docs/ops/personal/thomas/2026-01-20

Jan 20, 2026 - Thomas (Monday)

My Responsibilities (from today's huddle)

Primary: Systematic Outreach System

  • Walk Michael through OS features
  • Send LinkedIn outreach to first batch (~20 contacts)
  • Continue developing systematic outreach automation

Secondary: Bowman Deal

  • Wait for Bowman response, then schedule discovery call
  • Refine proposal based on discovery

Current Status

Systematic Outreach:

  • Contact research prompt working (generates ~20 contacts with draft emails)
  • Contacts saved under research/contacts/
  • Ready to execute first LinkedIn outreach today

Bowman Proposal:

  • $75k consulting partnership drafted
  • Decision: Don't send formal proposal until discovery call about broader AI strategy
  • Flexible on monthly cancellation if he pushes back
  • May implement Claude Enterprise instead of DaisyAI platform

Today's Focus

  1. ✅ Morning huddle with Michael (walked through OS, discussed Bowman)
  2. Send LinkedIn messages to ~20 contacts from mentor list
  3. Continue systematic outreach system development
  4. Plan cron automation for daily contact generation

Work Log

Morning

  • Huddle with Michael (9:42 AM - 11:27 AM)
    • Walked through OS features: content pipeline, sales docs, contacts, outreach playbook
    • Deep discussion on Bowman pricing ($75k, flexible terms)
    • Agreed on FDE vs SaaS model shift
    • Aligned on systematic outreach vision: 20-30 contacts/day with 15min review
    • Michael taking on content creation (X, LinkedIn, Substack)

Afternoon

  • Implemented agent-driven outreach system (complete rewrite)
    • Deleted old template-based system (rigid email sequences)
    • Created new agent-driven architecture:
      • research/outreach/segment-prompts.yaml - segment config
      • docs/agent-prompts/vc-healthcare-list.md - VC research prompt
      • docs/agent-prompts/pe-healthcare-list.md - PE research prompt
      • docs/agent-prompts/regional-um-accounts.md - regional accounts prompt
      • src/lib/outreach/list-parser.ts - parse markdown contact lists
      • src/lib/outreach/pdf-generator.ts - compact HTML/PDF export
    • Updated /outreach skill with new workflow
    • New flow: /outreach generate mentors --count 10 → research → review markdown → /outreach send
    • Key change: LLM-personalized hooks per contact, not rigid templates

Thinking/Decisions

  • Business model shift: Services as distribution channel for product, not the other way around
  • Bowman approach: Need discovery call before formal proposal—don't assume what he needs
  • Claude Enterprise option: If all he needs is chart summaries, could implement Claude directly and just charge consulting fee
  • Outreach automation: This is the "noble project"—if we nail it, can extend to other target groups (PE firms, VCs)

Blockers

  • Bowman proposal blocked on discovery call
  • Jose hasn't looked at emails (possible spam filter)

Tomorrow

  • Follow up on LinkedIn outreach responses
  • Continue systematic outreach development
  • Check if Bowman responded

Notes

  • Michael excited about OS ("extremely innovative")
  • Discussed ZoomInfo disruption thesis (might short them)
  • Content ideas: "Doritos theory of AI content", "Future of work is Geico"

Daisy

v1

What do you need?

I can pull up the fundraise pipeline, CRM accounts, hot board, meeting notes — anything in the OS.

Sonnet · read-only