🎯 AI, SMBs & Retirement—Plus: AI-generated ads, logo tattoos & the great chamber walkout

Welcome back to the AI for Small Business newsletter!

This week’s roundup is all about decisions—big and small. Should you ditch your local chamber of commerce? What’s your retirement endgame as a small business owner? Is it finally time to bring AI into your marketing workflow, or maybe just hire a designer on Fiverr for that logo you’ve been putting off? Meanwhile, tariffs are back in the headlines (and at the cash register), sparking fresh anxiety about costs and consumer behavior. Mix in some sharp takes on counterfeits, MBAs, and mental health, and you’ve got a pretty vivid snapshot of the small biz headspace right now – so let’s jump in.

📉 Memberships, Motives, and Endgames

🔗 Has anyone left their local chamber of commerce?
Many small business owners are questioning the value of chamber memberships, especially when networking ROI seems minimal. This thread is a raw look at what owners feel they do and don’t get from these orgs—and how they’re reallocating time and money. Do you belong to a CoC or similar organization? We’d love to know what you think.

🔗 What’s your endgame?
Exit, lifestyle, legacy—every business has a different “why.” This discussion is a refreshingly candid look at what motivates owners and when it's time to admit you're chasing the wrong goal. Our survey of 1600+ small business owners says many of them are preparing to exit their business, either by selling or often by having their children take over. What’s your plan?

🧠 Tariffs, MBAs, and the Cost of Doing Business

🔗 Baby store prices spike due to tariffs
From strollers to car seats, prices are rising fast—again. Tariffs are making life tougher for retail owners and consumers alike, with ripple effects likely to hit Main Street hard. As parents we feel this pain (although I imagine if you’re buying UPPABaby products the extra cost might not be a huge issue).

🔗 We can’t survive the ‘short-term pain’
This interview highlights how fragile the margin for error really is for many small business owners. “Short-term pain” isn’t just an inconvenience—it’s an existential threat. Keeping cash on hand is hard, and it’s worth thinking about what your backup sources of capital are, and how you can do some financial planning to mitigate short term pain.

🔗 Why an MBA might be a mistake for most small business owners
It’s a bold take: MBAs are often too theoretical, too corporate, and too expensive for entrepreneurs. Instead, the author argues, learn by doing—or pay a fraction of the cost to learn from those already in the trenches. I [Adam] have a business degree and have only found value in a few of the classes (accounting & finance, the classes that are most grounded in hard research and mathematics) useful; when I started my first company I had no idea what I was doing and the degree didn’t tell me. There’s simply no substitute for experience.

🧩 Practical Questions and the Hidden Costs of Scale

🔗 How do you deal with counterfeits?
Whether you’re on Etsy or Amazon, counterfeiters are a real threat to product integrity and brand trust. This thread shares battle stories—and some solid prevention tactics—from fellow founders.

🔗 What’s the biggest thing holding your business back?
This article explores what’s really in the way: burnout, lack of focus, poor systems—and sometimes, our own fear of success. While we agree in general with the article, and the answer isn’t always “money”, the answer often is… money.

🎨 Branding, AI Marketing, and Mental Wellness

🔗 L’Oréal & Google team up on AI content tools
Big brands are automating marketing at scale with AI-generated creatives. This is a peek into the future for smaller teams—faster content, smarter targeting, and more room to focus on strategy.

🔗 Logo tip: Consider hiring a tattoo artist
The idea that a tattoo artist can double as a logo designer makes sense when you think about it—tattoo artists are frequently called on to come up with a memorable design on short notice with little clear specification, pretty much exactly what you’re asking designers to do for logos. That said I’m not sure how well the request will go over with the artist as some may take offense to even being asked. Of course, you can always get the tattoo and later use it as a logo.

🔗 OpenAI & mental health

ChatGPT is showing up in mental health support contexts—which is exciting, but also complicated. This is a great read on the line between helpful and risky when AI starts playing therapist.

✨ Your Turn
We want to hear from you:
Are tariffs changing your pricing strategy? Did you drop out of your chamber? Using AI in your marketing?

Hit reply and tell us what’s working—and what’s not—in your small business right now.

Til next time,
—The MarketStreet Team