Design Posts

Entrepreneurs are the best business writers in the world. If you can’t write, you can’t raise money. Or recruit. Or sell.

I don’t know a single great entrepreneur who isn’t a great writer.

Good business writing is clear, compelling and concise. Read Steve Jobs, Elon Musk and Warren Buffett (though they should have used half the words).

Here’s what I send my friends when they ask for writing tips:

  1. Writing is a customer service problem.
  2. Pretend you’re sending an email.
  3. Sum it up in a tweet.
  4. Read it on your phone.
  5. Don’t write your thought process.
  6. Start with a summary.
  7. Writing is rewriting.
  8. Delete half the words.
  9. Avoid adjectives.
  10. Scrutinize every word for bias.
  11. Kill your darlings.
  12. Don’t apologize.
  13. Use persuasion checklists.
  14. Skim Strunk & White.
  15. Break the rules once you learn the rules.
  16. Writing is a design problem.

1. Business writing is a customer service problem. You’re not the star—the reader is. Help them get what they want, as quickly and effectively as possible. They might want to solve a problem. They might want to be persuaded. Give ’em the goods.

2. Pretend you’re sending an email. Or a Slack message. It will calm your mind and yield better writing.

3. Sum it up in a tweet. If the tweet isn’t compelling, the rest isn’t compelling. The ideal tweet absolves the reader from reading further. Sequoia says, “Summarize the company’s business on the back of a business card.”

4. Email it to yourself and read it on your phone. You’ll see the words with fresh eyes, as if someone else wrote them. This will force you to keep it short and simple.

5. Don’t write your thought process. The final draft shouldn’t mimic the path you took to come up with the idea. Instead, start the piece with a conclusion and make your best case.

6. Start with a summary. A good summary absolves the reader from reading further. But they will still want to.

7. Writing is rewriting. Write down your thoughts in a stream of consciousness. Don’t get hung up on diction. Then spend most of your time rewriting and reorganizing—sweat the details. I’m still rewriting posts days after I’ve published them.

8. Delete half the words. Say more with less. That’s good customer service. “If I had more time, I would have written a shorter letter.”

9. Avoid adjectives. Use numbers instead. An adjective is an admission that you don’t know the number.

10. Scrutinize every word for bias and rhetoric. Are they an ‘unruly mob’ or ‘patriots’? Perhaps neither—just call them by their name. Argue the other side of every word, at least to yourself. Learn more about bias.

11. Kill your darlings. Delete beautiful ideas and phrases if they don’t help the customer solve their problem.

12. Don’t apologize. Don’t qualify, apologize or anticipate arguments. Just say it. Some people will never understand that BOCTAOE. You can always put an FAQ at the end.

13. Use persuasion checklists like CLASSR and SUCCES. See the Appendix for details.

14. Skim Strunk & White once in a while. You don’t need to read the whole book at once. Also read The Day You Became a Better Writer.

15. Break the rules once you learn the rules. Write in your authentic voice. Tell a story. Use adjectives. Write poetry. Learn which word choices unlock action. But first learn how to write clearly and concisely.

16. Writing is a design problem. Example: never use the idiom of ‘the former or the latter.’ It forces the reader to go back and figure out what you’re referring to.

Learn design by reading Tufte, A Pattern Language and Don’t Make Me Think. Dieter Rams: “Indifference towards people and the reality in which they live is actually the one and only cardinal sin in design.”


Consider adding a sentence for each of the CLASSR persuasion techniques: commitment, liking, authority, scarcity, social proof and reciprocity. Here’s a joke example by Victor Ghitescu:

“Learn more about CLASSR by reading Influence by Cialdini. Do it because you like books that make you smarter. Do it for me, I’m an expert on this. The world’s best salespeople have all read it. Do it before the whole world finds out about it. You can thank me later.”

Make sure your writing is simple, unexpected, concrete, credible, emotional, stories (SUCCES from Made to Stick):

“I believe that this nation should commit itself to achieving the goal, before this decade is out, of landing a man on the moon and returning him safely to the earth.”

Must be a 1-(wo)man startup.

Must code. Must write good copy.

Must be passionate about solving problems for our customers, not “designing.”

Must fix other people’s designs and front-end code on production (people ship whenever they want).

Must help our 1-(wo)man startups with their design problems. Must force your help on them when needed.

Must take the words of our founders/whomever straight to mocks without worrying about whether we’re going to build it. Make the mocks, then start evaluating the idea. Pivot it when necessary (always).

“Sweat the details and corner cases… Fix the bugs no one else notices.”

– Facebook’s Aaron Sittig at a Design Tech Talk (video)