"Surprisingly tall". What a complimentary insult. May explain my failure on dating apps.

Great question: What’s the best complimentary insult you’ve had?

The people who get me jealous of their insights have the highest AHA moments per word.

They take a 1,000-page essay and zip the file down to a simple sticky idea. They are compression algorithms.‍

Here’s 3 that I’m pissed off for not thinking of myself: (PS. I know you asked for 1, but life’s about overdelivering.)

‍1. “One should not read like a dog obeying its master, but like an eagle hunting its prey” - Dee Hock

This made me realize I had left the education system — but the education system had not left me.‍

2. “You waste years by not being able to waste hours” - Amor Tversky

This one hurts my soul. The irony is that things that look productive, e.g. Being busy — can be one of the least productive uses of your time. But things that don’t look productive, e.g. Time to think — can save you years of wasted effort  and be the most productive thing you can do.

Check out Google Trends for “busy”. It keeps going up.

3. “General ambition will give you anxiety. Specific ambition will give you direction” - Anu

I repeat this back to myself a few times per week.

What I love about these is that not only are they true/wise…but the big idea is compressed into a beautiful 1-liner.

Ooh - I like the idea of compression. So what you’re saying is…

The way compression yoga pants make your butt look perky… compression ideas makes your brain look perky?

I’ll quote you on that.

Btw - have you seen Naval’s twitter bio? 

You may be onto something...

But now you’ve got me thinking. Who’s amazing at compression, that is not in our bubble of business/tech stuff?

First answer that came to mind for me - Mitch Hedberg.

I first found Mitch Hedberg when I downloaded: “BeSt CoMeDy Of ThE NiNeTiEs.mp4” on LimeWire.

He’s funny, but the thing that stands out is his style. Mitch’s comedy is just to stand on stage, and say 1-line-jokes:

‍“I used to do drugs. I still do, but I used to too.”

(crowd cracks up)

“The best thing about escalators is that they cannot break. They can only become stairs."

‍He didn’t tell long stories like Chapelle, or do impressions like Shane Gillis. He did comedy via compression. The shortest possible path to a laugh. He did the setup, suspense, and punchline in as simple of a way as possible.

RIP Mitch.

Speaking of comedy - have you been following the presidential election? (You’ve got a British accent and live in Dubai, so I’m not sure if you simply ignore American politics, or you watch it the way I watched season 1 of the Jersey Shore, simultaneously amazed & confused if this was real life)

‍

Trump is a master of both comedy, and compression. Everyone laughed when his slogan was “Make America Great Again”, but it stuck.

‍Btw - quick test. Close your eyes. No googling.

What's Biden’s slogan?

Forget your political stance. Just purely from a marketing point of view – I couldn’t tell you what Biden’s slogan is. Isn’t that nuts? Aren’t they spending gobs of money on their campaign?

Maybe I’m living under a rock, but I couldn’t tell you his slogan.

…*does quick Google search*…

Holy shit. In 2020 Biden spent over $1 BILLION ($1,402,034,039 to be exact) on his campaign, and his slogan was:

“Our best years are ahead of us” (2020).

This year, he’s spending a ton again ($23M in March alone) and his slogan is “Finish the Job” (2024). 

Best years ahead of us? Finish the job?

I’m no expert - but don’t these sound a little “end of the roady” for a guy who’s struggling to get people to believe he’s not too old to be president?

OK, OK, I’ll stop before the government breaks into my house and hits me with a taser.

Mitch Hedberg’s compression comedy spirit lives on with Paul Carr, have you seen his stuff?

He does the 1-liner style beautifully:

“If we’re all God's children, what’s so special about Jesus?”

“Say what you want about the deaf…”

Compression artists like Mitch, Paul Graham or Naval — compress words, but maximise emotion and understanding.

E.g. Biden has compressed his slogan into “Finish The Job” — but his compression algorithm has ruined the file. There’s no emotion. I’m just confused. What does he mean?!?! Finish what job?!

I have been fascinated by this concept I call “Sticky Ideas”.

The algo for a sticky idea = [Total amount of emotion] x [How simple it is to understand].

Make America Great Again = Sticky Idea. Make Something People Want = Sticky Idea. Hawk Tuah = Sticky idea.

“Finish The Job” = Not a sticky idea.

MAGA has 4 different emotions compressed down to 4 words:

Make = Action
America = Identity
Great = Aspiration
Again = Nostalgia

And to smooth it all it fits into an acronym: MAGA. E.g. Make Brazil Great Again - MGBA, doesn’t have the same mouth sound to it. We’re all just monkeys making mouth sounds at the end of the day.

You can hate the politics — but you can’t hate the copywriting.

One funny idea I’ve been exploring: What industry is missing out because it doesn’t have sticky ideas?

Mine: Cybersecurity.

The name is so nerdy that the average person zones out whenever the topic comes up.

You could change the entire perception of the industry by rebranding to CTI’s: Computer Transmitted Infections. By doing this, you’re stacking it on top of another sticky idea that exists in people’s heads: Sexually Transmitted Infections (STI’s).

When I hear cybersecurity, I don’t feel fear. When I think about catching a CTI, I feel fear.

I love how you have all these little self-created-terms like Sticky Ideas, Computer Transmitted Infections (CTI’s), Compression algorithms, etc..

Do you just walk around naming things you see? If you see a baby, do you have a temptation to step in and name it?

Your names-of-things are so good, they need their own name. The George Mack-ivelian naming convention.

Can you turn that part of your brain off - or do you do this on first dates too…THE PEOPLE NEED TO KNOW GEORGE!

Actually - I wrote that as a joke, but now I’m curious. What’s George Mack’s take on first dates?

I know two things: 

1. There’s no shot in hell you’re saying: “uhh idk, just take her out to dinner i guess” 
2. There’s also zero chance I can predict what your answer is.

I once read a psych study that showed that people bond best over adversity & ‘successful spontaneity’ – so they suggested that the optimal first date is to show up for a standard dinner, but your reservation is canceled.

This apparently works because you are faced with a set-back and need to improvise.

The theory is that you would quickly learn the person’s true nature (handle a curveball) and if the improvised date goes well, your trauma bonds over the adversity.

So give it to us. What’s George Mack’s approach to a first date?

Oh you wanna go down this rabbit hole?

I’m unsure if what I’m about to say is Howard Hughes in his early life (genius) or Howard Hughes in his later life (insane)

AKA the Howard Hughes Superposition. (See - I can’t fucking switch it off)

Language is the most important technology humans have ever made.

But the default setting of 2024 human beings is that it’s all been figured out. They don’t ship new words. My favourite humans have their own vocabulary. McGregor-isms. Munger-isms. Musk-isms.

Dating philosophy? FFS Shaan. I was going to sell this as part of my $10K pick up artist mastermind course. You’re married so I can give this for free...

I go to local bars and airdrop my recent screenshot essays. If you think fame or money is seductive, you should try a 300 word essay on Lee Kuan Yew’s immigration policy.

No offence Shaan: I think that whole first date research stinks of Midwit meme strategy.

"If I get their heartbeat above 130 beats per minute, maybe they'll like me!" - Midwit

When I was younger, I’d turn up to the first date like I was on a job interview. Desperate to impress them, I would be a performing clown bending my personality to their interests like a dynamic Facebook ad. If they didn’t give me the metaphorical role (another date), I was devastated.

The single biggest mindset shift on first dates: You’re the job interviewer — not the job interviewee.

I went from wanting a 100% conversion rate to a 1% conversion rate. I only wanted the best metaphorical candidate I could find. Everything else was a waste of my time — and a waste of their time. The irony is when I shifted from job interviewee to job interviewer mindset on a first date — my metaphorical conversion rate improved because I didn’t stink of insecurity.

(Nuance - obvs do all the basics the guy on the left would do).

I hate dating hacks… But only one I came up with that was useful... Ask them the following thought experiment.

“God calls you and offers to build your dream partner from scratch. Looks, personality and lifestyle. What do you ask for?”

1. If they describe a guy that looks like Lebron James — I can save their time and mine!

2. If they’re going to end up dating a weirdo like me, they’re going to need to enjoy thought experiments. If not, I don’t have product-market fit and can stop wasting their time.

Haha love it.

I can’t top that. 

So let’s wrap this baby up and see if anyone enjoys reading 9,000 words (or did we just Hawk Tuah on their inbox for no reason).

Yours truly,

‍

Shaan