I’ve been terrible, but I want to change

I own a pass-through LLC in a creative field with a revenue of about $150k/yr, and ~$20-30k in expenses; no employees, so $120-130k profit. That’s the good part!

The bad part? That doesn’t go as far as it seems with single earner and a big family, healthcare, etc. I get paid in lumps just a few times per year, with the great majority coming in the last quarter. Last year we went in to the red before hitting that last quarter, couldn’t pay quarterlies since we needed the capital to continue, and thus will likely be paying penalties when we file. This has every likelihood of happening again this year, but I want to start digging myself out of that tax cycle. Obviously, I need to unfk my personal finances, but to start, I need to unfk my business finances.

Just like you’d guess for a creative… I’ve gotten lax with bookkeeping: keeping files with misc receipts, sometimes no receipts since getting a dedicated business credit card (just figured I’d use the statement, which I gather from reading…is not audit friendly), and paper invoices. I’ve used business checking for personal purchases, but only save and enter valid receipts for tax purposes at filing time, same with the occasional cash purchase. I do try to learn about tax law and keep clean in “substance”, despite my lack of organization and record keeping.

The structure and accounting is exceedingly simple: revenue from 3-5 different entities, which account for sales tax on their end. Expenses are supplies and tools, travel, shipping, etc.. no contract workers or labor requiring 1099s at this point. No inventory, occasional asset purchases, which the tax guidelines help determine depreciation on.
Revenue should continue growth, but this basic model will very likely remain this simple for the next decade+, possibly indefinitely.

Questions are:

I’d like to start using software to help keep up on bookkeeping so I have a better picture of it during the year, and so tax season isn’t a nightmare. I am not tech savvy, and my desktop stays off weeks at a time. Mobile is preferred. I use turbo tax because my business is simple. I may find my way to a CPA at some point, but at this time of year, I’m guessing I’ll be on my own for this filing. I know QuickBooks integrates with TT, and it seems like most CPAs prefer it when I get to that point. Is it overkill? Can I use a basic version? Will I be able to reconcile the books from 2023 manually or by importing bank statements for instances where I don’t have receipts? (I have so few supply types I can easily tell which category an expense is from the statement alone. I’ll keep all receipts now).

I have read that using the S-corp election for filing taxes may be advantageous at this income level, though setting a reasonable salary in this field may be arbitrary since it’s basically a %100 freelance sector with incomes from negative up to 7 figures. Could I do that for 2023, or doesn’t it need to be structured in advance? Should I plan for it in 2024?

Hopefully I can get on top of it so I can possibly file quarterlies to account for the lopsided timing of my income and preserve capital while avoiding the penalties from missing 1040 ES payments.

Any advice is welcome, thank you!
 
@daughteroftheking1029 You need to talk to a CPA. Usually you have to elect for S-Corp status within 2 months of the beginning of the calendar year if I’m not mistaken. You will save a lot of money in taxes, but you will need to setup payroll and pay quarterly taxes. Your CPA will help with all of that.

Quickbooks is pretty much industry standard, and if you work with a bookkeeper they are likely trained in Quickbooks. If you’re making $150k gross, you should just pony up for the annual fee on QB.

A good accounting firm will file your business and personal taxes for you. You shouldn’t be worrying about dealing with TurboTax anymore.

Unless something changed, you need to find a CPA ASAP if you want to elect for S-Corp status this year. You only have a couple weeks to get everything setup for that. While you are discussing that, you can see what you might be able to do for your 2023 taxes.
 
@nubber Thank you so much! I wasn’t sure how the election worked, but glad to know it needs to happen right away if it does. I’ll see about trying to find a local CPA.
It’s a pretty introverted line of work, and well, honestly I have probably just been scared of going that route. The business has grown from a place where preservation of capital was paramount, and that mindset is hard to lose. But my business has grown up, is consistently profitable, and I’m starting to see they can more than likely save me more than I spend on their fees.
 
@daughteroftheking1029 It’s not hard, you just need a CPA to help you. I think it cost me 2000 or so to cover the initial setup of everything, filing of business & personal taxes, and that included email and phone support for the year. That being said, at your income level I wouldn’t be shocked if setting the S-Corp up properly winds up saving you $10k-$20k in taxes. It can potentially be more depending on what’s considered a reasonable salary in your line of work.
 
@nubber That’s very helpful. I don’t imagine the savings will be that substantial, since to get there I’d need to claim something like a 40k salary with 80k in distributions, which is an obvious red flag for audit. Nonetheless, I do think it could help.

If things continue to go well, there’s reason to believe I could double revenue in five years. At that point, it may not be useful at all since a reasonable percentage as salary would exceed the FICA cap and I’d just be paying extra payroll expenses. Something to consider I guess when talking to a CPA (currently on the hunt for one).
 
@daughteroftheking1029 I also come from a "preservation of capital" upbringing, but, from what I can see, not having a CPA/accountant cost you in penalties this year. So you're already burning money. Your CPA/accountant will likely end up saving you money in the long run, based on what you've shared.
 
@powerofthreemovement Yes exactly. Problem is I’m burning money essentially as interest. I knew I’d pay for it later, but I needed the cash then. The penalty is essentially interest on a “loan”. I very much dislike this, and want to get ahead of it, but for now it’s just what it is. Perhaps it would have been cheaper to pay the quarterlies, and borrow capital from a HELOC or something for just the few months I needed to get through to payday so the cash was borrowed for a shorter period, albeit at a higher rate.
 
@daughteroftheking1029 Setting up and managing your own bookkeeping is pretty easy with the level of complexity you are describing. Quickbooks is definitely the standard, we use Xero and really like it. Just having that in place will get you a good portion of the way there.

If you get things tracked well and get a handle on the cashflow, you can pay yourself more often regardless of the S election. How you handle taxes is just a little different. With the S election you can put yourself on payroll, issue a W2, withhold taxes and all of that. Without it you are doing "guaranteed payments" which won't have any tax withheld so you'll have to handle that yourself.
 
@proverbs31an I agree. I don’t mind learning a new skill to help keep costs down, but that’s certainly the goal. It’s just so strange to transition to the idea that my time (and stress threshold) is actually valuable in a field where it’s so common to spend a decade learning that skill at a loss. It becomes deeply engrained. But looking at it now, it’s becoming obvious that anything I can outsource which isn’t a core piece of what I do is a good value.

Also, looking at taking the s-corp election, it looks like that is probably necessary. I don’t think I have time to do payroll, monthly, quarterly, and yearly tax filings. I’m sure the pros are efficient at it and bundling everything is wise.
 
@proverbs31an For sure. After the responses yesterday, I scheduled a couple consultations for this week. I’m not sure if it’s the right way to go or not, but I am convinced I need to get a CPA on my team to help walk me through these things regardless of which direction I end up taking.
 
@daughteroftheking1029 Hey there, based on the information that you provided I think that you'd be a good candidate for an S-Corp election to save some money on taxes this year. You can make a late S-Corp election retroactively in the year that you file the return, I have helped many of my clients do just that. I am a Southern California CPA but service many of my clients remotely, I'll drop a link to my website below if you are interested in chatting further about your situation!

https://www.gainestaxsolutions.com/
 
@daughteroftheking1029 Sounds like you need a CPA. You really should have one, it was one of the first things I did. Getting mail from the government and I take a picture and send it to my CPA, they deal with it. Knowing that stuff is covered is fantastic and necessary. Mine doesn’t do book keeping. Is around 2k a year, does payroll and personal taxes as well.
 

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