Mike MacDonald

Founded and built solo · 2026

Herding Cats

An agentic operating system for touring dance competitions.

Role
Founder, designer and builder
Timeline
Apr 2026 – Present
Platforms
Web, iOS, Android
Herding Cats web app: an AI staffing plan for a two-city weekend, with a suggested person, flight and fare for each position
Herding Cats on iPhone: a judge’s travel day with flight, hotel and confirmation number
Close
Herding Cats Try the app · demo data
Travel day

Your travel day, all in one place.

Flight, hotel, roommate, confirmation number: one screen. Tap “I’ve landed” and your event manager knows.

Tap the tab bar or the big button in the phone.

3 apps
web, iOS & Android
6
unique add-on modules
1,100+
staff profiles and counting
17 hours
average bug fix turnaround time

Overview

Staffing, flights, hotels, equipment, merch and finance for touring dance competitions, in one AI-native system. Founded and solo-built; live on web, iOS and Android.

My role

  • Founder: product, design, engineering and go-to-market
  • Agent and human-in-the-loop UX
  • iOS, Android and web apps, built with frontier AI tooling
  • Brand, pricing and launch (ADCC 2026)

Results

  • Live on web, iOS and Android
  • Active design partners on registration, show day and judge scoring
  • Flights, hotels and rental cars booked in-app; costs roll into finance
  • Onboarding configures a whole company from its existing documents
Onboarding

Start with the documents you already have

Nobody wants to set up software. Users drop in their working docs, spreadsheets, PDFs, emails, contracts and notes, and an LLM pipeline configures the company: settings, tour events, rosters, venues, hotels and staff profiles. A proactive agent flags what is missing and nudges people to finish the records. Below is the real intake UI on canned data: six unsorted files go in, the Kitten identifies each one, the roster imports itself, and fourteen events land on the board.

Staffing

Staffing that thinks about travel

AI staffing fills rosters across multiple events from company staff and event criteria, optimizing for travel costs, lodging logistics, availability and preferences. Humans approve; the agent explains its trade-offs.

Herding Cats web app: a weekend staffing board for Pittsburgh and Birmingham with a suggested person, flight and fare for each position, and an Apply weekend plan bar
An AI staffing plan for a two-city weekend: 23 picks, each with a flight, a fare and the time to spare, waiting for one approval
Herding Cats web app: the Run AI staffing dialog for a three-event weekend. Its rules, in order: who’s free, right person for the position, flight prices compared across every event on the weekend, easy travel, not too many events, and one that is always on: nobody is put on two events on the same weekend
The rules a run follows, in order. Nothing is assigned until a person reviews and applies it
Herding Cats web app: a dialog with the Kitten’s pick for a judge, three flight options with prices and time to spare, the reasons for the pick and the other candidates
The Kitten’s pick for a judge: three priced flights, and its reasons
Herding Cats web app: the staff directory, listing contact details, home airports and positions
The staff directory the plans draw on
One run, start to finish, from the guided demo on tryherdingcats.com: three cities on one weekend, picks with priced flights, flight timing explained, rooms built by the rooming rules, and the list sent to the hotel
The weekend

The whole weekend, in your pocket

Judges, crew and drivers get a travel day and a show day that answer the only questions they have: where am I going, when, with whom, and what is next. One tap to confirm a landing; the event manager sees it instantly.

iPhone: travel day with today’s flight, an “I’ve landed” button and the hotel
Travel day
iPhone: show day with call time, crew count and what’s next
Show day
iPhone: event manager dashboard with season counts and crew landing status
The event manager’s view
Herding Cats web app: an event overview with readiness at 85%, staffing, flights and rooming counts, the event timeline, venue and hotel details
The same event on the web: readiness, staffing, flights, rooming and the timeline
The Kitten

Ask the Kitten anything

A context-aware assistant that sees what the user sees, answers from company data and nudges toward the next action instead of dumping raw chat output. The AI lives in cards, actions and suggestions, not a separate tab.

iPhone: the Kitten copilot answering a question about a delayed flight
Seeing what you see
Three “Kitten noticed” cards: a hotel block cutoff in 10 days with 4 rooms unassigned, a venue contract still unsigned five weeks out, and a debrief that 3 of 9 crew have not answered. Each has one action button, a No thanks link and a receipt naming who it was sent to and how
It notices before anyone asks. Each card names one next action, and who it was sent to
The Kitten assistant, asked to push the Sunday staff brief to 8:30 am, shows the change from 7:45 to 8:30 with Approve and Reject buttons and a 15-minute expiry
A change comes back as a card to approve or reject, and expires if nobody does
The Kitten assistant, asked to move a whole event back a week, declines: event dates stay a human decision. It names the two admins on the event and offers to list the 9 booked flights and 14 hotel nights that would be affected
Event dates are locked from it on purpose. It says who can change them, and offers the impact first
Travel

Book it without leaving

Google geolocation, SerpAPI flight pricing and history, and HotelPlanner let travel coordinators book flights, hotels and rental cars in-app, with every cost rolled up into a comprehensive financial reporting module. The staffing plan already knows what each person costs to get there: fares are priced live, compared across the weekend’s events, and the Kitten explains its pick.

Herding Cats web app: the Travel module listing staff who still need flights for each weekend, beside open issues
Travel: who still needs a flight, weekend by weekend, and what is in the way
Herding Cats web app: an event’s travel tab with each person’s inbound and outbound flights and booking status
One event’s travel: every person’s inbound and outbound legs
Herding Cats web app: an event’s rooming board with rooms, roommates and confirmation numbers
Rooming board: rooms, roommates and confirmation numbers
Herding Cats web app: the Finance module with season revenue, expenses, net, margin and a breakdown by brand
Finance: the season’s revenue, expenses, net and margin, by brand
Herding Cats web app: an event’s profit and loss with registration revenue and an itemized list of flights
One event’s profit and loss, every flight itemized
The loop

A loop measured in hours

Bugs, feedback and feature requests from active design partners are triaged, prioritized, designed, built and shipped within days, often hours. The inbox is the product’s heartbeat.

iPhone: the inbox with schedule changes and rooming updates
What needs you, up top
A section of tryherdingcats.com headed “Saturday’s problem. Next weekend’s feature.” beside a timeline: Saturday, something hurt at load-out; Monday, a 20-minute call; Wednesday, a first cut on the customer’s account; Friday, live for them first; next Saturday, they run it and say what’s next
How tryherdingcats.com puts it to design partners: what hurt at Saturday’s load-out is live on their account before the next weekend
Judgment

Principal means judgment.

Building a company alone with frontier AI tooling changed what the title means to me. The hard part was never producing screens; it was deciding what to build, what to skip, and what the agent should never do without a human in the loop.