Mastering Business Exits and Beyond With Bruce Eckfeldt of Eckfeldt & Associates

Bruce Eckfeldt is a Strategic Coach and Master Facilitator at Eckfeldt & Associates, where he works with CEOs and leadership teams to scale their businesses. As a former Inc. 500 Founder and CEO, he successfully scaled and sold his business. Bruce focuses on developing leadership skills, optimizing companies for transactions, and navigating mergers and acquisitions.

Here’s a glimpse of what you’ll learn:

• [03:32] Bruce Eckfeldt shares his background as an architect turned tech CEO and leadership coach
• [04:55] The springboard approach to business exits
• [07:04] Lessons Bruce wishes he knew before selling his company
• [09:18] The emotional impact of losing control after selling your business
• [12:30] Why founders often struggle with identity attachment to their companies
• [14:32] How building relationships outside the business can ease the exit process
• [20:55] Why Bruce recommends sharing all potential company risks upfront with buyers
• [23:56] Key risks of earnouts, deferred payments, and executive compensation packages
• [29:24] Examples of preparing assets and opportunities for life after the exit
• [34:00] Structuring deals to retain licensing and non-compete flexibility post-sale
• [41:40] How communication, alignment, and leadership challenges persist at every growth stage

In this episode…

Many business owners dream of a profitable exit, but few are prepared for the emotional, strategic, and operational complexities that come with selling a company. Beyond valuation, sellers often overlook the personal identity challenges, the intricacies of deal structures, and what life will look like post-exit. So, how can founders approach their business exits in a way that minimizes regret and maximizes future opportunities?

Leadership coach and former tech CEO Bruce Eckfeldt emphasizes the importance of reverse-engineering the exit process to align with long-term personal and professional goals. He advises founders to confront their emotional attachment to their businesses early and to develop networks and interests outside of work. He recommends proactively organizing company information and sharing all potential risks upfront to build buyer trust and streamline transactions. Bruce also highlights the need to carefully evaluate earnouts, deferred payments, and non-compete clauses to ensure the deal supports the seller’s next venture.

In this episode of the Inspired Insider Podcast, Dr. Jeremy Weisz interviews Bruce Eckfeldt, Founder of Eckfeldt & Associates, about planning business exits as a launchpad for future success. Bruce shares why treating exits as springboards leads to more fulfilling outcomes. He also discusses the pitfalls to avoid, how to prepare for post-sale life, and the psychology behind successful transitions.

Resources mentioned in this episode:

• Bruce Eckfeldt Website | LinkedIn
• Scaling Up Services

Special Mention(s):

• Scaling Up: How a Few Companies Make It…and Why the Rest Don’t by Verne Harnish
• The Goal: 40th Anniversary Edition: A Process of Ongoing Improvement by Eliyahu M Goldratt and Jeff Cox
• To Sell Is Human: The Surprising Truth About Moving Others by Daniel H. Pink
• What Got You Here Won’t Get You There: How Successful People Become Even More Successful by Marshall Goldsmith and Mark Reiter
• Blue Ocean Strategy: How to Create Uncontested Market Space and Make Competition Irrelevant by W. Chan Kim and Renee Mauborgne
• Thinking in Bets: Making Smarter Decisions When You Don’t Have All the Facts by Annie Duke

Related episode(s):

• “How to Sell More And Save Time with Robert Hartline of Absolute Wireless” on the Inspired Insider Podcast
• “EO Tulsa | Real Estate Investment With Mat Zalk of Keyrenter Property Management” on the Inspired Insider Podcast
• “How to Craft a Compensation Plan that Attracts and Motivates the Right People For Your Company With Verne Harnish, Owner Scaling Up” on the Inspired Insider Podcast

Quotable Moments:

• “Rather than thinking about your exit as an ending, think about your exit as a springboard.”
• “The whole idea that you’re going to sit on a beach and drink piña coladas is fiction.”
• “Every business has skeletons. My suggestion is put all the skeletons in the closet up front.”
• “The challenge with communication is the illusion that it’s occurred.”
• “Growing a company is not purely additive; it’s as much about undoing strategies that no longer work.”

Action Steps:

1. Start with a clear vision of your post-exit life: Defining what you want after selling your company helps reverse-engineer an aligned exit strategy.
2. Build strong networks outside your business: Cultivating relationships beyond your company reduces emotional dependence and supports a smoother identity transition.
3. Organize and document company information proactively: Detailed, transparent records build buyer trust and can prevent valuation risks or failed deals.
4. Be upfront about company risks and challenges: Disclosing potential problems early builds credibility and prevents trust issues during negotiations and due diligence.
5. Evaluate earnouts and deferred payments carefully: Understanding the risks tied to post-sale compensation helps avoid financial disappointment and loss of control.

Episode Transcript

Intro: 00:00

You are listening to Inspired Insider with your host, Dr. Jeremy Weisz.

Dr. Jeremy Weisz: 00:22

Dr. Jeremy Weisz here, founder of Inspired Insider where I talk with inspirational entrepreneurs and leaders. Today is no different. I have Bruce Eckfeldt and you can check him out at Eckfeldt.com. I’m going to spell it for you because it’s not so intuitive, but it’s Eckfeldt.com. Bruce, I’m going to formally introduce you in a second, but I always like to point out other episodes of the podcast. People should check out some of my top favorites. You know, actually being you’re you’ve been very active in the EO universe, right.

And so Robert Hartline was a great one. He had a chain of you may know some of these people, actually a chain of cell phone stores that he built up. And he then also has a software called proof. I had Matt Zalk on who does property management all across Arkansas, Oklahoma and the surrounding areas there. Some other I had Verne Harnish who started EO actually and wrote Scaling Up, and I know Bruce is a big fan of Scaling Up and uses the methodologies there. You can check those out and more on inspiredinsider.com.

This episode is brought to you by Rise25 the Rise25. We help businesses give to and connect to their dream relationships and partnerships. We do it in two ways: one, we’re an easy button for a company to launch and run a podcast. We do the strategy, accountability, the full execution, and production. Number two. We’re also an easy button for a company’s gifting. So we make gifting and staying top of mind to clients, partners, prospects and even staff. From a culture perspective, all you do is give us a list of people. We’ll do everything else curate the gifts and the box and make sure it looks you know, your logos on everything, etc. you know, we call ourselves kind of the magic elves that run in the background to make it stress free for companies to build amazing relationships.

And I’ve found no better way over the past decade to profile people I admire and share. You know, what they’re working on my podcast and send them sweet treats in the mail. So check it out at Rise25 or email us at support at rise25.com I am super excited to introduce Bruce. Bruce Eckfeldt. He’s a former architect turned successful tech CEO who now coaches founders of high growth companies. Previously, he actually scaled a business onto the Inc. 500 list, 5000 list multiple times. Actually, you were on my business partner John Corcoran’s podcast and you actually had a lengthy discussion about that. It’s not easy to do because you need to grow. Yeah. Multiple times. And he had a successful exit. And he uses his experience in Scaling Up Three Hag lean agile methodologies to help leaders scale faster and exit bigger with less drama. And big thank you to Jerry nylons for actually connect. John Cornyn didn’t even connect those Jerry nylons did of trays press services. So Bruce, thanks for joining me.

Bruce Eckfeldt: 03:24

Yeah, thanks for having me Jeremy, I appreciate it.

Dr. Jeremy Weisz: 03:26

Tell I’m going to pull up your site in a second, but just tell people what you do.

Bruce Eckfeldt: 03:32

Yeah. So well today that’s changed over the years and over time. You know, my primary job is really focusing on founders working with them on scaling strategies. How do you go from a, you know, a couple million to a couple hundred million in revenue? And then ultimately, what is your exit look like, whether it’s financial or strategic or e-SOPs or, you know, figuring out that next chapter? You know, one of the things I’ve certainly learned in my own experience and then, you know, having worked with many founders on this process, is you really kind of need to figure out what’s next.

And once you kind of figure out what’s next, it gives you a lot of insight in terms of then what kind of exit you’re going to have. And then we can kind of define what kind of company you’re going to scale. So I end up kind of reverse engineering. A lot of this is really kind of having the discussion of what they want to do ultimately. And then how do we create the company that is going to get them there?

Dr. Jeremy Weisz: 04:23

We’ll talk about your exit and company, previous company in a second. But I know when you’re listening to this, the book may be out, it may not be out. Or maybe it’s coming out soon because it is coming out soon. But in our conversation. But you have a different take on exits. And so I don’t know if you have a title or working title that you can talk about. So we pointed. If not you can. We’re looking at your website here. You can go to their website.

Bruce Eckfeldt: 04:50

It will be on the website.

Dr. Jeremy Weisz: 04:51

I’m sure it’ll be on there. But talk about your different take on exits.

Bruce Eckfeldt: 04:55

Yeah. So the working title is called springboard. And it really is kind of this idea of rather thinking about your exit as an ending. Think about your exit as a springboard into the next thing. And so and really comes from my own experience in, through my kind of exit. And like I said, you know, many, many of the exits that I’ve worked on and founders that I’ve talked to that have gone through exits and, you know, the fact is, is, you know, I exited at that’s a good question. What did I exit? 40, 39, 38 even maybe I can’t remember. I’d have to do the math again to figure out the dates.

But you know, these are not and my you know, my exit was very, you know, very nice. But it wasn’t like I’m not going to work again and the rest of my life kind of thing. Right. Like it was an opportunity to cash out. It was an opportunity to kind of change a chapter. And honestly, I think most of the exits are like that, right? Yes. I’ve talked to a few people that have had, you know, $100 million exits and, you know, even there, although they’re totally financially secure, they don’t need to make another dollar. You know, the rest of their lives, they need to do something right. The whole idea that you’re going to sit on a beach and drink pina coladas is, you know, this idea that works for two weeks if you’re lucky.

And so you really need to have some kind of idea whether it’s because you need to make money or you just want to have, you know, a passion or you want to have an impact on the world. And so what I’ve really kind of looked at is the world of exit literature mostly is around transactions, mostly about valuation, mostly about the deal, very little about the what is next and how does that deal set you up for that strategically. So I end up doing a lot of work with not only thinking about what is the exit that you need, but what are the assets, what’s the reputation, what’s the network that you need. You know, pre-exit so that once you have your exit, you’re all set up and cued up and ready for the next thing and not sitting there flat footed, you know, wondering what to do next, and, you know, running into existential crisis, which which is not uncommon in those situations.

Dr. Jeremy Weisz: 06:55

What do you wish you would have known? I’m assuming this is one of those things, because oftentimes we write books for ourselves ten years ago.

Bruce Eckfeldt: 07:04

Yeah. So I think that the two things that I wish would have played out differently, I wish I would have done differently. One is kind of understanding why I was even in the company. Right? Because I think, you know, a lot of entrepreneurs end up in these companies kind of by happenstance, right? It’s a little bit of, well, you know, you know, I turn left and then this thing happened. And the next thing I know, I had a business, right. And so, you know, you kind of lose the sense of purpose, I think when you just start focusing on the company and why you. And I was an architect originally. I mean, I was not trained as a business person. I did not when my mother asked me what I wanted to do when I was young, I said I wanted to be an artist and marry a rich woman. Right. That was my strategy, right? So, like, I didn’t have.

Dr. Jeremy Weisz: 07:47

As a young age. Wow.

Bruce Eckfeldt: 07:48

Yeah, I was a rich woman.

Dr. Jeremy Weisz: 07:50

Actually. surprises me. The artist doesn’t surprise me.

Bruce Eckfeldt: 07:53

Well, I was passionate, but I was practical. Like, I knew that as an artist, I wouldn’t make any money. I needed a strategy there. But, you know, so I didn’t it wasn’t like I had these ambitions or this, you know, lifelong yearning to found a company and be a CEO and have this exit. And so as I got into it, like, I, I think I would have done, I think it would have been much easier for me and kind of figuring out what path I wanted to do, not only how I wanted to exit and what I wanted to do next, but really how I wanted to operate the company. Right. And I think a lot of what I ended up in, the situations I had this, you know, really nice company and we had some really great stuff, but not that it wasn’t happy, it just wasn’t aligned with really my core purpose. And you know, what I was good at and what I really loved to do. So I think that was number one.

Number two is I think I, you know, I certainly felt very stuck at the end of the business in that I didn’t feel like I had a whole lot of options. And so when the exit opportunity came up, it was kind of fortuitous. And it was kind of a nice, nice deal that landed in the lap and I was like, I’m just going to take it because I don’t know what else is going to happen next. And I think if I were to a understand my purpose, better be had a little bit more of a plan and had some different options that were really more aligned with what I wanted to do, have a bit of a plan, what I wanted to do next, and then kind of choose an option that would set me up that way. I mean, like I, you know, I left my burnout early, right? Like, I had a three year burnout. I lasted nine months, ten months, maybe.

Dr. Jeremy Weisz: 09:17

Why is that?

Bruce Eckfeldt: 09:18

Well, it was just like once. Once you kind of give up the reins, right? So when it’s your company, it’s your baby, and you’re running, you sell it, and now it’s someone else’s company, and it’s just a job. And I realized that, I mean, I was getting paid well, but it was like, I don’t want this job, right? This is no longer fun. And, you know, you I think this happens pretty typically, right? You take these burnouts because you get a better deal, right? You get better valuation. Right? They say, oh, great. Yeah. You want this much? Fine. Like we’re going to put it in an Earnout and you’re thinking, oh well great. Now this. You forget that you’ve got to earn that money, right? And that’s work that you still have to do. And showing up to work every day. When you own the company is one thing. Showing up to work every day when you’re someone else’s company.

At that point, that whole psychology changes. And I think that is vastly underappreciated, mostly for entrepreneurs. And what that really changes in terms of psychology and motivation. And then of course, it’s someone else’s company, right? They’re going to have decisions. They’re going to have control on certain things. And you know, yeah, you can have the best conversations in the world. Pre-deal about, oh, what the plans are. We’re going to grow, we’re going to do this. Like we’re going to keep the people. We’re going to keep the, you know, culture, all these things. You know, at the end of the day, like post-transaction, all bets are off, right? Like it’s going to be different and it’s not even malicious. I think it’s just situational. Right. Things change.

Dynamics change, markets change. You got to make harder decisions. They’re going to make decisions differently than you are. And so you know I think that whole taking the exit, you know, the terms of the deal end up becoming much more important or much more important than people think, than just the pure number. And it’s hard, you know, you get caught up in the number, you get caught up in the reputation. You know, you’re talking to your friends and all like, what do you sell for? What was your valuation? What was the number, how much you make. Right. Like you get caught up in that psychology and you forget about what does that actually mean to be right? I’ve had funny cases too, where people, you know, agree to non-competes for periods of time.

And, you know, one client I worked with there, he ended up getting in trouble for mentoring because the buying company said, well, no, these, you know, work mentoring other companies, even if it wasn’t directly competitive, was still violating or potentially violating non-compete. And look, we probably, probably could have gone to court, probably would not get ruled against us. But just dealing with it was a nightmare, right. So it’s just, you know, it could take up time, money of actually fighting it. And so he just had to say fine, had to step back and spent three years quiet hiding, you know, until that non-compete was up. them. So these are the things that I just find people don’t think about and end up having a huge amount of impact in terms of really their, their future happiness, but really the effectiveness of the deal.

Dr. Jeremy Weisz: 11:56

I want to talk about general advice and mistakes. Okay. You mentioned a couple, right? Maybe being careful about non-compete. I’ve heard you in other videos talk about being okay with what you get right off the bat, which you kind of mentioned your earnout. What are some other general. Again, we’re talking general rules here. Not every situation may not apply. But you know, from your experience with yourself and many other people, what are some general rules people should consider with the exit and maybe some mistakes too?

Bruce Eckfeldt: 12:30

Yeah. Kind of where to start. I think more conceptual ones and then more practical ones. I think conceptual ones is really be aware of as best you can. And it’s really hard to do this. And that’s why you kind of hire other people and get other people involved in the process. Is your kind of identity attachment to the business? And you don’t realize it till you lose it, but how much you have your own kind of self-worth, your ego, your sense of identity is wrapped up in the business. And being the founder and being the CEO of a business. And. You one of the key things that I end up doing is making sure that we’ve got a broad social, relational network for founders outside the company. Because I always like it happens every time they sell the company. And it’s like no one returns their phone calls, right?

And all these people that were my friends were really just my colleagues in business. And now, you know, they’re either off to other things or they’re still in the business. I’m no longer in it. And I’ve lost all of these social connections because my social world has been entangled with my professional, particularly my company. And so I think one is making sure you’ve developed a robust and well diversified identity outside of the business. And that’s something I would say do sooner rather than later. I think it’s something that you can kind of go. It’s good to kind of keep in mind going into business and early stage companies like, okay, how balanced am I? And, you know, we can talk about family and other things too. But people get very focused on the business. So I think that’s one area that I end up doing a lot of work in, are ends up becoming quite a bit of an issue.

Dr. Jeremy Weisz: 14:17

Do people push back on that, like with you, Bruce? Like that’s not going to be a problem for me. I have a lot of friends who, you know, I have various relationships with. Or is that like, oh yeah, I get that.

Bruce Eckfeldt: 14:32

So, so some of this is probably a filter. Like I end up probably working with people that kind of get that. If you really don’t get that, you’re probably not going to hire me or, or I’m probably not going to want to work with you, you know? So, you know, now, I think there’s still I think they’re aware of it. They probably realize they’re not aware as they probably need to be, and they probably realize that it’s still going to be a challenge, right? Like it’s something that you need to put some positive pressure behind to make happen, you know, even if you’re aware of it. Like you have to do something about it. And that takes time and energy and decisions and you have to make some offsets and stuff.

So, you know, and and it’s you always think it’s not as bad as it’s going to be and ends up being a lot worse than it is, right? Like, I think that’s every facet of this is I think every entrepreneur, every founder goes into this. Oh, oh, yeah, I’ve thought about that. Don’t worry, I’m totally prepared for it. And then get to the other side and they’re like, oh my God, I was not prepared for this. Right? Every interview that I’ve done on the podcast, you know, not 90% of them. So, you know, I think that’s a big kind of general one. I think the, the, the next kind of category, there’s a lot of this kind of personal emotional kind of connection stuff, which is a bucket. The other bucket is I talk about making your business viable. So there’s valuation which we can we can start talking about valuation drivers and things that a buyer is going to look at in terms of like moving that number up or down in terms of what the valuation is or what they’re willing to pay for the business.

But separately from that, I talk about viability, meaning you can actually have really good fundamentals and a highly profitable business that has a lot of future growth that, you know, should be valued at in a certain way, at a certain number. But if the business doesn’t have the information organized, doesn’t have the structures in place, hasn’t documented everything, right, it is not set up to be viable. It’s like it’s putting a veil in front of the business. And so the buyer, even if beyond the veil, it’s this great business, but they can’t see through the veil. If that veil is really thick and cloudy, they’re going to have to devalue. They’re going to have to offset value for.

That risk right. Uncertainty lack of clarity equates to risk for a buyer. And so if I haven’t done those things, if I’ve created a lot of fog around my business and they can’t see it, even if it’s there, if they can’t see it, they’re not going to value it or they’re going to offset it with risk. Making it viable is really important. You know, and that’s you know, like I said, having you know, having, you know, documents together, having all of your, you know. You know, contracts, having all those things in place and, you know, your data repository, data vaults. Right. Having all that stuff together. And if you can show up to the beginning of a transaction or beginning of a conversation with a potential buyer, with having all that stuff clearly laid out, that buyer is going to be much more likely. A is going to probably give you a much better evaluation because actually see the data and the transaction is going to go much more smoothly, which is probably the biggest risk in most of the deals that I see is like the more time that goes on, the more delays, the more hiccups, right?

The less likely deal is going to happen, and the more likely you’re going to get, you know, you’re going to have risk on the business, you’re going to have a downturn, you’re going to lose a client. They’re going to come back and say, well, I know we wanted to offer you 32 million, but now we’re thinking 26, right? Like you’re going to lose money. So having that stuff together, the other thing I tend to do, and this is a little bit of a deal strategy thing, a lot of founders, a lot of sellers will, you know, you certainly want to put your best foot forward, but they try to oversell the business. And what happens is that it’s only, you know, later in the conversation or in due diligence where, you know, some of the things start coming up. It’s like, oh, well, you know, we didn’t realize your concentration was quite this big or. Okay. Yeah. We look like, you know, we’re missing some of these documents or we didn’t see that. You know, three years ago, we had this lawsuit that, you know, was resolved, but.

Right. Maybe there’s some liabilities around it or something, or, you know, there’s going to be things. Every business, every business has skeletons. I’ve written articles on this. My suggestion, my strategy on this stuff is put all the skeletons in the closet up front. Like, literally. I like creating a list of all the reasons you shouldn’t buy my company, right? Put them all on the table up front. And that’s going to do two things. One, it’s going to make it a much more real conversation, right? The buyer is going to be much more aware of the things that they’re buying, but more importantly, it’s going to build trust, right? Because ultimately that is what drives these transactions. If a buyer trusts that the seller is representing themselves and the business appropriately, they’re going to follow through on the deals. If the buyer starts to feel like, okay, when’s the next shoe going to drop, when’s the next, you know, skeleton going to come out of this closet? That’s where they start getting skittish.

And either they, you know, they’ll kill deals or they’ll just keep bringing down valuations to offset that risk. And so some of the best transactions that I’ve seen that I’ve been involved in have had that almost like underselling the buyer in the beginning. And then the buyers just sucking up, they’re like, okay, great. Right. Like, okay, let’s solve I can solve all these things. And once, once they realize there’s no other things they need to worry about, they’ll push forward with the deal. They’ll give you the value. They’ll be very clear with things. Right. So it’s a little bit of reverse psychology or a little bit of a maybe a psychology. Most buyers aren’t used to or most sellers aren’t used to, but I think I think that’s a real game changer in terms of the dynamics of the sale process.

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