Bad Deal Structure
The Controlling Interest
He owned 28 percent of the company and 100 percent of the guarantee.
The phone call came on a Wednesday morning in November, the day after the tariff announcement.
Greg Fowler took it in his office in Mexico, a hundred steps from a floor where his crews were building aluminum fishing boats. Formed, welded, and rigged by hand, as they had been for 52 years.
The announcement promised a 25 percent tax on everything made in Mexico. Half the country called it a bluff.
The man on the phone did not. He spoke for Greg’s biggest investor, a family office run by one of the richest retail families in America. Someone in that family held a board seat at one of the biggest store chains in the world. Word from that room: the tariffs were real.
The investor had one question. How profitable is North Channel Boats with a 25 percent tariff?
“We’re not,” Greg said. “At all.”
No yelling. No debate. Just one more sentence.
“We want you to sell the company.”
Greg hung up and did the math he had spent two years not doing. He had run this company for seven years. He owned 28 percent of it. None of that mattered, because of three facts on paper. His investor held preferred stock, the kind with special powers. The company’s line of credit stood on a personal guarantee with one name on it. His. And the bank holding that line was owned by the same family as his investor.
His investor. His bank. One family. Under their money, one man’s signature.
The company was still alive. But every door out of the building belonged to the same people, and he had just heard the locks turn.
The Dream
Greg Fowler looked like the man this playbook was written for. Strategy consulting. Banking. A fancy MBA. Mid-career, with a wife and three small kids. He had spent years closing deals for other people. He wanted one that was his.
He paid for the search himself, on purpose. Buy something small, then build the investor group around the deal.
The search was local too. Home was northern Michigan, and three little kids meant no appetite for airports. So his territory was a drive, not a flight, and his method was coffee. Town by town, he sat down with the people every owner trusts. The broker. The banker. The lawyer. The accountant. That circle always knows who is ready to sell.
His first wave of outreach turned up 12 prospects. One arrived as a phone call from a local advisor. “I’ve got a seller in my office. Can you come over?”
The seller was North Channel Boats. Aluminum fishing boats, built on the Great Lakes for 52 years. The founders were retiring. Their kids did not want the business. The management team was solid but could not buy it. And the founders refused, flat out, to sell to a competitor.
Greg drove over.
The Deal
They met in the fall. The letter of intent came fast. The deal closed in the summer of 2017.
The months between sent up a flare. The founders owned 80 percent of the company. A minority partner owned the other 20. Halfway through, that partner flipped from seller to rival buyer and lobbed in a competing bid.
Greg walked. I’m not raising my bid, he said. Then the management team spoke up: we will not work for that guy. The deal swung back to Greg on his terms. He took it as a win. He missed the lesson. In this company, the paper and the people could point in opposite directions.
The price was 4 times earnings. The money stacked up like this:
- 75 percent from a bank loan backed by the government.
- 10 percent in a seller note, owed to the founders over time.
- 15 percent in fresh equity from a small group of investors. Greg wrote the largest check himself.
For finding and running the deal, Greg earned another 30 percent as promoted equity. Sweat pay, paid in stock. Half vested at closing, half over five years. Add it up: Greg held 42 percent on day one. The largest owner in the room. Not the majority.
Now the two choices that shaped everything after.
First, the votes. Greg handed equity to his management team as a thank-you, then set the rules so each member got one vote. Not one vote per share. One vote per person. His own grade, years later: entirely too democratic, entirely too generous. Equity is not the glue you think it is. Every senior chair turned over within five years anyway.
Second, the guarantee. The bank loan required a personal guarantee. Plain words: if the company cannot pay, you pay. Your savings. Your house. Your kids’ future. Guess how many people at that closing table signed one.
One. Greg.
Everyone got equity. Everyone got an equal vote. One man got the debt.
And the business? It broke his own buy box, and he knew it. No recurring revenue. Thin margins. Seasonal. Cyclical. A boat is the first purchase a family cancels when money gets tight.
He stayed for the thesis. Strong brand. Dealers who reordered every year on a steady cycle. Aging buyers who want lighter boats, the company’s specialty. A niche of three, where the other two would not spend a dime on capacity. If we invest in capacity, we can own this growth. That was the bet.
In June 2017, Greg Fowler owned a boat company. Sort of. Keep that “sort of” in your pocket.
The Cracks
The early years rewarded him, which is how the best traps work.
The company took a second government-backed loan and bought its own building. They moved in just in time for the world to shut down.
March 2020. The state closed. Greg sat with the first mortgage statement in one hand and a stack of canceled orders in the other, thinking one word: toast.
Then Memorial Day came, and America rediscovered the outdoors. Retailers called back, un-canceled everything, and doubled their orders. A government payroll program kept his crew together. For two years, the company could not build boats fast enough.
That boom was crack number one, dressed as a blessing. Greg’s logic ran: we grew before the shutdown, we grew through it, so we will grow after. His verdict, later: “No. No way in hell.”
Crack number two was geography. The raw material was 40 percent of the cost of a boat, and it came from Mexico. No plant in the States had room to spare. So in the fall of 2021, North Channel opened a second plant in Mexico. Greg moved his wife and three kids down and ran it from the floor.
January 2022 was the peak. Greg calls it the top of the mountain. The first boat shipped out of the Mexico plant that month. The same month, the big money arrived.
A family office bought into the company. Not just any family. One of the richest retail families in America. Their vehicle was called Rockhill Capital, and it took 20 percent of the company.
But not in common stock, the plain kind everyone else held. Rockhill got preferred stock: stock that gets paid first and comes with special powers. Greg sums it up in one line. Every bell and whistle you could ask for in a preferred structure, they got it.
The money did real good. It paid off the government loan and the seller note. It bought out the original investors at 1x: their money back, not a dollar more. The company stood debt-free except one line of credit.
Greg was running two plants, backed by one of the deepest pockets in America. “The tacos are great,” he says. “Everything’s fantastic.”
The top of the mountain lasted about six months.
That summer, orders came back down to earth. His marriage came down with them. His wife told him it was not working and moved back to the States with the kids. He stayed with the plant. I will not try to make that sound better than it was.
By May 2023, the arithmetic turned brutal. Two factories carried two full sets of fixed costs, with one company’s worth of orders between them. All that growth had never dropped real profit to the bottom line. One plant had to die, and the numbers said Michigan.
Closing a plant costs money before it saves any. Rockhill funded a follow-on round and climbed north of 20 percent ownership. Greg slid to 28.
Then came the decision this chapter exists for.
The move needed a bigger line of credit. The lender wanted the strongest name in the deal on the guarantee: Rockhill. Rockhill refused to sign. Instead, the investor steered Greg to a different lender. Granite Peak Bank.
Granite Peak Bank was owned by the same family as Rockhill Capital.
The bank waived the family’s guarantee. It required Greg’s.
His confession, word for word: “I stupidly said yes. It was a stupid, stupid move. It was a move made out of desperation.”
Rockhill said all the right things. This is really sponsored equity, they told him. We are going to recap it in the future. A recap means new money comes in and cleans up the old debt. Here it meant freeing Greg’s name. Don’t worry, they said. It is never going to be an issue.
Not one word of it was in writing.
The small print told the truth anyway. The company financed new tooling through the same bank. About $140,000 more, guaranteed by Greg. On that loan, the bank waived the family’s guarantee without the family even asking. Even the paperwork knew who mattered.
The Michigan plant closed in the fall of 2023. Greg laid off people with 20 years in the company. In a town he had served for seven years, he became the villain in one news cycle. He can still recite the headline: fancy MBA takes money from one of America’s richest families, shuts the plant, ships the jobs to Mexico.
He told me what the headline left out. He had quietly paid for workers’ funerals. He had sat at bedsides before surgeries. And he was personally guaranteeing the line of credit that paid those workers their severance.
The old building sold at a meaningful premium and returned money to investors. Greg’s own slice, after taxes and after the divorce, was the last liquid money he had. Rockhill required him to put every dollar of it back into the company. He did. His entire net worth now lived inside a boat company he did not control.
In 2024, the headquarters moved to Missouri, near the investor’s home city. Demand stayed soft. Competitors cut prices. Retailers failed and paid late. The summer board forecast showed an operating loss coming. Greg pitched growth anyway: buy a bleeding competitor, add a new category. The board approved the plan. And it promised a recap in the fall to clear the line of credit and free his guarantee.
The cure finally had a date. It still did not have a signature.
The Collapse
The tariff announcement landed in November. The phone rang the next morning. You have already heard the call. How profitable is North Channel with a 25 percent tariff? We’re not. At all. We want you to sell the company.
The promised recap died on that call. What replaced it was arithmetic with teeth. Between Thanksgiving and Christmas, the company fell into default on its line of credit. Not a missed payment. A default on paper: the loan’s fine-print tests broke, and the bank got the right to move. The bank owned by the family. The family that had just ordered the sale.
Rockhill put in a bridge of $400,000 to keep the company breathing, then fed it out a week at a time. Every week, a four-hour meeting about cash. Which vendors to pay. Which to stretch. Greg was building boats, running a sale, and begging for his own bridge money in seven-day rations. The detail that stings: his cash was running ahead of his own June projections. Ahead. It changed nothing.
He finally said it to their faces: “I can’t build these boats, sell the company and manage this business from a cash position with your hands around my neck.”
Then he said one sentence too many. He told the board he would never again run a Rockhill portfolio company. He meant it as protest. They heard it as permission. From that day, the instruction was: sell or sell. Close as fast as you can.
Greg spelled out what a fire sale meant. The common stock: wiped out. The preferred: probably wiped out too. A broken deal: the company fails owing everyone. Then he asked the question under all the others. If this goes wrong, will you leave me hanging on the guarantee?
They didn’t deny it. The answer, in full: well, we’ll see what happens.
Eighteen months of “it will never be an issue” collapsed into “we’ll see.”
Early in the new year, a buyer surfaced. The offer was, in essence, we will take on the debts. That was the whole price. The buyer wanted to close in about three weeks. Three weeks to sell a 52-year-old company with its plant in another country. The fire-sale clock started.
The company needed one more $400,000 loan from Granite Peak just to reach the closing table. The bank’s first demand: Rockhill signs a personal guarantee for the new money. Greg answered with the truest sentence in this book: “The fact that you’re asking for that now is an acknowledgment that you’ve mismanaged your conflict of interest.”
The bank backed down. The new $400,000 went out with no personal guarantee from anyone.
Notice what that proves. The bank always knew how to lend without a person on the hook. It just never needed to while the name on offer was Greg’s.
Mexico nearly killed the deal anyway. To ship the equipment and inventory north, Greg needed sign-offs from his plant partner and landlord, and they knew it. His phrase: “a little bit of a hostage situation.” Costs ran over, the timeline slipped, and the buyer edged toward the door. Greg brokered the fix himself: the bank and the buyer split the overage.
Then the eleventh hour arrived with a knife. The sale agreement, as drafted, had the bank releasing all claims against individuals. Greg’s guarantee would have dissolved at the closing. The bank caught the clause, struck it, and wrote its right to pursue Greg back in. That was its condition to close.
Sign, with your own name still in the trap. Or refuse, kill the deal, and hand everyone a corpse. Some choice. He signed.
The last truck rolled toward the border, the escrow money waiting on it to land. When it crossed, the deal was done. North Channel Boats sailed on. It just no longer carried Greg.
The Cost
Count what was left of him.
The bank was in for $1.9 million on the line of credit. The sale clawed back $1.3 million. The roughly $600,000 gap sits on Greg’s personal guarantee. His 28 percent of the company: zero. Common washed out, preferred washed out, exactly as he had warned. The reinvested building money: gone. The years of below-market salary: gone. “I put every last dime into this,” he told me. There was no family money behind him to break the fall.
He kept a job, strangely enough. The buyer required him to come along, at a third of the market rate. His summary: “I get nothing from you. I get a job.”
Bankruptcy could have erased the $600,000. That door was locked too. He had remarried, and a filing would have put someone he loves at risk in a way that has nothing to do with money. So he made the bank’s workout officer an offer instead. His compromise, he said, was the three months of work he had just poured into preserving the bank’s capital. “The number for me is zero.” When we last spoke, the bank had not answered.
And Rockhill? The family lost real money on the preferred. Hold the two ledgers side by side. Their fund took a loss it will never feel. Their bank recovered $1.3 million of its $1.9 million and kept a claim on one man’s life for the balance. And no one in that family ever signed a personal guarantee for anything. That is what owning both sides of the table looks like.
One more scene, because Greg earned it. On his last day at the Mexico plant, the crew he had just laid off threw him a farewell asado. A cookout, for the man who had ended their jobs. They went around the circle and said what the company had meant to them. Some showed off matching tattoos of the boats they had built. Then, right there in the shop, they gave their boss his first tattoo.
“This is something that was hard and it didn’t kill me,” he says now. “It didn’t break me. I’m stronger.”
One more line of his, the one I cannot put down: “I’ve been breaking dreams and hearts left, right and center. But I haven’t lied to anyone.”
The Lesson
Follow Greg’s percentages. He held 42 percent at the closing and got one vote, like everyone else. He held 28 percent at the end, plus the only personal guarantee. At no point did his ownership number decide a thing that mattered. Control lived elsewhere the whole time. In the preferred stock. In the boardroom. In the loan papers. Other people held all three.
Ownership is a number on a spreadsheet. Control is written in the documents. If you take one thing from Greg’s grave, learn to tell those two apart before you sign.
Greg came back from the wreck with three rules. I will add a fourth.
- Conflicts of interest are real. Paper over them at your peril. His investor and his banker answered to one family. When the tariff hit, neither voted for him. Even good people side with whoever pays them.
- Macro swamps micro. He ran the company well, twice, and it saved him nothing. A virus wrote his best years. A tariff wrote his last one. Your plan does not get a vote on the weather.
- A hard decision dodged becomes a harder decision forced. He knew the guarantee was wrong the day he signed it. Fixing it then would have been hard. He waited for the promised recap, and every quarter of waiting shrank his options, until no real choice was left.
- And mine, the rule this chapter was built to carry: never sign a personal guarantee for a company you do not control. When your investor, your lender, and your board are the same money, every conflict will resolve in their favor. Not because they are evil. Because the paper says so, and paper does not blush.
Here is the strangest part. Greg’s investor never lied to him. Not once. Every term that ruined him was written down in plain sight, with his own signature under it. The truth was enough to bury him. The next three buyers got something worse. They were sold fiction on purpose.