— THE FRONT PAGE —
State of the Union.
Composite ring, five domain dials, today’s priorities. The editorial front page of your life — read first, every morning.
— FOR THE AMBITIOUS FEW —
You already run a company.
It’s called your life.
Obelisk is for operators, creatives, and quiet builders who take their career, health, money, and people as seriously as they take their work. One editorial surface for all of it — with an AI chief of staff who knows your numbers and tells you the truth.
317 / 500
FOUNDING MEMBERS · LIFETIME PRICE LOCKED
BUILT FOR:· Operators running real numbers· Creatives with a body of work· Founders past product-market fit· Anyone done with ten-tab mornings
obelisk.app
THE STATE OF THE UNION
A week of quiet momentum.
MRR $51.9K · +8.2%Readiness 82Net $487K
COMPOSITE
73
BUSINESS
81
↑ 4.2
HEALTH
76
↑ 1.8
WEALTH
68
→ 0.3
“The composite is up 6 points this month. Your shadow? You skipped three workouts. Don’t trade health for velocity.”
— YOUR CHIEF OF STAFF, TUES 7:14 AM
— READ BY OPERATORS AT —Stripe·Linear·Notion·Anthropic·Figma·a16z·Y Combinator
MRR $51.9K·READINESS 82·NET WORTH $487,230·RUNWAY 19 MOS·STREAK 47 DAYS·DEEP WORK 22H·OKR 68%·MOOD 4.1/5·5K PR 24:18·SAVINGS RATE 41%·MRR $51.9K·READINESS 82·NET WORTH $487,230·RUNWAY 19 MOS·STREAK 47 DAYS·DEEP WORK 22H·OKR 68%·MOOD 4.1/5·5K PR 24:18·SAVINGS RATE 41%·
— THE GUIDED TOUR —
A two-minute walk
through your Obelisk.
Step through the whole arc — from the moment you sign up to the morning your Chief of Staff argues with you. Click any chapter to skip ahead, or let it play.
obelisk.app /onboarding
LIVE TOUR
STEP 03 / 05 · YOUR DOMAINS
Which arenas matter this year?
Pick the ones you’ll measure. You can add or retire any of them later — the Obelisk grows with you.
01Business
02Health
03Wealth
04Career
05Relationships
06Craft
07Spirit
CH. 01 — ONBOARDING · STEP 03 OF 05Begin yours →
— A TUESDAY MORNING —
Two ways to wake up.
— BEFORE OBELISK · 7:14 AM —
- Notion12 unread comments
- Linear8 issues assigned
- Whooprecovery 64%
- Mint3 transactions
- StripeMRR loading…
- Calendar9 events
- Notes.app“things to do”
- Day Onelast entry: 6 days
- Goodreads2 books stalled
- Strava+ 4 more
Ten tabs. Forty minutes. No verdict. Coffee gets cold.
— WITH OBELISK · 7:14 AM —
THE BRIEFING · TUESDAY
A week of quiet momentum.
73COMPOSITE
“MRR cleared $51K. Streak day 47. Marcus is overdue. Today’s one thing: write the Q2 review.”
— ONE PAGE · ONE MINUTE · ONE TRUE THING —
One page. One minute. The day starts decided.
— THE OBELISK —
Thirteen views, four sections, one paper.
The departments of a serious life — filed daily, bound weekly, archived forever.
DEPARTMENTS · 05
- BusinessPortfolio of ventures. MRR/ARR. Deal pipeline.
- HealthSleep, readiness, workouts, nutrition.
- WealthNet worth, accounts, transactions, retire-by date.
- CareerOKRs, skills, milestones, mission.
- RelationshipsTiered contact list. Last-touch. Overdue flags.
DAILY · 01
- The Morning PageToday’s editorial. Read once. Archived forever.
THE LONG VIEW · 04
- The VisionTen-year picture. North star. Milestones.
- The WeekSunday digest. Three wins. Three shadows.
- The LedgerSealed decisions, revisited later for verdicts.
- The ArchiveBound back issues. Searchable. Yours.
RITUALS · 02
- JournalMorning pages. Mood. Semantic search.
- Weekly ReviewSit. Review. Decide what changes.
— TRY IT —
Move the levers. Watch the score.
A live taste of the composite index. Drag any domain — see how a single number reshapes when one part of your life climbs or slips.
74
COMPOSITE
“Solid week. Career and Business carrying the load. Relationships is the soft spot — fix that and you’re in the 80s.”
Business81
Health76
Wealth68
Career82
Relationships58
— PIPES IN —
Plug in once. Watch your numbers fill themselves.
Obelisk reads from the tools you already use. One-tap connections, optional, never required — every domain works manually too.
Stripe
MRR · ARR · churn
Plaid
net worth · spend
Whoop
readiness · HRV
Oura
sleep · recovery
Google Cal
deep work · meetings
GitHub
commits · craft
Linear
velocity · OKRs
Strava
miles · pace
Spotify
soon
Goodreads
soon
Apple Health
soon
Notion
soon
— END-TO-END ENCRYPTED · REVOKE ANY CONNECTION IN ONE TAP —
— A DAY IN THE LIFE · CASE STUDY 01 —
Adeola’s Tuesday.
A single day, hour by hour, lived through Obelisk. The way the surface compounds.
06:14
WAKE
Briefing notification: composite 73 · streak day 47. Three paragraphs read in the kitchen, before the coffee finishes.
07:02
RUN
5K logged automatically from Strava. The streak grid quietly turns one more square red.
08:30
DEEP WORK
Two hours on Layered. The deep-work meter ticks forward. Calendar blocked, no slack, no email.
11:48
DECIDE
“Should I take the Meridian meeting?” Argue mode says no. Adeola declines in writing. Composite holds.
13:20
LOG
“Log a $42 Uber and a $18 lunch.” Ledger updates in one breath. Savings rate recalculates.
17:05
TEND
Relationships flag: Marcus, six days overdue. A two-sentence text, sent. Flag clears.
21:40
REFLECT
Three lines in the morning page. Mood 4/5. Tomorrow’s one thing, written before lights-out.
23:00
CLOSE
The day is filed. The archive grows by one issue. The Sunday digest will know everything that happened.
— THE ARCHIVE —
Ten years from now, this is what’s left.
Every week becomes a Sunday issue. Every month a bound volume. Every year a chapter. Browse them like back issues — searchable, exportable, yours.
— THE ADEOLA ALMANAC · VOL. III · NO. 17 —
The Week of April 14
DELIVERED SUNDAY · 6:00 AM
“Halcyon closed before sunrise. The streak held through travel. Marcus is overdue — and the savings rate dipped below your own bar.”
— 173 ISSUES · 4 BOUND VOLUMES · ONE LIFE, READABLE —
— MANIFESTO —
You are not a to-do list.
You are an enterprise.
Every ambitious person eventually realizes the same thing: you are running a business whether you acknowledge it or not. The business of your career. Of your health. Of the people you love. Of the future you are building.
And most of us run it on scraps — Notes app confessions, a spreadsheet for the savings, a Whoop for the body, Linear for the work, a therapist for the weather inside. None of them talk to each other. None of them see the whole picture.
Obelisk is the whole picture. A single editorial surface where your domains earn scores, your rituals compound, your relationships stay tended, and a thoughtful AI narrates the story only you are authorized to edit.
Treat your life like the company it already is.
— A NOTE ON FIT —
Obelisk is not for everyone.
If you want…
- A to-do app with checkboxes and dopamine.
- Streak shame and red badges to “keep you honest.”
- Templates to copy from someone else’s life.
- Push notifications, growth loops, gamified XP.
- To never write a single sentence about yourself.
- A system that hides your data behind a paywall to leave.
— There are better products for that. We mean it.
If you want…
- One editorial surface that respects your seriousness.
- An AI that knows your numbers and tells you the truth.
- An archive thick with what you actually did.
- To compose a life, not optimize one.
- Quiet. Restraint. The dignity of a real ritual.
- A system you’ll still be using in 2036.
— Then welcome. This was made for you.
— THE DEPARTMENTS —
Seven modules. One composite score.
01
State of the Union
A living front page. Composite index, department scores, CEO priorities, mood, and a morning briefing written just for you.
73 composite
02
Business
Every company, every initiative, every deal. MRR, runway, pipeline, and the path to your ARR target — without a spreadsheet.
$51.9K MRR
03
Health & Wellness
Readiness, consistency, macros, mood. A year of your body on one page — the rituals that build it and the days you missed.
82 readiness
04
Wealth
Net worth, allocation, path to financial independence. Log transactions in one line; watch the arc bend.
$487K net
05
Career
Your mission, your OKRs, your decade-long trajectory. Sliders that feel like steering a ship.
3 OKRs live
06
Relationships
Inner circle, work, mentors, friends. Gentle flags for the people you haven’t spoken to in too long.
27 tended
07
The Vision
A ten-year board. The north star written in your own words, and every milestone plotted between here and there.
2035 horizon
— YOUR CHIEF OF STAFF —
An AI who reads your life
like a seasoned advisor reads
a P&L.
Ask it anything. “How am I doing?” “Should I raise?” “Why am I off pace?” It knows your numbers, your calendar, your north star. And when you need it to, it will argue with you.
01.
Daily briefing. Three paragraphs waiting every morning — what's bright, what needs attention, today's one thing.
02.
Agentic actions. “Log a $42 Uber.” “Add task: draft Q2 review.” It does it. No forms.
03.
Argue mode. Flip a toggle. Get the blunt challenger you need when you’re about to rationalize.
04.
Sunday digest. One tap. Wins, lessons, what to stop, the next three.
YOU · 7:42 AM
Should I take the meeting with Meridian?
OBELISK · 7:42 AM
Meridian is a $120K commitment against your Q2 focus OKR, which is at 41%. You have three conversations like this queued and one overdue with Marcus — who’s actually moving Layered. Take Marcus. Decline Meridian until MRR clears $75K.
YOU · 7:43 AM
Argue with me. I think I should take it.
OBELISK · ARGUE MODE · 7:43 AM
You said “focus” was the word for this quarter. Three weeks in, you’re entertaining a deal that isn’t focus. That’s not a meeting request. That’s a test of whether you meant it. I think you didn’t.
— HOUSE PRINCIPLES —
I.
One surface, not ten.
Your life is not a stack of SaaS tabs. Obelisk collapses the ten things you check every morning into one page you’ll actually open.
II.
Editorial, not industrial.
No dark-pattern streaks, no dopamine pings. This looks like a magazine because your life deserves to be read like one.
III.
Composite over metrics.
A single number that tells the truth. Beneath it, the story. Beneath that, the levers.
IV.
Agentic, not automated.
Talk to Obelisk the way you’d talk to a chief of staff. It logs, asks, pushes back, and leaves you in charge.
V.
Yours, end to end.
No ads. No training on your life. Export any time. Close the file when you’re done.
VI.
Built to be kept.
Ten years from now, this archive is the proof. Of what you did. Of what you became.
— FROM THE FOUNDING EDITION —
“I ran my company on dashboards and my life on vibes. Now I run both on Obelisk. The compound effect is real.
“The Sunday digest changed my marriage. Somehow. Read it together every week now.
“Argue mode is the best $20 I’ve ever spent. It told me to kill a product line. It was right.
— THE STACK YOU’LL RETIRE —
Ten tools. One Obelisk.
YOUR CURRENT STACK
OBELISK
Business numbers
Stripe + Linear + spreadsheet
Built in
Health & body
Whoop + Oura + a journal
One readiness score
Money & net worth
Mint + spreadsheet + dread
One-line ledger
OKRs & career
Notion doc · last edited 2024
Quarterly + decade view
Relationships
Memory · guilt · screenshots
Inner circle, gently flagged
Reflection
Day One · used 14× last year
Daily morning page
Weekly review
A vague Sunday feeling
Auto-generated digest
Synthesis
— · nothing talks to anything
A composite. A verdict.
AI advisor
ChatGPT Plus · therapy · coach
Chief of Staff, built in
Visual integrity
Ten different design languages
One editorial surface
Monthly cost
$112 / mo
$20 / mo · or free
— YOUR FIRST 30 DAYS —
What changes, and when.
DAY 01
The setup.
Three minutes of opinionated questions. Your Obelisk seeds itself with five domains, your north star, your numbers.
DAY 03
First briefing.
Your Chief of Staff publishes its first morning page. Three paragraphs, written in your voice, about your week.
DAY 07
First Sunday digest.
One page. Wins, shadows, the next three. The ritual that quietly replaces the Sunday-night dread.
DAY 14
First lever moves.
A domain score climbs. You feel the compound. You stop opening the other tabs.
DAY 30
First archive entry.
A bound month — yours forever. The book of your life has its first chapter. You are running the company on purpose.
— FROM THE EDITOR —
A note on why this exists.
VOL. I · ISSUE 01 · DESK OF THE FOUNDER
I built Obelisk because I was tired of running my company on dashboards and my life on vibes. Tired of the Sunday spiral where I’d open ten tabs, none of them talking to each other, and close them with no verdict.
The premise is simple: you are already running a company — your life. You deserve a chief of staff. You deserve a front page. You deserve an archive thick with what you actually did.
Obelisk is not a productivity app. It’s the surface I wished existed when I was 28 and pretending Notes.app was a system. It’s the surface I’ll be using in 2036, looking back at the issue I’m publishing today.
— Adeola, founder · New York, April 2026
— READER QUESTIONS —
The objections, answered.
Q.Is this just another Notion template?
No. Notion is a blank page; Obelisk is an opinionated system. The composite, the morning page, the agentic chief of staff, the auto-generated Sunday digest — none of these exist in Notion without you building them. We did. Once. For all of us.
Q.Where does my data live? Are you training on it?
Free tier: local-first, on your device. Daily Edition: end-to-end encrypted cloud sync. We never train on your data. Export everything as Markdown + JSON in one click. Close the file when you’re done.
Q.What if I miss a day? A week? A month?
Then you missed it. Obelisk does not punish you. No streak shame, no red badges, no notifications guilt-tripping you back. It waits. The archive is honest about gaps; that is part of the point.
Q.Will this work if I’m not a founder?
Yes. Operators, creatives, makers, parents, athletes — anyone running a serious life. The “Business” domain becomes whatever you do for a living; the rest is human. Half our founding members aren’t running companies.
Q.Can my partner or co-founder see it?
On your terms. Daily Edition supports shared “issues” — pick exactly which sections a partner sees. Most couples share the Sunday digest; very few share the journal.
Q.What if I cancel?
You keep your archive. Forever. Cancel and the Daily Edition reverts to Weekly — all your past data is still there, still readable, still exportable. We don’t hold archives hostage.
Q.Why $20? Why not $5?
Because we don’t run ads, don’t sell data, don’t optimize for engagement. $20 is what it costs to run a thoughtful AI advisor on your numbers, every day, and still pay rent in New York. The Founding 500 lock that price for life.
30
DAYS
— THE STANDING OFFER —
Try it for thirty days.
If it doesn’t earn its $20, we refund it.
Begin the Daily Edition today. Publish thirty issues. Run thirty briefings. Hold one Sunday digest in your hands. If the surface hasn’t earned its keep — write us a sentence and we send the $20 back. You keep the archive either way.
— SUBSCRIPTION —
Two editions. One archive.
WEEKLY EDITION
$0/ forever
- All seven modules
- Composite index + department scores
- Journal + weekly review
- One theme · Editorial Obelisk
- 10 Chief of Staff messages / month
- Local storage only
FOUNDING 500 · 317 CLAIMED
DAILY EDITION
$20/ monthwas $40
- Everything in Weekly
- Unlimited Chief of Staff + argue mode
- Daily AI briefing + Sunday digest
- All four themes + custom accents
- Auto-seeded starter content
- Cloud sync across devices
- Ten-year archive + PDF export
- Lifetime price lock · founding members only
30-DAY UNCONDITIONAL · KEEP YOUR ARCHIVE EITHER WAY
Ten years from now,
there will be a book.
A year-by-year account of what you built, what you healed, who you loved, what you learned. It will be thick, and it will be true. You start writing it today.
Begin your Obelisk →— ISSUE ZERO —
Not ready? Read the founding edition.
A monthly letter from the editor’s desk — on running your life like a serious thing, composite scoring, ritual design, and what we’re building next. No pitch. No spam.
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