Ah, January, a time for new beginnings. Or relearning the same lessons more painfully. 

Some predictions for the year ahead: 

• The business environment will be uncertain due to wait-and-see political situation in the US

• Inflation will come back as tariffs are enacted and immigration is restricted

• New tax incentives and cuts will be enacted to take effect in 2026, particularly for real estate and physical asset investments

• You’re going to worry too much about AI-related noise instead of committing to learning how it works and deciding how you want to engage with it 

• Tik Tok will be acquired by someone in the Trump orbit and become a different kind of national security threat (15% is owned by a US citizen who donated $100M to the Trump campaign)

• There will be even more noisy headlines that distract you, sap your energy, and make you afraid

• The fundaments of business will not change -- your pipeline and gross margin will still be your most important metrics

For my part, I continue to build out my team so I can stay on top of business regulations, tech improvements, and changes to our political economy, while I partner with my clients at an elite level, and strive to be a present parent and friend. And maybe make enough money from writing this newsletter to do private sleuthing for ProPublica.

The last time I’ll talk about the BOI

Oh hey, remember back in early December when you didn’t have to file a BOI? Strike that and reverse it, then reverse it again. Anybody else confused? Here’s the timeline:

• December 3: nope!

• December 23: yup, +15 days!

• December 27: nope! (for now)

Before I never write about this again, let me make a final case for why you should file a BOI as a good corporate citizen. This is a national security concern. The BOI is meant to help banks fulfill their Know Your Customer obligations under anti-money laundering (AML) statutes. 

My regulated banking career was entirely around 9/11, so anti-money laundering training and regulation was front and center. The attacks happened on my fourth day on the job as a financial advisor in midtown Manhattan. Some of my dearest friends have made careers in AML at global financial institutions.

Post-9/11, we realized a lot of money was flowing to bad actors like the Taliban through cash transfers, charitable organizations, and corporations. One step was to restrict transfers of more than $10,000 for evaluation. Another was Sarbannes-Oxley (SOX) regulations, which, since 2002, have required publicly held corporations and privately held C-corps of a certain size to file a version of the BOI.

All regulation has unintended consequences. SOX has driven bad actors and tax evaders to set up lots of nested and disregarded LLCs that flow money to one another, making money difficult to track. The Delaware LLC is one of the world’s best money laundering tools, as we saw in the Panama Papers leak of 2016. It’s why you might see someone set up a dozen LLCs to do business with one another. 

For example, you’re a Russian oligarch trying to evade sanctions, but you really want to buy a big boat. So you make the boat its own company in, say, Spain. And you hire staff from another company in Greece. And then you contract the boat to a third entity, a Delaware LLC, to make trips and deliveries through Jersey, which is the Caymans of Europe. You’re doing business with yourself, but all the companies have different names and ownership groups. And they operate at a loss, which ultimately reduces your taxable income and reporting requirements.

If you work at a bank where Big Boat Co wants to open a business account, it’s your obligation to determine whether the owner is trying to flow funds from illegal or sanctioned activities through you.

Are you doing this? Are you secretly evading sanctions, funding global extra state actors and terrorist activities, or hiding money in your offshore accounts? Are you an elected official in Texas who has an ownership stake in the “small business” Texas Top Cop Shop in Conroe, the state’s largest gun dealer to municipal police departments? (That’s the case that started all this, Top Cop Shop, and it’s creating a huge future mess at the Supreme Court level.) 

I didn’t think so. You’re a person who incorporated a company because you don’t want to expose your personal assets should you get sued or find out your business partner is doing shady stuff. Perhaps you wanted to reduce your payroll taxes by having S-corp status. Each year, you’re giving the IRS a report of all the money that You, the Human earned from You, the Business, on a form called a K-1. 

No big secrets here, just honest people trying to earn money from companies the government and your banking partner already know about.

So be a good corporate citizen and file your BOI voluntarily. It’s free and it takes ten minutes. Fincen is taking voluntary BOIs at fincen.gov/boi. 

And thus ends a year of BOI reminders, which has taken far too much space in this newsletter. I’m officially done talking about this. File or don’t. If you have deeply held personal objections to the federal government knowing that you own a company, have your flotilla of accountants and lawyers track the court proceedings for you while they’re nesting your 27 Delaware trust LLCs. 

December AMA

My first subscriber AMA of the  year is this Thursday, January 9, at 10 AM PT. If the Christmas elves in the optical shop did their work, I should have some fresh computer glasses for your sartorial commentary. Come for the Q&A, stay for the lewks.

Send me your questions at [email protected]. Add the first 2025 AMA to your calendar using this link.

 January 1: A slew of new minimum wage increases and paid leave laws took effect. Check your state law updates here. One thing that didn’t take effect: the second phase of the planned minimum salary increase for white collar workers. In fact, fix your face, a Texas judge stayed the January 1 requirement and vacated the July 1 increase, taking the federal exempt salary all the way back to $684 per week. The decision has been appealed. If you are considering rolling back salary increases you’ve already put into effect based on this rule, discuss with a lawyer.

January 15: Federal and state estimated tax payments are due for September through December 2024. Check with your accountant on whether you need to pay now.

January 31: Filing deadline for W-2s and 1099s. If you use a payroll system, you should be receiving notice to review your W-2s any day now. Check that fringe benefits like mobile allowances / stipends, health insurance, QSEHRA reimbursements, and 401k contributions are included. For 1099s, keep in mind that you do NOT have to file if the vendor is an S-corp or C-corp, or if you paid by credit card. More info here. If you received 2024 payments totaling more than $5,000 via PayPal, Venmo, or Cash App, you’ll get a 1099-K from those platforms to report taxes on your earnings.

Men’s Health: I’ve caught my tween kid tracing a finger down the jawline a few times, which seemed weird until this article caught me up on mewing, auramaxxing, and (thank goodness we aren’t participating yet) a big ol’ resurgence of Axe Body Spray and ‘90s colognes called scentmaxxing. If the males in your life are going through gum like gangbusters, read up.

Mashable: Cybersecurity starts at a very basic level: use secure passwords that you reset regularly. If it’s been a minute, make it a January habit. And don’t use any of these. It doesn’t take a criminal mastermind to hack 123456. Set up a password generator / keeper or an authenticator and enforce password quality through Google Workspace or your parent Microsoft account.

Bloomberg Businessweek: Not seeing the performance you once did from Google Search? Your customer may be using their chatbot instead of a conventional search engine. Early adopters -- often the people who will try out small or new companies -- are shifting their searches to AI chatbots like Perplexity. If this is your customer, an SEO or paid search strategy may no longer serve the same purpose. 

Digiday: New reason to hire your kids -- 40% are already making money online. A new study shows one in three teens have been approached with an offer for paid promotion, and two in five are making money online. Let your kid edit your videos and punch up your merch line. While you’re at it, use that earned income to set up their Roth IRA.