You earn more than ever.
Do you know where you stand?
SirHENRY watches your money so you always know three things: where you stand, what you can afford, and what to do next — every number computed from your data, with the math shown.
HENRY — High Earner, Not Rich Yet
Your money got more complex.
Your tools didn't.
You earn $150K, $300K, maybe $500K. You're maximizing your career, but between taxes, retirement, investments, and the decisions that compound over decades — you need tools as sophisticated as the problems you're solving.
36%
of $250K+ earners report living paycheck to paycheck
High income isn’t the same as knowing where you stand. The money moves — the picture never resolves.
PYMNTS / LendingClub survey, 2022
41%
of DIY investors skip an advisor because they think they don’t have enough money to qualify
The #1 reason isn’t cost — it’s believing you’re not eligible. You are exactly who this was built for.
YouGov, June 2026
1%+
is what advisors typically charge on portfolios under $1M — a higher rate than bigger clients pay
Advisory fees average 100–120bps below $1M versus 80–100bps above $2M. The smaller the portfolio, the higher the rate — and flat-fee advice starts around $2,400/yr.
Kitces Research, 2025
How it works
From chaos to clarity in three steps.
No spreadsheets. No guesswork. Just connect your data and let Sir HENRY do the heavy lifting.
Connect
Link accounts at 12,000+ institutions via Plaid, upload tax docs, or enter data manually. About 10 minutes, once.
Retirement readiness
1,000 Monte Carlo scenarios · P10–P90 bands
Analyze
Sir HENRY runs the numbers — Monte Carlo retirement scenarios, tax strategies, spending patterns, and 13 proactive insight types.
Act
Get prioritized action items with real dollar impact, tailored to your actual financial picture — not generic advice.
Your AI financial analyst
SirHENRY works for you.
Not a chatbot. A financial engine woven through every part of your financial life — connected to your banks, your market positions, your tax data. Sir HENRY doesn't wait for questions. It finds opportunities, flags risks, and tells you what to do next.
12,000+ Accounts
Banks, brokerages, cards — synced via Plaid
Investment Intelligence
Portfolio tracking, equity comp, real-time market data
Proactive Insights
Finds savings, opportunities & risks before you ask
Tax Strategy Engine
Roth conversions, TLH, deductions, AMT planning
Life & Goal Planning
Home, education, household, what-if modeling
Retirement Simulator
Monte Carlo projections, Social Security, scenarios
12,000+
institutions connected
13
proactive insight types
100%
local-first — your data lives on your device
Retirement
See your future, clearly.
Not a vague estimate — a probability. Sir HENRY runs thousands of market scenarios against your real accounts and spending.
- 1,000 Monte Carlo market scenarios per projection
- Three confidence bands — see the range, not a single line
- Retirement budget, Social Security, and what-if scenarios
Tax strategy
Keep more of what you earn.
The strategies wealth managers charge for — surfaced automatically from your own numbers, before deadlines pass.
- Backdoor Roth and conversion opportunities, detected
- Tax-loss harvesting candidates from your actual holdings
- AMT, deduction bunching, and equity-comp timing
Investing
Every holding. Every account. One picture.
Brokerage, 401(k), IRA, RSUs — unified into a single allocation view with the risks called out, not buried.
- Allocation and drift across all your accounts
- Concentration risk flagged before it bites
- Equity comp and vesting alongside your portfolio
Privacy by design
Local-first. Not cloud-first.
Most financial apps upload everything to the cloud. Sir HENRY is a desktop application — your financial database lives in a local file on your machine, not in a centralized data warehouse.
Stored on your device
- Your financial database (SQLite, on disk)
- Transactions, balances, and holdings
- Your stored tax documents and AI conversation history
- Encryption keys for your local data
The short list that touches our servers
- Waitlist email and account sign-in (Supabase)
- AI queries (Anthropic) — de-identified for transaction analysis
- Imported tax and pay documents, including the page image (Anthropic)
- Optional hosted bank connections (Plaid relay)*
*Honest footnote: if you connect a bank through our hosted Plaid relay, the connection token and the account data it retrieves pass through servers we operate (encrypted with a per-user key). Prefer strictly on-device? Use the local connection path. Full details in our Privacy Policy.
The full picture, one place.
Everything you need to build wealth — in a single, private workspace.
Intelligence
Sir HENRY AI
Ask anything about your finances. Get answers grounded in your actual numbers, not generic advice.
Dashboard
Net worth, savings rate, retirement readiness, and proactive action items — updated in real time.
Insights
AI-generated alerts on spending anomalies, optimization opportunities, and risks you haven’t noticed.
Planning & Investing
Retirement
Monte Carlo simulations, confidence bands, multiple scenarios, and a retirement-specific budget.
Portfolio
Every holding across every account. Allocation analysis, concentration risk, drift tracking.
Equity Comp
RSUs, stock options, vesting calendar, AMT calculator, and tax-scenario tools for tech comp.
Money & Taxes
Tax Strategy
Deduction opportunities, tax-loss harvesting, and Roth conversion analysis — walk into your CPA meeting with organized numbers and the right questions.
Cash Flow
Income vs. expenses with monthly trends, seasonal patterns, and year-over-year comparisons.
Goals
Emergency fund, backdoor Roth, down payment, 529 — track every milestone with progress and projections.
Also included: Budget · Recurring · Transactions · Life Planner · Household · Market Pulse · Tax Documents · My Businesses
Sir HENRY is a financial planning tool, not a financial advisor. All projections, estimates, and tax calculations are for educational purposes only and should not be considered personalized financial, tax, or investment advice. Consult a qualified CPA, CFP, or attorney before making financial decisions. Terms · Privacy
Not a budgeting app. Not a robo-advisor.
You've outgrown basic tools. Sir HENRY delivers comprehensive financial planning at a fraction of the cost.
| Capability | Budgeting AppsMonarch, YNAB, Copilot | Robo-AdvisorsBetterment, Wealthfront | Tax SoftwareTurboTax, H&R Block | SirHENRYOne private workspace |
|---|---|---|---|---|
| Unified AI analysis (budget, invest, tax, retire) | ||||
| Retirement projections (Monte Carlo) | ||||
| Holistic tax strategy (Roth, equity, deductions) | ||||
| Equity comp & stock grant planning | ||||
| Life planning & scenario modeling | ||||
| Proactive AI-driven insights & action items | ||||
| Data stored on your device, not our servers | ||||
| Automated investing & rebalancing |
Unified AI analysis (budget, invest, tax, retire)
Retirement projections (Monte Carlo)
Holistic tax strategy (Roth, equity, deductions)
Equity comp & stock grant planning
Life planning & scenario modeling
Proactive AI-driven insights & action items
Data stored on your device, not our servers
Automated investing & rebalancing
Competitor capabilities as of August 2026 and subject to change.
What HENRYs are asking
Millions of high earners. Same questions.
Paraphrased from real discussions in the r/HENRYfinance community — the questions Sir HENRY is built to answer.
“I don’t need someone to manage my money. I need someone to tell me if I’m making the right decisions.”
Software Engineer· paraphrased from r/HENRYfinance
“I wish I could just ask ‘can I afford this house’ and get a real answer based on my numbers.”
Senior Product Manager· paraphrased from r/HENRYfinance
“I don’t want another app that tells me I spent too much on restaurants. I want something that helps me figure out if I should max my 401(k) or pay off loans.”
Attorney· paraphrased from r/HENRYfinance
Your financial future, simplified.
Every account, every projection, every tax move — one private command center. SirHENRY is rolling out to founding members now.
No spam. Just one email when we're ready.
Your financial data is stored on your device, not our servers. No minimums. No credit card required.
