Reporting LUMP SUMS on W2. 1099/ independent contractor

[Mr.Question]

What is the name of your state (only U.S. law)? New York

I work as a bike messenger for a W2 company in the city. I got hooked up with an off the books job that allowed me to make some cash before I begin my W2 job.
My OTB want to put me on the books so that he can now "write off the expense". So either I'm a 1099 or a W2. I don't want to be a 1099 because bottom line. I'll have to pay more taxes.
Like full cover my SS and all those other taxes that my employer would pay part of if it was a W2.

Now, an issue he brought up was like insuring himself/company but that is very expensive and I truly don't want to do that. While I understand what it is for. So if he did me like a 1099, it would absolve him of any liability and such. I get paid based on the amount of drops I do. So anywhere between 20-50 a day. Now if it were to be OTB on 1099 I'd have to record the drops and he'd pay me a check. I kinda didn't like that because of the whole tax thing. I rather be on a W2 where he'd pay part of the taxes and the others will be withheld.
But when I mentioned w2 he said something about hourly. I dont' want that because the nature of my day, sometimes I'm free to do other things before I finish his, such as hobby stuff, like taking pictures. I don't want to be timed. I am timed, in the sense that I have to do them before I go to my other job. But I dont want to have to REPORT a time.

So I was wondering couldn't I just record the gross pay and then he'll input it into some calculator that'll tell him how much to deduct and such, then give me the check like that. So its like a W2. I don't have to worry about doing quarterly payments and all that junk with the 1099.

There was a company that "fired all their bikers" and told them they'll only hire walkers. It was too expensive to insure the bikers. He told the people to sign something I guess, which is like a contract or something saying that they won't use a bike to delivery and only walk. I was wondering can I come up with something similar so that I can absolve him of any liability such as workers comp, or insurance. Like, I'll do my delivery using mass transit. I'll still have my bike though because of my latter W2 job in the day.

 

[cbg]

Sounds like you want to have a piece of all the pies at once and you don't really care if it's legal for you to do so.

Off the books is illegal, period.

It is always legal for an employer to consider you an employee and give you a W2. You have to meet IRS qualifications to be considered an IC and get a 1099.

It may be that you do qualify to be an IC. However, if you do, then you get treated as an IC. If you want the benefits of being an employee, then you have to be an employee.

You don't get to have the freedoms of being an IC but be treated as an employee when it's convenient for you. Either he does all your tax deductions and gives you a W-2, or you pay your own deductions and get a 1099.

 

[Mr.Question]

Sounds like you want to have a piece of all the pies at once and you don't really care if it's legal for you to do so.

Off the books is illegal, period.

It is always legal for an employer to consider you an employee and give you a W2. You have to meet IRS qualifications to be considered an IC and get a 1099.

It may be that you do qualify to be an IC. However, if you do, then you get treated as an IC. If you want the benefits of being an employee, then you have to be an employee.

You don't get to have the freedoms of being an IC but be treated as an employee when it's convenient for you. Either he does all your tax deductions and gives you a W-2, or you pay your own deductions and get a 1099.

But you haven't answered. Are you implying that hourly is a stipulation of being a w2? I know exactly what of the books is, that is why I have no issue with being in the books when requested But you haven't addressed my concern with w2. There's literally won't be any change of duty either way. I'll still deliver, uniform is not required etc.
Will there have to be any additional cost to make me a w2. I guess, aside from paying half the tax, that's a cost.

I'm not even too sure if him paying half the cost is an issue. It was more liability.

 

[Zigner]

But you haven't answered. Are you implying that hourly is a stipulation of being a w2? I know exactly what of the books is, that is why I have no issue with being in the books when requested But you haven't addressed my concern with w2. There's literally won't be any change of duty either way. I'll still deliver, uniform is not required etc.
Will there have to be any additional cost to make me a w2. I guess, aside from paying half the tax, that's a cost.

I'm not even too sure if him paying half the cost is an issue. It was more liability.

Frankly, it sounds like you could be properly classified as an independent contractor. If you keep up this boat rocking, you may find your tax situation even easier to handle because you won't have to worry about making any money from the company.

 

[cbg]

There is a list of approximately 20 criteria to be an IC. While there is no single element that "proves" employee or employee status, it goes by the preponderance of evidence. Unless you can show that the majority of the criteria are all true, you are an employee by default. Remember - employee is the default. You have to be able to prove to the IRS that you are an IC.

One of the those criteria is schedule. You aren't being very clear when you talk about "hourly" but non-exempt employees, which is what you will be if you are an employee, are paid on an hourly basis most of the time, and the per-hour wage is what the IRS and DOL use to determine correct pay AND correct taxes. So while an employer *could* if they chose to, allow you to pick your own schedule, you would still need to report your time in hours. That is a given. No exceptions, no loopholes, no choices. Nor is the employer required by any stretch of the imagination to allow you to set your own schedule. The law will back him 100% if he insists on scheduling you.

You need to get your head around the fact that you are not in charge of this.

 

[Mr.Question]

There is a list of approximately 20 criteria to be an IC. While there is no single element that "proves" employee or employee status, it goes by the preponderance of evidence. Unless you can show that the majority of the criteria are all true, you are an employee by default. Remember - employee is the default. You have to be able to prove to the IRS that you are an IC.

One of the those criteria is schedule. You aren't being very clear when you talk about "hourly" but non-exempt employees, which is what you will be if you are an employee, are paid on an hourly basis most of the time, and the per-hour wage is what the IRS and DOL use to determine correct pay AND correct taxes. So while an employer *could* if they chose to, allow you to pick your own schedule, you would still need to report your time in hours. That is a given. No exceptions, no loopholes, no choices. Nor is the employer required by any stretch of the imagination to allow you to set your own schedule. The law will back him 100% if he insists on scheduling you.

You need to get your head around the fact that you are not in charge of this.

To better explain what I do.
Every week prior or day before, we set up a time for me to come in, based on what time I start my primary job.
I go to his place of work, pick up X amount of bags and I am paid varying amounts depending on delivery zones. He shows to me what he has available to deliver and I choose if I can do all or part of it. I then leave, head to the drop offs, gather proof of delivery and proceed to the next one until I am done. Now sometimes I would attempt a delivery and the person isn't there so I'd hold on to it and possible bring it BACK or make a second attempt after I finish my primary JOB.

That what I do.

**EDIT ^^^ after I wrote the passage bellow
_____

In regards to whether I am in charge of this, I am being asked if I want to be reported as a employee or a independent contract. So in some respect its something I have to choose. While under LAW if am Ian employee he do what a boss can do with an employee but doing anything different than what WE already establish wouldn't be beneficial.

With regards to my schedule, it really is unclear because there is no SCHEDULE, per se. But he expects me to be at his WORK at a certain time so that I have enough time to complete his drop offs before I head into my other job. I indirectly have a schedule in order to do his deliveries in time. So usually everyday I'd head to his place around X o'clock and pick up the things and delivery usually 3 hours roughly. and Other days it would X+2 o'clock and delivery sometimes one hour sometimes 5 hours depending on the amount of deliveries. (and whether if I am working my other job). However I get paid per job, not per hour. So I could be paid 40 for 3 hours one day. and then 31 for 4 hours. The time to delivery doesn't directly affect what I receive. It generally wouldn't make sense for him to FORCE a schedule on me other more than what we have going on right now as it works best for both of us. I give him a layout of my schedule from my other job and we work around that each week.
Another instance of maybe a cloudy area around scheduling is that say I made an attempt to deliver but the person wasn't there. So what I would do is after I finish my primary job ,~~5 hours later, I'd go and attempt again before I head home.

I'm trying to see if I am classified as an employee, wouldn't I just tally up how much hours I spent delivering and how much he paid me and report it to him so he could input it in some calculator that'll tell him what to pay me this week. Isn't that possible. My per hour would change per day, so I'm trying to see is that still employee and how would I go about it.

Look I'm not trying to pull a fast one. We both mutually benefit from this partnership, however I totally understand his reason to need to write this off as an expense whether employee or IC.