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In newsletter acquisitions, there's a dangerous moment between "we agreed on a price" and "money is in the account." That window can stretch for weeks, sometimes months, and a surprising number of deals fall apart in it.

Here are the stages where a deal can quietly slip away, and what to watch for at each one.

1. Initial agreement on price and terms

A handshake (or a few messages) saying, "Let's do this." Nothing is binding yet, and either side can still walk. The best protection at this stage is momentum: keep things moving, agree on a clear timeline, and don't let weeks pass without progress.

2. Due diligence

This is where most deals die. The buyer digs into the numbers, the list, the contracts, the tools, and finds something that wasn't in the listing. The fix: be transparent from the start as a seller, and ask for everything upfront as a buyer. Surprises kill deals.

3. Asset Purchase Agreement (APA) negotiations

The contract gets drafted, terms get refined, and tension can rise. A deal that felt warm can suddenly feel adversarial. Stay focused on the original spirit of the agreement, and don't let small clauses derail it.

4. Transfer of assets

The list, the domain, the social accounts, the ESP, the sponsor contracts. Each one is a moving piece, and any single point of failure can stall the deal. Use a checklist and a clear handover plan.

5. Funds in escrow then released

Even after signing, money usually sits in escrow until conditions are met. A deal isn't truly closed until that final transfer hits your account.

And after that? Well, the relationship continues. Just look at Politico, acquired by Axel Springer in 2021. Five years later, staff and leadership are still figuring out how to work together. Most acquisitions go a lot more smoothly than that, but it's a good reminder that the handshake is the start of a relationship, not the finish line.

A few quick tips to protect any deal in flight:

The deal is not over until the money is yours, and even then, give it a little time before you fully exhale.

Reply if you've ever had a deal almost fall through; I'd love to hear what happened.

David is my brother; sometimes he likes to act like my dad as well, but above all else, he’s a smart cookie.

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Just like most people don't know you can buy or sell newsletters, most don't know you can stage an apartment to sell it faster (my parents have a blast with our jobs 😄). If you're in NYC, selling, renting, or just want a beautiful space, David is your guy.

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Back in 2021, Axel Springer acquired Politico for around $1 billion, one of the largest media deals of the past decade.

This week, Politico employees sent a letter to leadership warning that Axel Springer CEO Mathias Döpfner's recent op eds risk "undermining our reputation as an impartial news source." Even five years after a deal closes, buyer and seller can still be working out how to coexist.

Wishing all parties a smooth path forward!