wilson

Tracks finances across multiple business entities with AI-powered classification and per-entity reporting. Trigger when user asks about multi-entity, multiple businesses, separating personal and business expenses, or consolidated financials.

Pre-flight check for 1099 filing requirements. Identifies contractors paid over $600 and validates information completeness. Trigger when user asks about 1099s, contractor payments, or year-end filing prep.

Generates a comprehensive export package for your accountant: P\&L, categorized transactions, tax summaries, and notes. Trigger when user asks about sending data to their accountant or accountant package.

Scores transactions and deduction patterns against known IRS audit risk factors. Flags high-risk items. Trigger when user asks about audit risk, red flags, or IRS scrutiny.

Prepares negotiation briefs for recurring bills with market rate comparisons and scripts. Trigger when user asks about negotiating bills, lowering costs, or getting better rates.

Calculates break-even point based on fixed costs, variable costs, and pricing. Models scenarios. Trigger when user asks about break-even, breakeven analysis, or minimum revenue needed.

Summarizes charitable donations for tax deduction tracking with receipt verification reminders. Trigger when user asks about charitable giving, donations, or philanthropy summary.

Analyzes revenue and expenses by client to determine per-client profitability. Identifies most and least profitable relationships. Trigger when user asks about client profitability, customer ROI, or account analysis.

Builds custom financial reports with user-specified metrics, date ranges, and groupings. Trigger when user asks about custom reports, building a report, or specific report configurations.

Creates debt payoff plans using avalanche or snowball methods. Calculates payoff timelines and interest savings. Trigger when user asks about debt payoff, debt reduction, or paying off loans.

Builds depreciation schedules for business assets using MACRS, straight-line, or Section 179. Trigger when user asks about depreciation, asset tracking, or capital equipment deductions.

Tracks progress toward emergency fund goals based on monthly expenses. Calculates months of coverage. Trigger when user asks about emergency fund, rainy day fund, or savings buffer.

Identifies recurring expenses with optimization opportunities — subscriptions to cancel, plans to downgrade, or bills to renegotiate. Trigger when user asks about optimizing expenses, reducing bills, or subscription audit.

Creates and tracks progress toward financial goals with timelines and required savings rates. Trigger when user asks about financial goals, savings goals, or financial planning targets.

Calculates home office deductions using simplified or actual expense method. Trigger when user asks about home office, workspace deductions, or working from home expenses.

Reviews insurance-related transactions to identify coverage gaps and potential savings opportunities. Trigger when user asks about insurance audit, insurance review, or coverage optimization.

Generates investor-ready financial updates with KPIs, runway, growth metrics, and narrative. Trigger when user asks about investor update, investor report, or board update.

Tracks unpaid invoices and calculates aging buckets (current, 30, 60, 90+ days). Identifies collection priorities. Trigger when user asks about invoice aging, unpaid invoices, accounts receivable, or collections.

Generates lender-ready financial statements for loan applications. Includes income verification and debt-to-income ratios. Trigger when user asks about lender package, loan application, or mortgage documentation.

Detects lifestyle creep by comparing spending growth against income growth over time. Trigger when user asks about lifestyle creep, spending inflation, or why savings aren't growing.

Tracks business mileage for tax deductions. Calculates IRS standard mileage rate deductions and logs trips. Trigger when user asks about mileage, driving deductions, or vehicle expenses.

Guides through a month-end financial close process: reconcile accounts, categorize unknowns, review anomalies, and generate closing reports. Trigger when user asks about month-end close, closing the books, or monthly reconciliation.

Generates a monthly financial digest with key metrics, notable transactions, and trend highlights. Trigger when user asks about monthly summary, monthly digest, or month recap.

Calculates and tracks net worth over time from assets and liabilities. Trigger when user asks about net worth, total assets, or overall financial position.

Imports transactions from PayPal CSV exports. Handles PayPal-specific fields and currency conversions. Trigger when user asks about importing PayPal data or syncing PayPal transactions.

Analyzes costs and margins to suggest optimal pricing. Models price sensitivity scenarios. Trigger when user asks about pricing, margins, markup, or what to charge.

Measures revenue concentration risk across clients or income sources. Calculates dependency metrics and flags dangerous concentrations. Trigger when user asks about revenue concentration, client dependency, or income diversification.

Calculates months of financial runway based on burn rate and cash reserves. Projects fund depletion date. Trigger when user asks about runway, burn rate, cash runway, or how long money will last.

Analyzes transactions to determine sales tax nexus across states. Identifies where economic nexus thresholds may be met. Trigger when user asks about sales tax, nexus, or multi-state tax compliance.

Identifies seasonal spending and revenue patterns from historical transaction data. Forecasts upcoming seasonal shifts. Trigger when user asks about seasonal trends, cyclical patterns, or month-over-month patterns.

Analyzes profitability of side hustles by tracking related income and expenses separately. Trigger when user asks about side hustle profit, freelance income, or gig economy tracking.

Intelligently splits transactions into component parts with category assignment for each piece. Trigger when user asks about splitting transactions, dividing expenses, or itemizing purchases.

Coaches through a spending fast challenge by identifying discretionary spending to cut and tracking daily progress. Trigger when user asks about spending fast, no-spend challenge, or cutting expenses.

Imports transactions from Square CSV exports. Maps Square payment data to Open Accountant format. Trigger when user asks about importing Square data or syncing Square transactions.

Estimates state income tax liability based on income and filing status. Covers all 50 states. Trigger when user asks about state taxes, state income tax, or multi-state tax returns.

Imports transactions from Stripe CSV exports. Maps Stripe payment fields to Open Accountant format. Trigger when user asks about importing Stripe data or syncing Stripe transactions.

Estimates potential underpayment penalties for estimated taxes. Calculates safe harbor thresholds and required quarterly payments. Trigger when user asks about estimated tax penalties, underpayment, or quarterly tax shortfall.

Reconciles Venmo transactions against bank records. Identifies matched and unmatched Venmo payments. Trigger when user asks about Venmo reconciliation or matching Venmo to bank transactions.

Imports transactions from Wise (TransferWise) CSV exports. Handles multi-currency transactions. Trigger when user asks about importing Wise data or syncing Wise transactions.

Builds a zero-based budget where every dollar of income is assigned a job. Trigger when user asks about zero-based budgeting, envelope budgeting, or allocating every dollar.