S2E4: Courageous Ideas: Transforming Your Business with Ryan Berman

Seth Waters (Co-Host): Hi, everybody. Welcome to the Purposeful Prosperity Podcast. I'm Seth Waters, and I'm here with Jack Smith. And you know, Jack, he is an entrepreneur, founder, investor, and world-changer. Jack, excited to be with you today.

Jack Smith (Host): I'm excited to be here, too.

Seth Waters (Co-Host): Yeah, we have a really great conversation today with Ryan Berman. Excited to have that.

Jack Smith (Host): Absolutely. A longtime friend of mine, a fellow Hooper, and a serial entrepreneur and author, and a motivational speaker, man. I love to hear him talk about courage.

Seth Waters (Co-Host): Yeah, looking forward to this. One of the things that Ryan said during your conversation is he talked about how if you don't know what you stand for, you don't know when to take a stand. Jack, how do purposeful leaders get clear about what they stand for and how important is it for companies to know what they stand for?

Jack Smith (Host): Well, without clarity, you can't lead through objectives, right? So if you don't know what to ask for, your people, your staff, your team doesn't know what to provide. It also tells you when to take a stand on a particular subject matter, right? As companies, as businesses, understanding what we're trying to accomplish in the big hairy-ass goals is so critical and the more you can get clear about that as a company and then integrating that into your external marketing, so your customers understand your why and your people understand your why, and now you have a resonation of it. It is so important that we just came back from an offsite, we actually hired a third party to come help facilitate some of these conversations for Fortuna. Because with growth and development and all these things, that's really what comes of it is you have a redefinition and a renormalization of success. And without that clarity of why and purpose, you don't know when to take a stand. And I thought that was really beautiful.

Seth Waters (Co-Host): That's really good. You know, one of the other things that Ryan talked about, Jack, was he said, you can't get to the solution without getting through the fear. He said, let's address the fear. How important is it for purposeful leaders to address fear?

Jack Smith (Host): Well, I think the name of his company is called Courageous, right? And so I think what he means by first through fear is courage doesn't happen without there being some potential risk, some afraid of loss or discomfort, right? So understanding that there's fear, normalizing, accepting it, nothing courageous happens without having digested it first through fear. And as leaders, if we digest it through fear, we take that fear away from our staff and our team, and we give them the freedom to fail and succeed in an iterative fashion, right? Because success is a period of efforts. It's not happening one after another. You try, you fail, you try, you fail, you try again, and eventually you succeed. And I think as leaders, when we can take that fear away, we give the space for the courageous actions of our leaders to grow.

Seth Waters (Co-Host): That's really good. Well, without anything further, let's jump right into our conversation with Ryan Berman.

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Jack Smith (Host): Well, thank you, everybody. Welcome to Purposeful Prosperity. I am Jack Smith, your host, and I'm excited today. I've got my friend and fellow basketball junkie, Ryan Berman, with me. He's a marketing extraordinaire, but he's been on a really courageous journey over the last 10 years since we've known each other. And he's here to tell us a little bit about his journey of founding the Courageous brand. Welcome today.

Ryan Berman (Guest): Hey, man. How are you?

Jack Smith (Host): Great to see you.

Ryan Berman (Guest): How's the jumper?

Jack Smith (Host): It’s a little rusty but I still try to get it to run every couple of days. So, you know, I can't quit it, but I can't get great at it either. So, you know, just like golf. How are you man?

Ryan Berman (Guest): I'm great. It's great to be on the show. I'm, you know, it's funny you talk about courage and then you see your friends go out and start new things and you're living it too. It's, it's noticeable for me to see your shift as well. So, much love and major props from San Diego.

Jack Smith (Host): Well, I gotta tell you, I learned it from watching you. Your journey from the fish tank to idea brand, to now, Courageous. I watched it, you know, literally from the sidelines to beside you and, you know, and you've kind of been my marketing buddy throughout all of this as I'm figuring out my journey. So can you tell us a little bit about, you know, from the days we used to shoot jumpers to today?

Ryan Berman (Guest): Yeah, it is a journey and it's been a journey and, um, to think back to, you know, it's probably started with, my shift started with me writing my book, which was called Return on Courage, which was a, a three-year listening lap. You know, it was, I had the ability to get quiet and listen to what now I call the brave, the bullish, and the brainiacs. And I got to tour the country and interview all these people. And to be honest, Jack, like at the time, I thought this was the beginning of a business plan for my last business, which was called i.d.e.a. We always were about, you know, we would say, you know, courageous ideas are the only ones that matter. And the more I sat with these leaders, the more they turned into mentors for me. And what I needed to pick up from that journey pretty much gave me the confidence and courage to shift from really, ad agency life to what I would call now a courageous business.

And if you think about your business, you think about your team, there's probably somewhere where you're stuck, where you're scared, where you're stale or you're spinning. Or maybe the team is playing it safe. And what I learned from sitting with the leaders at Apple, and Google, and Amazon gave me a process to teaching companies how to basically get unstuck. And whether that's a people issue or a narrative issue or some combination of the two, I always like to say it's hard to be courageous when you're cloudy. And going back to our first world, it was clear to me now that there was something about my last life that I wasn't fully fulfilled in. At i.d.e.a. we were about 90 people and it took me about a decade to get there of like six days a week and you're sitting in this office and you've hired well and like something isn't sitting well with me. I'm like, is this it? Is this how I'm supposed to feel? And like I said, I go on the book writing journey and one of my interviews was with a woman named Loretta Hidalgo She is a founding astronaut at Virgin. And she said, “I takes you 40 years to figure out who you are, and  the next 40 to be that person.” And that was the moment where I was like, all right, maybe I'm stuck, scared, or spinning. And I started to work on my what's next, which is now what we call Courageous.

Jack Smith (Host): I love it. So tell us a little bit about launching it, right? So you wrote the book and then you launched the Courageous Podcast. So you've shifted from more of a marketer to really now you're a storyteller slash inspirational speaker, right? Like you're a motivator now.

Ryan Berman (Guest): Yeah, I would say there's three elements of the business. There's courageous leadership. The more I do this and the more leaders I talk to, you realize it can get lonely out there.

Jack Smith (Host): Very lonely.

Ryan Berman (Guest): And in some ways you just want to be their ally or their friend. And it's sort of sad, like the higher up you get in an organization, the more isolated you could feel. So on the leadership side, it starts with that world. There's keynotes, there's off-sites, there's coaching and there's workshops that help bring a leader or a team along. Then there's the courageous consulting part of our business where our team is pretty much rolling up our sleeves. I say we're a special forces that helps you figure out your special and then bring to life that special. where does the business actually have to pivot? So we're literally in there with you, coming up with what those narratives are, and then we're helping you operationalize those narratives, keeping you consistent on that message and getting it, sort of going through the veins of the organization and then taking it to the outside world. And then the third piece, which I don't know if I saw coming was, I call it courageous entertainment for lack of a better term, but that's the Courageous Podcast. I've got my weekly dose of courage that goes out, which you can follow on LinkedIn. And it's just putting out a drip of content. If I've learned anything from the last five years of doing this is that we need to see it over and over again. I like to say repeaters make believers, right? So we have to be consistent with the language. You got to put it out every week. You just never know when your content is going to collide with someone that needs it. Someone might hear from me 48 weeks a year and then something happens that week at work and suddenly a dose of courage is like, “Oh, Oh yeah, I got to slow it down or I have to stand strong.” I always say if you don't know what you stand for, you never know when to take a stand. And maybe there's something in one of the doses that's coming your way that gives you what you need to pivot.

Jack Smith (Host): I love that. You know when to take a stand, but if you don't know what you stand for, you don't win. I really appreciate that. That's very cool. Thank you. Sorry, you say you get paid to tell the truth and you know, help with leadership seems keep in check. Can you tell me a little bit more about that? Help me kind of understand that. Like, what it means. What does that mean to you guys?

Ryan Berman (Guest): Sometimes a company knows exactly what they need to do. The leader knows what they need to do and for some reason, it's not landing with the team. The gap is too big and often we're brought in as a first inning to basically be a permission slip for a hard conversation about change and I think there's only two ways that cultures go. One, it's a courageous culture and you can feel that energy, right? People aren't afraid to make little mistakes or to speak their minds. They're in a safe enough environment where they can do that. And then there's the other culture where you walk around the office and you can't see anyone's necks and you can hear a pin drop in the room. It's a bit of a choose-your-own adventure, right? Courage breeds courage, but fear also breeds fear. And when you see a courageous culture and you see them, it might be messy, but they have permission to try. I should have worn it. I have another t-shirt. I'm not a fan of “Fake it till you make it.” I think that's really bad advice. I like “Mistake it till you make it,” which I make these t-shirts. I think it's that. I think, “Hey, you know, you have permission to make, to try things out and make, if you're going to make a mistake, make it small, but let's learn from that. And let's keep iterating, keep moving off of that. But let's have fun as we go along here. And I think that is, that is what I mean by becoming that permission slip that gives a culture or a leader the ability to go, you know what? You're safe here to take risks, which is an interesting juxtaposition. And so when we get brought in often, it's for that reason. It's, all right, what's the conversation we're not having that we absolutely need to have right now? And I think we're all time-starved, so that conversation needs to happen. That's what I mean by a first-inning person.

Jack Smith (Host): I love it, right? You set the table for those courageous conversations that you have to have, because that's where growth happens, right? Growth doesn't happen in your comfort zone. That's why it's so comfy. You know, you had to get outside of that comfort zone and these conversations. And I think your facilitation is really how you take that first step into the larger world.

Ryan Berman (Guest): We like to say we're fear fighters. So it's like, imagine this coming into an organization and I'm not going to pretend to understand your business like you, but what I can do is taunt the organization for the largest fears. There's a famous proverb that fear and courage are kin, that you actually can't get to the courageous choice without channeling it first through fear. So let's address where the fear is. Is it a spinning problem? Is there some conversation, like I said, that needs to happen before we move on to the next challenge? It's like Monopoly. We can't pass “Go” here on this problem until we address that first big problem, and then okay, now what's the next big fear after that? And then the next fear after that. So it's a fun business to be in because you're compensated to first look for the fear. Don't suppress it, but address it.

Jack Smith (Host): Don't suppress it, but address it. I like that. Don't suppress it, but address it. Wow. So I love your whole message around Courageous and we embrace it here at Fortuna all the time. You know, I talk a lot about embracing failure and, you know, and we just do stuff and I love the way you said “Mistake it till you make it.” So I definitely, I'd like an order of 25 of those t-shirts if you could please be spectacular. We can be your walking billboard for that. Well, that's an awesome way you've kind of taken your skillset and learn to be the storyteller and that inspiration. How are you tying that to prosperity for others, right? So you're the, you're the fear fighter. You're the one who comes in and helps them get to those crucial conversations and to have them raw. How do you take that to the next level and kind of make the impact to the communities?

Ryan Berman (Guest): Yeah, I think when it comes to helping a business figure out who they are, if you look at any trend right now, it's pretty clear the world is moving more towards a values-based society, meaning the next generation, if you don't stand for something, they're out. They're not going to just buy your product just because it tastes good. There now has to be an extra element. This next generation wears their values on their sleeves and they vote with their dollars. So a lot of our work is helping companies figure out not just their why, but what we say is their rally cry and their why. Why does your team want to stick around for this story, right? Am I willing to hunker down and fight for you and fight for this story? You know, everybody at Patagonia, they're trying to save our planet here. You know exactly what you're getting when you sign up for Patagonia. However, at SpaceX, it's the opposite. It's life on another planet. That's their audacious rally cry and their why. So whether you're trying to create life on another planet or save this planet, think about what you're really passionate about, which is also emotional territory. That is the type of story that we're looking to find that are authentic inside companies and then operationalize those stories.

When you finally land on that, it's not just about shareholder return, right? It's about doing good in the world. You're going to find your tribe of people at both inside your company that want to stick around. And then outside,  in the outside world, that's going to be your future customer. And that's your word of mouth. And suddenly people are talking about your business. So one of the reasons why I left advertising as I knew it before was I was getting calls to tell the world a story on the outside that may have been inauthentic to the culture. And now. It's, Hey, there's plenty of words out there. Like, have we actually landed on a narrative that excites your team on the inside? And once we have that on lockdown, we can take that story to the outside world. Those are the type of companies that we want to work with. The companies that are willing to commit to a true rally cry in their why. And then how do we activate that both inside and outside of the organization?

Jack Smith (Host): I dig it. Operationalizing authenticity, right? That is really, really rad. And that is going to be the next generation of businesses that thrive in the world. Um, cause you're absolutely right. They, everybody today votes with their dollar and their values are right up front. And they're not shy about them anymore, right? You know, when we were growing up, everybody was just kind of vanilla. You didn't really express too many opinions. You just kind of stay in the middle and everybody else is like, “Hey, no, this is how I live now.”

Ryan Berman (Guest): Well, I also think it's, if I'm a leader and I'm listening to this podcast and Jack, like you, you've gone through this shift yourself. I think there's something fascinating about the way we commute to work. So imagine for a second, you know, again, I know offices aren't what they used to be, but humor me for a minute, right? Like I'm at, imagine for a second, you're driving to work. You've just said goodbye to your spouse or your kids. or you flicked off the TV and you're on your way in. And there's like somewhere on that commute that you leave home version of you at home and business version of you starts to show up. And business version of you is a little stiffer, we'll call it. You have to be a little more intentional, a little more thoughtful about what you say and how you say it. And God forbid you're in a room with 10 people and you don't come off sounding smart to that room. And so you go and you do your things and it's an exhaustive eight-hour, nine-hour day. And then you get back in your car. And again, as you're driving, oh, maybe you took that last call in the car, but as you're driving home and you hang up, there's another imaginary line where you defrost away back into you as you know you really are at home version of yourself. And the problem is, that's the person that we're all trying to land with and connect with.

So when you say operationalize authenticity, or I like to say operationalize keeping it real, it's like, hey, what worked at you at home? Because whatever that is, is the emotional stuff that actually will work at you with work, or will work at you in the market. Again, if you run into an idea in the wild, how emotional is it? Does it really have, what it needs to short-circuit your behavior? And when you're not there as the leader, pointing to the idea in the market doesn't really have what it takes to stand out on its own. So this is the challenge for all of us. It's like, actually, when you see something that makes you smile, that's good in the world, that has prosperity, that's also the thing that breaks through this media-obese world that we live in and sticks with you in that you remember that you want to play with and that you're curious about that you talk about. And then you try it for the first time. And so one of my quests with leaders is to, is like, Hey, like don't cross back over. Don't cross that imaginary line from “home you”. In that work, you'd like bring “home you” to work and just be that person. Cause that's, what's going to work in real life in the wild.

Jack Smith (Host): Right. Just be you. There doesn't need to be a “work you” anymore.

Ryan Berman (Guest): Correct.

Jack Smith (Host): And I think we as leaders have the opportunity to create that space where it's okay to be vulnerable. And we demonstrate that by saying, “Hey, you know, I'm having a rough day or I'm not my best self.” And we start to emulate that for our people. And then it shadows on down.

Ryan Berman (Guest): And it starts with the leader, right?

Jack Smith (Host): Absolutely.

Ryan Berman (Guest): So the leader creates space to go, “Hey, I have an R day.” There were mirrors, you know, or, “Hey, we're having a great day as a company.” Here's why. Last week, much harder than this week. Are you guys feeling that? Right. So as mirrors, we're sharing how we're feeling. And as a leader, if I don't share what life is like at a home, your culture will probably mirror that.

Jack Smith (Host): Right. And, and we say family first around here all the time. And we really mean that, you know, when life comes up and, but that's something that we've demonstrated for 10 years, and our leaders do that for their staff. I love it. Well, thank you very much, Ryan. Is there anything that our listeners can help move your message forward, either Courageous brands, if you've inspired them today, is there any way they can support you or maybe bring you guys into their organization to help with some courageous change?

Ryan Berman (Guest): Well, where I would start is, pick up the book. If you want to be a little bit more courageous or you want your team or staff or family to be more courageous, check out Return on Courage, which you can pick up at Amazon or returnoncourage.com. I think what you'll see is that courageous, being courageous, it's not a, it's not a careless act. It's not an impulsive act. It's a calculated act that can be learned, thinking that like a muscle and the book sort of takes you on a journey as to why your company absolutely needs to figure out a way to unlock this in its organization. And then how do you actually do it in a way that doesn't kill the company, but actually enhances it so you can move forward and thrive.

Jack Smith (Host): I love it. Well, thank you for sharing your courage with us a little bit today and hopefully you inspired our listeners. Thanks so much for your time.

Ryan Berman (Guest): Thanks, Jack. Appreciate you. Keep going, man.

Jack Smith (Host): Good stuff. Well, keep hustling, brother. You take care.

And thank you guys for listening to Purposeful Prosperity. Tune in next week where I'll introduce you to another amazing entrepreneur doing great things in the world. Until then, please like, follow, and share, and keep doing good in the world. Thanks for listening.