SMB Week 2026: What We Learned When AI Met the Network
When we extended National Small Business Week into our own celebration, we weren't sure what to expect. Two events. Two different lenses on the same question: what does AI actually mean for the small business owner who is busy running a business?
By the end of the week, the answer was clearer than we expected — and the rooms were fuller than we'd ever seen.
The week, by the numbers
Monday's kickoff with CEO Eric Groves — The Smart Business Era: How AI Helps Small Businesses Compete — drew 245 attendees, the largest Alignable Smart Connect ever.. Several more members tried to get in after we'd hit capacity. Friday's fireside chat with Lina Ochman, Head of SMB Growth at Anthropic (the team behind Claude), kept the momentum going.
Two different conversations. One consistent message.
What Eric heard from 30 years in the trenches
Eric opened Monday's session the way he opens most things — with the honest version. He's been a small business owner for most of his career, and for the first time in three decades, he's looking at a tool that has fundamentally changed how he works. Not "saved him a few clicks." Changed how he works.
That framing mattered, because the rest of his hour wasn't about hype. It was about specifics:
- AI is the unfair advantage SMBs have been waiting for. The big enterprises have had analysts, agencies, and ops teams for decades. AI is the first technology in a long time that gives a solo operator real leverage against that.
- Your network is still the asset. AI makes it manageable. The "50 Beats 500" pattern — that the most successful members on Alignable activate a focused set of relationships, not a sprawling one — held across 13 years of our data. AI doesn't replace those relationships. It makes the work of nurturing them sustainable.
- Start where the work is dreadful. Eric kept coming back to the same advice: pick the message you don't want to write, the follow-up you've been putting off, the profile copy you've been meaning to fix. That's where AI pays back fastest.
What Anthropic confirmed on Friday
Lina's session validated almost everything Eric said — and then added the operating system.
If you missed it, here's the short version of what she laid out:
You already have the #1 AI skill: management. If you can onboard an employee, you can work with AI. You direct it, you review the work, you own the result. The thing you do every day running your business is the thing that makes you good at this.
Treat AI like a brilliant new hire. It knows the world but nothing about your business on day one. Context is everything. Drop in past work as examples instead of trying to explain every rule. Show, don't just tell.
Learn the 4Ds: Delegation, Description, Discernment, Diligence. Decide what to hand off. Prompt clearly. Fact-check. Take accountability. That's the framework.
Start with one task — don't boil the ocean. Pick the email you're dreading or one repetitive workflow. Get it right. Then expand.
Push past the dip. Productivity isn't linear with transformational tech. Most owners quit too early. The payoff is on the other side of the learning curve.
Keep humans on the high-stakes calls. Use AI for back-office and repetitive work. Don't outsource the emotional moments, pricing decisions, hiring conversations, or anything that makes your business yours.
And the line that stuck with us most: "Wouldn't it be cool if…" Whenever you catch yourself doing something repetitive, bring it to AI and ask how it could take it off your plate. That's the entire mindset shift.
Where the two sessions landed in the same place
You don't need to be technical. You need to be clear about what you want done, willing to give context, willing to check the work, and patient enough to push past the awkward middle.
That's it. That's the playbook.
The members who got the most out of this week weren't the ones with the best tools. They were the ones who showed up, asked questions, and walked out with one workflow they were going to try this week. Not next quarter. This week.
Keep the momentum going
We're not done. The Smart Connect events that powered SMB Week with geo-based and incredible referral partner matches are running every week — and the easiest way to put any of this into practice is to show up to your next one. The relationships you build there are the ones AI helps you keep warm.
👉 Pick your next Smart Connect → Here.
See you in the room.
Comments (1-10)
Don, this recap is gold, and it validates something I've been saying to fellow small business owners for a while now: AI isn't coming for your business (or job, so don't panic), it's coming for your busywork.
What resonated most with me was Eric's advice to 'start where the work is dreadful.' That's not just practical, it's brilliant. Because that's exactly where most of us lose hours we'll never get back. The follow-up email we keep postponing. The bio we've been meaning to rewrite for two years. The proposal template we rebuild from scratch every single time. That's where AI earns its keep fastest.
Lina's framing of AI as a 'brilliant new hire' also hit home. And this falls right in place when I have a conversation with small business owners about adding AI to their business, but I call them an AI workforce (AI new hire). I tell them that the AI has to be trained like a new employee, so teach it everything it needs to know. It will never call in sick, request a day off, go on vacation, or have a slip-and-fall incident, get in a car accident, or find itself stuck in traffic, among other things. The best part? It works tirelessly for you 24/7/365.
I've found that the more you treat AI like a team member, giving it background, examples, and clear direction, the better the output. It's not magic. It's management. And as small business owners, we already know how to manage.
Here's what I'd add to the conversation: the biggest barrier for most SMB owners isn't the technology. It's permission. Permission to stop doing everything manually. Permission to let go of the idea that doing it yourself means doing it better. AI gives us that permission, backed by results.
The fact that both sessions were filled to capacity tells you everything. Small business owners are ready. They just needed someone to meet them where they are, and it sounds like Alignable did exactly that this week.
💬 For anyone who attended, what's the ONE workflow you're handing off to AI first? I'd love to hear what's at the top of your list!
This is such a valuable week for small business owners. One of the biggest takeaways for me:
AI doesn’t replace relationships — it helps us strengthen and sustain them.
The reminders to “start where the work is dreadful,” focus on meaningful connections over massive contact lists, and keep humans at the center of high-stakes conversations really stood out.
As a small business owner and community builder, I see AI as a powerful tool to help us work smarter so we can spend more time on what matters most — relationships, creativity, collaboration, and service.
Thank you to Eric Groves, Lina Ochman, Don Martelli, and the Alignable team for the practical and encouraging conversations around the future of SMB growth.
'Start where the work is dreadful' is legitimately great advice. Business owners almost always start with something exciting, which means complicated, which means a frustrating first experience. The boring follow-up email is the better rep. Low stakes, fast feedback, actual learning.
And context really does change everything. Owners who approach AI like a new hire they need to onboard get dramatically different results than those who expect it to read their mind. Where do you see the biggest gap between owners who build that habit and those who give up after one bad result?
Hi Don, thank you for putting this newsletter together. I really enjoyed the practical approach to AI and how you tied it back to real relationship building and networking. The message about using AI to support relationships instead of replace them really stood out to me. Great content and great timing for small business owners.
Your Brother,
Ralph Danna
This really captures where AI is becoming most valuable for small businesses, not replacing relationships, but helping business owners stay consistent, responsive, and organized at scale. The point about starting with the work you dread most is especially true. That’s usually where the fastest ROI shows up.
This is a really thoughtful recap. I like how it brings the focus back to practical use. The reminder that AI works best when paired with clear direction, context, and human judgment really stands out.
I attended the session with Lina from Anthropic and the whole discussion explained exactly why I founded YourGuide4 AI. I’m here ready to help small businesses go from inspiration from the webinar to actually using AI to propel their business just like high tech companies I’ve been working for throughout my career. Can’t wait to see the magic happen!
What strikes me is how specific Eric got about the problem. Thirty years in and this is the first tool that fundamentally changed how he works. Not saved him clicks. Changed the work itself. Then he pointed to the exact place most people should start: the message you don't want to write, the follow-up you've been putting off, the profile copy that's been sitting there.
I've built Nail Check, VeloxSync, Meraki Lingua. Every product came from watching where people actually get stuck versus where they think they should get unstuck. And that advice Eric gave matches what I've seen happen when someone finally picks one real task instead of trying to transform everything at once.
Don's recap added the framework that makes it work. The 4Ds. Treat AI like a brilliant new hire. Keep humans on the high-stakes calls. And the line that probably matters most: you already have the number one AI skill, which is management. You know how to direct someone, review the work, take accountability.
The thing about Eric's piece is that it's not selling the tool. It's reporting from someone who's been skeptical for a long time and finally found something that works. That's a different conversation than most people are having.
If I respond, that's the part I'd anchor into. Not the hype around AI. The honest observation that when you apply it to the work that's actually dreadful, something shifts.
Great summary. Great takeaways, even from this capsule. Are there recordings we can access? These presentations would be worth listening to...
I would love to share information the next time you meet about AI video mktg