The financial command center
you've been earning.
Retirement projections. Tax strategy. Investment analysis. Proactive insights that find opportunities before you ask. All running privately on your device.
Join the waitlist
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 lack a comprehensive financial plan
Not because they lack discipline — because the right tools didn’t exist yet.
LendingClub, 2024
77%
of high earners want a clear financial roadmap
The question isn’t ‘am I saving enough?’ — it’s ‘am I optimizing across retirement, taxes, and investments?’
Project Henry, 2025
$15K+
per year for an advisor who sees your full picture
Wealth managers require $1M minimums. CFPs charge $5K–$15K/year. Sir HENRY delivers the same depth for a fraction of the cost.
Flat Fee Advisors, 2025
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 takes action.
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
10,000 Monte Carlo runs, Social Security, scenarios
12,000+
institutions connected
13
proactive insight types
100%
local — data never leaves your device
See your future, clearly.
10,000 simulations. Three confidence bands. One clear answer.
Keep more of what you earn.
Backdoor Roth, tax-loss harvesting, and strategies your CPA missed.
Your entire financial life. One screen.
Net worth, savings rate, retirement readiness, spending trajectory, and proactive action items — updated in real time.
Privacy by design
Your data never leaves your device.
Most financial apps upload everything to the cloud. Sir HENRY is a desktop application — your data never touches our servers. It lives on your machine and stays there.
A desktop app, not a web app
Sir HENRY runs natively on your computer. Your financial data lives in a local database — no cloud servers, no shared infrastructure.
We never see your data
Bank balances, transactions, tax documents — none of it passes through our servers. We couldn't access it even if we wanted to.
Encrypted at rest
Plaid tokens and sensitive credentials are encrypted with industry-standard Fernet encryption before touching disk.
No ads. No data sales. Ever.
Your financial data is never monetized, shared with third parties, or used to target you. Our only revenue is your subscription.
The full picture, one place.
Everything you need to build wealth — in a single, private workspace.
Intelligence
Dashboard
Net worth, savings rate, retirement readiness, and proactive action items — updated in real time.
Sir HENRY AI
Ask anything about your finances. Get answers grounded in your actual numbers, not generic advice.
Insights
AI-generated alerts on spending anomalies, optimization opportunities, and risks you haven't noticed.
Money
Cash Flow
Income vs. expenses with monthly trends, seasonal patterns, and year-over-year comparisons.
Budget
AI-assisted monthly planning with smart category targets and forward-looking forecasts.
Recurring
Every subscription and fixed cost in one place. See your total monthly commitments at a glance.
Transactions
Smart categorization that learns your patterns. Search, filter, export — all in seconds.
Planning
Goals
Emergency fund, backdoor Roth, down payment, 529 — track every milestone with progress and projections.
Retirement
Monte Carlo simulations, confidence bands, multiple scenarios, and a retirement-specific budget.
Life Planner
Model major decisions — home purchase, career change, relocation — with your real financial data.
Household
Two incomes, one coordinated strategy across taxes, benefits, insurance, and wealth building.
Investing
Portfolio
Every holding across every account. Allocation analysis, concentration risk, rebalancing signals.
Equity Comp
RSUs, stock options, vesting calendar, AMT calculator, and sell strategy tools for tech comp.
Market Pulse
Real-time watchlist, market indices, crypto prices, and economic indicators — all in one view.
Taxes & Business
Tax Strategy
AI-powered deduction finder, tax-loss harvesting, Roth conversions, and strategies your CPA missed.
Tax Documents
Upload receipts, 1099s, and tax paperwork. AI extracts the numbers and organizes everything.
My Businesses
Track business entities, categorize expenses, monitor revenue, and simplify self-employment taxes.
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, Mint | Robo-AdvisorsBetterment, Wealthfront | Tax SoftwareTurboTax, H&R Block | SirHENRY |
|---|---|---|---|---|
| Unified AI analysis (budget, invest, tax, retire) | ||||
| Retirement projections (Monte Carlo) | ||||
| Holistic tax strategy (Roth, equity, deductions) | ||||
| Equity comp & stock grant planning | ||||
| Household dual-income optimization | ||||
| Life planning & scenario modeling | ||||
| Proactive AI-driven insights & action items | ||||
| Budget tracking & forecasting | ||||
| Portfolio tracking & analysis | ||||
| Automated investing & rebalancing | ||||
| Tax filing & preparation | ||||
| Data stays on your device | ||||
| Mobile app | Soon |
Unified AI analysis (budget, invest, tax, retire)
Retirement projections (Monte Carlo)
Holistic tax strategy (Roth, equity, deductions)
Equity comp & stock grant planning
Household dual-income optimization
Life planning & scenario modeling
Proactive AI-driven insights & action items
Budget tracking & forecasting
Portfolio tracking & analysis
Automated investing & rebalancing
Tax filing & preparation
Data stays on your device
Mobile app
Millions of high earners. Same questions.
Real posts from r/HENRYfinance's 184K+ 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, 31 · 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, 34 · 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, 38 · r/HENRYfinance
Your financial future, simplified.
SirHENRY launches Spring 2026.
No spam. Just one email when we're ready.
Your data never leaves your device. No minimums. No commissions.