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 track your income, run the SE tax + bracket math, and ping you 14 days before each deadline. 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
Every transaction flips between business and personal with a tap. Deductions flow into the tax tracker. Personal flows into your budget. The math just works.
Future you, with variable income
FIRE projections that handle 1099 spikes, SEP-IRA limits, and 'what if I take 6 months off after launch' scenarios.
Tax vault built for tax season
1099s, receipts, mileage logs, prior returns — all categorized to IRS schema, all year-round. At year-end, export a CPA-ready package in one click.
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.
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 bank linking, no time limit
WealthWise Pro
For solopreneurs running their own thing
or $99/year (save 31%)
- Everything in Free, with no message limit
- AI advisor that knows you're self-employed
- Quarterly tax tracker (auto deadlines)
- Receipt → deduction AI scanner
- Business / personal one-tap toggle
- Document AI for contracts + invoices
- CPA export package (year-end zip + PDF)
- Bank linking via Teller (coming Q3)
14-day free trial · No credit card
WealthWise Studio
For partner businesses + power users
or $149/year (save 31%)
Up to 4 partner / collaborator accounts
- Everything in Pro
- Up to 4 partner / collaborator accounts
- Multi-business support (multiple LLCs / projects)
- Monte Carlo retirement modeling
- Advanced tax-optimization AI
- 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 | Teller (soon) | |||
| 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.