So, does anyone actually have any insight into how things work when you're dealing with betting sites or casinos, specifically in cases where funds have been sitting in a checking account for years?
Nathan Morris3 said:I don't really see an issue there, honestly. You can clearly see the payout in one bank and the deposit in the other. Maybe a problem could arise if you're carrying cash from a foreign account and trying to deposit it into a US bank. You'd probably need to keep all those receipts handy.
And regarding the gambling stuff, if you don't get a receipt or a statement, I guess that would look like some shady, illegal business.
Have any of you ever actually placed bets? If so, have you ever walked away with a win? I’m talking about the old-school way—walking into a physical sportsbook or using one of those machines at a local pub. Or maybe you've been to a casino and actually hit a jackpot? Here is my experience: over the last nine years (though I haven't been active for the last year or two, so things might have changed), I have never once received an official payout slip. All I could ever do was make a photocopy of the winning ticket and keep that for myself, since they always insist on keeping the original. Honestly, I never even bothered to do that, especially after reading on a forum how someone got absolutely hounded by authorities just for trying to prove their winnings with a photo of a ticket. How are you even supposed to prove to the IRS where all that accumulated cash came from, especially when I almost always transferred it straight to my checking account, with a chunk being funneled immediately back into the next bet?
ironcyclist58 said:It might be "anonymous" in the sense that they don't have your ID on file, but surely you get some kind of receipt or payout slip? (I wouldn't know, I don't mess with sportsbooks or casinos)
I’ve actually never received a physical receipt from any sportsbook. Usually, it's just this whole process where you show your winning ticket at the window, grab your cash, and they just hang onto the slip themselves. Is that just how it works everywhere?
I mean, there’s gotta be a legitimate way to justify income to the IRS while still keeping things relatively anonymous when you actually collect the cash, right? Take sports betting, for example. I’ve been betting quite a bit myself over the last eight years, and my payouts have always been handled in cash, which keeps things private. And honestly, who’s stopping me from just depositing that cash into my checking account? Even my biggest wins—we’re talking around $5000—were all settled in cash. Since the bookies handle the taxes on winnings at the point of payout, what's the actual issue? How are you supposed to explain to the tax man that it’s gambling winnings from a sportsbook, or maybe some perfectly legal action at a casino? Or even those slot machines? As far as I know, most of that stays pretty anonymous still.
Thanks so much! I just have one more quick question🙂. Is there any kind of deadline I should be worried about? For instance, I had some equipment delivered about two weeks ago, but I don’t plan on actually launching my small business for another seven or maybe nine months at most (once I finally wrap up my degree😁). Sorry for being such a pest😢—this is all pretty new territory for me .
So, here’s what I’ve gathered so far: I really need to hang onto all my receipts and those specific documents proving I paid sales tax at customs. Once I officially launch my small business, if I submit those invoices and confirmations, will they be treated as deductible business expenses?
brisktinker15 said:Since you’re mostly just freelancing for regular folks, there’s zero reason to deal with the headache of collecting sales tax right out of the gate. Just stick to standard income tax for now, and once you start pulling in serious bank—which, let’s be real, isn't happening overnight with this kind of gig—you can always make the jump to a sales tax registration later. Regarding that car, since it’s technically in your dad's name, I’m not sure if you can even list it as a business asset, but honestly, it wouldn't matter much since you aren't collecting sales tax anyway; just make sure you track your mileage because those deductions are pure gold. Keeping the books is actually pretty painless if you stay out of the sales tax system, so if you have a buddy who actually knows his way around an Excel sheet, you could probably DIY it—that’s basically how I handle my own stuff. Just don't get lazy; stay on top of whatever new IRS updates roll out so you don't get blindsided. Expect your payroll taxes and social security hits to land around $567/month. Don't let those pile up; seriously, it's better to take a smaller paycheck than to end up in the crosshairs of the IRS. Basically, any expense you rack up to keep the business running counts as a deduction—so we're talking mileage, software subscriptions, gear, office supplies, your cell phone bill, all that jazz. Just remember, you need to make sure every single receipt has your name and Social Security number on it so the accountants can actually use them.
Good luck!
Does this apply to small businesses that stay out of the sales tax system, or is it strictly for those who opt in? I’m actually planning to launch my own graphic design studio in a few months, and I’ve already started picking up some equipment. My plan is to stay exempt from sales tax during the first year, so I have to wonder—should I still be keeping all these receipts? I actually bought some machinery overseas, and everything was cleared through customs properly, but I paid for the stands using my credit card. Will a standard transaction record count as proof if I need it later?