Ryan Barry

Speaker

RM_Ryan Barry_KH === [00:00:00] Welcome to Revenue Mind, where revenue leaders Get Real about mental health. I'm Jolie. Stick around for honest stories, practical insights, and why wellbeing is a real bottom line. Let's dive in. Hey everyone. Welcome to the Revenue Mind Podcast, our podcast Revenue Leaders Talk. All thanks Mental health. I'm Julie, your host, and with us is Ryan. Welcome Ryan. Hi, Julie. Thanks for having me. What's up, everybody listening. Hey. Hey. Thank you. Sorry for the craziness. It was interesting trying to, we had an adventure y'all with Riverside before this, but we are here and we are excited and it's a beautiful thing. And you know what I was thinking about when you're doing your intro, it's always so awkward to remember the intro to your own podcast. Like, like all of a sudden you're like, oh shit, I gotta do this again. Uh, so I have empathy. You crushed, you crushed it. Thank you. So the, just a little context on this podcast, it used to be very structured. It used to be like a lot of just very hard hitting questions, but [00:01:00] now we just kind of riff and we've gotten some really great stuff out of it. So Awesome. Yeah. Yeah. So question for you. What makes you you? Wow. You know, I think I'm the same, the same. I've always been, you know, like what makes me me is somebody who likes to have fun, likes to learn, likes to try new shit, likes to beg for forgiveness. Um, likes to be around people who love me. I like to be around people that I love. And you know, obviously, like as you grow as a human, like. Things change, you know, like you become an adult and you have kids and family and bills and, um, you know, my work life in my real life converged 'cause I just like, like business. I think it's quite interesting. I always have. So that's, that's been kind of cool. But the, the reason I've haven't changed is I have little kids now and I oftentimes am told I'm like the fourth child in this house. And so I dig that about me. So what makes me me to answer it is I'm an adult who has decided not to ever grow up. It's a beautiful thing. Peter, Pam. I'm Peter Pan. I'm Peter Pan. That's exactly right. [00:02:00] I just sort of have like green tights on, you know, I'm wearing a yellow shirt. I guess that's Peter Pan had one of those. Awesome. So you don't think fatherhood has changed you at all? Oh, it has, yeah. I mean, it's changed like it. It's changed the order of operations, right? Like I think, you know, I got married really young, and so it was like, I think about me first and then it's like, oh, I have to think about somebody else. And then you become a father and it's like, oh, actually you're third. Fourth on the pecking order at any given moment. Um, and that's obviously at odds with like humanity and like how we all wake up and are wired. So, no, I think like, and again, like I had kids pretty young in life, so I was pretty immature when I first had my oldest son. I was like really immature and, and you know, now it's like I, you sort of channel yourself through them. You see shit that you do and you're like, oh, I do that. And it shows up a lot when you see a 7-year-old little girl do something that's your biggest flaw. You're like, oh my gosh, I can't believe I do that. So that happens a lot. But yeah, I think like that's, that's been like, that's part of the [00:03:00] adulthood thing. Like you're, you're like responsible for family and like making sure that they're learning good values and trying stuff they love and being happy and all that other good stuff. What do you consider your values that you're teaching your kids? Find what makes you happy. Show up and work hard and don't be an asshole. And that's it. Whatever they do besides those, and I actually got that advice from a friend of mine who's a mentor. He didn't say it in those words, it was just what I took away from some advice I asked him for. I have this classic like. I grew up in the lower middle class and I, I run tech companies, so my kids have Nikes and I'm like, how do I make sure that they have the same moral compass work ethics that was instilled upon me from watching like my dad be a construction worker and grind. And so those are the three things that I've sort of distilled. I'm not projecting anything on them other than like, show up, be kind, do what makes you happy. And so the rest will sort of work itself out so that those are the things we like, hold them accountable for, um, and to honest. They're great. They're great kids. We're we're really lucky. That's awesome. How, if you don't mind me asking you, how old were you when you [00:04:00] got married? I was 26 when I got married. And you feel like you got more mature, obviously? Oh, for sure, yeah. With your kids as you grew, as you not grew up, but as you got older. Yeah. There's always like these societal vectors, right? Like, you know, on one hand I was like pretty advanced in my career at that age. I was one of my, the first of my friends to get married, one of the first of my friends to have kids. And so a lot of ways, like on paper I was like very mature, but I remember like. You know, the, the day my first son came, I thought it was a good idea to like invite friends to have champagne with us at the hospital. Like that's, that's an example of that. Like, whereas I have friends now that are like 40 that are having their first kid and they're like, you know, I just watched them and they just operate with a little bit more discipline and calm, which of course I do now too. But you know, in that time in life I wasn't. So, um, yeah, so it's definitely shout out to my son Declan, for maturing with me. I love that. Okay. You called yourself the fourth child. I thought that was great. What do you, um, what do you mean by don't be an asshole? Um, yeah, that's a good question. [00:05:00] Um, I mean, I, you know, you know it when you see it, right? Like, put your. Put your carriage away at the, or your, your cart away at the supermarket. Open the door for somebody. Pick people up. Don't put them down. Look people in the eyes when you talk to 'em. Say thank you. Like j just like, you know, I, it's funny, we're actually doing an exercise now of like sharpening our values at work and we were debating this phrase that we say sometimes like, be a good human. And it was like, what does that mean? And I was like, struggling with my vocabulary. 'cause I'm like, you just know it when you see it. But I, I think it's, it's about like, you know. Everybody obviously cares about themself, but how do you show up for your family or your community, your friends? And are you being kind like, you could be selfish, but in that moment at least, are you gonna be clear about like what it is and not step over people? You know, like I, I, um, yeah, I guess I don't hope that answered your question, but that's what I mean. Common decency being a human being, common decency. Exactly. Like, you know, I, I mean, I, you know, you're, you know, this too, you work in, in these companies and everybody's from all walks of life and like, [00:06:00] I love people who are unapologetically themselves. I get along with people who are very different than me, who are unapologetically themselves, but it's like those moments when you see somebody backed in a corner and they're acting like, like, really not nice. It's like, oh, nevermind. You know, I, I, that's the part where the common decency for others I think is huge, and that, that allows you to be like. You know, direct, succinct, you know, you can just, you can do a lot of things as a human if you're like actually coming at it from a place of positivity. So I know you mentioned that you came from lower middle class. How do you think that shaped you? Oh, I mean, like. So my mother's, my mother's an immigrant and my dad, you know, they had me when they were 19. So they didn't have shit. They were just figuring it out and I never felt like I didn't have everything I needed. They did an amazing job and, you know, their relationship didn't work out. So like. Kind of classic, like divorced parents, they both got remarried sort of story. I think like the decency, kindness, acceptance thing. I was told by our VP of marketing, Kristen, [00:07:00] that I'm too inclusive. Um, that comes from my mother. Like everybody's always gonna seat at my table. Everybody's always willing to stay. Everybody, anybody can always come and stay with me. Um, which is interesting 'cause my wife is very introverted, so there's always like a gimme a notice, dude. Then I, I think the other thing is just work ethic. Like, I just watched my dad, like just, he's still to this day, works on the highway, you know, he works his ass off. And I remember like pretty young in my career, like all my peers were in their forties, and then I was on an executive team and I was the youngest person on it, and then I was running the executive. And it's like the constant up until maybe seven years ago was like, who's gonna outhustle me? Who's gonna out like, outhustle me and then be willing to unlearn? And I, I think that that was a thing until it wasn't like I still work. I still maintain those values, by the way, but I think I've, with, with some experience, I've learned also like how to use my muscles differently, if that makes sense. Um, but yeah, that's how it shaped me, those two distinct things like that openness and then just, you know, pick up the shovel and, and get it done. Uh, like and work like someone's coming to take it away from you. Yeah, that makes total sense. [00:08:00] I feel like a lot of us are in the camp of, especially in tech, I can always do better. It's a bubble and Yeah. Yep. It's true. I was giving somebody advice the other day. Like you, you could compare yourself to like the 10 companies that everybody compares themselves to, or you could just be clear on your values and like work your business. Um, you know, there's more a hundred million dollar companies than there are decacorns. Like, it's just the way it is. Uh, but it's, you know, and particularly like you go on LinkedIn and it's like this doom scroll. It's become quite a doom squirrel in my opinion. And it's not actually reflecting a lot of market reality. Like an hour and a half ago before, um, I was on our, our podcast, I was reading this like new McKinsey report and it's like, yeah, everybody's trying AI but they haven't like fully leaned in and then you use your LinkedIn feed and it's like you're an idiot. Like it's, you know, it's that that stuff perpetuates that. Like I'm never doing enough. Uh, that you mentioned. Yeah. Yeah. Oh my gosh. I'll see. I'll go on [00:09:00] LinkedIn. Like I feel like four years ago, and I think I've talked this in another podcast like. I remember saving dozens and dozens of, of like playbooks and marketing advice and industry thought leadership. And that's what LinkedIn used to be. And now it's basically, I don't know if it's Instagram, but it's inching on it. Yeah. With like selfies and pictures and traveling and Yeah. Like I get, if you're an influencer, like you want to show part of your life, like I'm sure you have some moments like that, like with your kids and think you like all that good stuff, but when it becomes like, I don't know. I feel like there's really no tactical advice on it anymore, but my feed is like, here's how you, here's I'm a founder and I'm cool. Awesome. It's interesting, I, I try to share, which is probably annoying for my, my colleagues on my marketing team. 'cause like I sh will say something if I have something to say and like, I have this like opinion about. About like companies that keep the customer at the center and hire great people and then like set 'em up to [00:10:00] succeed. And like, so I talk a lot about like, either shit that pisses me off, that gets in the way about that, or like something I'm doing that you know, is, is, you know, at least from the feedback I'm getting from my customers and my employees and shareholders like working. But uh, what I've done to like minimize the sort of dooms of it is I just, I look at LinkedIn in the morning and then at night once, and it's not part of my like. All day flow, which I think is important because you can spend a lot of time on not just to pick on them. You could be on substack all day and achieve the same thing, which is like, oh my God. It's like, really? Everything's quite dire. And then you're, you're spending all this time on trend analysis versus like, what's real? What's actually like, what's going on? Where's the world going? What's happening with your customers? And I was talking about this the other day, like getting out and having a lunch with somebody like you, you can learn a lot more, in my opinion. Like somebody who you admire and respect, you just ask 'em a bunch of questions and it's like, oh. Okay. Have so much energy now. I felt that and now I have some like ideas of what I need to do. Yeah, for sure. And I didn't mean to shit on all founders. There are a [00:11:00] lot of founders that have like a one thing that, that they talk about and they talk Yeah. Really, really well. Like that. I really respect and that that still exists. That I think that at least my feed has become sta with a lot of bullshit. Same. Oh totally. Totally. And like I, I've definitely muted some of it. Like, or a lot of it is like recycled rhetoric. It's at the same point packaged in like 20 different things. Maybe it's 'cause like I process information fast, but I'm like, oh my God, I already saw that post last week. You just changed the headline and now it's the same fucking thing that you already said. And, but it, it, there everybody is, uh, on, you know, for better or worse playing to content algorithms versus trying to be helpful. So, you know, it is what it is. Yeah, totally. What, uh, you mentioned kind of setting a boundary with LinkedIn. What, what other boundaries do you set for yourself? I mean, it's, it's a constant struggle. Like, you know, I, I, I run a technology company that's like at a time when this landscape is shifting. So it's like always on. It's not like it ever, isn't you, like you're, you in a position of leadership, like [00:12:00] you're thinking about at least if you're. At least me, I'll just project for myself. Like you're thinking about the people that work for you and like their families and like, okay, I gotta grow this business enough. We gotta, you know, it's gotta be a good place to work. Thinking about your customers, are they happy? You're thinking about the market, is everything changing? So that's like, that's hard to put in a box. So I, I don't really, I don't like try to like, pretend that that doesn't exist. I try to find spots where, like, my brain is completely disengaged. I spend a lot, so like, I'll leave my phone, uh, somewhere, like for the whole day, or we do this thing on Saturdays where we pretend the WiFi's broken. So that's like one boundary. I, I think the other is like, I don't sit in front of a computer all day, like. I go for a hike, I'll, if I have something that's that I need to think about, I'll like go for a walk, I'll go skiing, whatever it is. And that helps me sort of stay calm and stay, stay really focused. And that's a huge part of my day. Like anybody I work with will tell you that. Like he hates sitting on zooms. 'cause I really do. I think the other things are like just not being in meetings all day. Like I don't like to sit in one-on-ones and like do [00:13:00] daily therapy. I'd rather like. Someone call me when they need something. And, and so as a result, I have more space and time in my day to just be fluid on like, you know, like today I had lunch with my wife, like she just happened to be in the kitchen and I was like, oh, what's up? Let's hang out, let's have lunch. And um, that was, 'cause I had blocked a bunch of hours today to think, and I was doing a lot of thinking and, and like working on some stuff. But I was like, you know what, the exact thing to do right now is, is have lunch with Jill. You know? So, um, so yeah, so those are like some of the boundaries. And I think like my boundaries are probably less formal than. You are expecting me to say like, at this exact time, I'm no longer available. And every day's a little different and I just kind of am fluid with it. And I try to like meaningfully connect with each of my three kids, like once a day at least. Like spend some real time with them, go on trips with them, et cetera. Um, and just be like insanely present. And then in the mornings I po I like drink coffee and stare up the window. So that's like another huge boundary thing for me. Like I do my little doom scroll and then it's like, all right, what's going on in the world in my head? Like, how do I get ready for this day? [00:14:00] It's really funny. I actually do the same thing. I wake up from like five to five 30 is like my sacred. I will sit, I will drink coffee and I will just like, okay, what does today hold? Yeah. Or what a, I love that moment. You know, that was a change for me with COVID. Like when co, before COVID, um, you know, the social thing to do at work is like, let's meet for a coffee. And I was noticing, anyways, you're sitting in this, your house for two straight years, there's nobody meeting you for a damn coffee. So I stopped drinking afternoon coffee. I don't know if it's good or bad, by the way. It was just, it just interesting, like my life changed on that tiny little thing. And so now it's like having a water or whatever. Um. Yeah, I love coffee. I drink coffee. It says like you have the same day and it's like, I don't know if you're clear about what's going on up here. Everything else gets a little easier, so maybe that is the boundary is just being really clear of what I need and like to show up for whoever the hell I need to show up for. 'cause there's a lot of people I need to show up for. Awesome. How do you [00:15:00] think you share up for people? Present. Uh, and by the way, that means I usually show up late because I'm pretty present. Like I, if I'm gonna be with somebody and I take the time to be with somebody, I wanna be there. I wanna be looking in their face and talking to them. And, you know, I think that's, that's important. And like, I've even learned that at home. Like if sometimes if I'm not able to be present, there's no point in sitting in the room half there, you know, it's like better off being like, actually, I gotta go in my office tonight. Like, it's not, I'm not doing anybody a favor. So I, I think, I think that's it. I mean, Al also like, I'm. I think the introvert extrovert spectrum is kind of interesting. Um, I personally really value solitude and having quiet time, but most people who met me are like, oh, this dude's really extroverted. I enjoy talking about to people in cer in the right settings about things that I'm interested in and, and, and interesting people like, I think I find people very interesting. I find like forced networking events, social hours where people are like, what do you do for a living? I found those things very daunting. So like it's balancing for me, like in order to show up and be present, I also need some time to read and [00:16:00] reflect and everything else. But you know, usually when people meet me, they just, they use the word energy. That's like what I've heard people say about me. I have high energy. Um, I think it's always, I think it's usually a compliment, um, but that's usually what I hear about people. Ryan brings a lot of energy everywhere he goes. I remember in, like in my last company, we were probably like a $10 million company, and I showed up to the office and actually Dan, who now uh, works with me at Appcues was like. If you're in a bad mood, the whole company knows it. If you're in a great mood, we all feel it. And I was actually talking to about him last week in San Francisco. He is like, it's 'cause you're like a lot of energy, so it swings with you. I was like, oh, that's a good way to put it. You know? Um, so yeah, I, I think, uh, I think one thing I'll say is like, show up authentically. I'm just gonna like, I'm gonna tell you what's a lot. I'm not gonna, I'm not gonna put spin on shit. Yeah. I think, no, I love that. I think I'm probably the most honest with the people I care the most about. Yeah, because I give a shit. Yeah. Do you ever find your harder on those people too? Or more like, I'll give you an example. When I get home, I [00:17:00] was in San Francisco all last week and I was, I had a really fulfilling intellectual week, but I was done socially and I kind of texted my wife, I'm like, I'm gonna be a puddle when I get home. And like, I don't think I spoke three words Friday night. I was kind of just like, uh, um, but I felt comfortable doing that. Like, I don't, I wonder if, if, if that sort of is linked to what you're saying as well. If you don't mind me asking, do you. Do you happen to have anxiety? Um. I don't, I don't like, I certainly don't have any like, anxiety. Um, no one's ever told me I had anxiety. I get anxious sometimes. You know, like things bubble up, things get anxious. I, I call it like, I worked with a executive coach for a long time, which by the way, for folks listening is just business speak for a therapist. I love Nora Infante to death. I hope she listens to this. I love her so much, but we used to talk about it as a flood. So because you know, I have a DD, like sometimes I'll feel a flood 'cause I think about a lot of stuff all the time. And if I feel a flood and I don't, if I'm not intentional. Like, maybe I'll react versus respond. Um, and so [00:18:00] I've learned in that those flood moments to actually go outside, get outside, go for a walk, whatever. And that helps me with anxiety. 'cause I think everybody on some level has some anxiety. The other thing I do with anxiety is, and actually it's my 7-year-old son who I do this with more than anybody, is I meditate and just a couple breathing exercise and there's this little exercise of like, put all those thoughts in a box. There's nothing you can do about 'em. Put 'em away. And I, that actually helps me quite a bit. I've gotten into that habit. It's not like I'm, I'm not even somebody who like puts on a meditation class necessarily. I just like do some breathing and box stuff if I need to. Um, so yeah, so that's how I grapple with it. But like, you know, the reason I, I dance around, do I have anxiety, is like I marry somebody who has anxiety and it's like a thing that she's actually had to deal with her whole life. I get anxious sometimes, so it's a little bit different. No, I, I, I was just curious, actually have anxiety. Um, so I was, I was curious if you, 'cause you mentioned that your, your battery, quote unquote, gets [00:19:00] drained. It does. That's more of the, the ambivert versus like having actual like knowledge it, but having an actual diagnosis. Yeah, it's, it's like. Yeah, I mean, I got diagnosed with a DH ADHD when I was a kid. I haven't really gone back to get diagnosed for anything. I mean, I, I, I definitely try to handle. I'm try, I'm pretty mindful, like of how I, how I'm doing spiritually, mentally, et cetera, and like listen to that. But the battery metaphor plays, like, I've worked with this lady, Elena, and she's on our marketing team now in two companies and she's always been in customer marketing, so she's in the field a lot. And as a very outward facing executive, I'm in the field a lot and we have like a, we're very similar and we have this built in shorthand, like we gotta go put ourselves on timeout for an hour and like, that's just my signal to like go back. I remember years ago going to, um. Can Lions, which is like the big advertising festival. And you know, on Instagram and on LinkedIn, it's amazing big parties and everything. And it's one of the fakest places I've ever been in my entire life. And I used to say to our [00:20:00] PR guy, like, Hey, can you bring me back to the chalet? And he'd be like, why? I'm like, I need to like take a swim and wash this off before I can get ready for tonight. So like, depending on the, uh, the event. It might just be like it's socially draining or like very mentally draining. If you're like, I don't know if you've ever been to like a multiple day, like intense but fun business meeting that's equally like, oh, my brain's gonna explode. I need a minute to like process what she said, what he didn't say. That weird little energy thing in the corner. Like all that stuff's existing and like, it's hard like in, in the moment to like. You know, process it all. And so, so I, I oftentimes, like, this is one of the, like my leadership things is like, let's let, let's all get a night's sleep and like let this breathe. Because I think the next day you wake up with some clarity after your subconscious motors a little bit. Yeah. And I love that you, from everything we've talked about today, sounds like you really know how to put the brakes and like take a step back and say, okay, this is my state of mind. I'm either gonna, you know, it's time to work tonight, or I'm gonna be really [00:21:00] present or. My battery's at five. Let me, let me take a break. Like, that's, that sounds like you're really self aware, so that's awesome. But honestly, I wasn't, like, I think I said to you earlier in this, this interview, like, I think I got to a pretty great place in life, whatever, like according to society's rubric of what you're supposed to do through just like running through walls and never stopping. And I, I actually like, I, I, I honestly credit this to Nora and, and without her, I don't know that I would've been able to like, have. New muscles now that allow me to do what you just said. So it's actually really a compliment to hear that. 'cause a version of me seven years ago was not like that. I was just running around like crazy nonstop all the time. And you know that obviously you can get to the punchline, you burn out eventually. Like that's what happens. And as you get older and as you have other things that matter more than society's life template, your family, your friends, like you, you can neglect those people. And so it's like, fuck that. I mean, you meet enough people who are 60 and lonely. It's like, [00:22:00] I don't want that life. I'm like, I'm good. Um, you know, so, um, but thank you. 'cause I have done a lot of work on that and it's something that's really important to me. I know we're at times, so where can people find you if they have questions? You can always email meRyan@appcues.com. I put out a biweekly newsletter around modern leadership, which I think a lot of people like If you would like to subscribe and like in all those buzzwords, please do or just like connect with me. 'cause I do share stuff. I try not to use the words AI or whatever. I just try to like talk about humans and how humans build companies. But that's the best place to find me. Awesome. Well, thank you so much, Ryan. Really appreciate it. It was fun to vibe with you, Julie, and thanks everybody for listening to us. We had fun. It was a great day. That's a wrap for Revenue Mind, where we cut the BS and Spotlight Mental Health and Revenue Leadership. I'm Julie. We're reminding you your mindset is your competitive edge. Thanks for listening. See you next [00:23:00] time.