Become An Unpredictable Strategist

Never let a mofo box you in.

”I’m a fucking walking paradox, no I’m not”

Tyler, the Creator, Yonkers (2011)

”To be or not to be?”

William Shakespeare, Hamlet (1599)

Rap lyrics. Shakespeare.

Don’t ever let a motherfucker box you in. 

When I first started writing online, a friend with 40k followers told me “If you want to grow online, be funny or be serious. Don’t do both”.

I chose to ignore him.

I post funny shit, I post serious shit, you never know what I’m hitting you with.

My job is keeping mofos on their tippy-toes

I didn’t ignore his advice just because I love keeping people on their toes (although I do get a certain high from it). It’s more than that.

I have a thesis that being both funny and serious on social media is more authentic than exclusively being funny or exclusively being serious. And the more authentic and real of a person you are, the more friends you make, the more money you make, the more fun you have — because people are attracted to authenticity like a magnet. People can sniff out fake people on social media like drug dogs smelling Charlie Sheen flying into LAX from a Las Vegas bender. Funny people can be serious, serious people can be funny.

Don’t ever let a motherfucker box you in or know what to expect.

  • Yes I’m a cyberpunk startup capitalist type guy, but I also have my yoga teaching license.

  • Yes I read tech essays by Paul Graham and Balaji Srinivasan, but I also have a quote by hippie poet Allen Ginsberg tattooed on my leg.

  • Yes I make funny memes, but I make serious moolah.

I’m a walking contradiction. I’m hard to explain to people. This makes me happy — I’ve escaped job descriptions and made more money last month than ever in my life. People can be multiple things. We are multi-faceted. Funny people can be serious, serious people can be funny. Don’t ever let a motherfucker box you in.

F. Scott Fitzgerald famously said the sign of intelligence is being able to hold two contradictory ideas in your head at the same time.

I say it’s being the walking contradiction itself.

Be unpredictable in your content and business.

Your content should be unpredictable.

Your business strategy should be unpredictable.

Your marketing stunts should be extra unpredictable.

The second you become predictable, you lose. Your competitors know what’s coming and can beat you. Your audience knows what’s coming and is bored.

“Keep others in suspended terror: cultivate an air of unpredictability,” writes Robert Greene in the 48 Laws of Power. “Nothing is more terrifying than the sudden and unpredictable.”

Over the last 3 years, newsletter startup Beehiiv has dominated the incumbent giant ConvertKit not by attacking them with insults, but by shipping surprise new app features every week. Users like me are excited every single week for new features; meanwhile competitors are freaking the fuck out. They’ve kept ConvertKit and other competitors in “suspended terror”.

“New features loading.” No 3 words have ever shaken competitors to their core more “If you find yourself outnumbered or cornered, throw in a series of unpredictable moves,” writes Greene. “Your enemies will be so confused that they will pull back or make a tactical blunder.” Beehiiv is now at $800K MRR and ConvertKit announced they’re changing their name to Kit (useless brand name changes are never a good sign... what you running from bro???).

The only way to become unpredictable…

Ironically the only way to become unpredictable is to strategize beforehand and make predictions on what will happen when you make moves.

Playing chess and moving random pieces with no strategy doesn’t make you a smart unpredictable strategist, it makes you a moron. The same is true for making content or running a startup. The more you quietly strategize beforehand, the more unpredictable you appear to be. The only reason a skill like writing looks effortless is because a person worked really hard on it, the same is true with a well-crafted content/business strategy.

This is why I’m bearish on a lot of the “Build In Public” movement.

For those unfamiliar, it’s the idea of sharing your struggles, successes, and even roadmap and revenue numbers in public (the whole point of being a private company is to move in private, building in public is for public companies.). Ok, great share your struggles and successes to teach people and build a following, but don’t go telling people your roadmap and revenue breakdowns. The element of surprise and secrecy is too valuable of a competitive advantage to give away.

Sit down alone, turn off your phone, grab a notebook, and write down the key elements of your strategy. Then don’t tell anyone. Shut up and execute.

unpredictable robert greene content strategy surprise marketing

Become an Unpredictable Strategist.

How I can help:

I work with startups/VCs in 3 main ways:

😈 Strategy: Get access to my strategy calls, extra Silicon Valley growth hacks, strategy templates, and more here.

✏️ Ghostwriting: If you’re a founder looking to grow your X, LinkedIn, or newsletter and ready to invest $5k/mo, book a call here.

😂 Memes: Want to go viral with dank memes? Join 1000s of memelords and get my book and course here.

Memes of the Week:


me at parties

Want to go viral with memes?

Get access to the only course that’ll show you:

  1. How to use free software to make dank memes FAST

  2. How to use memes to sell products on Twitter and LinkedIn at scale to thousands of people using automation 🤑

  3. How to build your own personal meme database and workshop to save you time browsing the internet

PLUS: get access to an exclusive interview with a memelord and startup founder who made $3 MILLION from memes on Twitter.

Thanks for reading nerds.

Create some cool shit this week.

Jason “The Memelord” Levin

Head of Growth @ Product Hunt, Author of Memes Make Millions

1  I still grew my social accounts and bank accounts. Meanwhile that friend has quit posting on social media (probably because he was bored from being so stuffy and serious all the time).