Your startup needs an enemy

What to do (and what not to) so your marketing packs a punch

David Sacks, the founder of Yammer and one of the Paypal mafia, wrote an essay last month, an absolute masterclass in thinking about marketing.

Note point number 3: Attack the status quo.

Over to Sacks:

Your startup has an opponent, but it’s not your competitors; it’s some version of the status quo. You need to name this enemy. Marc Benioff convinced the world that software was the enemy. Did Benioff mean all software or just the kind that has to be installed? Presumably the latter — but those are the kinds of details that can be explained once you have someone’s attention. 

At my company Yammer, we identified our enemy as a rigid org chart that trapped information, stifled dissent, and created bureaucracy. Our description evolved, as we were constantly searching for better ways to articulate the problem. Just as we iterated on our product to achieve greater product-market fit, we would iterate on our messaging to achieve greater resonance. The more vividly you describe the need for change, the more obvious the need for your product will become.


Chapter 8 of the Basecamp book Getting Real is called Pick a Fight.

From the chapter:

When we decided to create project management software, we knew Microsoft Project was the gorilla in the room. Instead of fearing the gorilla, we used it as a motivator. We decided Basecamp would be something completely different, the anti-Project.

We realised project management isn’t about charts, graphs, reports and statistics — it’s about communication. It also isn’t about a project manager sitting up high and broadcasting a project plan. It’s about everyone taking responsibility together to make the project work. Our enemy was the Project Management Dictators and the tools they used to crack the whip.

A paragraph later:

One bonus you get from having an enemy is a very clear marketing message. People are stoked by conflict. And they also understand a product by comparing it to others. With a chosen enemy, you’re feeding people a story they want to hear. Not only will they understand your product better and faster, they’ll take sides. And that’s a sure-fire way to get attention and ignite passion.

Does the playbook sound familiar to you, especially in the context of Basecamp?

It does to me.

Because Basecamp very recently used these very ideas to launch and catapult Hey, their new email product, to immediate success. They picked a fight with email in general, in particular attacking Gmail and its stagnation head-on. This gave them great publicity, and people took sides. They didn’t stop there. They picked another fight with Apple on App store guidelines, harvesting even more publicity.

Make no mistake: Every step that led to these confrontations was deliberate. Basecamp wanted the fight. And they got what they wanted from it. From nothing, Hey is now a serious product, a competitor to Superhuman and Gmail.


In a 2013 Fast Company article, Gregory Ciotti of Help Scout (he’s now at Shopify) cites a paper by psychologist Henri Tajfel, which states that one of the main reasons Apple has such a fan following is that they have drawn a line in the sand, and have clearly chosen an enemy for their customers.

Group formation, it would seem, is strengthened enormously when the group has an enemy. If you’ve ever wondered why fans of opposing sports teams (that have never met) can become so antagonistic to their opponents while being so close-knit to fellow fans (that they’ve also never met), this research is your answer.

If you recall Apple’s famous Mac vs. PC ads or its earlier 1984 advertisement, the message is clear: Apple is for hip, young, creative people and the PC is for corporate drones who use their beige boxes for little more than creating Excel spreadsheets.


Remember, the enemy you pick has to be bigger than you.

Always punch up, never down.

The world always roots for the underdog, never for the (perceived) bully.

Zendesk forgot this when they punched down at a little Indian startup called Freshdesk back in 2012.

You should not.


In January this year, I was working on a consulting project with a fintech startup.

Their premise was simple: They would help MSMEs with loans for their GST payments (which is one very specific pain point, especially with the new regulations).
I was tasked with telling a story that would be easy to communicate to the semi-urban and rural Indian MSME audience.

It took me some time, but the enemy I came up with was the moneylender. The character itself has a storied history in literature, most famously William Shakespeare’s Shylock in The Merchant of Venice. This also meant familiarity; we would not have to explain the negative connotation. The faceless moneylender was an abstract enough character so no one could really take offence, and most importantly, it was easy for the product’s audience to understand.

I had picked a fight, and chosen an enemy. And because the character was an abstraction, I had punched up, at the status quo, not down.

Alas, we couldn’t get to the finish line with this, though. The startup pivoted, and then the pandemic struck. But I always tell this story as the one campaign of mine which I would’ve loved to see go live.