Plus: Personalized pricing? | SMB tax prep tips
Are your finances in order? Tax season is right around the corner, so this week, we take a look at what every small business needs to know to file correctly while maximizing tax benefits and minimizing tax burdens. We also examine the best invoicing strategies to use to get paid quickly.
But first, check out this father-daughter team who run a small business while also sharing their travel and shopping adventures on Instagram.
Standing up. Target’s new CEO calls for de-escalation of ICE-related tension in Minneapolis.
Clear cut. Home Depot investors demand law enforcement transparency amid ICE raids.
White space. H&M bets on the Philippines for emerging retail opportunity.
High-low. High-income households are loving Walmart’s low-priced fashions.
Getting personal. Why personalized prices are the wave of the future.
What every small business should know about filing 2025 taxes
Nobody loves filing a tax return, but knowing how to file properly for your small business is critical. Also be on top of which small business deductions you can claim (home office, vehicle and travel expenses, equipment, office supplies and interest on business loans) and which small business credits (Work Opportunity Tax Credit, Small Business Health Care Tax Credit, Research and Development Tax Credit). Keep excellent records and pay your estimated quarterly taxes.
Why this matters: Filing your taxes incorrectly based on your business structure could cost you thousands of dollars, so taking the time to learn the rules and best practices will pay off now. (Forbes)
These invoicing strategies will help you get paid faster
It may sound simple: you invoice a vendor and they pay you. But according to Intuit QuickBooks’ 2025 Small Business Late Payment Report, 56% of small business are owed money for unpaid invoices which can impact them far more than bigger companies. Use these tactics to get paid faster: Start with a clear, detailed invoice; establish “ground rules,” i.e., penalties for late payment; avoid a net-30 payment schedule; use automation to send invoices and payment reminders.
Why this matters: The average past-due amount is $17,500 which is not small change for any small business. So make getting paid on time a priority in 2026. (CNBC)
Soaring health premiums force more SMBs to drop insurance coverage
U.S. retailers call for new credit card swipe fee laws
Why a physical store is more than a marketing strategy
These small business owners share how they grow with limited budgets
Bain’s retail sales outlook is surprisingly optimistic
Why AI can be good for local businesses
Central Massachusetts small business owner Lysa Miller, founder of website design and SEO agency Ladybugz Interactive, knows that a homepage filled with generic keyword-stuffed content is less effective than one that speaks directly to a local audience. AI-friendly websites mention service areas, local regulations, regional needs and seasonal information specific to your local region. Customer reviews, user engagement, accessibility and site performance all help AI assess whether a business is credible and additive to users.
“AI-powered search should improve results for local businesses demonstrating real expertise, audience messaging and community relevance. It favors websites that clearly explain who a business serves, what problems it solves and why it’s uniquely qualified to serve that customer." -Lysa Miller, founder of Ladybugz Interactive
Why this matters: In towns where businesses are built on strong local connections and expertise, adopting AI and voice search now will help your business gain momentum and thrive with its snowball effect. (Worcester Business Journal)
Watch out for these online ads pretending to be small businesses
Do you ever get sucked in by online ads with elaborate backstories and photos that explain a business owner’s journey and raison d’etre? While it may seem real because of all the detail, it can often be a red flag for scam site that’s looking to lure you into buying products that will never arrive. To combat these pitfalls, check for verifiable details like a mailing address, a working email, phone number or contact form. Check third-party reviews and look up the website’s domain address. Also, be aware of “sob stories” designed to illicit a sympathy purchase. Lastly, trust your gut. If it seems too good to be true, it probably is.
Why this matters: About 36% of American failed to receive refunds after purchasing an item that never arrived or turned out to be counterfeit, according to a Pew Research survey conducted in April 2025. Don’t be one of those people. (Toledo Blade)
Thanks for reading this week's edition!
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The SKUpe is curated and written by Marcy Medina and edited by Bianca Prieto.
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