← Confessions of an Implementer
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- [00:00]
A
I feel like there's this fancy gleaming surface layer thing where you look at entrepreneurship from an outside perspective. Like, oh my gosh, it's so, it's so lovely, isn't it? It's just so romantic. And anybody who's actually done any level of entrepreneurship, one business, two or ten. No, it's not, it's like dirty back alley fighting.
- [00:25]
B
Welcome to Confessions of an Implementer. I'm your host, Ryan Hogan. We share unique stories of EOS implementers and the companies they've transformed to give you a rare glimpse into the successes and challenges of the system in action. Let's jump in. I don't even know where to start your journey from entrepreneurship and founders and co founders and managing partners. It is an endless journey. And so where, where do you want to start in, in this journey?
- [00:56]
A
Well, I don't know. I'm a little conflicted because when I hear Confessions, I think of either Confessions of an economic hitman or I think of confessions with some kind of Catholic overtone.
- [01:07]
B
So I'm just a little, you know,
- [01:08]
A
nervous what I'm getting myself into, like, how deep are we going to go here, Orion? So with that, with that preface, we're probably going to talk about Eos at some point. So maybe how we all got here could, could be a reasonable starting point.
- [01:23]
B
Yeah, why, why don't, why don't we start there? I mean, I think what's, what's interesting, I, I, I'm assuming there's going to be some assumptions. I'm assuming like you discovered Eos as a part of some of this other journey. That was me. Eos changed my life. It was probably 2017. My first company had went bankrupt. The second company kind of took off and between Eos and Vistage, those were kind of two life changing things. Like what, what have you learned through this incredible entrepreneurial journey? And, and when I think of Confessions, I like to think about like, what are some things that you got wrong? And like sort of the confession and like, what was that nugget? What was that thing that you did differently from that point forward?
- [02:03]
A
I wish, I tell myself that I wish that I found EOs 15, 20, 20 years ago, before I made all the mistakes myself. But I don't know that I would have been in a ripe place to listen to anybody else but myself. In my 20s, I was quintessential startup guy, just hustling in my 20s and early 30s and starting businesses. Like I said, I blew up seven businesses in that time period. Four in a bad way and three in a good way. And the only reason that I had any success is because I, I kind of got lucky. I just, I figured out to do things I actually care about and focus on one thing at a time, which was incomprehensible to me my first, you know, five, six years. So skip ahead. I discovered EOS through, through my wife. She's a fractional CFO and half of her clients were running on this system and half were not. And flew out to some full day session in Kentucky and came back, told me to read a book and I was like, oh, awesome. This would have been great to know many years before.
- [03:12]
B
Yeah, that's, it's really interesting the way that you kind of framed the beginning of that of like, as much as you would have wanted to discover EOS maybe earlier on in life, it's like, maybe it wouldn't have been applicable. Maybe you would have been like in a mind frame where like, I know better. And, and that's, that's interesting because like, I was probably in that similar spot of like, I, I don't need other people to tell me what to do. I don't need a framework. Like, I can figure this out on my own. Was there, was there like a, a moment where that, And I'll give you my moment was like bankruptcy. And like, not only was it the business that went bankrupt, it was like the business took me under. Was. Was there a moment where whether it was ego or overconfidence or like, like I can figure this out on my own, where that just kind of went out the window?
- [04:01]
A
Yeah. Something jumps out at least. I mean, I got punched in the mouth multiple times and fell down, had to get back up. But I remember I was in, I was in a business, so. So it was in State Angels was my, one of my companies. We helped kids get in state tuition in any state and bootstrapped it to a dozen employees, you know, before I raised multiple rounds of investment, scaled it to 30 states and first phase of it was really fantastic and great when we were more localized and phase two was kind of like, let's bet it all, let's try to do it even bigger and let's scale it to the next level. And we just couldn't figure it out. And after a year or two of scraping and clawing and kind of hating myself in retrospect, I would get up and I would be active, not productive, and I would just put in these long hours. What was I even doing? You know? And like, I had all these stories that I was telling Myself, like, my employees will hate me, my clients will hate me. I can't stop this. I must force this. And you know, my investor, I'll ruin my name and my credibility in this. And at the time when I met my wife, I think before we were married, quite. And she's like, Jake, you're killing yourself. You're miserable. Like, what are you doing? Are you going to keep. How many more years are you going to keep trying to force this thing? Or it just doesn't feel like it's, it's catching at that for this level. And the moment that I allowed myself to even let that thought enter my brain that you don't have to do this, that's mixed with so much like, like failure and fear and like this, this talk track of like, no, you must, you must, you must. This ego thing. And like the moment I let that, that in and sat with it, I mean, I changed behavior and I said like, hey guys, this is what's happening. I don't think it's going to work. And we're cutting our losses and this is what we're doing for phase two of this business. There it is. What do you think? And to my surprise, everybody in my entire world was like, yeah, that makes sense. Hell of a, hell of an effort. Really good try. My employees were, yeah, yeah, we really gave it our. All my investors, I got messages from, from a couple of them that was, whatever you're doing next, sign me up, I want in for the next thing. Like, it takes a lot of grace to wind down a business and I didn't lose any friends. It was this, like, I was just telling myself, yeah, lies, lies. And after that, I ended up taking a six month sabbatical, went to Columbia for six, six or eight weeks with, with my future wife, Trinity, and cleared my head. And gosh, I could have told myself that same story for the rest of my life. Is it a long enough response for you?
- [06:50]
B
No, it is. And I think it's going to take us down an interesting path. One of the kind of talk tracks I'd like to stay on for this is this idea of scaling enterprises and raising money and things like that. Because what's interesting is it sounds like things were growing and doing great. You had some sort of hypothesis and had found some, some form of like product market fit. And then you tried to take it to the next level. Like, what were, what were some things that you were seeing where, like, like maybe it didn't scale as neatly as you thought. Maybe it was more complex. Like what were some things that you started seeing as, like, hey, you've got something and it's working and it's great. And then like, as you go to the next level, it's like, oh, shit, like, miscalculated.
- [07:37]
A
X. Well, maybe we could have figured out the, the product market fit on the, on the larger scale. If, If I look back now, I mean, with hindsight, I, I realized that it was just me and, and there was like, there's this. The words arrogance and hubris just come up in my mind as, like, as, as I look back and kind of judge my, my, my younger self. And it was all on me. It was like I was a. I didn't have a team. I didn't have a really. I had some department leaders, but it, it was a team of one. And how much can you figure out by yourself? Ultimately, it turns out, but I reached my limit and, and that was it. So I, I do wonder back, like, like, like thinking back, like, had I had a really strong team around me, you know, wouldn't have taken some outside perspective, like a friend or a loved one to say, hey, Jake, like, you don't, you don't see this blind spot? What if I had those people in my business?
- [08:30]
B
Did you wound up hiring, like, people that were close to you, whether it's friends or family, or did you at least have like, some arm's distance from. From some of them?
- [08:38]
A
Well, previously I did all kinds of businesses with, with my friends, and it turns out that hopefully they're listening. Remember how I did all the work, guys? Remember how I did? That's what it felt like anyway. So there wasn't like an equal distribution of, of effort. I felt like. So then I got to this place where I wasn't really trusting of, of other people. So it's just you learn something and then you overcorrect. And then you learn something and then you overcorrect.
- [09:12]
B
Yeah, it's like cyclic, man. That's exactly right. The, My first company that went, that went bankrupt. Like, a big part of that was because I hired all my best friends and like, they're great people. They're amazing human beings. It doesn't mean that they know how to scale an enterprise or how to lead or how to manage or there's some tough lessons learned.
- [09:35]
A
I so appreciate your willingness to just be forthright with, like, hey, I went bankrupt. Sometime I feel like there's this fancy gleaming surface layer thing where you look at entrepreneurship from an outside perspective. Like, oh my gosh, it's so it's so lovely, isn't it? It's just so romantic. And anybody who's actually done any level of entrepreneurship, one business, two or ten. No, it's not. It's like dirty back alley fighting.
- [10:01]
B
Like, yeah, you've, you've got to love the process. Like, like, you can chase money, you can chase passion. Like, like, you can find, you can find like some of the, the core reasons that you're doing it. But if you don't enjoy the actual process of building, I just don't think you'll make it. Because the, the whole thing that, at least that I found with entrepreneurship is like, you will make it whatever you're set out to accomplish. Like, you can accomplish those things. It's just, you can't predict the timing because the hard work and a little bit of luck and a little bit of all of these different things have to come together and to meet your odds improve over time because you're collecting experience, building a network, understanding frameworks and how to operate a business. But it doesn't mean, like, you won't get lucky in your 20s or, or like, figure it out in your 60s. But the thing is, like, if you don't deeply love the process and like, can't accept the, like, don't have a high risk tolerance because, like, you know, my last company could have bankrupted. Like, we were very close, like, basically that whole seven years. It's great to say, hey, we did $205 million over seven years. We grew from zero to 55 million in six years. Like, the, those are really cool things to say. You know what, like, people don't see is like, every single week we were trying to figure out how to make payroll. Every single week we were like, how are we going to fulfill this purchase order? So anyhow, that, that's a little bit
- [11:23]
A
of a tangent, but I appreciate the odds. Like, my, my takeaway from my entrepreneurial journey of seven businesses over, over 15 years was this. I mean, luck. Like, I remember I listened to what is it? How I built this sometime podcast.
- [11:39]
B
Yeah. Guy Ross. Yeah.
- [11:41]
A
And I mostly don't like it because at the end so many people are like, he always asks how much was luck part of the outcome? And some of the guests are like, you know, I worked really hard and I deserve it, and I have a noble blood in my veins. I'm like, no, man. There's so much like, please, like, luck and connections. Who. You know, like, I heard that growing up all the time. It's not what you do. It's who, you know, kind of thing. I was like, yeah, yeah, yeah. I got a really great idea. Business ideas are worth nothing. They're worth nothing. Like, oh, you have a pitch deck. Awesome, Great. How are you going to execute that? Who are you to do anything like that? What if something bad happens and not the regulation level? How are you going to go over that? Who do you know? So if only I knew, I would have done the exact same thing.
- [12:31]
B
That's, that's the other. That's why what you were talking about earlier, like, resonating so deep. Because I don't know if I would have implemented. Like, I'm the kind of guy, like, I've got to learn through some sort of experience and then like, and then I'll actually start listening or paying attention. But like in my. It was probably like 25 when run for your Lives took off and it was a zombie infested 5K obstacle course race. And like, everything was going great and it was scaling and. And I was like, it's all because of me. No, like, sometimes you just hit the right market at the right time and things take off and it's like, what are you going to do next? That decide kind of the fate of the business? And we didn't do. We didn't do the right things. Which is interesting.
- [13:14]
A
Yeah. What I still struggle with is this idea that your greatest strength is your greatest weakness. There's another side of every coin sort of thing. So it takes that type of. Maybe it does take a little arrogance. It takes some stubbornness to be the person that's going to even try to do anything Right. But it's also. So that's at its best, but at its worst, you don't listen to the thing that would help you. So like separating the signal versus the noise. I don't know the answer to it, honestly. I just know that it's really complicated.
- [13:43]
B
It's so interesting you said that because the kind of. The strength versus the weakness. I forget who I was talking to this probably a couple of months ago, but they talked about this idea of good ego and I had never looked at it like that. Maybe I just haven't spent enough time like looking at ego or studying ego and things like that. But we hear too often that ego, I mean, there's a book called Ego is the Enemy. Um, I think it's Ryan Holiday. So like, there's this notion that like ego is a bad thing. Um, but to your point, like, there's
- [14:10]
A
probably another book that's like, ego is your best friend. You know, there's a book for everything and there's an Internet article for it too, so.
- [14:15]
B
But sorry, someone's got a blog post. I 100% agree. And to your point though, like, you can't do. Elon came out, what, last year, and he was like, oh, did you expect I could do all these things? And I was like a normal person. Like, you cannot be a normal person and like, do those sorts of things. And there, there has to be, even if a little bit of like ego, bravado, confidence to believe in yourself enough to go do these ridiculous things.
- [14:41]
A
So, so from that, I'm a little jaded and cynical about the whole startup world being part of the Boulder startup scene for, for many years and going to lots of events. Like, I, I got to admit, I'm. I'm. Confession time. I'm just tired when, when somebody proposes to do their first business, as much as I'm like rooting, oh yeah, go do it. It's like, okay, you just had a wedding and now you're going to make an app about something with. And it's just like, what? Really? You know how many times I've heard that, that, that pitch? Like 30,000 times. So I'm to a point now where I work, I have respect for the people who started awesome. But if you don't make it through a couple existential crises, like, I don't know that us is the right thing for you. And I keep learning this lesson over and over again. Like, there's this kind of client profile for what will work with EOs, and every time I've strayed from it, it's. It's kind of the same story. It just, those are the times where it doesn't. Doesn't quite work. Like you get something out of it, but it's not the thing.
- [15:39]
B
So what is kind of that profile or where, where in that profile have you deviated a little bit and it's been like, not, not it.
- [15:47]
A
Well, I've got a few examples that come top my head.
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B
So.
- [15:50]
A
First one is not being in a team, a leadership team. And you don't know it yet maybe, but I remember working with this. We had our first day together, a full day session, and it was kind of took forever to kind of get it on the schedule. And it turns out that there were three senior people who actually made decisions, and then there were like three or four or five more junior people. And we had the full day session. We did the whole thing. And at the end of it, the visionary is. I heard this later, like the next day. Like, oh, you know, EOS is, it's really cute and you guys should totally do. I'm not going to do it. But you guys should all do it. Like, nope, that's not, that's not how it's going to, going to work here. Like if you're not fully bought in, then we're just wasting our time. So like that was the end of that relationship. So having a team is one. A lot of times cash flow is one of them. Like, EOS is a little bit more about optimizing your business. If you were still totally figuring it out, I don't know that you're ready. Like, go read, go retraction, go do a VTO by yourself. I wish I would have done that. Would have helped me not do a few businesses. But you really have to be past some existential crises like where you almost lost it and then you broke through a ceiling. Because you'll say like, oh, well, Jake costs money. I'm not going to pay this guy money. Like, I could buy more marketing. And a lot of times if you're under a million dollars in revenue, I would say don't spend money on me. Go, go, go put it in, in marketing. And then, and then the third one that I see is an unwillingness to change. They're doing it for appearances. They want their board to see that they're taking it really seriously. They have like an investor or something. They're placating the team and they're pretending that we're doing it together. And it's back to that first kind of lack of, of team.
- [17:46]
B
When I think about like the books and like the phases in which you read books. So for me, for instance, like pre product market fit, I'm all about the lean startup because like, you don't necessarily need to know how to run a business. All you need to know is like, how fast can I find like something that has enough value that somebody will bring money out? And then it's like once you've kind of refined that you found product market fit and like you now have a market to sell your product or service. Like then and only then do you have to start worrying about things outside of bringing in cash? You have to worry about systems and frameworks and worrying about like what cash is coming in, what cash is going out. You spoke a little bit about this, about this being jaded and it's interesting. Like, even for me, like I've been, I've been hearing a lot of like different ideas lately and Like, I'm kind of in, I'm kind of in your camp, which is like, it's been done before or like it's this or it's that. And like, it really comes down to the entrepreneur. And to me, it's like if the entrepreneur hasn't experienced like, adversity and like real adversity where like, they've built resilience because you're betting on the entrepreneur at that point. So like you're betting on their ability to be able to pivot and iterate fast enough to stay ahead of the market, stay ahead of the competitors, and like truly scale an organization. This is a hot take. But like, most 20 year olds don't have that yet. That's why I saw last week, it was like the average age of unicorn founders right now is like 43 years old. Go Ryan. Yeah. Yeah.
- [19:20]
A
Let's start our new unicorn.
- [19:22]
B
Right? That's it, man. But like, they've accumulated experience. I think you and I either become jaded or to a certain extent influence that. Like this is a young man's or young woman's game and it's not. But like, for some reason that's the perception.
- [19:36]
A
Well, yeah, yeah. What's. There's a, like a positivity bias though, with all the entrepreneurship stuff where you just see the, the lotto winners who, I did this and I didn't do anything and then look, I made a billion dollars. Oh, I'm great. You don't, you don't see the 900 failures broadcast like, hey, I went bankrupt. Like, I don't see that post, like, from you, Ryan. I bet you have that post.
- [20:00]
B
Yeah, yeah, I'll share it with you outside of this. I'll tag it in our post. And that's kind of the purpose of this podcast too, right? It's because I feel like all people see is the look at this person or look at this company and they don't see really what it takes. And I think all too often, not that this is information for people to take and not get involved in entrepreneurship, but I do think that entrepreneurship takes a certain human being. And like, if you don't understand what you're getting into, and very rarely do, I think like somebody can, can change like that part of themselves to be able to take that much pain because they want, like, they either have it or they don't, and maybe that's a hot take. And one of the things with this is like getting enough exposure out there for, for people to understand the, the road that they're going down and not to discourage but just so like there's eyes wide open of like it's going to be painful.
- [20:56]
A
Well, there's a little bit of like an arm length relationship I have with I, I don't, I don't really rub elbows with all the, the young or old, whatever entrepreneurs that are just trying it for their first time. I kind of select selection bias. I kind of wait for the ones that are at at least a million or 2 million or 3 million in revenue and those are the people that I end up talking, talking to and working with because necessarily they've gotten through some hurdles. They, they probably have a team around them. Then the fun part happens when you say great, let's grow up a little bit, let's make this a little bit more sophisticated. Like you were just winging it and shoot from the hip. That's awesome. There's art and there's science. What if we do. Let's just throw a little bit of science in there and see what happens.
- [21:37]
B
And the In State angels wasn't your first nor last company or entrepreneurship. So what happened after In State?
- [21:46]
A
Yeah, so I mean the first businesses I did kind of funny it was like I'm importing scooters from China and had no, I had no way to, we didn't know how to sell it and so we had, I spent months talking all these factories in China and we got this, all these college focus like telescopes and it was like bikes and scooters and with this big container full of stuff and we're like what will we do now? Like a garage sale on the hill and maybe made our money back sort of thing. What are we doing and like smoothie shops and bike sharing endeavor and just like yes, yes, yes, yes, yes. And I, I think it is cool like go mess it up in your 20s and but yeah remember I started focusing so I, I had success in iPhone apps, caught a wave there and real estate and State Angels, like that
- [22:44]
B
stuff doesn't just kind of go away like where today you are an EOS implementer which you're doing the Lord's work over there because it's like you're changing people's lives every day. And so like I guess what's, what's your vision? What's where, where are you, what do you, what are you up to?
- [23:10]
A
Well I guess here's what I tell myself. I think it's true. I keep saying it out loud and see seeing if it resonates still. But I really hate poorly run businesses. So the thought of Being able to help a business be successful one at a time kind of lights me up, right? Because it's not just the leadership team. Like there's some conference room of people. Like, that's not it. Like, look at all the employees in that company. Look at all the spouses and family of all those employees. Look at all of your clients who have either have a positive experience or a negative experience. Like, theoretically, I could be touching, you know, 10,000 souls if I'm working with a company just to make it a little bit better. 5% better, 10% better, 15% better. That feels nice. Because how many businesses have you dealt with like recently where you're like pulling your hair out, like, what are we doing? This is so inhuman. So maybe I'm a force of good in the entrepreneurial world. This is what I tell myself.
- [24:04]
B
Yeah, yeah, yeah. I mean, I had, I had long, long conversations with myself of like, you know, what's, what's kind of next after, after Talent Harbor. And again, like Visage and Eos were such big impacts that it was definitely, it was definitely a path.
- [24:24]
A
It is unbelievable how many people are getting away with it. Like, I look behind the curtain of all these companies, maybe it's not surprising to you, but a lot of companies are not that well run. Like, whoa, spoiler. Like they kind of, they figured it out somehow. Like there had to be a survivor and that's them. And there's a lot of good qualities in there, but there's just so many low hanging fruit opportunities to just, just, just be a little, a little better.
- [24:53]
B
I think about that all the, all the time. Actually, I was just talking to my business chair last week about it because we've, we've been on the hunt to acquire companies and we've been looking at a few. And what's really interesting is like, there are some companies out there that it's like in spite of their best efforts, they are successful. And it's like, you look at like how they're operating, you're like, how is, how is this even happening? And like, to a certain extent, it's also made me think about, you know, based upon the military and some of the other things that I've been through, I'm like, you know, I'd like to think that I run well oiled machines or at least like respectable organizations. Then I walk in others, I'm like, man, like, all the failure I've had, all the, all these different things, and this company is thriving right now and doesn't even know what they're doing. It's a really interesting witness.
- [25:42]
A
I think that the word that jumps out to me is it's something about intentionality, about purpose. I think that it's just happening to a lot of businesses, and they've just gotten into habits and routines, and it happens to be working for them. But I like to be this force of, let's have business on purpose instead of on accident. What would that look like? If you chose, like, you're not a victim here. Like, what do you want to do with this business? And talking to founders and owners and what the hell? What do you want out of this? And sometimes it's. I'm so burnt out. Help. I want to. I want to sell it for anything. Like, please, help, help, help. And I've worked with people like that, and, you know, a good outcome of that is I worked with somebody like that over a year, and I was like, hey, man, what do you think now? You still want to sell the business? And after working together for a year, it's like, why would I want to do that? This is great. I'm profitable. We're making money. I've got a team now. It's not just me on my shoulders. Awesome.
- [26:37]
B
Yeah, I hear that quite a bit. It's like, why would I ever sell? I'm sitting in a visionary seat, doing what I love and making money. You just said something really interesting. This whole idea of business on purpose, or the intentionality, what's kind of that? First thing, if you walk into an organization, you're like, holy crap. Like, what's. What's going on here? Like, how do you help them? How do you help them, like, understand intentionality or, like, what is business on purpose?
- [27:07]
A
So I think. I think half of what I do is EOs, and I like EOs. I'm biased. That's the chosen methodology that I prefer that I like. But the other half of the value that I think that I bring is. Is having the hard conversations that they're not gonna have without me. So, like, honestly, a big value add of, you know, working with a company, like, doing EOs, is getting them in a room, having them clear their schedule, and just having a space and a safe place to say, hey, take a breath, guys. We're gonna work on the business all day today. And there's some stuff that you're not willing to say yet. You're scared you'll say a lot, and you'll be pretty honest. But, like, there's. I bet there's, like, this next level of stuff that you're just not quite ready to get there. We don't have to get there today, but what if in the next one or two or three times that we see each other we just get a little bit closer to that and the moment we can really say what we really think out loud, it's going to be okay. That's my business thesis. Been doing this for like four or five years now. As a. All I do is EOS implementation.
- [28:13]
B
Right?
- [28:14]
A
That's, that's how I spend my professional life. And it's worked out so far. Not 100% and no guarantees, but that's my approach.
- [28:22]
B
All right, quick break friends. Do you find it impossible to hire and retain top sales talent or worse, are you paying insane recruiter fees who are all using outdated hiring processes? Yeah, I was too at Hunt a Killer. We were spending hundreds of thousands on recruiter agency fees. And after I sold that company in 2025, I started Talent Harbor. And the whole vision here was to make sales recruiting accessible to small and medium sized businesses. Because the organizations that can hire and retain world class people are the ones that ultimately win. Most organizations rely on things like ZipRecruiter or LinkedIn and they get hunted. Hundreds, if not thousands of resumes. But we find that the best salespeople are already perfectly placed somewhere else. And that's why our approach is to go after them. And we do that through a business model called recruiting As a service. We do not charge commissions, we do not have success fees, we don't have contracts, we don't have long term engagements. And we become an extension of your team as expert sales recruiters. If you're tired of the same old recruiters and want to actually grow your sales team, check us out@talent harbor.com. that's Talent Harbor. T A L E N T H A R B O R dot com. Let's get your next sales superstar hired. What is that moment? Is there something that you like see where it's like oh crap, it's, it's working like, like we are now having those conversations like what, what does that look like?
- [29:55]
A
Yeah, it's, it's the obvious thing that anything, anybody who walked in, who, who watched a team dynamic for five minutes, whatever that person would have seen, they all know it. As soon as somebody just broaches that thing and, and then I'm sitting there like oh really? Well, earth shattering really. That person's not the right. That one crazy. But, but they said it and they start talking about it and it doesn't have to be personal either. Like, sometimes it's just the person is
- [30:21]
B
in the wrong seat.
- [30:21]
A
It's like, hey, you. I've seen founders who want to be visionaries thrust into being the primary fundraiser, and they're just blowing their brains. I hate it. That's the last thing they want to do in the world. And it's just saying, like, what if. What if you didn't do that? What if we got a new CEO in here that loved that and that was their skill set? And they're like, oh, that was an option.
- [30:49]
B
Are there. Are there ways? Like. Like, when you're thinking about just thinking,
- [30:53]
A
like, sometimes it goes wrong, but, like, talk about that later.
- [30:57]
B
Well, here. Like, here. Let's go there now. Like, where? Where. Where. Where can it go wrong?
- [31:03]
A
Oh, I just remember working with success stories, too. I promise. I'm poking on the confession part of, like, you know, the times where it didn't go right. Well, actually, it did go right. I'm telling you. Sorry. So working with the company, they've been doing EOs themselves for. For years, right? And they want to bring in a professional. They want to have, like, one. They fly a bunch of people out to Colorado to, like, an Airbnb, and we're having this session, and they think that their EOS game is really tight, like, really strong, really good. And we start with basics of the accountability chart. Who does what here? Like, what do you do and what do you not do? And it's like half the day, and we're. There's like, seven people in the room, and for every single position that, like, we do the seats first. Structure first, people second. This is the structure. And I'm like, okay, marketing seat. Who. Who might be good at marketing? Every hand goes up. What sales seat? Who would be. Every hand goes up. Like, what? Every seat is like that. They're just throwing their hat in the ring for every single thing. Like, I want. I want the judgment. Like, tell me if I'd be good at this or not. Skip ahead. One of the guys doesn't have a seat, right? So, like, oh, so. And so I notice that it looks like you don't have a seat on a leadership team. I work with the leadership team usually. What do we do? And that's like, elephant in the room or entering the danger. And we're just staying calling a spade a spade. And this guy has a really. He freaks out. Like, he's. He's yelling, he's cursing. Super upset. He's accusing people. This is bullshit. Am I allowed to curse on this program? Maybe not yes, yes, of course. Oh, good. And he ends up walking out of the room. He gets in his rental Jeep and we don't know, like, oh, he'll be back in a little bit. He just broke off some steam. He ended up. He went to the airport and he flew away without a word. I think he left his stuff there too. And then, you know, they're yelling at each other that night like, what are you, Where'd you go the next day? We did two days. We come back and we say, you know what, I think we should tweak this accountability chart. We really need this person to be on the leadership. Oh wait, he left. If he would have just hung on for a day, he would have come back to his position on the leadership team. But it's also reflective of like he just wasn't with the greater good of the company in mind. I don't think he was a core values fit. And that came out. So is that a good outcome or a bad outcome? I don't know. It's a pretty aggressive outcome, isn't.
- [33:39]
B
Is. It's pretty aggressive. I was going to share a story. It's not nearly as like that one's a really good one because you were like, yeah, the team flew in, they knew what they were doing. And then it just kept getting worse and worse and that was our, our story. So like we had Dan, Dan Wallace was the one that came out to Seattle, did for my EO or for my Vistage group, like 20, 18, 19, 17 maybe. And then, and then we self implemented for a couple years and then we actually got Margaret Dixon who I'm sure you're familiar with because she's right.
- [34:11]
A
Boulder lover. Yeah.
- [34:12]
B
Yep. And she like we all flew in the Boulder. Cause we were headquartered in Baltimore and we had offices in Seattle. I was living in Seattle. So we flew in to Tamir and the first day she was like, you know, we were like, we've been self implementing for years and like first day we sit down, she's like, what the hell are you guys doing? But it was the same exact, same exact thing.
- [34:30]
A
We're crushing it. We're like, perfect. Probably your best client. Like, I don't even need you. Like, yeah, that's. That's shattered your reality. Yeah.
- [34:38]
B
Yes. Yeah, that's, that's exactly it.
- [34:41]
A
How did you, how did you take that? Were people able to, to stomach that or was there defensiveness?
- [34:47]
B
Yeah, I definitely defensiveness. Like I, I think what we really struggled, what we really struggled with at Hunt a killer was like my Old Vistage chair used to talk about this idea of, like, when you have your leadership team, you try and get everybody on the same. Same side of the table looking at the. The same problem. Because all too often what happens is you've got a problem, the problem's in the middle of the table, and everybody's sitting around a circular table and they're fighting about the problem. And you got to get everybody on the same side to understand, like, that problem is not anybody's problem. Like, specific problem. It is the company's problem. We have to resolve it together. And I think we struggle to do that. Like, you know, all too often the company thrived or died on paid advertising. So, like, when paid advertising wasn't optimized or ideal or customer acquisition cost was increasing, you know, that was a marketing problem, wasn't a product problem, wasn't an operations problem, everybody's like, hey, we're doing our job. Get CAC down so we can continue growing this thing.
- [35:47]
A
There's some element of truth to, To. To that, right? Like an element, at least.
- [35:51]
B
But yeah. Yep. And I, I think that's. That was probably our biggest. Our biggest issue was like, how do we. How do we get everybody? Like, it later became much other, much different things, like rowing in the same direction. We had. We had some leaders that were like, I don't know, like, on hole nine, while we're teeing off on hole one, we're like, hey, we're. We're over here. But I would say that was one of the hardest things for us.
- [36:18]
A
Yeah. I mean, it feels like this really simple idea, but what have we got together every quarter? And we had those hard conversations, guys, and got aligned as we could, and we went in that direction for any days. And, like, that's as simple as EOS is, in a way. I mean, there's more to it, nuance and such. But, like, nobody's doing that. Your competitors aren't doing that. As popular as EOS has become, you know, I mean, tens of thousands of companies working with an implementer kind of thing, there's millions of companies in America who are not. And then globally, I think it's a competitive advantage. I agree.
- [36:58]
B
And what, like, you know, when you talk about these hard conversations, you talked about kind of some of the breakthroughs, some of the funny breakthroughs. So, like, what are some of your. What are some of your methods? Like, how do you. It sounds like you now have a way which you can identify when that magic moment is happening. And it's like, all right, we're here. How do you help companies get to that moment where they're now comfortable being like, you know, hey, Rob, you know, I think in certain respects, like, you're, you're not the. You might not be the right person or whatever that conversation might be.
- [37:30]
A
It's a pretty flowy thing, right? Like, how does a poet make a great poem? How does an artist paint a great mural? Because all the greatest artists painted murals. Something that jump out to me are. I just. It's really fun for me, the confrontation. Maybe that's like a sociopathic kind of thing to say. But when all those people are in there, I'm like eating popcorn, watching the show, and I, I'm really excited. But sometimes I'll get scared or I'm like, as, as an, as an audience member to their conversation. Sometimes I'll say, oh, we're. Oh, that. That could be. Oh, if we said any more about that, that could be. And I'll poke the bear. And then there's also, I think that there's like an invitation, right? Like, hey, we're here to say what we really think. Okay, so just invitation to do that. I know it's scary. Like, I'm your training wheels, I'm your crutch. It's cool. Like, we can go there. There is no way companies go there without a third party, I don't think, unless they're really spiritually enlightened.
- [38:38]
B
I agree with, like, the, this whole notion of graduating. And I get it, I get it. Like, you know, a couple years with an implementer and you can be trained up in understanding how to navigate. The one thing that's IRreplaceable is that third party perspective. Like, we never, we never were able to have the conversations that we needed to have without a third party in the room. And whether it's like someone understanding the dynamics of the team or like you just said, let's almost like a coach, right? Like someone that's. That's willing to push you and continue pushing you. We never graduated. And that's because there is so much value that comes from, from like having a. I don't know, having an unbiased party in the room to be able to call out the, the bull crap.
- [39:24]
A
And that's not the necessary outcome of it. Like, I'm looking to work with companies for about two years and, you know, maybe you need somebody for two years and maybe you just want somebody after that or not. So, like, that's all right. Another thought, like, talking about method is I get bored really easily. And the moment I get bored,
- [39:48]
B
I
- [39:48]
A
feel like if I'm bored, somebody else is bored. So I try not to have that. So I move it along. And gosh, as I'm talking about it, it's like a really selfish expression, isn't it? Creativity.
- [40:00]
B
All the great artists were artists.
- [40:02]
A
I'm an EOS artist now.
- [40:04]
B
Yeah.
- [40:05]
A
See how much I've, I've grown into my humility. Can you imagine me as a 22 year old? It would have been. I.
- [40:15]
B
But the, there's a flip side to that. It goes back to your earlier point of like, you know, for all the grace, there's, there's, there's maybe some not so great, but like, you know, even, even the, the idea of, of like wanting to push people into the danger zone, whether it's entertainment or not, like they have to go there and like being able to like navigate those conversations and push the team to get uncomfortable, like, that's where it doesn't matter whether it was the Navy or companies or doing what I'm doing today. It's like, it's the uncomfortable moments that are generally the most valuable. I was cringing when you said that guy walked out and flew back home. I would have been like, oh, like, I would just felt so awkward in that moment. But you were probably just back there pushing it.
- [40:53]
A
I was secretly like, that was kind of awesome. Like, I'll tell the story on a nationally syndicated show with like some, some guy named Ryan. And five years from now, I know it, it's all building up to this man.
- [41:07]
B
Like, your email is. I can't, can't wait. You even sent me a little, little countdown clock. I, I loved it. What, what are some things that like, you see, you see, I, it's hard to say your clients get wrong because you've talked about this idea of like, some can't get out of their own way, some don't have the right leaders on the team. But like, are there some common themes as you're onboarding a client that's going to be a great client, where you're like, I know we're going to have these issues and you're trying to kind of get ahead of them.
- [41:36]
A
Elaborate on your question a little bit.
- [41:37]
B
I guess. Like, you know, we've talked a little bit about there's, there's not a team in place, they don't have the cash flow, there's better places to put it. So we've talked about like two or three different ideas where, where they might not be. The, the. A great ICP at this point, ideal client or. Yeah, but on the opposite spectrum, where, like, they are a great client, they're going to be a great client. Are there some common themes that you see inside the early days of the session room where you're like, these are some things, like, we need to get ahead of, and some things that you do to kind of help that team, I don't know, understand the why.
- [42:17]
A
So I guess what jumps out to me is I'm going to start on the not ideal case. Happens with some frequency. I do like to just say it like, hey, it's designed for this, and you're not that exactly. Maybe it's still beneficial for you. But, like, eyes wide open. If you go into this, this is the case, right? And then do what you will. And then every quarter, it's like, hey, are we sure? I'll check in. Are we sure this is what we want to be doing? Is this working? Is this the right stage? But on the other side of the spectrum, where it's somebody who's just like, yes, let's do it, I think the words that come to mind are, it's a team, and there's some humility there. And that's it, actually, those two characteristics. And, yeah, we're gonna do the work together. And then the team part, everybody takes as, like, they just check the box. Like, hey, are you a leadership team? Yes, of course I am.
- [43:19]
B
Yeah, check. But.
- [43:20]
A
But then with a little bit of prying, it's like, oh, I hear that guy talking all the time. So I'll say that kind of stuff, like, you know, gosh, we've been here for four hours. I think that, you know, this guy's talked for, like, three of them. What do we think about that?
- [43:35]
B
I'm assuming what. What. That's. And I guess it depends on who's the one that's talking a lot.
- [43:40]
A
It's the founder, it's the visionary. So that's what I'm the guess.
- [43:44]
B
Like, has that ever backfired on you or. Or most of the time it's like, all right, now we've cut through and we're. We're off to the races.
- [43:51]
A
Backfire how? Like, what's the worst thing that could happen by saying what. What we all are thinking? That's. That's my. That's my approach. So if it leads to, like, hey, Jake, you know, you're. I want to cuss a lot, and I'm only in session room once somebody has broken the seal. Well, I let out my true sailor here. But they're like, hey, you're being mean, Jake. Get out of here. I guess that's, that's an outcome that might happen that hasn't happened yet, but it will, I guess, I guess I'm intellectually okay with that. At the moment, I'll be crushed. But later I'll reflect and I'll be okay about it.
- [44:29]
B
I like that. I like that because maybe it comes down to delivery or like, who you are. Weren't you the class clown? We talked about that in our, in our pre call.
- [44:38]
A
Yeah, I grew up as a, as a class clown feasting after the attention of my fellow classmates.
- [44:44]
B
Did you play baseball as well?
- [44:46]
A
Baseball? Yep.
- [44:48]
B
Football, Basketball, Basically if I had a ball in it. You were, you were there. All right, class clown.
- [44:54]
A
And I mean, but to be honest though, I was only great at sports until eighth grade and then everybody had puberty and I didn't. So my, my high school career was not legendary.
- [45:08]
B
So humor replaced the athleticism.
- [45:10]
A
Is that, oh, that hurts. That cuts me, that realization. I haven't had it yet. You're good at this. You should be a DOS implementer.
- [45:17]
B
I, or podcast host. I like, I'm debating between the two. We're gonna figure it out. The other thing was I, I like to tell people that like I was a really good golfer. Like it, my grandfather raised me golfing and so from like 5 years old, had a golf club and like for a 10 year old, I was incredible. I was winning the three whole competitions. It was great. I like to say, like, I'm still like an incredible golfer for a 10 year old. So if you put me on the scale, yeah, I'm, I'm still really good. I, what, what, what I was getting at there is like maybe, maybe it's your, your delivery or, or tone or like your understanding of the situation, how to read it. Because like, you say something like that to the wrong person, that's ego driven. You know, an ego driven founder, ego driven entrepreneur. And they're like, well, of course I'm talking because I've got all the answers. But your ability to deliver something like that and like one, create a reflection moment for that individual. And two, being able to like open the room to the danger zone. I think that's pretty incredible.
- [46:19]
A
I'm not perfect. I'm just pretty well practiced. I used to moderate roundtables of entrepreneurs for many years with an organization called House of Genius just for the love of the game. So I kind of got some more moderator chops and we started in Boulder and we Ended up blowing that up to 30 cities and I think three continents over seven years. And I moderated hundreds of sessions and thousands of entrepreneurs. So there's a lot of practice there and I've made plenty of mistakes and I still do, honestly.
- [46:51]
B
Yeah. What is House of Genius? That's really interesting. You opened up the Colorado or Boulder chapter.
- [46:59]
A
Yeah, I was the founding moderator of it. I moderated the Boulder session. It was like three hours. You get together with a group of strangers, everybody's from a different background, but you're not allowed to, to rest on your laurels. So everybody's a stranger to each other. Like, you don't say, well, I'm, I'm Ryan and I have a, this awesome podcast and I had this business. We're like, whoa. So just like, like wow me with your, your content during, during the session. And your contributions don't rely on, on your, on your ego stuff. So, you know, maintain those rules. And we'd have presenters and they, they give a big problem. And you'd have a whole group of folks from different walks of life that would kind of weigh in there and challenge and poke and prod.
- [47:41]
B
Are these any problems? So this is.
- [47:43]
A
I'm surprised you didn't go to one, honestly.
- [47:46]
B
Well, now I'm like, now I'm deeply curious. Selfishly, like, I just, I, I want to know about these things. Is it, is it like entrepreneurial and business wise or. No, it's like, yeah. Anybody?
- [47:56]
A
It is.
- [47:56]
B
Okay, I'm going to check this out.
- [47:58]
A
And still it barely exists at this point. Maybe it'll be kicked off again. Like I was part of it for a seven year period and kind of stopped doing that to start doing eos and other stuff.
- [48:10]
B
Got it. So this was your, it sounds like you found a lot of passion, purpose, other things in like hosting and moderating these groups and communities. And then that was like, hey, eos, I can do this with different companies.
- [48:25]
A
And so many egos in that too. It's like there's some C level of Comcast that's in the room and there's some so and so who, you know, had some $50 million exit. There's like a grad student and a therapist and a psychic. You don't know anybody like what they are. The end, you do a reveal. It was really fun to figure out who they are.
- [48:46]
B
That's really cool. I'm, I'm, I'm going to check this out. What, what do you look for in a client? And I know we talked a little bit about this as far as like, you know, some of the three key things you don't look for and the ICP and stuff like that. But like you specifically, like what are you looking for in your clients? Do you focus on a specific like area, industry size, like what's, what's kind of your, your best client?
- [49:11]
A
Yeah, some people have, have niches and they only work in such and such industry. And there's pros and cons to that. I did a little analysis of all my clients after doing this for five years and I was looking for patterns and some kind of insight like what is, what is the thing? And I realized it's who, not what. I don't care what the people are doing, but the commonality between all the people that I've seen be really successful with Eos and that work with me. Anyway, there's kind of two things I've pulled out. So the who means that you're real, you're willing to be real. And I think you know what that word means. And if you don't know what that word means, then I'm not your guy. Maybe there's somebody else's. And then do you actually want to change? And most people would just automatically autopilot, say yes and yes, but with a little prodding, a little prying. Is that true? Are you sure? Really? Really, really? And the people that are willing to play that game with me and then bring in their team and just ask the question like, hey, there's this EOS thing. I don't know a ton about it, but let's learn about it together, like from the earliest stages. So I'm not coming in as like the mercenary of the founder. That doesn't work like, oh, here's Jake. To come in here and fire a bunch of people like, no, no, no, no. Let's come together really early. This is Eos. Does it make sense? Do you want to do it? Do you want to work together? And then I find that there's a lot of buy in when we go that route.
- [50:34]
B
Nice. And then geographically, I know it says virtual, so this is like a. But just for people that can't see the video or something like that. Like, like you're, you're across the us across the world?
- [50:47]
A
Not across the world. I'm not going to the other side of the earth. But I know people. I can connect you with somebody. So yeah, all over America, about half my clients are close to me. They're in Boulder, they're in. Nobody's in Nederland. I'm in Nederland Colorado. I'm looking for my first client up here. There's like 600 people that live in town. But yeah, Boulder, Denver, Colorado Springs, Fort Collins, kind of the Western Slope veil. Half of them are that and then roughly half are virtual because it's, it feels like it's becoming more and more common. You got a dispersed leadership team and it's very costly time, energy, money to, you know, gather the troops once everybody flies into Phoenix, into Denver, into wherever they are. So a lot, there's a lot of receptiveness to doing a virtual session. Like, let's be really effective and efficient. And most people are like, I can't do that. Kill me. Like eight hours on zoom. A common kind of wrap up at the end of a session that I do virtually will be something like, I was prepared for disaster. I was ready to just end it all before I came in here, but the time went fast and we got a ton of stuff done and I actually could keep going. That's a common response I hear from people. And then I travel sometimes, not too often, but I'll get on a plane. Sometimes I charge a little bit more. I like to keep it to one or two travel clients. Got it.
- [52:12]
B
Okay. I thought there was. I, I had a joke for the travel, for the getting on the plane. All right, here's, here's the, the, the ringer question, which is someone just listened to this whole thing and hopefully they got a lot out of this because I, I think the, the one thing that, that I probably didn't, I did more poorly than I didn't do your background justice on this. And so like, I would encourage anybody listening to this, like, go look up Jake Wells and like, look at the background because like my, and I'm biased because I, I've, I've lived through a lot of pains, a lot of scars, but I think the ones that have, like, lived through it are the ones that have some very unique perspectives to be able to bring to other businesses that are having similar challenges. So if someone just listened to this whole thing and said, holy crap, like, love Jake, I need some Jake in my life. I got to figure out how he can become my usi. How can they get a hold of you?
- [53:06]
A
Well, I am an accessible, real person that you could just pick up a phone and call if you want to. You could Google Jake Wells EOS and I think my website would probably pop up. But you could email me jake.wells osworldwide.com. that's probably good, right?
- [53:24]
B
Sweet. Let's do it. And I'll put a link in there. Jake, thank you. The time flies with this. We're already there. I appreciate you taking an hour, actually a couple hours at this point because of all the pre calls and fun emails out of your life to come on the show, share your journey. Yeah, man, thanks so much.
- [53:43]
A
Thanks for the free flowing, wide open conversation that we had. It was a lot of fun.
- [53:49]
B
We went all over the place. I appreciate it. Thanks.