He Quit the Best Job in the World. Then Built Something Better. - Jon Brod

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 i- 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 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. 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, is fairly unique.

A lot of times when I'm, you know, researching someone for the show and, and getting ready to talk to them, i- most of their experience sits in a couple buckets, you know, or one, one main bucket. You know, even, even myself. You know, most of my career, uh, and most of what, you know, m- 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, um, and obviously media, but, um, but you know, that's the core. MBA, uh, communication apps, um, you know, all these different things that you've done.

It's a, it's a fairly, like, robust and, and wide swath of, of different... You know, and I'm sure there's a through line, but, um- Not m- 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, "Oh-" Yeah ... "that word, that word doesn't get enough love."

But wha- here's what's interesting. So I s- I, 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 myself and my journey and my story, so this will be interesting for me because I just, like... I'm actually a little bit nervous, believe it or not. I don't know, um, because I, I, you know, it's like the imposter syn- Like, I can't imagine I have anything worth, uh, valuable to, to, to tell, tell the audience here. But I'm, I'm excited for, uh, 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, uh, that you've worked on, companies you've started, the number of, of exited companies that you have, and the continued success now with Roam, h- how does a guy like you have any kind of imposter syndrome? 'Cause I think most people listening, when they look through your resume would be like, "You're either full of shit or, um, what am I supposed to do if this dude's got imposter syndrome?" That's hysterical. Uh, you know, uh, look, I, I have high expectations, uh, for the companies I work at and, and with for, and for myself, and I feel like, yes, I have a, had a good, interesting career to date. Uh, I've had a bunch of success.

I've had some, you know, failures or l- 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, um, imposter syndrome, fear, hesita- whatever.

One of the things that I try to teach my kids, and I, and I'm interested in your take on this. Uh, we, we were actually just talking about this with basketball the other day. Uh, 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, um, he still, you know, he, he struggles sometimes. And I asked him one day, like, "Why..."

Like, "I've seen you do things that I, one, I didn't even know you could do, that I think are pretty fantastic for your age. Um, but then in the games, you kinda, you kinda get small, right?" And, um, and he said, um, he, he was honest enough to say that he has fear. Right. And what I thought in that-- So we have this conversation about fear and, and one of the things that came out, and, 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, I shouldn't say it. I think it's a big misunderstanding, myth, et cetera, that elite performers, people who've achieved success, that the next time they, they don't feel fear. They've, they've like, they've, uh, um, they've beaten fear down and somehow are victorious over fear. And I said to him, I go, "I've done four hundred 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 Roam now, right?

You've had all this success. You're gonna take on another startup, right? How do you deal with that fear that inevitably comes up when you're gonna 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, so well done there. Um, but you used the word I was gonna use, which is the channeling of the fear, right?

Like, um, I-- It's so funny. I would get nervous if I wasn't nervous, right? Um, and, and so because you're supposed to be nervous, and you're, that, that's, that's healthy every time I take the stage or I do a podcast or I do a TV appearance. Um, and so- Uh, I think that's, that's all right, and that's all healthy, and, and then it's t- uh, then it's channeling that fear into, um, positivity and, and some level of confidence. Um, but yes, I, I, I...

Discomfort is what I believe what grows us, right? That, that's where we learn, that's where we challenge, that's where we overcome obstacles and, and ultimately how we grow. So, um, I have spent a career putting myself in uncomfortable situations, uh, uh, b- because I wanna grow, and I wanna change, and I wanna... Uh, by the way, like, uh, Mindset is, uh, an incredible book by, uh, Carol Dweck, and we actually make everybody at Roam read it, um, because, you know, it's, it... Your mind, like, that's something you need to work on.

It's, it's a muscle, and you need to be dis- uncomfortable. You need to have a bit of imposter syndrome, or you need to be nervous, and that means, you know... And then, uh, ultimately good things come of that, out of that, even if it, if short-term failure, um, medium to long-term goodness. Yeah. I, I was listening to this conversation, uh, or it was a podcast.

Uh, Tony Robbins was on, uh, Diary of a CEO, and he talked about these five, I'm just gonna say, things that everybody needs, and he goes through each one, um, throughout the podcast. But there were two that seemingly are diametrically opposed that they spent an awful lot of time on, and, and I found it to be a r- probably the most engaging part of the conversation was this, 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 it, and he, and he really digs in, and I, I won't do justice to, 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, um, that balance is, it's really difficult because we all desire, "I wanna make sure my family's taken care of. I wanna make sure I'm taken care of. I wanna 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, um, you know, particularly high growth, high achievers, entrepreneurs, intrapreneurs, 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. Yeah. How, when you're, when you're looking at a project, again, like Roam 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, it's worth taking on this risk?

Especially, and, and this is kinda where my question goes, I think early on, right, we can take on massive amounts of uncertainty. Yeah. We're in our early 20s- Yeah ... late 20s, right? But we start to get into our 40s, our 50s, we've had some success, we have some things to protect. Th- that's a t- you know, it's tough to balance taking on that much uncertainty again, et cetera.

So how do you deal with that equation? Um, I, I think you're right that, uh, it, a lot of it has to do with age and, you know, with dependence and with financial obligations. Um, and, and so, uh, everybody has to sort of do their own calculus. Um, for me, um, y- you know, I, I had early success, which was great, and that allowed me to continue to do, uh, and take, take risks and do, uh, all, some of, all the things that I've, I've done. Um, but, you know, how do I assess the risk?

I, um... One is like how big an opportunity is this, right? What, like wh- TAM, total addressable market, but just more generally, is this a big idea, or is this sort of a, a niche idea? Uh, and so that's part of the calculus. Um, who are the people that I'm doing this with?

I, 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. Um, and it's really the i- uh, 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 s- probably first because they drive the execution and ultimately the idea changes, um, as pa- uh, in, in the process. Um, so I think that's, that's all part of my...

And, 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, and, and that has, um, um, made the calculus easier. These are known quantities. We know, uh, what we're each good at and, and, and sort of how the puzzle fits together. We trust each other, um, and we can move quickly because we have a common shared language. Uh, so I think that, that's all.

But, but look, ultimately, you know, you, you've gotta y- you have certain things you probably need to do, take care of your family, your mortgage, whatever it is, and you, and you need to make sure that these risks are, um, the right risk profile for you, right? Like is it, right, everybody has their own risk profile, uh, so I'm not gonna prescribe that. But, um, I, I certainly took hu- huge swings when I was a kid. They turned out well, which allowed me to take, uh, continue to take swings as I now have two children that are high school, uh, age and, and going to college and, and, and all of the associated costs, um, and time that's required, uh, 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, so don't, don't take that as a negative. But you've, you got the corporate job. It worked for you. You fit in. You made money.

Um, you had, you have, have had an, uh, 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, to kind of pull that thread. You know, do, do you have any advice or guidance or, or thoughts for that level of entrepreneur, that type of entrepreneur who's maybe in the, the second, 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 are really entrepreneurial, right, and, and, and, uh, go do it bec- because actually you've built up in the first part of your career, um, um, uh, you know, a, a fallback plan, right? You...

Like, you, you've been successful at your, at your job, whatever the, whatever that is and, and whatever size company that was. You can probably go back to that. Uh, right? And, and so you've done, you've done some of the, the, the, the work that, the, the confidence-building work that will allow you to then take, take the risk. Um, do it.

It is so damn, um, gratifying. Again, like, win, lose, or draw, like, you will learn a ton. Uh, I would probably time box it, uh, right, if, if, if you've got, uh, some financial constraints. You know, say, "I'm gonna 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." Um, but, but do it. Do it. I mean, like, uh, there's this phrase, um, that someone told me.

Like, let... This isn't a... Th- this is our one big beautiful life. This isn't a dress rehearsal. And so if you are gonna get to the end of it and, and regret that you didn't do that, please go do it.

Yeah. I, I was given this exercise, and I actually wrote about it, um, at Finding Peak, and it's, it's two questions. Uh, the first que- and 'cause I, I love thought experiments. Um, I realized a long time ago that my brain is broken in a lot of different ways, and, uh, the best part about that is, um, 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. Um, and, and if you've ever read, uh, if you've, if, if you've never read, um, Untethered Soul by Michael Singer, it's a fantastic book, very short, very quick read.

Um, and the idea is, uh, we are not our mind and we are not our body, we are our soul, and that, and the, and the, the argument that he makes is we... what that does is it gives us permission and power to program our mind and body and not listen to them, right? So, uh, when your body's telling you to be hesitant because, you know, it, 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 safe, and another mile is gonna stress your system. That doesn't mean it's bad for you, right?

So it's like things like that. It's go- Okay, and my point in saying all that is I, I tend to work through these thought experiments because what you get out of them are sometimes very interesting. So, so these two questions. First question is, um, you're 80 years old, you're on your deathbed- Yeah ... what do you regret not doing? Right.

What's the thing you regret not doing? Me? Okay. Well, we don't, we don't have to do this right now. We can get there.

No, no. We can get there, but just- That's, that's great. I love it. I love it. Yeah.

I've got... It's funny, I have a, I have a blink reaction. Um, this is crazy. I have always wanted to learn how to make clothes. Okay, b- and I think there's a reason for that.

I think I, I, I have sort of survival instincts. I, I want, uh, you know, I want to learn how to cook. I want to learn how to make... be an entrepreneur and make money. I wanna learn, and I think that, that making clothes is almost part of that. I, that, I don't know, that's, that's what I've convinced myself.

Maybe it's just a, a kooky, kooky habit. No, I love that, and I wanna come back to this idea of you have survival instincts in a second. So that's great. Yeah, yeah. Okay, so you have this idea, right?

Right. And maybe the bigger idea is, is, is a working knowledge of all the base things you would need to do to survive, right? Maybe that's the, the even bigger... Okay. So then the second question you ask yourself is: What did I wanna 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 gonna regret. And it im- it sh- it, um, should immediately focus you. And, um, I think, you know, where I was kinda going with this was I think there are a lot of people that fantasize about the idea of an ent- being an entrepreneur, but in an honest to goodness reflection, if they were 80 on their deathbed, not starting a c- company would not be something that they would necessarily really care about. And I think too often the sexiness, the, the- Yeah ... entrepreneur porn that you see out on the internet, it, it, it, 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, and we want that, like, intrinsically as a person. Yeah. Yeah.

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? Mm. Or, or did you know? Like, if, if I'm sitting here and I, 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 or, like, entry-level job in the world. I was, I worked in marketing for the National Basketball Association. What's better than that?

Um, that I mean, I actually-- Somebody asked me this the other day, "Why did you ever leave that? Like, isn't that-- You, you're kind of a marketing guy. Isn't that the pinnacle? Isn't that the..." And, um, and I remember Adam Silver, Da- maybe, uh, I think it was David Stern and Adam Silver bo-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, the, um, the satisfaction of having built something, of, of taking an idea and building it from the ground, uh, and imparting it into the world. If that's what you need, then by all means, you have our blessing, and, and go, and go do that." Um, I will say, th- just to, just to make the point even further, I was given intrapreneurial opportunities within the NBA. Um, and so, uh, I started NBA Canada and, and launched the Raptors and Grizzlies expansion franchises.

And so, um, even that, even entrepreneurial-ism within the NBA wasn't enough for me. And so I think the, it was just something oozing that, that's, that... So for me, it was kind of easy because I had, um, the greatest job, uh, and the greatest opportunities in the world, and I, there was still something, an itch I needed to scratch despite that. And so it was sort of a no-brainer, um, you have to go do that. What were the biggest things from, from that position working with the NBA and launching expansion franchises, which is incredible?

Like, w-what did you take out of that? Like, w- I mean, there's so many pieces to this. I, you know, again, I, we don't have to get into every nitty-gritty detail, but, uh, 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, two, two core assets into a brand that had already existed? Yeah. I think, um, I mean, it was such a great experience at such a young age, and there were, I, we could fill hours with what I learned.

Um, for me, um, market positioning was such an interesting thing. We were mov- We were going into this country, Canada, that where, where people come out of the womb playing hockey, right? And, and we were introducing sort of this new sport, and so, um, what we decided was, um, okay, so, so who are we targeting with this thing? And, and how do we, uh, r- and, and ultimately, we, we sort of wanted to go younger because we thought that the older, uh, uh, people were more established in, in hockey and whatever else they were gonna do. And so we wanted to, uh, be the younger alternative and kinda get people early, uh, in basketball.

So po- so posi- so who's your target? How do we, 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, and that, while seemingly, um, maybe pedantic, actually was really important, right? Like, what is this thing, and how are we going to, um, think about it and define it? Uh, and then, um, what makes us different, right? What... Why, why should people care?

How are we going-- What is our unique differentiator betw- a-among everyone else we put in our category, whether it's the NHL or other entertainment properties? And so just that, that sort of basic positioning, um, which any marketer will, will tell you is critical, like, was really important and was something I learned, uh, at an early age and I think, I think served us well. I think if you look, we just celebrated the thirtieth anniversary of, of NBA Canada, and if you look back at, at the success, how many kids are now playing basketball, how many Canadians are playing in the NBA, uh, w- the Raptors won a champion. Like, you know, uh, I think back and say, those kids were watching the Raptors and wanted to emulate that, and now there's a WNBA team there. And so it's, it's very, um, it was incredibly gratifying to see thirty years later we had planted these seeds, and the trees have grown, and, and it's been great.

Can you talk us through this positioning idea of entertainment versus sports? Like, I think for- Mm-hmm ... 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? Yeah. Like, sports, entertainment's the same thing.

It's basketball, so isn't it obviously sports? W-w-why would you even need to explain- Yeah ... the difference? Like, w-why is this such an important concept? Well, when you, when you drill down, right, wh-when you think about I, um, I can spend a dollar, and, and I'm gonna bucket that dollar, it, it's probably not I'm gonna spend that dollar on sports. It's I'm gonna 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 wh- wherever, whatever. And so I think just from a share of wallet standpoint, you know, what, where, what, what pool are you playing in? Also, there's the, it, there's the time thing, right? I'm gonna go spend an hour doing something. Am I gonna play video games?

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So ladies and gentlemen, a first for everything. Uh, just had the circuit breaker for my office pop, uh, I think 'cause it's really cold down here, and I have a, like, a space heater behind me. Um, so like when I, I, when I bought this house two years ago, um, it was built in nineteen sixty, but it hadn't been updated since nineteen sixty. It was crazy. Um, literally there were, like, paths in the carpet where the woman who had owned the house for sixty years had, like, walked.

It was wild. Um, but you know, it's an older house, so, like, it wasn't designed to heat the basement, which is fine, uh, you know, whatever. And so I have a little space heater that I use, um, 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 and it just blew the circuit breaker mid-show. So, um, so I turned that off.

We should be good moving forward. Um- I like to think we generated so much energy and heat- That, yeah, yeah, yeah ... that it just... Yes. Um, but- That's exactly, that's exactly what happened. Maybe not.

Yeah. But, um, okay. So I don't know if you remember exactly where you were in your presentation. Yeah, I do. Perfect.

Uh, r- so, so, um, we were talking about share of w- of do- of, of wallet. Share of wallet, yep. Uh, wal- yeah, yeah, and I think there's also a share of time. If I'm gonna spend an hour of my time, uh, or two and a half hours in the case of an NBA game, am I gonna do that, you know, um, uh, playing video games, entertainment? Am I gonna do that going to an NBA game, sports?

And so I think, um, it's very important to think about share of wallet, share of time, vis-à-vis what category you are actually in. I think this idea of share of wallet is something that most people do not even consider. I think at a Fortune five hundred CMO go-to-market, you know, uh, executive level, I think it's fairly common, but you get below the Fortune five hundred, particularly into middle market or, 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 four dollar coffee fit into every dollar that that person spends versus the gas station coffee versus the Starbucks branded, you know, large mega brand coffee?

Like, where do you fit in? Are you the, are you the luxury where you get the special, you know, foam picture with your face on it kinda thing? Or are you the turn and burn ninety-nine cent... You know, and, and, like, that's really important. What I, 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. 'Cause I think share of- Hmm ... 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, to a, a, a new constituency, which is heavily invested in another sport, in this case hockey, um, how do you start to convince them, or, 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, how do you start to make that commitment or get that commitment from your audience? Yeah. I, I, I think it's, um... Y- ma-- I mean, certainly you put up the product, and you hope that, that some people just transfer the time and, 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 ten minutes, um, maybe we should have NBA video games that allow you to play for ten minutes, uh, and then you leave. Maybe we should, you know, if you only have thirty minutes and you actually wanna go outside and get some exercise, maybe we should make sure there are enough hoops, uh, and balls, uh, in your neighborhood and community and, uh, c- country ultimately, where, where we can start building that brand affinity, um, delivering it to you in the way you want it delivered, in the, in the time, uh, that you want it delivered, at the, at the price. Playing hoops in the park is free. Maybe the video game costs a little bit of money. Maybe the NBA ticket, you know, costs a lot of money.

Um, so I think it's, you have to think... And then, you know, even licensed products, right? How do we, how do we get you to, you know, get that NBA, that, that, uh, Raptors or Knicks trash can and, and all... I'm thinking about, right, what is that? That says something about me and my bor- my personal brand.

"Yeah, I kinda like these guys, and I want people to know that." And it's, it acts as a reminder, um, and, uh, ultimately, over time, you can m- you know, get people to, um, move that share of time more, more broadly in the way that you would like, having done, planted these s- sort of smaller seeds, ensuring that you're, um, delivering that, that to them in a way that they wanna digest. By the way, even, even, like, um, you know, working with television broadcasters to make sure that the, that the clips of last night's game are digestible and, and, and, and, and the, uh, and websites as well, uh, again, delivering, uh, snackable options which ultimately will ladder up to the two and a half hours you want them to spend, uh, going to a game. Yeah. It's so, it's so...

It's such an interesting marketing problem to solve, you know, breaking into a new market like that. You know, even, you know, you, 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 gonna tell you a story that is my favorite David Stern story.

Um- When I was growing up, the, watching the NBA, there was a period of time where, um, these guys would do these dunks and they would shatter the backboard. Are you, do you remember that? Yep. Shaquille- And- I think Shaquille O'Neal, um- And Darryl Dawkins dunk- Yep, Darryl Dawkins ... dunks, the, all, all these g- Yep Yeah, yeah. Um, a- and it was, as a kid, uh, it was thrilling, and wow, wasn't that amazing?

And every, uh, would, everyone would play the, the, the clips of that. Um, and it, and you would talk about it in school, and it was this moment. And I remember when I got to the NBA, um, Da- uh, David, and then so if you're in, in an NBA arena, it takes maybe 25 minutes to redo the backboard, and, and, uh, and then the game, uh, resumes, and all is, you know, not, that's not terrible. And I, uh, I remember David, um, saying, "We have to stop this." And I was like, "Why?

It's so, it's terrific. It's, everyone..." And he said, "Because, John, if, if an NBA, if, if Darryl Dawkins breaks the backboard in an NBA game, it takes us 25 minutes to, to redo it. It's a minor disruption," and, 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, uh, and make sure that people don't do things, that make sure that we don't display things that they can then do, do that will ultimately be a net negative for the sport. Isn't that- That's- 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 foul line.

He's got the ball cocked back, and it looks like he's just floating in space, right? And, and it was so iconic, and it, 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, you, like, would, you would, you would wanna see the dunk contest more than the NBA All-Star Game because of these, uh, 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."

Oh. Now may- I don't know. Okay. No. Yeah.

May- maybe, maybe not. I'm not as big an NBA fan as I used to be. Yeah. Right? But, like, I can tell, I c- I remember, you know, um, oh my gosh, uh, I wanna say, um, it's not, uh, oh my gosh, uh, he played for the Hawks.

Um- Dominique Wilkins. Dominique Wilkins. I, the, the, invents the windmill dunk, right? Just, like- Okay ... 'cause he swung his arm so hard, you're like, how does he even hold onto the ball he would windmill dunk it so hard, you know, and those kinda things. And, and I still think there's iconic dunks, but- All right ...

I don't know. They're just not showcased- So- ... the same way. So I have two thoughts on that. Yeah. So first, I think the, the, the p- the penalty in the shattering of the backboard was, was very precise.

It's not, "Don't dunk," right? Like, oh my God. Yeah. It's, it's, 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, uh, of breaking backboards, uh, all across the world.

The other thing you said, which was interesting, is, um, boy, I would think about getting more backboards out there. Uh, fair, but also r- uh, this is where, like, um, partnership, uh, comes into play. W- the b- the beautiful thing about the NBA is there are, you know, w- without the NBA's involvement, there are people, organizations that put up these hoops all around the world, uh, on, on behalf of the sport. So, um, you know, we, we don't want to, we wanna encourage that sense of community and, and o- other people helping us, uh, as opposed to doing everything ourselves or, uh, and, and making sure that our rules don't hurt the people who are trying to help us ultimately. Yeah, I th- 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, that kinda make or break leaders, right? That this is, this is the, the directions that you, you have to go. And I, and I love walking through these, and I, I think I ultimately agree with you, you know, at the end of the day. I, I think it's, I love walking through these thought experiments, though, because it helps you as you grow and you iterate. And now, uh, you've co-founded Rome.

Um, and for, for, you know, just full transparency, uh, Rome is a, is a partner of mine. I use Rome every single day. Uh, it's helped me replace a bunch of tools. Uh, big fans of you and your team, and it's been a pleasure to work with you. But, um, I, I had, I had asked you on the, the show because, you know, you've had this just incredibly diverse and robust experience and success and, and now you're doing it again, and you're taking on, in this case, uh, software, which, which you have done before, right?

So it's not like it's your first software play. But, you know, kinda juxtaposition against something like the NBA where, um, the visuals are so dynamic and the, the, the cultural connection is so, um, just I mean, it's just there. It's like part... You said it's a part of people's soul. It's how they identify.

I'm a, I'm an NBA guy, or, or I'm an NFL guy, or I'm an L- MLB, right? Like we- Yeah ... we self-identify as these things, and we, we- City, city pride, self-identity, that's all wrapped up in that, yeah, yeah. Yes. And now, um, your product is a remote office, and I don't... I'm broad-stroking, right?

Broad-stroking. Not exactly Michael Jordan, you know, kind of reverse dunking, uh, in the NBA and, and posterizing. So no one's got a poster of that really awesome message that they sent someone through Roam, you know, up on their wall. So how do you take the lessons of these more visor- uh, 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 it...

I think a lot of times, and, and this is where the crux of my question is coming from, and, and some of this is coming out of the insurance industry too, is we hear lessons from some- from someone like yourself who's worked with a product like the NBA. Sexy, fun, exciting, right? And I think a lot of people, there, there becomes a disconnect or even a self-imposed disconnect between those lessons that you just shared with, with some- with a product like the NBA to their software product or their service product that doesn't seem as sexy as something like the NBA. Yeah. Um, so what's funny about Roam, uh, we get...

And it's been great working with you and, and you, uh, but I think, I think you felt something a lot of, uh, of our users feel in using Roam. And what, what has happened in the handful of years that, that, that we've been doing this, we get... We have raving fans. If you just go to social media, you will see raving, uh, customer- customers of Roam just raving about the software and how much, uh, how more, 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. Uh, a- and, um, 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.

Uh, and so in that sense, there, there are some, there are some parallels. Um, but I also, you know, just like I talked about, um, going back to Canada, uh, 30 years after, um, that's what I'm excited about with Roam. I actually believe this is a generational product. I believe we're gonna look back, you know, 30 years after the advent of Roam and see how it has changed the way people work, how it has changed people's relationship to physical offices and a- around the world. Um, and I honestly believe that we will have built a, a fandom, uh, a, a culture, uh, that is certainly different from the NBA, but 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." Um, and, and the, the, the, the interesting thing about Roam too is it sort of, um, there's this downstream effect. We build this platform. Thousands of companies come onto the platform. They, uh, bring other companies on.

They hire people. And so it's really gratifying to know that the impact that you, you are having on all of these people, not unlike the NBA, right? There are 30 teams and, you know, a hand- 82 games or whatever, and, and but, but the, but the downstream impact of all of that is, is, is powerful. Um, and that's what we're hoping to get to, uh, with Roam. So I think there's some parallels.

Obviously, a lot of differences, uh, too, but that's maybe, maybe how I would think about it. Well, I think you just made an important point, which is, uh, in, in essence, if I'm, if I'm paraphrasing, is essentially we, we are forming the same brand identity, like patches on our shirt with software products, as we 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 podcasts we listen to. Like, all these... It's, it's extended into the products we use. I think for a long time, um, maybe we...

And it may be pre-internet, we didn't associate our, our, our personal, our personal brand to the, to the, the tools we used, right? Like, but today, uh, you're Microsoft- Yeah ... or you're Google. You're OpenAI or you're Claude. You're, you know, like, we look at these things and, 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 Roam or am I Slack or am I Teams, right? And, like, you start to develop, and, and how that tool works and what it means to you, um, kinda 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, the perfect brand connection, right? So the, just in your mind, someone steps up on stage and they said, you know, "When I use Roam, it makes me feel bam," right? Like, this is my brand connection. Yeah.

Yeah. What does that perfect thing look like for you? In the flow. Period. Full stop.

That is what we wanna do here. We wanna make people so productive, build so much culture, make them feel so good that they are in the flow at all... Right? That, that, that is the highest state, um, from a, from a, certainly from a work standpoint, maybe from a human standpoint, and I think, like, that is the... If, if people c- would say Um, when I use Roam, I feel like I, or when I use Roam, 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, 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, uh, and, and if you're a, a, a c- an outside person or a, a candidate that's being interviewed and you come into somebody's Zoom box or versus Roam office, it says a lot about, uh, your, the brand of the company, how you think about, uh, the importance of being in the flow, how you think about growing your, uh, employees because they, uh, can get up to speed easier. They have access to people that's easier.

Um, and so, um, yeah, I think, I think the, the brand thing is, is, is very relevant, uh, from, from a software standpoint. If I, if I'm using, uh, 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 dumbass.

Yeah, usually cheap, like product functionality doesn't matter as much to you. Yeah, yeah. Yeah, yeah. You know, it's, it's weird, and, and, 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. Uh- Yeah, do they get invited to Thanksgiving or d- like do, do they have to sit at a separate table?

Like that's the- 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, blah, and he's only got a Gmail and all this stuff. So, you know, he's, he is the- At least that, not, you know, I mean, it's not like Outlook or it's, they're not on AOL.

Wow, it took me a while to get him off AOL. Okay. Trust me. Yeah, yeah. Okay.

Um, but you know, he's like the classic, like old school, like Luddite guy, you know, the throw your hands up in the air kinda technology, and I just said to him, I was like, you know, so he's, 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 s-" I'm like, "That, you made that decision, right?" And, and the point being, I think far too few leaders, executives, et cetera, spend time thinking about what, like their product, the way you just said it, right? To, to help people get into flow, to be in the flow of their day, to, to facilitate them doing their best work, their deepest work, et cetera.

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- Yeah, yeah ... service. Why don't people wanna buy it? And it's like, well, what does it mean to them? Yeah.

What do you want them to think when they work with you? Like, do, do you have like a thought experiment or just even some simple framework- Yeah ... or reference points? Yep. I have t- two, uh, and it comes back to positioning, right? So here's a very simple statement.

To target audience, Roam is the frame of reference that offers unique selling proposition. To target audience, Roam is the frame of reference that offers unique selling proposition. Reasons why, one, two, three. Tone and manner, one, two, three. So wh- wh- why could you say that, uh, that NBA Canada is the most, uh, entertaining and unique, uh, sports property i-t uh, in the country?

How, wh- why could you say it? Why, what are, what are the, what are the supporting points to that that we're gonna emphasize in everything we do? And then what's the tone and manner that we're gonna do everything in? From designing this T-shirt, to the software, to the in-game experience, is it, uh, responsible? Is it bleeding edge?

Is it afford- Like, I don't know. But, but the, like if you just put that on one piece of paper, everything you do, you can hold that up to, right? How, how, uh, should we-- What do we, what do you think of this homepage? Well, how does it do against our positioning here? What do you think of this commercial?

Um, and so I think that's a, that is a, a technique. The other that I'm, that I'm big on is, um, which is sort of similar, it's net consumer takeaway, right? If I, if I'm running an ad or I p- I do a video, it's exactly what you asked me. It's, it's what, what do I want people to take away from that ad? Like what's the feeling?

What's the quick respon- Like, oh, I just saw that thing. What's the takeaway? What's, what... And it, it helps, everyone gets, you know, all bogged down in what word should I use here, and, and all that's important, but I, I think you also need to take a step back. There's this Harvard Business School, uh, thing, uh, for startups that a balcony and dance floor, like you need to spend a ton of time on the dance floor, right?

Get- g- getting into everything, but then you gotta raise up to the balcony. And so I think that these things help, uh, create framework for balcony raising when we're in the absolute day-to-day, you know, twenty-four/seven, uh, minutia. 'Cause without these exer- And I love that. I love that exercise. Um, there's brand confusion, right? And I think, I think a lot of us, we don't s- when we don't slow n- down enough, guys, and we, and we don't go through these thought experiments like John is describing, um, 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, 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, and I'll give you a, a case in point. Um, my agency that I founded, Rogue Risk, uh, w- 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, a, 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' comp... Like, they literally never positioned themselves as that thing. So even though the person in some cases had 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, 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, it's this kind of...

And then Mark, you know, tell me if I'm wrong here, but like- Knows what you, knows what you do and makes, a- and i- 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 competitors. Yeah. And then you got to, right, and this, I think this is the part and, and, and, you know, here's where, uh, I have a question for you is oftentimes we say something once and we assume everyone heard us.

Right? So, so, you know, just maybe level set for both, for both Rome, maybe some of your past experience with Patch or Confidr, or even like the NBA, like, you gotta... Like, uh, take... I- I'll give you a case in 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, 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 the, 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 it, think about how many times you gotta talk about your product for people to see, right? It just- Yeah.

As, as an executive at AOL, uh, when we, we spun out a 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, like, that, that was my job, uh, just i- in different ways to different people and different media, just keep saying it. It's so important to allo- to align 5,000 people. And, and this idea of wait a... I, I, I said that, right?

How could they not... I mean, uh, particularly in this day and age where, you know, it's the attention economy and, and, and we've got dopamine attention hits all over the place, you t- you have to say things repeatedly. I don't know if there's a particular number, but, um, far more than you want to and far more than you think is necessary. Um, and that is, so that is yes. Uh, whether that's, uh, your advertising, whether it's internal communication, it's any, any form of communication, repetition is your friend.

Yeah. I, I, uh, I was talking to my kids the other day- Let me say that again. Yeah. Repetition is your friend. Yeah.

It was funny. I've, I was, I was, um... So I'm divorced and, uh, you know, my kids, obviously they know, but like, you know, I, I... They know that I, that, you know, I'm dating a woman now or whatever, and, you know, we're talking in general. Something came up on the TV ag- and we were talking about, you know, how do you get women's attention, right?

That's, that's, that's the c- the question that came up from my, uh, 12 and 10-year-old. Um- You look like you, Ryan. Geez, I mean, what, what, what else, what, uh, what do we el- what else do we need here? Not... Well, hopefully they'll be good-looking guys, better looking than me.

But, um, they, I said, "Look," I said, "The easiest way, say her name seven times while you talk to her." Mm. I love it. Just say her name. You just say, you know, "Hi, Sarah, how are you today?

Hey, Sarah, what'd you get on the test? Hey, Sarah, are you going to 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'll most likely get her attention.

Doesn't mean she's gonna say yes to the date, doesn't mean she's gonna like you. But if you say her name, particularly her name, over and over again, right, with s- w- 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 gonna forget you. In fact, you will probably have wedged your- yourself so deeply into her subconscious that she can't help but be interested in you." I said, "And th- 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. Does that... All right, now so I'm gonna play, I'm gonna play podcast host.

Does that translate to, uh, business for you as well, that, that same concept? Yes. Yes. So my, my- Ryan... Does that translate for, uh, to, into business, Ryan Hanley?

Does that... Yeah. It d- it, I'll tell you. So, you know, um, one of the things that I used to teach, and, and the, 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, uh, I built the most efficient and effective inbound sales flow, it's called the Master the Close Flow, um, in history. We were, we were closing 89% of all qualified leads on inbound calls. Um, it was what allowed us to scale so fast, and it was all based in human psychology. And, and one of those psychological principles was, 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, he understands me. He wants to be...

You know, he's showing interest in me," right? And it, and it, it draws you in, and we have to do this, but 1,000 times, 1,000 times over, right, for our ICP, our, our preferred client, right, our preferred customer. Because, like, one social media message, it, it, it's only gonna be seen by this tiny little fraction, and even there, no one's gonna remember it, 'cause it's only once. So even if that, that tiny fraction was the only fraction that saw your message every time out, you still have to hit them five, seven, 10, 11, h- God knows how many times today with how many other distractions they have. So it's like regardless if you're marketing the NBA or you're marketing a software product or you're marketing Roam or you're marketing yourself to the other sex, right?

Right? It's this repetition and, and show of interest that, that wedges you into their brain. And if you're not willing to put in that work, uh, you simply just, you will not stand out. You will not get that brand recognition. And- Yeah ...

I find- Repetition is your friend, as I- Yeah ... have said four or five times already. Yes. So, uh, I wanna be respectful of your time, and this has been incredible. Um, particularly with Roam, uh, I will have links, guys, in the, in the show notes, whether you're watching on YouTube or whatever. Click those links.

You'll be able to go through, schedule a demo. I highly recommend if you have a remote workforce, and, and I'm gonna do just a little bit of sales, John here. Yeah. Go for it. And look, guys, I, in transparency, I told you I am partnered with Roam.

They, um, they are a sponsor of the show, but I wanted to bring John in. Hopefully you took that this was w- way more than just a commercial for Roam. Y- your experience is incredible. We could've 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, um, we, we had this huge move to, to, 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, 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, in all the different tools that I've worked with, uh, there's no tool, there's no platform, um, that I believe marries a fully in-person, the n- the, 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, to interact with each other. Um, you know, not to mention it replaces Calendly, Loom, all these tools in, in one. Um, so it's been an incredible partnership. It's been an incredible tool for my business.

Um, uh, but not just Roam. 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, and what you have going on? I mean, feel free to, uh, I, I'm a reasonable LinkedIn poster, uh, so, uh, follow me on LinkedIn.

Um, also just, just, uh, j- email me at Roam. John, John, J-O-N, @R-O.A-M. I love helping entrepreneurs. I love helping people to the extent that I can. So please, um, uh, reach out and, uh, yeah, let's, uh, let's see if, uh, 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, uh, your flexibility through our power outage of, of the episode as well. So I wish you nothing but the best- ... and we'll talk again in the future. Thanks, brother. Appreciate it.

Thank you.