Tim

a friend of mine often talks about the importance of not losing the plot, and how many people/companies have lost it but they never realise. here we have an instance of that:

probably the largest mental barrier people have regarding ai. your brain still connects work and creating things with effort, you're putting lots of mental energy into getting things right with the fewest revisions possible. but you can just throw your ideas at it. output bad? give feedback. bad again? more feedback. just repeat until it's perfect. you need to adapt a totally different mental model.

it's interesting to say this as a person who puts a lot of value on doing things the proper way, but I think NDAs are a problem. work should be more integrated into our lives, it can't be if you can't talk about it. great ideas are formed in conversation, esp during conversations with people that have a different bias. again, can't happen if you can't talk about it. likely the damages a NDA produces outweigh it's benefits, for the most part.

I think greatest networking hack: See something interesting about person/interesting person online -> have questions -> get phone number -> call & ask question

Something very interesting about the enterprise software market is how existing companies fundamentally cannot make good software. All of them are world class sales orgs, and horrendous product orgs. As soon as the buying decision (1) becomes less political and (2) migration friction decreases, they crumble. Many extremely large opportunities to capture here.

I’d honestly rather have a founder who knows everyone and their mother than one who locked themselves in a room for a couple of years. As a founder, your primary jobs are: (1) generating great ideas, (2) knowing people who can help you out of the shit you’ll dig yourself into countless of times. All depends on the stage of the company, but going to a couple high-class events isn't a bad thing to do. Just don't go to networking events or fucking trade shows.

Most if not all problems people have are created by bad mental frameworks creating negative feedback loops. Losing is part of it I must accept it -> you accept losses too early -> you stop trying to win You expect little from someone -> person naturally puts in less effort -> exception gets confirmed & bias is created I failed at this, so I'm not good enough → you read every new event as more proof → you sink deeper into the low mood that confirms it

The Beatles

From what I've seen in the past few months, it doesn't really make sense to hire AI-native people specifically. For one, it kills your potential pool of candidates because even good people in many areas just haven't properly adapted to it yet. For two, AI and specifically the important tools haven't been around for that long. Even if you hire somebody who is fully AI-native, the stuff they learned in 12 months of fucking around, you can easily teach in a month if you have a proper streamlined process. So cost wise: training proficiency < hiring for proficiency

B2B has a lot to learn from consumer on marketing, practices truly have not changed for ages. It feels like the stone age has begun yesterday. Buy booth at event. Put logo on F1 car. Give people branded coffee mugs. Really?

If you walked into a Fortune 500 boardroom right now and told them about tokenmaxxing and running loops, they'd hang and execute you, in that order.

When trying to gain a competitive advantage, there are essentially two things to look at: 1. Things your competitors are also aware of. Based on their backgrounds, they will naturally focus on certain information. If you're competing against people from the finance industry, they will be very aware of what's happening in finance. Even if the industry you're now competing in isn't finance, if everyone you're up against came from finance, they'll be focused and biased accordingly. 2. Things your competitors are unaware of. Someone from finance, for instance, won't know anything about production processes, how supply chains operate, or other unrelated fields. The competitive edge lies in identifying two things: 1. Who you're competing against and what their biases are. 2. How you can use those blind spots to your advantage. If you look in the same places they look, that's a waste of time - they'll come up with the same ideas, test them, and use them if they work. You could simply copy what they're already doing. The only areas worth exploring are ones they're unaware of, would never think to consider, and would dismiss entirely.

The Danger of Unidentified Luck We are addicted to causality. When something succeeds, we need a reason. The victorious founder tells a story of vision, grit, and strategic brilliance. The failed founder tells a story of bad timing, unfair markets, or betrayal. Both narratives are constructed after the fact, and both are largely fiction. The company that survived 2008 and bought distressed assets may have had cash reserves, yes, but it may also have been lucky in its timing, its geography, its particular product cycle. A thousand equally prudent companies failed because their landlord raised rent at the wrong moment, because a key employee got sick, because a pandemic arrived from nowhere. The human brain cannot tolerate randomness, so it manufactures stories. It sees patterns in static and calls them strategy. Consider the famous "skill" of market timing. In retrospect, every successful tech founder saw the wave coming and positioned themselves perfectly. But at any given moment, thousands of equally intelligent people are positioning themselves for thousands of different waves - most of which never arrive. The ones who bet correctly get to write the history books - the others disappear without a trace. Most business advice treats the market like a chess board - a closed system where the right sequence of moves guarantees victory. But business is poker played with a deck that keeps changing size. New cards are added mid-hand, old ones are removed, and occasionally the dealer lights the table on fire. Skill determines how you play your cards, but it does not determine which cards you are dealt. The practical implication is not that effort is pointless - it is that humility is severely undervalued. The founder who believes their success is 90% skill will make very different decisions than the founder who suspects the ratio is closer to 50-50. The first will double down on their genius. The second will diversify, hedge, and remain paranoid

The most dangerous lie in business is the level playing field. We are taught from a young age that fairness is a virtue. In the schoolyard, it is. In the market, it is a death sentence. A fair game is one where the outcome is uncertain. It is a coin toss. If you find yourself in a situation where the odds are fifty-fifty, you have already failed. You are gambling with your time and your capital. High-level operators do not play fair games. They seek out markets that are inefficient, opaque, or tilted in their favour. They look for the unfair advantage. If you are competing on price, you are in a fair game. If you are bidding against ten other firms with the same credentials, you are in a fair game. These environments will strip away your margin until there is nothing left but the cost of your own labour. The goal is to rig the outcome before the first move is made. You do this through proprietary data, deep political ties, or a brand that makes the competition irrelevant. You want a game where you are the only one who knows the rules. Most people find this idea repulsive. They want to believe that hard work alone is enough. But the market does not reward effort. It rewards the capture of value. And value is easiest to capture where the competition is locked out. When you hear someone complain that a situation is "unfair", listen closely. They are usually describing a moat they do not possess. The "unfairness" they see is the result of someone else's superior strategy.

The Alpha of Staying Alive In professional tennis, points are won. In amateur tennis, points are lost. The amateur defeats himself. He swings too hard, chases the impossible angle, and hits the ball into the net. The professional does something far less glamorous - he simply returns the ball, again and again, until the other player makes an error. This observation comes from Dr Simon Ramo, one of the architects of the American intercontinental ballistic missile programme. He studied thousands of tennis matches and found that at the amateur level, roughly 80% of points are decided by unforced errors. The winner is not the player who hit the most brilliant shots. It is the player who made the fewest mistakes. Business follows the same physics. The default state of a company is death. Cash depletes, markets shift, founders burn out. Most businesses do not fail because they made the wrong move - they fail because they ran out of time to make the right one. The graveyard is full of companies that were six months away from success. We romanticise the breakthrough. We study the pivot, the product launch, the genius insight. But these are the highlights. The underlying game is far more brutal: you must stay solvent long enough to get lucky. Survival is not a passive state. It is the most aggressive strategy available to you. Every month you remain in the game, a competitor folds. Every quarter you stay solvent, the market consolidates in your favour. The longer you exist, the fewer players share the field. This is compounding, but in reverse. You are not trying to win every point. You are trying to be the last one standing when everyone else has exhausted themselves. The most valuable opportunities are invisible to those who are fighting for their lives. When you are scrambling to make payroll, you cannot see the acquisition target that is about to become distressed. When you are one month from bankruptcy, you cannot negotiate from a position of strength. Cash is not idle capital but the ability to act when others cannot. The 2008 financial crisis created more fortunes than it destroyed. The ones who emerged on top were not those who made the most aggressive bets. They were those who had the capital to buy when everyone else was forced to sell. Consider the careers we celebrate as "overnight successes". James Dyson went through 5,127 prototypes over 15 years before producing a vacuum cleaner that worked. He was sustained by his wife's salary as an art teacher. He nearly went bankrupt multiple times in the process. He was not a gambler. He was an engineer of longevity. The survivorship bias in business media creates a false map. We see the winners who took enormous risks and succeeded. We do not see the graveyard of thousands who took identical risks and vanished without a trace. The winner's narrative always sounds like courage. The losers' narratives are simply never written. The irony: "staying alive" is perceived as a conservative, even cowardly, strategy. It is anything but. Most of your competitors are optimising for short-term wins. They are trying to hit the perfect shot, close the deal this quarter, show growth at any cost. They will burn through their runway, their relationships, their credibility - all in the pursuit of acceleration. To win, you simply need to outlast them.

The Psyop of Taking Risk We are living through a cultural fetishisation of "the leap." Risk-taking has been elevated from a necessary evil to a moral virtue. We’ve turned the "all-in" moment into a status symbol. Most people view risk through the lens of bravery. They believe that the magnitude of the outcome is mathematically tied to the magnitude of the danger they face. This is a fundamental misunderstanding of reality. Risk and reward are decoupled. When the "hustle culture" echo chamber becomes loud enough, people start to believe that if they aren't terrified, they aren't dreaming big enough. They begin to seek out risk for its own sake, confusing the adrenaline of a gamble with the discipline of a strategy. In this environment, "taking a risk" is often just a mask for poor planning. The alpha has never been the willingness to jump off cliffs but the patience to build the most efficient bridge. The market does not care how high your heart rate was when you signed the contract. It does not pay a premium for the nights you spent staring at the ceiling, wondering if you’d lose everything. If you achieve a billion-dollar exit through a sequence of low-risk, high-probability moves, the value of that capital is identical to the capital earned by someone who bet their house on a coin flip. The outcome is a product of your ambition and your execution, not the level of personal peril you endured. What seems like an immense risk to the outsiders, is likely to be a very low-risk one to the high-performer - he has thought about it deeply. Consider the logic of the "brave" path. If someone gave you the choice between a 100% chance of receiving $1 million and a 10% chance of receiving that same million with a 90% chance of total ruin, choosing the latter isn’t "living on the edge." It is simply stupid. Yet, we see this exact behaviour mirrored in the professional world every day. People choose high-volatility paths because they’ve been sold the lie that "big risk equals big reward." In reality, the high-risk path is often just the inefficient path. The goal is to reach the destination, and there are infinite routes to any single summit. Some are sheer vertical faces that require a leap of faith; others are paved, gradual inclines. There is no extra credit for choosing the path that might kill you. True high-level operators are not risk-seekers; they are risk-mitigators. They spend their time ruthlessly identifying and eliminating points of failure until the "risk" is nothing more than a controlled variable. They understand that the "all-in" moment is often a sign of a failed strategy - a point where you’ve left your fate to chance because you lacked the foresight to secure the outcome earlier. The most impressive feats of entrepreneurship aren’t the ones that were a coin toss away from disaster, but the ones that were so well-planned they felt boring. Not to say that it's impossible that an "all-in" type of path might become the only path you could possibly take, but it shouldn't be the goal to end up at such a point. The more you can decouple your ego from the narrative of the "brave struggle," the more clearly you will see the low-friction routes that others are too "courageous" to take.