Solopreneur Tax

CPA for entrepreneurs, sole prop, & small business. Bookkeeping, taxes, & payroll. Content is not financial or legal advice.

[End3of6Days9 (Helen) 🇺🇸 @end3of6days9]

A retired Michigan couple, Jerry & Marge Selbee, spotted a loophole in Massachusetts’ Cash WinFall lottery.

The loop hole was when the jackpot hit $2 million with no winner, the money “rolled down” to lower prizes — turning a $1 ticket into $1.10–$1.20 expected value.

They started buying hundreds of thousands of tickets during roll-down weeks like it was a full-time job.

Then a group of MIT students discovered the exact same loophole and began competing against them to buy as many tickets as possible.

Together, over the next 9 years, they legally won $26 million gross… pocketing more than $8 million in pure profit.

The state investigated everything, but no rules were broken. So they shut down that game down forever.

[Curt Philipczak, CPA @CurtPhilipczak]

Some tax practitioners say it’s a myth .. I’m here to tell you it does exist. The “shoe box” tax return was as just dropped off … (please say a prayer for me) … :)

[Solopreneur Tax @solosherpatax]

Yikes.

[Chris Koerner @mhp_guy]

I walked into Cabela’s tonight for the first time in 5 years.

I notice the sign also says Bass Pro. Huh. Whatever.

I walk in and they say “welcome to outdoor world!” Uh, ok. Three names? Wasn’t the merger a decade ago?

There are more employees than customers. Total crickets. 77,000 empty square feet.

The dude at the entry gives me the hard sell to join their rewards program, while the outside air is still on my neck.

I’m just here for a knife dude. I won’t be back for another 5 years.

I wrangle from his grasp.

As we go to leave they push me to join their rewards program yet again.

What a trainwreck. This is what poor management looks like.

[StockMarket.News @_Investinq]

The CEO of a $3 trillion company just admitted the biggest threat to AI has nothing to do with the technology itself.

It is YOU.

Satya Nadella spoke at Davos and said the real obstacle to AI is getting people to actually change how they work.

He gave a personal example.

Before Davos, his team would spend days preparing briefing notes, filtering up through layers of staff before reaching him.

That process had not changed since he joined Microsoft in 1992.

Now he types one sentence into Copilot and gets a full 360-degree brief in seconds what Microsoft is doing for a client, what that client is doing for Microsoft, the whole picture at once.

Nadella said that kind of capability does not just speed things up, it completely inverts how information flows through an entire organization.

The old model, departments hoarding knowledge, information trickling upward through hierarchy, is now structurally obsolete.

Most companies have not figured that out yet.

He said firms will see almost zero productivity gains from AI unless leaders actively redesign their structures, retrain their people, and rebuild how context moves through the organization.

The companies that refuse to change will not just fall behind and they will become irrelevant to the ones that do.

His exact words: "That's why you're going to see the challenge of why am I not seeing immediate results in productivity. You have to do the hard work."

The hard work is convincing an entire workforce to let go of how they have operated for decades.

That is the actual AI race and most companies are losing it before it even starts.

[Nate Sosa @natesosa_CPA]

Private jets are one of the sexiest of tax strategies

But in 2024, the IRS announced a brand new audit campaign specifically targeting private aircraft.

You CAN deduct a private aircraft. But you've got to actually use it for business.

First, you have to prove 'ordinary and necessary' under § 162 which is not the easiest hurdle to overcome on the front end.

You have to prove that flying commercial isn't more economically viable is how I'd phrase it

§168(k) gives you 100% bonus depreciation (back in full force thanks to the OBBB). That means you can immediately expense the full cost of an aircraft in year one.

Sounds incredible. And it is.

But here's where people blow it:

→ You need more than 50% qualified business use under §280F. Fall below that? You're on the alternative depreciation system. Slow. Painful. Not what you signed up for.

→ Post-TCJA, ALL entertainment use is nondeductible under §274. Flying to the Super Bowl to 'meet a client'? I'm not sure that works

→ §274(d) requires substantiation. Not only a flight log, but they want passenger itineraries, ground activity receipts, business purpose documentation, and the relationship of every person on that plane.

→ § 469 Limitations: Let's not forget equipment leases have almost NO ability to be considered 'active' (as always, it depends)

This isn't like REPS where you keep a daily activity log and you're solid. The IRS is going deeper on aircraft. They're trained to look past the flight log and ask 'what did you actually do when you landed?'

I've seen people take full bonus depreciation on a jet and have zero documentation to back up business use.

I wouldn't call that a um 'grey area'

And if you lose? You're looking at full recapture of that depreciation, plus penalties, plus the IRS imputing taxable compensation to every passenger who took a personal flight on your dime.

Here's what you actually need:

→ A legitimate, documented business purpose for every single flight
→ Contemporaneous logs (not the ones you build after you get the letter)
→ Clear separation of business vs. personal vs. entertainment use
→ An allocation method that holds up (occupied-seat hours or flight-by-flight)

The strategy works. 100% bonus depreciation on an aircraft is a massive deduction. But the execution has to be airtight.

If you're considering an aircraft, or already have one, this is NOT something to figure out at filing. It's a planning conversation that needs to happen before you buy.

Whitepaper in next link if this was interesting to you!

[Solopreneur Tax @solosherpatax]

Will be interesting to see how the market responds.

[United Airlines @united]

The entire row is alllllll yours.

Welcome to United Relax Row, three adjacent United Economy seats with adjustable leg rests that can each be raised or lowered to create a cozy lie-flat space for stretching out...

You'll also get a mattress pad, blanket and two pillows. If you’re traveling with kids, a plushie too! United Relax Row will be available starting next year on more than 200 of our 787s and 777s, each with up to 12 of these brand-new rows.

https://t.co/bzHodhQ5Y8

[Solopreneur Tax @solosherpatax]

It’s a start.

[unusual_whales @unusual_whales]

Delta is suspending its special service desk for members of Congress until TSA is fully funded, per MorePerfectUnion.

Delta says members of Congress will now be treated like all other flying customers, per MorePerfectUnion

[unusual_whales @unusual_whales]

Delta is suspending its special service desk for members of Congress until TSA is fully funded, per MorePerfectUnion.

Delta says members of Congress will now be treated like all other flying customers, per MorePerfectUnion

[Brad Nelson | CPA & Fractional CFO @bradncpa]

If your accountant is using AI tools to work on your return, ask them one question:

Is the software SOC 2 compliant?

SOC 2 is the AICPA standard for data security. If the tool does not have it, your EIN, your financials, your business information, all of it is leaving their system without protection.

A lot of accountants right now are running client data through tools that send every input directly to OpenAI and Anthropic.

The client never agreed to that. They signed an engagement letter with their CPA, not a frontier AI lab.

I've spent real time testing tools that do the inference locally so nothing leaves the machine.

The technology is close, but it is not ready for firm-level use yet.

For now, ask the question.

Any accountant worth working with should be able to tell you exactly where your data goes and why.

If they can't, you have your answer.

[Wealthy Accountant @wlthyaccountant]

Here is why your tax accountant is so stressed.

[Codie Sanchez @Codie_Sanchez]

"Men only want one thing... and it's disgusting."

Men: "A cashflowing business, babies and a happy wife."

[Solopreneur Tax @solosherpatax]

Wish this was satire.

[LinkedIn Lunatics @LinkedInLunat1c]

Watching the clock

[Patrick Dichter @patrickdichter]

I felt this video. Most employees have no idea how expensive it is to keep the business running. And most think every owner is making huge profits when they’re often scraping by.

[Solopreneur Tax @solosherpatax]

And what do they expect to find there?

[unusual_whales @unusual_whales]

40% of American women, ages 15-44, would like to permanently move overseas, if possible, per Gallup.

[Diana Panchenko 🇺🇦 @Panchenko_X]

Kyiv ranked third in Europe for Bentley sales, - regional Director of the company, Richard Leopold.

The average price of a Bentley starts at $400.000.

After Europe gives Zelenskyy another 90 billion, there's every chance of taking first place.

[Bark @barkmeta]

Let me explain what just happened 👇

5 minutes before the President announced a halt to attacks on Iran… someone placed a $1.5 BILLION bet on stocks going up and dumped $192 million in oil.

5 minutes…

These trades were 4 to 6 times larger than anything else in the entire market. Whoever did this wasn’t guessing. You don’t risk $1.5 billion on a hunch.

There was zero public indication this announcement was coming. No leaks. No press. Nothing. The only people who knew were in the room when the decision was made.

Someone in that room picked up a phone.
And within minutes they made more money than most Americans will earn in a thousand lifetimes. In a single trade. On a war that cost you $4+ a gallon gas and $16 billion in tax dollars.

American citizens funded this war. Politicians are profiting from it.

This is not the first time. Every major announcement from this administration has had massive suspicious trades right before it dropped. Tariff reversals. Policy shifts. War decisions.

This is the most blatant insider trading operation in the history of American politics. It’s not even close. And it’s happening over and over in broad daylight.

You would go to federal prison for trading on a tip from your cousin. These people are front running war decisions with billion dollar bets and nobody will ever ask a single question.

Nobody will be investigated. Nobody will be charged. By tomorrow this will be buried under the next satisfying headline. Just like last time. And the time before that.

The game is rigged. And they’re not even trying to hide it anymore…

[StripMallGuy @realEstateTrent]

Serious question:

Exactly how large is the “hate apps” population?

[Solopreneur Tax @solosherpatax]

What a horrifying life.

[Boring_Business @BoringBiz_]

Advice for navigating politics in corporate jobs

> perception of work is more important than doing the work itself

> try putting your name on as many successful projects as possible

> do anything you can to keep your name off projects that are bound to fail

> make your boss look good in front of their boss

> show face at every happy hour but never drink too much and say something stupid

> realize nobody is your friend. minimize criticism of the company or your manager, even in front of people you trust

> figure out the locus of power and who the key decision makers are for promotions. get as close to them as possible

Just my few cents, but have seen this exact playbook work time and time again

[Kurt Supe, CPA & Retirement Planner @KurtSupeCPA]

JP Morgan just released their 2026 retirement guide.

One finding that should be in every financial planning conversation right now.

Retirees actually spend more in early retirement than they planned. Not less.

The "I'll spend less when I'm older" assumption is backwards.

Early retirement is when people travel, renovate, help kids, and finally do the things they delayed for 30 years.

The spending curve goes down eventually. But not at 62. Not at 65. Not usually until the mid to late 70s.

If your retirement plan assumes conservative early spending, it may be built on the wrong foundation.

Source: JP Morgan Asset Management 2026 Guide to Retirement. For informational purposes only.

[Solopreneur Tax @solosherpatax]

100%

[Justin Welsh @thejustinwelsh]

The most dangerous financial plan is a single salary, a big mortgage, and the hope that nothing goes wrong.