What To Know Before You Start

They're Going To Ask For Personal Information

Online casinos collect a lot of personal information to comply with regulations intended to prevent money laundering and other unlawful activities. (Speculation, but because they are so tightly regulated, your data may actually be safer with some of them than with your average social media company.) You should be aware that many of these sites will request a photo of your ID, and some regularly ask for a selfie to confirm a redemption or purchase. Every site will request your name, address, and email. Most ask for a phone number. Some ask for bank statements to verify your receiving account, and a few will request a utility bill to confirm your address. A small number request a Social Security Number in order to issue a tax form. Some use third-party services to connect to your bank accounts, and these third-party services may collect some personal information, as well.

That's a lot of personal information, and it may break this hustle for some of you. Regulated or not, your personal data is now on somebody's server, and data breaches happen all the time.

What You Can Do About It

Some of this is easy. Open a new email address you'll use for nothing else, and consider a secondary bank account just for redemptions. (Plenty of online banks offer free checking accounts and even a nice sign-up bonus. Side note: churning bank account bonuses is another very easy side hustle.)

A secondary phone number can be worth it. I personally use a free Google Voice number on a lot of websites. Just know that some sites detect VOIP numbers and don't accept them.

Your ID, Social Security number, name and address are a different matter. There is very little you can do there. Your only lever is which sites you hand them to.

And finally: if you ever buy coins, I highly recommend a credit card. If you ever have an account closed with a balance, a chargeback may be the only way to get your money back. Plus, this is a great way to earn some extra cash back. (More on that in Freebies And Credit Cards.)

What You Need To Get Started

A laptop (recommended). A phone is usable, and many people start on one, but a laptop is faster once more than a few sites are in rotation, as you'll need to click through a lot of browser tabs.

A password manager. Your browser's built-in password manager is fine, and Bitwarden is a free option that works well. It will make your life so much easier because many casinos make you log into a new session every single time you visit. When you sign up, a password manager can generate a safe, unique password, and save it for you. Set it up to pre-fill your credentials when you open the login page. You'll thank me later.

A system for tracking balances. You don't want to wing this with a few dozen casinos. Also, you'll need exact records for tax time. A spreadsheet can work well to track your balances at first, but you may find soon that it requires a lot of maintenance. SweepsOwl was built to handle that for you: it automatically updates your ledger, lets you know when your bonuses are ready, and warns you before your coins expire (which is a thing at a few casinos).

Optional: a single bookmarks folder for all sites speeds up daily logins (or use SweepsOwl's Daily Run feature). A personal finance tracker such as Monarch or Quicken Simplifi can confirm that redemptions arrive in the linked bank account.

A Warning On Taxes: Keep Thorough Records

The following isn't tax advice, but has been cross-checked against the statements of a specialized CPA. We recommend taking your questions to a qualified tax professional.

What's uncontroversial and well-known: gambling winnings are generally reportable income in the United States, and some sites issue a tax form regardless of whether one is expected. So definitely keep clean records of your winnings and losses for tax season.

But unfortunately, this hustle falls into a legal grey area. The IRS has not issued clear guidance for this specific activity, and the general rule for gambling income is strict: a casual gambler owes tax on total winnings with no offset for amounts wagered, so a person who gambles $200 at a casino and walks out with $100 will owe tax on the full amount of $100, aka their "winnings." In some cases, losses can be claimed if you itemize your deductions.

A crucial question is whether what you're doing counts as a hobby, or actually constitutes a business activity. The IRS treats an activity as a business when it is carried out regularly and with a genuine intention of making a profit. A business can deduct expenses, with taxes due only on profits.

My advice for tax season: bring the following questions, along with complete records, to a qualified tax professional:

1. Given how regularly I do this, and how I track it, does this qualify as a hobby or a business for tax purposes?
2. If it is a business, can coin purchases be treated as a cost against the income?
3. Are free daily bonuses reportable in the same way as redemptions from purchased coins?
4. What records should I provide, and in what format?

Whatever the answers turn out to be, by now I think you recognize how important it is to keep good records. SweepsOwl is a great place to keep exact records of your income, winnings and losses, and expenses.