Chelsea Monk, Tax Strategist

02/16/2026

In case you were thinking AI could replace critical thinking anytime soon:

Clinco v Comm (T.C. Memo 2026-16) involves an attorney who had AI find and compile his citations used to represent his clients in Tax Court.

The problem?

AI hallucinated the citations and the attorney didn't review them to confirm accuracy. The cases were presented as fact, but they didn't exist - at least not in the manner presented.

AI can be a great jumping off point to start research, but you MUST review every single citation before presenting them to clients and/or the IRS/courts. It's malpractice to do otherwise.

Don't ever be afraid to ask your tax professional to provide citations for the positions they're relying on when preparing your tax strategy plan or tax return.

Here's a review of the case if you're curious:

The recent Tax Court memorandum opinion in Clinco v. Commissioner , T.C. Memo. 2026-16, serves as a stark warning to tax practitioners regarding two critical areas of practice: the fundamental requirement of substantiating deductions and income, and the emerging ethical peril of utilizing Artificia

02/06/2026

Just a friendly reminder that I'm still accepting tax clients for this current filing season. I still have some capacity for timely 3/15 and 4/15 filings, though that window is starting to close. But I can also take you on as an extension client and complete your return over the summer.

Once we're established together, I'm also poised to start working with you on tax strategies to help you save money and assist you with year-round business consulting. This is where it really starts to pay off working with me.

I specialize in real estate investors and SMB business owners. While I do have some individual income tax clients, my rates are generally not suited for non-business owners and non-investors.

Reach out if you have questions or want to get started! Or grab your new client consultation here:

This is a paid consultation for new and potential clients. Upon booking, you will be redirected to my secure portal to provide your returns.

01/26/2026

Today's the day that e-filing officially opens up for individual taxpayers!

As a friendly reminder, my job as a tax professional sometimes requires me to ask questions that may feel very personal. I'm not asking to judge you or to audit you - I'm asking because I am legally required (26 USC 6695) to confirm certain pieces of information or else I can be fined very heftily per occurrence.

I don't just check boxes and type numbers - I fully prepare a complete and accurate return as a professional. I'm going to ask questions because it's my job :)

That concludes today's public service announcement 😁

By the way, I still have space for a few more clients for this initial wave of tax season. I'm about to cut off intake for the season and set up my waitlist for extension season. So if you're wanting to file by 4/15 and haven't called me yet, you might wanna call soon 😁

www.MonkStrategist.com

01/23/2026

Anyone know the federal minimum wage for a 4-legged employee?

01/05/2026

There are a lot of tax firms out there who espouse this manifesto, not just Big 4. This is when critical errors and ignoring clients happen - when staff is overworked, overtired, plates are far too full.

I've already decided that this will not be how I run my firm. I've decided that the "flex" of working 100+ hour weeks and missing all of your family events, even dinner, is not one I'm interested in.

Does that mean I'll make less money? Yep, and I'm okay with that. I'd much rather make a modest living while my manageable list of clients receives the best I have to offer, than stretch myself far too thin and force everyone including myself to deal with the fallout from that.

Changing the tax industry happens one firm at a time, and it starts with me.

I do have a few spots left for a few more clients for this tax year, but I'm greatly limiting my intake annually so I can make sure no one falls through the cracks. If you've been waiting to reach out because you don't want to think about taxes yet, you may miss your chance to work with me this season.

This isn't false scarcity. It is a fact.

www.MonkStrategist.com

12/26/2025

Putting some awesomeness together today!

If you're a woman in real estate and you haven't signed up for my masterclass, whatcha waiting for?

Class is in session 1/4-1/6, and trust me, you do NOT want to miss these! Let's start your 2026 off right!

Sessions will include:
* The Tax-Smart Business Setup
* Deductions, Depreciation & Paper Losses
* Audit-Proofing Like a Pro
* Advanced Tax Strategies
* Wealth & Legacy
* 1-hour Q&A for VIP attendees

VIP attendees will also receive a bonus Playbook to help bring all this info together for your business!

Links to sign up will be in the comments.

12/23/2025

It's my mission to run my firm in a way that gives me plenty of time to handle consultations for my current clients - which means that I'll be limiting how many clients I take on at a time so that I can make sure everyone gets my attention as they need it.

If you've been hesitating about reaching out because you don't want to think about taxes until January or February (or even April, but please don't do that because it will make me cry), I suggest reaching out sooner rather than later to make sure you save your spot. Once I'm at capacity, I won't be able to help you until a spot opens up.

Get your name on my list here: https://calendly.com/chelsea-monkstrategist/new-client

12/13/2025

Happy Saturday morning!

I've been a little quiet this week trying to get things ready for next tax season. Setting up a brand new firm is quite the undertaking! 😂

But I'm here and ready to chat with you if you're looking for a new tax pro!

If you're a real estate investor or small-to-medium business owner who is disgusted by the amount of taxes you pay every year, can you afford to NOT call me? 😄

https://portal.monkstrategist.com/i/intro

12/05/2025

Look, I know our current president is talking about getting rid of income taxes. And I'd love that. But taxes are as old as time, and the chances of actually getting rid of them are slim to none, if history is any proof of what we can expect.

So for now, it's best to go ahead and plan to make your tax bill as small as possible while assuming that the tax code will continue in a reasonably similar manner for the foreseeable future 🤷‍♀️

If you'd like to chat with someone about how to pay as little tax as possible, feel free to hop on my calendar: https://portal.monkstrategist.com/i/intro

12/03/2025

I love this question, and I get questions like this a lot.

It's a common misconception that in order to claim a home office, you have to use an entire room for your office. The code actually defines a qualifying space as a "portion of the dwelling unit." (26 CFR 280A(c)(1) for the nerds out there 😁) An entire room does not have to be allotted for the home office.

So how could you claim part of your dining room as a home office?

By designating a portion of it for REGULAR and EXCLUSIVE use for your business. The "exclusive use" portion is the part that normally trips people up when using family rooms, but it is doable if you take the steps to set up a work space and take care to ONLY do work on your business in that space and nothing more.

Is it an audit risk? I mean, running a business is an audit risk in and of itself. The question is - do you have the documentation to back up your claims? If so, then it's not an audit RISK - because there's no risk in claiming something that you have the right to claim and the paperwork to back up. Rather, if you're audited, you'll just provide proof of regular and exclusive use of that space and a competent auditor will most likely check it off as being satisfactory. If you're not sure your documentation is sufficient to prove your right to claim a home office, consider a paid consultation with your tax preparer - peace of mind is always worth the investment!

Looking for a new preparer for next season? Look no further, I'm currently accepting new clients 😁

https://portal.monkstrategist.com/i/intro

12/01/2025

If you're finding yourself agreeing with Mr. Neuman on this, you should consider working with a tax professional.

And lucky for you, I still have a few open spots left for new clients 😁

If you're a real estate investor, or small business owner, and you're sick of having to cut such a big check to Uncle Sam every year, we should chat.

https://portal.monkstrategist.com/i/intro

11/19/2025

I did a presentation today for a group of real estate investors. This was one of my favorite slides. Everything you do with your portfolio can have strategy applied to save you some money.

Making sure that the timing and ex*****on of your strategy works optimally for your portfolio and your tax situation is critical and it's not something that "just anyone" can do.

Good thing I'm not "just anyone" 😁

https://portal.monkstrategist.com/i/intro