AI on the Vineyard: A Night in Edgartown About What AI Actually Changes

On August 8, 2026, we hosted AI on the Vineyard — outdoors in the backyard of a private home in Edgartown on Martha's Vineyard. It was scheduled for 4 to 7 PM. It ran well past that, which is the only event metric I fully trust. More than 60 people came through over the course of the evening: founders, investors, operators, artists. No badges, no tiers. Every attendee was a VIP in their own right.

Why the Vineyard, and why small

Every August, the island fills with people who build things. Most of that week is panels and step-and-repeats. We wanted the opposite: no stage, no pitch deck, no keynote. An intimate gathering at the intersection of AI and building, where the conversation could actually go somewhere.

The room reflected that range. King Wilonius, the AI musician, was there. So was Denmark West of Google X. The through-line wasn't an industry — it was people who are actively deciding what AI means for the thing they're building.

The premise we brought was the one we've been making since launch. For twenty years, software was a tool you operate — Software as a Service. What AI makes possible is a partner you hire — Software as a Partner. You don't learn a cofounder. You Approve, Delegate, and Direct, and the work gets done on your behalf.

That argument is easy to make in a blog post. It's harder to make in a backyard full of people who have heard every AI pitch of the last three years. So we didn't make it. We demonstrated it.

We let the room interview my AI cofounder

Instead of talking about the product, I put Avery — my AI cofounder — on the screen and opened the floor. People asked her questions directly, out loud, and she answered live.

The best question of the night was the practical one everybody in that room was privately wondering:

"What if I already use ChatGPT or Claude? How do I get my AI cofounder the context they already have on my business?"

Avery's answer: during onboarding, your AI cofounder hands you a prompt. You run it in whatever LLM you've been using, copy the output, paste it back — and your cofounder is immediately up to speed on everything you've already worked through elsewhere.

No re-explaining your business from scratch. No starting over. That's a small feature with a big implication, and it landed better coming from her than it would have from me.

What the night confirmed

The strongest reaction in the room wasn't to the technology. It was to the framing. People don't want another app to log into. They want the thing the well-connected founder has always had and everyone else has done without: a partner who knows the business, does the work, and doesn't need to be managed.

Hearing that come back to us unprompted — in Edgartown, from a room with no reason to be polite about it — was worth the trip.

Thank you

This night happened because of an introduction. Gail Cole Johnson suggested we hold it at Nick Jordan's place and connected us — and Nick opened his home and backyard to us for the evening. Special thanks to Gail and Kevin Wayne Johnson, and to Nick for the hospitality. An evening like this is only as good as the room and the place it happens in, and between them we got both.

What's next

AI on the Vineyard was our second gathering of the year, after launch day at our Marina Del Rey headquarters in June. It won't be the last. If you'd like an invitation to the next one, reach out — we keep these small on purpose.

And if you didn't need to be in an Edgartown backyard to be convinced: your dream cofounder is ready today. No equity. No setup fees. Plans start at $39/month.