Your taxes shouldn't be a once-a-year surprise.
Find opportunities to reduce your taxes before you make your next financial move. Upload three years of returns and see every structure you could run, priced five years out.1
Helmsman is a tax strategy platform, not a preparer. It doesn't file returns.
Projected five-year reduction2
Helmsman goes deeper than a year-end review, pricing every structure you could run across five years, with the tax math run in deterministic calculators, and the code sections its ranked strategy options cite checked against our citation store.3
Illustrative example
"I've built these structures for twenty years. This is the first tool that shows me the five-year cost of not doing it."4
K. Eames
Managing partner, four-entity practice
code sections in our citation store. Code section and regulation citations in your ranked strategy options and written analysis are checked against it, and any that fail are removed.3
years priced on every path, because an election doesn't settle in one.
The Tax Map
Every structure you could run, ranked and priced.
Seven candidates modeled against three years of filed returns. Open any one.
Management S-corp over operating entity
A management entity above the operating company moves owner compensation to a defensible level while preserving enough W-2 wages at the operating layer to keep your §199A deduction outside the wage limitation.5
Assumes owner services stay full-time and comparable-role compensation holds within 8% of the 2025 survey range.
Partnership with special allocation
Converting the operating entity to a partnership permits allocations that follow the economic arrangement rather than pro-rata ownership, provided they carry substantial economic effect.6
Schedule K-1 reports guaranteed payments with no corresponding line on the 1065. Confirm before this candidate is priced.
Compensation reset, structure unchanged
The smallest change available. Reset officer compensation to a figure supported by comparable-role data, with no new entity and no election to file.7
Can't be combined with the management S-corp. Both lower W-2 wages, which tightens the §199A wage limitation.
C-corp accumulation on retained earnings
Holding earnings inside a C corporation defers the shareholder-level tax, at the cost of accumulated earnings exposure once retained amounts exceed the reasonable needs of the business.8
Ranked fourth despite the deferral, because accumulated earnings exposure is unpriced without a documented business need.
Rental regrouped as a single activity
Grouping the rental with the operating business as one activity changes whether losses are passive, which changes whether they're usable this year or suspended.9
Helmsman won't price this as achieved until participation hours are substantiated. The figure assumes they are.
Your structure, before and after.
The same entities, rearranged. The figures are what the rearrangement is worth across five years.2
| Tax year | Current structure | Recommended | Difference |
|---|---|---|---|
| 2027 | $341,200 | $287,400 | −$53,800 |
| 2028 | $336,800 | $281,900 | −$54,900 |
| 2029 | $335,400 | $279,600 | −$55,800 |
| 2030 | $334,100 | $282,300 | −$51,800 |
| 2031 | $336,800 | $281,400 | −$55,400 |
| Five-year total | $1,684,300 | $1,412,600 | −$271,700 |
These don't stack. Candidates 1 and 3 both lower W-2 wages paid by the operating entity, which tightens the §199A(b)(2)(B) wage limitation. Run together they return $47,200 less than the sum of the two, so Helmsman prices them as alternatives rather than additions.
How it works
Three rules decide what you're allowed to see.
Tax math runs in deterministic calculators
Tax math runs in deterministic calculators with unit tests behind them. Language models read your documents and explain results.
Citations are checked before you see them
Each code section and regulation cited in your ranked strategy options and written analysis is checked against our citation store, and any that fail are removed. The check confirms the provision exists. It does not judge whether the provision supports the strategy.
Missing facts get a question, not a guess
Where your return is silent, Helmsman asks. Answering honestly never produces a quieter report than skipping the question would have.
What our AI provider receives where our readers find the name. A name they miss is sent as written.
Your return is the most sensitive document you own. Helmsman treats it that way.
Identity comes out before analysis goes in.
We remove Social Security and employer ID numbers, account numbers, and street addresses written the usual way, and we swap the names printed on your return for placeholders, before any of it reaches our AI provider. Your names go back in before anything is saved or shown to you. On a library of real filed returns we measured this against, the large majority of printed names, around 98 in 100 in our measurement, were replaced. Roughly one document in seven still had a mention go through, so we will not tell you names never reach the provider.
Your documents never train an AI model.
Analysis runs under commercial API terms that prohibit training on your data. What Helmsman reads stays Helmsman's obligation, not a model's memory.
Isolated per user.
Row-level security with a tested isolation check, so no account can reach another's documents. Logs are shaped to exclude sensitive values.
Delete means delete.
Remove your returns after your Tax Map is delivered. Deletion sweeps storage, database rows and derived artifacts together.
Never public. Never sold.
§7216 consent governs every use of your return information. Nothing is shared for advertising, resale or any purpose you didn't agree to.
FAQs
Does Helmsman file my taxes?
No. Helmsman is a tax strategy platform, not a preparer. It reads returns that have already been filed and tells you what to change before the next one. Your CPA still prepares and files.
Do I still need my accountant?
Yes, and the output is built for that. Every recommended action names who performs it, you or your CPA, and carries the statutory basis so your CPA can evaluate it rather than take it on faith. Several candidates can't be executed without one.
Where do the dollar figures come from?
Deterministic calculators with unit tests, running against figures extracted from your returns. Models read documents and write explanations.
What if my return doesn't contain something you need?
Helmsman raises the question rather than assuming a value. Candidates that depend on an unanswered question are marked as such and aren't priced as achieved. Two open questions is a normal result on a first pass.
Who is this built for?
Owners with more than one entity. An S-corp and a holding company, a partnership interest, rental property in a state that doesn't conform, a spouse with separate income. If you have one W-2 and take the standard deduction, Helmsman will tell you on the first screen that there's nothing here for you.
Is my data secure?
Before your return reaches our AI provider we remove the identifiers and replace the names printed on it with placeholders, and we put your names back before anything is stored or shown to you. On the tax documents we measured, that caught around 98 in 100 name mentions. It is best-effort, not a guarantee.
Know what to do before the year decides for you.
Upload three years of returns. Get a ranked Tax Map with the five-year price of every path.
Notes and authority
- 1. All figures shown are illustrative, drawn from a representative multi-entity return. Your results depend entirely on your own facts. Helmsman provides software analysis, not tax, legal, or accounting advice.
- 2. Five-year projection holds federal rates at current law through 2031. State layer modeled under California R&TC including the §17942 LLC fee.
- 3. The number of Internal Revenue Code sections in Helmsman's citation store, with text from the United States Code as prepared by the Office of the Law Revision Counsel. Each code section or Treasury regulation cited in a ranked strategy option, and in the written analysis when one is produced, must be in the store, with the cited subsection in its text for at least one of the years the analysis covers, or it is removed (in written text, with the sentence that cites it). Regulations come from the eCFR and stand only when cited alone, as Treas. Reg. §, Temp. Treas. Reg. § or 26 C.F.R. § followed by the section number. The check confirms that a provision exists; it does not judge whether the provision supports the strategy. The citations in these notes are our own; the store does not check them.
- 4. Illustrative testimonial for demonstration purposes, not a real customer. It will be replaced with a real, consented customer before launch.
- 5. IRC §1361(b), §162(a)(1), §199A(b)(2)(B); Rev. Rul. 74-44; Watson v. Commissioner, 668 F.3d 1008 (8th Cir. 2012). Related-party fees reviewed under §482.
- 6. IRC §704(b) and the substantial economic effect regulations thereunder.
- 7. IRC §3121(d)(1); Rev. Rul. 74-44. The reject zone is near-zero salary against full-time services, not a fixed percentage floor.
- 8. IRC §531 and §537, accumulated earnings tax and reasonable needs of the business.
- 9. IRC §469(c)(7) and the material participation regulations.