His Worst Coach Made Him Into a Great Leader with Damon Lembi, CEO at LearnIt

Today, we're talking to Damon Lembi, CEO at LearnIt, about how his worst coach made him into a great leader. Thank you to DigitalOcean for sponsoring this episode. For a simple cloud and powerful AI that's built to scale, visit digitalocean.com or just click the link in the show notes. You're listening to Joel Beasley, Modern CTO.

And basically, the way I got connected to you was I interviewed Rob, who I immediately liked and had a lot of respect for. And then he's like, "Hey, you've got to talk to Damon." And I said, "Okay, we'll talk to Damon."

And you've got a book, The Learn It All Leader. It's like a play on "know it all." You've got a bunch of stuff. Why don't you tell me a little bit about what you have going on right now?

So I got a book, The Learn It All Leader, but what I've been doing is I've been running a live learning platform for about 30 years. And essentially what that is is we do B2B training where companies turn to us if they need to upskill managers who don't have the right skill set, or they're trying to work through communication challenges. But we also, for 30 years, our bread and butter used to be around Office 365 training, how to implement and roll out Office 365 or whatever before, and getting people involved in adoption. So we did that for quite a while. We still do. I mean, it's changing a little bit with AI and Copilot. But essentially, my book is just about—I used to be a baseball player, and my only job I've ever had was LearnIt. And what happened was when my baseball career came to an end at 22, I was kind of dealing with an identity crisis. Like, what do I do now? I don't know if my skills are transferable or not.

And so because of that, I took a job as a receptionist at one of my family's companies and kind of went all in when it came to learning and being curious and working with mentors and everything. And so I ended up writing my book, telling a story about my journey and others that I've worked with or come across over the years.

Awesome. So existential identity crisis after baseball career wrapped up, and you're like, "What do I do now?" Then you just said, "Hey, I'm just gonna start from the ground up, and I'm gonna figure this out. I'm gonna be curious. I'm gonna learn it, learn everything I can learn." And you started in a company. And then tell me about how you went from that receptionist job to owning your own business.

Yeah. And prior to the identity crisis, one of the things that people like a lot—I talk about in my book because I have a framework for overcoming impostor syndrome, which I kind of struggled with in school as well. And I started out as a receptionist at this small little startup. My family had a really big real estate company, and I wasn't ready to go into that or sure I could even do anything. So I started as a receptionist, rolled up my sleeves, jumped in, started teaching classes like Excel and PowerPoint and Word. You know, kind of just learning all the different roles and got into sales and even helped out the IT work around. You know, back then everything was local and everything. And five years into it—and this is right around 2000, and I'm in San Francisco, which was the heart of the dot-com days, so everything was just blowing up. The guy wasn't working out. They were looking for somebody else. I presented to the board like everybody else, and I said, "Hey, look, I've done this, this, and this. I'd love a shot." And so they gave me a shot, and I got a little over my skis, as you like to say, because everything was so great. And we overexpanded and had some great learning lessons of what not to do. But we overcame that as a team, as an organization, and we've overcome two or three economic downturns. Lot of learning lessons through there, and here we are now again. And we've kind of pivoted from being just a computer training company to really a partner for organizations of all size to help develop leaders and ICPs, whatever they have throughout their organization.

What's this framework for overcoming impostor syndrome?

So you want me to share?

Yeah, let's do it.

So essentially, the framework for overcoming impostor syndrome is it's a four-step framework. And when I was first at Pepperdine, I started off playing baseball at Pepperdine. I was a high school All-American when I got there. I was like, "Everybody's as good as I am or better." So I kind of got paralyzed, didn't do too well, ended up kind of getting hurt, leaving, had another shot to go to Arizona State. A lot of people said don't go there because there's gonna be 17 guys trying out. I'm like, "This is my last chance." And so I developed this framework to overcome impostor syndrome or limiting beliefs. And step one is really labeling your fear. So I call it purposeful awfulizing. And you can use this in a lot of ways, but think one year in advance. Right? Say you get an opportunity to give a keynote somewhere and you're nervous about it. But think: what's the worst thing that could possibly happen? Okay, it doesn't go well. Right? So who cares? People are upset or laugh at you. You can overcome that. Once you understand what you're afraid of and that you can overcome it, then just go for it. So step one is labeling your fear. Step two is really working hard. I mean, I don't think there's any hacks when it comes to hard work. You just have to put in the work. And when you do work hard, it really even gets those thoughts out of your mind because you're so focused on putting in the effort, whether it's fielding ground balls as the first guy in the field, last one to leave. And then step three is really deliberate practice. And what I mean by that is it's easy to procrastinate and go to areas that maybe you could work hard but not on the most focused things. But in giving a keynote, if you're having a hard time with transitions, focus on that. If you're a new manager and it's tough to have difficult conversations, just get out of your comfort zone and really work on that. And so once you've labeled your fear, you've put in the hard work, the deliberate practice, and when it's step four: learn and let go. Right? So here you are. Time to step on stage or into the batter's box, whatever it's gonna be. Know that you've put the effort and the preparation into it. Stop thinking about everything. Just go out there, do your best. If things work out, great. If they don't, get some feedback and everything's an opportunity for growth, for learning. And I think a lot of time, Joel, people just don't give themselves enough credit for even getting out of the comfort zone and taking opportunities. And so I mean, that's just the framework that I've used, and I've shared it with a lot of people who've found value in it.

Yeah. Yeah. That's way more than overcoming impostor syndrome. I mean, that's how to do difficult things. That's how to be successful. As you were listing those off, I was like, "Yeah, this is what I do." You just described the majority of my life when I want to go do something. It's usually difficult. I have to figure out why it's—why I don't want to do it or why. Often I'll know it's good for me and I should do it, but I'll have some hesitation or I'll have a dream to do it, but then I'll get shy. And so the first thing, you know, that fear, then you've got to work hard. You're exactly right. The deliberate practice is usually when I bring in other people. So that's usually when I go into coaching or therapy, like physical therapy, or some—when I don't want to do deliberate practice for me is usually—I call it high skill, high skill training. And that's usually the thing I don't want to do by myself. I need another person in the room. That's just me. So that's where I would go seek out a coach. If it was speaking, I'd find a speaking coach. If it was comedy, I'd find a writing partner, you know, so on and so forth. And then the letting go, that moment—you described it perfectly, right? When you're sitting there and they're about to call your name, next coming to the stage, it's just like you've done all you can do. All you can do now is just take a deep breath, relax, and just go out there and just do it. You know?

100%. And the good thing is, from playing baseball to—I got an opportunity to do a talk at the Naval Academy a year or two ago, a year and a half ago. And of course, you're gonna get nervous. And I think having a little nervousness is okay. You know, it kind of keeps you on your edge. But I think anxiety sets in if you don't do the preparation going into it, and you don't do the work, and you're unprepared stepping into it. But whether you're stepping on stage for comedy or into a boardroom or whatever it is you're doing, if you put in all that preparation and that work and deliberate practice—I like what you said about deliberate practice because it's also kind of like an accountability partner. You know, you hired a coach or you're working with the speaker, so you got a little skin in the game. And like it or not, it helps keep you accountable.

Well, it's the easiest thing to—you can push that off and be like, "Well, I'm working hard. I am doing these other things," because there will be certain things that come easier to you. And so it's like you get really good at them. It's fine. But you have to focus on—it takes a lot more effort to do that deliberate high skill stuff. And I noticed for me, just grabbing that other person that I respect on the subject and then having them just walk through the same exercise I could walk through by myself. But I just need—that part of me needs somebody.

And I like what you just said right there too, because it's easy to gravitate towards something that maybe you're comfortable with and then still say you're working hard. Like, "I'm working hard, but this is kind of easy, so I'm enjoying this," where you focus on that high skill or whatever it is that you really need that help with. And also, you know, having an expert, like you said, that you could role play with, who can give you feedback. Because sometimes if you're putting in hard work—I'm not a golfer, but you know, if you go out to the driving range and hit the ball a thousand times, but your setup is wrong or your hands—my deliberate practice to me is also getting it right and having somebody that can share with you feedback. And feedback's a whole other thing. I mean, I think that the best leaders I've come across—sure, they know how to give feedback, but they also know how to really receive feedback. You know? Some people feel open enough to talk to them about it and then learn from it and grow.

Absolutely. Yeah. No, this is good. Alright, so Rob's cool. He recommends good people.

So he's a good dude. I just set him up with a bunch of podcasts. His book's coming out pretty soon.

Oh, he's got a book coming out?

Yeah. Yeah. And I could forward you—well, I mean, he sent me something about it. So yeah, I reached out to—I got a podcast too, and of course, I'd love to have you on. But he—I just reached out to my network, got him on a bunch of shows, and I think he's actually coming out to San—well, I'm in San Francisco. You know? I was just out in Nashville last weekend. But—

Oh, that's our town.

That's your town. I love it out there.

It's cool. I mean, we moved here three years ago. So we're from Florida originally.

Okay. Yeah.

Yep. And we're from a beach town in Florida. And we were born and raised there. Both my wife and I, we lived there our whole lives. And we're like, "Let's go on an adventure." So picked Tennessee, and it was a good choice.

Nice. I mean, how many kids you guys have?

We have three under the age of 10.

Nice. I got two under the age of 10. Eight and four.

Nice. Yeah. Boys and girls?

I got a girl and a boy.

I got it.

Yeah, I get it. And I wish my wife was that adventurous, but her family's here. You know? But because everybody I know is telling me I should move out to Franklin. You know? Because I—

That's where I live.

That's where you live? I was at the factory. That's where that—I was at the—

The factory at Franklin?

Yeah, factory at Franklin.

I've been there. Yeah.

Yeah. And so—

My buddy has an office there. There's all that shopping, but then above, there's offices.

Yeah, exactly. And I was walking around the town, the ice cream store. It just looked like a great little town.

Yeah. No, we love it. Real quick, before we continue, I wanted to give a special shout out to DigitalOcean for sponsoring this episode. DigitalOcean is cloud infrastructure that's simple to spin up, complete with integrated AI dev tools plus 99.99% uptime SLAs and industry-leading pricing on bandwidth. We all know DigitalOcean. It's super reliable. It's been around forever. And now with DigitalOcean's Gradient platform, developers can train, fine tune, deploy, and scale AI workloads all in one place. DigitalOcean is reliable and affordable at any budget. Companies can save up to 30% on their cloud bill when they come to DigitalOcean. Use code DO25 and get $200 in free credits to get started. Simple cloud, powerful AI, built to scale. That's DigitalOcean.

Now, back to the episode.

So, hey, when we're doing the prep for this, this phrase, "purposeful awfulizing" came up, and I had to Google to see if it was a word that you made up. Turns out not. It is something that happens. Can you tell me about the purposeful awfulizing?

Sure. I mentioned a little bit earlier. I use it as—say, for instance, you're making a big decision. And so fast forward one year. A lot of times what people do, whether you're expanding in work or you're gonna acquire a company or hire somebody for C-level role, you always put on rose-colored glasses and think the best of what could happen. But really, when it comes to a big decision, look at one year, and what is the worst possible thing that could happen? Like a black swan, whatever. And is it something you can overcome? So if it's a situation where you acquire this company and it's gonna potentially bankrupt you if everything falls apart, then go back to the drawing board and do something else. So that's really what purposeful awfulizing is. It's just taking things to the worst extreme as a way to use it as a decision-making tool, really.

Okay. So you imagine the worst possible outcome, and then you—

Make your decision. I thought I—found it somewhere else? I mean, yeah. No, what do you—

I Googled it, and it was—it says awful—I just Googled the word "awfulizing."

Yeah.

And it says, "In the context of rational emotional behavior therapy, the tendency to exaggerate the negative aspects of a situation."

Yeah. Well—

We'll get—oh, look. Here it is. Right at the bottom. "Invented by Damon."

Does it say that?

(Joel Beasley at 00:14:17) Are you? No, no. I'm just trying to help you out a little bit, help me out a little bit.

(Damon Lemby at 00:14:21) I mean—

(Joel Beasley at 00:14:21) I—

(Damon Lemby at 00:14:22) I mean, you should have my ghostwriter's name on there, you know, the one who helped me with my book. But yeah, I mean, she helped me with that. Yeah.

(Intro Narrator at 00:14:27) Damon is the second mentioned from what I'm seeing.

(Damon Lemby at 00:14:31) So there you go. Josh—

(Intro Narrator at 00:14:33) Or something.

(Joel Beasley at 00:14:33) Is it really?

(Intro Narrator at 00:14:34) Yeah. You know, if I could pop this in real quick.

(Damon Lemby at 00:14:37) Yeah, another one is the trust tax.

(Joel Beasley at 00:14:39) I don't—

(Damon Lemby at 00:14:39) I don't know if we talked about that at all, but that's a good one too.

(Joel Beasley at 00:14:41) No, we will. Oh, okay. There he goes.

(Damon Lemby at 00:14:44) Yeah, there we go. So I—

(Intro Narrator at 00:14:45) I think that counts.

(Damon Lemby at 00:14:46) Yeah, we'll give it to Josh. Yeah.

(Joel Beasley at 00:14:48) Thank you, Google.

(Damon Lemby at 00:14:49) Here you go.

(Joel Beasley at 00:14:50) They're playing favorites because they're out in San Francisco too. I'm just kidding. Okay, so we got the purposeful awfulizing, which is quite a word to say. It's a hard word to say. And then what did you want to run into real quick? I cut you off a little bit.

(Damon Lemby at 00:15:07) Oh, no, not—I mean, at the end of the day, all I care about is whatever conversation we could have to better serve your audience is really—okay, it's whatever it is that, you know, I can tie back to to better serve your audience. You just gotta let me know, or we can just—

(Joel Beasley at 00:15:22) Yeah, let's talk about this. So I hate when people try to do the family at work thing. And I saw that in your book, and I was like, okay, what are your thoughts on when work tries to say, hey, we're all a big family?

(Damon Lemby at 00:15:38) Yeah, I'm opposed to that. In my opinion, as a business leader, small business owner, somebody running, leading a team, just like in sports, it's your responsibility to put an elite team on the field at all times. You owe it to everybody else in your organization. Now it's nice to say you have a family. I mean, but you can't fire Uncle Joe. He's always gonna be your uncle. You know? So there are situations where people outgrow their roles in an organization and they opt out, and that's totally fine, right? That doesn't mean they're not loyal or anything anymore. And I've also run into several situations with clients we've helped, and I've seen internally at LearnIt, is, you know, you've hit your maximum capacity, and it's time for us to move in a different direction. Because what got us here is not gonna move us there, and I'm totally against the whole "this is a family over a team" because you owe it to your team to make sure that you're putting the best people on the field at all times.

(Joel Beasley at 00:16:39) Yeah. And when you look at the team, it's like you're there because you're a high performer.

(Damon Lemby at 00:16:43) Mhmm.

(Joel Beasley at 00:16:44) And you're getting paid because you're a high performer. And if you decide to not be a high performer, it's very clear that you're off the team. But to your point of the family thing, you know, I think we were really similar in our perspective of that. I was like, if you fire Bob, like, if you do that with a family member, they're still at Thanksgiving and Christmas. Like, there's no getting—I have never been fired from someplace and I still go spend Thanksgiving and Christmas with them. Yeah.

(Damon Lemby at 00:17:16) You know? Yeah. It's funny though because I've actually had people that I've let go, and they showed up to our thirtieth anniversary party that we just had. And one of the gentlemen I talk about in my book, actually, he didn't get—it was a mutual—Jim Mallett, very close friend of mine. I'm godfather to both of his kids. He was with me for fifteen years, one of the best Microsoft Office instructors I've ever seen. But he got to the point where he just was dialing it in every day, right? He just didn't care. He wasn't passionate about it anymore. And I sat him down, and I said, you know, we're not doing each other any favors. I know you care about me, and I know that I care about you, but you're just not happy here. And it's time to go out. Let's work together, and we can bridge the gap and get you, find a new role for you. And he's like, oh, it's hard. I haven't been out on the job market in fifteen years. I'm like, buddy, we have to do this because, you know, I'm gonna give you thirty days to figure it out. And he did. And he left. And fast forward eight years later, he's been at Okta for eight years, and he's crushing it over there. And he thanks me for helping get him out of his comfort zone. And that's one of the things, Joel, I think is really important as a leader too, is leaders have to get out of their comfort zone. Because if you're always protecting your comfort zone all the time, you're doing a disservice to the people on your team. It was tough for me to replace Jim. I mean, he was a fixture at LearnIt and, you know, a fixture for our customers. But I knew he wasn't happy, and I knew that he was no longer delivering the same level of service to our customers. And it turned out to be a win-win for everybody.

(Joel Beasley at 00:18:52) That was one of the lessons that I had to learn. So for my early career, I was the co-founder of several different softwares where I had a business co-founder that knew the business side of things. And so he would deal with all the different hirings and firings and all the deals and everything. And then about, you know, seven to ten years ago, when the podcast was getting more popular and started hiring people and building out more teams of my own, I started realizing that all my software stuff was very contractual. Like I had a project, hired a team, and it was very contractual. But when I started the podcast business, working with all the salespeople and hiring them and having never done that, I learned really quickly that it's actually the kind thing to do to notice someone's checked out and to let them go. Like there's a way to compassionately let people go. And then it's weird too. Cause here's the thing that got me in my first early mistakes: like, you don't want to, cause it's very uncomfortable. So like you can see them not performing, but you don't want to, like, you'll know that you have to let them go, but you don't want to cause it's uncomfortable. But then it's compassionate because what signal are you sending to them? Because now you're giving them an unfair experience in the job market because that behavior is not acceptable for this type of situation. So—

(Damon Lemby at 00:20:23) Well, and what kind of signal are you sending to the rest of your organization? You know, you mentioned earlier about having a high performing team. Well, if you make exceptions for people who are kind of checked out, then you're not modeling the behavior that you're striving for. And that sends mixed signals, which, you know, can really confuse teams and people just won't put in the effort anymore as much. And they're like, well, that guy is not, or that woman is not. And I also think—and it's hard, you know, for your listeners out there who are leading teams or small business owners—it's hard to get out of your comfort zone and have those conversations. I mean, it really is. I mean, before you get to the point of letting somebody go, you gotta have those hard conversations and try to coach them up, give them an opportunity, and figure out what's going on. But what I try to work with our clients on, and even internally at LearnIt where we got about 75 employees and managers and leaders, if somebody's coming to work every day and they're failing and they're struggling, I mean, they're probably miserable anyways. So you're being compassionate enough to them to help them go out and find something that they're better at, where they belong somewhere else, and they could be happy at their job. Because I think it's really difficult to be successful at your work if you're doing poorly and you're miserable. So it is compassionate.

(Joel Beasley at 00:21:41) I have had a handful of people come back and thank me for letting them go. Yeah. They're like, thank you. This—that was obviously not, like, a year or two later. They're like, I found something I really enjoy doing. Thank you for not just letting me sit there.

(Damon Lemby at 00:21:52) And I was like, all right. Yeah. No, it's true. I mean, but it's tough. And that—but it also takes a good leader or a group of leaders to be connected enough with their team to understand who's successful or who's drowning or whatever they're doing as well, you know, and then to be proactive and address it.

(Joel Beasley at 00:22:09) Oh, yeah. Like, I've never understood how you can lead people without knowing them. You know? Like, how you could just put them at an arm's length distance, not actually know them. And then, I mean, when it's like high stakes and you have an executive team, like, you really have to know everybody. You know?

(Damon Lemby at 00:22:28) Absolutely. And, I mean, one little tip I have on that is open up every conversation with something personal. You know? Just like, hey, Joel, how are your kids doing? Or what did you guys do this weekend? Or what's been going on? And then that builds a type of a connection, you know, I mean, instead of making a transactional relationship. Because what I see is that, especially these days—and it's not soft. You know? I mean, it's not soft. I mean, people want to have purpose and belonging. And what takes place, what transpires in your personal life, can affect your work life, right? You know, maybe their wife got let go. Maybe a kid's sick. You know? So if they're not being able to show up as themselves in the office, I mean, you have to—I don't know. I think that that's a good way to help start off a conversation. And it doesn't take very long. It takes fifteen, twenty seconds. And listen to what they have to say, and then you can move on to the business aspect of it. And then end those same conversations with, if you ever read The Coaching Habit, which is a great book. Yeah. "And what else?" You know, is there anything else on your mind you want to discuss? And whether it's helping them reprioritize what they have going on at work or if there's something they want to get off their chest. You know? I just think it's important as a leader, no matter how busy you are, if you want to have a great team, getting to know them. And I'm not saying you have to be best friends with them, and I'm not saying you need to know the ins and outs of their wife yelling at them the night before or whatever the issue is. I'm not saying that kind of stuff. I'm just saying, like, hey, what's going on, man? I mean, guy on my team just—it was his birthday the other day. I'm like, hey, Eddie, happy birthday, buddy. You know, how are the kids doing? And he's like, I really appreciate you asking. You know? I mean, that—and that's just—I don't know. I think that helps, especially if you're in a hybrid kind of work environment like I am, where I only see half the team on a regular basis and everybody else is all over the world.

(Joel Beasley at 00:24:21) Yeah. Yeah. That's a whole other, uh, hybrid work and—you had something about trust earlier. You mentioned something about trust. I think that's what I wanted to get into a little bit. And since we're talking about remote work and working with people, how do you—what do you want to say about trust?

(Damon Lemby at 00:24:39) Well, one of the other little signature terms I have in there in my book is the trust tax. And, uh, first and foremost, when it comes to leading a team, I don't think you can be a great leader if you don't have trust. And trust is earned. You know, you can't just—you need to earn everybody else's trust by whether it's modeling the behavior, you know, having character, whatever it is. Whatever it is, you need to build the trust with your team. Now the trust tax is—think of it this way. I'm sure you've been there. I've been there plenty of times where you really invest in somebody, and you go to bat for them, and they turn around and let you down for one reason or the other. You know, they quit and try to steal your customers. They lie to you. I mean, the trust tax is—and I learned this with my dad, really, who had a big heart and gave everybody a shot. Every once in a while, you're gonna be let down. And so you have two options. Are you gonna be, you know, somebody who's always on defensive and, you know, cynical, and look at people through that lens? Or are you gonna, you know, not be naive, but start off with an open door and believing in the people that you're bringing in? Like, you know, giving them a responsibility and empowering them to do it instead of micromanaging them or whatever it is. But, you know, 19 out of 20 times, it's gonna go well, but there's that tax, that 10% of the time—not even 10%, 5% of the time—you might get let down. And that's just that's just gonna happen. It's a situation you gotta learn from and go from there. I mean, we're all gonna get burned at some point in our career and in our personal life as well. So it's just—

(Joel Beasley at 00:26:25) And nobody wants to be around the person who feels like they're always gonna get burned. Totally. You know, that's like a—that's like a dull, disillusioned—that's not a good healthy—I don't want to spend time with those people. I want to spend time with—you know, early in my career, I had a couple great people that I got to watch their behavior, and then I chose to model it. And one of the things that has stuck with me forever, Damon, is this guy, Robert. He would do this thing where, like, whenever he interacted with one of his employees' family members, like they came for lunch or to an event or whatever, let's say it was a sales guy or me—I was a software engineer at the time on his team—he would say to my wife or my girlfriend or whatever, he would say, Joel is the best software engineer in the world. He is just unbelievable. And he would treat me really well outside of that, but he would go out of his way to make a point to tell, or like, if he were to see my kids today, like, do you know your dad is the best in the world at this? So I've been—I've just done that. Like, I saw that.

(Damon Lemby at 00:27:28) How did that make you feel?

(Joel Beasley at 00:27:30) It made me feel so good, and I wanted other people—and the thing is, you can just choose to hire great people on your team. And then when you have great people on your team, you're telling the truth. It's like—that's what I do. I'm like, when I'm hiring people, I'm thinking to myself, okay, like, am I gonna be able to be who I want to be with this person? Because I can't take a horrible person, and I'm not gonna do that. I'm not gonna talk up somebody who's not great. But you have great people on your team, and then you make sure to let them know. Even I do that with my—even my friends that I don't work with, with their kids, you know, like, when—because we've got the young kids and so we're around it and stuff. But, you know, your dad's the funniest comic on the scene, or, you know, something like that. And they're always—it's always the same thing. They're always stunned or, like, what? Or, you know, and I just know that it makes everybody feel real good, and it makes me feel good too.

(Damon Lemby at 00:28:22) And how easy is it to do it? It's so easy.

(Joel Beasley at 00:28:24) Does it cost anything?

(Damon Lembi at 00:28:25) It doesn't cost anything. I always do it all the time too. I mean, I'm like, your dad is the best instructor we've ever had, or I mean he's our best salesperson of all time, or he's just awesome. And it lights them up. And those kind of things are easy to do. I mean, I interviewed the legendary Doug Conant, who was CEO of Campbell Soup. He sent 30,000 handwritten notes. And he said that these handwritten notes would show up somewhere in the world, and somebody could be a janitor at campus, whatever it was.

(Damon Lembi at 00:29:01) But the janitor being able to show his wife or his kids the note that he got from the CEO, he said it would just make him feel so great. And for the rest of his life, still, people will remember those notes that he sent. Just easy gratitude.

(Joel Beasley at 00:29:20) Yeah, it is great.

(Damon Lembi at 00:29:21) See, that was—

(Joel Beasley at 00:29:22) That was one of the most impactful things, I'd say, on my whole career. I like you had in the book about Richard Branson, "Screw it, let's do it." That's always, he's good for a social media clip, right? We've all been at that point where we're just like, ah, screw it, like let's go. But is there some skill to when to use that as a decision-making process? Like, how do you go about doing that?

(Damon Lembi at 00:29:50) Absolutely. There's skill and thought that needs to go into it, and it kind of ties back to what we were talking about with purposeful awfulizing. You can't just say "screw it, let's do it" in a life-altering situation, you know, professionally or personally. I mean, you can't just pick up and move your kids to a different area without even doing some type of research on schools or whatever is important to you, or making a huge investment in something in your organization.

(Damon Lembi at 00:30:19) So there are times to use that and not to use it. In my book, it's pretty funny. I actually use a story about, I threw a party for Guns N' Roses back in 2006, 2007. And the short version of the situation is the club we were having it at told me, like, two hours before the party started that there was a chance that the water was going to go out in the neighborhood. And if the water goes out in the neighborhood, there's no water, there's no bathrooms or anything.

(Damon Lembi at 00:30:53) And so the decision was, do we cancel the party, or do we just say screw it, let's do it anyways and see what happens? And the bottom line is we just went for the party because even if the water went out and we couldn't make it happen, everybody just goes home. You know? So it's not like a life-threatening situation. So we said, screw it, let's just go for it. And same thing comes for opportunities, whether it's speaking gigs or whatever. Sometimes we overthink things, right? We overthink opportunities. Like, maybe I'm not good enough to do this, or I don't know how we're going to make this work. But sometimes you just have to go for it and then figure it out on the back end.

(Joel Beasley at 00:31:30) I love it. And then the big question—this has been a debate since the beginning of time—focus on elevating strengths or focus on improving weaknesses. What team are you on?

(Damon Lembi at 00:31:41) Yeah, I'm curious to see what you say. I think I know the answer. 100% on the strengths part. And I say that because I think it takes a lot less effort. You get a lot more bang for your buck to focus on somebody's strengths. And I also think that great leaders, if you have somebody on your team—I have multiple stories in my book about this—who has the right values. And I always hired for attitude and aptitude over skill even. You know, somebody who had the ability to learn and drive and work to do it over somebody with a bunch of experience who was a know-it-all. If somebody had the right values, you could usually teach them the skills. And sometimes you put them in roles.

(Damon Lembi at 00:32:24) I had one guy who started off in sales, a guy from New Jersey started off in sales, and he just wasn't, it just wasn't working for him. So I sat down with him, got curious, like, hey, you know, Joe, you're great. I think you're great for our organization. What are you passionate about? What do you think you're good at? And he's like, oh, I studied computer science and I was in acting. And at first I was like, computer science doesn't seem like this guy took computer science classes. Anyways, we moved him into an instructor role and he's crushed it ever since. So I'm a big believer in trying to improve your strengths. Unless your weaknesses are going to cost you your job and you need to clean those up a little bit, then that's my thoughts. What about you?

(Joel Beasley at 00:33:07) Yeah. So I'm an entrepreneur. I've been my whole life. And what I found out really quick is I came up with this philosophy on distance from revenue, like how close to revenue something is, because there's a million things you can focus on. And so I look how closely something is connected to revenue and then put my attention there.

(Joel Beasley at 00:33:30) And so what I found is that my strengths are the closest thing to revenue. And so I said, okay, for my personal development, I'm just going to improve my strengths. And then for these areas that are sagging over here, I'll just hire people that have those strengths.

(Damon Lembi at 00:33:46) Totally.

(Joel Beasley at 00:33:46) And then that way I'm just doing what I'm really good at. And then I'm doing the things I want to do, because you know, you've been a business owner for quite a while, you get burnout. I've done a thousand of these episodes, you've been doing it for a long time. And so it's like I have to focus on—I have a recurring event, actually, from a friend of mine, another entrepreneur who suggested it to me at lunch one time.

(Joel Beasley at 00:34:08) And so thank you, Andy. And so now I have a recurring event every three months that fires in my calendar that says "revisit Andy's list." And Andy's list is really simple. Are you doing what you love? What are you doing that you don't love? And who could you get to do that?

(Joel Beasley at 00:34:24) And I go through those—that's been going for five years now. And it's always a surprise when it pops up every three months. I'm like, yeah, every once in a while I'm like, yeah, I'm doing something I really don't love as part of my habit. Then go on Upwork or hire, open a new role or something depending on what it is, and that's served me really well.

(Damon Lembi at 00:34:42) That's great. A guy out in your neck of the woods, Michael Hyatt, has the Freedom Compass.

(Joel Beasley at 00:34:48) Okay.

(Damon Lembi at 00:34:48) And I've used something very similar throughout the last five or six years. I used to be in this business accelerator, and it was really the same thing. You figure out what are you passionate about, but what are you also strong at? You know? And just kind of reflecting back, where do you spend your time?

(Damon Lembi at 00:35:06) And you look at the things that you're doing that maybe you're not passionate about, you're not good at. Can you automate them? Can you eliminate them? And again, it just kind of helps you look back. And I don't, I do it probably once or twice a year, but I think it's so important to look at that. And what you said is so key. You can't do everything. If you try to do everything, you're the jack of all trades, master of nothing, right? And so build a team, whether that's Upworkers, these days AI agents, or whatever it is that helps support your blind spots or your weaknesses. But if you have those teams, you have to then be able to delegate those responsibilities and let people do the work.

(Damon Lembi at 00:35:52) Don't jump in and try to do it. Do what you were talking about. Focus on what's closest to revenue if that's important to you, which it should be, and what your strengths are. And let other people that you brought in, because you brought them in for a reason, so let them do the work.

(Joel Beasley at 00:36:06) Absolutely. Leadership advice. We've obviously been talking most of this episode about leadership advice. First question I have is, what is your favorite leadership book other than the book you've written?

(Damon Lembi at 00:36:19) Right now my favorite leadership book is "Team of Rivals" by Doris Kearns Goodwin. I think I said that right. And it's great. It's about Abraham Lincoln when he brought in all these members of his cabinet, and they are so different than him. You know, and some of them were his staunchest competitors and hated him.

(Damon Lembi at 00:36:39) But it's a great leadership book because it talks about the importance of diverse opinions and also about being humble and learning, and also how at the end of the day he turned these people around to be on his side. So that is one of my go-tos right now. And I also like a lot of Richard Branson's books. I think those are cool too. But I'm a big biography guy.

(Joel Beasley at 00:37:03) Me too.

(Damon Lembi at 00:37:03) Yeah, big biography guy. If I wanted, like, a strict business book, I'd probably say I really like "Amp It Up" by Frank Slootman, who was the CEO of Snowflake and ServiceNow and a couple other places. But I'm more into the biographies.

(Joel Beasley at 00:37:24) Me too, actually. When I was in my early twenties, I bought three. I bought Bezos, Branson, and Musk.

(Damon Lembi at 00:37:32) Okay.

(Joel Beasley at 00:37:32) And I learned more about business through those—they're not business books—but I learned more about business through reading their life stories than I have learned in any business book ever. Because what you get is you get this intangible of watching how they frame the world through their eyes, and that is the thing that I personally found valuable.

(Damon Lembi at 00:37:53) And what I think is so great about that is when I coach or talk to leaders of all levels, but especially high performers new in their career, I say go out and read 10 biographies. Just start with reading 10 biographies. Military, history, leaders, whatever it is. Learn from their mistakes, their wins, how they look at the world. I mean, there's just so many great lessons.

(Damon Lembi at 00:38:17) I'm a big Winston Churchill fan, in World War II stuff. And I just think that it's easy to connect leadership in the corporate world or entrepreneurial world with business. But I got a quick question. What's one great leadership book that you recommend?

(Joel Beasley at 00:38:34) Oh, I would say to read those three biographies.

(Damon Lembi at 00:38:38) Yeah.

(Joel Beasley at 00:38:38) And that's going—and then the other leadership stuff I'd say is do something very difficult, because you have to become a better person to do super difficult things. And usually when software engineers ask me for advice, I'll tell them to do something like go to the gym consistently, because usually people already have their professional vector pretty well locked down.

(Joel Beasley at 00:39:02) They have some skill. They're in the marketplace. They're earning some money. They're doing something with their skill set, and they're trying to figure out how to expand. Like, why am I not getting promoted? Why am I—well, there is this unspoken thing among humans where we all have these bars, and if you see a huge jacked dude come in, you raise your bar. Like, your standard just got raised. And we downplay so much, and you know, I'm 38. So what I've noticed over the past 20 years is we've all tried to take our physical appearances and downplay them, like it doesn't matter.

(Joel Beasley at 00:39:34) But I look at it like a computer case.

(Damon Lembi at 00:39:36) Like, it does matter. Even if it's subconsciously, it does matter. Nobody wants somebody to walk in two minutes late, sloppy looking.

(Joel Beasley at 00:39:44) You know what I mean?

(Damon Lembi at 00:39:44) Yeah, it's really not that cool. I mean, we do a lot of that work at LearnIt where it's just, especially with individuals early in their career, companies bring us in and say help these people just show up professionally on Zoom. You know? I mean, just look—but you're right. I think when people come across as being healthy or taking care of themselves, I think it goes a long way.

(Joel Beasley at 00:40:07) Oh, it just absolutely does. I mean, it's why, it's the main reason why I try so hard. It's like I get up and I do my exercise and I do my stuff and I eat right and I track my macros. And all of this is for—I like how I feel when I perform at a high level. And I don't like how I feel when I'm foggy or like not getting it.

(Joel Beasley at 00:40:30) I don't want to be the "Oh, it's 9 a.m., don't talk to me until I get my coffee" person. I want to wake up and I want to be focused and clear and I want to have a good day so I can feel good about myself and build that internal respect and so that I'm modeling the behavior that I want my kids—because they're not going to listen to a thing I say. They're just going to do what I do. So I want my kids to model it.

(Joel Beasley at 00:40:51) And so all of those things really drive me. And as you know too, being an entrepreneur, it's hard. You have higher stress levels. You have to work out because working out reduces the stress. So it's like you can do more difficult things if you're healthier. And so it's like, yeah, that's the life I want. And so I made a conscious choice to live like that.

(Damon Lembi at 00:41:09) Well, good for you. I mean, the only thing I'd add to that, which you kind of stated anyways, is I want to be around for my kids. So I'm 52, you know, and—

(Joel Beasley at 00:41:18) Oh, are you really? You look good for 52, dude.

(Damon Lembi at 00:41:20) Thanks, man. I'm trying.

(Joel Beasley at 00:41:21) I was going to say I was going to say 45.

(Damon Lembi at 00:41:23) No, I'm 52. You know, unfortunately my dad passed away at 62. Huge businessman, Joel, but he didn't take care of himself. You know? And he died of cancer, and a lot of it has to do with not taking care of yourself in his situation. And I really want to be around for my kids. One of the things that I did in his model of behavior, like, I quit drinking eight years ago. You know?

(Joel Beasley at 00:41:47) Mm-hmm.

(Damon Lembi at 00:41:47) Never got in trouble, but we drank a lot. And I just got to the point where it's like, just exactly what you were saying right there. I don't want to be foggy and wait till 10 to feel better. You know? Because as an entrepreneur, it is so hard. You're always on stage.

(Damon Lembi at 00:42:01) You know? Everybody's always looking to you. Right? Ups and downs. And I've just found that medicating yourself with alcohol or poor food doesn't do the job. I mean, I feel much better and ready to fight the fight if I'm just taking care of myself, getting some sleep, and not even a little hungover at, you know, especially as you get older.

(Joel Beasley at 00:42:25) Yeah, it's real simple. Get a screaming two-year-old and be hungover, and you'll just stop drinking. Yeah, I quit drinking about the time I had kids as well.

(Damon Lembi at 00:42:35) I did right before.

(Joel Beasley at 00:42:36) Yep. Yeah. And the medic—I love how you said using poor food as medication.

(Damon Lembi at 00:42:44) Yeah.

(Joel Beasley at 00:42:44) Because that is exactly what happens. You get high stress, you go eat some junk food because you're trying to get that dopamine hit and that sugar rush to overcome the bad feeling versus just addressing the root cause.

(Damon Lembi at 00:42:54) Yeah. And it spirals. Then everything kind of spirals, you know, and you're just in this wheel of garbage is what I say. So, you know, I'm not out there trying to tell people to quit drinking.

(Joel Beasley at 00:43:08) I will. I'll say it for you. Quit drinking, guys. It's poison. You're paying to put poison in your body.

(Damon Lembi at 00:43:15) And, you know, it's one of the things I'm most proud of that I've ever been able to accomplish is just to stop doing it. And if a guy like me—I mean, if I can do it, you know, anybody can. You just gotta put your mind to it. And I think I've been a much better leader. And obviously, I got a wild four-year-old son.

(Damon Lembi at 00:43:35) I could never keep up with—I could never keep up with Wally if I was hungover.

(Joel Beasley at 00:43:41) No. You don't wanna be hungover and get punched in the crotch. Yeah. That is not—

(Damon Lembi at 00:43:45) Yeah.

(Joel Beasley at 00:43:45) That is not fun.

(Damon Lembi at 00:43:46) Yeah. 6 a.m. on a Saturday.

(Joel Beasley at 00:43:51) Well, Damon, we made a podcast. How do you feel?

(Damon Lembi at 00:43:53) Great, man. It was an honor to be here, and you're a great guy, and your buddy, Josh, was super helpful.

(Joel Beasley at 00:44:00) Thank you so much for listening. And if you found this episode useful, please share it with a friend or colleague who you think would get value from it. And if you have topics that you would like to hear discussed on the podcast, either add me on LinkedIn or send me an email: [email protected].

(Joel Beasley at 00:44:18) Every time I get an email or LinkedIn message, it absolutely makes my day and inspires me to keep going.