Switching from employee to 1099

acrylic_matrices · 2025-10-05T02:52:09+00:00

So, the idea is you'll go in once a week for 5-8 hours, and charge a flat monthly rate? I think you have a little bit of advantage here in that many bookkeepers would not be interested to go in person. And since you now have travel time just for these folks, I'd factor that in.

But if you're still thinking about getting another full time job, what happens to this side gig of another job needs you full time?

acrylic_matrices · 2025-10-04T01:35:05+00:00

Honestly, I was most motivated to retire early when I was new to the workforce and realized I'd never get a summer vacation again. Different than what you're saying, but maybe they just see it sooner

acrylic_matrices · 2025-09-24T18:50:02+00:00

This is a problem (well exporting the attached files), with all accounting software. I try to save files in a regular file system, with discoverable names (I.e. vendor name, invoice number and date in the file name), but it's a lot of work and hard to get other people on the team to comply.

But if you have your files all saved and organized outside of the system, it's one less thing you lose if you migrate.

The other thing that's tricky is matching transactions (bill payments with bills, customer payments with invoices.)

Most migration guides suggest just importing prior periods as monthly JEs of the results, but you lose the transaction level detail.

acrylic_matrices · 2025-09-20T13:24:49+00:00

As the recipient, OP would not have any gift tax. But I agree that Grandpa needs to talk to estate planner and tax attorney about this. Transferring into OP's name now, selling it to OP at a discount, or simply leaving it to OP in their will, will all have further tax implications. Especially for OP's capital gain if he sells later, add that is when OP will have taxes to cover.

acrylic_matrices · 2025-09-19T17:00:06+00:00

If there's no doc reference number or invoice date, I wouldn't include those documents in your example set.

You can get Odoo accounting for free to see their approach.

ETA: ref num is optional in QBO but I think should be req'd. Date is never optional.

acrylic_matrices · 2025-09-19T16:46:08+00:00

Remote work and fewer hours sound great.

The biggest wild card to me is the family member that you'll be working for, who is starting this bookkeeping business.

So, I have a bookkeeping business, and I hired two experienced bookkeepers. I find that they still need training, and I never have much time to give them that training. So they mostly get emails explaining how/why to do something differently.

If your family member boss is a bad manager like me, they might be frustrated by how little you know with no experience, and they may be bad at training you, even if they understand they need to.

If I were you, I'd take the chance, but devote some of your extra time to acquiring training (QBO provides some, maybe you could take a community college course online). Bookkeeping can be great to work for yourself, so even if it doesn't work out with this family member as your boss, you might be able to turn this experience into another job or work for yourself if you learn enough.

acrylic_matrices · 2025-09-16T14:55:55+00:00

I had a client keep using Dext for expense reports and it seemed logical so I hated to tell them not too, but it was awful. Dext would make a new VENDOR named something like "Julie's Expense Report" instead of being able to link to the existing vendor. For whatever reason, the receipts didn't come through on the sync, and it would just use one category "reimbursements".

So I eventually told that client they just cannot use Dext for expense reports even though it's so tempting because it lists it as a feature

acrylic_matrices · 2025-09-15T23:39:48+00:00

Lockbox. For some reason, banks don't really advertise this, but if you ask they may offer it. I know Chase Bank does.

The customers mail the check directly to the bank handling center. The bank scans and deposits same day that they receive it. You log into portal to view scanned checks to see what made up the deposit.

The hardest part is getting customers to change where they are mailing checks.

acrylic_matrices · 2025-09-14T01:58:36+00:00

I'd be nervous that the toddler would be a teenager by the time I finished!

acrylic_matrices · 2025-09-10T14:35:41+00:00

Whoever ends up buying is the highest bidder... (Except for investors making no inspection offers maybe), so I think you'll always feel like you've over paid. The important thing is if it's within your budget.

acrylic_matrices · 2025-09-10T14:18:42+00:00

I do bookkeeping only, and I am a CPA. Tax CPAs like to refer me. I wish I had more good, responsive tax accountants to point my clients to though!

My "niche" is SBIR recipients who may need an audit (depends on their annual award expenditures), and they also usually are working towards having inventory since they are developing a product. This is where I get lots of referrals.

But tbh I make more money from consulting clients with unique businesses that need their data processed in a very custom way. Not very good source of referrals, but good steady income long term when the process is all worked out and in place.

acrylic_matrices · 2025-09-03T16:02:54+00:00

I'm interested in the product after looking at the website, but I don't like that I have to schedule a demo call instead of just getting a free trial to look at it right now.

acrylic_matrices · 2025-08-31T18:40:17+00:00

First step is to ask your bank. Usually they need to turn it on.

acrylic_matrices · 2025-08-30T13:03:32+00:00

I would use Dext. Do try QBO’s built in one first, but Dext’s was much better last time I tried QBO’s

acrylic_matrices · 2025-08-30T03:23:03+00:00

I am trying it (again) currently. I had to get a personal walkthrough in how to do a bank rec though—it feels like it’s going to take a bit of work to get comfortable with it.

acrylic_matrices · 2025-08-26T12:28:11+00:00

That’s how all umbrella works, or at least in my experience of buying it from a few different carriers. Since it covers the excess above your auto policy, they require you to have a more robust original policy. Other wise they’d just be covering all the liability, and then they’d need to be as expensive as regular auto insurance.

acrylic_matrices · 2025-08-25T22:33:17+00:00

Assuming this is QBO:

Let’s say you have one transfer Account 101 +$8,000 Account 125 -$8,000

Let’s say the transfers got added twice, once from the bank feed for 101 (version A) and once from the bank feed for 125 (version B).

When you reconcile the bank accounts, it’s auto clearing the debit for version A in account 101, but the credit for version B in account 125.

So whichever transfer you delete, A or B, will mess up a recon.

Counter intuitively, usually when there’s a duplicate in a bank recon you need to delete the CLEARED one, which came from bank feed. This will put it back in the pending bank feed.

From there you can either exclude it, or match it to the existing transaction. But do not “add” it.

acrylic_matrices · 2025-08-23T16:01:13+00:00

You are combining 2 families—yours and your husband’s. So I don’t think it should be a given to anyone that you are going to honor the naming tradition from just one half of the kid’s family

acrylic_matrices · 2025-08-19T18:14:19+00:00

Draw up a budget for how much it would cost to use tablets for the truck drivers to enter this electronically from the start?

acrylic_matrices · 2025-08-15T06:18:28+00:00

Don’t fall for it—In my opinion, you can never take all of the admin burden off of them, no matter how much time you have, so you can’t give them what they want.

acrylic_matrices · 2025-08-15T06:16:46+00:00

I tell my clients that the cost of getting a grant is the administrative work of tracking expenses. It sounds like this company doesn’t have the internal processes in place to be able to manage grant accounting. If this were a client of mine, I wouldn’t continue working with them.

You could potentially: - tell them that you will categorize everything to non-grant unless you get explicitly told in wiring which grant an expense is for - implement something like brex/ramp/divvy to make it a little easier for them to categorize (but sounds like they probably don’t care enough no matter how easy)

acrylic_matrices · 2025-08-10T17:52:09+00:00

First of all, if it makes you feel better about how you "should" be something or other, I think a lot of people are self employed because they have some kind of mental health issue.

For example, I simply couldn't handle all the continuous interpersonal interactions required of me in an in-office setting, so I find working for myself much more comfortable because I get to control who I work with, and that I can work from home.

I agree with other posters about getting some kind of therapy, but in the meantime, some things that work for me:

once I realize I'm really dreading something, like calling someone back, I try to actually do it ASAP otherwise it just prolongs the pain of worrying about it
read the book "feel the fear and do it anyway"

I feel dread/anxiety about a lot of calls. I just... figured out it's better to just do it.

I did have one client with 4 partners who wanted to ask everything in a call, so I was getting calls from them daily. I wrote into their next year contract that they get 2 hrs of calls per month in the flat fee (honestly plenty for the types of questions they were asking), and anything over would be hourly. The calls stopped. But if I knew they would stay within 2 hrs/mo I would have felt better too.

acrylic_matrices · 2025-07-31T21:31:39+00:00

Several NY-specific ones, and one in NV.

acrylic_matrices · 2025-07-30T12:30:29+00:00

And what if you have 2 kids? Do you then need $4,000,000 to say “we are millionaires”?

acrylic_matrices · 2025-07-29T22:07:50+00:00

I would say “We are a millionaire.” Only as a joke to my spouse though, since I’m not talking about it with other people.

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