsPrivacy & Opt-Out: https://redcircle.com/privacy

Who are the people that I'm doing this with? People are the biggest determinant of success or failure. It's really not the idea. The idea is sort of like third. The execution of the idea is second, the people that you associate yourself with first because they drive the execution and ultimately the idea changes in the process. I've had the good fortune of like doing these entrepreneurial endeavors with many of the same people over and over. And that has made the calculus easier.

The beauty of the podcast is you just get to talk to so many different people. You know, most of the time when someone comes on the show, they've done something worthy of talking about in some regard. But you've had a pretty expansive and diverse, seemingly diverse career that I think is fairly unique. A lot of times when I'm, you know, researching someone for the show and getting ready to talk to them, most of their experience sits in a couple buckets, you know, or one, one main bucket. You know, even myself, you know, most of my career and most of what, you know, most of my experience, knowledge, beliefs, et cetera, are born out of the work in the insurance industry.

Now, done a little bit in fitness, done a little bit in tech, et cetera, and obviously media. But, you know, that's the core MBA, communication apps, you know, all these different things that you've done. It's a fairly like robust and wide swath of different, you know, and I'm sure there's a through line, but. No, I don't think so, actually. By the way, I used the word swath last night in a text. So I love the fact that you just used it. I was like, that word doesn't get enough love. But here's what's interesting.

So I spend so much of my time thinking about how to communicate my company and how to, like, I don't think about how to communicate my company and how to, like, I don't think about how to communicate myself. self and my journey and my stories. So this is really interesting for me because I just like, I'm actually a little bit nervous, believe it or not. I don't know because I, you know, it's like the imposter's like I can't imagine I have anything worth valuable to tell the audience here. But I'm excited for where this goes. Well, let's let's start there. How can a guy with your experience, your success, the diverse and robust nature of the various projects that you've worked on, companies you've started, the number of exited companies that you have, and the continued success now with Rome, how does a guy like you have any kind of imposter syndrome?

Because I think most people listening, when they look through your resume, would be like, you're either full of shit or... What am I supposed to do if this dude's got imposter syndrome? That's hysterical. You know, look, I have high expectations for the companies I work at and with and for myself. And I feel like, yes, I have had a good, interesting career to date. I've had a bunch of success. I've had some, you know, failures or not as great success as I would like.

And I guess that all leads to sort of, you know, a bit of imposter and a bit of, man, I should be doing better. I could be doing better. I should have done better. So I think that's perhaps where some of that comes from. And I actually think, however you label it, imposter syndrome, fear, whatever. One of the things that I try to teach my kids, and I'm interested in your take on this, We were actually just talking about this with basketball the other day. My son is very talented, but he's not a naturally aggressive kid.

So at his age, even though he can do things that I couldn't even imagine doing at his age, he still, you know, he struggles sometimes. And I asked him one day, like, why, like, I've seen you do things that I want to even know you could do that I think are pretty fantastic for your age. But in the games, you kind of get small, right? And he said, he was honest enough to say that he has fear. And what I thought in that, so we have this conversation about fear. And one of the things that came out, and this is where I'm very much interested in your take is I said, like the fear never goes away, bud.

Like, I think that's the big, I shouldn't say, I think it's a big misunderstanding myth, et cetera, that elite performers, people who've achieved success. that the next time they don't feel fear. They've, like, they've, they've, uh, they've beaten fear down and somehow are victorious over fear. And I said to him, I go, I've done 400 keynotes. I'm just as scared every time I step on stage. Yeah. I just know how to channel it now. So do you think it's, it's like, how do you deal with that personally when you're looking at a new

endeavor, maybe even, you know, taking on Rome now, right? You've had all this success. You're going to take on another startup, right? How do you deal with that fear that inevitably comes up when you're going to take on a big challenge? First of all, what a great relationship you have with your son, that he was comfortable enough to say that. So well done there. But you used the word I was going to use, which is the channeling of the fear, right? Like, I, it's so funny, I would get nervous if I wasn't nervous, right?

because you're supposed to be nervous and that's healthy every time I take the stage or I do a podcast or I do a TV appearance. And so I think that's all right and that's all healthy. And then it's then it's channeling that fear into positivity and some level of confidence. But yes, I discomfort. is what, I believe, what grows us, right? That's where we learn. That's where we challenge. That's where we overcome obstacles and ultimately how we grow.

So I have spent a career putting myself in uncomfortable situations because I want to grow and I want to change. And I want to – by the way, like, mindset is an incredible book by Carol Dweck. and we actually make everybody at Rome read it because, you know, it's, it's your mind, like that's something you need to work on. It's a muscle and you need to be this uncomfortable. You need to have a bit of imposter syndrome. You need to be nervous and that means, you know, and then ultimately good things come of that out of that, even if it, if short-term failure, medium to long-term goodness. Yeah. I was listening to this conversation or was a podcast. Tony Robbins was on Diary of a CEO.

And he talked about these five, I'm just going to say things that everybody needs. And he goes through each one throughout the podcast. But there were two that seemingly are diametrically opposed, that they spent an awful lot of time on. And I found it to be probably the most engaging part of the conversation was this conflict between our need as human beings, like a core need. is for us to have both certainty and uncertainty at the same time. And he really digs in and I won't do justice to the level of expertise and knowledge and thought that he's put into this topic. But I found it to be very intriguing because especially as an entrepreneur,

especially someone who likes to dig into new projects, that balance is, it's really difficult because we all desire, I want to make sure my family's taken care of. I want to make sure I'm taking care of. I want to make sure that if I have a bad day, my life isn't blown up, okay, so I need that certainty. But at the same time for so many of us, you know, particularly high growth, high achievers,

entrepreneurs, entrepreneurs, et cetera, if there isn't some level of uncertainty, we immediately become bored, we become distracted, we actually become oftentimes problems inside of organizations. How when you're looking at a project, again, like Rome or like any of the previous companies that you've been with, how do you calculate the amount of uncertainty versus certainty in that project and whether or not it's worth taking on this risk, especially, and this is kind of where my question goes. I think early on, right, we can take on massive amounts of uncertainty.

We're in our early 20s, late 20s, right? But we start to get into our 40s, our 50s. we've had some success, we have some things to protect. That's a, you know, it's tough to balance taking on that much uncertainty again, et cetera. So how do you deal with that equation? I think you're right that a lot of it has to do with age and, you know, with dependents and with financial obligations. And so everybody has to sort of do their own calculus. for me, you know, I had early success, which was great, and that allowed me to continue to do and take risks and do some, all the things that I've done.

But, you know, how do I assess the risk? I, one is like, how big an opportunity is this, right? Like, TAM total addressable market, but just more generally, is this a big? Let's talk about winning, not just in business, not just in life, but in the arena of, well, just about everything. And if you're like me, you love the thrill of the game. I'm a huge football fan. You know Bill's Mafia runs through my blood, except we're not in the Super Bowl this year. And with the big game coming up, let's just say, to make it interesting, I like to have a little skin in the game.

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or download the Kalshi app today, use code SB60, and start making money by predicting the future. This is the way. Big idea or is this sort of a niche idea? And so that's part of the calculus. Who are the people that I'm doing this with? I always say that people are probably the biggest determinant of success or failure that you surround yourself with.

It's really not the idea. And it's really, the idea is sort of like third. It's the execution of the idea is probably second. And the people that you associate yourself with are probably first because they drive the execution. And ultimately the idea changes in the process. So I think that's all part of my. And I've had the fortune, the good. fortune of like doing these entrepreneurial endeavors with many of the same people over and over. And

that has made the calculus easier. These are known quantities. We know what we're each good at and sort of how the puzzle fits together. We trust each other and we can move quickly because we have a common shared language. So I think that's all, but look, ultimately, you know, you've got to, you have certain things you probably need to do, take care of your family, mortgage, whatever it is, and you, and you need to make sure that these risks are the right risk profile for you, right? Like, everybody has their own risk profile, so I'm not going to prescribe that, but I certainly took huge swings when I was a kid, they turned out well, which allowed me to take, continue to take swings as I now have two children that are high school age and going to college and all of the associated costs

and time that's required for that. Any advice to the entrepreneur who is in their early 40s, late 30s, maybe even a little older, who has maybe played it safe. And I don't mean safe necessarily in a negative guy. So don't take that as a negative. But you've got the question. corporate job, it worked for you, you fit in, you made money. You have had a nice career, but maybe they feel unsatisfied by the fact that they were

never in the driver's seat or they never got to create that idea or they saw around a corner and their corporate entity would never allow them to kind of pull that thread. You know, do you have any advice or guidance or thoughts for that level of entrepreneur, that type of entrepreneur who's maybe in the second phase of their career and is now looking to step out into the entrepreneurial world for the first time? Yeah, you know, go do it. Like, if you were really entrepreneurial, right, and go do it. Because actually, you've built up in the first part of your career, you know, a fallback plan, right?

Like, you've been successful at your job, whatever that is, and whatever size company that was, you can probably go back to that. right and so you've done you've done some of the the the work that the the confidence building work that will allow you to then take take the risk do it it is so damn gratifying again like win lose or draw like you will learn a ton I would probably time box it right if if you've got some financial constraints you know say I'm going to do this for two years I'm comfortable with that I've got enough money saved I know I can go back and land a reasonable job if it doesn't work, but do it. Do it. I mean, like, there's this phrase that someone told me, like, this isn't, this is our one big, beautiful life. This isn't a dress rehearsal. And so if you are going to get to the end of it and regret that you didn't do that, please go do it. Yeah.

I was given this exercise, and I actually wrote about it at Finding Peak. and it's two questions. The first question, because I love thought experiments. I realized a long time ago that my brain is broken in a lot of different ways and the best part about that is

if you feed it the right questions and thought experiments, the shit that comes out of it is really interesting and often not what you would expect. And if you've ever read, if you've never read Untethered Soul

by Michael Singer, a fantastic book, very short, very quick read. And the idea is we are not our mind and we are not our body. We are our soul. And the argument that he makes is what that does is it gives us permission and power to program our mind and body and not listen to them. Right.

So when your body is telling you to be hesitant because, you know, it would be uncomfortable to run another mile, right? Well, that's just your body trying to keep you, you know, your body's goal is to keep you comfortable and to keep you comfortable and to keep you safe and another mile is going to stress your system. That doesn't mean it's bad for you, right? So it's like things like that. It's cool.

Okay. And my point in saying all that is I tend to work through these thought experiments because what you get out of them are sometimes very interesting. So these two questions. First question is, you're 80 years old. You're on your deathbed. What do you regret not doing? What's the thing you regret not?

Me? Okay. Well, we don't have to do this right now. We can get there. You can get there. That's great. I love it. I love it.

I've got, it's funny, I have a blink reaction. This is crazy. I have always wanted to learn how to make clothes. Okay, and I think there's a reason for that. I think I have sort of survival instincts. I want, you know, I want to learn how to cook. I want to learn how to make, be an entrepreneur and make money. I want to learn.

And I think that making clothes is almost part of that. I don't know. That's what I've convinced myself. Maybe it's just a kooky, I love that. And I want to come back to this idea of you have survival instincts in a second. So that's great. Okay,

so you have this idea, right? And maybe the bigger idea is a working knowledge of all the base things you would need to do to survive, right? Maybe that's the even bigger. Okay. So then the second question you ask yourself is, what did I want to do 12 months from now, or 12 months ago, that I still haven't done today, right?

and you make these two lists, and then you marry the two lists together, and the things that pop up on both lists are the things that your soul are telling you you need to do, right? This is something you've wanted to do and haven't done, and you know that if you don't do by the time you're 80 and you're on your deathbed, you're going to regret, and it should immediately focus you.

And I think where I was kind of going with this was, I think there are a lot of people that fantasize about the idea of being an entrepreneur, but in an honest, the goodness reflection, if they were 80 on their deathbed, not starting a company would not be something that they would necessarily really care about. And I think too often the sexiness,

the entrepreneur porn that you see out on the internet, it's so engaging, so shiny. It feels, you know, people get the most accolades. They sit on the stage, you know, and we want that, like intrinsically as a person. And, but it doesn't mean we actually want to be entrepreneurs. So I guess my question for you out of this is, like, how, like, you are obviously an entrepreneur.

You obviously have that desire. Your brain's wired that way. How did you know? Or did you know? Like, if I'm sitting here and I, I'm torn between, am I an entrepreneur or am I just bored at my job, how do you figure that out? How did you figure that out? Well, okay, this is interesting.

So I had maybe the greatest job, certainly like entry-level job in the world. I worked in marketing for the National Basketball Association. What's better than that? I actually, somebody asked me this the other day. Why did you ever leave that? Like, isn't that you're kind of a marketing guy. Isn't that the pinnacle? isn't that the and um and i remember adam silver i think was davidster and adam silver both said the same

thing which is look john it you're not going to find a better job than this um but if there's something telling you you have to go uh try i i can't give you stock options i can't give you you know the the um the satisfaction of having built something taking an idea and building it from the ground and imparting it into the world. If that's what you need, then by all means, you have our blessing and go do that. I will say, just to make the point even further, I was given entrepreneurial opportunities within the NBA. And so I started NBA Canada and launched the Raptors and Grizzles expansion franchises. And so even that, even entrepreneurialism, within the NBA wasn't enough for me.

And so I think it was just something oozing that, so for me, it was kind of easy because I had the greatest job and the greatest opportunities in the world. And there was still something I needed to scratch despite that. And so it was sort of a no-brainer. You have to go do that. What were the biggest things from that position working with the NBA and launching expansion franchises, which is incredible? Like, what did you take out of that?

Like, I mean, there's so many pieces to this. You know, again, we don't have to get into every nitty-gritty detail. But what are some of the big lessons that you took away from particularly marketing a sports franchise and then ultimately launching two new brands, two new core assets into a brand that had already existed? Yeah, I think, I mean, it was such a great experience at such a young age. We could fill hours with what I learned. For me, market positioning was such an interesting thing. We were going into this country, Canada, where people come out of the womb playing hockey, right?

And we were introducing sort of this new sport. And so what we decided was, okay, so who were we targeting with this thing? And ultimately we sort of wanted to go younger because we thought that the older people were more established in hockey and whatever else they were going to do. And so we wanted to be the younger alternative and kind of get people early in basketball. So who is your target? How do we frame this thing, this new NBA thing coming to this country? Is it sports? Is it entertainment?

Is it sports and entertainment? And that, while seemingly maybe pedantic actually was really important, right, like, what is this thing and how are we going to think about it and define it? And then what makes us different, right? Why should people care? How are we going? What is our unique differentiator among everyone else we put in our category, whether it's the NHL or other entertainment properties? And so just that sort of basic position. positioning, which any marketer will tell you is critical, like was really important and was

something I learned at an early age. And I think, I think served us well. I think if you look, we just celebrated the 30th anniversary of NBA Canada. And if you look back at how many kids are now playing basketball, how many Canadians are playing in the NBA, the Raptors want to champion. Like, you know, I think back and say those kids were watching the Raptors and wanted to emulate that. And now there's a WMBA team there. And so it's very, it was incredibly gratifying to see 30 years later, we had planted these seeds and the trees have grown and it's been great. Can you talk us through this positioning idea of entertainment versus sports? Like I think for a lot of non-marketers or just people who haven't spent a lot of time, you may say, well, what's the difference,

right? Like sports, entertainment is the same thing. It's basketball. So isn't it obviously sports. Why would you even need to explain the difference? Like, why is this such an important concept? Well, when you, when you drill down, right, when you think about I, I can spend a dollar and I'm going to bucket that dollar. It's probably not I'm going to spend that dollar on sports. It's I'm going to spend that dollar on sort of entertainment, right? And so I can either go to an NBA game or I can, you know, go to the movies or I can go wherever. Whatever. And so I think just from a share of wallet standpoint, you know, what, where, what pool are you playing in? Also, there's, there's the time thing, right?

I'm going to go spend an hour doing something. Am I going to play video games? Is your remote team drowning in a sea of apps? Zoom fatigue, slack spam, scheduling nightmares, it's absolute chaos. And you're paying a fortune for it. I want you to check out Rome, a virtual office that replaces eight of your team's tools. Zoom, Slack, Calendly, you name it for one insanely low price. And this is not a joke, $19.50 a month.

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So click the link in the description below. Get your demo today. I promise you, you will not be disappointed in Rome. So, ladies and gentlemen, a first for everything. Just had the circuit breaker for my office top. I think because it's really cold down here, and I have a space heater behind me. I bought this house two years ago.

It was built in 1960, but it hadn't been updated since 1960. It was crazy. Literally, there were a little. like paths in the carpet where the woman who had owned the house for 60 years had like walked. It was wild. But, you know, it's an older house. So like it wasn't designed to heat the basement, which is fine. You know, whatever.

And so I have a little space here that I use. And I didn't realize I just moved the space heater from like behind if you're watching the video, what would be my left shoulder to my right shoulder. And I plugged it into this power strip. And it just blew the circuit breaker mid-show. So I turn that off. We should be good moving forward. I like to think we generated so much energy and heat that it just, yes.

That's exactly. That's exactly. Maybe not. But, okay, so I don't know if you remember exactly where you were. Yeah, I do. Perfect. So we were talking about share of wallie. Share of wallet.

Yeah, yeah. And I think there's also a share of time. If I'm going to spend an hour of my time or two and a half hours in the case of an NBA game, am I going to do that, you know, playing video games, entertainment, am I going to do that, going to an NBA game, sports? And so I think it's very important to think about share of wallet, share of time, vis-a-vis what category you were actually in. I think this idea of share of wallet is something that most people do not even consider. I think at a Fortune 500, CMO, go-to-market, you know, executive level, I think it's a.

fairly common, but you get below the Fortune 500, particularly into middle market or even small business. It's not even a thought. One, I don't think positioning is something that most of these organizations think about. I think it's just, I'm an insurance agent. I sell insurance. That's my position. Or I have a coffee shop. You know, I sell coffee. That's my position, right? And they don't think about, well, how does your $4 coffee fit into every dollar that that person spends versus the gas station coffee versus the Starbucks brand it, you know, large mega brand coffee. Like, where do you fit in? Are you the luxury where you get the special, you know, foam picture with your face on it kind of thing?

Or are you the turn and burn 99 cent? You know, and like that's really important. What I think is interesting and I'd love for you to maybe expand upon, particularly with the NBA and how you approach that, was the share of time. Because I think share of wallet makes sense. We vote with our dollars, but we don't just vote with our dollars. We also vote with our attention, and that's kind of share of time. How do you, when you're approaching marketing something like the NBA to a new constituency,

which is heavily invested in another sport, in this case hockey, how do you start to convince them or what things did you try to get them to say, hey, we know you normally spend 10 hours a week watching hockey, We want you to spend eight hours a week watching hockey and two of those hours watching the NBA. Or, hey, we want you to add two more hours of sports watching into your week, which include the NBA. How do you start to make that commitment or get that commitment from your audience? Yeah, I think it's, I mean, certainly you put up the product and you hope that some people just transfer the time and that's easy. And then there's the harder work, which is, well, what else should we be doing? that could ultimately ladder people up to that two and a half hours, right?

If they've only got 10 minutes, maybe we should have NBA video games that allow you to play for 10 minutes and then you leave. Maybe we should, you know, if you only have 30 minutes and you actually want to go outside and get some exercise, maybe we should make sure there are enough hoops and balls in your neighborhood and community and a country ultimately where we can start building that brand affinity, delivering it to you in the way you want it delivered. In the time that you want it delivered at the price, playing hoops in the park is free. Maybe the video game costs a little bit of money. Maybe the NBA ticket costs a lot of money. So I think it's you have to think.

And then even licensed products, right? How do we get you to get that NBA, that Raptors or NICs trash can? and I'm thinking about, right, what is, that says something about me and my personal brand. Yeah, I kind of like these guys. And I want people to know that. And it acts as a reminder. And ultimately, over time, you can, you know, get people to move that share of time more broadly in the way that you would like. Having done, planted these sort of smaller seeds, ensuring that you are, um,

delivering that that to them in a way that they want to digest. By the way, even like, you know, working with television broadcasters to make sure that the clips of last night's game are digestible and, and, and, and, and the, and websites as well, again, to bring snackable options, which ultimately will ladder up to the two and a half hours you want them to spend going to a game. Yeah. It's so, it's so, it's such an interesting marketing process. to solve, you know, breaking into a new market like that.

You know, even, you know, you said, you know, just making sure they have enough basketballs. You know, I hadn't even wrapped my head around that. Like, are there enough courts for enough kids to actually play the game, you know, and have access to it? Okay. I'm going to tell you a story that is my favorite David Stern story. When I was growing up watching the NBA, there was a period of time where these guys would

do these dunks and they would shatter the backboard. Are you, do you remember that? Shaquille, I think Shaquille O'Neal Dawkins. Daryl Dawkins. Yeah, yeah. And it was, as a kid, it was thrilling. And wow, wasn't that amazing? And everyone would play the clips of that.

And we talk about it in school. And it was this moment. And I remember when I got to the NBA, David. And so if you're in an NBA arena, it takes maybe 25 minutes. to redo the backboard and then the game resumes. And all is, you know, that's not terrible. And I remember David saying, we have to stop this. And I was like, why?

It's so, it's terrific. And he said, because, John, if an NBA, if Daryl Dawkins breaks the backboard in an NBA game, it takes us 25 minutes to redo it. It's a minor disruption. And I agree, it's pretty interesting. If somebody tries to emulate that in Canada or Africa, and goes to a park and breaks that backboard, it takes 30 years to get that rebuilt. And so when I think about growing this game across the country and the world,

we have to take that long ball approach and make sure that people don't do things, that make sure that we don't display things that they can then do that will ultimately be a net negative for the sport. Isn't that? Yeah. That's interesting. I, um, my, my initial reaction would be to push back and say, well, let's figure out a way to get them more hoops versus stopping the backboard from breaking

because, like, like, what's, like, everybody who's ever spent any time with basketball has in their mind that picture of Michael Jordan jumping from the fall line. He's got the ball cocked back and it looks like he's just floating in space, right? and it was so iconic and it happens during the during the dunk contest when the superstars of the NBA would be part of the dunk contest and like you would you like would you would want to see the dunk contest more than the NBA All Star game because of these these feats that these guys would do right now that the NBA dunk contest is kind of a joke you never know you don't even know the guys half the guys don't even play in the NBA they're like dunk specialists that they bring in just for the contest and frankly it kind of is like a few clips and people move on and i say to myself like okay i get it like if i'm an NBA executive i'm going i don't want my superstar because they could twist an ankle and blah blah blah except there's no more iconic dunks like i i haven't seen a dunk in decades where i've been like that's a poster that's a poster now i don't know okay

yeah maybe maybe not i'm not as big an NBA fan as i used to be Right? But like, I can tell, I can, I remember, you know, oh my gosh, I want to say it's not, oh, my gosh, oh, my gosh, he played for the Hawks. Dominique Wilkins. Dominic Wilkins. I, the invent the windmill dunk, right? Just like, he swung his arm so hard.

You're like, how does he even hold on to the ball he would win mill dunk it so hard? You know, and those kind of things. And I still think there's iconic dunks, but all right. I don't know. They're just not showcased the same way. So I have two thoughts on that. So first, I think the penalty in the shattering of the backboard was very precise. It's not don't dunk, right?

Like, oh, my God. You can't hang on the rim after you dunk, right? And so I think that preserves the beauty and the grace and the excitement of the dunk without the negative implications of, you know, of breaking backboards all across the world. The other thing you said, which was interesting, is, boy, I would think about getting more backboards out there. Fair, but also this is where like partnership comes into play. The beautiful thing about the NBA is there are, you know, without the NBA's involvement,

there are people, organizations that put up these hoops all around the world on behalf of the sport. So, you know, we don't want to, we want to encourage that sense of community and other people helping us, as opposed to doing everything ourselves or, and making sure that our rules don't hurt the people who are trying to help us ultimately. Yeah, I think that's a really good, I think that's a really good take. These are the calls and these are the ideas that kind of make or break leaders, right? that this is the directions that you have to go. And I love walking through these. And I think I ultimately agree with you, you know, at the end of the day. I think it's, I love walking through these thought experiments, though,

because it helps you as you grow and you iterate. And now you've co-founded Rome. And for, you know, just full transparency, Rome is a partner of mine. I use Rome every single day. It's helped me replace a bunch of tools, big fans of you and your team. and it's been a pleasure to work with you.

But I had asked you on the show because, you know, you've had this just incredibly diverse and robust experience and success. And now you're doing it again. And you're taking on, in this case, software, which you have done before, right? So it's not like it's your first software play. But, you know, kind of juxting position against something like the NBA where the visuals are so dynamic and the cultural connection is so, I mean, it's just there.

It's like part of, you said, it's a part of people's soul. It's how they identify. I'm an NBA guy or I'm an NFL guy or I'm an MLB, right? Like we self-identifies these things. City pride, self-identity that's all wrapped up in that. Yes. And now your product is a remote office. And I don't, I'm broad stroking, right?

Broadstroking. Not exactly Michael Jordan, you know, kind of reverse dunking in the NBA and post-erizing. No one's got a poster of that really awesome message that they sent someone through Rome, you know, up on their wall. So how do you take the lessons of these more visual and visceral products and apply them to software products that someone is using every day to be more productive, to communicate better, to help enhance their business? Because I think a lot of times, and this is where the crux of my question is coming from, and some of this is coming out of the insurance industry, too, is... We hear lessons from someone like yourself who's worked with a product like the MBA, sexy, fun, exciting, right? And I think a lot of people, there becomes a disconnect or even a self-imposed disconnect between those lessons that you just shared with a product like the MBA to their software

product or their service product that doesn't seem as sexy as something like the NBA. Yeah. So what's funny about Roe's. Rome, we get, and it's great working with you and you, but I think, I think you felt something a lot of our users feel in using Rome. And what has happened in the handful of years that we've been doing this, we get, we have raving fans. If you just go to social media, you will see raving customers of Rome just raving about the software. and how much more productive it has made them, how much more a sense of culture it has built in their company,

and ultimately, you know, how much money it has saved them. And I've said not since I've worked at the NBA, which is a de facto monopoly, have I seen such raving fans for a product? And so in that sense, there are some parallels. But I also, you know, just like I talked about going back to Canada 30 years after, that's what I'm excited about with Rome. I actually believe this is a generational product. I believe we're going to look back, you know, 30 years after the advent of Rome and see how it has changed the way people work, how it has changed people's relationship to physical offices and around the world.

And I honestly believe that we will have built a fandom, a culture that is certainly different from the NBA, but it has a lot of that, right? It has a lot of that feeling of, man, like, I just love this brand. And this brand has done really important, meaningful things for me, for my community. and the interesting thing about Rome, too, is it's sort of, there's this downstream effect. We build this platform. Thousands of companies come onto the platform. They bring other companies on. They hire people.

And so it's really gratifying to know that the impact that you are having on all of these people, not unlike the NBA, right? There are 30 teams and, you know, 802 games. or whatever. But the downstream impact of all of that is powerful. And that's what we're hoping to get to with Rome. So I think there's some parallels. Obviously, a lot of differences, too, but that's maybe how I would think about it. Well, I think you just made an important point, which is, in essence, if I'm paraphrasing, is essentially we are forming the same brand identity, like patches on our shirt with software products as we have.

have with the town we're from, the high school we went to, the college we went to, the sports teams we follow, you know, et cetera, et cetera, the books we read, the podcast we listen to, like, all these, it's extended into the products we use. I think for a long time, maybe we, and maybe pre-internet, we didn't associate our, our personal, brand to the, to the tools we used, right? But today, you're Microsoft or your Google, your Open AI or you're Claude. You know, like we look at these things and I think, you know, to me, I look at it and it's like, I think there will come a day where it's am I, am I Rome or am I Slack or am I teams, right?

And like you start to develop and how that tool works and what it means to you kind of defines your company culture, your value structure, what's important to you. and, you know, in that regard, what are you hoping, you know, if you had the perfect brand connection, right? So just in your mind, someone steps up on stage and they said, you know, when I use Rome, it makes me feel bam, right? Like, this is my brand connection. What does that perfect thing look like for you? In the flow, period, full stop. That is what we want to do here.

We want to make people so productive, build so much culture, make them feel so good that they are in the flow at all. That is the highest state, certainly from a work standpoint, maybe from a human standpoint. And I think that like that is the, if people could would say when I use Rome, I feel like I, or when I use Rome, I am in the flow. mission accomplished. By the way, but I think you made such a good point. I used to talk about when people hold up a coffee cup that says Starbucks versus have a nice day, it actually says a lot about their personal brand. And if you're an outside person or a candidate that's being interviewed and you come into somebody's Zoom box or versus Rome office, it says a lot.

about the brand of the company, how you think about the importance of being in the flow, how you think about growing your employees because they can get up to speed easier. They have access to people. That's easier. And so, yeah, I think the brand thing is very relevant from a software standpoint. If I'm using, like,

We all see it. If I'm using an iPhone versus I'm using an Android phone, it just says something about me. Yeah, I immediately think that you're a dumbass if you're using a non-apple phone. Cheap. Cheap. Yeah, usually cheap. Like, product functionality doesn't matter as much to you. Yeah, yeah.

Yeah, yeah. You know, it's weird. And I know that's bad because I have family members that use them, although I do obnoxiously call them out every time I see it. Yeah, do they get invited to Thanksgiving or, like, do they have to sit at a separate table? Well, here's the funny part. So my dad gets a new phone, right? He's had a Google phone forever for all the reasons that you just said. He's cheap and blah, blah, blah, blah.

And he's only got a Gmail and all this stuff. So, you know, he's, he is the... At least that, not, I mean, it's not like Outlook or it's not... Well, it took me a while to get him off AOL. Trust me. Yeah, yeah. But, you know, he's like the classic, like, old school, like Luddite guy, you know, the throw your hands up in the air kind of technology.

And I just said to him, I was like, you know, so he wants to get a new phone. and he gets the Google phone, he gets another Google phone or whatever, Android phone, and then he can't figure out how to use it. And I just was like, this is the problem. Like, this is what I told you. I was like, if you got an Apple phone, there's a little wizard that in three button clicks,

everything's set up, all your data's back, your phone works just like the phone you had before, finger snap, move on, you lose zero time. I go, the fact that you have to like download this package and upload it here and do this and add this thing, and say i'm like that you made that decision right and and the point being i think far too few leaders executives etc spend time thinking about what like their product the way you just said it right to help people get into flow to be in the flow of their day to facilitate them doing their best

work their deepest work etc is there an exercise that that you have and you know it's probably fairly deep so so we could just kind of touch the surface to help leaders who are sitting here think about this this this type of you know how their product actually integrates into people's lives because I see a lot of a lot of frustration a lot of stagnation is just this surface level I sell insert widget insert service why don't people want to buy it and it's like well what does it mean to them what do you want them to think when they work with you like do you have like a thought experiment or just even some simple framework or reference points? I have two and it comes back to positioning right so here's a very simple statement to target audience

Rome is the frame of reference that offers unique selling proposition to target audience Rome is the frame of reference that offers unique selling proposition reasons why One, two, three. Tone and manner. One, two, three. So, why could you say that, that NBA Canada is the most entertaining and unique sports property in the country? Why could you say? What are the supporting points to that that we're going to emphasize in everything we do?

And what's the tone and manner that we're going to do everything in? from designing this t-shirt to the software to the in-game experience, is it responsible? Is it bleeding edge? Is it a for? Like, I don't know. But like if you just put that on one piece of paper, everything you do, you can hold that up to, right? How should, what do you think of this homepage? Well, how does it do against our positioning here?

What do you think of this commercial? And so I think that's a, that is a technique. The other that I'm big on is, which is sort of similar, it's net consumer takeaway. If I'm running an ad or I do a video, it's exactly what you asked me. It's what do I want people to take away from that ad? What's the feeling? What's the quick response? Like, oh, I just saw that thing.

What's the takeaway? And it helps everyone gets, you know, all bogged down in what words should I use here? And all that's important, but I think you also need to take a step back. There's this Harvard Business School thing for startups that a balcony and dance floor, like you need to spend a ton of time on the dance floor, right, getting into everything. But then you've got to raise up to the balcony. And so I think that these things help create framework for balcony raising when we're in the absolute day-to-day, you know, 24-7 minutia. Because without these exercises, and I love that, I love that exercise.

there's brand confusion, right? And I think a lot of us, when we don't slow down enough guys and we don't go through these thought experiments like John is describing, what happens is people are confused as to who we are, what we actually do, and why they should care.

And even, you know, I go back to my insurance friends, I think there's an assumption that because I say I do insurance or I sell insurance or I own an insurance agency, that people automatically assume what we do, what we sell, why we do it, right? And I'll give you a case and point. My agency that I founded, Rogue Risk, we got a ton of inquiries for workers' compensation.

And a lot of those inquiries were from businesses that already had general liability or property insurance, oftentimes with another independent insurance agent. Now, why in the world would they be reaching out via the internet to rogue risk, a digital insurance agency for workers' comp, when the agent they're already working with, most likely in their hometown, sells that product. And the reason was that agency had never positioned themselves

either as a commercial line specialist with broad coverages or as someone who could sell workers' companies. They literally never positioned themselves as that thing. So even though the person in some cases have been doing business with them for five, seven, 10 years, they did not know. So they're reaching out to us, right? So think about that. You're losing business because you didn't think through the positioning and how you, like,

how do you get rid of the assumptions that, how do you remove your assumptions that your audience knows what you do, right? And it's these types of experiments. It's, it's this kind of. And then, you know, tell me if I'm wrong here, but like, knows what you, knows what you do. and makes it unique. What is it, right? It's not just that you sell insurance.

It's here is how I position myself. Here is what's unique about the way I do that versus my competitor. And then you got to, right, and this, I think this is the part. And here's where I have a question for you is oftentimes we say something once and we assume everyone hurt us. Right? So, so, you know, just maybe level set for both for both Rome, maybe something. some of your past experience with Patrick and Fide or even like the NBA, like got it. Like I'll give you a case and point, right?

I made the comment before about how there's no iconic dunks anymore and you immediately reacted, right? So if you're if you're listening, you may not have picked up on it. But when I said that, if you're watching on YouTube, you saw John had immediate physical reaction to that, which tells me I just am not aware of these iconic dunks, not that they're not happening. Right? So my point being, here's the NBA.

here's, you know, we, one of the most marketed sports entertainment organizations in the world, right? And there are iconic things happening that I'm not seeing. So if a sports fan is not seeing, think about how many times you've got to talk about your product for people to see, right? Just. Yeah. As an executive at AOL, when we spun out of time where we were a standalone public company, maybe 5,000 people, I felt my job was simply to repeat everything all the time. That was my job.

Just in different ways to different people and different media, just keep saying it. It's so important to align 5,000 people. And this idea of, wait, I said that, right? How could they not, I mean, particularly in this day and age where it's the attention economy and we've got dopamine attention hits all over the place. You have to say things repeatedly. I don't know if there's a particular number, but. far more than you want to and far more than you think is necessary.

And that is, so that is yes, whether that's your advertising, whether it's internal communication, it's any, any form of communication. Repetition is your friend. Yeah, I, I was talking to my kids. Let me say that again. Repetition is your friend. Yeah, it was funny. I was, so I'm divorced and, you know, my kids, obviously they know.

Like, you know, I, I, they know that I, you know, I'm dating a woman now or whatever. And, you know, we're talking in general. Something came up on the TV and we were talking about, you know, how do you get women's attention? Right. That's, that's the question that came up from my 12 and 10 year old. You look like you, Ryan. Jeez. I mean, what else?

What else do we need here? Not. Hopefully they'll be good looking guys. Better looking than me. But they, I said, look, I said, the easiest way. say her name seven times while you talk to her. Just say her name. You just say, you know, hi, Sarah, how are you today?

Hey, Sarah, what did you get on the test? Hey, Sarah, you go into a homeroom. Hey, Sarah, you know, you just, you, I go, I promise you, she will know who you are and you will, you know, you're most likely got her attention. Doesn't mean she's going to say yes to the date. Doesn't mean she's going to like you. But if you say her name, particularly her name over and over again, right,

was, you know, maybe surrounded by something either that you noticed about her or that she's doing that's engaging, right? You're drawing her in. You're building a brand of understanding and caring and attention. And now you've said it. I go, she ain't going to forget you. In fact, you will probably have wedged yourself so deeply into her subconscious that she can't help but be interested in you. I said, but this works, you know, that might sound sneaky and bad. But guys, it does work. If you're struggling with women, that does work. Doesn't work every time. So I'm going to play podcast host. Does that translate to business for you as well, that same concept?

Yes, yes. Does that translate into business, Ryan Hanley? Does that? Yeah, I'll tell you. So, you know, one of the things that I used to teach, and the reason for telling that story is because it does translate to business. So one of the things that I taught at Rogue Risk with inbound sales was always, always mentioning their name, right?

Always saying their name. And we had a whole script. and, you know, I built the most efficient and effective inbound sales flow. It's called the master of the close flow in history. We were closing 89% of all qualified leads on inbound calls. It was what allowed us to scale so fast, and it was all based in human psychology. And one of those psychological principles was being very specific in this case with a name and repeating it over and over packaged around thoughtful comments, open-ended questions,

et cetera, et cetera. So you package these things together. But it was the repetition that started to lock into their brain. This person knows me, right? If I use your name, John, John over and over again, you can't help but start to think, Ryan knows me. He understands me. He wants to be, you know, he's showing interest in me, right?

And it draws you in. And we have to do this. But a thousand times, a thousand times over, right, for our ICP, our preferred client, right, our preferred customer, because, like, one social media message, it's only going to be seen by this tiny little fraction. And even there, no one's going to remember it because it's only once. So even if that tiny fraction was the only fraction that saw your message every time out, you still have to hit them five, seven, ten, eleven, God knows how many times today

with how many other distractions they have. So it's like regardless if you're marketing the MBA or you're marketing a software product or you're marketing Rome or you're marketing yourself to the other sex, right? Right. It's this repetition and show of interest that that wedges you into their brain. And if you're not willing to put in that work, you simply just, you will not stand out. You will not get that brand recognition.

And I find repetition is your friend, as I have said four or five times already. Yes. So I want to be respectful of your time and this has been incredible. Particularly with Rome, I will have. links guys in the in the show notes whether you're watching on youtube or whatever click those links you you're able to go through schedule a demo i highly recommend if you have a remote workforce and i'm going to do just a little bit of sales job and look guys in transparency i told you i am partner with rome they are a sponsor of the show but i wanted to bring john in hopefully you took

that this was wow way more than just a commercial for rome your experience is incredible we could have dove into so many more topics but i do believe in what you're doing and what you're building because I look at our world in, we had this huge move to fully remote with COVID, right? Just pushed us all the way to fully remote, which is great. But it feels to me like the pendulum is starting to swing back to a true hybrid in-person remote world. And then you have layered in what remote actually means. There's hybrid two days a week, three days out. There's out all the time. There's out all the time and in a different area. There's out all the time and in a different country. And to me, in all the different tools that I've worked with, there's no tool.

There's no platform that I believe marries a fully in person, the conversations and digital tools necessary for fully in person, all the way to fully remote international that can take any one of those scenarios and all those scenarios and allow a team to interact with each other, you know, not to mention it replaces calendar, loom, all these tools in one. So it's been an incredible partnership. It's been an incredible tool for my business. But not just Rome. Where can people go deeper into your world?

Because you have so much experience and I know you continue to share it. How do they follow along with your thoughts and what you have going on? I mean, feel free to, I'm a reasonable LinkedIn poster. So follow me on LinkedIn. Also just email me at Rome, John, j-on, at ro.am. I love helping entrepreneurs. I love helping people to the extent that I can. So please reach out.

And yeah, let's see if there's anything we can do together or if there's any way I can be of assistance. I appreciate you so much, John. This has been an incredible conversation and your flexibility through our power outage of the episode as well. So I wish you know about the best, man. We'll talk again in the future. Thanks, brother. Appreciate it.

Thank you.