The Deal Was Perfect - Until It Wasn’t

How does a deal implode when everything looks ready to close?

In this episode of Buyers’ Frenzy, host Will Lindstrom sits down with Michael Morris, Principal at Cana Development, to unpack how human behavior — not market conditions or valuation math — can destroy a transaction at the finish line.

Michael shares real-world experiences from transactions where momentum, trust, and alignment unraveled late in the process. These weren’t broken companies. They were viable deals that collapsed because of last-minute decisions, emotional reactions, misaligned expectations, or leadership dynamics that surfaced too late in the game to recover.

The conversation explores how buyers read signals under pressure, why small moments during diligence can trigger outsized consequences, and how founders often underestimate the relational and psychological stress that emerges once a deal becomes real.

Michael also explains why speed alone doesn’t save deals — clarity does. When ownership roles, decision rights, and communication norms aren’t firmly established before negotiations intensify, even minor friction can cascade into deal-ending outcomes.

Highlights Covered:

• Why deals fail late — even when valuation and diligence are on track
• How leadership behavior under pressure reshapes buyer confidence
• The subtle signals buyers watch for once negotiations tighten
• Why misalignment between partners or stakeholders becomes lethal near close
• How emotional reactions create risk no spreadsheet can flag
• What founders can do early to prevent last-minute deal sabotage. 

For founders and CEOs, this episode is a sharp reminder that exits don’t break because of numbers alone — they break because people change when stakes rise. 

Preparation isn’t just operational; it’s behavioral. And the deals that survive are led by leaders who understand both.

Have insights on “Deal Killers”? If you’re a CEPA, CPWA, CFP, or fiduciary with experience navigating the hidden risks that derail deals, we’d love to hear from you. Connect with us on LinkedIn or at theculturethinktank.com/contact

Chapters

• 0:00 Introducing Michael Morris
• 0:48 Career Path In Healthcare Deals
• 2:40 Ego And Trust As Deal Killers
• 4:27 The Dental Deal That Fell Apart
• 5:39 Building And Trusting The Right Team
• 7:32 Effective Communication Playbook
• 9:21 Vision, Goodwill, And Mediation
• 10:23 Clean Financials And Lending Reality
• 11:34 Can You Have Two Sets Of Books

Transcript

William Lindstrom: 0:01

Hello, everybody. Today we'll be speaking with Michael Morris. Michael is a seasoned deal maker, strategist, and business leader whose experience spans mergers and acquisitions, turnarounds, and high stake negotiations. Over his career, he's seen the deal flow from both sides of the table: buyer, seller, and investor, and has a knack for diagnosing when a deal's trajectory is off course. Today, Michael will be going over some real deal killers he's encountered, how he's caught them in time or hasn't, and the rules he now lives by to avoid repeating these costly mistakes. With that, I'd like to introduce again Michael, and I appreciate you taking the time to share your deal experience.

Michael Morris: 0:38

Thank you, and I appreciate that.

William Lindstrom: 0:41

So, yeah, to get started, I'd love to hear about your deal cars and a little bit more about yourself.

Michael Morris: 0:46

Appreciate that. So, a little bit about myself. I like to say I started in small business banking with Bank of America Practice Solutions. That's their healthcare vertical. That was underwriting boot camp for me. I worked dental acquisitions in the state of Florida for five years. From there, I went to work for a healthcare consulting firm where I performed the same function. I ensured our internal clients that were getting your traditional business consulting were prepared and set up financially to be able to secure the financing needed for their goals and the projects that laid ahead. And more recently, I've got into capital consulting and raising large capital amounts for various real estate projects, mainly ground up and mainly in the healthcare space, but do have a few working with some luxury condos and a few pretty exciting places in the country and MA strategies for a private equity firm. We all know private equity has a huge appetite for healthcare. And I feel the managing partner of the firm I have joined approaches healthcare in the appropriate way and decided to lend my network and my contacts to help build strategies and provide capital for some emerging DSOs and emerging healthcare players that uh don't necessarily have access to that type of capital.

William Lindstrom: 2:03

That's a really good background. And I know as we've talked, as you've gone through this, there's you know certain things that make a good deal and certain things make a bad deal. And as we kind of look at this, are there one or two of those deal killers that or those things that get in the way that really prevent a deal from going through that are both avoidable and maybe not avoidable?

Michael Morris: 2:24

I think the first one and the biggest one hits both those sides. And whether you phrase it as ego or when it gets personal, that is always the number one pitfall. And that's not always avoidable. For me, this is really about trust. It doesn't matter if you're spending and acquiring a practice for $500,000 or a small business, or you're looking to secure $45 million for a luxury condo project, trust in the process is huge. And the older I get, just as a general life approach, old adages are old adages for a reason. They tend to be true. And again, it doesn't really matter the deal size. So staying in your swim lane is something I really try to work with clients on both sides. You're looking to acquire the business, you're an expert in that field, you're looking to build that project, you're an expert in your field, you're you have a history of development. When it comes to the financing aspect and the negotiations, that's why there are brokers, that's why there's individuals like myself, you have attorneys, CPAs, and this team that surrounds you is giving you advice. When a client trusts those around him, those deals tend to move smooth. Everybody in the process tends to want to row in the same direction. You get those deals done. And it's when the individual doesn't quite trust the process or the seller or his team, and that's where you start getting some issues that bubble up. And ultimately, those are hard to overcome. And I've had several deals, and I actually had one, it'll be 11 months, and this is one I'll never forget. But we worked 13 months on this dental acquisition with the real estate in a remote area of the country. So there weren't a lot of options, and it was one of the best situations I have seen. The doctor had worked in the practice for over a year, the seller had not. The transition had taken place, the practice was growing, it was longstanding in the community, the real estate I believed was undervalued. He was getting a great deal across the board on it due to the area of the country, and that's actually where he wanted to live. After 12 months, the buyer and seller sat down to sign paperwork at close, got in an argument, and walked away. And now that seller, who was planning on moving to Nevada to be with his kids, and my buyer who had moved across the country and found one of the very few associate positions and one of the very few offices available to work at, let alone the only office to purchase in the area, fell apart. And everyone's plans ended up getting canceled. And it was really just an ego and a personality situation. It was a win-win-win across the board. When you get into the larger deals, that tends to be the case as well. I always say in the large capital raises, brokers kill deals. And brokers kill deals because of ego and what they quote unquote think they deserve in a deal, as opposed to just stepping back and everyone understanding that it's going to be a win across the board. And if everybody gives a little, then we can land in the middle and we can get the deal done and we can move on and it's going to be great for everybody.

William Lindstrom: 5:24

So how so I guess it's a two-part question on this one on the deal killers. One is ego. So between the buyer and the seller. So how do you avoid that? And then the second question is you know, how do you assemble the right team and how do you get, especially if a buyer or seller have two teams, how do you get those teams working together?

Michael Morris: 5:42

The avoidance is again really just about putting that second piece in place, making sure they have a good team and they trust their team. Because there's always going to be issues every single transaction, and big or small, they're going to come up. And you need to be able to work through them and work through them in a manner that doesn't cause anxiety and stress. Because generally these are stressful situations and these are life-changing events more often than not for the individuals involved. So it's understandable that's how they feel, and just getting them comfortable. So over-communicating with them certainly in the beginning is an approach I take to help build that trust and get them comfortable, bringing individuals to the table if they need them, a part of the team that I know will get deals done. I know how they operate and I'm comfortable bringing them in and letting them own their role. So whether that's an attorney or a broker or a CPA, whoever the case may be. And then just along the process, just making sure you're communicating with the other side as well. And making sure that what we're asking and how the deal is unfolding is acceptable to the other side. And if not, let's get out ahead of it. So we're not getting down the finish line when an emotion pops up that's been trying to somebody's been trying to get hold held in check or someone's been afraid to talk for whatever reason. Just again, overcommunicating, putting good people in place and trying to build the trust between both sides.

William Lindstrom: 7:05

No, that's some really good insights. I've heard communication keeps coming up more and more, but you know, there's communication and effective communication, which are two different things. You know, like I've told them everything I'm doing, I've heard this, but they didn't hear it or they didn't understand what you were saying, or they didn't absorb it somehow. So, how do you so you like kind of what would be two or three of your suggestions for best practices or best in class ideas for effective communication between two teams and two buyers and a buyer and a seller?

Michael Morris: 7:32

I think in person will ever the impact that being in person with somebody will ever change, no matter the technology. There is a line that I was told over and over again when I first started my career, and that's you live and die by email. And what they mean by that is you can email somebody a hundred times, but it doesn't work once or twice, and you're just slowly gonna die because that becomes less effective. And so you have to pick up the phone. And when the phone becomes less effective, then you either have to get in your car on a plane and go sit down with somebody. And even a one-hour sit-down meeting once a month changes the trajectory of that relationship. And I've just seen it over and over again. And it honestly is just deal-dependent for me. So usually the bigger the deal, the more I'm going to try to get in front of that client because there's a little bit more trust that's needed to get something across. Those are a little less standard. The outlets are a little less standard and well known when you're working with private funds and institutional money. I always try to touch base with the phone call. Obviously, communicate with email, follow-ups. Hey, we just talked about this. Here's all the information that we spoke about. It's right in your inbox. You can go attack this. And then just nice steady drips, right? It's a fine line between professional, professionally pushing somebody and you not crossing that line into being, you know, annoying or cumbersome in their life. We just want to be a resource, you just want to make sure, again, that they trust that everything's being taken care of, even though they're not involved in the minute by minute.

William Lindstrom: 9:05

No, that makes a lot of sense. I've I've heard feedback is interesting because in some of the things that we've been looking at, the importance of feedback significantly improves outcomes just because people feel, I think, connected. The last question, just kind of touch on, is as you're working with communication, effective communication, is there a need or is there an alignment of the vision between the two? Because you had brought up the dental situation where one was moving in, one wanted to move to Nevada. But is there a value or or is there a need to have a common vision for both parties that they both understand? So that way they does that improve? It was just an idea or a thought that came up from what you were talking about.

Michael Morris: 9:43

It's deal dependent. It always helps. If there's goodwill between the buyer and seller, that obviously makes negotiations a little bit easier. But I'm very hesitant to work on a deal where a buyer and seller are negotiating directly.

William Lindstrom: 9:57

Okay.

Michael Morris: 9:58

And whether there's representation on both sides or somebody in the middle, I'm happy. And so are many other professionals to sit in the periphery and say, hey, I think this is going okay. Hey, I think maybe you should reach out and talk to your attorney. Again, it's just deal-dependent, but the more goodwill, the more trust there is, the better those deals flow.

William Lindstrom: 10:17

And again, getting back to the importance of communicating and having the right team in place. All right. So with that, we're kind of hitting the end of our little session here. Very much appreciated. So as we wrap up, was there the one thing or the two things that you would want to kind of leave with or the kind of the critical things to avoid in this deal killer situation to make deals successful?

Michael Morris: 10:37

Yes. And this is a this might be 1A, 1B. You know, wish we had a little bit more time, but poor financials. And the one sentence on that, you can pay Uncle Sam and you can get the correct valuation for your business and you can secure financing, or you can have an aggressive tax strategy and pay very little on taxes and show very little net on your returns, but that's seriously going to hamper your ability to secure funds. And that's seriously going to hinder the valuation of your business. So on paper matters.

William Lindstrom: 11:09

So the one thing I'd ask about that, just and maybe we can have another little session together on this, because that's one messy books is one of the things that I've been tracking down and seeing as a sore spot. But the question I have for you, if you just want to leave it, can you have both? Can you have both a tax set of books and a real set or a valuation set of books that are maintained simultaneously that you as an underwriter would accept? Yes.

Michael Morris: 11:33

The short answer would be yes. There's probably some caveats to that. And I think there'd be a balance to that as well. And just one sentence on it, an underwriter is willing to add back a fair amount with great documentation, but at some point there's a limitation. And that's just a there's a federal regulation that came out of 0809. We've all seen the big short, where now lenders have to prove that their borrowers can repay loans. So on your tax return, if you show no income, then the bank technically has to jump through many hoops to show that you can repay that loan. So yes, you can have both. I would say you can't have an extreme tax strategy.

William Lindstrom: 12:11

Okay. That's great insight. And if you do have a few minutes, would love to follow up with you on that one because I think there's a lot of area, especially with AI and how that can be addressed. But with that, I'll just say thank you so much for your time and I'll look forward to catching up with you later.

unknown: 12:26

Thanks.

William Lindstrom: 12:26

Well, I'm missing fantastic. I appreciate the invite. All right, thank you so much.