In our business evolution, there will come a time where we have to take our business to the markets. Unfortunately, not many small business owners realize the value of their business that this transition can be quite difficult to do. With the help of experts in the mergers and acquisitions space, getting your business sold will be a lot easier. Taking the hot seat in this episode is host, Domenic Rinaldi, as he gets interviewed by Lou Diamond for his Thrive LOUD Podcast. Here, Domenic shares more about his superpowers on helping represent business owners to the market as well as buyers who want to acquire businesses. What are the stages business owners go through when looking to sell? What are the checklists to sell successfully? What are the common mistakes people commit when it comes to mergers and acquisitions? Domenic answers all of these and more in this unique interview.

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Mergers And Acquisitions: Domenic Rinaldi On Taking Your Business To The Market With Thrive LOUD Podcast’s Lou Diamond

We’ve got a special treat for you. We are republishing an episode where I was a guest on Lou Diamond’s Thrive LOUD Podcast. This was originally in September of 2019. For those of you who don’t know Lou Diamond and Thrive LOUD, I highly recommend you go check it out. Thrive LOUD is a very popular podcast. Lou is a tremendous individual. He’s a speaker, an author, an executive coach, an all-around great guy, and a connector of people. Some of the people that he’s interviewed on his show are the who’s who, and it’s tremendous information. He pumps out a ton of content and it was a pleasure to be on his show. I hope you enjoy this episode.

We are going to have a heck of a lot of fun because we have one amazing, thriving individual. He is the Owner and Managing Partner of Sun Acquisitions, a Chicago based mergers, and acquisition firm. He’s a speaker, author and host of the M&A Unplugged Podcast. This brilliant gentleman specializes in helping the owners of privately held companies scale, acquire, and sell businesses. He’s passionate about M&As and thrives on helping his clients maximize the value of their transactions. We are here with Domenic Rinaldi. How are you, Domenic?

That was awesome. I loved every minute of that.

Let’s get ourselves kicking and going here. Domenic, I want to ask you a question. You are the mergers and acquisition man, are you not?

I like to think of myself as one.

Share with the audience a little bit about your background because we’re going to dive deep and try to understand the people that you work with and how you do your superpower every single day.

Thank you so much for having me. I’m so grateful. I love your show and I’m excited to share our message. A little bit about me, I own and operate a mergers and acquisitions firm, Sun Acquisitions in Chicago. I have fifteen people. We specialize in helping owners of smaller businesses with $30 million to $40 million in annual revenues understand the value of their businesses. If they’re ready to take their business to market, we represent them and get the business sold. We also represent buyers who want to retain us to go acquire businesses. That has become a tremendous way for a lot of companies to grow through acquisition. We’ve seen and done it all. We don’t work with anyone industry. We’re pretty industry agnostic and over many years, we’re approaching 400 completed transactions.

We had somebody that specialized a little bit more on the smaller end. Give us the size of the companies that you work with. I assume you’re not working with the billion-dollar M&As. You’ve got a different realm that you focus on.

We’re in the companies that do $2 million to $30 million, $40 million in annual revenues. Their enterprise values might be anywhere from $2 million to maybe $20 million, $25 million. Enterprise value, meaning their ultimate sell price. On the bright side when we represent buyers, we represent clients who are doing larger deals than that. Typically, we’ll go up to $100 million, $150 million on the buyer side. When we’re representing a seller, it’s usually $2 million to $40 million.

MAU 57 | Mergers And Acquisitions

Mergers And Acquisitions: Understand what your business is worth and its value in the marketplace at all times, because you may not have the luxury of having time to prepare for a sale.


I asked this question to someone when it comes to looking at mergers and acquisitions and understanding, does it make sense? Do I want to be bought? Do I want to be sold on, whichever side you want to go on? I want to ask you from your perspective and the seat you sit in, what are the stages or what is the most common stage that you run into with the owner of a company that’s looking to sell?

When you say stage, do you mean where they are mentally or where their business is? What do you mean when you say stage? Help me understand that.

It’s twofold. First of all, typically where maybe the stage of their businesses is? Are they very mature? Are they early on in those early sets where they’ve come up with an idea and need a little help to get where they need to? Have they been doing it for a long time? That’s the stage question. Then very importantly, where are they in their mindsets when they’re ready to partner up, make a merger or sell themselves to another organization?

On the business side, it’s all over the map. We have owners who are ready to sell. Maybe they’ve only run the business for twenty years, but they’re at a stage where either they can’t take it to the next level. They don’t want to make the investment to take it to the next level, or they are just burnt out, or something else has happened that’s forcing them to now consider a sale of their business. We have the owners who have run the business for 50 years. Now, they don’t have the next generation and they’re ready to move on. A third-party sale or a sale to the employees or sell to a local competitor makes sense.

It runs the gamut. The big question in all of that is, is their business ready to be sold? Maybe we can get to that later. That’s a much bigger question. On the personal side, it’s one of the key questions that we ask owners when we first sit down and consult with them. Why do you want to sell? What’s pulling you to make this move at this moment? It requires owners to be honest with themselves. When we hear questions like, “I think it’s time, I’ve had this for long enough, maybe it’s time for me to move on.” I question and I become suspect. What I prefer to hear is people who say, “My wife and I, or my significant other and I bought a second home. We love spending time there and I need to be there more often. I’m ready to move on to the next chapter.” That tells me the owner is mentally prepared to move on to the next stage of their lives and not feel remorse after the sale.

Let’s go through what you started to get to in the beginning there. As you sit down and question these prospective clients or partners of yours that you’re going to help make these decisions have you built a given checklist that you know this is something that you’re going to be able to take on and help to be successful? Is there some methodology that you’ve built over the years that works across industries?

Not every owner runs their business to sell it for sure. Click To Tweet

When we sit down initially with a client, we talk about the two phases that they’ll go through. Phase one is the analysis stage, which is what you’re talking about. Phase two is if they are ready to go to market, then how we would represent them and take them to the market. Speaking about phase one, we do go through a multipoint checklist, which includes diving into the financial aspects of their business and understanding what the value range of the business. It requires that we go through a checklist on the key value drivers of their business. I’ll give you an example. Is the owner, the business? Is it a self-managing company? Is it somewhere in between? That has a big impact on the ultimate value of the business.

If you can imagine, if it’s a self-managing business and the owner is not involved in sales and they’re not the key contact or the bottleneck for any process in the business, that business can easily be transferred to the new buyer and the value of that business goes up. We have twenty-plus points like this that we’ll go through with owners in a pretty deep dive conversation and interview to understand. We put together our financial analysis with where the business is at. We then do some external research. We’ll research the market in the industry. We have access to comps across the country for similar deals. We can look at comps and we’ll talk to bankers about, “Would this deal be interesting to a bank to fund if we find the qualified buyer?” It’s a great litmus test. Those are a couple of things that we do in that analysis phase to get our arms around, “Is this business ready to go to market? Can we get maximum value?” The owner has a decision to make. Do they continue to work it and close some of the gaps that we’ve identified? Do they take it to the market?

Let’s go through an example of when you’ve sat down with someone interested in selling their business, and due to your due diligence and analysis, you recognize that this was not a good fit for you or maybe even the right time for that particular company to sell.

We have them every day. We had one where it was a trucking-related transportation business. This scenario is a little unfortunate. The owners are at retirement age. That first question about, “Are you ready?” They check the box in many ways. They’re ready to move on to the next phase. When we went through and did the analysis on their business and then ultimately delivered to them, the value range on the business missed the mark by a wide range. Now, you’ve got this scenario where they’re ready to move on and maybe have even checked out of the business, but what they were sitting on isn’t worth near what they had hoped for. I see this story play out all the time and people ask me, what is the number one piece of advice that I give to people who own businesses? I always say to people understand what your business is worth and the value of it in the marketplace at all times, because you may not have the luxury of having time to prepare for a sale. It may be forced on you. At least run your business and know what you need to do to improve value.

How do you partner with these clients versus being a barrier for them so that they can get to that next level?

When we approach clients, the culmination of the analysis that we do is a presentation. In that presentation, we deliver to them not only what the value of the business is, but all of the value drivers and the roadmap for where the gaps are. They have a decision to make. Do they want to roll up their sleeves, fix those gaps, and spend the money to do that? Are they at a point in their lives where they don’t want to do that? They don’t want to reinvest in the business and they’re willing to take the lower number. If they are willing to take a lower number, then we have to make a decision as a firm whether or not we move forward or we work with them if we think we can get success. If they are willing to roll up their sleeves, what they get from us is this mini-roadmap of where the gaps are, and what they need to go address.

We don’t do the consulting with the ongoing consulting. At least, we don’t do it yet. We’re maybe going to go there in the future. Right now, it’s a roadmap that they get. We’ll then stay in touch with them over the course of 1, 2, or 3 years. We’ll check-in and see how they’re doing. Can we offer more assistance? Because there’s a date on the calendar. They’re going to be ready at some point in time. We want to be there when they are ready.

We had a guest on, Thomas Smale. He made an interesting statement. He says that every business is looking to eventually sell to somebody else. Do you agree with that?

I don’t agree with that. We talked to plenty of owners. They can never imagine doing anything else and they’re going to be there. They’re not going to be there forever. Something is going to happen to that business. If he means it from that perspective, then it’s going to change hands whether the owner wants it to or not, that’s a true statement, but not every owner runs their business to sell it for sure.

Do you run your business to be at a point that eventually maybe someone would want to buy it?

Yes, absolutely. I try to live what I preach, have a self-managing business, and do those things. I’m not perfect at it but we try.

What’s your favorite part of the deal-making process?

Once we have offers in hand and then figuring out how we can get leverage for our clients and maximize the value of the outcome. I love that part of the business. I also love meeting people because I’ve gotten to meet many people across many different industries. I learned so much every day about many different industries. That’s fun but the deal-making part is a blast.

I have a lot of friends from my old Wall Street days. While I worked in sales and trading, I knew a lot of investment bankers and those in M&A. There was one gentleman who had a great summary. He says his two favorite days in the deal-making process was the day that the deal was done, it was inked and signed and they were finished, and the first day he met somebody for the next deal. He talked about the fact that he looked forward to both of those because it bookended the whole experience. What happened in the middle was part of the job, but it was the ability to increase that value and also then meeting new people. It’s very similar. That’s part of the world you’re in. Let’s pull the covers back a little bit. You’ve got a lot of things going on for yourself. You’ve got a book coming out. Do you want to share with us what that is and what we’re going to hear about?

The book is titled Scale, Grow, or Exit. It’s about the blind spots that buyers and sellers don’t anticipate when they go out to either sell their businesses or look to acquire a business. Half of the book is dedicated to sellers and highlighting the key things and the pitfalls that they’ll come up against. The back half is dedicated to buyers and going through the things they don’t anticipate or completely appreciate.

Is there a most common mistake or maybe an incorrect mindset that people have as it relates to the mergers and acquisition world that you live in?

There are two things that I see repeat themselves all the time. One is a lack of preparation, whether it be somebody who owns a business and wants to sell it or somebody who wants to buy it. If you’re buying, having a strategic plan, understanding what you’re looking for, and having your key criteria. The lack of preparation surprises me time and time again. It doesn’t surprise me anymore because I see it all the time, but it amazes me. The other one is advisors. Surrounding yourself with good advisors. In my world, that means an M&A accountant, an M&A attorney, an M&A advisor like our firm, and then while you’re running the business, advisors to help you improve in the aspects, the key value drivers of where you need to improve. Most people don’t know how to move the needle. Having coaches and advisors to help you along the way, those are the two things that I see people most often do not take advantage of.

Over the years, is there one deal that sticks out maybe not because of size, but because of what it meant the most to you? Does that happen in your career? Is there one that sticks out that you’re like, “I’m very proud of that deal?”

Good advisors are the key value drivers of where you need to improve. Click To Tweet

There isn’t anyone deal, but there are some commonalities between the deals that have stuck out for me. They’re the deals where we hit issues. Because we’ve done a couple of hundred deals, we knew how to help our owners or our buyers get through the issues, keep their deals on track, and have a good outcome. I could look at a number of those that have happened along the way. I’m proud of my team because we knew how to get people through it. A lot of deals can die in our world, and having the ability to be creative and keep them alive is something special. The other thing I would say is my friendships. I don’t have the luxury of having clients for 5, 6, 10 years, and develop those friendships. My window with most of my clients is 1, 2 or 3 years and then they’re gone. I sell their businesses or they buy one and they’re just not in our lives. The friendships that I’ve been able to keep, even though I don’t have that ongoing client-vendor relationship, those things stick out to me as being very special in my deals.

I love asking guests on this show this question. You have a successful business. We’re going to talk about some of the things you’re doing in a little bit. You’re always on the go, doing lots of things. Most of the time, you’re thriving. On the days that you’re not quite yourself or not having a super on-day, it’s a little bit off. Your A-game isn’t fully executing. What practice do you seek or what individual do you seek out to help get yourself back on the thriving track?

I’ve had a week like that because my plate is very full. It’s overflowing at the moment. I’m struggling with balance and even the things that I need to remain focused on. The ritual that I’ve developed in the morning keeps me pretty well-balanced and on track. I’ve developed a morning routine that helps me get through tough weeks and tough days and get back on track. It works for me. I’m grateful that I’ve been able to stick to it now for quite some time.

What is this routine? Is there anything specific that you can share?

It’s nothing special other than I’ll wake up very early. I’ll be a 4:30 or 5:00 in the morning guy. I’ll get a cup of coffee. I do a morning diary, which lays out what I did yesterday, what I’m trying to do today. I practice gratitude during that period of time, and then I’ll get to work for a couple of hours. I’ll work for 1, 1.5, maybe 2 hours, and set my day up. I then shut it down and I go for a workout. I try to get an intense workout in and hot steam. By the time I get out of that and I get on my work clothes and get to the office, I’m ready to go. It has revitalized me. It works for me. I stumbled into it a while back. I’ve been able to stick to it and it works.

We mentioned in the opening that Dom here is a speaker, he’s got a book coming out and he has launched M&A Unplugged Podcast. How has it been being a podcast host?

I love it. It has given me a whole new dimension to my life and to my business. You were instrumental early on in recommending me to our friends, Doug Sandler and Strickland Bonner over at Turnkey Podcast. I’m grateful that you led me in that direction. I am grateful because I couldn’t imagine having to launch it without them. Now that I’m doing it, I’m connecting to people I haven’t talked to in a while. I’m having great conversations with new people that I haven’t met. It’s opened up a whole new dimension for me. It’s a lot of fun.

I might have pushed you in the direction of Strickland. There’s no chance I would even direct you towards Doug. That’s great. I’ve had a chance to listen to a few of them. You’re a natural. I knew that coming in. Share with the audience where they could find you, Sun Acquisitions and the podcast.

Our mergers and acquisitions firm is Sun Acquisitions. You can find us at The podcast is M&A Unplugged. You can find me there at and we’re on all of the major platforms like iTunes, Stitcher and Spotify. People can always feel free to reach out to me directly at [email protected].

Is there a date on the horizon for the book?

We are tentatively hoping for the end of October, early November 2019 launch. I’m in the midst of doing all that editing on top of my day job. It’s been a hellacious week because I’ve had some of that to go and do, and everything else that’s going on. It’s been fun.

Let’s have some fun here. Share with the audience if you could and we’ll do the signature question first. What’s your all-time favorite movie?

I was thinking about this because I listened to your show and I know you ask this to everybody. My all-time favorite movie is a no-brainer. Everybody in my family knows it. It’s going to sound sappy and maybe date me a little bit but It’s A Wonderful Life. Every holiday, my family knows on Christmas Eve, I am going to watch It’s A Wonderful Life. It resets that message for me. Not that I needed it because I practice gratitude all the time. It’s such a great movie and the message is awesome.

MAU 57 | Mergers And Acquisitions

Mergers And Acquisitions: A lot of deals can die in our world. Having the ability to be creative and keep them alive is something special.


My family always makes fun of me. I don’t cry at sad movies. I don’t cry at those tragedies. I have a weird sense in certain things, but happy cry. Those moments of gratitude and appreciation. When Jimmy Stewart is running in the snow and he shouts, “Hello, Building and Loan,” I am a waterfall. We’ll have a good way to sign off this show. Dom, you’ve got a great gig, a great show, a great life. If there’s a theme song playing and Dom is walking down the street, think Saturday Night Fever kind of thing. There’s a beat going for Dom that keeps him going. What’s that tune or what’s that song that is the sound of your ongoing thriving way of being?

I’m going to date myself again. I listen to all sorts of music, but I’m a massive Sinatra fan. My Way is always a tremendous theme song for me.

It is a good one and it seems like Rinaldi would have a little Italian in you, let alone Domenic. I’m imagining that also has a connection to you. Dom, this has been a lot of fun. Continue the success at Sun Acquisitions. Continue to enjoy the podcast. I can’t wait to see or hear what’s next on the program. Thanks for coming to the program.

Lou, I’m so thankful. Thank you very much for having me!

Most people don't know how to move the needle. Take advantage of having coaches and advisors to help you along the way. Click To Tweet

To all the readers out there, thank you for joining us. Until next time, keep thriving onward and upward.

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About Lou Diamond

MAU 57 | Mergers And AcquisitionsLou Diamond, Founder, and CEO of Thrive, is a dynamic speaker and master connector who will energize and motivate your organization to explode your sales, retain your clients, and build a thriving culture. For over 25 years he has been a top sales performer, keynote speaker, and performance mentor. Lou is a consultant; best-selling author; podcast & TV host; and CEO of Thrive, helping businesses, leaders, and brands thrive through the power of connecting. Lou Diamond is a dynamic speaker and master connector who will energize and motivate your organization to explode your sales, retain your clients, and build a thriving culture…

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