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FinanceWill Guidara

The Rule of 95/5

Manage 95% of spending like a maniac so you've earned the right to spend the last 5% foolishly.

Difficulty
Moderate
Time to result
~ongoing to results
Steps
5
Confidence
85%

The Rule of 95/5 is a budgeting discipline: track and scrutinize 95% of every dollar spent with maniacal rigor — no expense too small to review, any month-over-month drift bigger than 5% gets investigated — specifically so the business has both the cash and the credibility to spend the remaining 5% on generous, unscripted gestures for customers. The 'foolish' spending isn't actually foolish; it's what produces lasting impressions, loyalty, and free word-of-mouth marketing. The rule reframes generosity as a budget line rather than an accident, and treats underspending on it as a cost to future relationships, not a savings.

Origin

Coined by Will Guidara while running Eleven Madison Park, where the accounting team reviewed the books with extreme scrutiny specifically to justify and protect the budget for unscripted guest gestures like free gifts, upgrades, and surprises.

Core principles

  • 01Scrutinizing 95% of expenses is what earns the legitimacy to spend the remaining 5% generously
  • 02Any expense that drifts more than 5% from last month deserves a deep dive, not a shrug
  • 03'Foolish' spending in service of a guest's experience is not actually foolish — it's the highest-return line item most businesses ignore
  • 04Not spending on generosity is its own form of financial recklessness because it forfeits future loyalty

How to run it

  1. 1

    Audit every expense category monthly

    Go through the full set of accounts line by line — no expense is too small to review.

  2. 2

    Investigate any 5% swing

    If any line item moved more than 5% from the previous month, do a deep dive into why before moving on.

    Pro tip Treat the 5% threshold as a trigger, not a target — smaller drifts add up too.

  3. 3

    Earn the surplus before you spend it

    Confirm the business is actually generating the money before allocating any of it to discretionary gestures.

    Watch out Spending generously on a business that isn't actually profitable is what Guidara calls genuinely reckless, not admirable.

  4. 4

    Set aside the 5% for discretionary generosity

    Explicitly allocate a small percentage of the budget for gestures, gifts, or upgrades staff can deploy without pre-approval.

  5. 5

    Track the return in stories, not just ROI

    Measure the impact of the 5% by the stories and loyalty it generates, since the return is real but hard to put a direct number on.

    Watch out Don't kill the program just because it resists a clean ROI calculation — Guidara argues the impact is real even when it's not measurable in the short term.

In the wild

Restaurant accounts scrutinized to fund guest gifts

At Eleven Madison Park, Guidara's team reviewed the entire set of accounts with extreme scrutiny, flagging any 5% month-over-month deviation for a deep dive, which freed up legitimate budget to fund things like the Tiffany champagne glasses and comped courses.

The tight 95% discipline gave the team the financial standing and confidence to spend generously on guest moments without it being reckless.

A UPS store owner's daily comp rule

A UPS store owner in Sarasota, Florida applied a version of the same logic: run the store tightly, but require every register employee to comp one customer's order (up to $30) once per shift.

The single daily discretionary spend transformed the culture of the store and became a differentiator no competitor matched.

Common mistakes

Spending generously without the 95% discipline behind it

Guidara is explicit that you have to 'earn the right' to spend the 5% — generosity funded by a business that isn't actually in control of its costs is reckless, not admirable.

Treating the 5% as unnecessary because it lacks a clean ROI

Because the return on generosity is hard to measure, some businesses cut it first — Guidara argues this is backwards, since it's underspending on the thing that builds long-term loyalty.

Is it for you?

Best for

owners and operators who want to fund memorable, unscripted moments without losing financial control

Not ideal for

businesses already operating on razor-thin or negative margins, where there is no legitimate 5% to allocate

From the transcript

I call it the rule of 95/5... manage every single dollar like an absolute maniac 95% of the time... But you do that so that…

Will Guidara · 31:00

If anything was 5% over from the month before, we would do a deep dive into it.

Will Guidara · 32:00

I really do believe in the long term is being financially reckless [not to spend it].

Will Guidara · 32:30

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