March 5, 2026 – Highly Defective Bosses Joel Hilchey and High-Altitude Entrepreneur Chris Clearfield

0:04 Intro 1 : Broadcasting from am and FM stations around the country. Welcome to the Small Business Administration award winning school for startups radio where we talk all things small business and entrepreneurship. Now here is your host, the guy that believes anyone can be a successful entrepreneur, because entrepreneurship is not about creativity, risk or passion. Jim Beach, welcome

0:26 Jim Beach : to school for startups Radio. Thank you so much for being with us. We’ve got a cram pack show we need every second today. First up, we have Chris Clearfield talking about high altitude entrepreneurship. It is a really cool thesis, anti thesis actually calls it. And then Joel hilchy is with us to talk about having fun at work and a lot of other things, creativity. It’s a great conversation as well. Here we go time to have a little bit of fun and perhaps craziness. Please welcome Joel hilchy to the show. He is a juggler and also a joggler, with someone who juggles while they jog my gosh, how not even try to figure that out. He has a business called bean stalk creative, and has just published his second book that I can find. The first one was called Brain spouting, how to become fearlessly creative and have better ideas more often. And he just recently released six and a half Habits of Highly defective bosses, serious lessons for accidental managers, and it is five star rated on that Amazon place. Joel, welcome to the show. How you doing?

1:34 Joel Hilchey : Hey, it’s great to be here. Jim, thanks for having me.

1:36 Jim Beach : It is my pleasure. Joggling. Joggler, did you come up with that? And are you getting it?

1:46 Joel Hilchey : You know, this started because I had this idea to set a record in something. I wanted to set a world record. And it turns out that to set a world record in a really common thing, you have to be really, really good at it. But if you, if you choose a really specific niche thing, then you know, you just have to be pretty good at it and find a really specific, you know, I guess, zone, or talent or something. And so, believe it or not, there is a world of people who are jugglers, and, you know, they’ll run marathons while juggling or or they sprint while juggling, and to do that, you still have to be pretty fast. I did some research, and I actually talked with two of the world record holders. A nice little tip there, reach out to people when they could mentor you. They often want to help out. But it turns out that if you juggle five balls, it’s more about the the juggling than the running part. And I was not a great runner. And if you say, You know what I’m going to run backwards, then it’s even it’s even a smaller group of people who bother trying. So although Guinness rejected my attempt because I stepped out of my lane, I am the unofficial world record holder for the fastest 100 meters running backwards whilst juggling five balls. Wow. Now just, you know, make, make it practical, you know. But really, I did this. Number one, because I thought it would be funny number two, because it was sort of my own little lab on finding a niche that that you know, you could do better than anybody else. And it was, it was a lot of

3:32 Jim Beach : fun to try it interesting. That is great. I love the fact that you’re unofficial record. We will brag about that. And by the way, I’ve just realized four books out. I only found two of them on the Amazon, but

3:44 Joel Hilchey : no worries, I was wrong. Well, one is a kid, one is a kid’s book. That was the first one. I’d written a story, and somebody asked, Hey, is that published? It’s called the time decline. And then the fourth one that you found is called teaching creativity. It was really an addition for kind of teachers or people in a teaching or leadership capacity who wanted to apply that brain sprouting framework and get their teams to be more creative. But you know, the theme, I think, is that for me, I didn’t ever really plan to be an author at all. I just had some things to say, and people started saying, Oh, is that good? That’s that’s a, could that be a book and and so I just started listening to what people were asking me to talk about and produce, and it was a, it’s been a lot of fun to write them over the years. Excellent.

4:35 Jim Beach : Well, it’s got to be fun or shouldn’t be done. So yeah, tell you about my creativity in the second grade. Mrs. Leeds was my teacher. I remember her vividly, and we had an assignment to draw a monster to see how creative we could be, and I drew a monster with three heads, and she told me that. Was wrong, because everyone knows monsters have two heads. That’s exactly word for word. What she said on the second grade I learned that I was not a creative person, and so I have that going for me. I know that I’m not. I’ve been told by a second grade teacher

5:18 Joel Hilchey : that’s so funny and such a shame. You know, the biggest barrier to creativity for most people is actually their own internal belief. They somewhere along the line, they start thinking, I’m not very creative, or maybe their bar is way too high. They think, if they’re not, you know, Taylor Swift, or, you know, some huge entrepreneur, that they’re not creative, but we all have the machinery in our minds that makes weird associations like this, and it’s when we bring in the judgment too soon that’s what shuts down the creative process.

5:52 Jim Beach : Well, I’m still trying to recover from it, and no matter what I’ve done, I still not proven her wrong. So to increase my creativity, Joel,

6:07 Joel Hilchey : when you need a creative solution, separate the idea generation process from your decision process. So usually people start with the question, gosh, I’ve got this problem. What should I do? And then they sit around and maybe they even ask their small team, you know, what should we do? What should we do here? And when you’re when you ask that question, you’re asking people to vote, generate ideas and judge them to be good enough. And you can see it. People sit around and go, Gosh, I don’t know what we what’s a good idea here? Gosh, maybe we should know that’s dumb, and they end up shutting down their own ideas before they even leave their lips. Idea generation is really like an associative process. It’s a divergent, lateral thinking process, and it’s kind of like a big flow of toppling dominoes, you know? And if you if you stop saying the things out loud. It’s like taking a domino out of the chain. So the best thing you can do is say, instead of saying, what should we do? You say, What could we do? And you have no commitment, and you just take a short time. I’m talking like one to eight minutes maybe. And just for that time, make a list. Make a list of as many things as you can. If you want to structure this more, you can write the numbers one through 30 down the side of a page and try to come up with 30 ideas. Or if it’s a really big problem, or, you know, you really want to get more divergent ideas, write the numbers one through 100 probably the first five or 10 ideas will be the obvious ones, and you’ll have to work harder once you get up to idea number 10 or 20 or 30, and you’ll find that even though some of those ideas will be pretty ridiculous, you’ll probably come up with things that you would not have thought of before. And then, once you’ve got that list, now you can say, okay, given that list, what should we do now? Now we can bring in the judgment or refinement or that comparative critical thinking, but the brain is really good at being creative and it’s really good at being critical, but it’s really bad at being both at the same time, so you want to separate those processes. That would be my best little tip.

8:22 Jim Beach : That sounds like a very formal brainstorming definition what you just did? Yeah, yeah,

8:29 Joel Hilchey : you know. And so many people, they roll their eyes when you suggest that sort of thing. Oh, that doesn’t work. But in my experience, the traps that people fall into, even if they have good intentions of saying, Okay, let’s take five minutes here and just come up with as many ideas as you can, as we can. Well, they end up fixating on one or two of the ideas. And so they stop thinking about quantity and start just digging into one idea. And they end up spending four out of the five minutes explaining, you know, their first idea, or they they start shutting down all the ideas as they come up. You know, you’ll hear it in people that say, Well, what if we tried this? No, no, that didn’t cost too much. That’s dumb. Okay, okay, fine. Well, what if we did that and said, Now the boss would never go for that. What if we did this now we tried that last year. Didn’t work, and it only takes two or three of these statements before everybody in the room sort of feels deflated, and it feels like why are we even bothering doing this? So I guess maybe that another sub tip here, in addition to setting up the people for the type of creative activity you want, the thing I would say, is get the right people in the room to begin with. If you know that somebody on your team is a total, you know, negative Nancy and just always playing devil’s advocate and criticizing things like, don’t, don’t, have your brainstorming session with that person that’s gonna, that’s gonna shut down your flow.

9:58 Jim Beach : Yes, we gotta get rid of that jerk. I hate that,

10:02 Joel Hilchey : at least for now, they probably have a ton of great input on how to make things better, but, but that’s the key. During that ideation process, you’re not so concerned about improvement, you’re you just want lots of weird, wacky ideas. You want people to throw things out and pitch things. Now this happens in comedy writing kind of circles. People just pitch ideas you want. You want people to throw out weird stuff and see what it what it triggers, and other people, and you can never predict exactly where it goes. That’s why it’s so exciting when it works.

10:39 Jim Beach : It is a lot of fun when it works. I’ve been in a room where the brainstorming has been just an amazing exercise. So a great process. Let’s play a game, Joel, let’s go through the six and a half bad habits of bosses, bad bosses, and see how many of them

10:56 Joel Hilchey : I have. Oh, love it. Love it. Okay, so habit one is function forgetting. So this is the bad habit of focusing only on one part of your boss job. So bosses are responsible for a lot tasks, yes, but also people. And then you could add into that short term and long term thinking. So you know, most, most accidental managers get promoted because they’re good at doing a thing, and so they tend to be really focused on the short term tasks and project management. The next most comfortable zone is that longer term strategic thinking, which is task focused. But now we’re asking, Are we doing the right things? The short term people side are our working relationships, and the long term people side are the Career Development conversations. Okay, so Jim on your team, do you have regular career conversations with people? And do you have, you know, do you kind of take take charge of those team dynamics, or the strategic directions as well. Or do you tend to focus on just one of them? But I got my fingers crossed for you.

12:09 Jim Beach : I think I’m pretty good at realizing what I’m supposed to be doing and focusing on that. And when it comes to people, I was very good until my company got to about 100 people, and then there were people in the office that I had never recognized and didn’t hire personally, and that got very hard for me. And I was never good at that phase. I don’t know how to score that. You’ll have to decide, but yes, I did have well, for example, I hate this story, but it’s a true one. I’ll tell you two stories. Caroline told visa something that was wrong and cost me like $500,000 when all in the money, oh my god, the world was $500,000 and yelled at her at the top of my voice, you’re taking the food out of my baby’s mouth. Oh my goodness. So she ran screaming. We never saw her again, and she just disappeared. Then another when we were that was when they were, like, five or six of us, when there were 100 of us, a guy, CFO, came in and told me that the comptroller quit. And I was like, Oh, that sucks. I really liked him. And five years later, I found out that he quit because he thought I was spying on him, because his office was below my office door. We had like a two story office with like a balcony, oh yeah, half of it, and I would come out of my office with full blown gillion beret, so it was hard to move my feet. I was not paralyzed, but kind of paralyzed, and I was looking at my feet all the time, and he thought I was looking at him every time I came out of my office, because I was spying on him, completely oblivious to me. I didn’t know I was spying, but that’s why he quit.

13:54 Joel Hilchey : Wow, you know. So I’ll put that into another category, which is habit five feedback fumbling. Now, it’s not that, you know, it’s probably not that you never gave this guy any feedback, but in the moment, while certainly the you’re taking the food out of my baby’s mouth, comment, it’s probably said, you know, no offense, without really thinking about it. And as angry as we are, and we all have these dollars that That’s right, we all have these moments, right? And, and those are the most challenging moments for bosses that those are some of the ones that they say, like, Ah, this is a bad situation, but they know that they weren’t at their best for it. Now, people will forgive the mistakes sometimes, so long as there’s been consistent reinforcement of the positive things. And it sounds like, what? What you know the CFO or the comptroller myth was the knowledge like, yeah, that you really. You like this guy, this you really appreciate this person. So we all do this. We all fumble feedback at different times, but feedback fumbling, I mean, there’s a bunch of ways to be bad at it. One is to not do it at all. One is to do it but to do it insensitively. And the third one is actually to be bad at receiving feedback. Now you probably wouldn’t have got to lead a big company if you were bad at taking feedback. But it does show up because it touches on our buttons. You know, it’s our ego at play here. So that’s habit five. We can jump around a little.

15:32 Jim Beach : Yeah, we’re gonna have to. I will say this about me, though. So I got to about 40 people or something, and we found out that the business was going bankrupt because of cash flow. And yeah, I told everybody, you may not see me for months because I have one thing to worry about right now, which is going and raising venture capital money. That’s the only thing I am doing now. And I left the business to my brother and some of the people who had been there since day one, my brother came in after he got his MBA, and thought he knew everything, you know. And so I put those three people in charge of the business, quote, unquote, and then I disappeared to go and raise venture capital. And I would be gone for weeks on end, you know, and I’d come back and there’d be four new people that I had nothing to do with, and I didn’t care, because I was waiting on a call from a venture capitalist. The last thing I have time for is to talk to you,

16:24 Joel Hilchey : right, right? You know that that is a constant challenge of, well, business is really at any size, because if you’re adding new people in, it’s probably because you’re so busy that you need another person and and so one of the big challenges people just forget about the people you know, and we get so focused on the task side. So maybe that’s a function forgetting, or that might be a sign for businesses that are growing and scaling at a higher level that there aren’t the systems to make sure your new managers are the people who are more present are also focusing on the people, you know, if they’re only

17:04 Jim Beach : people who were supposed to do that for me, yeah, all that stuff for me.

17:09 Joel Hilchey : Yes. Wouldn’t it be great if we could outsource the loving and caring part? So, gosh, there’s so many, so many little things that that can get in the way. You know, it sounds like one thing that you did not have an issue with, though, was habit two, which is mediocrity mongering. So if you’ve got high standards, this is really good, that bad bosses tend to lower the bar for everybody. You know, when there’s a real high achiever on the team, they worry that sometimes people are sort of like diminished, or they’re threatened by that high achiever, and so they downplay the high achievers contributions. Now that makes that high achiever say, Well, I’m not valued around here. I’m out of here, and they end up leaving. So mediocrity mongering is one to look out for, or when you have that like good enough sort of thinking,

18:05 Jim Beach : I thought I was always demanding excellence that we usually achieved it.

18:13 Joel Hilchey : It sounds like it, you know, it’s hard to grow. The mediocrity mongering shows up more in larger institutions, where people feel less connected to the outcome, or where the the institution, you know, not to paint a picture, but like governments, municipalities, large hospitals, even that’s an unfortunate one, where people feel like I’m just a cog in a wheel here, and it doesn’t really matter if I Do a great job, or just an okay job, and and, and high achievers don’t like that environment. They want to feel like they’re doing great work, and great bosses help them feel that way.

18:51 Jim Beach : Yes, all right,

18:54 Joel Hilchey : it’s hassle making that good bosses remove the obstacles instead of adding them in for people. Gosh, one of my favorite stories is this, remember back in the day when people had those cathode ray tube monitors, those big things that stood on your took up half your desk. Oh yeah. And somebody said, Guys, we used to have these things. And there was twice a day when the sun was shining into our office in such a way that we could not see our computer screens the glare off these things. Then they said we put in requests for window blinds for glare, reducing things, we got turned down at every step. There was literally no way we could arrange our guests. So this, this didn’t happen. So we all just end up taking our taking our coffee break when the sun was shining in on our screens. It may have made it totally unworkable for part of the day. I thought, isn’t this hilarious? There’s highly trained, paid professionals who can’t work because the sun is shining in their window and and nobody seemed to be able to fix this problem. A great boss, somebody put it this way, they like go to bat for you, and they got the good. To deliver. They can make your life or your job easier so that you can do your best work. I don’t know if that resonates at all.

20:07 Jim Beach : Yes, it does very much. So what about Go ahead, I’m sorry. Oh, yeah, no.

20:13 Joel Hilchey : Habit four is credit stealing and finger pointing. So you know, broadly, do you share the credit when things go well, and do you take some responsibility when things don’t go well? It’s not that, you know, it’s not that we don’t need to hold people accountable, but we great bosses tend to focus on the what now question, rather than just on the who have caused the the issue, right?

20:39 Jim Beach : Well, it’s very hard as an entrepreneur to not steal the credit, because we have to fake it till we make it. And so we need to boister our image, even our self image, so that it appears that we are cool and successful.

20:55 Joel Hilchey : Yes, yes. And you know, team members smell this. And to some extent, I think it might depend on culture and the specific field that you’re in, and maybe even location. You know, I’m a dual citizen between Canada and United States, and I noticed a difference in Canada, people are much more likely to share credit. If you say, Hey, you did a great job on that there. But you know, overall, more likely to say, well, thank you. But you know, really, my team member, really, it was, it was her idea. She did a fantastic thing. And, oh, and this person, they did a really amazing thing here too. And I’ve noticed it’s just in different parts of the world, or maybe different industries. People tend to, you know, be more ego protective, I think, you know. So you say, hey, this was good. Say, Yeah, I did that, and I’m proud of this. And maybe some of that is really functional, because, as you say, if the CEO is the one asking for that venture capital, you want the trust to be on you like you’re the one making that sale, but it has an impact on the people around us, if we don’t say at least, to them as an individual. Thank you. Your contribution mattered. If you’re going to hear me talking about this, you know, publicly, like it was our team’s idea, or this by Thank you know that I value what you contributed here. Yep, habit six is bully bossing. I bet you didn’t do this. One, aside from our, you know, a few random outbursts, which we all have, bully bossing is using fear and power tactics to try to get results, and it can get results in the short term, but it’s a short term strategy because it ruins relationships. And last one, I’ll just put it out there. Lob it up for the half habit. Six and a half habits, consistently inconsistent, which didn’t feel worthy of full habit status, you know, Jim. But when there’s not enough consistency for people to have predictable, stable routines. Then, then teams run into trouble, and they start being resentful, because the often visionary entrepreneur is off solving a new problem, but everybody else is left scrambling in the wake of the tornado that they created. That’s the one that I do most often. So those are the six and a half habits, right? You know, I wrote the book because I went from on a journey from being a solopreneur to now having a team. And we’re small. We’ve got 15 people total, you know, five of us full time, but, gosh, I made a lot of mistakes along the way, and at the same time, we’ve been able to build a really great culture. And I’m really interested in helping helping leaders become the type of leaders that people love working with. You know, I think the world needs more of that, because people do their best work when they feel good when they love who they’re working with, and they feel confident in their team. So I wrote the book because people started asking, Hey, how did you guys create that culture? What do you do? And I would share some of the techniques that we had stumbled on, and they said, Wait, tell me more about that. So it’s been a real joy to write the book and share some of these ideas. And even, you know, colleagues and longtime friends have said, Oh, that was good. I thought differently about this because of it. So it’s been, it’s been great. And that’s, that’s part of the joy of entrepreneurship, I think, is figuring out the things that we can do a little bit better along the way. I didn’t set out to be the best boss in the world. I just, you know, wanted to do a thing, and we needed some other people to do it together, so, but I didn’t want to be terrible either like, Well, I hope, I hope my team doesn’t quit on me or mutiny. And that was, that was a good bar to start off,

24:53 Jim Beach : and a great place to wrap it up. Joel, we’re out of time, I’m afraid. How do we find out more? Follow online and get six and a half habits. Good.

25:00 Joel Hilchey : Sure. So you can get the book anywhere you buy books. If you want to take the highly defective boss assessment, you can do that. Joel hilsey.com/bosses, and free assessment there. It’ll tell you all your defective habits, or hopefully you’re not so defective habits. But Jim, this has been great to connect and to share some stories.

25:23 Jim Beach : Likewise, greatly appreciate you being with us, Joel, and we’d love to have you back. Thanks a lot. Thank you. Bye for now. How do you think about the hockey thing where you lost Andy won?

25:36 Joel Hilchey : Oh, yeah, you know I because I was born in Canada, I was probably rooting for the Canadians in that game. But, gosh, I, you know, it’s exciting. I just like to see a good hockey game, to be honest. And that was a good hockey game. It was close, you know, intense. Were you paying attention to your own Olympics fan,

25:57 Jim Beach : Jim, that’s the only part of the Olympics I watched. I only watched the third, half or quarter or whatever period that was it?

26:07 Joel Hilchey : Yeah, you’re there for the the exciting moments. For sure. I tend to be a little bit like you just described, a sort of playoff fan. I’m a bandwagon jumper once I once, I get excited when the stakes are high. Yeah, that’s great. But gosh, during the baseball season, when there’s 180 games or something, yeah, there’s a lot of that’s a lot of games to watch. I’m not quite that invested, but I’ll watch the playoffs, yep.

26:34 Jim Beach : All right. Joel, thank you so much, and we will be right back. You. Man,

26:50 Jim Beach : we are back and again. Thank you so very much for being with us. Very excited to introduce another great guest. Please welcome Chris Clearfield. He is a leadership strategist, author and Harvard trained scientist. He was working in the trading industry when we had the meltdown in 2008 and he saw that firsthand. And then he we had the horizon deep well blow up in the middle of the Gulf of Mexico. And he saw that, and he and a friend decided to spend some time looking at how systems fail, and they wrote a book about that, called meltdown, why our systems fail, and what we can do about it, which was a winner of the National Business Book Award. Very impressive. He has a new book out now called the high altitude entrepreneur. Oh, by the way, the movie with Mark Wahlberg the deep well, movie was amazing. Amazing movie. I had no desire to see it, but I watched it because it was on and I was on the sofa and I couldn’t go away from it. It was fantastic. Chris is also the boss at a consulting firm called Clearfield leadership, where he has been working for the last 13 years. Chris, welcome. How you doing? I’m doing great today. Jim, how are you? I’m great. Did you see the deep water? Well, movie, yeah, I

28:13 Chris Clearfield : don’t remember what it was called, but yes, I Yeah, no. I mean it was, it was, it was powerful.

28:20 Jim Beach : I enjoyed it. I thought it was really good. I like Mark Wahlberg anyway, yeah, what did you study at Harvard? What is your science?

28:31 Chris Clearfield : I studied physics and biochem, and with with a kind of, like smattering of neuroscience and computer science, and with that,

28:38 Jim Beach : very interesting, all right, you are damn smart, then we’ll just leave it at that. You help entrepreneurs get above the chaos and scale with clarity and lead with attitude and altitude. Aren’t we the biggest problem in our own success? Yeah.

28:57 Chris Clearfield : And I, you know, I the answer to that is yes. And I say that yes with a lot of compassion, because yes, we are the biggest problem to our success. And our problem is sort of well meaning. I mean, what I see happens with entrepreneurs is the stuff that they needed to be doing at the beginning of their business, the stuff that they you know, the stuff that helped their business grow. They get to a certain point, they get to a plateau and and that that does not help anymore. You know, their their tendency to solve problems, their desire to drive perfection and things, or their tendency to put themselves at the center of everything, at the beginning, that’s good, and that’s kind of fuel for progress, but at some point that really starts to hold them and their companies back.

29:45 Jim Beach : Yes, I agree with that. I was at Coca Cola for a short while, and my mentor there, after he told me he was firing me, said it’s all up to you what you are holding yourself back. You have to stop. Yeah, is that part of the high altitude entrepreneur? What is that framework?

30:04 Chris Clearfield : Yeah, the high altitude entrepreneur is, is, is the high altitude framework, which is kind of what the book is organized around, is really a systematic way for entrepreneurs to see themselves and their leadership patterns and also their businesses in a different way. And I think the key observation is that it’s only once we have awareness of where we are and how we’re operating now and why we’re operating the way we’re operating. It’s only when we have that awareness that we’re actually able to change

30:37 Jim Beach : and shift. So I’m kind of balding on the top, and I can’t see it without two mirrors, right? Isn’t it the same when we’re looking at our skill set? Don’t we need an outside view to truly understand ourselves,

30:51 Chris Clearfield : yes and yes, and sometimes that outside view can be a person, can be a coach and like when I’m when I’m coaching entrepreneurs. I mean, that’s a tremendous part of the value that that I’m providing just a different perspective. And sometimes that outside view can be like your two mirrors. It can be a tool. And so, you know, part of what the part of what I do as a coach is I support people to see themselves in their situation differently, and that’s really what I embedded in the framework in the book. It’s really a way of seeing your business from a different perspective, by getting yourself kind of out from being trapped in the dynamics to seeing the dynamics from the outside. So it’s a way of, sort of catalyzing you as an entrepreneur to make that shift yourself.

31:45 Jim Beach : Okay, you know, I’m just thinking back on my entrepreneurial career, once you’ve made a million dollars, though you’re too egotistical to do that,

31:56 Chris Clearfield : well maybe, I mean, it’s sort of, you know, it’s sort of, it sort of depends on what you want, right? Like, for some entrepreneurs, when, when they’ve, you know, when they’ve made their first million, they feel like they’ve made it and and, you know, they’re, they’re set, and they’re happy, and they’re kind of going forward. But more often, what I see is that entrepreneurs maybe look successful on paper, they have a sense of success. You know, they have a team, they have the revenue, they have a company, they have product market fit. And things seem like, from the outside, they’re going really well, but on the inside, they’re really they’re really struggling. They’re feeling burnt out, they’re feeling isolated, they’re feeling alone, they’re feeling like they have this tremendous weight of responsibility for their, you know, their companies, their family, their livelihood, and then their people who they pay and, you know, provide, provide their livelihood for so I think that success isn’t about the money. I mean, look, the money helps and it’s important, and it’s part of the currency of being on entrepreneur, but we’ve also got to be able to engage in the pursuit of our own happiness within entrepreneurship, or it’s just not worth it. It’s just like, it’s like an unstable job with a terrible boss, namely that bosses ourselves.

33:19 Jim Beach : Yes, yes. Yes. Do you find that there are plateaus, maybe two and a half million and that they get stuck and then maybe Nine 10 million, they get stuck again?

33:29 Chris Clearfield : Yeah, you know, I see there’s definitely plateaus. It’s not always straightforward. What the like, what the revenue number is, right? Because every, every industry is really different. And I work with entrepreneurs, you know, from property management to manufacturing to, you know, providing services to big industrial companies, so all across the spectrum. So it can really look, you know, that revenue around your plateau is really, is really different, depending on the industry. But, but what I see very much is there is a there is a mindset plateau. And what I really specialize in is I really specialize in entrepreneurs making that first shift from, hey, I’ve got a successful business. You know, maybe it makes a million and a half dollars a year. Maybe it makes $7 million a year. But I’m, I’m I’m constrained by my business. I’m working for my business instead of my business, working for my life.

34:27 Jim Beach : All right, a minute ago, you were talking about the tension, the stress, the decision making. That’s hard. So at like 2727 years old, I had to tell a 45 year old man to move take his kids out of school and move here to work with me. It was hard as hell for me to do that. I procrastinated, and procrastin was just afraid to pull the rip cord on his life and those kids dropping them out of school. How do you handle a situation like that without being stressed out?

35:01 Chris Clearfield : Yeah, well, I think the first thing I’ll say, Jim is, I mean, the stress, like, I think it’s, it’s powerful that you are aware of the stress, right? The stress can be a roadmap, that there’s something, it’s kind of a pointer that there’s, hey, there’s something important here. And, you know, no look, nobody likes to give bad news, right? You know, no, nobody likes to tell somebody they have to move. Tell somebody hey, we’re not going to be working together anymore. I think the the thing that I see with with entrepreneurs, is really a tension between, Hey, are you leaning into the relationship right now, or are you leaning into a performance question right now? Are you leaning into something strategic, something that are the goals of the business? And what I have found is that’s not an either or question. The more time you spend building a relationship with your team, building a relationship with somebody, building trust, the more you can ask them strategically, and you can even tell someone something very strategic, like, Hey, we’re not going to be working together anymore in a way that actually builds The relationship, because you’ve been spending time on that foundation. So the stress is very, very natural, and I think it’s one of the most challenging things for for entrepreneurs. And, you know, we’re really not taught to relate to people in this way that is both relational and strategic, and that’s, that’s, that’s a skill, and that’s a practice that we can be in.

36:42 Jim Beach : So your book has a methodology, right? Steps, yes, should we go through those steps? Yeah, that sounds great one. Wow.

36:57 Chris Clearfield : Jim, you’re, you have, you’ve done this before. This is not your first rodeo. Yeah. So, there’s so the Well, can I, can I start with the kind of anti thesis of the book a little bit. Yeah, so, so, so the anti thesis of the book, really, that’s the silly way of saying, like, the pattern that many entrepreneurs are in is something that I call the low altitude cycle, where some kind of trigger, some kind of problem, lands on their desk, and it creates a sense of stress, it creates a sense of urgency. And that can lead to really, what that leads to is some kind of reaction, right, either procrastination, in some cases, or, you know, a sort of reactive problem solving. But the problem with that, the challenge with that, is that that reactive problem solving ends up creating more stress, right? Whether it’s procrastination or you’re you’re stepping in and changing something, you end up creating more chaos down the road because you’re just solving the symptom, and you’re solving it from a place of stress. And what the neuroscience shows is that when you’re operating from a place of stress, you’re not you’re not thinking at your best, you don’t have access to the prefrontal cortex. And so this is the problem solving loop, which I call the low altitude cycle that many entrepreneurs find themselves in. So let me just pause there. I mean is that, does that dynamic, like you were just talking about, you know, the stress you had and procrastinating like, does that dynamic? Have you noticed that dynamic in other parts of your, of your entrepreneurship,

38:37 Jim Beach : you know, that horrible joke Chris about the problem with drunk drivers is that they don’t learn to drive drunk. Yeah, so not a good joke. Barry macabre, not a good joke. But I in graduate school, I had a roommate, and we were number one and two in the whole school, and we were very, very competitive, and eventually we got to the point where we were competing. And to make it fairer and more interesting, I was not allowed to start a project until he was done with it. Okay? I learned procrastination, you know, at the master’s level, and I was able to learn how that was not stressful to me. Procrastination does not cause me stress. Interesting, because I learned, you know, I did it for years. You know, I’ve always been a procrastinator, and so now I’ve learned that that’s actually one of my super strengths. I think, you know, Mark would spend four weeks and I’d spend four hours, and we get the same damn grade.

39:39 Chris Clearfield : Interesting, interesting. Well, you know, I kind of love the way you frame that, because, you know, procrastination, it really can be a superpower, right? And, and that, that kind of, that sort of brings me to the framework, because the book is really about how so many times entrepreneurs, something lands on. Desk, and they treat it like a problem to solve and they need to. They sort of move to push it out, or, you know, they take ownership of it. They take responsibility for it. And the the that’s really that makes a lot of sense when you are early in a business. That makes a lot of sense when you are are just getting started, and you’re, you know, your hustle is the fuel for growth. But as your business matures, your job as an entrepreneur shifts from solving problems to really being in a constant negotiation around what you’re giving up and what you’re gaining with each choice. And so the first step in the high altitude framework is all about just naming the tension that you’re in, whether that is a leadership tension between control and delegation, or it is a tension between urgency versus strategic focus, or it is a tension in your business, like, Are you building customized solutions for clients, or are you scalable? The first step is really just to name the tension that you’re in so you can kind of see the landscape that you’re navigating on. And this is powerful, because most of the time, for most entrepreneurs, they are in attention, but they are navigating it implicitly. They are implicitly leaning into one side of it control urgency or customization. Just as as as an example, it could be either side, but usually at the beginning of a business, people are leaning into control urgency and customization. And at some point that’s got to change, and you’ve got to start negotiating that with some consciousness.

41:43 Jim Beach : Okay, what is power tension?

41:48 Chris Clearfield : Yeah, so that really the there are loads of tension in every business, right? The power tension is the kind of core tension of the business. It’s the one that other things sort of orbit around. So if you’re if you want a team that takes ownership, but, but you are a leader that is constantly leaning into control, then control versus delegation would be your power attention, and it’s importantly, it’s also something that’s in your control. So, you know, there’s a lot of stuff in our businesses that aren’t in our control, but, the first step is to find and name your your power tension. And then once you’ve done that, we map it out right? Once you’ve done that, you look at the upsides and downsides of orienting towards control versus the upsides and downsides of orienting towards delegation in this example, and by really articulating those, you start to see that you’re not kind of trapped in one side of the dynamic, but you can actually negotiate, navigate that dynamic with with skill. Does that? Does that? Does that make sense?

42:55 Jim Beach : Yes, it does. And you call that clarity with attention map, right? Yeah, that’s exactly right, yeah. Is it 1x Y, Z, course,43:07 Chris Clearfield : yeah, it’s, it’s an, it’s a two by two, right? So it’s like, the simplest possible map you could build. Right on one side is control, with the upside and downsides. On the other side is delegation and and then with, you know, with that, yeah, what we’ve what we’ve got is we’ve now got, we’ve now got clarity. We’ve now got the ability to, yeah, really, really see, really, see clearly what the landscape is. So we can, we can know where to we can know where to navigate,

43:39 Jim Beach : all right. And then the third step, you use that map to create super choices.

43:47 Chris Clearfield : Yeah, exactly. And so, so super choices is, you know, let’s talk about, let’s talk about customization versus scalability. I was talking with an entrepreneur the other day who, who has a business that is all built around, all built around customization, right? He builds kind of custom, like industrial installations for companies. And it’s a business, you know? It’s at the heart of what his business is. And he is finding that that ability that need to do, to customize everything is now what’s limiting is growth, right? So for the first phase, it was what was driving his growth, and now it’s what’s limiting his growth. And so, yeah, and so. And so he’s kind of wrestling with this and and what we were talking about is like, look, you know, this isn’t a hard cut off, right? Like, it’s not like, Hey, today, you’re doing everything customized, and tomorrow you’re going to be scalable again. His job as the entrepreneur, as the founder, is to navigate this tension, navigate and recognize that he’s in a negotiation between giving up and gaining something, no matter where he is on this spectrum between customization and scalability. So the. The designing super choices. It’s a it’s a design thinking process that is embedded in the book. That is the question of which is really like, how might we capture as many of the upsides of customization and as many of the upsides of scalability while minimizing the downsides of both? And it’s, it’s not just a question for, you know, it’s not a question that has a single answer. But what it does is it, it creates some design opportunities for, oh, could we offer customized solutions in this way, but put a stronger process behind it in this way? So it’s really, again, it’s like, it’s, it’s not like we’re picking one point to be on this spectrum, but we’re rather designing the best place that serves our business and serves ourselves in our life in the best way that we can. So it’s this process of designing, really designing these super

45:55 Jim Beach : choices, all right, so I would create a non custom version as well increase the price on the customized version and sell customized for really high and non customized for lower, and scale

46:11 Chris Clearfield : that right? So that is, you know, that is an example of the kind of like back of the envelope design choice. And I think what’s exciting about the process of creating super choices is it gets really nuanced, and it gets really nuanced for your business. So for example, what what this entrepreneur is doing is they are starting to lean into building basically a productized service that is a standard design service for clients that they can do on the front end. So it’s kind of fixed price. It’s easy for the clients to understand, and it gets them to the point where they can have a real sense of, oh, here’s the design we’d be moving forward with. And then this company can also do the custom fabrication behind that, but that’s on the on the back of a very standardized and scalable process that they can sell much more easily. And it is almost like getting paid for business development. So it’s, it’s kind of an amazingly like sophisticated way of navigating this tension, and something like that comes out of this process of super choices.

47:21 Jim Beach : The book is called the high altitude entrepreneur, a framework for scaling smarter, leading better and living freer. I want to switch the conversation now a little bit. Chris, you’re an entrepreneur. What was it like 13 years to go out and create your own firm? How do you market? How do you do you have to raise money? Talk to us about birthing a business.

47:41 Chris Clearfield : Yeah, it was confusing. That’s the, that’s the easy answer. You know, I, I set out on this journey thinking that I had something to offer in a way that is totally different than what I am doing now. So I, I was really, like a really a baby entrepreneur. I didn’t raise money. I built everything in a bootstrapped way. And that tends to be true for most of the clients I work with. We’re not, you know, kind of like VC backed tech businesses, but but rather sort of organically grown, kind of like Main Street, you know, Main Street entrepreneur businesses. For me, it was this process of just continual learning. And, you know, I knew I had something to say. I knew I had some experience from my days on Wall Street and, you know, looking at things like the Deepwater Horizon, the BP accident that we talked about earlier, and I didn’t know exactly where those were going to land and and what I what I realized that was really a turning point for me and my business, which I think is something that’s important for all entrepreneurs to realize, is that in order to invest in the business, we’ve got to invest in ourselves, like we are the business. So we’ve got to look towards ourselves. We’ve got to look inward, understand what our barriers are, so we can change the business in a way that works for us.

49:10 Jim Beach : All right. How do you market these days?

49:14 Chris Clearfield : These date? Well, the book, I mean, the book is, you know, not only an asset that really is designed to be impactful. For entrepreneurs, it’s an asset that is designed for them to connect with me and to, you know, get a sense of, hey, here’s what, here’s what I stand for. Here’s what my here’s what my approach is. So for me, the book is a big part of it. And then, you know, I, I my, my stand in the world. My mission is to make the world of entrepreneurship more joyful, humane and effective, because I think we often set those we often think of those as separate things, but I think they go together to actually enhance the experience of entrepreneurs and to grow their businesses. And so I’m constantly talking with people about how they can do that.

50:06 Jim Beach : Excellent, excellent. And where do most of your customers come from? Word of mouth.

50:13 Chris Clearfield : We’re, you know, I have a, yeah, a strong, strong referral network. And then a lot of customers come from engaging with the book, engaging with the material, you know, finding some of my teachings online and getting connected that way. Every month, I run a kind of open round table for entrepreneurs. It’s sort of a group coaching session called Elevate, where we really take this process that we’ve been talking about, about like, how to see the tensions in your business, how to see your own contribution to them, and we we put that into practice in a kind of learning group that that’s another thing that I have found that I think is is under seen by entrepreneurs, that the you know, we can go out, we can read things, we can consume a bunch of podcasts. That is great. But the way we really start to shift things is we start to bring those things into our bodies, and we start to, yeah, we start to bring those things into our bodies, and we start to embody them through practice.

51:16 Jim Beach : I love it, Chris, how do we find out more? Follow you online, get a copy of the book.

51:21 Chris Clearfield : The best place to go is to high altitude book. Calm if you go to high altitudebook.com. Right now, I’m giving away the first three chapters of the book so you can download those. You can, you know, see if this, if this resonates with you, if you relate to it, learn more about the framework. And you know, just in those first three chapters, you’ll start to see how you can see your business differently. I mean, the book is really it’s a tool and it’s a framework, but it’s really a way to shift your perspective and see your business and see your role in the business in a very different way.

51:56 Jim Beach : All right, fantastic, Chris, thank you so much for being with us, and we’d love to have you back.

52:01 Chris Clearfield : Yeah, thanks, Jim. I really, I enjoyed this conversation. It was really interesting to kind of tap into your experiences and have you bring those in, and it gave us a lot to reflect on. So I really appreciated that, and it made me feel energized and engaged. So thank

52:16 Jim Beach : you. Well, thank you. You know I was listening to you.

52:19 Chris Clearfield : Yes, I knew you were listening to me. Yeah, we were, we were in a conversation. You weren’t, you know, you weren’t just reading questions off a sheet and kind of and, and sort of, yeah, there was a dialog. There was an energy that I really appreciated.

52:32 Jim Beach : So I, 10 years ago, was doing a radio interview, and it was two parts with commercial in the middle, a fox blonde first, and then one of the Fox old men second, and the blonde read word for word, questions. 123, off the sheet that I had sent her into dance. We went to commercial. Came back, the old man fox came on. He read questions one, two and three, word for word. Also, that’s

53:01 Chris Clearfield : pretty funny. How’d you handle that?

53:03 Jim Beach : That’s pretty funny. Hard, you know, because I gave my best answer to the woman, and then I had, like, pull out a second answer out of my took us, you know, here’s the other answer that I didn’t give. It was really hard,

53:16 Chris Clearfield : right, right, right, right. That’s so that’s so interesting. It’s such a tricky spot to be in, right? Because, you know, you want to, you want to. I mean, you don’t want to, you want to support people in saving face, right? And you want to, you want to deliver something that’s of quality to their audience. So, yeah, that’s a that’s, that’s almost like, you know, like the publicity toward nightmare, right? Like I can imagine, you know, like, that’s the dream you wake up with. They just kept asking me the same question. I had to answer it over and over. Mr.53:46 Jim Beach : Clearfield, thank you so much for being with us, and we are out of time for today, but back tomorrow. Be safe, take care and go make a million dollars. Bye.