Selling My Family’s Business Part 1: The Call That Changed Everything

Lubricant (n.): a substance introduced between moving surfaces to reduce friction, heat, and wear. It forms a protective film that improves efficiency, prevents corrosion, and keeps machinery functioning properly. 

Nate O’Brien spent his summers making it. The irony was not lost on him that his own family, the one that had built a lubricant manufacturing business over fifty years and three generations, had plenty of friction of their own. When an unsolicited offer landed on their doorstep, it forced a conversation the family had been putting off for years. What followed was a reminder that even the best machinery needs constant lubrication, and that keeping a deal, and a family, moving smoothly is harder than it looks. 

In Part 1 of this three-part series, Nate covers the family history behind the business, the decades of ownership complexity that nearly derailed the transaction, and the unsolicited offer that finally forced a serious conversation about selling. 

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I’ve spent over a decade advising business owners on valuations and exit planning. I’ve sat across the table from hundreds of owners navigating some of the most consequential financial decisions of their lives. But nothing prepared me for what it would feel like to do that work for my own family. 

My grandfather started a lubricant manufacturing business fifty years ago. Over time, he brought in my father, my aunt, and two uncles as owners, gifting each of them a 10% interest as a way of sharing what he’d built. It was a generous act rooted in family loyalty. It was also the beginning of decades of complexity that would ultimately shape, and nearly derail, the sale of the business in 2025. 

This was not a business I knew from a distance. My siblings and I went to the Take Your Kids to Work Day there. From the time I was sixteen until my early twenties, I spent summers working in the plant alongside the people who kept it running every day. The chemist, the office staff, the folks on the plant floor. I mixed batches of lubricants and coolants in 1,000-gallon tanks, wheeled 55-gallon drums and 5-gallon pails across floors that lived up to the product, and drove a forklift on surfaces that had no business being driven on. My father and uncles did not just run the business. In their younger years, they physically built parts of it, installing pipes and tanks with their own hands. When I say this business was a part of our family, I mean that in the most literal sense. 

This is the story of that transaction. It is also a case study in nearly every lesson I teach clients about family business planning, lived out in real time, with my own family’s financial security on the line. 

The foundation had cracks before anyone was looking  

The problems did not start with the sale. They started decades earlier, when the ownership structure was informal, documentation was inconsistent, and difficult situations were handled with family logic rather than legal precision. 

In the early aughts, one of my uncles was behind the wheel in a drunk driving incident that killed a fellow employee. The legal costs were significant, and he sold back a portion of his shares to cover them, dropping from 10% to roughly 2%. There was an agreement that he would repurchase those shares over time through payroll deductions. That repurchase never happened in any meaningful way. He was eventually pushed out of the business, only to return nearly twenty years later as a 1099 sales contractor, his ownership status largely unresolved and poorly documented. He received house arrest as his sentence, which the family learned came with a waitlist for ankle bracelets. He got off easy by most measures. I will leave the fuller details to your imagination, except to note that in fifth grade, I had the distinct pleasure of serving as my elementary school’s D.A.R.E. speaker on the subject. Some childhoods come with more material than others. 

A few years later, my grandfather’s exit from ownership was handled through a private arrangement. My father, my aunt, and my other uncle agreed to buy him out by paying essentially an annuity of $50,000 per year after tax until his death, which occurred in 2018. It was a thoughtful solution for the patriarch, but it left the remaining ownership structure with an unequal basis, informal documentation, and no clean mechanism for resolving future disputes. 

Shortly after the deal was signed, around 2007, it was discovered that my aunt had been embezzling from the company. She was eventually pushed out around 2012. What followed was over a decade of litigation threats, claims that she was not being kept informed as a shareholder despite receiving all legally required communications, and persistent attempts to use her 30% ownership stake as leverage. The remaining owners never made shareholder distributions during this period, reinvesting everything back into the business rather than creating financial events that could become fodder for additional legal action. On multiple occasions, they attempted to buy out her interest. She refused every offer. 

Through all of it, the business kept running. And quietly, it kept improving. 

My grandfather had a dozen grandchildren across the four siblings who owned the business. Not one of us had any interest in taking it over. I cannot speak for everyone, but I suspect the years of family conflict around the business had something to do with that. What I can say is that the business shaped me in ways I did not fully appreciate until much later. Those summers on the floor, the relationships I built with people who had worked there for decades, watching my father navigate genuinely difficult situations with integrity year after year. None of that was wasted. It did not make me an owner, but it made me someone who understands deeply what a family business actually is, what it costs, and what it’s worth. That is the work I do today. 

The unsolicited offer that started everything 

In 2023, one of the company’s vendors approached my parents with an expression of interest in acquiring the business. They were drawn primarily to the company’s in-house lab capabilities, which represented a genuine competitive advantage in the lubricant manufacturing space. 

I knew this particular deal was unlikely to close. The prospective buyer did not have the financial capacity to realistically complete the transaction. But I encouraged my parents to engage with it anyway, for one specific reason: it would force them to start thinking seriously about an exit for the first time. 

We completed a formal valuation and presented it to the prospective buyer. The meeting went well. The buyer confirmed what the valuation showed: the business was worth something real. But as I suspected, they could not make the numbers work. The deal didn’t happen. 

After that meeting, I told my parents something I want every business owner reading this to hear. What just happened, a qualified buyer approaching you directly, agreeing on value, and being ready to transact, is a one-in-a-million scenario. If you want to sell this business on your terms, at full value, you need to run a real process. 

They agreed. And we got to work. 

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Selling My Family’s Business Part 2: Building Something the Market Would Buy

Selling My Family’s Business Part 3: What I Would Do Differently