Jam-Session
Artifact info
Title:

Iris Operations, Budgeting & Holos Planning Sync

Engagement:

Iris Internal

Client:

Iris Cocreative

Meeting Date:
June 23, 2026
Next Meeting Date:
June 16, 2026
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James Redenbaugh
Ashle Gilreath
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Meeting Summary

Opening & Context

**James** and **Ashle** reconnected after James's honeymoon, with James noting it's been challenging to get back into the flow of building and using cloud code. He was pleased that things continued smoothly during his absence and that the team accomplished a lot. **Ashle** shared updates on her new house and adjusting to a heat wave without air conditioning.

🏗️ Holos Movement Project Planning

Budget Framework & Timeline

The team needs to present a refined budget and timeline to Holos Movement, with **Emmanuel** and **Laura** returning from a week off (07:01). There's been no clear request for a finite budget, but the Holos team has asked for a general timeline and scope of possibilities across discussed features.

A core challenge: **ClickUp** and the **app map in Holos** currently serve as two different sources of truth (08:19). James wants to reconcile them — ideally syncing them, or recreating the app-organized structure in ClickUp and archiving the original. The Holos team has access to the app map but doesn't actively use it, so consolidation is viable.

Monthly Retainer Model

Rather than presenting a large lump-sum budget, James proposed shifting to a **suitable monthly scale of support** that meets Holos's development goals while helping Iris plan team capacity (15:03). This would allow clear allocation of percentages of James's, Sean's, Ivan's, and Munia's time across projects.

**Ashle** suggested building an internal **ClickUp dashboard/calendar** to visualize workload across the team — helping forecast capacity, determine whether Sean can take on additional clients, plan trips, or identify hiring needs (12:43).

[technology="Collaboration Management Tools"]

High-Level Timeline Deliverable

James will generate a simplified high-level view from the existing detailed plan, similar to the four-phase timeline used in the initial proposal. The goal is to produce **two levels of information** from the same data:

- An external timeline + budget for the Holos team

- An internal view showing profit margins, team allocation, and buffer space at project end

💰 Billing Rates & Financial Strategy

Current Rate Structure

James walked through the current effective rates:

- **James:** $150/hr (with ~290 hours on Holos to date)

- **Sean:** $125–$150/hr billed; effective contractor cost $49/hr in May, ~$77/hr in June on retainer

- **Ivan:** $90/hr cost

- **Munia:** ~$80/hr cost

Iris is currently making profit on all team hours, with administrative costs built into client-quoted rates (26:20).

Tiered Rate Recommendation

**Ashle** strongly recommended James increase his own rate — suggesting it should be at least twice Sean's, given the strategic, conceptual, and architectural work he contributes (20:30). She proposed a **three-tiered external rate system** modeled on Pro Social's approach:

- Tier 1: Standard market rate

- Tier 2: Financially capable but mission-aligned clients

- Tier 3: Partners, Global South, or early-stage organizations

This replaces ad-hoc "friends and family discounts" with a structured, sustainable framework. Existing Holos rates wouldn't change, but new client engagements should reflect higher valuation of James's time.

Salary & Payroll Planning

James wants to start paying himself a **regular $10,000/month salary** (48:11). Open questions remain on contractor vs. employee setup, tax implications (15.2% self-employment tax), home office deductions, and health insurance routing. **Ashle** offered to help process payroll and set up the structure when ready.

🌐 Community Platform Strategy

Wendy's Project Status

**Ashle** met with **Wendy**, who had been considering finding another developer due to slow response times. After a productive conversation, immediate needs were resolved (split between Sean and Ashle), and upcoming work includes a new resource page and potential team page redesign to accommodate research advisors.

Wendy expressed interest in building a **community platform** — she had been evaluating **Circle** but is open to alternatives.

Replicable Membership Template Vision

James clarified the strategic framing: rather than "replicating Holos," the goal is to create a **templateable online membership community** that can be easily duplicated and tailored per client (01:03:18). This same approach applies to **Gaia Warriors** and **The Hermitage Project**.

The offering would include:

- Membership capabilities

- Online learning

- Messaging

- Resource sharing

Pricing model: setup cost comparable to ~3 years of Circle, with significantly lower ongoing costs. Ashle will continue managing Wendy's smaller tasks and revisit the community platform conversation when timing aligns (likely early next year).

[technology="Custom Membership System"]

[technology="Online Learning Platforms"]

🌱 A Lolly (Pro-Social Market Economy)

James acknowledged the project is moving slowly as he works to wrap his head around what pro-social market economy actually means conceptually (56:51). After last week's call, a clearer homepage direction emerged. James plans to mock something up personally before bringing **Munia** in to accelerate execution. He expects meaningful progress within a few weeks. The project remains within scope and budget.

🤝 Community Solutions Opportunity

The follow-up email was sent last week with no response yet — James will send a gentle follow-up if he doesn't hear back soon. The meeting went very well and the team is excited about the potential engagement.

🤖 Task Automation with Claude

James demonstrated using **Claude** [tag="claude"] with **ClickUp** connectors to auto-generate tasks from meeting artifacts. The system identifies workstreams, creates folders, generates subtasks, and assigns ownership — significantly reducing manual entry time.

Until full automation is built into the artifact pipeline, **Ashle** will manually shepherd tasks into ClickUp using Claude as an assistant. James will share relevant context exports so Ashle's Claude instance has the same grounding.

Artifact Coordination Workflow

To streamline meeting artifact handling:

- James will forward new client meeting invites/emails to Ashle in advance

- Ashle will pre-populate people and photos in **Airtable** [tag="airtable"]

- James will always send generated artifacts to Ashle

- A new **global artifact page on Iris** will centralize visibility across all engagements

[technology="Communication Automations"]

🔐 AI Vendor Risk & Data Privacy

**Ashle** raised concerns about reliance on Claude given likely future price increases. James explained his mitigation strategy: everything is built on **GitHub** [tag="github"] and can be managed by any LLM, including local models. He recently purchased a PC to test running powerful models locally — referencing AMD's new ~$1,500 desktop unit capable of running Claude-comparable models.

For automations using **n8n** [tag="n8n"], James is architecting workflows so personal data is removed before sending to LLMs, ensuring vendor swap-ability if needed (42:25).

On **GDPR/data protection**: Ashle confirmed Anthropic's data protection terms are now automatically incorporated into their terms of service, removing the need for a separate DPA for standard data processing.

📋 Operational Improvements

Deadline Management

James reflected that timelines often shift as reality sets in — usually because clients take more time than expected, and Iris doesn't maintain enough top-level awareness. The goal: **hold deadlines to a higher internal standard than clients do**, communicate shifts proactively, and use a centralized ClickUp overview board for major launches.

Contractor Documentation

No centralized location currently exists for W9/W8 forms. **Ashle** will set up a secure **Google Drive** folder structure and collect forms for **Sean**, **Ivan**, **Munia**, and **Andy** going forward.

Hosting Invoice Audit

James needs to review hosting invoices for hosting-only clients to determine who needs to be invoiced and whether costs need updating.

### Action Items

**James Redenbaugh**

- Hone in on Holos budget and timeline details next week after Emmanuel and Laura return (07:01)

- Reconcile ClickUp and Holos app map, ideally syncing or migrating to single source of truth (08:19)

- Generate simplified high-level timeline view of Holos workstreams for client + internal use (10:13)

- Send Ashle detailed breakdown of historical hours by person and project for budget analysis (33:42)

- Grant Ashle access to ClickUp and Bonsai (52:53)

- Build global artifact page on Iris to centralize visibility across engagements (01:23:30)

- Forward new client meeting invites/emails to Ashle proactively (01:24:45)

- Send all generated meeting artifacts to Ashle automatically (01:23:15)

- Look into contractor vs. employee setup for $10k/month salary, including home office deductions (50:01)

- Review hosting invoices for hosting-only clients to update costs and billing (01:26:08)

- Follow up with Community Solutions if no response received (53:14)

- Mock up A Lolly homepage direction before bringing Munia in (56:51)

**Ashle Bailey-Gilreath**

- Research internal ClickUp dashboard/calendar options for team workload visualization (12:43)

- Compile historical time tracking and invoicing data for Holos budget framework (16:53)

- Continue managing Wendy's smaller tasks; coordinate with Sean for resource page and team page updates (01:06:35)

- Revisit community platform conversation with Wendy when timing aligns (01:07:05)

- Manually enter tasks from artifacts into ClickUp using Claude until automation is built (01:18:24)

- Set up secure Google Drive folder structure for contractor W9/W8 forms (01:27:53)

- Collect W9/W8 forms from Sean, Ivan, Munia, and Andy (01:28:19)

- Monitor James's calendar for new client engagements and artifact coordination (01:25:00)

- Set up recurring weekly Tuesday 11am sync (01:33:42)

Relevant Initiatives

Talent Access

Priority: 
High
Size: 
M
Planning Stage

Iris Studio Design

Priority: 
Very High
Size: 
L
Creation Stage

New Business Model Development

Priority: 
Very High
Size: 
XL
Planning Stage

Team Resources

Priority: 
High
Size: 
L
Planning Stage

Meeting Artifact Automation System

Priority: 
High
Size: 
L
Planning Stage

Team Capacity Planning Dashboard

Priority: 
High
Size: 
M
Planning Stage

Replicable Community Platform Template

Priority: 
Medium
Size: 
XL
Idea Stage

AI Vendor Risk Mitigation Strategy

Priority: 
Medium
Size: 
M
Planning Stage
Transcript