Nick Berry: Bespoke Partnerships, Owning a Job, Building to Sell

Full Episode Page: Nick Berry: Bespoke Partnerships, Owning a Job, Building to Sell

Summary: In a unique role-reversal, Interview Connections founder Jessica Rhodes steps in as guest host to interview Nick Berry—entrepreneur, advisor, and founder of Redesigned.Business—about his own business owner’s journey. Nick opens up about building and exiting multiple companies, the difference between creating a scalable asset versus owning a glorified job, and how business design can position your company for long-term success, even if you never plan to sell. He shares how bespoke partnerships shaped his best exits, what green and red flags he looks for in operating partners, and how to build with purpose and structure. If you want to shift from founder chaos to clarity, this episode delivers actionable insight, real-world experience, and those rare “aha” moments.

Takeaways

• Know the difference between exiting well and just getting out
• Avoid building a business that traps you as the operator
• Design your business like it will one day be sold
• Create triggering events to guide equity decisions
• Look for clarity, conviction, and coachability in partners

Links

• Redesigned.Business
• Nick Berry on LinkedIn
• Nick on YouTube
• Nick on Instagram
• Nick Berry Guest Profile

Chapters

00:00 Nick Berry's Business Owner's Journey 
05:40 Defining Successful vs. Unsuccessful Exits
08:33 Navigating Business Exits
11:04 Profit Planning
13:58 Stories of Successful Exits
16:37 The Timing of Selling a Business
19:40 Triggering Events in Business Sales
29:47 Closure in Business Decisions
31:12 Green and Red Flags in Operating Partners
33:03 Commitment and Earnestness
34:45 Run Your Business With an Investor's Mindset
36:16 Qualities of Effective Leaders
37:30 Diagnosing Business Problems
39:56 Implementing Effective Operating Cadences
42:20 Business Valuations
46:39 Coaching and Business

🔗 Redesigned.Business    
If you have a business that's not hitting the next revenue tier like it should... You might have a design problem.  
Your business was originally designed to survive, not scale.  
Now it needs a redesign, to break free of the operational inertia and finally scale.  
So the next revenue tier feels intentional and repeatable, instead of... unreachable.

The Business Owner's Journey podcast is where entrepreneurs, leaders, and innovators to share their personal stories, challenges, leadership, and strategies from their own journeys as business owners.

🟢 Official: NickBerry.info
🟢 tBOJ is hosted by Nick Berry and produced by Nick Berry, Kelly Berry & FCG.
🟢 Series Sponsors: SEOContentSurge, FR, Entrepreneur's Edge

➕ Interested in sponsoring, appearing on tBOJ, or having Nick as a guest on your podcast?

Transcript

Nick Berry (00:00)
It's like you continue to work on this business that is not ever getting over the hump and turning into something more. so really it's just, it's some version of having a job that, you know, if you're, might be a little bit better paying job than you would have had otherwise, or it might be a worse paying job than you would have had otherwise, but it's not really letting you escape from.

Jessica Rhodes (00:06)
Yeah.

Nick Berry (00:23)
from that, the rat race or the day to day. And we just stay with it for so

Nick Berry (00:42)
So this turned into a really interesting episode and I think a really good one. And I may have to do this more often. I had a guest, Jessica Rhodes, who is the founder of Interview Connections. Before we started recording our interview, when she came on as a guest, we were having a conversation about my background and she asked if I'd ever shared it. I hadn't shared much of it.

I don't hide it. just don't talk about it that often. And I should. She says, well, why don't you let me come on and interview you? So she came on and I mean, it's a great idea. So, it's what I needed. She came on to the show. She was the guest host. I think that makes me the guest guest. And she interviewed me about my experience and my background, particularly with like some of the exits that I've had in our companies that I've owned. But we

We covered a lot of things. We covered successful exits. We covered unsuccessful exits. We covered what to look for, green flags and red flags in operators. It was a great experience for me to be on the other side and she was very purposeful with the information that she was trying to elicit because we talked about

there's value in this particular section of my backstory that doesn't get shared enough. But it was also great timing for me because I mean, literally at the same time I'm launching redesigned dot business. And it's about like using my experience and the tools that I built for to build my companies, to help other business owners, break out of some of the traps or avoid some of the traps that, that,

that everybody tends to go through, the getting stuckness. So she helped pull some of that information out of me. I want to thank Jessica Rhodes for, she did a great job. I mean, you can tell she's a very natural, she's probably, don't know how many interviews she's done, but she's very polished, well-spoken. She's fun, like an enjoyable conversation.

And from my experience, because her clients are people who tend to be guests on my show and other shows like it, they do a really good job. So between my experience with Jessica and the secondhand experience in working with her clients, I would say you're in pretty good hands with Interview Connections. If you want to check them out, interviewconnections.com.

and make sure that you check out redesigned.business and let me know what you think of this episode with Jessica Rhodes and I.

Jessica Rhodes (03:04)
I'm Jessica Rhodes, your guest co-host today. And I had the pleasure of being one of Nick's guests on The Business Owner's Journey. And before we started recording our interview together, I asked Nick why he started this podcast. And part of what came out of his answer was his story of being a serial entrepreneur who has sold over a dozen companies. So I boldly invited myself to come back on the show, but...

this time as the interviewer, because I believe we will all receive a lot of value from hearing Nick's story. Now, the business owner's journey that most of us focus on is on operating and growing our business. I know for me as a founder, as an entrepreneur, that's where I spend my time. I'm operating the business, I'm growing the business, that's where my focus is. But rarely do we ever think about the fact that our business is an asset and assets

are something you can sell. Only about 20 % of businesses that go to market actually sell, which means a lot fewer, they don't even go to market, so they never sell. So should you sell your business? Should you think about it? Why or why not? If yes, when, what does an exit look like? Let's find out by hearing Nick's business owner's journey. Welcome to your show, Nick.

Nick Berry (04:25)
Thank you. That's great. That's great. That's why you're here because you would do that and do it so well.

Jessica Rhodes (04:32)
Well, I'm honored to be here as your guest interviewer. One of the reasons as well, in addition to what I just shared, that I wanted to come back on and interview you is that I know that podcasters are always putting the spotlight on their guests. They're interviewing other people. I mean, that's what your show is all about. It's spotlighting business owners' journeys. And when I heard just the little bit that you shared with me about your journey, I'm like, you're

audience really needs to hear from you. for, I think that you're like this, a lot of us, we need the story pulled out of us because it's our story, we lived it. So we're like, you know, do people really want to hear this? What would be valuable? And so that's why I thought it would be really great for me to come on and ask you these questions so your audience could learn more about the guy that's interviewing all the people that they're listening to every week.

Nick Berry (05:21)
Yeah, I'm glad that you did because I know that I'm guilty of maybe downplaying or understating or not stating some of the things that I've done. A lot of it may be best of intentions with it, but regardless, there's value in other people knowing more about the experiences. So it needs to be shared.

Jessica Rhodes (05:29)
Yeah.

Yeah, and I think that as entrepreneurs, once we hit certain levels of success, it's normalized to us. It's normal for us. You've exited so many businesses, both successfully and unsuccessfully, and I'll ask you how you define that, that it's normal for you. Selling and exiting a business is more normal to you than those of us, including myself, who have never done that before.

and don't know what that experience is like. So let's start there. How do you define a successful exit versus an unsuccessful exit?

Nick Berry (06:13)
Yeah, I think that's a really important place to start because it can look so many different ways. I've sold businesses that, I mean, it may sound good to have sold this business, but if I had done that multiple times over, we wouldn't be here, right? Because that particular transaction, it wasn't a good investment. So it's important to be able to discern what's

what the difference in the good ones, the ones that weren't headlines and then the ones that are, that's misleading to describe them as a success. So for me, successful has, I think the general definition for a successful exit would be like you're getting, hitting your return on investment goal or whatever that is. getting your money back plus whatever, on top of that. I, for me, it's.

needs to be a market-based wage if there's an operating role of any type, getting profit from the company over the time that I was involved and then being paid for the equity at the point of transaction. That was how I defined success versus unsuccessful.

In my, the ones that I've, that I've talked about, there are four that I would call that meet the successful exit criteria, but I've had several dozen other businesses in my 21 ish years and, and exited almost all of the rest, other than those four. And that doesn't mean, so they may fail my success.

criteria, but that doesn't mean that it was necessarily a failure. Right? So, some of the ones who don't meet those three success criteria, we still like made our money back on those or made our money back. And in addition to that made some profit. It's just that I feel like there's, it would be very easy to paint a rosy picture.

Jessica Rhodes (07:55)
Mm-hmm.

Nick Berry (08:07)
around a number of exits that's not an accurate representation. But if we, if for me, what I wanted to do is say like this, this is how many times I've done this and done it really well. This is the thing that like I can show you my experience and, and this, this was what we were trying to accomplish. These are the ones that are the opposite end of the spectrum that went very poorly. This is what you'd want to avoid. And then there's everything in between, which is, you know,

Maybe some of them were like better than others. Some of them definitely were better than others. But that's where a lot of entrepreneurs spend their time is kind of like in this gray area between like the absolute winners and the absolute losers. A little bit harder to identify those maybe, but there's still plenty of value there.

Jessica Rhodes (08:51)
So say, I would love for you to dig a little bit deeper there because yeah, you mentioned to me like when we were talking before this episode and kind of preparing for it is that, you you believe that a lot of business owners, most business owners are spending their time in the gap between a successful and an unsuccessful exit. So what do you mean by that? Are you kind of talking about like business owners who are exiting or just like business owners in general are spending their time on things that would

create an unsuccessful exit? Like, can you expand upon that? Because I think we all want to avoid anything unsuccessful.

Nick Berry (09:22)
Yeah.

Right. Yeah.

So if it's in the group that it was definitely failing, you know that. That's made clear probably. What I was saying there was they spend a lot of time focusing on businesses that are going to stay in that maybe a good investment of time, maybe, or money, maybe not, but it's not turning into what they had.

Yeah. I've gone into it aiming for, right? So it's a business that, so here's one that a lot of people are probably familiar with. Starting a business, I'm not going to take any pay or I'm going to take like this below market wage for the first year, let it get off the ground or whatever. Once I hit this certain point, then I'm going to, I'll start paying myself. And then that point never comes. Right. Or maybe being able to pay a, the, your owner a wage, but

Jessica Rhodes (09:54)
Mm-hmm.

Nick Berry (10:19)
never really actually getting anywhere with profit. It's like you continue to work on this business that is not ever getting over the hump and turning into something more. so really it's just, it's some version of having a job that, you know, if you're, might be a little bit better paying job than you would have had otherwise, or it might be a worse paying job than you would have had otherwise, but it's not really letting you escape from.

Jessica Rhodes (10:28)
Yeah.

Nick Berry (10:47)
from that, the rat race or the day to day. And we just stay with it for so long, right? There's the perseverance or the resilience or whatever. And I know that there is information out there now more frequently than there used to be about like, when is it time to just throw in the towel on this thing? So those are the type of scenarios that I'm talking about. Like the easy winners and the easy losers, it's easy to recognize them, but it's the ones that were like, but I just need to get over this.

Jessica Rhodes (10:54)
Yeah.

Mm-hmm.

Right.

Nick Berry (11:14)
If you've been trying to get over that hump for several years, doing the same thing is going to get you the same result.

Jessica Rhodes (11:15)
Mm-hmm.

Yeah. So I mean, one of the first things that came to mind when you were talking about that, like years and years ago, my business partner and I implemented Profit First, which was huge because it allowed us to plan for profit and to have separate bank accounts for what we're going to get paid as owners and what, you know, how much

what percentage of our income is going to payroll and operating expenses and things like that. That was a game changer. I don't know if you use profit first or if there's another recommendation you have for business owners that are kind of like, they feel like they're constantly on the cusp, but they're never having that breakthrough to the point where it's an obvious, it would be an obvious successful exit.

Nick Berry (11:56)
Yes. So I don't use ProfitFirst, but I had come up with basically my own version of that for our companies before ProfitFirst came out. So use ProfitFirst, it's better, it's easier to adopt. Mike actually came and was a keynote at one of our conferences and did a workshop with a lot of our clients. That's a great system. But the magic to it is probably what you experienced where...

Jessica Rhodes (12:16)
Yeah.

Nick Berry (12:20)
If without a system like that, you tendency is going to be to do something like what I described where it's like, Hey, I'll, I'll pay myself less. Like I'm going to take one for the team and I'm going to let this thing, I'm going to build up the cash or whatever. And you're starting to like build this habit of the way that you look at things, the way that you see this. And at that point you're serving the business. And there are times where that's what you need to do. Like that I get that. but if that becomes your only move.

you're in trouble and profit first forces you to like break that paradigm and look at it like, okay, I'm getting paid. And then we're going to figure out how to make this thing work beyond that. Because if I, if I'm not able to get paid at least something that's fair, I shouldn't be here. And I shouldn't like the timeline on this ought to be finite. Like we're only going to do that for so long. So I think it's beautiful in that respect.

Jessica Rhodes (13:11)
Yeah.

I totally agree. I've definitely like, I've been in business for 11 years and I've had my business partner and I have had those periods of feeling like we're working for the business and we're not being compensated appropriately. And it just creates this kind of a toxic relationship with your business. Cause you're like,

this is not an equal value exchange. And so it's so important to have those accounting methods and systems to make sure that it is that equal value exchange that you're working for the business, but the business is also working for you and paying you appropriately. Cause I do think that can be really dangerous for business owners to, you know, to feel like, well, I'll, I'll just get the big payout one day. And so I'll sacrifice now, but then what if that, big payout never comes? So,

On that note, I'd love to dive into some stories. You've had a lot of exits, so we're obviously not gonna get to share every single one, but like, let's start with the best. tell us about your most successful exit. Tell us just the story of that.

Nick Berry (14:11)
well, I don't know. It's like having kids that I'm not going to tell them the one's a favorite, even though one is. so there, there've been a few different versions. So, and I think that there is like, there are cool elements to each one. the most recent was like the company that I had for the longest and actually that I, I ran the others. I was like, we had the portfolio company and,

Jessica Rhodes (14:13)
Right.

Yeah.

Nick Berry (14:38)
that were operators in place. And so it was different in that respect, but a business coaching firm that we put together that had been around for, 2012, just exited that at the beginning of last year. And so that's what kind of led to the business, the podcast, right? It's like, was the thing that had occupied my bandwidth.

on a day-to-day basis for the better part of the last decade. then, you know, we had a transition period after we closed the sale, but, you know, I all of a sudden I had a free time. Like I hadn't had in like well beyond that 10 year, like it's 20 years ago that I had free time like this. I'm like, what now? I got to do a podcast.

Jessica Rhodes (15:26)
Yes. So let's dive into this

story because I think this is perfect because this is what instigated the podcast, this free time post exit. So as a business coaching firm, 2012 is when you started the business.

Nick Berry (15:38)
Um, yes. Uh, that brand. Yes. So we're doing, um, like information products, mastermind programs, things like that prior to that, that was going back to 2007. Then it evolved into, um, fitness revolution, which was the company that, that just exited, which actually it was launched as a franchise and, um, were they the fastest growing personal training franchise in the world for several years. Uh, and then over the course, like.

Jessica Rhodes (15:41)
Mm-hmm.

Mm-hmm. Okay. Okay.

Mm-hmm.

Nick Berry (16:08)
pivoted, turned that into a, got out of the franchise model and wound that turned into a license, which is what it still is, but delivering business coaching and branding.

Jessica Rhodes (16:16)
Mm-hmm.

Okay, got it. And so at what point in the business owner journey did you decide to take it to market? Was that always the plan? Was it just sort of like, this is the next step of this journey? Or was there a moment where you said, let's take it to market?

Nick Berry (16:37)
Yeah. So it actually, it was not as intentional as one should be with something like that. The way this came about is I had a former employee who I had talked about this with a few years prior. Not talked about it seriously. He was somebody that I just said, like, you know, he had asked me one time, Hey, do you think you're ever going to sell it or what's the big picture here? And I was like,

And I don't know somewhere along the line or in the conversation, I just said like, you know, were, if I was going to sell, you're the kind of person that I would want to have it because of these characteristics. And that was really about it. And then he left, had another opportunity, but he and I stayed in contact. And then he came back to me in 2023. I was like, Hey, do you think we could actually have a serious conversation about this? Like, sure, let's do it.

And so that, you know, we picked up the conversation and things fell into place probably better than one should expect as far as like moving step by step. But yeah, was some, former employee, would have been someone that, if I was going to draw this out, then I would have created a plan to like for him to ascend to a role and then eventually.

like become a buyer. So we didn't have that foresight, but we're fortunate for it to work out the way that it did.

Jessica Rhodes (18:06)
Mm-hmm.

Yeah, yeah, that's so interesting. Because one thing about, and I don't know if anyone else experiences this, but for me, I co-own a business that's been around for 11 years. We have a good online presence. We're a real company. And so on a monthly basis, at least one to two times a month, I'm getting an email from some firm that's like, have you ever had it valued? And I just delete them because I'm like, who is this person? Was there any of that for you? When he reached out for that follow-up more serious conversation, was there any

question of just like, he for real? Is this going to be worth it? Do I want to? Because now you got to reveal everything and there's got to be a due diligence process. So what was kind of the, what were the emotions and the feelings that you had when he reached out about that?

Nick Berry (18:54)
So with him, it was pretty easy because as far as him being serious, I knew him well enough to know if he was going to bring it up, he was serious about it. And so that part, there were just a lot of things baked into that level of familiarity that you don't have to worry as much about. There are other things that you need to consider more strongly too in those cases. So there's a factor about that situation that

Jessica Rhodes (18:59)
Mm-hmm.

Nick Berry (19:16)
I think makes it kind of unique. At that time, so I was burnt out or had gone through some stuff for more than a year. was like COVID hit and we were like, mean, we, that group of people, that company and our team performed at our absolute best through the pandemic.

Jessica Rhodes (19:25)
Mm-hmm.

Nick Berry (19:40)
It was like, it's one of the proudest things from my entire career. We had none of our clients closed permanently due to the pandemic. And that's like, there's nobody else in that space that I know of that could say that. And I'm really proud of that. And it's like, we got to this place that I don't remember. I don't think there was like a formal finish line, but somewhere along the way, like 2020,

maybe two, early three, was like there was this finish line and I was like, I think that's it. I'm not real sure. I was just toast.

Jessica Rhodes (20:11)
Mmm, wow.

Did you

feel at that moment that you had just achieved the vision that you had set out? And then was there a lack of vision or it was just kind of burnout?

Nick Berry (20:26)
It was, I just looked up and one day and was kind of like, I've been, you know, my routine didn't change. Everything was the same, but I looked back and I was like, wow, I was really kind of like coasting for the last few weeks or, you know, there was just no, I shouldn't say no. It was like this fog, that was just, I was just kind of going at that point. The, maybe, yeah.

Jessica Rhodes (20:44)
Hmm.

Like autopilot?

Nick Berry (20:51)
And it's so it took me a really long time to figure out what was even going on. Like I'm not totally sure. I mean, it's some form of burnout, um, but it, you know, it wasn't obvious to me. It was just like over this period of time, I just kind of, um, maybe it's lost some momentum or some conviction like the, um, yeah, the, the, the fire was, there was enough there that you.

Jessica Rhodes (20:59)
Yeah.

Mm-hmm.

Yeah.

Nick Berry (21:21)
you you wouldn't realize like it's gone. but it was not the, the, had made me to that point, what had gotten me there. So it wasn't obvious to me at least at first. And that made it hard to feet to realize what that something had happened and then made it hard to figure out what, you know, you don't think that it would have been a reasonable for me to just like stop everything and,

Jessica Rhodes (21:23)
Right.

Right.

Yeah, yeah.

Nick Berry (21:48)
and just wait on this, on something to tell me like, this is what's wrong. I, you know, I had to keep, keep the company going and, you know, until I figured out like something, what is behind this? Why am I like, my, my motivation about 60 % of what it was for 20 plus years. So there was that and toward the end of 23, whenever

Jessica Rhodes (22:03)
Mm-hmm.

Yeah.

Yeah.

Nick Berry (22:18)
Justin, the buyer, came back to me. I'd started to like kind of get my bearings a little bit more and I was getting clearer on kind of what was going on. And so I still didn't know exactly what I was going to do, how I was going to address it. But so there was that going happening at the same time as him bringing this conversation back.

Jessica Rhodes (22:42)
That's really interesting because something that, mean, part of being somebody in the podcasting space and booking podcast interviews, I've listened to a lot of podcasts and I've listened to a lot of subject matter experts. And one thing that I've heard from people who talk about selling a business is that you don't want to try to sell a business when you kind of like hate the business because nobody wants to buy something that you hate, know, energetically. And that makes it tough. And I've seen that, like I've witnessed that over the...

Nick Berry (23:02)
Yeah.

Jessica Rhodes (23:07)
decade plus that I've been in business and have seen many entrepreneurs grow and decline and sell and all of the things, I've noticed the ones that waited till they were really burnt out to sell, it just, could, it's like, was, were going down the other side of the mountain versus being at the peak and, you know, kind of being at that summit. So can you talk a little bit about that, both from maybe this experience and from your other exits, the timing, like, let's talk about the timing of how people know.

Nick Berry (23:23)
Mm-hmm.

Jessica Rhodes (23:34)
Right? For you, was just like, I was at 60 % moment, like motivation and yeah, talk a little bit about that.

Nick Berry (23:39)
So I think as far as going over the peak and then it being kind of downhill, I wasn't on the downhill, but I was getting over there. So I think my thought process when the opportunity to sell came up and I was still like, what's going on here? I'm not exactly sure if this business

Jessica Rhodes (23:49)
Hmm.

Nick Berry (24:06)
Is the cause of this or not? don't feel like the business is the problem, but I'm just going to do something different. I'm just to that place where I'm okay with closing this chapter. I'm happy about it. It'll be, it's a good opportunity. that giving myself that kind of separation, I think is going to be what I need to get clear my head the rest of the way and figure out like.

what direction to go next. So I don't think I'd gotten to the place where I was like resentful toward the business, but I can totally see it happening. Yeah, that's, I would say that's would be what probably would have happened had I gone long.

Jessica Rhodes (24:31)
Mm-hmm.

Mm-hmm.

Right. Yeah.

Nick Berry (24:47)
So

in my, the other instances haven't been anything like that, but they were, they were more planned. So let's see, two of the businesses. So when we go back to 2007 and I'd mentioned getting started and doing the information products, masterminds, we.

Jessica Rhodes (24:53)
Okay.

Nick Berry (25:12)
So I had a business partner then and we had kind of established ourselves as like the business guys in that space. And so we had a lot of creators at that time, but they weren't called creators. That wasn't a thing then. But we would have clients who would come to us and say, hey, like I've got this idea. I think I can do this thing. I have this business idea and, but I need, so I don't know anything about business. I just know how to do this thing really, really well.

And so, you know, that happened and we partner with somebody and then it happened again and we partnered with somebody. And so basically we would like, you know, go with a creator or a subject matter expert and like handle the business part of it. They could make their magic and everybody won. And before you know it, we had, I think at most a eight operating brands at one time had our management organization running that. And

So after a few of these partnerships, that wasn't an intentional strategy to begin with. But once we had people who were very good at what they did, who already were established coming to us saying like, hey, I've got this thing and I can crank it out and I can get a lot of attention for it, but I need somebody to build the machine that lets me just do that. That's what I'm good at.

Jessica Rhodes (26:28)
Yeah.

Mm-hmm.

Nick Berry (26:32)
So then I realized like, okay, this is a strategy. This is our thing. So from there, these partnerships, we would be more intentional about saying like, look, this is probably going to be how far this goes. Right? So we had the two that I mentioned were slightly different criteria, but in essence, they would come and say like, look, I want to do this thing. I can do this really well. I'm willing to give up.

Jessica Rhodes (26:47)
Okay.

Nick Berry (26:59)
X for it, but I needed to be kind of like this, right? So one of them was like, hey, I can only operate this part-time. So, and to me that's usually a red flag. Like I don't want to do hobbies here, but he was a very serious person and serious like earnest, committed and convinced me of that.

Jessica Rhodes (27:04)
Mm-hmm.

time.

Yeah.

Right.

Nick Berry (27:20)
And demonstrated to me like, look, I can do this in just a few hours a week and here's the value we can create. And so, okay. So we did that and out of a part-time, a part-time investment on his part within a few years, I mean, he had a multi six figure exit, like for his part of it. So like, you know, that's not bad for being able to scale something on your own terms like that. Another was a.

Jessica Rhodes (27:37)
Yeah.

Yeah.

Nick Berry (27:46)
a creator who we, so he, were doing, we were involved in the manufacturing, warehousing, shipping of a retail product. And it's kind of similar like husband, wife, family. And he's like, I've got this stuff. can sell a shit load of it. but I needed to like, no longer be a burden on my family.

Jessica Rhodes (28:03)
Hehehehehe

Nick Berry (28:10)
So we got to figure out how to replace the workload that my spouse is taking on. I mean, and that's totally reasonable, right? But it's like, man, how do you know they're immersed in this? How do you dig them out? But that was our thing. It's like, okay, part of the architecture here has to be, we got to extract him, make sure he can still do all of his things, make sure that the business can.

Jessica Rhodes (28:20)
Mm-hmm.

Nick Berry (28:37)
can grow, continue to grow and produce the way that it has, but we've got to basically like, you know, give it artificial arms and legs or, you know, replace the real ones with artificial. so, but being, so those nuances, guess, or criteria were things that we were able to use as kind of milestones. So from the very beginning, we could plan for when we hit these, then it can be a triggering event.

Jessica Rhodes (28:45)
Mm-hmm.

Mm-hmm.

Nick Berry (29:04)
And in some cases, those are triggering events for equity transfers or other types of compensation. Sometimes it was a trigger for now we have the option to buy or sell. So we could buy them, they could buy us out one or the other, or we could stay the same. But someone has the option to make a choice at a time. So those I would describe as like predetermined.

Jessica Rhodes (29:19)
Yeah.

That's so interesting. So you've sold companies, you've acquired companies, you've invested in companies. I love the range. Tell us more about the triggering events. Are those predetermined as business owners or is that like a terminology that's kind of well known in mergers and acquisitions? Like what is a triggering event?

Nick Berry (29:47)
Yeah, that's well known. That's a thing. We didn't come up with that. It's just establishing like, we're going to do this. It's putting something on it that's going to give an opportunity for closure. So it's not going to go indefinitely.

Jessica Rhodes (29:50)
Mm-hmm.

OK,

so it's that way as multiple business owners, equity shareholders. It's not like somebody feels like selling. It's like, no, we all agree that when the business hits this bunch profit or this happens, then we're going to have a conversation about what to do next. Is that kind of what you're saying? OK.

Nick Berry (30:15)
And that's exactly what I'm saying. And

one person has a choice that's going to matter. Right? So we might all get to vote. It just depends on how it's structured. But ultimately, the buck's going to stop somewhere because it's not going to, we're not going to sit here and thumb wrestle over it. And avoiding that I feel like conversation is the thing. Do you want to have those, the I feel like conversations?

Jessica Rhodes (30:20)
Hmm.

Yeah.

Mm-hmm. Right.

Yeah.

Nick Berry (30:42)
along the way to keep your finger on the pulse. You don't want those, I feel like conversations to be your decision conversations.

Jessica Rhodes (30:45)
Yeah.

Right, right. As somebody who invests and has invested in companies and invest in it, especially founders who are just really good at their thing, but maybe not necessarily operating the businesses, what are, let's talk about red flags and green flags. Like what are the green flags? Things that are like check, check, check. That's a great opportunity. And what are the red flags where you're like, maybe it'll work, but like that's a reason to dig a little deeper.

Nick Berry (31:12)
Yeah. In the founders themselves.

Jessica Rhodes (31:17)
Yeah, like when you were as somebody who would invest in a percentage of equity of somebody's company, like these examples that you were just sharing, whether you're acquiring the whole business or acquiring a percentage of it, like what are those green and red flags?

Nick Berry (31:26)
Mm-hmm.

Yeah.

Yeah. So what I would look for out of somebody right now is they have to have some idea with some conviction. And there needs to be some evidence of that. prefer traction, like some proof that they've been able to get some momentum, make some sales, but they have to be able to speak about that thing pretty clearly and articulate like where the boundaries are.

Jessica Rhodes (31:37)
Mm.

What do you mean

by boundaries?

Nick Berry (31:58)
they can define their lane really well. Like what is it about this thing? What's that?

Jessica Rhodes (31:59)
Okay, like their role in the company?

Like their role in the company or in the market? Okay, got it.

Nick Berry (32:05)
Both. Yeah. If we're

going to go, if we're investing in the business, then it's going to need to be both. But typically that person is going to be able to speak really well about the thing, the problem that it solves in the market. And it's, and they'll be able to say, you know, it's like this except for, or it's like that, not with the, so they know what the edge is. Another thing I mentioned this already is the earnestness. And that is like,

Jessica Rhodes (32:10)
Mm-hmm.

Hmm. Okay, got it.

Mm-hmm.

Nick Berry (32:33)
become so much more apparent to me in the last four or five years. you know, um, solopreneurs in particular are, you know, teach their own, right? Like not everybody, everything has to be, you don't have to, um, live and die by it. Maybe the way that, that I would, or that somebody else would, you can, you can run a business and treat it like what I would call a hobby and it do well. it doesn't, however, you want to define that that's okay. What I'm looking for would be.

someone who is committed to the degree, like they're going to do what it takes. And they know that that's going to change over time and it may change day to day some, and sometimes it's going to be really hard and sometimes going to suck, but they're committed to it and it's going to take what it's going to take. And they're not going to show up with the sense of entitlement, over, you know, because they are the business owner or because they read an article about.

Jessica Rhodes (33:08)
Mm-hmm.

Yeah.

Nick Berry (33:29)
you shouldn't have to grind like there's no problem. Hey, I'm not trying to get like grind anybody down either. Right. I don't think that has to be the way, but sometimes you, may have to go into that mode, but that's go ahead. Sorry.

Jessica Rhodes (33:36)
Yeah.

Yeah,

no, that's okay. This is great. Something that my mentor has, I've heard her say a lot, her name is Melanie Ann Leir. She always says, you know, basically it might be hard, it might be easy, either way I'm in. And that mentality has been really, really great because as a founder, an entrepreneur, a business owner, right, sometimes when it's really hard, you're just like, wait, this shouldn't be this hard. I'm the business owner. But you know what? Sometimes it's hard, sometimes it's easy. Either way, like how committed are you to the goal?

Nick Berry (33:55)
That's her.

Jessica Rhodes (34:10)
And I just want like, I want you to keep going, but I want to interject because I like to just really make sure the listeners are looking at this. Whether you plan to sell your business or bring in an investor or not, you will run a better company if you are taking these lessons to heart. Because when somebody like an investor is outside looking in on your business, they're just looking at it as a business. Like I've got this book right here called Run It Like You'll Sell It. Like there's just so much gold in looking at.

what does an investor look for? Because when you can run it like somebody wants to buy it, you'll just run a better business. Like learning about this stuff has made our business so much better.

Nick Berry (34:42)
Exactly.

Right. So I really like what you just said there about if you, one of the ways, one of the things that you can do to, to be a better thinker, a better leader for your business is an exercise, just thinking about what, how someone else on the outside who knows what these things need to look like, sees your business. And if you can't put yourself in their shoes entirely, think about when you're going to pick a stock, you're going to pick a stock from

a set of acronyms and they're going to have some either green or red numbers beside them. And that's all you know about. But, but that's like, that's enough for a lot of people for, well, with some context, like that's all they, that person, that outside expert is going to see your business as. Right. So, you know, I'm not going to say they don't care about more than that. They, they, they may very well, but there are.

Jessica Rhodes (35:15)
Mm-hmm.

Nick Berry (35:41)
measures, are indicators that matter and you need to make sure that you know what they are and you need to make sure that they are showing up.

Jessica Rhodes (35:49)
Yes, absolutely. And also what you were saying before about conviction and being able to clearly define your role, both in the company and in the marketplace, that's going to make you better at sales. That's why podcasting is great because the more you talk about what you do and the value you bring and the problem that you solve and how you're different, you're just going to be so much better at selling your product or service. So I think that this is all good. So let's keep it going. What other, what else do you look for?

Nick Berry (36:16)
So, earnestness, clarity on the problem that they're solving. And then I think the next thing would be as a leader, like the way that they think about things. their critical thinking, communication, are they somebody who leans into feedback or are they somebody who shows up with all the answers? Because like that's,

That is a leadership style, I think. And it works in some instances, but you don't need me if you don't have all the answers. what I do is help design the business, the machine, but also like coach the leader through their evolution so that I'm looking for somebody who is coachable, who's leaning into those things and trying to become a better thinker also. And I feel like.

Jessica Rhodes (36:59)
Right, right.

Nick Berry (37:02)
Those criteria shouldn't, they're not exclusive to me for sure. But I feel like those are almost universal criteria for someone who's going to do well growing a company.

Jessica Rhodes (37:05)
Mm-hmm.

Yeah.

What are some aspects of a business that you as an investor, like if they're not going well, the things that you're like, I could fix that, you know, cause maybe not everything in the business is like perfect, but like, what are the problems that you feel like are easy for you to solve if a founder is not solving them?

Nick Berry (37:30)
Well, think that there, the, what I just was describing as like the architecture of the business. there are some things that I feel like we business owners take for granted. So I was just having a conversation this morning about like an operating cadence. And, so to me, that means like,

Jessica Rhodes (37:36)
Mm-hmm.

Nick Berry (37:50)
getting everybody kind of in this cadence, everybody in the business, in this cadence of like, we operate on these like yearly, quarterly, monthly, weekly cycles. Right. And so everybody's always thinking if we're having a conversation and like, okay, you're going to get me this thing. And without saying it, we both recognize like, it's kind of assumed that that's either going to be within one week.

Jessica Rhodes (38:02)
Yeah.

Mm-hmm.

Nick Berry (38:17)
Or

it's going to go to our next big meeting, whatever that is. But that's us being in lockstep with our operating cadence. And I think that is so valuable for a company to keep them pushing toward their future and they underestimate it. So, I mean, it's really like, you don't hear people talk about it. So they're doing without it.

Jessica Rhodes (38:34)
Mm-hmm.

Nick Berry (38:43)
So that's the kind of thing, like if you let me watch, let me follow you around for a day or two. And I can probably tell you where you've got things that are going on that are chaotic around you and you're used to it. That could all be like a headwind.

Jessica Rhodes (38:58)
Yeah, yeah, there's a lot

of different operating systems. I know there's EOS. We use Scrum and Agility. it's the same thing. There's learning cycles. So there's daily stand-up meetings. And then there's monthly retrospectives, where we're purposely looking back at the previous month.

Nick Berry (39:13)
Ahem.

Jessica Rhodes (39:16)
And then we also use an experiment tracker. So if we're gonna try something different, we put it on a spreadsheet, we track it, we say, what's the criteria for stopping this experiment? What's the criteria for changing? And so we did that, we were experimenting with a certain type of bonus to incentivize pay-in-fulls. And so we tried it and our pay-in-fulls went down. And I said, we are stopping this experiment, it is not working, let's move on from this. In the past, before we learned about this,

We would just make a change because we thought it was a great idea and years would go by. And then we have no idea what changes would cause, were causing the results, either positive or negative. So I think that's so important is to have those systems in place. Yeah.

Nick Berry (39:53)
you

Yeah, I like that. think,

as you're talking about that, another thing that comes to mind that, that works really well, like, I think it's easy for me to recognize if they don't have a strategy in place and, or, so I think I'm really good at diagnosing, like I can smell smoke. And so if I know if I smell smoke, I just need to like follow it and I'll figure out what the problem is.

Jessica Rhodes (40:07)
Yeah.

Nick Berry (40:20)
a new client just a few weeks ago, but I was having a conversation with her and it's like, there was something, she seemed really clear on who she was going after and she's super clear on what she does. but there was something like, I don't remember exactly. I wish I had it. There just a couple of words that jumped out in this conversation that like, there's something like the sense making going on here was, was I was firing and.

so I dug in and really all she was doing was she had like co-mingled to multiple audiences and, and her offer, she'd kind of like expanded. had a little scope creep to, try to account for that. And like, she's in it every day. you know, it's, she didn't realize it. It had just had kind of evolved, but I was able to, to pick that out, just by smelling the smoke. And so.

Jessica Rhodes (40:57)
Mm.

Mm-hmm.

Nick Berry (41:11)
To me, that's a strategy thing, being able to sense you've kind of balled up multiple offers and markets here and you're botching your strategy and doing that, right? So being able to help her disentangle those things.

Jessica Rhodes (41:23)
Yeah.

Yeah, I think a lot of entrepreneurs are visionaries and a lot of visionaries get a feeling for a good idea and then they just run with it without like staying the course of the previous idea because some things take a long time to refine. And I don't know if you agree with that, but it's like people want to like jump and do something different. And it's like, well, wait a second, like with the scope just kind of creeping out and emerging audiences, it's probably like the littlest thing, but you saw that just you smell the smoke.

Nick Berry (41:44)
Yeah.

Right. So I think you're exactly right about what they do. And that's a good thing. So the way that you counter that is you need to have, like that's her strength is being that way. I don't want her to be different. The way that she counters that is she needs to make sure that she's got other pieces around her that will catch it when something starts to smoke. Or if she's like really out of bounds, who kind of like, Hey, you know, this is, this totally misaligns. Like we don't even need to start doing this.

Jessica Rhodes (41:57)
Mm-hmm.

Right. Yeah. Right.

Yeah.

Yes.

Nick Berry (42:20)
So, you

know, that if that's a strength for a visionary like that, let's let it be a strength. Let's fan the flames, but let's also put some things into place. We can wear a safety harness, right? So yeah, let them, let it be their strength and let's ride it and not hold them back. That doesn't mean they're going to be right about everything. We're going to put some safety measures in place and collectively the whole should be greater than some of the parts.

Jessica Rhodes (42:27)
Yeah.

Mm-hmm.

Mm-hmm.

Yeah. What are your thoughts on business valuations? Should a bit like should like I'll leave that open ended, but have you like do you get your businesses valued? Like just talk a little bit about that.

Nick Berry (43:02)
so my thoughts are generally it's not worth, you don't really need one until you need one. I wouldn't, I don't, I've never bothered, other than as a part of a sale. And, you know, I think this is another conversation I was just having also, like getting a valuation done. I don't like who, the person who's going to do the valuation is just.

Jessica Rhodes (43:08)
Yeah.

Mm-hmm.

Nick Berry (43:27)
probably if it's, if they're unbiased, it's going to be a CPA or somebody like that. And they're, they're just going to math it up and not, they're not probably giving you what you're actually looking for. Or if it's a broker, they're, you know, they're trying, trying to sell a business. but they're, don't know of really better, resources, you know, it's going to be situational, as to what you should do.

Jessica Rhodes (43:35)
Right.

Mm-hmm.

Right.

Mm-hmm.

Nick Berry (43:53)
But most situations you don't need one. And for ours, so what I did was we used the same formula for the valuation every time. We had it done the first time and it applied for every exit. Thankfully, because that's just, you know, when we were talking earlier about making things, trying to like extract the feeling part of it and make it as...

Jessica Rhodes (43:55)
Yeah.

Okay.

Nick Berry (44:19)
as fixed or like rigorous, I guess, as possible. The formula for evaluation is a thing that could be really contingent under if you're sitting on opposite sides of the table. We were able to avoid that because we had one, it was been used, there was no reason for anybody to question it. That's not always the case for.

Jessica Rhodes (44:32)
Mm-hmm.

Yeah.

Nick Berry (44:45)
for people who are trying to exit, but that's where there are much more sophisticated succession planning and exiting strategies or processes than what we did, what I've done. If your business is, you're building it for your retirement, which you should be building it with the exit in mind, because it's going to make you run a better business, which is what you've said.

Jessica Rhodes (44:57)
Yeah.

Mm-hmm. Yeah. Mm-hmm.

Nick Berry (45:09)
Also, like that's just, that's the prudent thing to do. Like you're building this asset. So you probably have done that with your retirement account. Like you have a plan in mind for that somewhere down the road. So you need to do your, your business the same way. And if it changes, that's fine. But planning with that end in mind and then like reverse engineering from there. And that's where you can account for, at what point do we need to be getting it valued in order to get it to a market?

to find a buyer in a reasonable timeframe. What are the things we need to do before that? Like what are the markers that will go into the valuation that we need to make sure we have like really emphasized? And that's what I would tell anybody who, if you're not under the gun, if you're not trying to get out, or if it's not just like this kind of.

Jessica Rhodes (45:47)
Yeah.

Nick Berry (45:54)
opportunity that came up like it did with me, you need to find someone who does succession and exit planning and, talk to them about it because they can tailor some of this stuff a little bit more to your situation and say, okay, this is how someone in your shoes typically needs to do this. This is what you need to consider.

Jessica Rhodes (46:02)
Mm-hmm.

Mm-hmm.

Yeah, wow. There's so much value in this episode. You have shared so many amazing pieces of advice and wisdom. So how can your listeners work with you? If they're like, I want Nick to actually look at my business and coach me through everything that you're talking about, how can your listeners work with you? You mentioned you have a client, so I take it people can hire you to coach with you or tell us about that.

Nick Berry (46:40)
Yeah. So, since the, since I exited, and, and just, I was just doing the podcast and then I had a few people get in touch with me that I knew. I, so I've done some strategy work with them, but it's been about a year and I've just recently decided I'm, going to actually start doing this thing again, and I'm going to do business design. So it's kind of bringing the architecture angle to it a little bit more. It's kind of.

Jessica Rhodes (47:03)
Yeah.

Nick Berry (47:06)
I think there's this sweet spot between this like lifestyle hobby concept and the, like a templated, you know, more traditional business there. There's room to operate, for those subject matter experts or even entrepreneurs like the ones I'd mentioned

I'll be doing business design and coaching. If you want to get in touch with me about it, my website,

Redesigned.Business,

but I'm happy to talk about that stuff and, help. So one thing that I think maybe I'm a little unique,

If I can't help you, I'm not gonna try to convince you to do something you shouldn't. What I wanna do is understand your situation. And if I need to advise you in a way that steers you in a different direction, that's cool with me. I'm really big on understanding what you're trying to accomplish. And I don't mind telling you what I think is in your best interest, even if that doesn't involve me. So.

Jessica Rhodes (47:40)
Yeah.

Nick Berry (48:00)
If you're interested and want to have a conversation, like I should be pretty easy to handle.

Jessica Rhodes (48:04)
I love that. I'm the same way in my business. It's all about, that's why I call my calls consultation calls because it's really just to see if it's a good fit. And I think that anyone listening to your podcast, anyone listening to this episode that's having some light bulbs go off and thinking like, what is the architecture of my business? Or, you might want to sell one day or bring in an investor or just have a plan. Have a plan for whether it's five years down the road, 10, 15, 20, like one day you're gonna want to retire.

Like you will, I know every entrepreneur is like, I will never stop working. like maybe you'll like my dad just retired. He still coaches like five clients. You know, he just has like a few days a week. He's still coaching, but he did retire and he did sell off one of his businesses and that succession planning is so, so important. So I highly encourage everyone in your audience to reach out to you to see if it would be a good fit because you clearly have so much experience, so much knowledge and expertise around what investors are looking for. What are the green flags, the red flags?

how to plan all the different scenarios. think it's awesome. So thank you for having me on to your podcast to interview you all about your story.

Nick Berry (49:08)
Thank you. You

did a great job. I really do appreciate you handling doing this with me and maybe pulling some things out of me that I've not done a good job of getting them out and sharing them in the past. So thank you. This is what I needed.

Jessica Rhodes (49:10)
Thank you.

Well,

and I think that's again, why your listeners should reach out to see if you can help them because I think the fact that you Nick aren't as like, look at me, you know, like I think it took me coming on and like pulling it out of you. You are such an expert and you have such great experience and it's not all smoke and mirrors and great marketing. It's like, no, you actually have so much business ownership and operating experience and investing and exiting that, that if people need your support, they should reach out.

Nick Berry (49:52)
Yeah, because I'm happy to share it. Like I'm happy to give that advice. Sometimes I just have to be forced to tell people that I have it. but thank you. We've made a great team. like this. think there's something here.

Jessica Rhodes (49:53)
Thank you for.

Yeah. And I'm happy to be that person.

Yeah, I love

it. Well, thank you for having me on. If anyone wants to check me out, my business is interviewconnections.com. And so you can come say hello to me, but reach out to Nick for sure.

Nick Berry (50:16)
Absolutely,

thank you.