In short
Fear, uncertainty, and positioning—how to build successful teams and brands, and how those lessons translate from the NBA to Roam (a remote-office software platform).
Guests
Jon Brod (entrepreneur/marketer; co-founder of Roam; previously worked in marketing for the NBA, including launching NBA Canada and expansion franchises such as the Raptors and Grizzlies). Host: Ryan Hanley (runs an insurance agency, Rogue Risk; discusses inbound sales and marketing principles).
Key claims
Success is driven most by the people you surround yourself with; fear never fully goes away—elite performers channel it; discomfort and imposter syndrome can be productive; entrepreneurs must balance certainty (family/financial obligations) with uncertainty (growth); strong positioning requires a clear frame of reference and repeated messaging.
Notable examples
NBA Canada’s “share of time” strategy (snackable clips, hoops in parks, video games, licensed products) and David Stern’s backboard-shattering policy to prevent long-term harm to the sport’s global growth. Roam aims for “flow” and “fandom,” claiming raving fans and downstream ecosystem impact. Rogue Risk example: inquiries for workers’ comp came from businesses that didn’t realize the agency sold it because of weak positioning.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOThe People Behind Success
0:45 to 2:52
Discussing how the right people contribute to success in entrepreneurship.
“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.”
Overcoming Imposter Syndrome
2:52 to 7:20
Exploring the concept of imposter syndrome and how it affects high achievers.
“Because I 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?”
Balancing Certainty and Uncertainty
7:20 to 11:02
Understanding the need for both certainty and uncertainty in entrepreneurial ventures.
“Tony Robbins was on Diary of a CEO and he talked about these five.”
Advice for Aspiring Entrepreneurs
11:02 to 14:05
Encouragement and guidance for those looking to transition from corporate to entrepreneurship.
“We know what we're each good at and sort of how the puzzle fits together.”
Exploring Regrets and Aspirations
14:05 to 16:40
Discover the thought experiment about reflecting on life goals and regrets.
“And the idea is we are not our mind and we are not our body.”
The Entrepreneurial Drive
16:40 to 19:20
Learn how to distinguish between true entrepreneurial desire and job dissatisfaction.
“And you make these two lists and then you marry the two lists together.”
Lessons from Marketing the NBA
19:20 to 22:40
Understand key marketing lessons learned from launching NBA franchises in Canada.
“I will say, just to make the point even further, I was given entrepreneurial opportunities within the NBA.”
Positioning: Sports vs. Entertainment
22:40 to 24:40
Examine the critical differences between sports and entertainment marketing.
“We had planted these seeds and the trees have grown and it's been great.”
Navigating Share of Time in Marketing
24:40 to 28:00
Discover strategies for gaining audience attention in a competitive market.
“I promise you, you will not be disappointed in Rome.”
Engaging the Audience: Marketing Strategies
28:00 to 30:20
Learn how to effectively engage sports audiences through innovative marketing strategies.
“things did you try to get them to say, hey, we know you normally spend 10 hours a week watching hockey.”
Show all 20 chapters
The Impact of Iconic Dunks on NBA Culture
30:20 to 33:00
Discover the cultural significance of iconic dunks in the NBA and their historical context.
“Okay, I'm going to tell you a story that is my favorite David Stern story.”
Balancing Excitement with Responsibility
33:00 to 35:40
Explore the balance between showcasing exciting plays and maintaining the sport's integrity.
“He's got the ball cocked back and it looks like he's just floating in space, right?”
Applying NBA Lessons to Software Development
35:40 to 40:00
Learn how principles from the NBA can inform software product development and community building.
“sure that our rules don't hurt the people who are trying to help us ultimately.”
Creating Brand Connections with Software
40:00 to 42:02
Understand how software products can foster personal brand connections similar to sports teams.
“Thousands of companies come onto the platform.”
Understanding Brand Connection and Flow
42:02 to 46:02
Learn how brand connection shapes company culture and employee experience.
“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.”
Positioning and Product Integration
46:03 to 50:48
Explore strategies for positioning products to enhance customer experience.
“because I see a lot of frustration, a lot of stagnation is just this surface level, I sell, insert widget, insert service.”
The Power of Repetition in Marketing
50:49 to 56:00
Discover why repetition is crucial for brand recognition and customer engagement.
“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 and and makes it unique.”
The Importance of Repetition in Marketing
56:00 to 56:54
Learn why repetition is crucial for effective marketing and brand recognition.
“He wants to be, you know, he's showing interest in me, right?”
Navigating the Hybrid Work Environment
57:36 to 59:04
Explore the evolution of work environments and tools for effective collaboration.
“Hopefully you took that this was way more than just a commercial for Rome.”
Connecting with John Brod
59:04 to 59:40
Find out how to connect with John Brod and leverage his expertise.
“Um, also just, just, uh, email me at Rome, John, J O N at R O dot AM.”
Transcript
Automatic transcript. May contain errors.0:00Who 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 doing these entrepreneurial endeavors with many of the same people over and over. That has made the calculus easier.
0:38Ryan Hanley: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 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.
1:20Ryan Hanley:Now, done a little bit in fitness, done a little bit in tech, et cetera, and obviously media, but, 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. 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 myself and my journey and my story.
2:06So this would be 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 syndrome. Like, I can't imagine I have anything worth, valuable to tell the audience here. but I'm excited for where this goes.
2:26Ryan Hanley:Well, 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 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. Look, I have high expectations for the companies I work at and with and for myself.
3:16And I feel like, yes, I have had a good, interesting career to date. I've had a bunch of success. I've had some failures or not as great success as I would like. And I guess that all leads to sort of 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.
3:55Ryan Hanley: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 – 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. But in the games, you kind of get small, right? And he said – he was honest enough to say that he has fear.
4:35Ryan Hanley:and what I thought in that so we have this conversation about fear 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 shouldn't say I think it's a big misunderstanding myth etc that elite performers people who've achieved success that the next time 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 400 keynotes. I'm just as scared every time I step on stage. I just know how to channel it now.
5:17So do you think it's, it's like, how do
5:20Ryan Hanley: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 so well done there. But you use 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 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 then it's channeling that fear into positivity and some level of confidence.
6:17But yes, 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. By the way, Mindset is an incredible book by Carol Dweck, and we actually make everybody at Rome read it because that's something you need to work on. It's a muscle, and you need to be 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.
7:18Ryan Hanley:Yeah, I was listening to this conversation or 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.
8:00Ryan Hanley: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 is taken care of. I want to make sure I'm taken 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, 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.
8:46Ryan Hanley:how when you're 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 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. It's tough to balance taking on that much uncertainty again, et cetera. So how do you deal with that equation?
9:27I think you're right that a lot of it has to do with age and with dependence and with financial obligations. And so everybody has to sort of do their own calculus. For me,
9:47I had early success, which was great, and that allowed me to continue to do and take risks and do all the things that I've done. But how do I assess the risk?
10:06One is like how big an opportunity is this? like TAM, Total Addressable Market, but just more generally, is this a 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.
10:47So I think that's all part of my – and 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. 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 have certain things you probably need to do, take care of your family, mortgage, whatever it is. and you need to make sure that these risks are the right risk profile for you, right?
11:36Everybody 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 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.
12:00Ryan Hanley: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, guys, so don't take that as a negative, but you got the 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. 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?
12:48Yeah, you know, go do it. Like if you are 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 some of the work, the confidence-building work that will allow you to then take the risk. Do it. It is so damn gratifying. Again, win, lose, or draw. You will learn a ton. I would probably time box it if you've got some financial constraints. Say, I'm going to do this for two years.
13:41I'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 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.
14:05Ryan Hanley: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 question because 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 never read Untethered Soul by Michael Singer, it's a fantastic book, very short, very quick read. And the idea is we are not our mind and we are not our body.
14:49Ryan Hanley: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 it would be uncomfortable to run another mile, well, that's just your body trying to keep you – your body's goal is 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. 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.
15:26Ryan Hanley: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 doing? Okay. Well, we don't have to do this right now. We can get there. We can get there. That's great. I love it. I love it. 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 to learn how to cook. I want to learn how to be an entrepreneur and make money. I want to learn – and I think that making clothes is almost part of that.
16:10I don't know. That's what I've convinced myself. Maybe it's just a kooky habit.
16:15Ryan Hanley:No, I love that and I want to come back to this idea of you have survival instincts in a second. So that's great. OK. 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?
16:53Ryan Hanley: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, you know, 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.
17:35Ryan Hanley: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, or did you know, like if, 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?
18:15Well, 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? 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 it was david stern 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 I can't give you the satisfaction of having built something, taking an idea and building it from the ground and imparting it into the world.
19:14If 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 Grizzlies 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 that's that so for me it was kind of easy because I had the greatest job and the greatest opportunities in the world and I there was still something itch I needed to scratch despite that. And so it was sort of a no brainer.
20:00You have to go do that.
20:02Ryan Hanley: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, two 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 and we could fill hours with what I learned.
20:40For 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 are we targeting with this thing? And how do we, 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?
21:28Is 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 positioning, which any marketer will tell you is critical, was really important and was something I learned at an early age. And I think served us well.
22:11I 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 won a 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 WNBA 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?
22:51Ryan Hanley: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 drill down, right, when you think about 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 go to the movies or I can go whatever.
23:30And so I think just from a share of wallet standpoint, what pool are you playing in? Also, there's the time thing, right? I'm going to go spend an hour doing something. Am I going to play video games?
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24:35Ryan Hanley:That's real money. So click the link in the description below. Get your demo today. I promise you, you will not be disappointed in Rome.
Read the full transcript
24:47Ryan Hanley:So ladies and gentlemen, a first for everything. I just had the circuit breaker for my office pop. I think because it's really cold down here and I have a space heater behind me.
25:03Ryan Hanley: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 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 heater 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.
25:40Ryan Hanley:So I turned 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 what happened. 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 wallet. Share of wallet, yeah. 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 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 are actually in.
26:28Ryan Hanley: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 executive level, I think it's 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. 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 branded, you know, large mega brand coffee?
27:13Ryan Hanley: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.
28:06Ryan Hanley: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 think it's um I mean certainly you put up the product and you hope that 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.
28:52Maybe 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 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 you have to think. And then even licensed products, right? How do we get you to get that NBA, that Raptors or Knicks trash can?
29:33And I'm thinking about, 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 get people to move that share of time more broadly in the way that you would like having planted these smaller seeds ensuring that you're delivering that to them in a way that they want to digest by the way, even working with television broadcasters to make sure that the clips of last night's game are digestible and websites as well uh again 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
30:35Ryan Hanley: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. Do you remember that? Shaquille, I think Shaquille O 'Neal. And Daryl Dawkins. Yeah, Daryl Dawkins.
31:09Ryan Hanley:Hawkins. 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'd 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.
31:57It'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, 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.
32:35Ryan Hanley:That's interesting. I, 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 it was so iconic. And it happens during the dunk contest when the superstars of the NBA would be part of the dunk contest. And, like, you would want to see the dunk contest more than the NBA All-Star game because of these feats that these guys would do, right?
33:25Ryan Hanley:Now that the NBA dunk contest is kind of a joke. 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 haven't seen a dunk in decades where I've been like, that's a poster. That's a poster. I don't know. Okay. Yeah. Maybe not. I'm not as big an NBA fan as I used to be.
34:04Ryan Hanley:Right? But, like, I can tell – I remember, you know, oh, my gosh. I want to say it's not – oh, my gosh. He played for the Hawks. Dominique Wilkins. Dominique Wilkins. 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 windmill dunk it so hard. You know, and those kind of things. And I still think there's iconic dunks, but 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?
34:45Like, oh my God. 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 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 partnership comes into play. The beautiful thing about the NBA is there are, 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 and making sure that our rules don't hurt the people who are trying to help us ultimately.
35:50Ryan Hanley:yeah i think that's really good i think it's really good take these are the calls and these are the ideas that that kind of make or break leaders right that this is this is the the directions that you you have to go 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 Roam. And for, you know, just full transparency, Roam is a partner of mine. I use Roam every single day. It's helped me replace a bunch of tools, big fans of you and your team.
36:28Ryan Hanley: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 just, 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?
37:07Ryan Hanley:Like we self-identify as 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, broad-stroking. Not exactly Michael Jordan kind of reverse dunking in the NBA and posterizing. No one's got a poster of that really awesome message that they sent someone through Rome 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?
37:49because I think a lot of times,
37:52Ryan Hanley: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 NBA, 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 NBA 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 Roam, we get, and it's been great working with you and you, but I think you felt something a lot of our users feel in using Roam.
38:40And what has happened in the handful of years that we've been doing this, 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 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.
39:34I actually believe this is a generational product. I believe we're going to look back 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 around the world. and I honestly believe that we will have built a fandom, a culture 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 and the interesting thing about Rome too is it sort of there's this downstream effect.
40:30We 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 in 82 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.
41:05Ryan Hanley: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 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 extended into the products we use. I think for a long time, maybe we, and maybe pre-internet, we didn't associate our, our, our personal, our personal brand to the, to the tools we used. Right.
41:47Ryan Hanley:Like, but today you're Microsoft or you're Google, you're open AI 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 Rome or am I Slack or am I team? 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.
42:32Ryan Hanley:right? Like this is my brand connection. What does that perfect thing look like for you? In the flow.
42:42Period. 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 is the, if people would say, 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 people hold up a coffee cup that says Starbucks versus have a nice day, it actually says a lot about their personal brand.
43:28And 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.
44:18Ryan Hanley: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. 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 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.
44:48Ryan Hanley:and he's only got a Gmail and all this stuff. So, you know, 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.
45:22Ryan Hanley: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. I'm like, you made that decision, right? And the point being, I think far too few leaders, executives, et cetera, spend time thinking about 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, et cetera.
46:03Is there an exercise that you have and it's probably fairly deep so we could just kind of touch the surface to help leaders who are sitting here think about this type of how their product actually integrates into
46:18Ryan Hanley:people's lives? because I see 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? Do you have 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.
47:02Reasons why? 1, 2, 3. Tone and manner. 1, 2, 3. so why could you say that NBA Canada is the most entertaining and unique sports property in the country? Why could you say why what are what are the 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 uh responsible is it bleeding edge is it afford like i don't know but but like if you just put that on one piece of paper everything you do you can hold that up to right how uh should what do we what do you think of this home page 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 technique the other that i'm that I'm big on is, which is sort of similar, it's net consumer takeaway, right?
48:06If 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? What's what? And it helps everyone gets, you know, all bogged down in what word 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 got to raise up to the balcony.
48:44And so I think that these things help create
48:47Ryan Hanley:framework for balcony raising when we're in the absolute day to day, you know, 24 seven minutiae. 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?
49:33Ryan Hanley:And I'll give you a case in 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.
50:19Ryan Hanley: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, ten 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 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 and and makes it unique.
51:00What 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.
51:09Ryan Hanley:And then you got to, right, and 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 heard us, right? So just maybe level set for both Rome, maybe some of your past experience with Patrick and Fyder, or even like the NBA, like, got it. Like, 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 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?
51:54Ryan Hanley: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 got to talk about your product for people to see, right? They 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 just in different ways to different people in different media just keep saying it it's so important to a lot to align 5 000 people and and this idea of wait i i i said that right how could they not i mean 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.
52:50You 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 form of communication, repetition is your friend. Yeah. I was talking to my kids the other day.
53:15Ryan Hanley:Let me say that again. Repetition is your friend. Yeah, it was funny. I was, I was, so I'm divorced and, you know, my kids, obviously they know, but 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, that's the question that came up from my 12 and 10 year old. You look like you, Ryan. And, geez, I mean, what else do we need here? Hopefully they'll be good-looking guys, better looking than me. But I said, look, I said the easiest way, say her name seven times while you talk to her.
53:58Just say her name.
53:59Ryan Hanley:You just say, you know, hi, Sarah, how are you today? Hey, Sarah, what did you get on the test? Hey, Sarah, you going to 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 get 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? With, 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.
54:34Ryan Hanley: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. It might sound sneaky and bad, but guys, it does work. If you're struggling with women, that does work. It 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? 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.
55:10Ryan Hanley: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.
55:49Ryan Hanley: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.
56:31Ryan Hanley:So even if that tiny fraction was the only fraction that saw your message every time out, you still have to hit them 5, 7, 10, 11, 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? It's this repetition and show of interest 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. Repetition is your friend as I have said four or five times already.
57:10Yes.
57:11Ryan Hanley: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'll be 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 way more than just a commercial for Rome. Your experience is incredible. We could have dove into so many more topics.
57:44Ryan Hanley: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 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 and 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 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.
58:40Ryan Hanley:Not to mention it replaces Calendly, 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, uh, I'm a reasonable LinkedIn poster. Uh, so, uh, follow me on LinkedIn. Um, also just, just, uh, email me at Rome, John, J O N at R O dot AM. I love helping entrepreneurs. I love helping people to the extent that I can.
59:19So 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.
59:29Ryan Hanley: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 nothing but the best, man. We'll talk again in the future. Thanks, brother. Appreciate it. Thank you.
59:48do you
From the publisher
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Jon 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-hanley
Connect with Jon Brod- LinkedIn: https://www.linkedin.com/in/jonbrod/
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