DIY Bookkeeping with AI

--- ## Who this is for You are a solo founder doing $0-$30K MRR who dreads bookkeeping. Currently paying $300-$500/mo for Bench or Pilot, or winging it with a spreadsheet. Want a system that works for under $30/mo. If you do $50K+ MRR or have complex multi-entity setup, hire a CPA. If you sell physical products with inventory, this book is too thin. ## What you'll have after reading - [ ] 12-line chart of accounts - [ ] 30-minute monthly close checklist - [ ] AI categorizer system prompt - [ ] Receipt capture pipeline - [ ] 13-week cash forecast template - [ ] CPA handoff document - [ ] 1099 / contractor checklist - [ ] The $30K MRR trigger to upgrade --- # Chapter 1 — The DIY bookkeeping stack Below $30K MRR, you don't need Bench. You need a 12-line chart of accounts, a free spreadsheet, and Claude. ## The 2026 data - Below $30K MRR, DIY stack (Claude/ChatGPT + spreadsheet) beats managed services. Source: https://agentmodeai.com/operators/ai-bookkeeping-for-solo-founders/ - Above $30K MRR, Bench ($249/mo) or Pilot ($500/mo) starts to make sense. - QuickBooks Live + Xero Hubdoc offer AI categorization but still require monthly review. ## The 12-line chart of accounts Save in `templates/14-diy-bookkeeping-with-ai-templates/01-chart-of-accounts.md`: | # | Account | Type | |---|---|---| | 1 | Revenue | Income | | 2 | COGS | Cost of goods | | 3 | Marketing | Expense | | 4 | Software / SaaS | Expense | | 5 | Contractors | Expense | | 6 | Salaries | Expense | | 7 | Rent / Office | Expense | | 8 | Travel | Expense | | 9 | Meals (with attendees) | Expense | | 10 | Bank fees | Expense | | 11 | Taxes | Expense | | 12 | Other | Expense | This covers 90% of solo founder transactions. ## Do this in the next 48 hours 1. Set up the chart of accounts in your spreadsheet. 2. Connect Plaid or Wave to your bank. --- # Chapter 2 — The 30-minute monthly close Once a month. Same day. Same time. ## The checklist Save in `templates/14-diy-bookkeeping-with-ai-templates/02-monthly-close-checklist.md`: | Time | Activity | |---|---| | 0:00-0:05 | Reconcile bank feeds | | 0:05-0:15 | Run AI categorizer, review flagged | | 0:15-0:25 | Generate P&L, cash position | | 0:25-0:30 | Tax check + reserve | ## Do this in the next 48 hours 1. Block 1 hour on your calendar for the first close. 2. Run the checklist. --- # Chapter 3 — AI categorization The 95%+ automation. ## The system prompt Save in `templates/14-diy-bookkeeping-with-ai-templates/03-ai-categorizer-prompt.md`: ``` You are categorizing transactions for a small B2B SaaS business. Transaction: {{merchant}} | {{amount}} | {{date}} | {{description}} Categories (use exactly these): - Revenue: Stripe payouts, MRR, annual subscriptions - COGS: hosting, API costs, contractors (project-specific) - Marketing: ads, content, sponsorships - Software: SaaS subscriptions under $500/mo - Travel: flights, hotels, meals (with attendees) - Office: rent, utilities, supplies - Taxes: sales tax, income tax, payroll tax - Other: anything that doesn't fit Output: CATEGORY: [category] CONFIDENCE: [0-1] NOTES: [1-sentence rationale] ``` ## Do this in the next 48 hours 1. Test on 10 historical transactions. 2. Verify accuracy >90%. 3. Run on all current transactions. --- # Chapter 4 — Receipt capture The photo → CSV pipeline. ## The tools - Veryfi free tier (limited receipts) - Taggun ($50/mo for unlimited) - Or: just photograph + manually enter in spreadsheet ## The CSV template Save in `templates/14-diy-bookkeeping-with-ai-templates/04-receipt-csv-template.md`: ```csv date,merchant,amount,category,notes 2026-06-01,Stripe,$1245.00,Revenue,Monthly payouts ``` ## Do this in the next 48 hours 1. Photograph 5 receipts. 2. Enter in CSV. 3. Test the categorization. --- # Chapter 5 — The 13-week cash forecast The most useful forecast for solopreneurs. ## The template Save in `templates/14-diy-bookkeeping-with-ai-templates/05-13-week-cash-forecast.md`: ``` Week | Inflows | Outflows | Net | Cumulative 1 | $X | $X | $X | $X ... ``` ## The AI prompt ``` Given historical inflows and outflows, project next 13 weeks. Flag weeks where cumulative cash drops below 2 months of expenses. ``` ## Do this in the next 48 hours 1. Pull last 3 months of transactions. 2. Build the forecast. --- # Chapter 6 — Tax readiness Quarterly. Don't skip. ## The quarterly checklist Save in `templates/14-diy-bookkeeping-with-ai-templates/08-quarterly-tax-checklist.md`: | Quarter | Due date | |---|---| | Q1 | April 15 | | Q2 | June 15 | | Q3 | September 15 | | Q4 | January 15 (next year) | Tax owed: 25-30% of net profit (federal + state + SE). ## Do this in the next 48 hours 1. Calculate quarterly tax. 2. Set aside in a separate account. --- # Chapter 7 — The CPA handoff Quarterly. Save in `templates/14-diy-bookkeeping-with-ai-templates/06-cpa-handoff-doc.md`: ```markdown Quarter: Q[X] [Year] Business: [name] Total revenue: $X Total expenses: $X Net profit: $X Top 10 expenses: 1. [Merchant] — $X 2. ... Flagged transactions (resolved): [list] Flagged transactions (unresolved): [list] Bank reconciliation status: [reconciled / discrepancies] Questions for CPA: 1. ___ 2. ___ Tax payments made: $X Estimated tax due next quarter: $X ``` ## Do this in the next 48 hours 1. Schedule the quarterly call with your CPA. 2. Send the handoff doc 1 week before. --- # Chapter 8 — When to hire a CPA / Bench The decision rule. **Stay DIY if:** - <$30K MRR - <5 contractors/yr - <3 states of operation - Simple entity **Hire a CPA if:** - >$30K MRR - >$100K revenue (audit risk) - Multi-state - Multi-entity - International - Stock options Save in `templates/14-diy-bookkeeping-with-ai-templates/10-when-to-hire-cpa.md`. ## Do this in the next 48 hours 1. Identify your current stage. 2. Set the trigger for upgrading. --- # Appendix A — Template pack Templates in `/home/hermes/workspace/unloopd/books/14-diy-bookkeeping-with-ai-templates/`: - `01-chart-of-accounts.md` - `02-monthly-close-checklist.md` - `03-ai-categorizer-prompt.md` - `04-receipt-csv-template.md` - `05-13-week-cash-forecast.md` - `06-cpa-handoff-doc.md` - `07-1099-checklist.md` - `08-quarterly-tax-checklist.md` - `09-flagged-transaction-log.md` - `10-when-to-hire-cpa.md` # Appendix B — Tool stack ## Free - Wave, Xero Hubdoc, ChatGPT free, Claude free, Sheets ## Paid - Bench $249/mo — once you cross $30K MRR - Pilot $500/mo — for >$100K MRR - Xero Starter $13/mo - Veryfi $50/mo # Appendix C — 30-day implementation roadmap | Day | Deliverable | |---|---| | 1-7 | Chart of accounts + bank feed | | 8-14 | AI categorizer setup | | 15-21 | First monthly close | | 22-30 | Cash forecast + tax check | # Appendix D — Glossary - **COGS** — Cost of Goods Sold. - **EIN** — Employer Identification Number. - **LLC** — Limited Liability Company. - **P&L** — Profit and Loss statement. - **SE TAX** — Self-Employment Tax. - **TIN** — Tax Identification Number. # Appendix E — Further reading 1. *Bookkeeping for Solopreneurs* — $20. 2. *QuickBooks for Dummies* — $25. 3. AgentMode.ai bookkeeping — https://agentmodeai.com/operators/ai-bookkeeping-for-solo-founders/ --- ## Related Unloopd books These complement this one — read them next to round out your playbook: - **[AI E-Commerce Operator](https://unloopd.com/books/ecommerce-ai-operator)** — every e-commerce operator needs the DIY bookkeeping playbook — the numbers are the difference between profit and burn. - **[The 1-Person Agent Team](https://unloopd.com/books/agent-team-solo)** — an agent team can run the bookkeeping pipeline, but you still need the framework from this book. - **[Pricing & Packaging AI Services](https://unloopd.com/books/pricing-packaging-ai-services)** — the pricing playbook assumes you know your margin — the DIY bookkeeping gives you that number. [Browse the full catalog →](https://unloopd.com/books) # Appendix F — About Unloopd Unloopd publishes short, operational books for solo founders. — The Unloopd editors