Hey Reader,

Everyone asks for the playbook. Give me the SOP. Give me the steps. Give me the framework, the template, the proven path. The idea of certainty that if you do X then Y happens is super comforting. And there is a time for certainty-based operations.

Just not today, not at the beginning. At the beginning you have to be willing to repeatedly start with a blank piece of paper vs overlaying a playbook that the market has said worked historically.

Playbooks, by definition, force you to optimize for mediocre which in a startup, is fatal.

When the traction drops or the results don't come, you didn't necessarily do anything wrong. You just allowed yourself to be mediocre on accident.

It's called Extremistan (Taleb). The idea that some domains are governed by averages, as in the middle is safe, just blend in - think SLA's / uptime, at 99.9% no matter how epic you are, it's capped at 100. Think receptionist, it's linear, they can only handle so many people per hour, accounting is binary - so there is this one side this non-scalable ops and admin side of your business that is NOT extremistan.

In outlier domains (like startups!), the middle of the distribution, the average is the opposite of safe. The only rational strategy when the odds are this skewed IS to exist at the tail. Start blank. Think how, what, when, where, why, who, not to follow a path, but to find the edge where you can have outsized impact.

That’s Extremistan and where you have to live.

If you read anything I ever write, hundreds of playbooks, hundreds of newsletters, and a book that’s sold a few copies, I never tell you what to do. Ever. My playbooks are not SOPs or paint-by-numbers maps, they are frameworks on how to think about the problem because there is no other choice. If I deliver MY playbook that worked for ME at that moment with MY context - it might work for you - sure but not at the outsized results.

A standard playbook, by definition, gives you a sequence of steps to someone else’s answer to someone else’s problem in someone else’s context. Real thinking gives you YOUR answer, to YOUR problem, in YOUR specific context, built on YOUR specific obsession and nothing else can produce an outlier outcome.

…and therefore by default you cannot reverse engineer in real time what the dark horse is doing, because its not outsized capital, or a weird secret weapon, or a Stanford hoodie, it’s just them optimizing for something very, very specific and got there by being genuinely, obsessively, specifically great at a thing by being willing to think about the thing for longer.

The dark horse isn’t the idea. It’s how you think.

THE PLAYBOOK TRAP

Everyone to some degree consumes playbooks, podcasts, Twitter threads, frameworks, case studies, the whole buffet. Good. You should. I wrote about ignorance being a superpower and I meant it, I doubled down to ask if you are ignorant or incompetent, but at some point, you need to actually know things and move from consumption to knowledge (the why).

Some founders find their creator, their Lenny, their Jason, their Harry, their Maggie and consume the playbook and follow it like a religion because most of what they say genuinely is both true and resonates but it generates two types of people. One who is trying to re-create - you see this with the people on LinkedIn and that doesn’t work - puts you into the average without you even knowing. OR you find your creator to learn how to think about thinking you don’t want their output, you want to learn the thinking that got them there.

We talked about this, NPC Mode - are you just a background character executing someone else's battle in someone else's war.

This is not rebellion for the sake of it, it’s not hyper-contrarianism, it’s the founder who can take the same inputs, can think, and reaches a conclusion based entirely on THEIR own context and THEIR own specific obsession with some corner of the problem that THEY feel strongly about. This is why I tell founders to close the laptop, go for a walk, and just think. It’s lonely, it’s generative, and it’s HARD - there is no safety net of a “proven framework” to blame when a net-new approach doesn't work and you’re wrong.

THE CRUEL IRONY OF BEING RIGHT….

I read this line which actually prompted the whole newsletter.. Complex goals in complex systems are best achieved indirectly.

It took me a while to process, but when I did, it’s a terrifying thought. The VC deck, the ad campaign, the sales playbook, the product prioritization, the SOPs you (still) wish you had, the structure, the accountability, is mathematically proven to build a mediocre company.

Every deck has a revenue slide, every board meeting starts with numbers, every investor asks for NRR but the evidence says the founders who optimize entirely for the numbers produce worse numbers than the founders who optimize for being genuinely great at the thing. What are you supposed to do, walk in with no deck, no numbers, no POC?! Obviously not, but knowing the difference between the deck that reports reality vs the deck that replaces your thinking is the unlock.

When you are obsessed with engineering or product excellence or YOUR thing, you smash the market but when you raise an angel round to make it a reality and are forced to optimize shareholder value in prep for Series A the inside-out rot starts.

The dark horse gets this and just refuses to let the score dictate how they play. I’m sure you have heard this line… When a measure becomes a target, it ceases to be a good measure. Optimize for NPS and you get survey gaming. Optimize for growth and you get unsustainable spend. Optimize for the metric and the metric rots. Optimize for rats killed and you get a side business spawning rats.

Optimize for being f’ing exceptional at the thing? The metrics take care of themselves. Great products produce great numbers. Not the other way around.

THE IDIOT

The graveyard is full of founders who thought they were visionary and were actually just delusional and they look the same at the beginning with the same “nobody gets it yet.”

The question to work out which one you are... dark horse or just delusional: Can you articulate what would change your mind? - it’s that simple. Are you defending your idea because you view the feedback as a threat or a privilege.

That’s the whole test. The dark horse says: “I believe X, and here’s the specific evidence that would make me abandon X.” The delusional founder says: “I believe X, and nothing will change my mind because I just know, and you don’t get it.”

It’s the same founder position, with a totally opposite process.

The dark horse is obsessively truth-oriented, they hold a non-consensus view AND they actively hunt for reasons they might be wrong. They want to be right more than they want to feel right. A dark horse might agree with the consensus on 90% of decisions because the consensus is right about 90% of things. Standard accounting, standard HR, standard ops. You don’t dark-horse your payroll.

The edge is one or two bets, the specific place where YOUR context, YOUR knowledge, YOUR weird obsession with some niche problem creates an insight that the playbook written for the average, built for the general founder, simply cannot see.

When you look closely at these outlier dark horses, you realize they optimize entirely for micro-motives. It’s not talent (it is) but it can be purchased, it’s also not grit (it is) because grit is just suffering in a hoodie, it’s specificity. It’s this almost weird visceral, unhinged obsession with sometimes the most weird minute detail that just seems bad or wrong or stupid or annoying or counter-productive or whatever and the dark horse foundationally refuses to live in a world where the system is that lazy!!

That level of specificity looks like delusion sometimes at the beginning as you are finding your bearings but again, the difference is the allocation of effort on this bad, wrong, stupid thing. The outcome is always execution velocity that is uncompetable.

THE INSTRUCTION

Consume everything. Know the playbook. Know why it works. Know what assumptions it’s built on. And then sit with all of it and ask yourself where is the playbook wrong for you specifically?

Not wrong in general. Wrong for you. Your market, your customer, your timing, your team, your obsession. The gap between what the playbook assumes and what you specifically know is the edge.

Then be genuinely great. And run.

Also if you got this far and are excited that you are a dark horse - email me the specific assumption you are diverging from and the specific evidence that would prove you wrong.

If I can be of service, feel free to grab time.

LFG.

— James

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