What Entrepreneurs Can Learn from On Writing
Priya sat at her kitchen table at midnight, scrolling through her pitch deck for the fourth time. Slide six read: "We leverage a synergistic, paradigm-shifting approach to unlock latent market value." She'd written it to sound impressive to the investors she was meeting in nine hours. Reading it now, cold and tired, she couldn't say what her company actually did. She opened a blank slide and typed one plain sentence instead: "We help small clinics bill insurance correctly the first time." It felt too simple to be worth a fundraising round. But it was the first sentence all week that told the truth about her business, and it was the one she kept.
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.
0 of 5 selected
The core lessons, applied to you
Strip your pitch and updates down to honest, plain language
Founders pad decks and emails with words like "disruptive," "robust," and "best-in-class" because the vocabulary of ambition feels safer than plain description. The result is a slide that could describe ten different companies and describes none of them well. Investors skim past it, and customers stop reading the value proposition halfway through.
Take your last pitch deck or cold email and rewrite every headline as one sentence a stranger could repeat back correctly. Delete every adjective that doesn't change what the reader does next, and replace every vague verb — "leverage," "utilize," "enable" — with the specific action your product actually performs.
Protect a consistent time to write investor and customer updates
A founder only sends investor updates when there's good news to spin, so backers hear nothing during the hard quarter and then get a suspiciously upbeat email the moment things turn around. Trust erodes quietly, and nobody says why.
Put a recurring 45-minute block on your calendar — same day, same time, every week or month — for a short, honest update, written whether the news is good, bad, or boring. The consistency itself becomes part of the message: this founder tells us the truth on a schedule, not just when it's convenient.
Read other people's business writing as craft education
Founders read competitors' pitches for strategy but never for sentence-level craft, so their own decks quietly absorb the same tired phrases everyone else is already using, and nobody in the room notices the resemblance.
Collect five investor updates or landing pages you find genuinely compelling and five that make you want to close the tab. Mark the exact sentence where each one earned or lost your attention, then check your own last update against that list before you send it.
Your founding story is material, but craft decides if it lands
The rocky pivot, the year the runway nearly ran out, the customer who almost walked — these are legitimate, powerful material for how you talk about your company. But raw honesty about hard experience does not automatically move an investor or a customer; only clear, specific, well-edited sentences do that. The discipline you apply to your numbers slide has to apply to your story slide too, or the story reads as either oversharing or spin instead of evidence.
Protected writing time and plain language both take patience, but a hot lead or an anxious investor sometimes needs a reply in minutes, not after your Friday writing block. Don't let the deadline become an excuse for jargon — a fast email can still be a plain one. Reserve your protected block for the writing that shapes how people see your company, and let urgency shorten your sentences rather than cloud them.
Name one thing, honestly
Which piece of writing you plan to send this week would most benefit from cutting every word that isn't doing real work?
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
0 of 3 selected
Run this for seven days
Collect five investor updates or landing pages you find genuinely compelling and five that make you want to close the tab. Mark the exact sentence where each one earned or lost your attention, then check your own last update against that list before you send it.