Set Up monday.com Pro — Decision + Setup

Codified from Gmail draft 19dc1115bd294376 · Apr 24 2026

Honest answer first

DECIDE before setting up. $56/mo = $672/yr.
The question is NOT "can I afford it." It's "will I actually use it weekly for 6+ months."
Sheets + Gmail handles 80% of what monday does, for $0.
Only worth it if you have multi-person workflows that Sheets can't visualize cleanly.

Decision gate — answer Y/N

1. Do you have ≥3 people who need shared task visibility right now? (You = 1, Mildred = 2, Chanie/Mom occasionally = 3)
2. Do current consulting clients (Eden Gardens etc.) want to see a board?
3. Will you log in daily for the first 30 days, no exceptions?
4. Have you tried Trello / Notion / Asana before and abandoned them? (If YES — high risk you'll abandon monday too)

Decision rule:
- 3+ Yes on Q1–Q3 AND No on Q4 → set up
- Otherwise → skip, stay on Sheets

If skip — what to do instead

Build a single Google Sheet Hook Street OS Master Tracker with these tabs:
- Active Engagements
- Property Operations
- Personal Loops
- Pipeline

Share with Mildred. Use conditional formatting for status. Free.
Revisit monday.com decision in 90 days if Sheet feels constrained.

If set up — execute these steps

Step 1 — Trial first (5 min)

• monday.com → Start free trial
• 14 days, no credit card initially
• Pick "Pro" tier so you see all features

Step 2 — Workspace structure (15 min)

Create workspace: "Hook Street". Create 3 boards (start with 3, NOT 10):

Board 1: Active Engagements
- Rows = Clients
- Columns: Phase | Status | AR Outstanding | Next Action | Owner | Last Touch

Board 2: Property Operations
- Rows = Property (9312, 9332, NY home)
- Columns: Vendor | Issue | Status | $ | Date Opened | Resolution

Board 3: Personal Loops
- Rows = Open items (your HOW-TO drafts go here)
- Columns: Type | Deadline | Status | Time Estimate | Notes

Step 3 — Add Mildred (5 min)

• Members → Invite → mildred@hookstreetcapital.com
• Role: Member (NOT Guest — Guests are read-only)

Step 4 — Automations (20 min)

• Status changes to "Done" → auto-archive after 7 days
• Item stuck >14 days → notify Sam
• Date column reaches today → notify owner
• New item created → email Sam

Step 5 — Integrations (15 min)

• Gmail → Star an email → auto-create monday item
• Google Calendar → sync due dates
• Slack → if you use it (you don't)

Step 6 — Migrate existing data (30 min)

• Pull 21 EG action items from BOS ops summary → Active Engagements board
• Pull current STR vendor list → Property Operations
• Pull all [HOW-TO] drafts → Personal Loops board

Step 7 — Daily habit (ongoing)

• 5 min morning: review Personal Loops + flag today's
• 5 min EOD: status updates
• Friday: Mildred reviews + clears stale

Step 8 — Day 13 of trial: pay or cancel

• If you've logged in <10 of 13 days → CANCEL, monday isn't for you
• If you've used it daily → upgrade to Pro 2 seats ($56/mo)

Done state

• 3 boards live, actively used
• Mildred logging in daily
• Nothing duplicated between Sheets and monday (kill the Sheets version)
• One source of truth for tasks/projects/clients

Time + cost

• Setup: ~90 min initial
• Ongoing: 30 min/week
• Cost: $0 trial, $56/mo if kept