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Index/Startups & Founders/Beyond 8 Figures
Beyond 8 Figures artwork

How to Think Like a Strategic CEO with Bruce Eckfeldt

Beyond 8 Figures · 2025-08-06 · 36 min

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Bruce Eckfeldt brings over 15 years of entrepreneurial experience, multiple exits in the mid-seven figures, and deep expertise in coaching high-growth companies. His approach differs from traditional frameworks like EOS or Scaling Up by combining elements from lean-agile methodology, three-horizon planning, and practical exit strategy work into intensive, company-specific engagements rather than lengthy multi-year implementations. Rather than adopting rigid systems wholesale, Eckfeldt uses a three-day intensive strategy session to rapidly surface organizational gaps and create actionable quarterly roadmaps aligned with 3-year vision. He identifies three critical business phases: establishing repeatable revenue models (1-5M range), scaling leadership and operations (the tough 2M to 10M transition where most founders struggle), and exit preparation or succession planning. The host and Eckfeldt discuss how the move from 2-7 million revenue is particularly challenging because founders must transition from operator mindset to CEO thinking - a dialectical shift requiring simultaneous focus on long-term positioning and short-term execution. Ideal clients recognize their own blind spots, value external frameworks, and see coaching as de-risking rapid growth; they typically operate in dynamic markets where the pace of change makes 18-24 month implementation cycles obsolete.

Key takeaways

  • →The 2-7 million revenue range represents the critical first scaling challenge where founders must build actual leadership teams rather than relying on functional heads reporting to the CEO.
  • →Three-day intensive strategy sessions can establish 3-year plans while identifying immediate 90-day priorities and emerging risks, avoiding the obsolescence that occurs when 18-24 month implementation cycles span market shifts.
  • →Founders must develop dialectical thinking - simultaneously managing long-term strategic positioning and short-term execution opportunities - to effectively scale beyond the operator mindset.
  • →High-growth company scaling success requires identifying and de-risking specific vulnerabilities like client concentration, talent gaps, and process misalignment before they become catastrophic.
  • →The best coaching clients are those who recognize their blind spots, understand the ROI of external frameworks (seeking 5-10x return), and operate in markets with genuine above-organic growth opportunities.

Guests

Bruce Eckfeldt

Topics in this episode

MetronomicsLeadership team developmentClient concentration riskExit strategyEosfounder-to-CEO transitionScaling UpThree Horizon Guarantee (3HAG)Lean-Agile methodologyDialectical thinking

Questions this episode answers

What's the biggest challenge companies face when scaling from 2 million to 10 million in revenue?

The lack of an actual leadership team - most founders have functional heads reporting directly to them but aren't operating as an aligned leadership team, and founders haven't yet transitioned from operator to CEO thinking.

How does Bruce's three-day intensive strategy session differ from EOS or Scaling Up implementations?

Instead of taking 18-24 months to work through a system that may become outdated, the three-day session establishes a complete 3-year framework, identifies gaps, defines 90-day priorities, and teaches the system so the team can continuously update it as market conditions change.

What type of business owner benefits most from strategic coaching?

Founders in high-growth markets (growing faster than 10-15% annually) who recognize their blind spots, value external frameworks with proven ROI, and want to de-risk rapid scaling by learning from patterns seen across multiple companies.

What is dialectical thinking and why does it matter for scaling?

Dialectical thinking is managing two seemingly opposing concepts simultaneously - in this case, balancing long-term 3-year strategic positioning with immediate short-term opportunities and risks that need to be addressed in the next 90 days.

What are common risks that emerge when scaling that can be identified early?

Client concentration risk (losing one major customer could be catastrophic), talent/process misalignment with new revenue scale, and emerging market risks requiring preventative moves even if they temporarily reduce revenue.

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Share of words spoken

  • Speaker A65%
  • Speaker B35%

Most-used words

team21three20different18start18couple17together16coaching15process15exit14opportunity14type13strategy12help12programs12growth12back11

Episode notes

Success doesn’t come from working harder, it comes from thinking differently . In this episode, I talk with Bruce Eckfeldt, strategic coach and 5x Inc. 500 founder, about how to shift from founder mode to CEO-level thinking. If you’re feeling the strain of growth and wondering why your business feels harder at $7M than it did at $1M, Bruce breaks down how to restructure your team, planning, and priorities to build something sustainable. What we cover: What separates founders from strategic CEOs The building blocks of scalable, sellable businesses Why a 3-day strategy sprint can reveal your biggest blind spots How to start thinking - and acting - for your business’s long game Want to lead like a real CEO, not just the person putting out fires? Let’s talk. Work with A.J. Resources & Guest Links: Bruce Eckfeldt: Website , LinkedIn , Instagram

Full transcript

36 min

Transcribed and scored by The B2B Podcast Index.

Speaker A: I realized the power of nature, of being outdoors, of the environment, of just wilderness, this kind of awe inspiring kind of impact it can have on you. My business originally I came out of this lean, agile environment. I just, I have this amalgam of different kind of tools and perspectives that I can kind of pull together in something that is kind of the best of breeds. You know, it's, you need to have something working pretty well to get to a couple million. To go from a couple million to kind of break that 10 million is kind of the first big challenge I find typically there I find there's no real leadership team in place yet.

Speaker B: I got lucky mf m that I was able to exit in the mid sevens and I was able to walk away. But still I did every mistake on the planet. Hey everyone. Welcome back to another episode. Today's gonna be a little bit fun. I've known today's guest for over 15 years. We were both in inks magazines 500 I think at the same time. I think it was his second or third time. It was my first and we got involved in a couple similar business groups both around um, the New York City tech scene and I was tech adjacent and so yeah, we've known him and Bruce has done a lot of amazing things. He's had a couple of really good exits so it'll be fun to kind of hear about a lot of his past. But he is doing every coaching program in the planet so I'm going to give him a little hard time in a second. Really just some interesting things in helping entrepreneurs grow and sort of position their business for the long term or the exit. And you know he has a, happens to have a pretty cool podcast at the same time. So I think we're going to have a lot of fun. Bruce, welcome to the show. Thank you so much for coming on today.

Speaker A: Thank you. It's been a pleasure and I'm excited to be here. And yeah, I've been reflecting too on I was trying to do the math and I think uh, it's got to be at least 15 years.

Speaker B: If I remember correctly after what was the storm that hit New York, you came to the fundraiser we held down in my offices in Dumbo because Dumbo had gotten hit and I think you didn't you buy the surf. The uh, the surf guys had raffled all or donated a c. Uh, it

Speaker A: was a Weldon mini magic.

Speaker B: Yeah.

Speaker A: I can't remember what the bid was or everything but I still have it. My, my son's used.

Speaker B: Oh good. Because I Was about to say, I've never been able to use a short board. I'm a longboard for life because one, I'm a kind of built like a tank and there's a ward that goes in front of that. Uh, but yeah, I'm a big long rectangle, you know, and everything. But I was la at that. It was like, wow, I'm never going to get up on a short board.

Speaker A: It's a challenge. It was, it's a, it's a fun board. But yeah, it's a little different than the long board.

Speaker B: I just kind of like so glossed over all the things that you've done. I remember when you had the company, you sold the company, you advise back and forth all the different pieces. Where are you in this journey right now? You know, coaching, doing all. What's going on with you? Where are you?

Speaker A: Yeah, yeah, it's been a really interesting and I often say circuitous kind of journey and path but on. Because I, I started like, I started as an archite, right. Like I had no initial ambitions of being an entrepreneur or a business owner and really, you know, took, I got recruited to New York to work with interactive media because of my architecture and 3D modeling background. And that got me into software development and uh, that founded the tech company I was in the lean Agile software development. So we got into software methodology and organizational transformation. And, and I think the kind of the thread that I found in all of the work that I've done is, you know, looking at kind of performance, kind of problem solving in different types of environments. So, you know, architecture was obviously bricks and mortar and technology became kind of the bits and bytes in user interface design and product strategy. And then it was software development and teams and how they're going to work together. And then, you know, once I sold my business, I did a couple of executive roles and saw my value as being able to come into situations and kind of quickly size things up in terms of all right, what's working, what's not working and where are we aligned and not aligned and where's kind of the bigger picture opportunity. And that's what kind of got me into coaching. Right. I saw that I could, I could come into the situation and create some pretty quick value around where the opportunity, what opportunities were being missed, where we had lack of alignment and then really facilitate the process, uh, as a coach to help the team see those opportunities have the conversation they need to have, really create that set of priorities, that vision for the future and set of priorities and then execute as a high performance team. And that's evolved over the last decade in terms of the types of companies I work with and exactly how I engage. And M, you mentioned the long list of kind of programs that I kind of do that under and we can talk about how those have evolved. And I think that big one or the two big things that I've uh, focused on the last couple years, one is really kind of driving all the way to the exit process, um, my own exit. And having worked with several companies through the exit process, I just see how important some of the earlier decisions that a company makes around, I mean everything from just structure and data management and you know, kind of organizational stuff to strategic decisions to hiring, to uh, roles and responsibilities that ultimately will drive not only valuation but really the complexity of the sale process itself. Just the uh, what I call the drama around sales that I've begun, uh, to kind of tool a lot of the work that I do. You know, even if we're three, four, five years out, there are things we can do to kind of make this more possible, more valuable and less dramatic. So I'm starting to work more on that. And then for some companies, like I'm getting involved, you know, pretty close to the exit and helping them through the process. So that's one. And then I'm getting into retreats, which is more of a personal passion that I'm now kind of integrating these various parts of my life into to something that's a little more cohesive and quite honestly fun for me.

Speaker B: Well, you know, definitely when we get into the discussion around preparing for exit, that's always the most painful for me because since doing these shows and talking to people who have spent the time either working on their own exit or offering services and kind of pointing out where to put the effort. I mean I got lucky, lucky mf uh, that I was able to exit in the mid sevens and I was able to walk away, but still I did. Every mistake m on the planet is kind of the way I look at it. In hindsight I'm like oh my God. And just the pain and just the lack or the loss of value from not being intelligent and not planning is something that, you know, I constantly, you know, will say this is. I just got very lucky. So I always find this, this kind of conversation fascinating. Why don't we talk? Because I think about a few months ago I was trying to get you back. All right, it's probably half a year ago to a year ago. I have kids. So everything three months is like three Months, four years. What's the difference?

Speaker A: Double it in real time.

Speaker B: We were talking about getting you on the show. I was asking about this or that, scaling up, because I was looking at implementing possibly EOS or something at a company I was looking to acquire. And you were like, well, I'm moving to kind of combine and go past just anyone specific. So maybe let's go into how you look at the coaching programs. Not like, why you joined or this, but like, I always feel like there's a. They all are very interesting, but they all have, like, either very, very similar or like just this slight little rigid difference of, um, vocabulary different or cadence. And I'm like, well, so how did you sort of come to what you're doing now based on.

Speaker A: Yeah, it was. There's kind of two questions or two factors there that I've grappled with over the years as I've kind of, you know, built the programs that I've built and built the kind of coaching models that I. That I use with my clients. One is, you know, each one of these, uh, systems, whether it's EOS or Scaling up or Metronomics, three Hag or MAP or. I can't remember what else is out there that you say Pinnacle, I think, is the new one that's out there. Yeah, um, you know, they're all designed to be, and some more so than others, designed to be a fairly fixed system that a large number of people can use. And in there there's always going to be, you know, a little bit of regression to the mean, a little bit of, hey, like, we need to create frameworks, tools, structures, rhythms, things like that that are going to work for lots and lots of people. There's a kind of a loss of specificity or a loss of being able to really tackle specific cases because, you know, they've had to kind of genericize them. You have a lot of coaches or a lot of people need to be able to use them. So at some level, they have to be a little simplified. Right. They have to be kind of brought down to a level where a lot of people can understand them quickly. So for me, as I've used these tools, I, uh, used them in my business, as I've used them as a coach over the years, like, I've seen and kind of advanced some of these things a little bit more for my coaching style. The companies I work with, you know, the way in which I work with companies. Another one that I find is a lot of these programs are kind of. We've got a Model. We're going to work you through the model over a series of quarters and eventually you'll have kind of the full system. What I found myself in is a lot of position with high growth companies that were in pretty dynamic markets and you know, if we took a year or 18 months or 24 months to kind of work through the system, by the end the world was so changed we had to start over. So the pace of change in the market and the page change into the business was such that we couldn't sort of keep up. So I've done two things. One is create something that's a little bit more specific to the types of companies that I work with and the ways that I coach. I've made them much more intensive based. Rather than taking many quarters, many years to go through the system, I go through the system very quickly in intensive. So I do like a three day strategy session. I'm going down to Panama on Monday to work with a company for a couple of days where we're literally pulling together the team and we're going through the core pieces of the entire framework in three days. What I tell them is, look, we're going to, whatever we create in three days is going to be horribly wrong. But what we're going to know is where all the gaps are and what do we need to start filling in. And you're going to learn the framework so that quickly we can put in the new pieces, we can update the piece that we didn't know, cascade it through the system quickly and get to a new quarterly plan or a new roadmap which will inform clarity plan. So it's really been those things. And then also I've just realized like I've worked with scaling up, I've worked with 3HAG, I work with the EOS and my business originally I came out of this lean agile environment. I just, I have this amalgam of different kind of tools and perspectives that I can kind of pull together in something that is kind of the best of breed a lot of these things. And again that, that fits with my coaching style and the way I kind of work with clients and the types of clients I work with.

Speaker B: Okay, let's talk about the type of clients because this type of environment, I've seen all the research, you know, oh, uh, the benefits of having EOs, the benefits of working with this one. And then you get into religious wars of, you know, well, you used your left hand. No, you're supposed to use your right hand. Really, I'm not going to Throw in Christian theology into this. Like in just kind of talking about this, do you see that there's a type of business or a point in a business's development that your approach is now starting to resonate or have a better impact for?

Speaker A: Yeah, I mean this somewhat explains I think kind of the different programs that I've put together because I find that they're kind of phases or stages of a company. You know, in the first stage I generally don't work a lot with early stage startups where we're really kind of figuring out problem solution fit or kind of market fit kind of issues. Usually I'm getting involved as like hey, we, we've, we clearly are solving a problem that's valuable to the market. Maybe we're struggling with monetizing it or optimizing the monetization side. You know, we've got something going. And so that first phase is how do I really get that business into a position of creating m repeatable sales and revenue going. And so that's kind of this early stage I typically find that's in the 1 to $5 million range, right? Like you can kind of scrape together a million dollars. You know, it's, you need to have something working pretty well to get to a couple million. But there's often this, that, that is a tough to go from a couple million to kind of break that. 10 million is kind of the first big challenge I find. So I've got to do some work there. Typically there I find there's no real leadership team in place yet. You may have a couple of functional heads around a uh, founder or a CEO and he relying on m some of those people, but they're really not operating a leadership team. So that's really one of the first things that I do is how do we get that business running on a consistent basis and put together leadership. That next phase is really about growth. Right. So now that we've got a successful leadership team, we're evolving strategy, we're evolving sales, we're evolving marketing, we're evolving operations and we're evolving the leadership capacity. And there's a, there's a series of changes that need to have happen not only in the company, but in leadership in terms of how they think, how they work together. I do a whole program on uh, going from founder to CEO and helping leaders inside those businesses really think like a CEO rather than a founder. And they're quite different. And if you don't make that jump, it will really hold you back. Then the last stage is really this exit, which is, okay, I've scaled. I'm now thinking about, like, I always joke, like, you're going to exit business one way or another. It might be feet first, but, you know, you can't stay in this forever. That starts to hit and they start to think about, okay, and it might be 10 years, right? It might be like, hey, I want to do this for another 10 years. It might be five, it might be two. But we need to start thinking a little bit either about how we're going to exit or how we're going to. What is the succession plan? Right? Like, are you going to turn this over to the next generation? You have, you know, if there's a family business, do you have people, Are there people inside leadership right now that would like to take this over? Do you want to do a management buyout? Uh, do you want to do an esop? Um, right. So there's lots of different possibilities here, but that's where this conversation comes, is where are we going to go? And that will help us with the strategy side and how we're going to scale the company. Um, if we have a better sense of that.

Speaker B: Sounds a lot like what you try and do is make sure the business is functioning on a strong basis and then start looking a little ahead and getting ahead of the curve on this. And, yeah, it's funny, when I was running a business, like, every time I heard stuff, I was like, all right, well, what do I do now? And now it's like a step setting back. The people who have these more intelligent approaches seems to be very much like, all right, just get your shit together and then kind of start asking questions that are going to help you look at, uh, possibilities into the future and how you can start preparing now to take care of it. You talked a little bit about sort of where you have to be on that growth, because we were in the INC business group for a while together, and I remember they bought the research team that had built some software for that book Crossing the Chasm. And they had that, like, really basic software of like, where's your team feeling today? Where is this? And it had, like, all this. And they were constantly pitching that, and it was just like, you know, yes, it's something really important. I'm messing, uh, everything up, and you guys would probably help me, but, God, this is just the worst software I've ever seen in my life. So, no, I'm not going to spend the 2,000amonth you want for this. You talked about that phase that, you know, that complexity you're increasing the amount of moving parts. Your cash flow is not, you know, growing to, at least at this point for the type of talent you need to handle this, you start moving past that, you help them figure out that process. Is there besides that type of phasing and structure and where they are in their. Is there a type of business owner, entrepreneur that kind of fits more to this type of, you know, your process here?

Speaker A: Uh, yes, uh, there, I will say there's types of business owners that kind of typically fall into these situations. And then there's the type that I typically work with, I think the type that fall into the situation. There's an opportunity to grow at more than a kind of a natural organic pace. Uh, and usually that's. There's market dynamics, there's market opportunity, there's some kind of innovation, something that means like we can probably do better than 10 to 15% growth a year. When you're talking about growing at a faster pace than that, the moving pieces, the risk, the complexity, the rate of change is going to be such that opportunities for support, right? There's an opportunity to kind of get ahead of this and try to de risk the situation and really trying to make sure you're taking advantage of that. A restaurant or something who's just kind of doing their thing and they're growing and maybe they're thinking about opening another location in a couple years. I would call that just kind of natural organic growth that doesn't need the kind of systems, strategy, rhythms, frameworks and stuff that we do as strategic and strategic coaching. The flip side is the things I look for in a client, they're really looking for outside help that is going to help them primarily with blind spots, right? They know that, hey, like I'm in the soup and it doesn't matter how smart I am, it doesn't matter how hard I work. I can't look at myself the same way as someone from the outside can come and look at. So they understand, appreciate and really see that as valuable. That want some type of proven framework, right. That they're. They realize that yeah, we could roll our own here, like we could figure this out on our own. But acquiring or bringing in a tool set a framework, a system that they can start applying right away is going to be advantageous, right? It's going to. The speed it increases their growth by generates enough value there. Like I do a whole value analysis of saying, look what you're going to pay me versus what you're going to, what we're going to Gain in terms of bottom line should be 5 to 10x. Right. So we should be able to do that analysis and say, like, if we're able to achieve these growth numbers and these profit numbers, like what you pay me is, is uh, a fraction of what it's going to generate. So they need to be. They see that calculation, they see the benefit that the last one is they want to de. Risk the situation. Right. Uh, that they know that having, you know, another experienced person on board who, you know, has a different way of thinking, a different perspective, has worked with lots of companies in these situations, has kind of seen the patterns, has seen some of the pitfalls companies have gotten and you know, can reduce the chances of those in a non, uh, trivial way. Like that is valuable to them. Right. So that's, you know, when I'm looking at situations, you know, what kind of client are they in? And then, you know, in terms of who typically I work with and I create value with, those are the, those are the things that come up when

Speaker B: someone is engaging sort of in that middle. You know, let's just say they're in the mid sevens, you know, they're in that thing. The opportunity to grow. Like, I remember a lot of times it was based upon the talent I had. I didn't have the appropriate processes or have processes built for, for a smaller part of the business. When I had taken a breath and then all of a sudden was like, wait, we're 8 million. How come everything's rocky? Oh, I'm running like a $2 million business. What is sort of that you jump start, as you said, three, three days, kind of like boot camp. Let's hit these things, let's cascade into the system, see where things move. But what's that expectation? Is it like, okay, you come in first three months, we're just setting the basis, we're kind of popping. Or are you sh. Are there some benefits right away other than, oh my God, I got to move faster? What's that sort of time frame that people start seeing the benefit of what could happen? Not like, oh, I'm getting more money, but like, oh, things are moving in this smoother way.

Speaker A: I like to talk a lot, a lot about dialectical thinking. You know, having to, uh, being able to kind of manage two concepts at the same time effectively. A lot of what I'm doing with teams is trying to help them think both long term, like, where do we need to be in three years and what are the moves we need to make to make three years successful?

Speaker B: Yeah.

Speaker A: But also what do we need to do today? Like what is the problem we need to solve? What is, what is the opportunity we need to take advantage of? It's always this interplay between short term opportunities and long term opportunities. And how do we uh, balance these? Like when I come out with the three day program is a three year plan, but it also shows us what do we, what's going to come at us in the next couple of quarters, what do we need to do in the next 90 days? And sometimes that's fix things, sometimes that's, hey, look, there's an opportunity here. Like there's a movement in the market, there is an opportunity to take, capitalize on something. We should do that now. You know, sometimes it's like, hey, there's a significant risk coming at us in the next 12 months. We need to start making some moves now on this thing to de risk the situation. You know, sometimes it's, you know, we've got a really big client concentration, maybe it's fine, but that could be catastrophic if that flips. And you know, we, we need to have a plan sooner than rather than later, even if it costs us some revenue. Like, even if we have to kind of pull back a little bit on something. Those are kind of things we're identifying and figuring out how to action.

Speaker B: As someone who's lost uh, two thirds of his business from a single client just changing over cmos. Yeah, that is definitely uh, something you need to plan ahead of time for, not the morning after when you've recovering from your hangover, from drinking yourself to sleep out of fear. Not that I've ever experienced that. I like this a lot because this is what I do a lot from a marketing point of view. And we've been, what I've been helping a lot of teams do is transition from a temporary fractional CMO to a longer term marketing capability. And what I always tell them, it's like, look, if we can't get the foundation, your analytics, your workflow processes around marketing execution, you're never going to be able to do anything cool, fancy or fast growth because it's just going to be one, spaghetti against a wall and two, you're going to make too many incremental mistakes trying just to get this done. So I like this slow, steady build from there. Is this you moving them from like, all right, let's set the stage, let's understand, let's look at the long term. Do you then continue working all the way through to that potential long term thing? What's that kind of the relationship ongoing.

Speaker A: Yeah, I would say there's kind of three types of engagements I get involved in. Sometimes I'm getting hired just to do three day, right. And they, you know, they go through the strategy framework, we come up with a 12 quarter roadmap. They've got a good understanding of their positioning and they feel confident with executing and they take it from there. Maybe they call me up when they need kind of help, ad hoc support around it. I would say that's probably about a third of the engagements that I get involved in. Then about a third are. We're doing a multi year engagement where we're doing a three year plan, a three day session to develop a three year plan. And then we've, we're coming in, I'm coming in quarterly, I've got a two day quarterly planning process which updates strategy, does a retrospective, works through issues, does some team development. We set the 90 day plan, we do a 13 week race. Right. So I've got a fairly involved quarterly planning process to help the team really update strategy and take that strategy to drive the execution process on the uh, leadership team. Then the final third are companies where we're working on those things and exits and other team development and kind of broader opportunities where it's, it's, it's a much more kind of nuanced and, and oftentimes there, there's, we're going in with the idea of okay, yes, we're exiting in three years, right. So we have, we need the strategy, we need the quarterly planning and we need the exit prep. Prepping the company, prepping the founder, he or she just like making sure that they have a plan. Personally, um, I find that's one of the big factors of a successful exit is do they have a plan, what they're going to do afterwards? And really positioning and managing the deal team as during the process.

Speaker B: I like that. And before we kind of get into the, I want to get a little bit into the retreats, but why don't we talk a little bit about, about sort of the mindset and the questions that you know, the entrepreneur, you know, the business owner should be having. When they're looking at your type of service, you talked about like, okay, they have this aspirational growth. They realize they're in an opportunity where if they were able to get their act together, and I'm going to oversimplify this greatly, they know they can grow more than just organically. So you know, what are the things they should be thinking about? How should they be thinking about choosing you going about this process, what goes in from their point of view, do you think?

Speaker A: Couple things that sort of generally recommend to founders to CEOs when they're thinking about coaching, obviously thinking about the framework, where are they as a business and what is the appropriate framework. So kind of making sure that they are, they're a fit to what the framework and what the program is going to help them do. Figuring out the kind uh, of type of coach that they're looking for. Right. So I, I generally focus or position myself as a strategic coach. There are other coaches that are much more accountability focused. Right. Like they're out there. Okay, did you get it done? Right. Like they're driving kind of execution process. You know, for me, if you don't get something done, we're going to have a conversation, we're going to figure out why. Right. And we're going to get to the root cause and we're going to think. But I, I want people who are fairly self motivated in terms of the discipline side of things. They can struggle and we can talk about it. But I'm not, look, I generally don't want to be in situations where I'm kind of the hammer, trying to get things done like they should, they should be able to get things done. So you need to decide what you need and some people need that. Right. So you need to kind of figure out what type of coaching do you want. And then the last one, which I think is the most important is like how to develop enough rapport and trust within a coaching relationship where you're willing as a client, you're willing to actually bring the big issues. Right. If you're, if you don't feel safe, if you don't feel enough, you know, kind of trust and rapport with uh, a coach to be able to say, hey look, this is really what's happening, or this is really what I'm struggling with. We're never going to be able to generate significant results. Right. So you have to be, be willing to be vulnerable enough with whoever you're going to work with to be able to do that. And that might look very different from different people.

Speaker B: Let's get in that. Because that to me resonates a lot because it's so hard. There's a gazillion coaches. What do you think those that you have the best relationship, what do you think the entrepreneurs brought to evaluate you and to develop, what did they do to first evaluate you, but then to develop that trust with you.

Speaker A: So I think the evaluation is asking me about My experience, one of the reasons I'm a coach is I made a lot of bad mistakes as an entrepreneur and I feel like, hey, let's not make those mistakes, right? So willing to kind of actually talk about my own experiences and you, uh, know, an open, honest conversation about the things I've learned, sometimes the hard way. I think the other one is folks that get to me through some kind of trusted third party, whether it's someone I've worked with or someone I've known or someone that, you know, even was an employee of mine at one point or like those kind of, kind of referrals, you know, are huge in terms of just getting us, getting a um, huge step forward in that. And I do a lot of, okay, you know, let's do something together, right? Let's do a half a day, let's do a day, let's tackle a problem, let's spend some time together and actually work on something. I find fairly quickly, once we start engaging in a couple of things and we start developing the rapport, we start actually getting into the issues, we start seeing some opportunities, we start developing some actions, that is probably the best way that I've seen to kind of get us to the point of, okay, now we can kind of get deeper and now we can kind of go down a couple of levels and really get to the, some of the issues.

Speaker B: No, I like that approach. All right, I want to talk about your retreats because one, they just are pretty cool. But what I like is you, you know, you talk about how you bring more into it, you bring more of yourself than just your strategy background and stuff. We had lost track after that, sort of the INC business group, whatever, and you came to that fundraiser we had done for the flood in Dumbo and you had become this complete yogi and you know, you were having a late in life child, uh, if I remember correctly. But like I uh, was just like holy. You know, you had been sort of like I was at the time, a sort of okay shape but kind of, you know, probably drinking too much, a little unhealthy on the edges, you know, entrepreneur pasty, a little soft, but not too soft, but just, you know, whatever what you bring into these retreats, because I know it is all about, you know, not just mental and the strategy and the business, but this whole like kind of bringing the whole life structure into the point.

Speaker A: I've had. I mean a couple of things happen for me over the years. I mean always been a big outdoors guy. I grew up in Minnesota. My father kind of took us camping and hunting and fishing. And I had this early in life and then I kind of lost it or I just didn't do much of it. And so later in life I kind of got back into it and I just, I realized the, the power of nature, of being outdoors, of the environment, of just wilderness, this kind of awe inspiring kind of impact it can have on you. So that became a threat and I started leaning into that more. So I think that's one area too is I'd always been an athlete and I'd involved in all sorts of different sports and not only just competitive, but competitive with myself and just kind of being able to kind of use a, uh, sport and athletics as a tool for kind of discipline and goal setting and accomplishment. And I got back into that. So I was getting into, back into triathlon and some other programs. The other piece, I started doing a bunch of men's work, right. Like I started really kind of getting into just, you know, everything from kind of mental health to kind of really kind of little soul searching about okay, what is, what is my existence, what is my purpose, what does it mean to be a man? And, and just being more open to really having some of these conversations and questions. And then eventually actually we got into psychedelics. So I run a podcast on the psychedelic space and stuff and that was fascinating. And um, and so a lot of these kind of came together and realizing ultimately that our kind of growth and change and development comes through some kind of challenge and discomfort and you know, a little bit of forcing us to rethink certain things. And so, uh, all these things were kind of going on in my life separately and I was, I've been doing my coaching and you know, working with businesses and I felt like I was very successful in terms of the intellectual side of things like being able to work with the team and kind of work them through. But I saw another opportunity of being able to take this one step farther has really helped them really transform as individuals in a team using some of these other tools. So the retreats that I've been focusing on the last couple years and we've got a new retreat business that is coming out called Trailblazers, which is going to be taking these opportunities to put people in a different context, you know, in some kind of outdoor wilderness, naturey kind of, and getting basically m out of the conference room m and giving some kind of challenge, a little discomfort, potentially a lot of discomfort in some cases. And as individuals and teams giving them an opportunity to really rethink some of their behaviors, their patterns, their thinking, their goals, and then we can come back and apply that to the business, you know, so sometimes it's a really kind of simple of getting a different spot so they just think differently. Sometimes, you know, we're putting on ropes on the side of the mountain, and, you know, they get very uncomfortable, and they have to deal with it as a team, and how do I perform as a team in these situations? And then we can take that back into the business and say, okay, now how do we deal with this? How does it inform how we need to perform and interact as a team to be successful?

Speaker B: I'm just, um, already thinking, like, how much prep would I get ahead of time just to be able to handle all this? But no, I do like that because I do think more and more, as I've kind of dove into trying to better understand the entrepreneurial journey myself, is how much it is everything we bring to the table, not just you get kind of in this mindset, especially when I think we're younger, of just like, I just got to build the business. Just got it, whatever it is. Yeah, I used to, like. It used to be a point of pride that I could just throw things on my shoulders. I would just be like, all right, whatever. I'll figure it out. And just. And then it's like, either I got old or eventually there was just one too many thing on my end. I broke. And that is, you know, the worst experience when you are doing something that is potentially so cool. Being an entrepreneur is this experience that's unlike anything. It's painful, it's uneven, but it is pretty much better than any other thing out there, in my opinion. So, yeah, I like, you know, your approach to kind of doing this. What do you want to do with this now? Moving forward, you have, you know, you have these coaching programs, you have the retreat. You're building this up. What's going to be your success as an entrepreneur now that you've had these exits, you've done all these things, you're quite familiar with all the different programs out there. I really should have bugged you earlier in AI, but, yeah, maybe I'll bug you on a future date getting into AI as a company. But what is going to be successful now for you as an entrepreneur?

Speaker A: So a lot of it is my focus is sort of building community, uh, in the sense of like. So a lot of the programs I'm doing now are group programs where it's not just about the tools and the frameworks and the coaching that I Give. But how do I create the right context and community around entrepreneurs to help them grow and scale not only businesses, but themselves? Um, the retreats are very much about how do we create connection between people and through these experiences, whether it's I'm taking a leadership team away or we're doing a YP or EO forum group, or whether I'm just open enrollment and how do we use each other and the experience that we have of interacting with each other as a tool for growth. And then ultimately, like a lot of the retreat platform is collaborating with other coaches, thought leaders, you know, people that have ideas, and actually partnering with them to put together these programs. So for me, it's less, you know, it's an opportunity to actually engage with other folks and being creative and collaborative and interactive with other, uh, people. Not just me in my head doing my coaching programs, but like, okay, what can we create together? And I, you know, I was an architect. I love, you know, kind of the creative, artistic aspects of this. Creating with other people is just a whole nother level. And so a lot of my excitement and the reason I'm kind of moving in these directions is creating more opportunities for myself around that.

Speaker B: Very cool. I can't wait to see more of what. It's been fascinating, you know, tracking and following you, and then every once in a while showing up some business event and seeing you with a team doing X, Y or Z. So I can't wait to see more of what's going to have the retreats. We've had a really great conversation, but I've been so fascinated, and I meant to bring this up earlier, going down rabbit holes around using AI to do different things and play with things. And I've been worried I've been spending too much. And I loved. Recently you had an Instagram post about understanding the difference between rat holes and rabbit holes. So not to add another new subject into this conversation, but I think that could be great in framing how to look at what you can do specifically around new technology, if you'd be interested in the future.

Speaker A: Yeah, happy to. It's a whole, that, that whole area of how. How do we, uh, predict where some of these things are going to go? How do we process some of these things? And you know, sometimes it's, hey, this is amazing opportunity. Sometimes it's like, you know what? This is half baked and we need to wait. Right? Like, it's just, it's not ready for us to actually leverage. But yeah, AI is one of those. I mean, there's a whole There's a whole group of these technologies that, you know, start to play out. But, yeah, it's. It's part of the growth process.

Speaker B: Cool. All right, Bruce, what's the best way for the listeners to, uh, find out more about you?

Speaker A: Easiest way, my website is My last name ekvelt.come e c k-f e l d t.com Just Bruceckfelt is my email address. I'm really big on LinkedIn, Beckfeld, LinkedIn.in Beckvelt, I think, is the URL. Find me there. I do a lot of content. I post just a lot of stuff there in terms of the work I'm doing, content I'm working on, you, uh, know, ideas that I'm developing. So, yeah, hit me up.

Speaker B: Right. And we'll have all those in the show notes in the email when this episode comes out in the socials. And I'll also make sure we include his Instagram because it's all tons and tons of great quotes, ideas, but specifically a lot about climbing, um, in it. So, um, I'll make sure they're all there. Um, Bruce, Bruce, thank you so much for coming. I really appreciate it. It's been good to talk to you. It's been a while.

Speaker A: It's been an absolute pleasure. Thanks, AJ.

Speaker B: Hey, everyone, thank you so much for listening today. Really. I think you should go check out Bruce's material. You know, follow him for a bit. I mean, his Inc. 500 articles, I've been really loving. Uh, he has a series of weekly newsletters that come out. I've been stealing stuff for journaling, quarterly planning information. Then, I mean, all stuff that I should have jumped into, but really cool stuff he shares around how to think about setting yourself up for future success, you know, is what we've been talking about in this. So go check out his material. I think you're going to learn a lot. All right, everyone, thank you so much for listening to today's episode. I'll talk with you soon. Bye. Bye.

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