How to Write Killer Headlines Like Andrew Chen: 21 CopyWriting Do’s and Dont’s

andrew-chen If you want to see great web copy, read Andrew Chen. I’m going to show you his top 15 posts from last year. What do you see? The headlines are very compelling; smart little nuggets that draw you in. The secret is how he combines several copywriting techniques so well. It looks seamless. And that’s what makes it so great.

What Andrew Chen Can Teach You About Writing Killer Headlines

Let’s look at the first seven. Remember, Andrew writes about business models, design and metrics. Not very sexy. But, armed with the right attitude…

1. How to create a profitable Freemium startup (spreadsheet model included!)

Includes Freemium (good keyword) and adds the spreadsheet teaser. How many headlines have you seen include offers in brackets?

2. Built to Fail: How companies like Google, IDEO, and 37signals build failure-tolerant systems for anything!

Nice twist on Built to Last, the best-seller business book.

3. Free to Freemium: 5 lessons learned from

Squeezes two killer keywords, uses a number to grab attention, lessons learned implies that there will be some benefit for you the reader into the same headline

4. Product design debt versus Technical debt

Product design Technical debt. Four short words, nice and punchy.

5. Friends versus Followers: Twitter’s elegant design for grouping contacts

Do you see a pattern emerging here? Andrew counterbalances popular keywords (Twitter) against Friends and Followers. Also, ‘versus’ implies conflict or tension. A nice way to stir the reader’s emotions.

6. 5 warning signs: Does A/B testing lead to crappy products?

Crappy isn’t seen in too many headlines. When’s the last time you saw it?

7. Freemium business model case study: AdultFriendFinder ARPU, churn, and conversion rates

The 7th most popular article has 13 words, including several acronyms, all flying in the face of convention wisdom.

FYI Andrew is here

Those are the first seven on his list. Here’s the rest.

8. Which startup’s collapse will end the Web 2.0 era?

9. 2009 conference schedule for the digital media industry

10. Does every startup need a Steve Jobs?

My Fav!

11. Why low-fidelity prototyping kicks butt for customer-driven design

12. What if interviews poorly predict job performance? What if dating poorly predicts marital happiness?

13. How to calculate cost-per-acquisition for startups relying on freemium, subscription, or virtual items biz models

14. 5 crucial stages in designing your viral loop

15. Age (and ARPPU) ain’t nothing but a number: Data on how age impacts social gaming monetization

Over to you

What do you think of these headings? It’s not PC, it’s not the ‘correct’ way – but I think it works?

Does it work for you?