February 9, 2026 — Will & Derek Strategy Session — 70 min

Playbook OS, Monetization Strategy & Bridger Pivot

Deep strategy session covering the new Playbook OS concept (executable AI playbooks as done-for-you wedge product), HC protocol as thought leadership play, Covenant Secure Compute Cloud update, revenue path prioritization across 5 tracks, premium pricing strategy, Bridger JV pause, and Brad readiness confirmation. Will departed at ~56 min for Covenant meeting.

At a Glance

CRITICAL PATH:
Playbook OS go-to-market definition + Derek's 25-target outreach list + Brad readiness confirmation
NEW CONCEPT:
Playbook OS: turn expert videos/frameworks into executable AI playbooks as premium done-for-you product
PIVOT:
Bridger JV paused (his request, money pinch). Goodwill play: build a framework for his high-ticket offers instead
PRICING:
Premium first, volume later. Done-for-you delivery, not DIY software. Win-your-money-back JV gateway
OWNERS:
Derek (3 actions: Brad, 25-list, Bridger info) | Jason (2 actions: GTM doc, publisher) | Will (2 actions: Wed session, Tyler sync)
NEXT MEETING:
Wednesday Feb 11 strategy session to recenter all workstreams and recommit to cadence

Live Systems & Dashboards

5
Revenue Paths
8
Decisions Made
7
Action Items
4
Blockers
3
Participants
Feb 11
Next Session
Derek Kaschak: 3 Actions
Outreach lead | Partnership pipeline | Playbook OS sales
Immediate: Confirm Brad readiness (today/tomorrow)
This Week: Build 25-target B2B expert list for Playbook OS outreach
This Week: Get Bridger's high-ticket offer details for goodwill framework
Strategy: Niche into 1-2 sub-niches, map domino chain upward
Slack DM Derek
Jason: 2 Actions + Infrastructure
HC protocol architect | Playbook OS builder | Strategic oversight
This Week: Share Playbook OS go-to-market funnel doc with team
This Week: Finish HC publisher auto-registry for meeting pages
Ongoing: Playbook OS infrastructure (~70% done, finishing templates + agent skill references)
Presented: HC protocol, neural registry, Playbook OS concept, live publisher demo
Slack DM Jason
Will Preble: 2 Actions + Covenant
Product strategy | Covenant liaison | Tyler/Carter sync
This Week: Plan Wednesday strategy recenter session
This Week: Schedule Tyler/Covenant technical sync call
Update: Covenant Secure Compute Cloud targeting March 1 launch
Alignment: HC protocol maps well to Covenant infrastructure vision
Slack DM Will

Key Discussion Topics

5 Major Topics

Decisions Made

8 Decisions

Action Items

7 Actions Assigned

Blockers & Risks

4 Blockers Identified

Timeline & Commitments

4 Time Horizons

Next Steps

  • Derek → Brad: Confirm readiness today/tomorrow. If ready, JV becomes priority #1. Report back immediately.
  • Derek → Bridger: Ask for his high-ticket offer links/sales pages. "Won't create work for him." Jason will build a free framework as goodwill.
  • Derek → 25 List: Build the B2B expert target list for Playbook OS outreach. Niche into 1-2 sub-verticals. Think domino chain upward to ideal partners.
  • Jason → GTM Doc: Share the fully fleshed Playbook OS go-to-market funnel with team before Wednesday.
  • Jason → Publisher: Finish auto-registry updates and domain management cleanup for HC publisher.
  • Will → Wednesday: Plan the Feb 11 strategy recenter session. Recommit to cadence. Map use cases to technology. No new rabbit holes without direction.
  • Will → Tyler: Schedule Covenant technical sync for end of week or following week. Align infrastructure with Mastery OS use cases.
  • All → Converge: Stop the drift. Focus on sustainable 5-figure monthly revenue. Every shiny idea gets parked until the Wednesday session filters it through the priority framework.