Pilot

The portfolio right now: Archway does advisory work, Dropsignal is a live subscription product with zero customers, and Tasuki is still pre-launch. This week was about getting the foundation right before anyone sees it.

The inventory problem

Dropsignal had a credibility gap. The marketing site said "thousands of digital screens" because we didn't actually know how many screens were in each market. That's the kind of thing you can get away with when nobody's looking, but we were about to start reaching out to real podcasters. "Thousands" wasn't going to cut it.

So we built a pipeline into Vistar's DSP. That's the demand-side platform that connects to screen inventory across the country. Billboards, bar TVs, gym displays, gas station screens, office lobbies. Three tools, one afternoon, and we had real numbers for all 50 US markets. New York: 26,914 screens. Nashville: 1,220. The placeholder copy was dead.

Small bit of irony here. Back at Clear Channel Outdoor, I helped make our inventory available on Vistar's SSP. One of the first OOH companies to go programmatic. Now I'm on the other side of the transaction, buying that same inventory through Vistar's DSP. The infrastructure I helped stand up a decade ago is the infrastructure I'm building on.

The week AI let us down

Every market page needs a hero image of its city. We'd been generating these with AI, and to be fair, the AI was very confident about its work. Unfortunately, it was also very wrong. It put a river through downtown Nashville. It relocated the Space Needle to a neighborhood that doesn't exist. Memphis got what I can only describe as a fever dream of a pyramid next to a bridge that goes nowhere.

We tried three rounds of prompt engineering with reference photos. Each round was wrong in new and creative ways. The AI never hesitated. It just invented geography with absolute conviction.

So we scrapped the whole thing, downloaded real photos from Unsplash for all 50 cities, and ran them through an automated golden-hour color grade. Fifty markets, zero failures, no hallucinated rivers. Sometimes the boring answer is the right answer.

(Norfolk, Virginia: if you're reading this, we're sorry. Unsplash has exactly zero good skyline photos of you. You got the best we could find. We'll keep looking.)

The pricing episode

I need to talk about pricing because it happened three times this week.

Monday: two tiers. Standard for 45 markets, Premium for the 5 most expensive cities. This created a question no customer should have to ask: "which tier is Nashville?" If you have to check a tier list to understand the pricing, the pricing is broken.

So we collapsed it to one plan. $999 a month. All 50 markets. We deleted 706 lines of code. Felt great.

Apparently not great enough. Wednesday: I wrote an 800-line PRD for three packages. Standard, Pro, and Max. Nested listener routes, venue-type optimization, and a lift-weighted fill algorithm. It was beautiful, ambitious, and completely insane for a product with zero paying customers.

By Thursday morning I'd killed it. Back to one plan. The three-package spec went into the archive. Maybe it comes back someday when there are enough customers to justify the complexity. For now: one plan, one price, one answer.

The lesson, which I apparently need to learn more than once: simplify until it hurts, and then check if it actually hurts anyone besides you.

Meanwhile, in Tasuki-land

Tasuki is an AI consulting agent, still pre-launch. A business owner describes a broken process, the agent diagnoses it, and Tasuki builds the fix. We did some work this week on the early conversation experience — how the agent opens, how it earns the trust to ask harder questions. It's coming along.

The only inbound interest Tasuki has generated so far is an email from a Spanish communications agency offering to buy the domain. So, revenue-wise, we're exploring all options.

What's next

We have a signal. Our detection system flagged a podcaster who was talking about billboards on his show. Time to reach out.