DealQuest Podcast
Best of 2026, The Deals That Didn't Close, featuring Aaron Single, Andrew Dunlap, Alex Lopez, Victoria Pelletier, Sean Weisbrot, Babu Sivadasan, and David Horwich
Corey Kupfer [00:00:02]
Do you want your business to grow faster? Are you open to new and out-of-the-box ways to drive revenues and increase value? How do you imagine the most successful entrepreneurs and business leaders double, triple, or expand their businesses tenfold or more? The answer is deals. This is a weekly podcast featuring conversations with business owners, executives, and leaders as we reveal behind-the-scenes details that give you, our listeners, the confidence to pursue your own deal-driven growth. On the show, we discuss a huge variety of deals.
Everything from large complex mergers and acquisitions, capital raising, joint ventures, strategic alliances, real estate, affiliate and sponsorship deals, franchising, and more. My name is Corey Kupfer, and I've been supporting deal-driven growth for businesses for over 35 years as a successful entrepreneur, professional negotiator, and attorney. My goal is to help you strategize, plan for, find, and complete deals that will help your company grow faster. Welcome to the DealQuest Podcast. Let's get started.
DealQuest community, Corey Kupfer here, and welcome to this special best of episode. We spent a lot of time on this podcast talking about deals that close or have closed. And today I want to talk about those that didn't. Over the last several months, guest after guest have shared stories about a deal that fell apart at the signing table, a buyer who got blindsided, a seller who was hiding something, or money that was promised that never showed up. And every one of these stories came with a lesson.
After four decades of doing deals, I can tell you there's one saying that every deal lawyer lives by, and actually anybody in the deal world really lives by, which is it ain't done until it's done. So let's start right at the signing table. Aaron Single is the founder and CEO of Voyager, which makes long-term minority investments in independent wealth management firms. When I asked Aaron about the first deal he was ever involved in, I expected a success story. Instead, he told me about a capital raise of about $200 million for a fund. It took 18 months. It made it all the way to signing, and then it fell apart for a reason nobody at the table could control.
Aaron Single [00:00:02]
Actually, the first deal I was involved in, and which taught me a lot about the experience and the challenges of deal making, was my first deal actually didn't close. It was negotiated. I was at the first firm that I worked at, a consulting shop, and we were trying to raise capital for a fund. And we had this relationship with this really large family office and had to jump through all sorts of hoops and risk management teams and board members and do all sorts of presentations. And it was like an 18 month process.
And we were at the close. We were at signing. We had negotiated terms. And at that moment there was a change in leadership at the top. There's a really large family office, very well known, and there was a major change at the top and all the leadership transitioned out and new leadership came on. So it just came out of left field and our deal just fell apart from there.
And it was devastating at the time. It was one of my first deals, a really large deal. It was about a two hundred million dollar investment. And I put a lot of work and sweat into it. And ultimately deal making is about waiting for the right opportunities, creating the right context and right opportunities and waiting for it to happen. You can't force them and you can't be married to them, because people get married to them, make the wrong decisions, and all different kinds of things can hit you from left field.
So that was my first really big deal that I was involved in. Ultimately it didn't close, it wasn't successful, but it really taught me about being resilient, building out a robust pipeline, and just waiting for the right one at the right time.
Corey Kupfer [00:02:29]
I love how Aaron frames that. You can't force a deal and you can't be married to one, because that's when people make bad decisions. Andrew Dunlap learned his own version of that lesson. Andrew is the founder and CEO of Harbor, a holding company that buys established Virginia businesses to keep them in Virginia. He had a manufacturing deal right in his own backyard in Roanoke. Great team, great company. And they were getting close. Then the phone went quiet.
Andrew Dunlap [00:02:29]
Two things. One that took a real scar, and another one that was just a near miss. So I'll tell you the easier one first, then the painful one later. But the first one, we were deep into talks with a great manufacturing company. We really loved it. We loved the team. We loved the guy that had been running it.
They were part of a European conglomerate and they were based right here where I live in Roanoke. And none of our deals we've done are in Roanoke. And so I was pretty excited about having something in my backyard that I could drive by and be like, man, this is a great place, and go visit them and bring lunch and whatever. And great group of guys. And so we were getting very close to a deal. And then we got a call from the guy that was brokering the deal and he said, hey, everything has stopped. Everything was on pause. And he didn't know why. And he couldn't really share anything with us.
And so we just waited, and then eventually we never heard much more than that. And several months later we were looking at the news, we're looking at the European [unclear], like, what happened here? Well, we found out that Samsung had come in and bought the European parent company. And so everything shut down. The whole company was like, everything stops, nothing goes out, nothing comes in while Samsung gets their hands around this. So that was just one of those, you put all this time and energy and effort and love into something, and then Samsung comes and buys the parent and it's like, yeah, that deal's done. I hope it comes back, but that was when it was unavoidable.
Corey Kupfer [00:04:52]
Yeah, who knows? That's a classic example of what any deal person tries to preach to clients or investors or whatever, that it ain't done until it's done.
Andrew Dunlap [00:04:52]
Exactly. Until it's signed and the money is wired, you're not finished. That was a good early lesson. That was last year. And Samsung, if anyone from your team is listening to this, please call me. We still want to do that deal.
Corey Kupfer [00:04:52]
That's a classic lesson. Until it's signed and the money is wired, you're not finished. Andrew's second story is one that left a scar. He spent about six months courting a company. To win them over, he shared his plan for what Harbor would do after the acquisition, including a partnership with another company. You can probably guess where this is going.
Andrew Dunlap [00:04:52]
But then another one, we courted a company for a long time and they dragged their feet a little bit, and so we were a little nervous about that. But we were six months into this, couldn't really get them to commit to a number. They kept asking for more. And so we went up a little bit and thought we were giving them a very fair deal. It was a very fair deal looking back on it. And then they randomly came to us and said, hey, we got another buyer, and we knew that it wasn't PE because they told us they would never sell it to anyone outside the area. And so we thought, okay, why is it stopping? They wouldn't tell us anything. And so the deal just died suddenly and we didn't know any more.
And so we started doing the whole, what happened here? Why did this deal die? We knew them, the CEO was really excited, the whole management team was excited. The owner wasn't really involved day to day, but he seemed to be really positively disposed to us. And we had told them a bit about our plan post-acquisition of, hey, here's what we want to do. We want to build a partnership with this other company here. There's a lot of great synergy. We think we can help each other. And that was part of getting them comfortable with us being the buyer. And so we found out a couple of months later, when it was announced publicly, that they had basically [unclear] and gone and merged with that company.
And so we just got cut out of the deal, and they just said, we'll just do that ourselves. And they went and did it. And that was a huge lesson, to watch this awesome deal that we were super excited for and spent an insane amount of time and money on getting done, and building out our growth, because we thought it was a lot. They were excited. They said they were excited. And then someone killed it on the one yard line, and then they just went and did our plan without us. So it was like, okay, be transparent, but don't overshare, or else you will just get cut out of the solution. So that's one of those things that I felt dumb about afterwards, but we were just trying to win the deal and just did a little too much of that. So that was brutal. I still miss that one.
Corey Kupfer [00:07:16]
You know what? I guess some people may say that I have an amazing ability to justify, but I also actually truly believe it. In those situations, I'm not saying I wouldn't have feelings about it and be frustrated. But ultimately, usually I'll come to the place of, well, if they're the kind of people that would do that, it's probably a good thing that I didn't end up in business with them. It's a gift in a way.
Andrew's takeaway was to be transparent without oversharing. And that's a line every buyer has to walk. Other times the buyer is the one who walks away because due diligence turns something up. Alex Lopez is a CPA who spent years as a financial auditor at a global firm. And today his practice focuses on CFO services, due diligence, and tax minimization. On this buy-side deal, everything looked perfect on paper. Almost everything.
Alex Lopez [00:07:16]
I'll give you an example where it went completely sideways. Luckily we were able to pull out of the deal. And it was a deal that looked very good on paper from the get-go. Look, we had the works. Proof of cash, all the agreements with the customers, the physical observations of the assets. We went real KGB on this one, real intel. We had observed the operation in every which way. Everything seemed perfect. There was one little ratio that seemed off. One little ratio. It was related to insurance.
And we had gotten a half answer about why it was set up this way and why it made sense and blah, blah, blah. And to be frank, we were a bit blinded by everything else. Long story short, it was a multimillion dollar thing, where the seller had effectively cheated on some of the insurance applications, and the real cost of the coverage that was needed was several times what we thought it was. To the point where the deal no longer made sense, we had to pull out.
So it happens. You gotta do your homework. You gotta look under the hood, you gotta kick those tires, you gotta look at things from every angle.
Corey Kupfer [00:09:39]
One ratio, that's all it took. Alex has another that's even more dramatic. You'll hear advice out there that sellers should take all the cash they can at closing because they may never see another penny. On this deal, Alex was on the buy side. The seller was interested. The offer was competitive, but then all of a sudden the seller would only accept cash.
Alex Lopez [00:09:39]
I was working on another deal. I was on the buy side on this one. I had initially made an offer that was a leveraged deal. And the offer price was very competitive. It wasn't quite asking price, but it was very competitive, and the seller was interested in making the deal happen. But then all of a sudden at the LOI stage, so nothing legally binding had been signed yet, I guess another buyer came along and was offering cash, for less. So the seller became very insistent that our deal had to be a cash deal. My guy had the capability to buy with cash, but he didn't want to, because he wanted to use leverage, and at the same time he wanted to keep the seller. There actually was an earnout involved, but it was a small one.
Long story short, the guy was so adamant, and was then willing to make a deal with us that was much lower than the original offer price, but still a little higher than the other offer he had. But something was off now, that insistence on the cash payout. Long story short, turns out he was getting ready to be convicted and go do time for a white collar crime. And somehow he had kept it under wraps. We hadn't found that in the initial round, but towards the end, a couple of weeks away from closing, we uncovered that.
The dude, that's why he was so insistent on getting cash up front, because he had to get his affairs in order. That's an extreme example, but sometimes you just know when something is soft based on the economics and the details of a deal. So again, I thank God for court searches.
Corey Kupfer [00:11:59]
Thank goodness for court searches. Due diligence doesn't catch everything, though. Victoria Pelletier has been involved in more than 40 M&A transactions, and she bought and sold companies of her own, starting with a casting agency she bought at age 20. She's also been on the wrong end of one.
Victoria Pelletier [00:11:59]
The third company that I bought and sold went poorly, because the woman I bought it from misrepresented some things through due diligence. And so I had to sue her and whatever. And so I came out of it, but I reflected on that. What could I have done? And so I often see a lot go wrong because of due diligence. And so I'd learned a lot going into that. So again, she misrepresented, so there was legal action, but there's far too much, I think, missed in a lot of that.
Corey Kupfer [00:11:59]
Sometimes the problem sits across the table from you, and sometimes it's on your own side of the deal. Sean Weisbrot, the founder of SparkFox, spent 10 years in China raising money for other companies before he built a software company of his own. He put in $650,000 of his own money, then raised a $1 million seed round. One of the investors was a friend he had known for six years, and that friend committed half a million dollars.
Sean Weisbrot [00:11:59]
So he's the one that screwed me. He said, I'll come in for half a million, and then he only gave me a hundred thousand. And he promised, he swore up and down for a year and a half that the rest of the money was coming. The other investors, they sent me the USDT immediately. They all sent me USDT. He did a wire transfer. He was also heavy into crypto, but he sent me a hundred K.
We started budgeting, ramping up. We already had our plan to hire more people. We were trying to move forward. That money, that million, was meant to get us over the hump, to get us live, to get first users, to get feedback, and to get to revenue so that we would raise before we ran out of money. But that four hundred thousand dollar gap between what he promised and what he gave was a massive part of why we failed. Because I tried to get other investors. The guy who did the extra hundred thousand, I hit him up twice. I said, look, we're in dire straits. I'm trying to pay salaries. I'm trying to keep going. And he got his LPs to approve an extra 50K and then another extra 50K.
Because to my knowledge, the other investor, who I had known for six years, had promised to find the money and give it to us. And yet he didn't. And so I was trying to keep the boat going, trying to keep the train going. And I tried to find other investors. And what I didn't realize at the time was they heard, we're dying, we need money. And so, no. Nobody wants to fund a dying ship. I think it's fair to say the business died 50% because I didn't know what I was doing, and the other 50% because my investor didn't give me the money that I needed to actually support me.
Corey Kupfer [00:14:21]
I respect how honest Sean is about his own part in it. Sometimes, though, the problem is timing. Babu Sivadasan helped build Stamps.com and Envestnet, two companies that went public. And today he's building Jiffy AI. Back in the 90s, he and his team patented a way to turn any piece of software into a subscription product. Today subscriptions are everywhere.
Babu Sivadasan [00:14:21]
Back then the software companies are very different. When we got that patent on taking any piece of software and converting that into subscription software, basically we altered the software with metering, usage based metering, and so as long as you paid, the software will work. The moment you stop paying, it'll stop. So that was the idea, and then we thought the software industry would embrace that.
We were trying to solve the problem of accessibility. Those days, 300 bucks to buy office software, or 350 at that time or something like that. We thought $19.99 or $9.99, whatever that is, would have been much more accessible to a broader set of people. But most of the software companies at that time, they countered, actually. When we pitched to some software companies, they would say, no, we are already a subscription business, because we are selling you upfront for three hundred fifty bucks, and then every year we are forcing you to upgrade for another two hundred bucks or whatever that is. So you're asking us to take a cut. That is how they felt. So we pitched to a number of firms at that time and didn't come away with anything to show for it.
Corey Kupfer [00:16:41]
The software companies passed, and the rest of the world came around to subscriptions later. I have saved my favorite story for last because it turns the whole idea of a failed deal on its head. David Horwich has four decades in investment banking and growth consulting, and today he runs Horwich Strategic Advisors. Back in the mid-80s, he was at a transportation equipment leasing firm in San Francisco that could raise investor money at a remarkable clip. So the firm decided to use that money-raising machine to start some new businesses.
David Horwich [00:16:41]
And we were going to use that same money raising machine to start up these two businesses. The first was an alternative energy facility that was going to be located up in beautiful downtown Hardin, Montana, and was going to utilize what we termed waste coal. I actually went to Washington, DC, and I had Max Baucus, who was the senator from Montana at the time, [unclear] that waste coal was going to be considered an alternative fuel. And we got it done. And we're now in drawing board stage, and we've got the financial projections put together, and we're getting ready to go.
And at the time the Montana Power Company was required to buy the power under a law called PURPA, the Public Utility Regulatory Powers Act. I think it was 1978. And they were required by law to buy any alternative power that was generated. So we're starting to look pretty real here. We're starting to get out there and talk to construction financiers to put the construction money in, and the Montana Power Company came to me and said, we don't need the power. In fact, we really don't need the power. In fact, we don't need the power so badly that we will buy that contract from you. And they did. So for doing a lot of hand waving and a lot of motion, the firm made a whole big pile of money for looking like we were gonna build this power facility. Didn't happen.
Corey Kupfer [00:19:01]
A whole big pile of money for a power plant that never got built. Sometimes the deal that never happens works out just fine. I want to close with something I shared in my conversation with Sean, because it connects every story you've heard today.
Folks, every guest in this episode lost a deal, and every one of them kept going. Aaron is building Voyager. Andrew is buying Virginia companies and still hoping that Roanoke deal comes back someday. Alex is out buying firms of his own. Victoria, Sean, Babu, and David have all moved on to what's next. So if you're in the middle of a deal that just went sideways, remember what Aaron said. You can't be married to it. Build your pipeline, do your homework, and wait for the right one at the right time.
If you want to hear any of these full conversations, the episodes are linked in the show notes. The one exception is Aaron's episode, which is going to be coming up as part of our special series on RIA buyers who are not the PE-backed aggregators. So look out for his episode in the future. But the other ones are linked below. And if you've got a deal story of your own to share, you can apply to be a guest on the show at beaguestondealquest.com. Until next week, Corey Kupfer signing off. Thank you for joining me on this episode of DealQuest, where we help you understand how deal-driven growth can be your ticket to freedom.
If you are interested in finding out more about my law firm, the services we provide to entrepreneurial and growing companies across industries all over the country, and my partner Brian Megan and I, and my amazing team, just head over to kupferlaw.com. That's kupferlaw.com. And if you want to follow more of my content, head over to my LinkedIn page where I post regularly. I'm Corey Kupfer. Until next week, wishing you the freedom and financial prosperity that I know your DealQuest will bring.
