What Entrepreneurs Can Learn from On Writing Well
Priya stared at the investor update she'd drafted the night before a board call. It opened with a sentence about the company's "strategic pivot toward a more holistically integrated go-to-market paradigm," and reading it back, she wasn't sure what she'd meant by it herself. She'd spent forty minutes on that paragraph, reaching for bigger words each time it felt thin, as if vocabulary could stand in for a clear story about why revenue had slipped. Her cofounder read it over her shoulder and asked the plain question: did they lose the deal or not? She didn't have a ready answer, because she hadn't actually decided one. She deleted the paragraph, wrote one blunt sentence about what happened, and only then saw how much of the update had been built to avoid saying anything she'd have to defend. The board call started in twenty minutes.
The whole book, compressed
This edition works through 4 core lessons — take them one at a time, not all at once.
What's different for your conditions
Tap whichever ones sound like you. Nothing here is sent or saved — it's just for your own noticing.
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The core lessons, applied to you
Clutter is the enemy in your fundraising materials
A founder pads a pitch deck with phrases like "best-in-class," "synergistic," and "disruptive paradigm shift" because the terms feel like the price of admission in the category. An investor skims past three slides before finding the one sentence that says what the company actually does. The jargon was meant to sound impressive; instead it delays the moment the reader understands the business at all. Practice: Before sending any deck or update, run one pass looking only for inflated words — swap "leverage" for "use," "utilize" for "use," "ecosystem" for the actual list of partners or customers you mean. Read the result aloud; if a sentence doesn't sound like something you'd say to a friend over coffee, clutter is still hiding in it.
Before sending any deck or update, run one pass looking only for inflated words — swap "leverage" for "use," "utilize" for "use," "ecosystem" for the actual list of partners or customers you mean. Read the result aloud; if a sentence doesn't sound like something you'd say to a friend over coffee, clutter is still hiding in it.
Clarity of writing requires clarity of thought about your own business
A founder writes a paragraph about "improving engagement across the funnel" without having settled what counts as an engaged user, so the sentence sounds confident while meaning almost nothing. A board member asks a direct follow-up question and the founder realizes, mid-answer, that the metric was never actually defined. Practice: Before writing any sentence about company performance, first write the plainest possible version of the claim — one number, one definition, one cause — in a private note. If you cannot state it plainly there, the business idea isn't ready to be written up for anyone else yet.
Before writing any sentence about company performance, first write the plainest possible version of the claim — one number, one definition, one cause — in a private note. If you cannot state it plainly there, the business idea isn't ready to be written up for anyone else yet.
Revise ruthlessly, even against a deadline
A founder writes a customer-facing announcement in one sitting an hour before it's due and sends the first draft because there's no time left to fix it. The email reads exactly like what it was — a first attempt — with three ideas competing for the reader's attention in the opening line. Practice: Build a fifteen-minute cutting pass into your writing schedule as a non-negotiable step, not an optional polish. Read the draft once looking only for sentences and clauses that repeat something already said, and delete them without mercy before you allow yourself to send it.
Build a fifteen-minute cutting pass into your writing schedule as a non-negotiable step, not an optional polish. Read the draft once looking only for sentences and clauses that repeat something already said, and delete them without mercy before you allow yourself to send it.
Personality survives simplicity in founder writing
Once the jargon and throat-clearing are gone, what's left in a founder's writing is usually the most honest version of how they think and talk — direct, informal, sometimes funny under pressure. Investors and early employees are choosing to trust a person as much as a plan, and plain sentences let that person come through instead of hiding behind borrowed corporate style. Simplicity doesn't flatten a founder's voice; it's usually what lets the voice be heard at all.
Cutting clutter takes time, and time is scarce, so ruthless revision can look like a luxury when someone is waiting on a reply. Protect revision time for anything with real stakes attached — the update, the pricing email — and accept a rougher first pass on lower-stakes internal notes, rather than pretending everything deserves equal polish.
Name one thing, honestly
Where in your own writing this month did you reach for an impressive word or phrase instead of doing the harder work of deciding exactly what you meant?
Good. Now look back at the "Try this" line under whichever lesson feels most connected to what you just wrote, and treat that as this week's actual assignment — not all 4 at once.
The practices from this edition
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Run this for seven days
Build a fifteen-minute cutting pass into your writing schedule as a non-negotiable step, not an optional polish. Read the draft once looking only for sentences and clauses that repeat something already said, and delete them without mercy before you allow yourself to send it.