Hey folks, I'm experimenting with writing some basic tax background for SMB buyers. I have both some tax and transactional experience so hoping I can translate tax jargon into plain English. Putting up the first bit here to see if there's interest. Note, excerpt continues in comments since I ran into the word limit.

Feedback on substance, style, or items I should cover welcome. Not legal advice obviously b/c if it were, I'd charge you lots of money for it.

The Taxation of SMB Acquisitions in Plain English
Taxes are the price we pay for a civilized society.
Oliver Wendell Holmes
Lawyer fees are the price you pay to avoid (some) taxes.
Another (Slightly Less) Wise Lawyer

The epigraph on top of this page may be true, but the tax system of this particular civilized(?) society has become rather more complicated since Mr. Holmes’s days. Many an ETA entrepreneur finds herself rather confounded by this complexity. This little essay will try to lay out the basic tax considerations in SMB acquisitions in the common tongue so the herselfs and himselfs of the ETA world are a little less confounded.
I will only discuss taxable acquisitions here, both because most SMB acquisitions will be entirely taxable (with the most notable exception being some deals involving rollover equity which are carefully structured with the advice of smart lawyers like the humble one writing these words). And yes, there are various forms of acquisition that are not taxable, in whole or part, primarily because some or all of the same people owning the company before the acquisition still own it after in modified form.
In general, under the U.S. tax system, you only pay tax when you realize income. Your meme stocks may have gone through the roof, but until you turn them into cash in your pocket, you don’t pay tax. Once you sell, the tax man wants his share so he can keep your society civilized. (Query if meme stocks and civilized should be used in the same paragraph.)
When you take the big bucks you’ve cobbled together from your life savings, your brother, uncle, SBA loan, pari passu lender, and six investors who want daily updates, and hand them over to the seller, it’s tax time.
But how exactly that tax time plays out is very important to you, so you either (1) shouldn’t be an idiot about it, or (2) you should hire someone who is not an idiot about it so you can get idiot-proof guidance. I’m writing this so that you can do option one, and then realize you might want to do option two too. (Sorry, the phonics of that sentence ending are compelling me to drop ballet shoes here