See your whole tax year before it arrives.
Your income doesn't arrive on a schedule, but your quarterly taxes do. Dividends land unevenly, distributions surprise you in December, business revenue swings month to month, and the IRS still expects four clean payments a year. Most people find out what they owe when it's too late to change it.
Investment income, projected with precision
Headwaters connects to your brokerage accounts and forecasts dividends, interest, capital gains, and distributions, broken down by account type and tax treatment. Qualified vs. ordinary, taxable vs. tax-advantaged, short-term vs. long-term: you see exactly how each dollar will be taxed.
Business income, brought into the same view
Link your business accounts and invoicing to fold self-employment income into the picture. Headwaters tracks revenue, estimates self-employment tax, and accounts for deductions so your projections reflect what you'll actually keep.
Tax planning that stays a step ahead
With a full-year forecast in front of you, quarterly estimates stop being guesswork. Headwaters calculates each payment, flags safe-harbor thresholds, and surfaces planning moves, harvesting losses, timing distributions, adjusting withholding, while there's still time to act.
Never be surprised by a tax bill again.
Start your free forecast in minutesHow Headwaters Works
Create your account and set up your tax profile
Tell Headwaters the basics of your tax profile: filing status, home state, dependents, and what forms of taxable income you have. If you have last year's return handy, upload it or enter a few key figures. Headwaters uses them to set your safe-harbor target so you know the minimum you need to pay to avoid penalties.
Connect your brokerage accounts
This is where the investment income forecast comes to life. Link your brokerage, retirement, and cash accounts through our secure connection partner, the same bank-level, read-only technology trusted by major financial apps. Headwaters can never move money or place trades; it only reads balances and holdings.
Once connected, Headwaters automatically:
- Pulls in your current holdings and recent income history
- Identifies each position's income type: qualified dividends, ordinary dividends, interest, and capital gains distributions
- Recognizes each account's tax treatment: taxable, tax-deferred (Traditional IRA/401k), or tax-free (Roth)
Support for major brokerages including Fidelity, Schwab, Vanguard, and more. Prefer not to link an account? You can add holdings manually and get the same projections.
Add your business income
Connect your business bank account or invoicing platform, or enter income directly. Headwaters folds in self-employment revenue, estimates your self-employment tax, and factors in the deductions and expenses that reduce what you actually owe.
Review your live forecast
Headwaters projects your full-year income and tax liability: dividends, interest, distributions, and business earnings, each broken out by how it's taxed. You'll see your expected total bill, what you owe by quarter, and how each account contributes.
Plan and pay your quarterly taxes
For each quarter, Headwaters calculates your estimated payment and reminds you before the deadline. It flags when you've hit your safe-harbor threshold and surfaces planning moves while they still matter: harvesting losses, timing a distribution, or adjusting withholding.
Stay current automatically
Your forecast updates as new dividends post, trades settle, and business income arrives. No spreadsheets to maintain. Open Headwaters any time to see exactly where you stand.
Our Story
Why we built Headwaters.
By any conventional metric, I was doing well. Years of work and investing had built income from a few different directions, and it had grown into something I was proud of.
But every quarter, the same thing happened. I'd realize a tax payment was due, scramble to come up with the number, and never feel sure it was right. Always reactive, always last-minute, always a guess.
Here's what I wish I'd understood sooner: this isn't just a problem for people with big portfolios. If you expect to owe $1,000 or morethat isn't already covered by withholding, the IRS generally expects you to pay throughout the year, not just in April. That's a low bar, and it catches a lot of business owners, freelancers, and investors off guard.
I tried spreadsheets, but they're static, and income isn't. So, I brought together a team, including a world-class engineer, and we built Headwaters to take the guesswork out of forecasting income and taxes.
Whether your money comes from a portfolio, a business, a side hustle, or all of the above, Headwaters lets you forecast your income as it actually happens and see a clear picture of what you'll owe. Avoid IRS penalties, overpayments, and surprise interest charges, and stay in control of your taxes all year long.
Know your income stream.
Built for everyone with income the IRS doesn't withhold.