Trent Gillespie
August 19, 2026
On Saturday, a CEO told an AI app I built that it was just a “palm reader.”
That was probably the funniest feedback I received during four days at ASAE’s Annual Summit in Indianapolis.
It also captured the question underneath almost every conversation I had that week:
Can any of us really see where AI is taking our industries? And can we do something to improve the outcome?
That morning, I gave 100 industry leaders access to an AI I built and facilitated a three-hour workshop around a fairly ambitious challenge: use AI to create a plan for improving your entire industry.
There was one important constraint.
The plan also had to create human jobs.
I had never done anything like it before. One hundred leaders. One hundred industries. All working at the same time, through a process facilitated by an AI I had built.
I knew the technology worked. I didn’t know how well it would hold together in a room like that.
It did.
Across the group, participants reported being 55% more confident about their industries’ future with AI. Thirty-three percent said the plans they developed could help create jobs, potentially up to 250,000 jobs if those plans were fully executed, according to Claude.
The rest said they needed more time to study what they had created.
That makes sense. You do not design an entire industry’s future, on your own, in three hours.
But you can take a meaningful first step.
And I think that matters.
The next day, I started handing out fortune cookies.
A lot of them.
I had found FancyFortuneCookies.com, a local manufacturer in Indianapolis willing to make me 775 custom fortune cookies. Each containing an AI skill designed to help association leaders better understand their members.
They made five flavors: vanilla, strawberry, blueberry, chocolate, and green apple.
At lunch, I went row by row across the exhibit floor, table by table, handing them out.
That may have been my favorite part of the event.
Most people had no idea what an AI skill is. But they were willing to try a flavored fortune cookie.
Chocolate was the favorite.
And the cookies gave me an excuse to have hundreds of conversations.
I met people from what seemed like every corner of the economy, from ice cream stores to concrete manufacturers.
Different industries. Different members. Different business models.
The same question kept coming up:
What do we do about AI?
It was also the number one question during the CEO AMA.
That stuck with me.
I heard the same concern again during my closing talk, “AI in Your Hands.”
I shared what is becoming possible with Cowork and showed the audience how to build AI agent skills: reusable instructions that allow AI to carry out valuable work again and again.
Then I asked how many people had actually used it.
About four hands went up in a room of roughly 200 people.
That gap is important.
The technology is moving much faster than most leaders have time to absorb it. They are being asked to make decisions about capabilities they have barely had a chance to experience.
So I gave the audience a roadmap they could personalize during the session and continue updating as the technology changes.
Somewhere in the middle of the week, I also got to take a lap around the Indianapolis Motor Speedway.
Fast, loud, and a lot of fun.
Given the week we were having, it felt appropriate.
All of this is part of why I’m launching Leader Lab this Friday.
I don’t want to create another place where I simply tell leaders what is happening in AI.
I want us to build a place where we figure out what to do about it together.
I’ll bring my latest research, practical methods, office hours, new tools, and the people I trust. Members will bring the problems, questions, and opportunities they are seeing inside their organizations and industries.
Together, we’ll decide what deserves attention. We’ll build things, test them, learn what works, and keep improving.
That work will also help determine where we invent at Stellis, so the people in Leader Lab can influence what gets built and get first access to what comes next.
We’re starting small.
And we’ll build it around the people who show up.
After four days in Indianapolis, I came away more convinced of something I’ve believed for a while:
The future feels less frightening when you have a hand in building it.
Join us Friday at noon Pacific and help us decide what we should solve first.
You may have heard about this one already.
Anthropic is adding an invisible watermark to text written by future Claude models. I don’t think it’s something to be overly worried about. Google already uses a similar system with Gemini, and Anthropic says other major AI providers are implementing watermarking as part of new EU AI transparency requirements.
Here’s roughly how it works.
AI generates text one word, or more precisely one token, at a time. At many points, several possible next words would work.
Maybe it could choose “significant.” Maybe “substantial” instead.
The watermark slightly influences those choices. Across enough words, the selections form a statistical pattern that can later indicate that Claude was probably involved in writing the text.
Nothing visible is added to the document. There are no hidden characters. The watermark also does not identify the person, organization, or conversation behind the writing.
The more Claude-generated text there is, the easier the pattern is to detect. Light editing probably will not remove it completely. A substantial rewrite can weaken or eliminate it.
So, for now, I wouldn’t change anything you’re doing.
Just be aware of the direction this is heading.
More AI-generated content, from text to images, audio, and video, will increasingly carry some form of watermark or provenance signal. Google’s SynthID already spans those formats.
For most of us, there’s no action needed yet.
It’s just another piece of the AI infrastructure worth understanding.
Hope to see you there!
Trent Gillespie is CEO of Stellis AI and a keynote speaker helping business leaders understand and operationalize AI in their companies. He spent almost nine years leading global innovation efforts at Amazon before leaving to help other companies build the capabilities they need to compete. Book Trent to speak to your group or book a call to discuss using AI within your business.
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