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Since 2017 · San Francisco · New York · London

Margin of Safety.

A quarterly read on the financial mechanics founders actually sweat — cap tables, runway, board packs, and the unglamorous arithmetic of getting from one round to the next. Written by the senior partners who do the work.

Issue No. 27 Autumn 2025 Editor: Margaret Walsh

— The Four Channels

A curated publication, not a reverse-chronological feed.

Every piece we publish lives in one of four channels — the financial decisions a Series A–C founder or CFO actually loses sleep over. Pick the one that matches your problem this quarter; we'll route you straight to the relevant pieces.

  1. 01

    Cap Table Hygiene

    Dilution math, option-pool top-ups, 409A refreshes, founder vesting resets, and the quiet waterfalls that erode control before a term sheet arrives.

    14 essays
  2. 02

    Runway Math

    Burn multiples, default-alive thresholds, scenario modeling under revenue miss, and the moment to start a process before the board forces your hand.

    11 essays
  3. 03

    Board Pack Design

    What goes on page one, which KPIs survive a skeptical director, narrative structure for bad quarters, and how to retire a slide that no longer earns its place.

    9 essays
  4. 04

    Fundraising Mechanics

    Outreach sequencing, data room construction, dilution modeling under multiple term sheets, and how to read a lead investor's pattern before you sign.

    17 essays

— The Most Recent Six Issues

Recent dispatches from the desk.

The full archive runs deeper than what's here — these are the six most recent pieces, selected by the partners. Subscribe by RSS or browse by channel above.

01

Runway Math · 12 min

The default-alive test: when a missed quarter becomes a fundraise.

A clean formula for the moment a SaaS company stops being able to absorb a revenue miss with existing capital — and the three signals a CFO should watch in the model before the board meeting forces the conversation.

02

Cap Table Hygiene · 9 min

409A refreshes: the one cost founders forget to model.

Stale 409As quietly destroy option-pool economics at the worst possible time — usually mid-process with a term sheet on the table. A practitioner's note on cadence, vendor selection, and what to do if yours is more than fourteen months old.

03

Fundraising Mechanics · 22 min

Reading a lead investor before they read your deck.

Partner add-ons, follow-on history, public board commentary, and the four less-obvious signals that predict whether a fund will actually wire. Includes a one-page diligence checklist our team runs on every prospective lead.

04

Board Pack Design · 7 min

The four slides that should die in every board pack.

A short, opinionated audit of the recurring slides we cut from client packs every quarter — and the replacement slide each one frees up. Useful as a checklist before your next board cycle.

05

Runway Math · 15 min

Burn multiple, burn ratio, and the metric your investors will actually use.

Burn multiple gets cited constantly and understood poorly. We work through three anonymized client models to show what the number actually says about capital efficiency — and what it doesn't.

06

Cap Table Hygiene · 11 min

The post-Series-A option-pool top-up nobody warns you about.

The Series A term sheet almost always includes an option-pool refresh sized against the post-money valuation. The math is straightforward; the negotiating posture is not. A walkthrough of how to model the real dilution before you sign.

A founder who can't explain their burn multiple in one sentence hasn't finished thinking about it yet. Our job — and this publication's job — is to help you finish that sentence before the board meeting does it for you.
Margaret Walsh Founding Partner · Former KPMG Director, Stripe Treasury

— Reader Questions

Things working CFOs and founders ask before they subscribe.

Who actually writes the essays?
Every piece is authored by a named senior partner at the firm — Margaret Walsh, David Walsh, Priya Iyer, James Holloway, or another member of the eighteen-person advisory bench. Nothing is ghostwritten, nothing is farmed out to a content team, and nothing is published under a staff byline. If the name on the post is not the person who did the thinking, we consider that a failure.
How often does a new issue come out?
We publish two long-form essays per month and one quarterly issue index like the one you're reading. There is no fixed publishing calendar designed to feed an algorithm — pieces go out when a partner has something the firm would lose by not saying. Subscribers get an email the morning a piece ships; everyone else can follow via RSS.
Is any of it gated or behind a marketing form?
No. Every essay is open, ungated, and free to read without handing over an email address. We are explicit about this because the alternative — gating a 1,200-word opinion piece behind a "download our buyer's guide" wall — is the exact behavior this publication exists to critique. We do not run pop-ups, we do not run exit overlays, and we do not gate archive content.
Do you actually take clients from people who read this?
Yes, frequently — and we say so openly because pretending otherwise would be dishonest. The work described in these essays is the same work our senior partners do inside client engagements. If a piece resonates with a founder reading it, and the firm has capacity, the natural next step is a thirty-minute diagnostic call. The publication is not bait; it is the firm's actual point of view, written down.