“I’ve seen this before.”
Few sentences create confidence as quickly.
A lawyer has acted in a similar matter. A barrister has argued the point before. An insurer knows the claim pattern. A litigation funder has invested in the same type of dispute. An investment committee has considered something that looks remarkably familiar.
Experience matters. It should. Someone confronting a problem for the fiftieth time ought to see things that someone encountering it for the first time cannot.
But there is a question hidden inside the confidence of that statement.
What exactly have they seen before?
Some experience runs vertically.
It goes deep into an individual matter: the facts, evidence, law, procedure, personalities, economics and particular behaviour of the parties. This is where specialists earn their value. They see weaknesses that disappear in an executive summary and strengths that resist being reduced to a risk score.
A litigator can understand a category of dispute exceptionally well. A barrister may know how a particular court approaches a problem. An insurer can develop a deep understanding of a class of claims. A funder may become highly skilled at assessing a particular type of investment, jurisdiction or structure.
That expertise is real.
But depth has a boundary.
Twenty years spent examining one relatively narrow category can produce extraordinary vertical experience without necessarily producing a wider view of the system around it.
There is also a subtler risk. Repetition begins to feel like learning.
The more often something resembles what came before, the faster we recognise it. Eventually recognition itself can acquire the authority of evidence.
We know this jurisdiction. We have seen this defendant. These matters run long. This type of claimant settles. This kind of case does not fund well.
Sometimes those conclusions are earned.
Sometimes one vertical has simply been experienced often enough to feel universal.
The natural response is to look horizontally.
Instead of one matter, consider fifty. Compare jurisdictions, legal teams, defendants, outcomes, costs and years. Institutional knowledge should be more powerful than the memory of one individual and, properly developed, it is.
But having seen many things is not necessarily the same as having learned across them.
Fifty underwriting exercises sitting in the same database may represent substantial accumulated experience. They do not automatically amount to horizontal knowledge. They may still be fifty vertical assessments, performed at different times, by different people and under different assumptions, without anyone having established what genuinely connects them.
The same problem occurs between people.
Put ten experienced professionals around a table and agreement can create considerable confidence. Yet ten people agreeing does not necessarily provide ten independent observations. They may have trained in the same market, relied on the same precedents, absorbed the same conventions and heard the same propositions repeated by the same respected voices.
An industry can contain an extraordinary amount of experience while recycling surprisingly little independent observation.
There is comfort in travelling together.
Agreement can reduce the discomfort of uncertainty without reducing the uncertainty itself. A group can become increasingly confident in the path it is taking without becoming any more certain of where that path leads.
The effect strengthens when everyone uses similar tools, classifications and assumptions. Similar inputs passed through similar frameworks will often produce similar conclusions. The convergence feels reassuring because several people have arrived at the same place.
Sometimes that is corroboration.
Sometimes they simply travelled by the same road.
Then we create another form of order: averages.
Average duration, legal spend, settlement, recovery, loss, return.
These numbers can be extremely useful. But an average answers a question only after someone has answered a more important one:
Average of what?
A commercial dispute before a specialist court may tell us surprisingly little about a mass claim before an ordinary court. A sovereign defendant does not necessarily behave like an insurer; an insurer does not behave like a listed manufacturer. Matters can all sit comfortably within the description of “litigation” while operating inside very different procedural, regulatory and economic systems.
The arithmetic can therefore be perfectly correct while the comparison beneath it is wrong.
Before the average exists, someone has already decided what belongs in the population.
That judgment may matter more than the calculation that follows.
Which brings me to pick-up sticks.
As children, many of us played some version of the game — Mikado in parts of the world.
A bundle of thin sticks was held above a table and released. They fell wherever they fell: crossing one another, lying almost parallel, becoming trapped underneath others, forming concentrations in places while a few landed almost entirely alone.
The object was to remove them carefully, one by one, without disturbing another.
Looking at that pile now, through adult eyes, there is an almost irresistible urge to impose order.
Separate the colours. Straighten the sticks. Put similar ones together. Create categories. Make the disorder easier to understand.
But what if the first analytical mistake was moving the sticks?
The configuration contains information, even though not every apparent pattern within it will prove meaningful.
Some sticks touch. Some overlap. Some can move independently while others cannot move without disturbing something around them. There are concentrations, edges, isolated pieces and empty spaces.
Straightening the sticks makes them easier to describe.
It can also remove part of what the original arrangement was telling us.
Litigation and litigation finance contain the same tension.
Every matter has its own profile, but very little about any matter is entirely unique. The useful question is not whether a case is unique or comparable. It is which similarities matter, which differences matter, and why.
Two matters carrying the same legal label can behave very differently because their defendants, procedural environments or economic incentives differ. Two matters that appear unrelated legally may exhibit similar behaviour because the forces acting upon the parties are similar. A risk attributed to duration may turn out to be the consequence of something else entirely.
The interesting patterns do not always follow the categories we begin with.
A group that initially looks coherent may separate into several clusters once viewed differently. Something dismissed as an outlier may instead belong to a pattern the existing classification was never designed to recognise.
This makes experience harder to define.
The answer cannot be to insist that every stick is unique. Taken too far, that destroys our ability to learn from anything that came before.
Nor can the answer be to straighten enough sticks until history becomes neat enough to fit an existing model.
The harder discipline is to leave them where they lie long enough to understand the relationships already there.
That requires us to examine the person doing the looking as well.
Experience changes what we notice. A painful investment can make us unusually alert to its resemblance elsewhere. An exceptional return can make us equally talented at finding reasons why the next opportunity belongs beside it. Once an organisation has built a framework for categorising risk, new opportunities naturally begin passing through that framework.
Frameworks are necessary.
The danger begins when we forget that the framework is something we imposed on the information, rather than the information itself.
Are we discovering a pattern, or creating one? Is the comparison genuinely relevant, or merely familiar? Did the evidence lead us to the conclusion, or did the conclusion determine which evidence we treated as important?
And when an entire industry reaches broadly the same view, are we seeing independent corroboration — or one assumption reflected back through many experienced voices?
For investors, the distinction matters.
Opportunity does not necessarily sit in the middle of the cleanest and most familiar cluster.
It may sit at an edge, where apparently different patterns begin to overlap. Something dismissed as an outlier may contain the characteristic that matters most. Or the interesting part may be the gap: the place that existing classifications, accumulated experience and shared assumptions have encouraged everyone else not to examine closely.
Risk can hide in the same way.
Something sitting comfortably inside a historical average can feel safer precisely because everyone recognises it. Familiarity makes a decision easier to defend. It does not make the underlying risk disappear.
None of this argues against experience.
It argues for demanding more from it.
Perhaps genuine experience is not the ability to say “I’ve seen this before” with increasing certainty.
Perhaps it produces a more disciplined response:
It looks like something I’ve seen before. Now let’s establish whether it actually is.
The temptation is to straighten the sticks until they resemble something we already understand.
The harder discipline is to read them where they lie.
That is the territory Wild Dog is interested in: the assumptions, structures and commercial decisions that shape litigation and litigation finance before the eventual outcome makes them obvious.
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