A friend's firm, a seat with no fee
A friend of mine, Brandon Holdridge, had built one of the strongest aircraft brokerage records of the pandemic years and made himself the top broker at his firm. Then he left, within days, to start his own private aviation advisory business, BridgePoint Air Advisors. He asked me to sit on the advisory board from the start. There was no fee and I took no stake in the company. He paid me in jet hours, which meant what I held was worth something only if the whole company was, and the seat was written into the operating agreement, one of two advisors, so the exposure was personal rather than contractual.
The firm was in good hands on everything it did every day. Brokering an aircraft, managing a fleet, holding a client relationship together under pressure: he had done all of it hundreds of times, and his confidence on those calls was earned. The clients came because of him and stayed because of him. He built a small team and ran the operation himself for the life of the firm.
What he had never done was make a decision that only exists once you own the company. He had never hired past a team he inherited. He had never let someone go whose paycheck he alone controlled. He had never sat across from a buyer who wanted his company for less than he thought it was worth. His confidence on that side sounded exactly like his confidence on the brokering side, which was the tell. Speed that tracks expertise everywhere except in the one place expertise has not been built yet is where a capable operator gets hurt.
So the seat had two jobs, and only the second one was visible at the start. The first was to be in the room for the entrepreneurial calls, the hiring and the firing, and to stay out of everything else. The second arrived in 2025, when a buyer showed up: a much larger private aviation company, many times BridgePoint's size. Then the job became explaining, to my friend first and then to the buyer, what he was actually worth to a company that big.
Availability, not governance
The reasonable read of a board seat at a firm like this is governance. Show up quarterly, press on growth pacing and risk, give good advice and stay out of the way. That is the correct read if you judge only on what you can see, which was a very good operator running his own business well.
I did not take that read, for a reason that had nothing to do with him and everything to do with what a board is at a sale. A buyer of a relationship-driven advisory firm is not pricing the board roster. A roster is cheap to assemble and any competitor can put one together. What a buyer prices is concentration and dependency: whether the revenue and the judgment travel with a small number of specific people rather than with the business. And a board does nothing about either, because a board dissolves at closing. The only things that cure those risks are an instrument, an earnout, an escrow, a retention agreement, or a person who stays and can answer for the relationships himself. The value of my seat, if it had any, was that I was a person who would stay available at the two or three moments those questions got asked, not that my name sat on a page signed the year before.
| What a buyer prices in a firm like this | What actually cures it | What a board roster does about it | What I did |
|---|---|---|---|
| Client concentration | An instrument: an earnout, an escrow, a holdback | Nothing; a roster is cheap to assemble | Answered it with the founder: the clients came because of him, and he was not leaving |
| Key-person dependency | A person who stays, and paper that keeps him | Nothing; the board dissolves at closing | Reframed the dependency as the asset: he stays, and that is what the buyer is paying for |
| Continuity after the closing | The founder's own terms inside the buyer, and terms for the other holders | Nothing; the seat ends when the company does | Worked the other equity holders' positions alongside his |
The second decision followed from the first. When the buyer appeared we ran the sale ourselves, no banker, no broker, just Brandon and me. A banker earns a fee by building competitive tension, and competitive tension needs competitors and a business that transfers on paper. This was one strategic buyer, a founder with a relationship into it, and a firm whose value was the founder himself. A process cannot price that. A conversation can, if the right person is in it.
The third decision was where to spend the negotiation. His instinct was that the buyer held the cards, because the buyer was so much bigger. My read was the opposite. The buyer was not buying a small advisory to fold in; it was buying him, the relationships that were his, the book that existed because of him, and the fact that he would still be there the day after. That is real leverage, and it is worth nothing until it is said out loud in the terms the buyer uses to price things. So most of the time went into the framing, before any of it went into the number.
How I came at this one
The first question was who was actually holding the stronger hand, and who had to be moved first: the answer was the founder himself, before the buyer, because a seller who underprices himself has already lost the room. That question fit because the whole negotiation turned on his own read of his value. The second question was what a board roster cannot supply at a closing: continuity, which only a person provides, and which is why the seat had to be availability rather than governance.