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10 of my Favorite Deals Over the Past 10 Years

By Quiet Light
| Reading Time: 15 minutes

It’s hard to believe, but Quiet Light Brokerage turns 10 years old this month!

You know the many cliches about how quickly time moves when you’re having fun? Turns out, they are all true. That’s why it seems like only yesterday that we were opening our doors for the first time.

I’m not one to look back too often and reminisce, but it seems that hitting the 10-year mark is a good time to take a few moments to reflect on what we’ve done over the past decade to make it so much fun.

There is, of course, the successes we’ve had: hundreds upon hundreds of deals closed, well over $100 million in acquisitions, surviving a major recession, and working in an industry that was basically non-existent when we started.

But there were also the lessons we learned along the way and the people we’ve met.

All of this got me thinking about my favorite deals over the past 10 years. It’s funny to see what deals actually stick out in my mind. They aren’t all glorious stories, but they all left an impression.

So here are my 10 favorite deals over the last 10 years and the lessons I learned from them.

10. A Deal to Teach Me About Bidding Wars

The Great RecessionThe Story

In 2010, I received an enquiry from a potential client to help him sell his “deal of the day” online business.  He and his partner would work with manufacturers and distributors who had excess stock of a particular product. If there was enough product, he and his partner would offer a daily deal to their subscribers at huge discounts.

2010 was a rough time as we were still coming out of the Great Recession. Most of the businesses we worked with had dismal numbers.

This business was an exception in every way. Revenues were growing, there was a massive subscriber list, and a huge amount of upside potential. I was super excited to work on this deal…until everything went quiet.

After providing a valuation emailing the owner some information, I heard nothing.

In this industry, silence is almost always bad news.

Rather than let this deal slip through my fingers, I called the owner to let him know that just that day I had toured one of my buyer’s local warehouses and that this buyer was actively looking for businesses like his, which was absolutely true.

The owner informed me that he was just about to sign an engagement letter with one of my competitors, but was intrigued that I had potential buyers in mind. I offered a limited engagement of thirty days, and promised to approach only hand-selected buyers, to which he agreed.

Within 3 days of listing, I had multiple offers on the table. We got an all-cash offer at his asking price.

Why I Loved This Deal

  • A healthy business during a time of general recession. In 2009 and 2010, there were not a lot of businesses showing growth. It was really nice to work with a business that was growing for a change. In fact, this business was off-the-charts on almost every metric. It was a lot of fun to present buyers with a quality business.
  • Being scrappy can pay off. I typically don’t pay too much attention to competition, but it felt good to know that I ‘won’ this deal by being scrappy.
  • This deal opened up an ongoing relationship. This seller went on to sell multiple properties through Quiet Light and also buy a few properties as well. He’s always been a high-integrity client, the type I love to work with.

Lessons I Learned

  • Bidding wars need to be managed. Since there were multiple offers for this business, there was a short bidding war. One of the buyers who lost out was rather upset with how I managed the process.  I learned from this experience that bidding wars, while good in some respects, need to be managed properly. Namely, they need to be managed with clear rules of engagement and a very short timeframe. Ambiguity is a way to make people think they are being cheated.
  • It’s ok to press for a client. I’ve always tried to respect the fact that a client’s business is their business, not mine. As such, I’ve tried to give them the proper space to make a good decision. But that often can come across as being disinterested. I learned that being scrappy and pressing for someone’s business is a way to help show them that I am invested in them.
  • Larger deals are more fun. In 2010 our average deal size was probably around $100,000. This was significantly larger. I learned that dealing with these larger deals was a lot of fun. Both the buyer and the seller had previous experience in acquisitions, and both the buyer and seller brought a level of professionalism that isn’t seen as often in smaller deals.

9. A Deal Which Shows The Importance Of Picking Up The Phone

The Story

I was driving home after work and stopped at a gas station when I got a call from a potential client. He owned a popular woodworking forum and was interested in selling the business.  I loved forums, and I knew that they always did well, so I eagerly agreed to work with him.

Later that night he called back to apologize. Even though he had verbally agreed to hire me, a previous potential buyer reached out to him and told him that they wanted to move forward and acquire his forum. I was entirely prepared to wish him the best of luck with his other buyer.

But rather than tell me that he was going to give me the boot, he explained that he wanted to honor his verbal commitment.

I agreed to work with him, but only on a highly reduced commission.

Why I Loved This Deal

  • It’s nice to get an easy commission every now and then. I don’t mean for this to sound crass or anything, but it’s nice to get an easy win every now and then. That’s only human nature. This was one of the easiest deals I ever had the chance to work on.
  • Honor is currency in deal making. This client had no obligation to me other than his word, but for him, that was enough. Working with someone who exhibits a real sense of honor is a true joy. In any line of work, you meet enough people who are not like that at all. To meet someone totally opposite in nature is a very pleasant change.

Lessons Learned

  • Trust really does work. I’ve run Quiet Light Brokerage with the philosophy that being kind, and trusting other people, is the best approach to business. There have been times when I’ve questioned this approach and times where my trust in people has caused issues. But, more often than not, trusting others has been a huge benefit.
  • Always pick up the phone. It’s easy to turn off ‘work mode’ when you leave the office for the day. With this deal, I was done for the day, but for some reason I decided to pick up the phone. I’m glad I did.

8. Organized Buyers & Sellers Get Better Deals

The Story

I am often amazed by the products and services people are selling and making money with. This e-commerce business sold a unique home improvement sanitation product that I didn’t even know existed before I was introduced to the seller.

But that’s not what makes this one of my favorite deals.

This makes my list at #8 because the seller and the buyer in this deal were so great to work with. Both of them were passionate about making a good, workable deal that benefited both of them. They were respectful, organized, and reasonable. When we ran into a problem, they had enough business savvy to work through the problem to find a solution.

The seller was extremely organized and had put a lot of thought and consideration into the sale. The buyer was extremely considerate and thoughtful at every step of the transaction.

I’ve often told people that one of the best parts of working in this field is meeting incredible people. That was definitely the case with this deal.

Why I Loved This Deal

  • Organization makes everything easier. The seller in this deal was organized. Not just a little organized, but organized to a fault. That made the deal easier for everybody. Being organized and well documented is a GREAT way to add value to your business.
  • Buyers and sellers who care about good deals are a pleasure to work with. It’s completely understandable that some buyers and sellers focus primarily on their personal goals in a transaction. But it’s a real joy to work with a buyer or seller who understands that a good transaction benefits everyone, not just themselves.

Lessons Learned

  • I need to be more organized. I’ve never bragged about being highly organized, but when I saw the impact organization had on this client’s business and eventual sale, I realized just how awesome and powerful being organized can be.
2009 Website
Our website around 2009. I still like this look and feel.

7. The Deal That Showed How The Most Cash Doesn’t Always Win

The Story

The beginning of 2010 was a really rough time for myself and for Quiet Light. Several of the people I hired a few years earlier as brokers moved on to other work, and I myself had just gone through a family emergency that pulled me away from everything for over a month.

I turned the calendar to 2010 to find the business out of money and struggling.

In February, however, things changed. A client who had done several deals with us approached me about one of his properties. He wanted to sell his rapidly growing web directory.

As I mentioned in #10 on this list, 2010 marked the end of the Great Recession in our industry, and this deal was the first in a series of deals that promised a turnaround for the economy.

We ended up receiving multiple offers on this listing. The winning offer didn’t provide the most cash, but it promised a simple structure, an easy transition, and a one-week close.

Why I Loved This Deal

  • It signified the end of the recession and the beginning of the recovery. This was the first in a series of deals in 2010 that would really mark the end of the recession.
  • It introduced me to a repeat client. The seller was already a repeat client. The buyer would go on and buy a few more businesses from us and also hire us to sell one of his other properties. They also referred the seller from #8 on this list.

Lessons Learned

  • The most cash doesn’t always win. The winning offer was about $25,000 less than other offers. While cash wins the day in most transactions, there are often other motivations behind selling a business.
  • Speed closes deals. The buyer won out on this offer because they promised a one-week close and a quick transition. For someone who is ready to sell their property, speed is often a compelling negotiation strategy.
  • Simplicity closes deals. The offer with the most money attached to it also had a lot of complicated conditions. When we compared the offers side-by-side, there wasn’t much to consider. The simple offer was the obvious choice.

6. A Well-Timed E-commerce Sale On a Seasonal Business

The Story

In 2008 I had hired my first round of brokers. Unfortunately, they didn’t take off like I had initially hoped they would.  We struggled through 2008 and carried those struggles over to 2009. Money started to get tight.

So in the spring of 2009, I realized that I needed to take on a few clients of my own to bolster our working capital.

One of the clients I took on sold a Halloween-related product and was in the midst of their slow season. I had never really seen a truly seasonal business like his before, but I was amazed at just how stark the difference was between off-season and peak season sales.

We closed his acquisition in June of that year which provided much needed capital to the firm.

Why I Loved This Deal

  • It saved my bacon. When I look back on the history of Quiet Light Brokerage, there were several moments in our early days where funds were extremely tight. It seems as if a deal would always close, just in time when we needed it the most.

Lessons Learned

  • Inventory reporting is a pain. We had a lot of conversations about inventory on this deal. If you aren’t tracking your inventory closely, start doing so. Trying to go back and manage inventory tracking is an absolute nightmare.
  • You can’t be afraid to walk away from a deal. During the process of preparing my client’s business for sale, we had a significant disagreement over an item that I knew would negatively impact the value of his business. Even though I needed a closing, I offered him the opportunity to walk away from the deal. By being willing to walk away from this deal, I was actually able to save the deal in the end.
Website Design
Yikes. Its amazing we stayed in business with a site like this.

5. The Time I Didn’t Sell a Client’s Website

The Story

I had actually worked with this client for over a year as he prepared and positioned it for sale. After working with him over this period of time, he asked if I would be interested in selling a premium domain that he owned.

We don’t typically sell domain names, but this domain had an existing website with revenue and was an obvious strategic fit for a professional sports team. So I agreed to work with him.

After I reached out and started negotiations with this professional sports team, my client asked me to lie about offers we received from other buyers. Since we hadn’t even approached other buyers, I explained that I wasn’t going to lie to get a better offer for him.

We mutually agreed to go our separate ways during that phone call.

Why I Loved This Deal

  • I don’t fire clients often…But when I do, it’s for a good reason. I love this deal because I can look back on it and know that I did the right thing. He went on and sold his domain for an undisclosed amount of money, but I don’t regret my decision at all.

Lessons Learned

  • Nothing is more valuable than reputation. I lost a commission when I refused to lie, but I’m totally comfortable with that. Over the past 10 years, I can look back on some decisions I wish I could have reconsidered. The lesson here was that making the right decision isn’t something I’ll ever regret, even if I lose out financially.
  • It’s easier to walk away when times are good. Although I’d love to take all the credit for making a moral decision, it’s easier to walk away when you have flexibility.

4. The Toughest Deal I Ever Closed (And I met Amanda Raab)

The Story

One of the major lessons I’ve learned, and tried to teach to other people, is that you can’t get enamored by the big payday.

This deal makes my list mainly because I violated that lesson.

In 2014 I was approached by a potential high-value client. He and I discussed listing his company, and eventually he entrusted me to the sale of his business.

It wasn’t very long before I found myself making compromises that I otherwise wouldn’t have taken. Instead of being a good advisor to my client, I put myself in a position where I wasn’t able to offer good advice.

Throughout this entire deal I was miserable and stressed out. I kept telling myself that I had already invested so much time and energy into this deal that I might as well see it through and get paid for it.

After 6 months of extremely difficult negotiations we managed to close this deal.

Why I Loved This Deal

  • It was a challenge. Even though the deal was extremely difficult, we did manage to close the deal. I am not sure if I have ever had as difficult a negotiation as I did on this deal. Closing the deal felt like a major accomplishment.
  • I was introduced to Amanda Raab. Before Amanda Raab joined QLB as an advisor, she was one of our potential buyers and she looked closely at this deal. I learned during this deal just how intelligent she is and how good she is at analyzing businesses.

Lessons Learned

  • Know your value and stick to it. This lesson definitely came from the school of hard knocks. Early on in this process I allowed my client to reduce my value and my role in the transaction in a way where I couldn’t be as effective.
  • Don’t get enamored by a commission. This is easier to say than it is to do, but whenever I find myself driven by a commission, bad things happen. When I am driven to do good deals, good things happen. It’s a lesson I’ve earned the hard way.
  • Intelligence stands out. I am super lucky to deal with some incredibly intelligent people. But every now and then I come across someone who really stands out above the rest. It amazes me how really intelligent people tend to stand out.

3. The Deal Which Introduced Me To Joe Valley

The Story

Many of you reading this probably know who Joe Valley is. For those of you who don’t, Joe is one of the most successful advisors in the industry of online business brokerage. He has set high-water marks within Quiet Light Brokerage in terms of the number of deals closed and also deal volume in a single year.

I almost didn’t hire him.

I was first introduced to Joe when he called me to get a valuation on a business he owned at the time. I remember speaking with Joe on the phone in my living room and listening to him explain why his sales were somewhat flat. Although I don’t remember all of the specifics, my first impression of Joe was that he was a bit rash and lacked an even temperament. But anyone who has worked with him knows just how wrong that is.

I didn’t actually sell Joe’s business – Jason Yelowitz had the honor of walking Joe through the process of selling his business. Several months later, on Jason’s recommendation, Joe joined Quiet Light as an advisor.

Joe's Deal
A snapshot of Joe’s listing

Why I Loved This Deal

  • It introduced me to Joe Valley. When people ask me what makes Quiet Light successful, I always explain that it is the people. While we have processes and methodology to working with our clients, my focus has been to ‘hire’ highly skilled entrepreneurs. Joe has proven just how well this approach works.

Lessons Learned

  • Don’t judge people by one thing that they say. My first impression of Joe was incredibly incorrect. Take the time needed to get to know someone before judging their abilities.
  • Always work for the client’s interest first. Joe likes to tell people how I reviewed his business and essentially told him to ‘go away’ and how this set me apart from all the other brokers he interviewed. The truth is, Joe’s business would have been a difficult sell, but it also had a pretty clear path to added value. By putting Joe’s well-being first, not only was I able to win his business, he would later become a trusted advisor.

2. Discovering The Blueprint For Hiring Successful Advisors (And Meeting Jason Yelowitz)

The Story

I’ve already recounted how 2009 was a very difficult year for brokering. With the Great Recession, there just wasn’t much activity.

So when Jason Yelowitz called me to sell a group of websites, I was happy to work with him despite a few significant challenges. Revenues were down and Jason had recently bought the sites which never comes across well to buyers.

But the timing was good. Jason and I struggled a bit to find a buyer, and the negotiation and sale of his business definitely had its struggles. But in October of 2009 we closed on his business.

Why I Loved This Deal

  • It introduced me to Jason (who showed me who I should work with). Six months after I sold Jason’s business, he asked me to come on board as a broker. I wasn’t really interested in hiring new people, but thankfully he was persistent. Jason would go on to quickly become my most successful broker and provided a blueprint that I have followed to this day at Quiet Light.

Lessons Learned

  • What makes a good broker. Jason provided a blueprint that I use to this day: partner with entrepreneurs who have first-hand experience buying, selling, and building their own significant online businesses.
Our first website design
Our first website design. I have no idea why there is a golf ball.

1. You Never Forget Your First Deal

The Story

When I sold my first company in 2004, I thought starting my next venture would be easy.

Little did I know that 10 months later I’d be staring at the prospects of being broke without a viable business or source of income to my name. That is, of course, until a good friend and client from a previous job asked if I would help him sell his web hosting company.

This friend knew that I recently sold my business and he had decided it was time for him to move on from his business as well, so he enlisted my help.

When I first thought about starting a brokerage firm, I naively thought “how hard could it be?” It turned out, it was a bit harder than I originally thought!

Despite a complete lack of knowledge in this space and no real background, we managed to find a buyer, negotiate a great deal (looking back on it, it was a really solid deal), and get the business closed.

I received that first commission on the very day that my funds ran out. If I hadn’t received that commission, the only pennies to my name would have been in the couch cushions.

Why I Loved This Deal

  • It was my first closed sale! I might be nostalgic, but there is always a special place for that first closed sale.
  • We got a really good deal. I didn’t really know how to value businesses at the time, and looking back, our asking price and expectations were really out of line. That said, the business was solid and we ended up securing a solid deal.
  • It launched QLB! This was the deal that launched Quiet Light! Of course I love it!

Lessons Learned

  • “How hard can it be?” proved to be a stupid question. Just because something looks easy doesn’t mean it is easy. Every profession has its nuances and small details that sets professionals apart from lay people. Humility in business is an important trait to success.
  • Closing deals is genuinely good fun. Despite the serious consequences if I didn’t close this deal (going broke), I nevertheless had a blast doing the deal. This style of negotiation is very rewarding. I love helping people – something that has propelled Quiet Light forward for the past ten years.

Moving Forward To The Next Ten Years

While it’s fun to look back on the last ten years and think about all of the great people we’ve met and worked with, I can’t help but also look forward to the next ten years.

When I started Quiet Light Brokerage, FrontPage extensions were still a thing (you may need to refer to Wikipedia if you are fairly new to that world). Today we are now looking at an Internet of Things, platforms, multi-channel sales systems, and advanced inventory automation systems. There is no doubt that the world of online business will morph along with these changes at the same time, and change the brokerage industry along with it.

As for me personally, I can’t wait to see what the future holds.

3 replies on “10 of my Favorite Deals Over the Past 10 Years”

Comments are closed.

  • Mark,

    I love this piece not just as a reader but for what it must have meant for you. I ended up selling my last business almost exactly 10 years after starting it. I wish I had taken the time to reminisce a bit like you’ve done here – maybe at the 5 year mark and again the 10 year mark. I’m sure it was both great therapy and great reinforcement for you!

    1. It was more fun than I expected! I initially thought it would make for an interesting blog piece, but it turned into a fun project (thus, 4,000 words of content).

      Looking back was definitely a worthwhile project. I think doing so every few years is a good idea.

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