Welcome to the debut episode of If They Knew What I Know, where we dive deep into the untold stories and invaluable lessons of experienced business leaders. In this episode, Matt sits down with fellow entrepreneur Erin Gregor to unravel the transformative journey from building his first business with his father, to navigating failures, and finally creating a thriving second venture focused on leadership, knowledge transfer, and business continuity. Listeners will hear firsthand how personal challenges—including a health scare during the pandemic—sparked the insight that true business resilience comes from capturing the unique, often undocumented knowledge held by leaders.

They discuss why traditional SOPs and systems fall short, and how his innovative approach—what Matt calls "the genius handoff"—helps owners prepare their organizations for succession, sale, or simply stepping back, all without missing a beat. They also talk about practical examples, hard-won lessons, and the realities and misconceptions of entrepreneurship, leadership succession, and building businesses that endure. Be sure to subscribe on your favorite podcast player for new episodes!

And to learn more about COtingency, visit: www.COtingency.com

Key Topics Discussed:

Top Six Topics Discussed

• The Inspiration and Lessons from Past Businesses:
• The Critical Shift from Growth to Exit Planning:
• What Typical SOPs Miss in Succession and Knowledge Transfer:
• Misconceptions Business Owners Hold About Replacements and Documentation:
• How Leaders and Buyers Use Structured Knowledge Extraction:
• The Importance of Timing, Scale, and Proactive Preparation:

Welcome to the very first episode of if they Knew what I Know. We're going to take a little bit of a different twist. Matt, welcome to your podcast.

Thank you. It is wonderful to be here.

Well, very excited to have you here. And what we want to do today is obviously introduce the podcast, but get our listeners to know just a little bit about you, about your story about why Coach agency and why this is so important for them to consider and know and understand. So in order to do that, let's go a little bit back into your history and talk about your business. And you started to build a second business. You had some history, and I'll let you tell as much as you want to have that story, but you did all the things right. So can you talk about what you saw in your first business that you really wanted to parlay and, and do right in your second business as you were building it to make sure you weren't a point of failure within that business?

Sure. And by first business, you mean the, the one that I founded with my father.

Yes. Yeah. So just, yeah, just talk a little bit about, like what, what inspired you to do things differently as you built your second business?

Sure. I didn't immediately start building the second business that right way at all. In fact, I started building that second business out of survival mode because the first one didn't work out. And I was a natural born entrepreneur. And I thought to myself, okay, if this first one didn't work, I'm going to tweak some things, but I'm going to rely more on myself and not necessarily someone else. And, and once I started healing from the loss of the first business is when I realized, okay, I gotta find, like, my tribe of people that can help me achieve and learn a lot of things about personal and professional development. And on that journey, it taught me all about scaling, about business growth and building something bigger than yourself, but it didn't actually teach you about selling your business. So that whole idea of, you know, making this thing much bigger than me was really just attributed to growth and not necessarily about the actual eventual exit.

That whole idea of exiting my business came about around the same time as the idea for building contingency. Funny enough.

Okay, so I really want to keep honing on this just because this is where business owners just struggle. So let's talk about that first shift that you're going, you're building. And you said, I wasn't thinking about the sale, I wasn't thinking about long term. So what changed in your business from that point where you said I have to make these specific changes to really get it to that next level, that I could walk away, that I'm not a point of failure.

Yeah. So you would think that me seeing a bunch of multimillionaire business owners dropping debt from COVID or getting horrific comorbidities and diagnoses with it that were just sending them into like months long stays with their businesses crippling would wake me up because that's what my, my law firm was handling for people. Right. As a, a full service estate law firm, we were everybody's first and last call and our clients were business owners. But that wasn't actually what did it. What did it was my own getting Covid feeling like an elephant was sitting on my chest and I couldn't get into the hospital. And at the time I didn't have any kids and my business was my baby. And all I kept thinking about was growth, growth, growth and scaling.

And that's what we were doing. We were hiring a new person, you know, every, every couple of weeks it felt like. And I'm sitting there in what I thought was going to be kind of like that deathbed moment. And I decided to stay up throughout the, writing out everything that I would do for the amazing people that I had around me so that the business could survive me. Because what I realized that night was I've got kick ass people working for me, I've got capable successors, but they don't know what I know about the business, about things inside the business, outside the business. And they don't know my sense of judgment because they've never been an entrepreneur or a CEO or an owner of a business before. They were excellent at everything that I needed to keep the business running, but not to see it thriving. And so that's when I decided to start the process of building something that could take what I knew about my business to make it successful for those that were going to be in my shoes after me.

And I did that that night. I stayed up all night and started writing out the foundational plan for what I thought was going to be a service within my law firm. And it turned into cotangency.

So what changed after those you wrote out those questions and you know, before you actually sold the business, what were some of the biggest changes you saw within your business after you were able to download a lot of that information from your head and, and make that shift?

I, I realized that there was a lot of things that weren't documented that would never show up in normal SOPs that would never show up in normal policies and systems that really organized organizations were documenting. And I realized that there needed to not just be documentation, but a way to hand that off to people so they could be successful. And at that moment in time, when I started writing out everything that had to happen, it was conceptual and it was more outcome driven. It wasn't how we get there. And the how we get there ended up being one of the most valuable parts in what we've built at Cotingency because we work with such a unique clientele in multimillion dollar brilliant, distracted, busy leaders.

I love it. So what do you think is one of the biggest misconceptions you see business owners have about their business and, and being able to get to this sort of level?

I think some of the biggest misconceptions are that they're too busy to prepare those around them to take over for them. That it'll just happen when it needs to happen and people will figure it out. And I, I think that there's also this huge misperception that there is someone out there who is going to be your replacement and is going to be just like you. And that's just not real. Sometimes it's one person, sometimes it's three people. But they're going to bring their own uniqueness. What's important is that they receive on the way out everything that you have to offer.

So when a lot of people hear about what you do hear about the process of a contingency, a lot of times they're going to go to standard operating procedures. Maybe they had a consultant come in and help them with that, or a fractional coo. Can you talk specifically about why you're different and how your process is not the same as an SOP documentation?

Yeah, that's a great question. So there is an incredible place in this world for fractional COO work or documenting policy systems procedures throughout an entire organization. It has to be done, has to be done in order to scale and it has to be done in order to make your business marketable and to sell it and to exit. Right. We all know that across all industries. But what's different is that there is a huge failure that's recurring across almost all businesses. We see for effective documentation of both what leaders know about their organizations from the top down and what their judgment is when viewing from that vantage point with the knowledge that they have. So not only is it not captured by traditional SOP work, but there isn't a mechanism to do so out there.

And so that's where we come in, we extract everything that they know about their business and their judgment, map it out in a way that is almost like a guide. If you were to be handed the keys to the brain of this leader, how would we run this operating system around us? We still need to know everybody's SOPs and how they're going to do their jobs and, and how the systems work. But we want to know how to operate as the leader. And so that's the place that we start from.

So can we give an example? Because I want to know how this, how you see a leader, what they see with this information, and then how it's used within an organization to really transform it.

Maybe it would just be easier if I started having a conversation with you about this.

Okay.

If you were to go up to a leader of a $50 million organization and say to them, I've got plenty of time on my hands, tell me everything you know about your business, what do you think you would get from them?

Very limited. I mean, they may talk for maybe an hour, maybe about their business, but I, they still would be very, very, very high level.

Sure, it would be very high level. They might go down some rabbit holes, right. And, and tell some stories that are really specific about certain instances of things. So you might get some decent examples, you might have some follow up questions. Right. Some clarifying questions. But you may cap out at two or three hours, right?

Oh, yeah.

And then what's going to happen

then you got to try to figure out, to go back and figure out where you left off. If there's anything left off, like it's, the information may get used, but it's, it's not holistic at all. Okay.

What do you wish you would have known if you could have gotten it out of them? What would you have been looking for

from a leader's perspective? All those things that pop up in the moment that they just know what to do, but they, it's so secondhand nature to them that they don't even think twice that it's something else to consider or communicate or knowledge transfer.

Okay, so you're talking about their ability to just fire on all cylinders in reactive leadership scenarios.

Yeah.

Okay, what about some of their unique abilities, if they're a great forward thinker in looking ahead a week, a month, a year, and the way in which they plan. Right. What tools do they use, what people are involved, who gets called into which rooms? Right. So then, so we cover everything from proactive to reactive to their judgment to their people, to what systems Are used to what decisions have been made, to not move forward with different things in their business because they would have been a dead end or a bad end or unique things that they know about competition or about people. They may be recruited that never ended up joining the organization, but be a great target later. You name it, we've probably thought of it and figured out ways to get it out of them and get it out of them fast. And so there was an art to getting the answer. Tell me everything you know about your business out of somebody fairly quickly and thoroughly and then tell me how you would think about things.

Right. Tell me your substituted judgment.

So I'm curious when somebody like, let's say you get that forward thinking like you were talking about, like how do they look to the future? How do they. All these things. So now we have that understanding of we've got some industry knowledge that they've had for, you know, 20 years. So we've gotten that out of their head. Right. Like all these things that help compute that. How do you see business owners then apply it to their business? Let's say if they're getting ready for a sale or they're getting ready just for a leadership transition, like maybe they're going to step away just a little bit or whatever that is. How do they take that information that you've been able to gather and apply it to that next person and be able to see that change within their business?

Okay.

Or set someone else up for success is maybe a better question.

Right, right, right. So what's interesting is that we have clients both on the buy side and the sell side, using the genius handoff. Right. Using our executive cloning process on the buy side. It's very important for buyers who are about to expand their business by the acquisition of another to understand themselves as a leader. Everything they know about their organization and where all the holes exist. And because once you dump another organization under the umbrella of this new organization, it's only going to exacerbate the holes. So that's where we see a big use case on the buy side.

On the sell side, they get an outsider's perspective of what it would take to run this business. All of the holes that exist from their perspective, when they're being honest from their team's perspective. And if they come to us soon enough, they get a blueprint on how to fix everything timely. And if it's not, at least there's a very clear understanding of what's going on in this business so that the parties can transact and do it efficiently.

So important just because when you're buying a business, there's just things you don't know that you don't know. Right. You don't know what to ask.

Just due diligence just does not cover so much of what matters behind the scenes. There's a lot of legal paperwork, exchange, financial reporting, but there's not really taking a car, you know, around the track and test driving it and seeing who's involved on everything, you know, on every corner.

Yeah, ignorance is not bliss when it comes to business transactions. Do you have any great examples of customers that you've seen this work really well with?

Yes. So we had one client who was a potential buyer of a business of an older gentleman. And this is a typical paradigm we see, right. We see a lot of Gen Xers buying boomer businesses or having opportunities to buy boomer businesses right now across the board. And so we saw one where he was going to get a great deal and this, this guy also served as a mentor to him. So they had a close relationship and he was coming to us trying to figure out whether he should be cloning this the seller and learning everything about the business. But we first did it to him with, with his business to see how ready they were to start taking on their business. And it exposed so much that he decided not to move forward with the acquisition of this other business.

He decided to shore up home base before, you know, waging war on another front. Because had he done that it would have been disastrous. There would he would have lost both businesses. Now we had another client come to us post sale, similar paradigm, Gen Xer acquiring a baby when we're business. And he realized that he needed to change things immediately and not leave the status quo post acquisition, but shake a lot of things up. And he needed to know where to shave things and how fast. And that that involved removing certain people very quickly that he would have left on for over a year as part of the original terms and that would have caused a potential implosion of the acquired business. It wouldn't have blown up the, the foundational business, but it would have certainly cost them a lot of time and money and resources dealing with problems of the acquired business that were not readily apparent from due diligence.

So interesting. And yeah, you see a lot of this is the new thing the, the baby boomers are trying to move on. Do you see certain industries that this works better with certain revenue levels that this like what's where are you seeing this really hit home or is it just certain Businesses in general, maybe at a certain revenue level.

Sure. So we prefer to work with clients at the minimum in the 10 to 15 million dollars a year grossing range with at least 25 staff, you know, all the way up to 150 million gross per year. It's not a cap, it's just a general range. The reason why on the smaller side we don't see it to be as effective is because our product and service serves two very important goals. One is to capture everything about how the leader thinks and what they know. Great. We can do that in any size business. But the second part of it is that we built out an incredible blueprint for them to resolve all of the opportunities and threats and issues that are present from their, their business from an executive's perspective.

And we find that when businesses are on the smaller side and are still in that growth mode, they don't have enough horses around them to help execute on implementing the change that's needed to get to the next level. So it's just not a great fit on the second part of what we offer, which is the solution.

Okay. And from a timing perspective, I know this is one of the biggest obstacles you're going to see business owners have is they just, you know, we talked before hitting record. It's just so much of owning a business is putting out fires and this just isn't a fire that's, that's burning right now. And until it, until it is right, whether you're about to sell, whether you, you know, need to step away, whatever. So from a timing perspective, you know, most people think this is going to be months, year long engagement, that we've got to get this out of my head and move forward. What kind of timing are we talking about in helping business owners get this knowledge out and be able to execute something?

Yeah, that was one of the, the most important things that shaped how we approach this because we knew that long term engagements to do what we do would not only fall apart because of the lack of immediate urgency, but also because of the fact that the business is constantly changing. Right. So the information that we pull might be outdated with new information if we're doing it 612 months later on a month to month basis. So currently our process is down to 45 days and we could do it considerably faster, both if the client is motivated and as we're going along and improving our systems and processes. On the back end, we're using the latest in artificial intelligence to carry out what we're doing. So it's more the white glove Interacting with the client aspect of things and making sure they do what they need to do to keep things moving. One thing that you said about it's not always top of mind or the level of urgency. One thing I'd like to leave with our listeners is a way to reframe how they think of urgency.

Oftentimes we'll see business owners getting in the weeds of the problems that are directly in front of them and attempting to throw a certain amount of money, which may seem significant to them at that time, to resolve the problem. Right. And they know what that figure is. They know the time involved in fixing it and they'll push off doing some of this proactive type of work. But if they're really in the mindset of understanding the value of their business and the rate of return. Right. On preparing it to be sold at the right time to the right buyer, they may hold that what appears to be expensive solution temporarily in lesser regard, and prioritize the bigger return.

What do you say to that business owner? Because you mentioned, you know, getting ready for a sale or getting. And there's a lot of people who step into business, they're like, I never want to leave. I never want to, you know, step away from this or pass it off. This is my baby, whatever it is. So let's pretend they live forever. And that's not even an going to be an obstacle. They're going to live forever and they're going to run their business forever. Could I still use what you all do to help me run my business more efficiently? Run my business? Like, can I use it even if I don't intend on selling or I'm not going to get sick or all these things? How can I use what you all do to help me run my business better? For lack of a better term?

Sure. So we're going to pretend that we have. We have cured the human condition. Okay. And this person's going to live forever. And are we also going to pretend that their Ebenezer Scrooge and that they don't have a spouse or children that they're ever going to want to spend time with or to go take care of if they get a terminal illness? We're going to eliminate those as well.

Yep. No sickness. No sickness exists. No sickness or love.

Okay. And we're going to eliminate any of their charitable desires. Nobody wants to go off and do something for others that way. Right. They just want to focus on.

They just want to build a business.

Yes. Perfect. Okay. Remember, I'm still a lawyer, so I'M going to ask these questions. Okay. If they value their time, then working with us allows them to take a step back, put everything very clearly about their value to the organization in front of those around them so that they can choose what to do with their time in their business. And they may be able to take it to greater places because of that time that they have back. If it's about money, they're going to see an inordinate number of opportunities to leverage those around them and their own knowledge and abilities into a lot more money for their organization.

What's important as we share some of these stories from founders and leaders, maybe some who have, you know, overcome some obstacles or, you know, really were able to dial it in and, and let the business, Let them step away from the business for a moment and let the business do its thing. What are some of the takeaways you want listeners to get from these stories and, and get from what we're going to talk about in future episodes?

I've always been fascinated by the older, sagey person that says, like, listen here, young buck. I'm gonna, I'm gonna tell. I'm gonna drop some knowledge on you. I'm gonna tell you some things that you didn't know about. I'm gonna give you some perspective, and if we can just, like, eliminate the annoying aspect of, of how that comes across and listen to the pearls that they drop. There's. There's a lot to be learned from, from, you know, founders and leaders of organizations that have been through it and are now on the other side and can say, let me tell you, if they actually knew everything that I knew, here's how. Here's how things would have gone.

Right. And so I think that I, I want to keep those stories being passed down so everybody can have that perspective.

Yeah. And for me, too, just being part of this, I think it's just so important to know as business leaders. You know, we love to think we're unique. We love to think that we're the only ones struggling with certain issues or certain problems. And, you know, oh, you think you can get there, which is great. But you don't understand what my situation is. I think we all have this ability to really build businesses that we can step away. You know, maybe it's 30 days that.

Would it be great to be able to step away for 30 days and not have a panic when your phone, you know, goes off or all those things, like, or get top dollar for a sale or do all. Like, you're not unique. Like, we can all do this. But there's a certain path that needs to be taken and some just aren't willing to join on that path.

We absolutely value and will help business owners achieve that. That 30 day vacation where they're just not bothered. Emergency access only. That's just scratching the surface. We want somebody that might struggle to take 90 days away from their business. Emergency access only.

Yeah.

Because the clients that we work with, the business owners aren't doing everything in their business. They have C level people around them that are, are paid well and that are high achievers. Right. That's not the issue. The issue is that if everybody knew what they knew, things would be very different. But they can't also just tell everybody everything. That's also something that's unique about what we're doing. Heavy is the head that wears the crown.

It's lonely at the top. There's all kinds of sayings that talk to this, but our clients need to be able to take everything that they know and use it constructively.

Right.

They can't just turn it over to everybody in the organization because there would be mass resignations too. Right. So it's. We're entrusted both in this podcast and as an organization with telling the stories and the information appropriately. Something that our clients don't think about is what is going to, what is their participation going to be in a 90 day period where they're probably needed to be involved, but they're mostly hands off. And two quick scenarios that come to mind are, let's just say there's a bad diagnosis and there's a health scare. Yeah. They can be reached during, you know, many of these scenarios during that 90 days.

But do they want to be, does their family want them to be, does their doctor want them to be? Right. Is the added stress a good thing for them and for the business? So that's on one side, that's on, you know, kind of the sad side. But then let's talk about when we're in like a due diligence scenario. How much does our leader, does our owner really want to have on them to be turning over and non stop being involved in this process? If they're not prepared, not only is it a huge pain in the ass, but they could do it wrong. They can make mistakes. It's very stressful and. And they might blow an opportunity. Right.

And so the idea of kind of downloading everything that you know and handing it off to those around you builds strength in team leadership that wasn't there before. And so it allows us to be much more effective during Windows, where we might be sucked back into being overly involved.

All right, so as we wrap this up and get ready for all our upcoming episodes, is there any. Are there any other parting words you want to leave with the listener?

If they want to know what I know and what other people know, then they'll listen in.

Awesome. Perfect. Thanks so much, Matt.

Thank you, Aaron. This has been great. Thanks for listening. Please be sure to follow us on your favorite podcast player, and if you'd like to connect, Visit us@coatingency.com or find us on LinkedIn.