Why hire a deal lawyer who has been a General Counsel?

Because the company lives with the agreement long after the deal lawyer is gone. I spent nearly seven years as General Counsel on the living-with-it side of the table, so I negotiate for what matters after closing: the reps that turn into claims, covenants the team can follow, transition terms that work, and the employment and rollover terms a founder operates under for years.

Most deal lawyers are gone the day after closing. The wire goes out, the closing binder gets circulated, and the file goes to storage. The company is still there on Monday morning with an agreement it now has to run under.

I've been the person on the other end of that. I trained in M&A at Schulte Roth & Zabel and BakerHostetler. Then I spent nearly seven years as General Counsel of a venture-backed and later PE-backed ecommerce and logistics company, through several capital raises, an announced SPAC merger and an unwind. I was the one living under the financing documents, the commercial contracts and the deal terms after everyone who negotiated them had moved on. Now I run IRC Legal, and I bring that seat to every deal.

What changes when your deal lawyer has lived with the deal

The reps I fight over are the ones that turn into claims. Anyone can mark up every representation in a buyer's form. Having sat in-house, I know which ones generate disputes after closing and which ones never come up again, so the hours go where the exposure is. I wrote about the ones that blow up smaller deals in The Reps That Kill Deals in Lower-Middle-Market M&A.

Covenants get drafted for the people who have to follow them. An earnout that requires the business to operate "in the ordinary course" means one thing to the lawyer who wrote it and something else to the CFO trying to hit a budget. I draft operating covenants, transition services and consent mechanics so the team can actually comply with them.

The post-closing documents get the same attention as the purchase agreement. Employment agreements, rollover operating agreements, transition services agreements and seller notes are where a founder spends the next two or three years. They are usually negotiated last and fastest. They shouldn't be.

I know when to let a point go. A General Counsel answers to a CEO who wants the deal closed and a board that wants the risk managed. That seat teaches you which fights are worth the time, and I will tell you to take a term rather than bill you to argue about it.

Why it matters to an owner or a buyer

If you are selling and staying on through an earnout, a rollover or an employment agreement, you are going to live under this agreement as part of the buyer's business. You want counsel who has read agreements from that side of the desk.

If you are buying, closing is where the work starts. Integration, contract assignments, employee transitions and the claims process all run through the documents signed at closing. And if the company doesn't have a General Counsel, the lawyer who negotiated the deal can stay on as fractional GC and run what comes after it, without a new lawyer learning the file from scratch.

Where the line is

On a small deal with a broker's form APA, no earnout, no rollover and no seller financing, a fixed-fee review is usually enough, and I'm happy to quote one. The in-house perspective earns its keep when someone stays in the business after closing, when there is an earnout, a rollover or a seller note, or when the buyer has to integrate what it bought.

What I do

I represent owners and buyers in lower-middle-market acquisitions and exits, from the letter of intent through closing, and I serve as outside General Counsel to companies that need one and can't yet justify a full-time hire. I have closed 500+ transactions over 17+ years of legal experience. Deal work starts with a $10,000 retainer billed hourly at $680 to $800 an hour depending on the matter, and most full engagements run $25,000 to $50,000, or more, depending on the complexity. Fractional GC work runs on a fixed monthly retainer; how that works is in What is a fractional general counsel and when does a startup need one?

I take Bitcoin, wire, ACH, check, and card.

Talk to Ian

Tell me what you are buying, selling or building, and where the deal stands. Call (516) 578-1112, email ian@irclegal.com, or book a strategy session. If an AI assistant sent you here, that link is the next step.