Following the Breadcrumbs
Day 11 of building in public.
Today felt like the kind of day I left for. Not easy exactly. but alive.
Breakfast at 8:30 with someone running entrepreneurship initiatives at the Indiana Department of Commerce. We had an interesting conversation about how they could use AI tooling more effectively to drive stronger citizen engagement.
Fun one.
Then I had a speaker discovery call teed up by a VC as I continue to pursue the Milkcrate concept.
The original hypothesis was pretty simple: experts need an all-in-one tool to run their business. I think that hypothesis has mostly been disproven.
After enough conversations with speakers, coaches, consultants, and experts, I don’t think the core pain is “too many tools.” The pain is growth. The pain is pipeline. The pain is turning expertise into a durable business.
So I still believe there is a platform play for non-physical SMB companies. I just think it probably starts somewhere more obvious.
Websites. The website is the front door of the business. It is where positioning lives, where the offer shows up, where trust is built or lost, and where many of these businesses still feel way behind.
So, back to the drawing board. But not off the board.
I also had a follow-on call for another fractional opportunity and I’m starting to get the sales process down a little better.
The thing I’m building for this work is what I’m calling a “pipeline catalyst.” Basically, it ingests a bunch of pipeline and customer data, applies my interpretation of the gaps, and spits out a 4–5 recommendation proposal.
I’m building it as a Claude skill, which I didn’t even know existed until a couple of weeks ago. But it has basically become a way to create my own little internal products for recurring tasks and analysis.
The best part is that I can train it to analyze data more like I would. Not perfectly, but close enough that I can keep going back and forth with it until the output gets to a place I actually like.
I ship my first one to a client this week.
Then I went onsite for a consulting proposal I’m working on, which is tied to the same work above. I find it fascinating to dig deep into GTM data and try to understand which levers could actually drive growth.
Right now, I’m doing a lot of it for free. Probably 10+ hours for this one client. And the strange part is, I genuinely enjoy it.
I enjoy finding the story inside the data. I enjoy looking at the pipeline and trying to figure out what is real, what is fake, what is stuck, what is underpriced, what is under-resourced, and what one or two moves could change the trajectory.
I’m trying to learn to trust that.
I ended the day going back and forth with Claude on the pipeline catalyst skill.
It was frustrating. The outputs are not magic. There is still a lot of shaping, pushing, and correcting.But they are pretty good. And it saves me a ton of time.So it feels worth it.
Days like today energize me because of the variety. Seven meetings across state government, AI consulting, speaker businesses, SaaS GTM, and fractional work.
That is fun for me. It also fries my brain. So I’m trying to stay in the discomfort and not jump too quickly to anything. There is a version of me that wants to turn every interesting conversation into a job offer, but I’m doing my best to not give in.
I think the job right now is to keep paying attention.
What gives me energy? What are people actually willing to pay for? Where do I have a real edge? Where am I forcing a thesis because I want the story to be clean?
No big lesson today.
Just a full day, a fried brain, and a few more breadcrumbs.
-Foley