Variable income. Quarterly taxes. Business and personal money tangled together. WealthWise OS is the AI financial OS for the people who run their own thing.
Friday · May 7
Good evening, Rocky.
Projected Freedom Number
$847,293
Savings Rate
28.4%
Emergency Runway
8.4mo
Real Return (after-tax)
7.2%
FIRE Projection · 7.2% real return
Goals
3 active- Emergency Fund92%
- Roth IRA 202678%
- Travel · Japan 202745%
Recent Activity
View all- +$1,400.00
VTI · Auto-invest
Brokerage
- −$2,340.00
Rent · May
Housing
- +$84.20
Dividend · VXUS
Brokerage
Features
Seven things no other app does.
Monarch was built for W-2 employees. QuickBooks Self-Employed was built for bookkeepers. ChatGPT can't see your bank account. WealthWise OS was built for the way you actually live.
AI advisor that knows you're self-employed
Ask 'should I take a distribution this month?' and get a specific answer based on your real income, your tax situation, and your retirement goals. Not generic advice - your numbers.
"YTD I've billed $112K. Should I max my SEP-IRA or take a Q4 distribution?"
"Max your SEP first. At $112K net SE income, you can contribute up to $20.8K - drops you from the 24% bracket to 22%, saves ~$4,576 in federal tax. Distribution can wait until January."
Quarterly tax math, automatic
We read your income, run the SE tax + bracket math, and flag each deadline as due 14 days out. No more guessing what to send the IRS.
Receipt-to-deduction in 30 seconds
Snap a receipt. AI extracts vendor, amount, and IRS deduction category - and shows you the tax savings in dollars.
Business / personal, one tap
Tag every receipt Business, Personal or Mixed, with a percentage for shared costs like your phone. Business and mixed deductions flow straight into the quarterly tax tracker.
Future you, from your real budget
A FIRE calculator that starts from your actual budget, and an AI advisor that plans with this year's SEP-IRA and Solo 401(k) limits.
Tax vault built for tax season
1099s, receipts, contracts and prior returns in one encrypted vault, sorted by AI into tax, receipt, loan and legal folders, all year-round. Download any document the moment your preparer asks.
Document AI for contracts and invoices
Drop a contract, statement of work, or 1099. AI extracts the key terms, flags concerns, and adds the data to your forecast in seconds.
Direct bank linking.
Read-only access.
Your bank, your control.
Live via Teller - the same direct-integration platform several major fintechs use. Your bank login happens inside Teller's secure iframe; we never see your password. Mutually-authenticated TLS to your bank, read-only access, revocable any time from your Banking page.
Pinned client cert, encrypted in flight
All major banks and brokerages
We can see balances. We cannot move money.
One click in /banking ends the connection
Sign in required. CSV import and manual entry are also supported.
Pricing
Priced like a tool you pay for.
No ads. No data sales. No upselling you to financial products. Just a tool you pay for, run forever, and own your data.
Free
For self-employed people getting started
- AI advisor (20 messages / month)
- Manual transaction entry
- Budget, debt, FIRE calculators
- Vision board for goals
- CSV import + export
- No time limit
WealthWise Pro
For solopreneurs running their own thing
or $99/year (save 31%)
- Everything in Free, plus 1,000 AI messages / month
- AI advisor that knows you're self-employed
- Quarterly tax tracker (auto deadlines)
- Receipt → deduction AI scanner
- Business / personal / mixed split on every receipt
- Document AI for contracts + invoices
- PDF wealth reports
- Bank linking via Teller (live, read-only)
14-day free trial · No credit card
WealthWise Studio
For partners, households + power users
or $149/year (save 31%)
Adds Family Mode for shared finances
- Everything in Pro, plus 2,500 AI messages / month
- Family Mode: add partners + family members
- Split shared expenses, see who owes what
- Combined household net worth
- Priority support (24-hour response)
- Early access to new features
Founder's Lifetime - $249
One-time payment. All Pro features forever. Built by a solopreneur who hates recurring bills as much as you do.
Compare
One of these is built for you.
We compared WealthWise against the three tools self-employed people actually try. Here's what each one does - and doesn't - do.
| Feature | WealthWiseOS | MonarchMoney | QuickBooksSelf-Employed | ChatGPT/ Claude |
|---|---|---|---|---|
| Built for self-employed | Bookkeeping | |||
| AI advisor on YOUR finances | Limited | Manual entry | ||
| Quarterly tax math, automatic | Hallucinates | |||
| Receipt-to-deduction AI | Categorize only | |||
| Business + personal in one app | ||||
| FIRE / future projections | Manual | |||
| Document AI for contracts | Per-chat only | |||
| Bank account aggregation | ||||
| Annual price | $99 | $99 | $180 | $240 (Plus) |
WealthWise is built around the assumption that you run your own thing. Monarch assumes you have a W-2. QuickBooks assumes you want to be an accountant. ChatGPT can't see your bank account. We're the only one designed for the way self-employed people actually live.
Support
Everything you need to know about WealthWise OS. Can't find what you're looking for? Reach out to our team.
Popular topics
One AI financial OS for everything self-employed life throws at you. Variable income, quarterly taxes, business deductions, FIRE projections - all in one place. Free to start.