The Leadercast Podcast
The Leadercast Podcast

Episode · 4 years ago

1: Leaders Are People Who Care With Tripp Crosby


It’s hard to define exactly what a leader is.

Some use results to do it; others see the intangibles as most valuable.

Tripp Crosby’s definition of a leader is simpler than all that. To him, leaders are this:

People who care.

Tripp is Director and Founding Principal at Green Tricycle Studios. He’s also regularly the host of Leadercast Live.

We had the privilege of interviewing him as our first guest on The Leadercast Podcast, and we covered everything from his leadership influences to some of his favorite moments at Leadercast Live.

This is the leader cast podcast, helping you be a leader worth following. Hey everyone, and welcome to our very first episode of the leader cast podcast. I'm Haley Panagakus, your host for this episode and content hit manager here at leader cast, and I am thrilled to kickoff leader cast new venture into podcast and even more thrilled to be chatting with their honored host of leader cast live, trip crosby. For are those of you who are familiar with our brand and have been to our past events, you know trip from the stage, but if not, you probably know trip as the taller half of Youtube sketch comedy duo trip and Tyler, who shorts have a masked more than sixty million views around the globe. Behind the camera, trip is director and founding principle of Atlanta based production company Green Tricycle Studios. So, like I mentioned, trip has been our host of leader cast live since two thousand and ten and we're thrilled to have them again this year for our leader cast live two thousand and eighteen event coming up on May fourth at the Infinite Energy Center outside of Atlanta. The trip welcome and thank you so much for coming on the show. We're so excited to have you. Thank you. I'm glad to be here. I can't believe I get to be the first one. I know you're that you're special. Who chose you on purpose? My mom always told me I was special and I've doubted it until today. Oh is sirmed. Well, you should know you're special because you've been hosting leader cast live for eight years now, which is is incredible, and not everyone is aware of the amount of work that it takes to host an event like you just you don't just show up for the day and Rida tell a prompter. You're here with our team through the planning. You're helping us with themes and concepts for the run of the show, your scripting, you're helping come up with videos, and that's just to name a few of the things. So you devote a lot of your time to the event before it's even live, and that's in addition to navigating the run of the show for the day to ensure that it goes smoothly, which is a big job in itself. So it goes without saying we're honored or grateful for your partnership, but I have to ask what keeps you coming back to host leader cast year after year. Well, it's a couple of things. First of all, I love hosting events. It's something that I try to do as often as I can throughout the year for whoever will hire me, because it always lends me the opportunity to get to know new categories of people and I love events and I think it's fun to try and add some levity and some fun and two programs that are otherwise highly informational. But the reason I come back to leader cast specifically is because I feel like I'm always in a room full, I shouldn't say a room full of there's way more people than are attending that are in their room with me, a a a final cast full of people who care. And... thing that is hard to do is define exactly what a leader is. And there's all these people definitions of it, some really smart people that have definitions of what a leader is or how a leader should should lead. But to me I just see it as people who care. They care about their organization, they care about their lives, the people that they have any ability to influence, and that's fun for me. It's and it's always a challenge to figure out how to how to entertain and speak to them and help create a program that actually helps them. Yeah, absolutely, and I think that you know people care and I think that kind of goes into like the servant hearted leadership. I think, oh a lot of the leaders that we have around they're just servants at heart, and you know you are too. You've been doing this year after year and definitely attributes to that. Well, thanks so very varience every time. Yeah. Well, the guy kind of leads me into what I was going to ask you next. Is You've been hosting for so many years. You've met so many different leaders. What would be your favorite moment at a passle? Your guess, live, Gosh bad is a really overwhelming question. They all run together to me. Sometimes it's hard to even remember which speakers or moments were from which years. But I have I have different categories. There's favorite moments that I wasn't involved in and then there's favorite moments that I remember from being on stage. I'll start there. I don't even know what year this was. It was two thousand and ten or eleven. It was a long time ago, but there was a speaker named Steve Uzel, who is a national geographic photographer and I had this interaction with him. It was so incredibly fun and I remember being really nervous about how it would go because we didn't rehearse or really get a chance to even meet each other beforehand, but I showed him slideshow of my favorite photos on stage that I had taken and they were all jokes and it it just worked. I've learned over the years that interacting with speakers on stage is always a gamble, because it doesn't matter how great they are, you never know if they're the kind of people that like to shoot from the hip or like to be fully prepared and read off of a teleprompter, and so I just kind of took a chance that went out there and and we had a lot of fun together. That was one of my favorite moments, and then maybe tied with that would be the year that I interviewed Kane and n Van from Kane's arcade. HMM, I don't know if you remember that moment, but there...

...was this kid who just blew up on social media a few years ago because he built a cardboard arcade, and I could take the time to explain that to be better to just go stearch on Google for Kanes arcade. Watch the video if you don't know what I'm talking about for those who are listening, but he built this cardboard arcade inside of his father's auto mechanic business and eventually there were tens of thousands of people waiting in line to play it because of a guy named Nervon who went and did a documentary about it, and it was such a cool story and and offered a lot of hope and really put a spotlight on the value of creativity and all of those right in my alley. I was a huge fan and I was very inspired by the story before I even knew that they would be at leader cast and then I got to interview them and that was a highlight for me. That's really cool. So you've had, you know, you've had the opportunity to me all of these leaders that lead cast, but you also meet a lot of leaders through your work. So I'm curious who are some of the leaders who have personally impacted in your leadership and what did they teach you? Man Personally and person well, I'm going to have to get really cliche here and I'm going to drop the name of the only other person that I think has also been part of leader asked every year that I have, and that's Andy Stanley. Hmm Yeah, okay. He comes back every year because he's a great leader and he's great at talking about being a great leader. But there was one moment in my life that he impacted me personally that I would like to share. In the early two thousands, I actually took a job at his church as a video director. It was my job to create billy videos to show during preservice for people to laugh at and also get informed about some of the other things going on in the church. HMM, and it was one of the best jobs I've ever had. I'm serious. That organization is run like nothing I've ever seen before. But I had come from a different church and the church that I was at previously also a great church, great team of people, but one of the things that bothered me when I was there was this at the church that I worked at previously was this heightened sense of self importance or like, Hmm, my literally the first task I was given was to create a video series that would teach everyone else how to do church like this church, and I didn't even know how much that bothered me until my very first staff meeting at north point where Andy Stanley got up in front and did his staff meeting thing. I don't even remember all that happened, but I remember one thing specifically that he said he was announcing some sort of new venture and...

...he took the time to remind all of the staff, about three hundred of us, that he didn't necessarily know if what we were doing was the best thing or the right thing, but it was the best he could discern for what he felt led to do with the church and it was worth the risk. I'm butchering. I would never be a quoteum because it was so long ago, but is my first exposure to a leader being so honest about his own limitations and what he might know or might not know and admitting it was all an experiment, and that sort of humility really impacted me and and still does to this day. As a leader I try and not be the person with all the answers but the person with the best questions, and I first saw that modeled by him on his staff and it was a start contrast from where I was before, because, I mean, if you know anything about North Point, they should be the ones making a DVD series about out of the church. They should be the ones like and he had, he probably has the rights to stand up at a staff meeting and say, Hey, we figured some stuff out, let's go tell everyone else how to do it. But that was the opposite of his attitude and that really impacted me. And then he also married my wife and I and gave me some incredible but doesn't hurt. Yeah, lots like you, one of my favorite leaders of all time. Yeah, I mean it goes without saying ours too, and he delivers just such a great message every single year. Me Personally, last year I was watching as an attendee. I wasn't even working at leader cast yet and completely changed my outlook on what I would want to do, and that's why I'm working here now. So yeah, and I think what you share it as a great example of humility. Humility and you know, just goes to show, like leaders, asking the right questions is way more important than thinking you know all the answers. Yeah, and then my second answer would be sort of I don't know if this one would be cliche as much as it is just kind of a given, but my fatherinlaw, Reggie Joyner, who wincidentally helped Andy Start North point but now runs a large nonprofit of his own, has been an inspiration to me for since before I even met his daughter, who I'm not married Tom as someone that really knows how to lead a creative team. I've never seen it done as well as he does it. And I am in a lot of creative meetings that work, with a lot of ad agencies, a lot of big brands, a lot of other nonprofits, and I don't know anyone who knows how to lead the charge creatively with a group of people and I'm still trying to figure out what it is exactly that he does that makes that work. I don't know, but...

I just there's this crazy balance of of leading and being able to inspire a room full of people with ideas, yeah, and giving them freedom to have ideas of their own. I don't know how he does it, but there's just the perfect balance and I'm always trying to model that. I'm always trying to let people, other people in the room when I'm in charge, feel like they have the power to have the right idea, but also be the person that everyone's looking to to for the affirmation of whether or not their idea is the right idea and it's a really it's a hard thing to do and I've I don't even know. I should interview him sometime and find out for myself. We would be interested in seeing that interview. I think creative leaders in particular have a hard time. I mean, all leaders want to inspire their teams and want them to be innovative and think of ideas, but like creative leaders, I mean that is their job. You have to be thinking of new ideas all the time, twenty seven. Yeah, figuring out how to inspire that in your team. I mean it's hard. I'm always in in or sorry. I'm more often than not in a situation where it's too much of one or the other. It's either a yeah, too much of an authoritarian leader in a creative room that is really just looking for a lot of paths on his back for his own ideas and information of his own ideas. I guess it's the same thing, ones a metaphor and one staying it directly. But or I'm in a room with a leader who is who's being more diplomatic and really a facilitator, but just isn't inspiring enough for people to want to be led by. HMM, and I don't think either one really works. I think there's there's something that Reggie has and a few other leaders that I've worked for have and as a creative person in the creative industry, it's it's something I think about and a lot and aspire to. Yeah, yeah, I think you that's very well said. I mean I've I worked on the creative set of things too, and I've dealt with both of those types of leaders, the authoritative and maybe the type of leader that, yeah, hasn't found there their group. There are people, yeah, should be a creative process. They are. There are people, I believe, who have better creative instincts than other people, and I think first we need to just admit that and find out who they are. Like who, on their own or would no matter what team they are, who is just consistently building a portfolio of successful of ideas successfully being executed? Like those people have an instinct and those people need to be the ones in the front of the room. Yeah, and some to you know, I think first, when you... acknowledge that those people exist and then give them authority, and then does people need to learn how to also lead out of humility and also realize that they need they need to be practicing collaboration. You know, we've been talking about creativity is and I think that leads very well to my next question, which I heard that you're working on a movie right now. Is there anything that you can share about that? I can have? It's been a long time since I've publicly updated everyone on my progress. For those that don't know, I posted this really overly dramatic video a little over a year ago about how and why I was going to decide I was going to make a movie and I started vlogging about the process and eventually I stopped vlogging for various reasons and it's been a long time since I've updated. But there is an update. I have written the first draft of the movie and now I'm working on a first draft of another movie, and I think what I've learned is it's probably going to take me a few years to get a script together that I'm excited enough about to go but Bune or someone else's money on the line to produce it. Yeah, but I just finished producing a short film and I've also written about ten more shorts that we will produce over the next year or two among a bunch of comedy sketches, much like what we have been doing for the last five years. So I'm continuing to develop my skills as a writer, director and and also working on a feature link script that I'm just not going to go ask for someone's money until I feel like it's the right script. Right. I mean that's fair, definitely fair, good, exciting, exciting. That that's thank you. The wheels are turning there and that that's great. Yeah, the true for what it brings. So with running your own you know, you run your own business and you've you lead movie sets and I can imagine that it's pretty high stress. Just you know, I have I don't do it, but I imagine that it is. So what are some of your hard earned leadership lessons that you've learned on set and in this very high stress situation? I have learned a number of things by doing doing it all wrong many times. HMM, you're right, and sometimes a set is extremely stressful. Not Always, but more times than not there is a lot more to do than there is time to do, and and a production is such that time equals money. So someone is paying for this production and it's it's probably tens of thousands, if not hundreds of thousands of dollars going into you whatever's happening on this set, and there's a lot of people involved doing a lot of different they're all specializing in something, and then... role is to corral all those people who specialize and, in the amount of time given, create all of the right shots that end up working together to tell the right story or send the right message. And the pressure is high, often because I'm aware that someone else's money is from the line and I know that the buck stops with me as a director, and if something is it right, it's ultimately my fault and I can't blame anyone. So what I've learned from that is all start here. The thing that I've I've put into practice the most, that I've learned the hard way, is to cast vision on set early. It might be like directing one hundred and one, but I've never really I've had to learn to experience. I didn't grow up in the movie industry, I didn't work in it as a low level crew member. I didn't I haven't really shadowed. I've only shoutowed one or two other directors. So maybe this is what they all knew early on. or or maybe this is just something that I do. But usually right before we go everyone gets to work, I corral everyone and try and spend a few minutes casting a vision for what's about to happen, not as much about what the shoot is or what the story is, but more about how I'm going to lead them. And I warned them about my own flaws and I will say hey, everyone, thanks for being here. I'm really grateful for how to how hard everyone is working. I'm probably going to push you in moments harder than you want to be pushed. I'm going to rush you and and not be mindful that you're working as hard as you can and you're trying to do a good job at your job. And I apologize in advance and I give everyone permission to stop me when I'm pushing them too hard, M and I apologize for doing things over and over that seems like we got it already and for rushing them at all the things that I know I'm going to do. And I found that that makes a massive difference and everyone's really in the whole vibe of the day. Because then when I when my personality flaws start to show up. They know that. I know. You know there's nothing worse than being with someone who has a character fall and you know they don't know. Yeah, yeah, you know. They know. There's like a there's more of a connection that happens, more of an ability to just let them, let them off the hook, because they also know I'm I'm open to feedback and I'm I want to, I want to be better in that area. So I cast a lot of vision about what it's going to be like to work for me. And the second thing I do is I offer lots of positive feedback. On a production set, it's probably not much...

...different than in any work environment where someone above you is going to keep trying to make sure that you're doing a better, better job at what you're doing. And, no matter what, I think that normally feels like negative feedback to people. So if I say hey, let's do that shot again, but let's do it this way, or I go to an actor and I say hey, try this, no matter what my motivation is, the more I do that, I think, the more they naturally feel like they're not doing a good job because you're not doing it right. So I make sure I go out of my way enough to as much as I can to give positive affirmation so that they know that all the areas in which they are doing a good job. That's so cliche, but it really makes a difference in my world. Huh. Yeah, I love going back to the first thing you saw at up. I love that. You know, it's a great example of the importance of transparency. You know you're transparent about what you know, your flaws and what you might do and what they should be expecting of you, but you also lay forth your expectations and set your vision, and I mean those are all qualities that we talked about here at leader cast. I know I just I'd something I believe in very strong it's part of my own life's mission just to be the most transparent person I can possibly be, and I know I could probably gain more respect in some areas of my life if I just faked it a little more in some ways. Yeah, but I just I don't believe the net gain is is there. I think I noticed in the long run there's much more benefit to being open and honest about my own shortcomings or or just areas of where I have a lack of expertise. I just I find that in the long run people respect me more and there's more of a connection with those people in the long run. Yeah, definitely. So, speaking of people and your years serving leader cast and with the people you work with every day, I mean you work with a lot of leaders. So what are some of the biggest challenges that you've seen leaders facing today? Maybe there can be very related to everything else I've said. Okay, I think that there's a lack of transparency. I think tribalism is a major enemy of our culture right now. I think people are fighting and leaders are fighting to protect their tribe instead of fighting to protect whatever might be best or true. So I know too many people that would never consider a...

Republican perspective or democratic a Democrat perspective, no matter what information they are presented with. They have they have decided this is their tribe and the same way they've decided they are a Georgia bulldog fan or a Pittsburgh pirates fan. They it's their tribe. I see this in politics, I see it in religion, I see it in just people being part of a brand and I think that really gets in the way of leadership because it's some point a leader can't be truly honest and open to new information because they're two committed to their tribe. Yeah, so me that gets in the way of the thing I'm I'm most for, which is authenticity and and humility. HMM. I love that perspective that you bring of tribe, because when I think of tribe, I mean I've find your tribe and, you know, find those people that you, you know, really connect with and I think for leaders, you know you want you want to lead your tribe in the best way, but bringing that perspective of like having a tribe and you have to be very careful of how you lead your tribe and tribe can be a negative thing. I like that perspective that you bring up. There's nothing wrong with the tribe, no, he means, but tribalism, I think there is a little different. I think, yeah, it's it's being really what it is is the fear of the unknown. I mean you don't have to look very hard in our culture to see people twisting data to affirm whatever it is they want to believe. People are so afraid of being wrong about something that they always thought was true. But that's not how we progress, we progress through having great questions, not great answers. You know, I heard a quote from someone recently who said he's a theoretical physicist named Richard Stayman, and he said I'd rather have questions I can't answer than answers I can't question. HMM, and nothing scares me more about our future than then. And then when we stop questioning everything, I think. I think the only reason we have things like medicine, or we have, you know, the only reason where in a culture that doesn't embrace slaver anymore, slavery anymore, or that that is that's trying really hard to make sure that women have equal privileges, or it's because we've questioned things, because someone has at some point gone way. Is this right? Is this right? And I think that the leaders that inspire me the most are the ones that are willing to question not only their their practices,...

...but also themselves. Yeah, yeah, everything you're saying reminds me, and some of our viewers may remember if you attended leader cast women in October last year, reminds me of Dr Bernice King. She kind of she spoke on that and she said, you know, leaders need to be the answer to a question now. So we need to be asking the right questions and not just providing answers so that we can be that answer. So I love that. I think that's great and it's opposite of what of a lot of what I see. I see a lot of leaders. Who are they? They're not. They want they want to have the answers. I think that's what makes them there's they're the ones are the answers, but I think the leaders are the ones that have the best questions. Yeah, for sure, and I think we need to just decide it's okay to be honest about what we don't know. Yeah, and that's something I care a lot about right now. Yeah, I can tell about that's great. I think leaders need to be caring a lot about that right now, for sure. Yeah, that's so. We've talked a lot about we've talked about leaders to challenge, we've talked about managing highstress situations. But, as as we all know, leadership is a lot more than that. It's also rewarding. So what's the greatest joy of leadership to you? Maybe there's an example of you know, a success or, you know really make a main impact on someone. What's your greatest joy of leadership. Two things bring me great joy. One is when I speak an idea executed and brought into fruition, whether a great example would be someone has an idea for a comedy sketch or a short film and then a bunch of people have to come together to make it happen and then it ends up being even better than what we thought when we were just talking about the idea. That that is so unexplicably satisfying. It's something. I'm addicted to it, it's it's amazing. And the other thing that is equal to or maybe even surpasses and said it and as far as being satisfying or bringing joy to my life, is being someone else's experience enhanced. You know, I here's a here's an interesting story. I there's a guy I'm friends with. His names Miller Moubley and he's in he's a fantastic photographer. But what it when I say fantastic photographer, that doesn't mean anything that anyone because everyone has at least one or two friends who have who are a fantastic for photographer. But I'm telling you, if you go to Miller mobleycom or you google...

...him, you're going to go. Uh Okay, this is different. He is a portrait photographer and you can't name an alist, celebrity or politicianer coach that he hasn't done a staple photography of, from like the Obama's to to just I don't like it, Taylor swift to you can't name a big time celebrity or influencer who he hasn't taken a photograph that you've probably seen on the cover magazine. And he even he's even. I remember the day early in his career when he texted me and let me know that he made the cover of Time magazine one of his photos. Wow, this guy was a kid, a sixteen year old kid, who I was in charge of at a summer camp when I was in my early S. his stepmom called me and said, Hey, I know you lead the video crew at the summer camp and I know that you're supposed to be in college to come participate in that program, but I have a sixteen year old kid who's attended the camp as a camper for many years and we've donated a lot of money at this camp. I'm just wondering, could you ever make an exception for my kid, because he's really interested in video and photography, and so I said sure whatever. He came out. We developed this amazing bond. We became friends, even though we were different ages, and I was really his leader. By all practical purposes, I would I consider them a friend and I taught him how to use a camera. But here's a camera, here's how it works, here's the shutter, here's the IRS, and I try to answer all the questions I could and I remember him disappearing for hours of the time and he would come back with like a hundred and eighty photos of a gumball machine from every angle he could find and and he obsessed over it and I tried to just pour him, having no idea what sort of what's what was to come like, what what the fruit of that would be. And here he is now, like one of the most successful photographers out there who have a passion for what he does, and I think he'll he'll be remembered for a long time for his work. And that's just one example. That's kind of an extreme example, but I feel like all the time I'm being presented with opportunities to look at someone who I could help in some way by offering them expertise or an opportunity to just be on set and learn to just encouraging them in some way, and that's that's ultimately what I find satisfaction then. Yeah, I want everyone that has a chance to work for me to be way ahead of me when they're my age or just eventually. That would be more satisfying to me than just always being the one out front or in charge. Yeah, really, what I love most about that story is you you might not know, like what impact you're going to have on someone like so far down the road, like just this little nugget of time, that something that might be so simple to you. I mean that directly changed his whole life.

So I think that's something for that leaders should keep in perspective. I think that's a great, great story. Thanks so well, trip, you know, thank you so much for speaking with us today. You've provided so much, so much leadership wisdom, and I know that a listeners will walk away with a lot of a lot of thoughts and things to think about in great perspectives. And again, we're so excited to have you host again this year, your eighth year. Do you want to share with their listeners what you're looking for to the most about this year's that your cast live. I'm looking forward to being surprised. I always am. There's always some nugget of truth or inspiration that happens at these events that I didn't see coming, and so that's what I look forward to. I know that's really vague. Yeah, but I just think that I've learned to approach this event with an open mind, M and with no without looking for anything specific. I just want to show up and I want to be engaged and I want to listen to speakers and I want to do my best to build a bond with the audience and help them get from thing to thing and hopefully make them laugh. HMM, and just be surprised. Yeah. Well, we're excited to not only surprise you, but surprise everyone who attends and have everyone walk away with a lot of incredible insights and wisdom. Yeah, I'm I'm I'm honored to be back. I'll be there as long as you'll have me. Yeah. Well, we're honored and thank you so much again for joining us today. We're honored and blast to have you as a leader cast partner. So I also want to send a huge thank you to all of our listeners for tuning into our podcast today. You can. Please go ahead and share and subscribe so you don't miss an episode, and please join us again in May for our second episode of a leader cast podcast and leaders. Thank you for all you do to help us in our mission to fill the world with leaders worth following. We would not be here without you. Be sure to check out trip and Tyler on Youtube. You can also follow a trip on instagram at trip crosby. That's two piece trip crosby. Please come see trip and see us that. Leader casts live on May fourth in Atlanta or at a host site near you. Thanks for tuning in to the leader cast podcast. To ensure that you never miss an episode, subscribe to the show in your favorite podcast player.

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