Good morning, eComm legend.

Ah, the sweet, sweet smell of side hustle cash. One minute, you're stacking wins—dropshipping, flipping collectibles, or selling those oddly specific T-shirts ("My cat is my therapist, and she charges in treats"). The next, the IRS slides in like an uninvited group project member, ready to "discuss contributions."

Yes, the rules are changing, and yes, more side gigs are now on the tax radar. But before you dramatically consider going full-cash-only like it’s 1997 at a flea market, take a breath. This isn’t a horror movie, just a new chapter in the long but inevitable saga of making money legally.

Stay ahead, stay sharp. Let’s dive in.

In today’s agenda:

1) IRS to side hustlers: We see you 👀💰

2) OpenAI just automated impulse buying.

3) Amazon’s Brand+: new AI-powered ads that (hopefully) don’t flop 😅

4) TikTok GMV Max: It’s not a new Pokémon, just a way to make more sales.

— Written by Alex Secanove

1) IRS to side hustlers: We see you 👀💰

Venmo used to be where you’d split tacos, now it’s part of a tax saga. Thanks to new IRS rules, third-party payment platforms like Stripe, PayPal, Venmo, and Cash App are sending out more 1099-Ks than ever. If your side hustle (or full hustle) runs through these apps, welcome to your new reality.

The new rules: The old “$20K and 200 transactions” rule is gone. In 2024, the threshold is $5,000. In 2025, it drops to $2,500. By 2026, if you make more than $600, the IRS wants a word. Selling vintage sneakers? Dropshipping artisanal dog treats? If you're getting paid digitally, expect that 1099-K.

What to do now:

• Separate accounts: Use one PayPal for business, another for sending your cousin gas money. No mix-ups.

• Track everything: Apps like QuickBooks, Xero, Wave, or even Google Sheets can save your tax season.

• Save receipts: That “business expense” won’t count if you don’t have proof.

• Check your 1099-K: If it’s wrong, dispute it ASAP. Platforms make mistakes.

The next steps: More small businesses will have to level up their bookkeeping, while larger ones likely won’t see much of an issue since they already have accounting systems in place (if not... please do... seriously... please... for real.... please). It’s either that or surprise tax bills. If you’ve been ignoring accounting, now’s the time to act. Or don’t, but future you (staring at an IRS notice) might have regrets.

Sources: irs.com, trolley.com

2) OpenAI just automated impulse buying.

OpenAI just launched Operator, an AI agent that does online shopping like your tech-savvy cousin who always finds the best deals before you even know they exist. It browses, clicks, fills out forms, and even price-comparisons across websites. In the coming years, your customers might never visit your store again. Fun.

Why this matters: Customers no longer manually scroll through pages of your products. They tell Operator what they want, and it does the shopping for them. If your product info isn’t clear, your pricing isn’t competitive, or your site isn’t AI-friendly, you might as well be selling flip phones in 2025 (nostalgic, but not profitable). For now, Operator works best with partner sites like eBay, Etsy, and Instacart, but it will eventually expand.

How to stay visible:

• SEO isn’t dead, but it’s changing. Operator scans sites like an over-caffeinated librarian, so clean product descriptions, structured data (schema markup), and fast load speeds are now life-or-death.

• Compete on clarity. Operator doesn’t have patience for vague product pages. Be precise, update stock info, and add clear return policies. It loves details.

• Optimize for AI navigation. If your checkout process is a maze, Operator might ghost you. Streamline it. (Also, Operator can’t enter payment details, so make it easy for users to finish the job.)

• Build brand loyalty now. If customers love you before AI takes over their shopping habits, they might tell Operator to favor your store.

Who wins and who panics: Big retailers with optimized sites will be fine. Smaller eComm shops will need to adapt, or they could be invisible. The real losers: ad platforms. If AI picks products, paid ads might have less influence, shifting marketing budgets toward SEO and direct relationships.

Sources: openai.com, wsj.com, digitalcommerce360.com

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3) Amazon’s Brand+: new AI-powered ads that (hopefully) don’t flop 😅

Amazon just dropped Brand+, an AI-driven ad tool that’s supposed to make video campaigns hit like a viral dance trend (but without the cringe). It's all about optimizing ads for Prime Video, Twitch, and even places like Fox Corporation and BuzzFeed. You, dear eComm owner, should care because it might finally make streaming ads not feel like setting money on fire.

Why you should care: Amazon’s got the data (a scary amount, honestly). Brand+ uses machine learning to sift through trillions of signals—what people buy, browse, and binge-watch—so your ads don’t just float in the void. Instead, they hit customers who actually care. In beta, some brands saw a 10% sales bump and 70% more website traffic. That’s not small potatoes.

How to actually use it:

• If you currently use Amazon DSP, integrate Brand+ with your existing Amazon Ads strategy (duh).

• Use first-party data (like customer lists) to help the AI target better.

• Track how Brand+ performs versus your usual ad spend. If ROAS moves up, you know it's working.

• Don’t rely just on AI—tweak creative and messaging based on campaign insights.

• Test across platforms. Brand+ isn’t just for Amazon—it plays nice with third-party publishers, too.

Where it fits in your strategy: This isn't a magic bullet, but it makes streaming ads actually measurable (which has been, let’s be honest, a disaster). Amazon says it’s for "full-funnel marketing,” meaning you can go from brand awareness to conversion without the usual “did my ad even do anything?” existential crisis. If you already run Meta or Google ads, consider testing Brand+ in parallel—Amazon’s targeting data is a whole different beast.

Final take: Amazon wants to eat more of the ad market, and this is its latest power move. If you’re tired of guessing whether video ads work, this might be your chance to actually track performance. Just don’t expect it to fix a bad product or bad creative—no AI is that good.

Sources: amazon.com, thekeyword.com

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* Executive Cheat Sheet

• 1099-K: A tax form issued by payment platforms (like PayPal or Venmo) to report business transactions, ensuring the IRS knows about your side hustle income.

• Schema Markup: A type of structured data added to websites to help search engines understand content better, improving SEO and visibility.

• ROAS (Return on Ad Spend): A metric used in digital marketing to measure how much revenue is earned for every dollar spent on advertising.

• GMV (Gross Merchandise Value): The total value of goods sold through an online platform, often used to gauge eComm success.