Cyber Monday is a goldmine for savvy shoppers, and a launchpad for thousands of side hustles. From flipping discounted electronics to reselling limited-edition sneakers, many people use the day’s deals to stock up and sell for profit. But what starts as a smart move can quickly spiral into a logistical headache if you’re not careful. Here’s how to make the best decisions on Cyber Monday for your side business.
Avoiding Costly Mistakes on Cyber Monday
To find the best deals for reselling on Cyber Monday, you have to be smart from the beginning. Set up shopping alerts to score the best items. But, you have to be aware that making a profit requires you to be picky when selecting inventory. Not all deals are resellable. You’ll have to track your cost of goods, look up price comparisons on resale marketplaces, and calculate margins to decide if sales are worth flipping. Tools like Terapeak can help you make informed decisions. If you overbuy, you could be left with a ton of stale inventory.
Often, liquidation companies run sales on Cyber Monday. But that doesn’t mean that boxes or pallets of inventory are worth buying. Always look up reviews on the company you are interested in buying from. Many companies sell goods that are heavily damaged, not on trend, or don’t hold value. You don’t want to be saddled with inventory that you have to take a loss on. Do your homework and don’t buy just because it’s a good deal.
If you are buying from traditional retailers with the intent to resell, you also have to consider that your consumer may be aware of these deals. Shoppers are more savvy than ever. If you try to resell items for a higher price, the market may not support it. Make sure to purchase items that are scarce and desirable for the best profit. You’ll want to consider things like sell-through rate and brand reputation before making purchases.
Platform Considerations
E-commerce platforms like eBay, Etsy, and Facebook Marketplace are under pressure to enforce stricter seller policies. That means verifying identities, tracking inventory, and flagging suspicious activity. If you’re buying large quantities of items on Cyber Monday and immediately listing them for sale, algorithms may tag your account as a commercial seller. Make sure that you have the proper documentation to resell certain brands, or your account could get flagged. In addition, always make sure that your items are authentic. If you list counterfeit goods that you bought on sale, your accounts could get suspended or you could get banned.
The Tax Trap You Didn’t See Coming
Most people use the same PayPal, Venmo, or Cash App account for everything: splitting dinner, buying gifts, and collecting payments from buyers. But when Cyber Monday purchases intended for resale flow through the same account as personal transactions, it creates confusion. Always keep your business purchases separate.
The IRS doesn’t care whether you call it a hobby or a hustle. If you’re making money, it’s taxable. Many Cyber Monday resellers forget to track their expenses, keep receipts, or report profits. But once a 1099-K is issued, the IRS expects a matching income report on your tax return. If you don’t file correctly, you could face penalties, interest, or an audit. And if you’re using personal accounts for business income, you may lose access to deductions that could lower your tax bill.
How to Protect Your Hustle
If you plan to resell Cyber Monday purchases, treat it like a business from day one. Use a separate bank account or payment platform for all transactions. Track your purchases, sales, and shipping costs. Save receipts and document buyer communications. Consider using accounting software or a simple spreadsheet to stay organized. And most importantly, understand your tax obligations.
The Bottom Line: Smart Hustles Need Smart Systems
Cyber Monday can be a launchpad for profit, but only if you treat your hustle like a business. Mixing personal and commercial activity may seem harmless, but it can lead to serious consequences. With a little planning and discipline, you can flip deals without flipping out.
If you’ve turned Cyber Monday into a side hustle, leave a comment. Your tips could help others avoid costly mistakes.
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Teri Monroe started her career in communications working for local government and nonprofits. Today, she is a freelance finance and lifestyle writer and small business owner. In her spare time, she loves golfing with her husband, taking her dog Milo on long walks, and playing pickleball with friends.
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