Questions, answered.

In your private PilePilot account, hosted on our infrastructure. Your books live in a per-account workspace that is isolated from other customers, encrypted in transit, and never sold, shared, or used to train public AI models. When the AI categorizes a transaction, only that line (vendor, amount, date) is sent to the AI provider — never your full statements in bulk.

You stay in control: export any workspace whenever you want, and delete your account and all of its data at any time. Your books are never pooled with other customers' data.

You keep them. At any point you can export every workspace as a complete, portable archive in one click. Canceling just stops the billing — you don't lose your data.

If you come back later, your workspaces are right where you left them — no re-import, no migration, no fees.

When you use AI features, the relevant transaction lines, receipts, bank statements, or tax-return uploads may be sent to the Anthropic API for categorization, OCR, extraction, or summarization. That's how the AI works. Anthropic does not train on API traffic by default — that's their published policy. Processing is scoped to one client at a time, and PilePilot stores the structured result in that client's account.

If you have a tax-firm client who needs total air-gap (zero AI calls), you can run PilePilot's hard-rules engine only — categorization will be slower and less accurate, but the AI never gets called.

Not yet — we're a brand-new product and we don't claim certifications we haven't earned. We follow security best practices today: encryption in transit, per-account data isolation, least-privilege access, error monitoring, durable hosted storage, and anytime data export. We plan to pursue formal SOC 2 in the second half of 2026.

Tax data isn't covered by HIPAA. For GDPR — if you're an EU customer, we honor access, export, and deletion requests and never sell or share your data. Just don't email sensitive files to hello@pilepilot.com in plain text.

We take security seriously because your books are in your account. We reduce risk with encryption in transit, per-account isolation, least-privilege access, error monitoring, and durable hosted storage — and we never sell or share your data. If we ever detected a breach, we would notify affected customers promptly, and you can export or delete your data at any time.

Once your books are categorized, PilePilot looks at the shape of your numbers — income, entity type, profit, payroll, dependents, real estate, retirement balances — and walks the 71-strategy library against your profile. Every strategy carries a qualifier checklist (e.g. "do you own a property used >14 days/yr personally?" for STR loophole, "is your profit >$80K?" for S-corp election). Only strategies you actually qualify for surface, ranked by estimated annual savings.

Each pick comes with the IRC citation, a step-by-step implementation tracker (with due dates and dependencies), and a plain-English audit-risk score. The scan re-runs every time the books change — close out a quarter, get a fresh plan.

Software. Pile Pilot LLC is a software company that surfaces strategies, runs qualifier checklists, and tracks implementation steps. It does not file your return, sign your workpaper, or replace your own tax professional's judgment. The footer disclaimer says it plainly: the output does not constitute professional tax, legal, or financial advice.

Assisted software support starts at $99 and helps organize the workpapers. For actual advice, review the output with your own qualified professional before you act on it.

TurboTax is a tax filer. You type your 1099s and W-2s in, it asks you wizard questions, it e-files. It does almost nothing with your books — and it has zero opinion on whether you should have elected S-corp last March, started a Solo 401(k) in September, or run a cost segregation study on the duplex you bought.

PilePilot starts with the books. It reads your bank statements, builds tax-ready self-prep workpapers, then runs a strategy scan against the finished numbers and tells you what moves were available — most of which had to be decided before year-end. TurboTax shows up at the finish line. PilePilot shows up during the year, when the strategy moves are still on the table. You can absolutely use both: PilePilot for books and workpapers, TurboTax for the e-file.

No. Every strategy in the library is IRC-cited and the qualifier checklist is the guardrail. If you don't actually qualify for a strategy, you don't see it. We don't surface conservation easements, micro-captive insurance, listed transactions, or anything the IRS has flagged on the Dirty Dozen. The library is legal, defensible moves — Augusta Rule, S-corp election, Solo 401(k), HSA, Section 179, cost segregation, QSBS, Opportunity Zones, R&D credit — with audit-risk scores so you go in eyes open.

If a strategy is borderline (e.g. Hire Your Kids on a service business), PilePilot says so on the page: what the documentation requirement is, what kills the deduction, and what the IRS has audited in recent years. The whole point is to give you the same defensible playbook a $5K–$50K planning engagement would — without the shelters.

Built and shipping today: Books agent (full categorization, P&L, Schedule C, S-corp workpaper, 1099 review, balance sheet, liability center, payroll reader, cash expenses, inventory templates, IRS RAG, vendor learning, multi-client cockpit, magic-link client portals, voice chat).

Coming through 2026: Biller (Stripe invoicing) in Sprint 1, Poster (social posting) in Sprint 2, Replier (email drafts) in Sprint 3, Scheduler (booking + reminders) in Sprint 4. Each sprint is ~6 weeks. Founding users get every new agent at the same locked-in price.

Today: Windows (one-click installer ready, used in a real small business) and macOS (terminal-launch). We're planning a polished macOS installer for late 2026. Linux works too if you're comfortable running a Flask app — the codebase is plain Python 3.10+.

Fair question. The differentiation is in three places: (1) the IRS RAG over actual publication text means citations on every line, which a vanilla chatbot can't give you; (2) the vendor-learning pipeline compounds every category override, so your firm gets faster over time; (3) the multi-agent architecture means Books, Biller, Poster, Replier, and Scheduler share data — your invoice goes into the P&L the moment it's paid, which a single-tool agent can't pull off.

If all you want is to ask ChatGPT to categorize one statement, you can. We did. It misses ~30% of edge cases (intercompany transfers, owner draws, accrued payroll), and it never cites. PilePilot exists because the gap between "ChatGPT can do this" and "I can defend this to the IRS" is the whole product.

Yes. The majority of users are one-person businesses doing their own books, not tax pros. The product is designed so a barber, a plumber, a photographer, a creator can use it without needing to know what Schedule C Line 17 is. You snap the statement, the AI does the work, and you get a P&L you can hand to your tax preparer (or e-file yourself).

The firm-side is a separate product surface — same engine, different UI. If you ever decide to bring in a tax professional, they can plug into your existing PilePilot workspace and pick up your books in five minutes.

Email hello@pilepilot.com. During beta, the PilePilot team answers every email — usually within 24 hours, often faster. Once we scale past the founding 250, support tiers will track the subscription plan, but the founding-user response time stays locked in too.