HELM vs Tiller. Where the spreadsheet-graduate path ends.

Tiller and HELM share more philosophy than either shares with Mint or Empower. Both honor "your data is yours." Both attract the operator who has outgrown a generic dashboard. The split is on a single architectural question: does the tool ever need your brokerage credentials? Tiller's answer is yes (via Yodlee). HELM's answer is no. Everything downstream — pricing, specialization, breach surface, workflow cadence — flows from that one decision.

What Tiller actually does — said plainly

Tiller is a service that automatically pulls transactions and balances from your linked financial institutions into a Google Sheet or Excel workbook of your own. The user-facing surface is the spreadsheet itself; Tiller's templates lay down columns, formulas, and dashboards over the synced data. The flow is: link your accounts via Yodlee → Tiller refreshes daily → your sheet updates → you do whatever spreadsheet-native analysis you want on top. Pricing is around $79 per year, which is part of the appeal.

Why Tiller earned its loyal audience: spreadsheet-graduates love the property that their data lives in their sheet, not in someone's app database. If Tiller closes tomorrow, the sheet is still in the user's Drive. The categorization is tweakable. The templates are forkable. None of that is true of Mint or Empower, which keep the data behind their UI walls. Tiller is a meaningful improvement on that whole class of tool.

But the credential question doesn't disappear. To get the auto-sync, Tiller routes through Yodlee — the same kind of aggregator middleware as Plaid or MX. Your brokerage username and password (or, where supported, a long-lived OAuth token) flow into Yodlee's servers and are stored encrypted there, with a persistent connection that lets Yodlee log back in to your accounts on a regular cadence. The data sovereignty story is real on Tiller's side; the credential-vault story is on Yodlee's side, and that's the part most users don't see when they read the marketing copy.

Where HELM differs — the architectural side

HELM is manual-first. You enter your holdings yourself, in a structured form. There is no Plaid, no Yodlee, no MX, no Finicity in our infrastructure — those vendors are not in our subprocessor list because we never use them. We don't ask for your brokerage username, your password, or any session-equivalent credential. The trade is direct: you give up daily auto-sync, you gain a clean answer to "what does an attacker get if you breach the database tomorrow." (We published the full database inventory if you want to see it explicitly.)

The cost of this architecture is real and we'll name it: real-time balances after market close — the thing aggregator tools lead with — is not a thing HELM does. The values you see in HELM are values you entered, plus an optional public-API price refresh for liquid securities (which only requires the ticker symbol and never your account). For operators who check quarterly rather than daily, this is a feature; for operators who genuinely need an hour-by-hour read on their net worth, Tiller (or its aggregator-using cousins) is a better tool. Pick the cadence that matches the decisions you actually make.

Where HELM differs — the specialization side

Tiller is general-purpose: net worth, budgeting, debt tracking, retirement runway, all in spreadsheet form. The specialization comes from the templates the community has built over the years. Power users layer their own analysis on top.

HELM is specialized for tax-aware portfolio decisions and multi-decade planning. Specifically:

• Tax Brain — wash-sale detection across every brokerage you've entered (Rev. Rul. 2008-5), tax-loss harvesting opportunities, RMD calendars, IRA contribution tracking, QSBS §1202 clock with full worked examples, AMT/ISO modeling. None of that is template-able in a spreadsheet without weeks of CPA-grade tax-code work, and most operators end up paying their CPA $500/hour for the analysis their spreadsheet can't do.
• Monte Carlo cash-flow simulator — 10,000-run sequence-of-returns probability surface for FI scenarios. Box-Muller normal sampling. P10 / P50 / P90 paths shown explicitly. Uses your manually-entered starting net worth, contribution rate, withdrawal rate, and assumed return distribution. The full math is documented in pillar #6.
• Scenario builder — saved what-if scenarios with named inputs (ISO exercise dates, asset sales, contribution changes) and the resulting projection. Versioned. Comparable side-by-side.
• Document Vault — encrypted-at-rest storage for tax letters, estate documents, account-opening confirmations. Per-account encryption key. Optional; most operators upload nothing, which is also fine.
• Ask HELM — an in-app advisor specialized in tax code and FI math. Saved chat threads. Always ends in a CPA-disclaimer because we are software, not advisors.

None of this is in Tiller, by design. Tiller is a great spreadsheet tool. HELM is a specialized analytical app for the operator who has hit the limit of what a spreadsheet alone can do.

Direct comparison — feature by feature

The honest pricing argument

HELM Founding is roughly 12× the price of Tiller. We're not going to dance around that. Here's the math we'd run if we were the operator deciding:

If you're at $250K net worth and the question is "do I want my transactions in a sheet," Tiller is almost certainly the right answer. The marginal value of HELM's tax + Monte Carlo + scenario depth probably doesn't justify the price gap at that scale. Use Tiller; come back to HELM if your portfolio compounds into the seven figures with multiple accounts and equity-comp complexity.

If you're at $2M+ with five-plus accounts, vesting equity, ISO/QSBS exposure, and a CPA you pay $500/hour to think about wash sales for you, the calculus inverts fast. One avoided wash-sale disallowance on a five-figure loss pays for HELM for a decade. One QSBS §1202 clock that you actually track instead of forgetting protects up to $10M of gains from federal tax. The Founding price is set so that a single substantive Tax Brain insight covers the lifetime cost of the subscription, and most operators in this NW band hit that threshold inside the first quarter.

Tiller doesn't need to compete on that margin. We don't need to win every operator. The two tools sit at different points on the curve, and the operator's job is to know which point of the curve they're on.

The migration path most operators take

A surprising number of HELM founding-operator conversations start with "I've been on Tiller for three years and I love it, but I keep building the same wash-sale checker / QSBS tracker / Monte Carlo simulator from scratch every quarter and I'm tired of maintaining the formulas." That's the natural graduation point. We don't see this as competing with Tiller — Tiller is the tool that taught these operators what spreadsheet-grade ownership feels like. HELM is what you graduate to when the spreadsheet stops scaling.

Most graduated operators run both, by the way. They keep their Tiller sheet for daily transaction visibility (Tiller's strength), and they re-enter their structured holdings into HELM quarterly for the analytical work (HELM's strength). The two coexist productively because they're solving different problems on different cadences.

What we'd tell you if you asked us "should I switch"

Switch from Tiller to HELM if all three of these are true:

• Your net worth is $1M+ and at least 60% of it is in liquid investment accounts (the kind where wash-sale, harvest, and AMT calculations actually matter)
• You have at least one of: vesting RSUs/ISOs, multi-state tax exposure, QSBS-eligible equity, an inherited IRA with RMD obligations, or a CPA bill above $3K/year
• You've been running a Google Sheet to do quarterly tax + portfolio analysis and you're tired of maintaining it

If even one of those isn't true, stay on Tiller — you'll get more value per dollar there. We don't want operators on HELM who'd be better served by Tiller; the founding-25 cohort is sized for fit, not for filling.