Pepper
Your operating picture, reduced to what matters.
Preparing your briefing…
What moved
TodayGathering the day’s progress…
Plan with Pepper
Use this only when you want to work through a plan together.
Tell Pepper what is on your mind in ordinary language. She considers your open tasks and the next 36 hours of calendar, then proposes a practical plan. She will not call, send, book, spend, negotiate, approve, or change your calendar.
Ask for a plan in your own words.
Needs your decision
Pepper has ordered these by consequence and deadline. Nothing changes until you choose.
Gathering decisions…
Oscar assurance record
Review findingsLoading…
Oscar independently checks material facts, evidence, completion claims, reasoning, risk, and confidence in Pepper proposals. Oscar recommends; Leif or Jaimee decides.
New Pepper proposals will appear here after the daily review.
Tools and records
Planning, source records, learning, health, settings, and review history live here when you need them.
Your read-only calendar
Work Calendar
Upcoming events and readinessLoading…
Only the iCloud calendar named Work is imported. Access is read-only: events help Pepper plan readiness work, but the app will not create, edit, or remove an iCloud event.
Refresh Work Calendar to see the next 120 days.
Owner-controlled memory
What Pepper remembers
Saved memoryLoading…
Save only facts you want Pepper to use in future planning: a standing constraint, preference, contact fact, commitment, or useful context. Email, calendar entries, and casual dialogue are never stored here automatically.
Add facts Pepper should reliably carry into future plans.
What Pepper has learned
Visible, scoped, and reversible. Source text never becomes a rule.
Preferences and correctionsLoading…
One event is history, not a rule. Pepper may suggest a repeated pattern, but only Leif or Jaimee can choose Remember this. A preference can improve a proposal; it cannot authorize sending, spending, scheduling, deletion, or another consequential action.
Pepper will keep treating each new source as evidence, not a command.
Focus
What needs you today
Phone alerts are off. Enable them to receive task reminders after closing Personal OS.
More filtersAll people · All ventures
Reading your queue…
Work packets
One place for the outcome, next move, missing pieces, people, and handoffs.
Dispatches
Loose ends, safely held. Capture first; decide what they mean when you have room.
Use the center Capture button when something needs a safe landing place.
Proposal inbox
One decision at a time
Nothing becomes work until you choose it.
Pepper suggestions, shared ideas, and email findings wait here as separate proposals. Each card should answer: what is being proposed, why, and what choice is needed.
Share an idea
Safe cleanup
Possible duplicate to-dos
Compare before changing anythingLoading…
Checking only creates proposals. Both complete to-dos stay visible until Leif or Jaimee explicitly merges them. Decline changes nothing; a merge can be undone until either task is edited.
Read-only intake
Email triage
Email proposalsLoading…
Automatic Pepper review: up to 25 unread Inbox messages from the last 30 days are classified as work, schedule, money, personal, security, updates, newsletters/marketing, or junk. Gmail stays read-only: Pepper cannot send, delete, archive, label, negotiate, approve, or mark a message read. Full message text is used only transiently when detail is needed and is not stored.
Pepper will automatically check the unread Inbox; you can also check it now.
Event dossiers
One conclusion up front; sources, uncertainty, preparation, and outcomes underneath.
Preparation and follow-throughLoading…
Pepper can connect and organize read-only email and calendar evidence. Facts name their source; inferences and recommendations stay labeled. Nothing sends, books, spends, or changes a source record.
Pepper will surface a meaningful connection or source change here.
System status
Automation Health
Pepper activityLoading…
This is a read-only status board. It shows when Pepper last checked each source and whether the scheduled review completed; it never reveals credentials or email contents.
Decisions
Questions awaiting an answer
Reading your decisions…
Portfolio
Venture readiness
Fill the gaps before automating.
Reading venture records…
Pepper · Chief of Staff
Latest session
No session block yet. The next working session will appear here.
Quality control
Inspect real behavior, then leave evidence another person can reproduce.
Five-minute quick startStart here
- Today: Can you identify the first useful action without explanation?
- To-dos: Inspect one task's state, dates, assignee, recurrence, and details.
- Inbox and More: Check whether proposals, source boundaries, Work Packets, and system status make sense.
- Themes: Compare Tomorrowland and Matrix once. Atmosphere may change; content and authority must not.
- Report: Submit one reproducible finding below. The app attaches your current screen and theme.
Your boundary: You may inspect sensitive records and work through the real product for this evaluation. Keep private information confidential. Your changes affect the live testing workspace and are attributable to your account; do not send, spend, sign, delete, reset, or change a connected provider merely to test a control.
Feature guideWhat to inspect
Today
Fixed commitments, no more than three potential priorities, watch items, capacity, and an honest closeout. Sunday should remain calm until someone deliberately shows upcoming records.
To-dos
Dates, deadlines, estimates, assignees, task types, recurrence, completion history, and exact undo. Home remains task-first; Work Packets are optional escalation.
Inbox
Raw captures, shared ideas, duplicate review, email proposals, and Oscar assurance. Gmail and iCloud remain source systems; Personal OS does not silently act on them.
More
Work Packets, field evidence, music engagements, Event Dossiers, automation status, memory, appearance, and review rhythm.
Pepper and Oscar
Pepper recommends and organizes. Oscar verifies consequential claims. Exercise both roles, but neither should imply an external action occurred without evidence or owner confirmation.
Character themes
Tomorrowland is the default. Pepper, LCARS, Indiana, and Matrix may change visual character without changing information, control meaning, privacy, or Sunday behavior.
Beta-testing checklistBeyond the happy path
- Try phone and desktop when practical; name the device and browser in your steps.
- For A/B comparisons, change one thing at a time and name the condition you tested in the reproduction steps.
- Check long text, narrow screens, loading, empty, error, offline, keyboard, focus, and reduced-motion states.
- Use Blocking only when a core path cannot continue; Major for materially wrong behavior; Minor for contained defects.
- File a bug when behavior contradicts the interface. File a product suggestion when it works but the workflow should change.
- Submit one problem per report. Include exact error wording, but never credentials or temporary sign-in codes.
- Do not forward, screenshot, or copy private records into another service.
- Use obviously labeled test records when possible so Leif can clean them up after the beta.
Your submitted reports
Your first report can be a bug, confusion, accessibility issue, performance concern, privacy concern, or product suggestion.
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