Mastering Self-Awareness & Leadership with Industry Icons: Best of 2024!
28 Jan 2026 · 23 min
A multi-speaker podcast episode (Best of 2024) hosted by Bill Gallagher focusing on leadership, presence, and self-awareness. Key themes: rehearsal and mirror work for speaking; defining a personal leadership style ('lofty, playful, and wise'); self-acceptance and leading with 'agape' (care/love); surviving difficult bosses and leveraging setbacks (Gallagher grew a business to over $550M before 30); critique of hustle culture and designing smarter work; pricing psychology—pricing as an intersection of analytics and mindset (25-year practitioner who began at GE); midlife career reinvention (example of lawyer who bought a bakery); and sports-derived lessons like teamwork and time management.
Chapters
I mean, look, I know everyone's busy, everyone's busy. But I think you owe it to your audience to make sure that you're prepared. And when you come into the that setting, whatever that setting is, you should rehearse, you should have rehearsed. You know, you need to know exactly what's your desired outcome, what's the main idea? I want to take away organizing the content in a way that's memorable that you know, because, let's be honest, a lot of what you say won't be remembered, but they're certainly going to remember how you feel and the passion and the energy that you brought to the table. And so it's, it is multifaceted and it is, it's a very complex, it's complex work. But if the, the secret is how to what's try to help people find their unique style. Like, what is it? How do they. For me, when I was in corporate and even today, I had three words that I wanted everyone to take away when after my interaction, he's lofty, he's playful, and he's wise.
Aha.
That's what I wanted them to remember.
Uhhuh.
So when people, some people got kind of in the gossip, in the gossip churn, I would want to elevate the conversation. If we were starting to get critical about what's happening in the organization. I wanted to elevate the conversation. I wanted to bring bring wisdom to at times when people just couldn't see that things were going to improve and get better. So defining that style, your unique style and how you want to be remembered. And of course it includes your voice and how you know your tone and temperament and some degree what you're wearing. But more so how do you want people to remember you and, and how do you want them to make them, how do you want them to feel after you've interacted with them?
Yeah, you know, I've had, I'd love to hear some of the work that you do, like granular level, because I' had vocal improv, I've had speaking and singing voice coaching. I've had voiceover work. I've done work with movement, the structure of talks, the presentation, formatting, like how to structure the flow of things, how to design curriculum. I've had training and work in all of those different areas. And I, I, they all help. Oh, comedy. I did standup comedy, like all that kind of stuff. And yet, um, the like the deepest thing is like an acting and speaking thing called mirror work. And if you practice a talk or Lines or whatever in the mirror again and again till at some point the lines disappear and the humanity is there and the connection to the person in the mirror is there. Like, that's the deepest thing. But the thing that. That revealed to me more than anything else was dealing with everything over there, right? Looking at myself in the mirror or right now in the camera, that is that I can't be with, right? And getting so, like, I'm a human. I got all these faults. I know what they are. I know the things that bug people again and again about me. I know I'm going to make a mistake. Like getting, like, totally comfortable with myself just gives my massive freedom to then rely on movement, speaking, voice message, etc. Right? Like that intimacy, all of that kind of emotional range. Learning to move through emotions, not to resist them, to let them come up and go. Like, all of that kind of stuff comes together with. With the, the self acceptance and self awareness and. And like, you could say love. Really? Like, when you truly, like, love yourself, you look in the mirror and you're like, oh, I'm good with that. Guy or gal. Yeah, I get them. That's a powerful place to be.
It's. I'm glad you brought up love. It's. It's certainly. It was a hallmark for me when I was leading teams in corporate America. I started using the term agape because I figured love just freaked people out. Like, oh, my God, Raimi's talking about love. Like, but it's so. Yeah, but. But from a spiritual scent, like, how do you connect with people at a deeper level to show that you really care and you love and admire? And countless times I told people I love them in a corporate setting, because I did. I cared for them.
I could tell you where I. I came close to being crushed, but I. I emerged victorious. How's that? So one day I'm in my cubicle and I'm working, and he shows up with this guy I never met. And he asked me what I thought of this piece, software called Mineware.
And.
Wait, was it called mine? Anyway, he showed up with this guy and he asked me what I thought of this software product. And I said, you know, it's kind of mediocre. It's drilling practice. You know, two plus two equals four, Steve. It doesn't really take advantage of the Macintosh graphics and stuff, so it's not strategic for us. And then he turns to me and turns to the guy and he says, guy, I want you to meet the CEO of the company.
So now.
Okay. Now if I had said, oh, it's a great piece of software. You know, Steve probably also thought it was a piece of. And if I had said it was great and Steve thought it was a piece of, I might have gotten fired right there in real time. So I passed the Steve Jobs test. I live to fight another day, invest another day.
Yeah, I worked for a guy once who was really remarkable. He was an extraordinary storyteller, inspirational speaker. He was also a very complicated individual. Like, personally, in many ways that I won't share. But.
So I'm working with this guy.
And yeah, he had notorious stories and really weird things, but. And then, like, once a year, we'd have to do our annual strategy and plan for each of the market leaders. And I came in and I had my whole thing, and I'm talking and I'm first up in the day, and I actually have the biggest market segment, and I'm giving my show, and I've spent time preparing it, and then he just is, like, in rare form. I don't know if he slept badly or is down or something, but he just starts. He just starts lighting in me, starts swearing at me and humiliating me. Your fucking problem, Gallagher. And I will. Show will get edited now. But, like, I'll tell you what your fucking problem is. You don't know how to sell anymore. And, like. And I just. I'm like, oh.
And I. Oh.
Shocking. And I just, like, inside, I wanted to cry. I'm like, this is the worst possible thing. I couldn't even imagine. Now I'm in my mid mid twenties, so I'm not that old. And. And I. But I am like, I have to get through this. And he cannot see me cry. Like, crying. I am not crying. And I'm famous for crying, right? Like, on stage to inspire people or whatever. But, Mike, no, not today. You. You're not. Like, this is how I felt. Like, right? That. And so then I finished the thing. We get through it, and then it went really, really long. And then we take lunch and. And now my peers are with me, and. And they're like, dude, that was odd. We felt bad for you. I'm like, yeah, but you didn't say anything. You didn't interrupt.
You didn't run interference for me.
You just let me weather that storm, that blast or whatever. Then we come back from Lodge. He's like, mellow. Maybe had a drink at lunch or something, I don't know. But, like. And theirs were fine. And they, like, sailed through. And.
And.
And now. And now looking back, you know, that probably was a valuable experience.
Right.
I learned that I can that getting through, surviving things. And if I hadn't gotten through, right, I wouldn't have gone on to do one of the most important things, which was grow a business over $550 million before 30. Like, you know, that's a really important experience in my life and changed how I view executives and myself. And there are many lessons in that. But I had to get through that.
Because hustle culture is bullshit. I'm sorry, but if you see your people hustling around, all that means is you suck at management, right? You suck at management, you suck at layout and design, you suck at making things easy to do. And that, for the most part, you probably are wasting massive amounts of labor. Though I can show case study after case study of us going into a place and reducing labor by 70% by just moving the items around to get them closer to the people doing the work. We spend about 40% of our time at work looking for stuff, looking in emails, looking for files. What's the status update on this? Can you verify this? Can we double check this? Can you quality check this? Every time you hear a word like that, it means I don't trust my people and I. I do not trust my process. Because if you did, you wouldn't have to spend 40% of your time administering and checking and double checking and rechecking. I mean, if you did that to your kid and stood over their shoulder and checked every little thing they did, they grow up to have mental issues. And we've literally made this the ideology of modern management, and it's completely nonsense. Every time I hear Gary Vee. I mean, no offense, Gary, but I would do an MMA fight with you just to get one punch in. In the nose to be able to say, shut up. You have no idea what you're talking about. You've run online wine stores. Like, come on, man. You've never been in the trenches. You don't know. And I want to make this. I said I want to tell the caveman story, because to me, it simulates what we need.
Please, hustle and grind. There's a time and a place for it in a moment in time. But if hustle and grind is your everyday, regular thing, then you're missing flow. You're missing zone of genius. You're missing the intelligent design. You're missing up leveling. Right? Hustle and grind is exhausting. It's not sustainable. No.
And for some reason, we have these damn signs all the place. And every time I see one I just want to take it out and burn it. I like that scene from Office Space where they took the, the printer out and they hit it with the baseball bats. It's like that word hustle is such. There is a time you're right when you're first getting started, when you're launching a new product. There are times, but the capacity of human beings cannot operate at 120% all the time. You got to get smarter and not work harder.
I've been a pricing geek for 25 years, and I started my pricing career at General Electric, and then I went on to do that work at other Fortune 500 companies. And in these giant corporations, the pricing work was very analytical and very, you know, we were doing segmentation analysis and elasticity calculations and things like that. And when I started my firm, I had the idea of bringing that kind of analytical expertise to the medium and smaller companies in the market. But what I very quickly discovered was the biggest problem and the biggest obstacle, I guess I would say, to making more money with pricing isn't better calculations or, you know, really rigorous cost analysis or, you know, it's nothing that you can find in a spreadsheet. It's all between the ears of the seller or the decision maker, whether that be the entrepreneur, the leader, a salesperson, a sales leader, that most pricing decisions are made from a place of fear, not from a place of confidence. We're mostly pricing in this very defensive way, like, what's it going to take not to lose the work versus pricing to win confidently rooted in our true values.
Yeah, really, really, really interesting. I think that comes up again and again in conversations. People are, are not thinking about the value and the competitive landscape so much as it's like if we raise it and salespeople are telling you like, oh, we've got to drop the price. And market makers of one kind or another are focused on moving prices the only lever they've got and, and missing out on, yeah, maybe we didn't need to do that price. I think we've all had that moment where you threw out a price and somebody said yes really quickly, and then you're like, shoot, I should have priced.
Higher, leaving money on the table. I call those auto yeses when you say a number and somebody just says yes to it and there's not a negotiation back and forth. That's an auto yes. And most organizations get those on some frequency, maybe even quite a lot. But we tend to ignore that kind of quote unquote, good data or the data we get from our customers that our pricing is fair or maybe even too low. We pay too much attention to the data that we get from customers that our prices are too high, which is all the customers complaining, complaining, complaining, beating us up. And I will tell you, customers complaining isn't actually data. It's noise. The only data is did they buy, did they not buy? And we are afflicted. And there's lots of reasons for this, and mindset and psychology is a big part of what I find fascinating about pricing because it's the biggest problem. One of the things that gets in our road is something called a negativity bias, which is, you know, we retain recall negative events with greater frequency and intensity than positive events. So you could hear, you could get 20 auto yeses in a row. And one customer, you know, punches you in the face about pricing and you know, sales reps are running back into the boss and our prices are too high. You know, we can't get that. So we tend to overreact to the negative and, and ignore all of that data we get from our customers that our pricing is fair or too low.
So you've spent 25 years in pricing. What got you started or interested in pricing at ge way back. Was it an accident or was it deliberate?
Nothing is particularly deliberate in terms of how I ended up in pricing. And I would say that some of that has to do with, I had no idea this was a career. I had no idea this was a business area. And I will tell you, I meet a lot of business owners and leaders today that still don't know that there's pricing consulting or pricing training like that. They don't even know that exists. So, you know, I had career day and it was locked. Doctor, lawyer, you know, teacher, artist. So I was good at math and science and I started my career as an engineer and. But I was very interested in the customers and what do they care about in the commercial side of the business. And the best way for me to get closer to the customer as an engineer at GE was to enter a program they were investing a lot of time and resources in at that time, which is GE's Six Sigma program. So I became a Six Sigma black belt, one of the early black belts at ge, and did rotations in a bunch of different areas. And one of those areas was pricing. And I just kind of fell in love. I love the, the fact that it's an intersection of art and science, of people and process, of data and psychology on, on paper, in theory, if you ever read a, you know, a textbook about pricing or maybe an econ book or something. There's this supply, demand curve. It's this really simple mathematical relationship between what you charge and what you know, what you sell. But in the real world, it's a lot less new. It's a lot less black and white. It's a lot more gray. There's a lot more bluffing. I Can I compare pricing to poker? You know, it's like you're looking at the strength of your own hand. You're trying to judge the strength of your opponent's hand. Everybody's bluffing. Buyers are trying to hide how much they're willing to pay. Sellers are trying to hide how little they're willing to accept. And there's a lot more nuance to the. And mystery and obfuscation to the game of pricing in the real world than this very simple mathematical relationship. And I just. I got very interested in the challenge that that presents for sellers, because we're often operating from fear. We buy the buff that the. The bluff that the buyers give us, and we under.
The next night, she had a dream, but more like a memory of her and her grandma cooking pies. I was like, okay. She said, I could even smell the pies. The next morning, she talked with the cohort, and she said, you know, it's interesting. When I go to a foreign country, the first thing I look at on a digital map is, where's the nearest bakery. I always want to go and smell the bakery, and I want to, like, see what kind of, you know, special foreign goods they have baked goods in there in that community. And so then she said, like, you know, when I actually invite people over for dinner, I always tell them to stay for dessert, because that's the thing I want to cook the most. By the end of the week, she realized that she had more options than she thought. She doesn't have to be a litigation consultant. She could go to pastries, like, become a pastry chef and go to pastry chef school for three months to see if she likes it. And she did. And therefore, she quit being an attorney, and she bought a bakery in her neighborhood that had closed during COVID And she now is an entrepreneur running a bakery, and she's actually about to open her second bakery. So, you know, what we have to do sometimes is create this space in our life, this midlife atrium where we can actually sort of imagine new things that we could do, and we need to sort of come at it from a different direction. And that's part of the reason why mea has become so popular is because there are a lot of people in the broad definition of midlife, I define it as 35 to 75 who are looking for more options in their life. They're looking for a new pair of glasses in which to look at their life, not just professionally, but sometimes personally as well.
So for me, personally, right, I turned 60 in a few months. I and I changed my career significantly at 50 and became a full time coach. And I am pretty clear about, you know, that I want to keep working for a lot of years because I, I feel good, like I enjoy it. You know, I like the kind of work that I do and I'm pretty clear about my life's purpose and how my life purpose shows up at work and at home and in all areas of life and in different ways, but that there's a through line there. And so I'm not like looking for that. But I do really want it to keep evolving. So I don't want the way that I work today, even if I know the general area of kind of work that I want to do, I don't want that to be the way that I work even five years from now. I want that to keep evolving significantly and change the pace of the nature. And I imagine what it'd be like. But then what I think about myself and my life at 60 is really different than what I thought about at 50 or even 55. Like it keeps evolving and certainly the last three years really accelerated a lot of things for many of us. Right?
Yeah.
I mean that what you're describing is the evolution of learning and that and curiosity is the tap root of that. And so when you're curious, curiosity is really the, it's sort of the source for creativity and innovation. Creativity and innovation get all the, all the highlights and the headlines, but curiosity is often behind that. And what, what curiosity requires is an open. First of all, you have to have enough space to be curious. If someone said let's have a, let's have a curious brainstorm and we have 30 minutes to do this, no, you have to have the space to be able to be curious. That's really essential. But also you have to have less judgment. You have to be willing to try things and have them fail, come up with stupid ideas because that stupid idea might lead to another idea. And so long story short is curiosity is an undervalued part of business. And for you, as you're describing your evolution, your evolution will only happen if you're curious and willing to learn and willing to try new things. And so it makes a lot of sense. But frankly, the process and mechanics of business, it's almost like the process and mechanics of education. It breeds out of us, our curiosity as a teenager or as a business person, because process is what we get caught up in.
You obviously developed some habits and things like that. What do you think is really important from all that sports experience in business?
A lot. Definitely learned a lot. Right off the bat, everyone's gonna say teamwork. I would say it actually took me a little bit longer to realize how much it truly correlated. You know, you go into a locker room and everyone knows the goal and the mission, and everyone's gonna play hard because they know they're gonna be cut the next day if they don't. And they know, like, right from the bat, you know, you've known your whole life that you're there to win a football game, and if you don't, it's a problem. Then you go into the business world and you start hiring people, and you realize really quickly that they're not showing up to win. You know, there's a lot of time showing up to be there, just collect a paycheck and get through the day. It really took me really, a couple years and, you know, talking to mentors and my dad and other people. People and sitting back and really thinking how we could make this a team and take it to that next level. And took me a lot of different ways to do that and figure that out and build the right culture, but definitely learn teamwork. Then had to apply it in a different way. Just the hard work of every day, the everyday grind of being an athlete. Definitely converted over, you know, waking up early, you know, putting that work in, you know, being there. Long days, hard work, it's kind of the same thing. But really, I think the biggest lessons I learned playing sports was in college, and it was really time management as a student athlete. It's one of those things where I say, I don't think I could go back and do it again after I finished it. Your time. Your time's locked up all day, every day. You know, you wake up, you're at mandatory study halls, you're at mandatory lifts, you're going to class, you know, right from class, you're going to. To, you know, work out or to practice. Then you're going to a mandatory dinner and you're getting home and you have to study. And then all that time, too. You gotta actually be a. Be a college student as well and have some fun, too. So if you can manage that, and, and get good grades and you know, I ended up leaving school with, with A's and having a degree from the business school. But if you can do that, you've kind of figured it out, you know, how to manage your time and you're very good at it. And, and being an entrepreneur is the same way. You know, it's, it's these crazy tasks that you're never going to ever expect to do. And you know, next thing you know, you're figuring it out. You're managing your time and you're multitasking as well. Just these crazy tasks that you never thought you'd do. You're now, you're now pulling off. So I thought college, getting through college taught me a lot about how far I can really push myself and how much I could really manage.
Yeah, there's definitely something there about being smart with your use of time and how you blow time off and where you procrastinate and the whole world of that. So one of my favorite speakers some years ago was a baseball performance coach. And he's like, not like a team coach, but like individual, like psychology type performance coaching. And he's like the thing that separates the all players, you know, and major league baseball players is like an infinitesimally small number. And even like the rank and file pro baseball players from the serious players is a tiny difference in, in actual hits and runs. And he said, so the key thing is dealing with failure and setbacks and getting really great at it. What's your experience or thought about failure and setbacks in sports, in life, in business, and what's your sort of personal psychology around that?
Yeah, for me, so I always go into it and if you failed but you truly did prepare to do it the right way and you know, you did everything that you could to win, but it just doesn't work out. It's completely different than going into it and knowing that you didn't put the effort in and then failing. So that's how I always looked at it. You know, if I did this, if I did prepare and I did everything that I needed to to win and it just didn't work out. I'm fine with it if I know that it's kind of like studying for a test. You know, you, you didn't do the work, you go and you end up getting an F. You know, you could have actually done better. If you put the work in then, you know, you feel terrible about it and you got to figure it out and, and bounce back from that eventually. But that's, that's how I've always looked at that. And then if it is a failure, if you learn from it, you know, there's, there's a lot that could come from that as well. But if you keep on doing the same thing over and over again, then it truly is a failure at that point.
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