I am convinced that Anthropic ("Claude"), ahead of their IPO this year, is engaging in major guerrilla marketing. 🦍

Paying X-influencers to go on and on about how much their work is changing with: swarms 🤖, Ralph Wiggum loops ↩️, autonomous agents 👨‍💻, clawdbot on Mac Minis 🤏, etc.

Most of the examples I've seen are basic admin tasks 🤷‍♂️ and not at all intriguing to me from a real impact point.

I've personally spent the last 4-5 months overhauling processes within our firm with AI that I believe is just now starting to impact our bottom line - but it's been a slow, iterative process. ⌛

So the question remains why is AI having such an outsized (even if it's overblown) impact on coding and technology compared to [insert] industry?

The answer, I believe is this:

That's not how tax works.

It's very possible to do stupid things with taxes very correctly.

To boot, the feedback loop is not tight at all for the highest impact decisions. 🐌 Upwards of three years while you wait for an audit notice on significant positions.

Rant over. Let's prove the point by looking at a few real life examples of how you can do dumb things correctly in tax.

Entity Selection - Technology Start-up

You have a great idea for an app - join the club lol. 💽

But in your rush to get to market, you decide to form an LLC yourself so you can raise money from a few friends faster.

When it's time for taxes, you look at your EIN document and see that you're supposed to file a partnership return (multi-member LLC default).

You do that - also on your own - and think damn, those CPAs are a racket. Rinse and repeat this while we grind, fam. 🤝

Year 5, your app goes viral and you get an offer for $15,000,000.

LFG. 🚀

During tax due diligence, the buyer asks "out of curiosity, why you didn't elect to be a C-Corp instead?" 🫣

As a C-Corp, under QSBS, the $15 million (basically all gain) would be non-taxable.

Instead, as a partnership, you're paying 20% capital gains tax - or $3,000,000. 😧

So even with the partnership returns being filed timely and accurately, it was still the wrong choice.

Deductions - Knowing What's Allowed

You buy a rental property and start your journey to passive income freedom, baby. 🔥

And still hell bent to save $2,000 in filing costs, you file your own return - reporting the rental income on your personal return.

Only thing is you forget to take depreciation expense - for 7 years. 🏠

And here's the kicker: the IRS doesn't care about your deductions. They only care about your income. 🔍 So they don't audit you to correct that.

"All good man, I'll just have higher basis when I sell," you think to yourself. 😎

But that's not how it works. 🙅

When you sell a property, the basis is reduced by "depreciation allowed OR ALLOWABLE."

So you still reduce the basis in the property by the "phantom" depreciation not taken.

Again, the rental income reporting was "correct enough" - but dumb.

Tax Deferral - Tenancy in Common Option

An apartment building you bought with a few partners 10 years ago is set to be sold.

You're going to make a lot of money. ✋ Only one hiccup though.

Some partners want to roll the gains into a new property, 🎢 and some want to cash out.

In your search though ChatGPT Pro-Max-Ultra, you see that a 1031 exchange can only be done with identical ownership.

Since some of your guys want out, you give up on it.

You sell, distribute the cash, pay the tax, 💸 and those that want in go back into the market with 23.8% less capital (after tax).

That's not "technically" wrong.

But ChatGPT failed to walk though the Tenancy in Common (TIC) option. The TIC would allow some sellers to 1031 their proceeds into a new property - protecting their capital from tax leakage - while others that wanted out, got out.

This takes timing, planning, structuring - and the IRS could care less which one is done. As long as you do them right.

The Takeaway

In the age of automation, it's going to be very easy to do stupid stuff correctly. Especially in tax planning.

To avoid these traps, you need to know where to look - structuring, elections, timing. 👈

And remember that the best tax strategies aren't in the instructions or on the IRS website. They're learned from decades of dealing with government agencies and knowing what to say when they ask the questions they have to ask.

If you want to get tight on tax planning, talk to a pro.

🫡

Meme Cleanser 🧼

Conner Hursh @ConnerHursh THIS IS WHY NO ONE GOES TO THE MOVIES ANY MORE TOO EXPENSIVE THIS IS HOW THEY TREAT THEIR "STUBS" MEMBERS PATHETIC 2:47 PM • Jan 20, 2026 7506 Retweets 163386 Likes Read 5468 replies

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Roger Ledbetter @rledbetterCPA Teaching my oldest son about taxes Tell him he owes me 20% of his "adjusted allowance" He asks what "adjusted" means Hand him a "publication 17" I made up He asks which deductions apply to him Tell him to read "section 4" (there is no section 4, it's been superseded by 5:53 PM • Jan 27, 2026 104 Retweets 1881 Likes Read 25 replies

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Aditya @adityadotdev The evolution of trash icon 5:2 AM • Jan 28, 2026 2424 Retweets 23730 Likes Read 140 replies

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Kevin Xu @kevinxu Gave Clawdbot access to my portfolio. "Trade this to $1M. Don't make mistakes" 25 strategies. 3,000+ reports. 12 new algos. It scanned every X post. Charted every technical. Traded 24/7. It lost everything. But boy was it beautiful. 2:6 PM • Jan 26, 2026 671 Retweets 14602 Likes Read 469 replies

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Friday Beers @Friday_Beers My DoorDash driver trying to bring me my cheesy 5-layer burrito next week: 9:37 PM • Jan 23, 2026 3303 Retweets 55864 Likes Read 133 replies

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Nick Newman @Nick_Newman Guy saw the forecast and took no chances. 9:52 PM • Jan 24, 2026 2274 Retweets 91375 Likes Read 278 replies

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