A vertical-SaaS-plus-services play: a connective stack of integrations (PaintScout, HubSpot, Airtable, QuickBooks) wrapped in a dedicated Sales-Engineer pod. 26 active clients. ~$835K annualized run rate. The tools work — they just didn't work together until we showed up.
Painting companies in the $4–10M revenue band already own the right tools. They use PaintScout to estimate, HubSpot to manage their pipeline, Airtable to wrangle data, QuickBooks for finance. The tools just don't talk to each other. Boolean is what makes them talk — and the team who keeps them talking when something changes.
Boolean's ICP is specific enough that Chris (the founder) can name the avatar in one sentence. Nicknamed internally "The Delegating Paint Owner" — sourced from the Dent KPI Value Canvas filled 2026-05-03.
Owner of a regional painting company who has started stepping out of the day-to-day and built a leadership layer — managers, estimators, an office team. Identity wraps around stewardship: protecting the people, the reputation, and the lifestyle the business funds. Not impressed by trendy tech, but optimistic about AI/automation that clearly helps staff.
They don't fear growth or change. They fear drifting blind into a bigger company that's harder to steer — where margin and quality slipped quietly and they can't say when. What they want most is to feel like a real steward again: calm, informed, in control.
One dashboard. Sold margin, production reality, change orders, labor burn, cash. Weekly review takes 30 minutes — not an emotional spiral.
Manager-first dashboards (not owner-only). The team has the data they need without escalating to the owner. Delegation actually sticks.
Margin drift, cash gaps, schedule risk surface in days — not at month-end close. Fix small problems before they become margin-killers.
Live roster from boolean-knowledge/clients/. Subscription amounts from each client's profile.md. Domains pulled from active stakeholder records. ACV ranges from $200/mo (review-only) to $6,000/mo (full automation). Median monthly equivalent is ~$2,000/mo.
Concentration is $2K–$3K/mo — 10 of 22 confirmed-MRR clients sit there. One outlier at $6K/mo (Integrity Painting). Four review-only or small-scope ($200–$1K).
Three SEs carry ~85% of the portfolio (22 of 26 client relationships). Chris owns three accounts directly — Blair, Paint Denver, SNL — all classified as founder-touch / churn-risk.
Open any card to inspect a real client. They're regional U.S. residential/commercial painters — most $4–10M revenue, family-owned, 3–5 office staff. The portfolio represents Boolean's product/market fit: low churn (1 confirmed in last 12 months), expanding via change-orders, references-driven growth.
Boolean's structural innovation is the AI agent fleet — ten Claude-Code-powered personas that operate as force multipliers across the SE pod, ops, and engineering. Not a marketing flourish. They review every PR, audit every drift, sweep every weekly, ship every Prismatic deploy.
| Chris Kiefer | Founder · strategy, sales, last-line client owner. Active SE for SNL. |
| Cody Hopkins | Director of Ops · runs the SE team, owns tooling + the agent fleet. (You.) |
| Celine | SE · 7 clients |
| Dan Labrador | SE · 7 clients (retention risk flagged 3/31) |
| Eveguel | SE/Dev · 1 client + Kairos automation agent |
| Rensy Lomboy | SE · 8 clients |
| Marcel | SE · promoted candidate (status uncertain) |
Engineering bench is now Cody + Claude Code + Chris only — Rod & Justin sunset 2026-04-15 in the radical-reduction pivot.
/hat-loadable inside Claude Code)| Norman | Ops intelligence · SE grading · brief author · drift reports |
| Vera | Design architect · Design OS · gate reviews |
| Marshall | Airtable engineering · QBO reporting · sole Airtable writer |
| Rory | Structural builder · OAuth · webhooks · platform engineering |
| Kairos | Dev automation · Prismatic/Zapier/Make · Railway-hosted |
| Luke | Historian · audit/staleness pipeline · daily & weekly publication |
| Mark | Field reporter · open-web research with skepticism & freshness |
| Norm · Dara · Gabby | Benched 2026-04-09 (consolidated into Rory + Norman) |
The agents aren't autonomous services — they're prompt-context personas inside Claude Code that compose on demand. SOUL.md + IDENTITY.md + TOOLS.md per agent. No allowlists, no daemons, no $$ API costs from idle agents. The whole fleet runs on Cody's Claude Code subscription.
Q1 closed at $216K revenue with a $6K net loss. April 2: pivot decided — kill Prismatic, rebuild platform in-house, cut headcount to a lean SE pod. April 9–15: Riz, Veronica, Justin, Rod sunset. The first five weeks of Q2 absorbed the entire Q1 loss and added $6K of net income on top.
May MTD (8 days) is already at +$9.9K net income — the month is on track to be the most profitable in recent record.
| SE direct labor | ~$236K |
| Software / hosting | ~$79K |
| Admin / sales labor | ~$346K |
| G&A / general | ~$119K |
| Advertising / marketing | ~$24K |
| Total | ~$821K |
Real gross margin ~60% once SE labor is properly classified (book-hygiene gap: $84K YTD currently sits in "uncategorized Gusto labor").
Killing Prismatic. The integration platform we currently run on costs ~$48K/yr — nearly all of the $79K software/hosting line.
Decided April 2. Building a Norman-native event-driven platform (25 trigger events) that owns the orchestration and removes the dependency. ~16-week build. When it ships, ~5 percentage points of margin step-change at current scale.
Cody leads architecture. Chris supports. Kairos (the dev-automation agent) is co-resident on Railway and exercises the new platform daily.
| Ortiz Decorating | $16,250 | current |
| Connor Painting | $15,000 | 31–60 |
| Miriam Freeman (SNL) | $11,073 | current |
| Shaun McMurry | $10,119 | 31–60 |
| Roll Call Painting | $5,000 | 91+ |
Total AR: $64,050 across 22 customers. Top 5 = 90% of total. Roll Call's $5K in 91+ is the single concrete write-off candidate; otherwise the book is healthy.
Sourced from Fireflies meeting record + commit history + boolean-knowledge change log. Every event below has a primary source citation in the operating record.
01KH1MEC…). Cody on the record: Chris is the technical bottleneck preventing new product development. Sets up the strategic decision that lands April 2.01KN7YZ7…). Decision: rebuild integration platform in-house to retire Prismatic. Event-driven, 25 trigger events, ~16-week build. Cody owns architecture./ship skill becomes its executor.paintos-shell multi-tenant substrate. Sean + Adam onboarded; staged rollout to remaining crews Mon 5/11. Blueprint to repeat across portfolio.Ship the Norman-native replacement for Prismatic. Eliminates ~$48K/yr COGS, removes single biggest vendor risk, gives us a real moat (vertical-specific event model) instead of vendor-lock.
Owner: Cody · ETA Q3 2026
Q1 closed zero new clients. Marketing function is six days old. YouTube cadence + 1-2 industry collab episodes (Nick May, Mike Gore-Hickman) + ICP-targeted CTAs are the bet. Goal: predictable inbound discovery-call volume by end of Q3.
Owner: Chris (presence) · Cody (production) · ETA cadence by 06-30
Kennedy v1 shipped yesterday on the multi-tenant paintos-shell. Repeat across the portfolio. Each new tenant added at near-zero marginal engineering cost is the unit-economics inflection.
Owner: Cody + Vera · 3–5 tenants by Q4
acquisition Q1 = 0 new clients. Marketing is six days old. Until we prove the channel, growth is reference-only and slow.
founder bottleneck Chris is the technical bottleneck flagged 2/10. April moves are the bet, not yet validated. Worth tracking whether the bottleneck has actually moved or just changed shape.
Prismatic dependency Real until the rebuild ships. Single-vendor exposure on the orchestration layer.
SE retention Dan Labrador resignation flagged 3/31, still in place. If he leaves, Heiler coverage breaks and the bench is thin.
Select Painting Zero W17 activity, $23K AR exposure as of 4/8. Biggest churn-with-money-attached risk in the portfolio.
books hygiene $84K of "uncategorized Gusto labor" hides real margin. R&D credits possibly under-claimed. Fixable; not load-bearing.