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One investment can decide the return of twenty

Venture portfolio returns follow a power law: most of the money comes from very few companies. Working through a portfolio's arithmetic shows why missing the best company matters more than avoiding the worst.

11 min read · Level 5

The point

I think the most counter-intuitive fact in early-stage investing is that a portfolio where half the companies fail can be excellent, and one where none fail can be poor. Once that arithmetic is felt rather than just understood, most decisions about breadth, sizing and follow-ons become clearer.

What is it?

Consider a portfolio of 20 equal investments of 1 unit each:

Outcome Companies Multiple Returned Failure 10 0x 0 Break-even 5 1x 5 Good 3 3x 9 Very good 1 10x 10 Outlier 1 50x 50 Total 20 74

Portfolio multiple = 74 / 20 = 3.7x

Now remove the single outlier and replace it with a failure:

Total returned = 74 - 50 = 24 Portfolio multiple = 24 / 20 = 1.2x

One company out of twenty produced 50 / 74, about 68%, of everything returned. Half the companies returned nothing, and the portfolio still did well.

Two implications:

The cost of a failure is capped at the amount invested (1 unit here). The cost of missing an outlier - by not investing, or investing too little - can be most of the portfolio's return.

Why does an investor care?

Because it changes how investment decisions should be made. Avoiding failures matters far less than being in the rare company that returns many times the capital.

It also explains why concentration is dangerous for early-stage investors: with only five companies, the chance of holding any outlier is much lower than with twenty or thirty.

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Educational, not personalised financial advice. Nothing in the Investor Academy is a recommendation to buy, sell or hold anything — what is right for you depends on your own circumstances and the rules where you live.

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Example

The chance of holding at least one outlier.

If each investment independently has a 3% chance of being a 50x outlier, the chance of holding none is 97% multiplied across all holdings:

Holdings Chance of no outlier Chance of at least one 5 0.97^5, about 85.9% about 14.1% 20 0.97^20, about 54.4% about 45.6% 40 0.97^40, about 29.6% about 70.4%

The probabilities are illustrative, not predictions. But the pattern holds: breadth is how early-stage investors give themselves a realistic chance of the outcome that drives returns.

The common mistake

Judging a portfolio or a decision by its failure rate, when returns are driven almost entirely by the size and presence of the few largest outcomes.

How it works

Step 1: Model the portfolio, not individual deals

List outcome groups with counts and multiples.

Step 2: Find the share from the top outcome

Calculate how much of the return depends on one company.

Step 3: Test removing the outlier

Recalculate the portfolio without the best company.

Step 4: Plan enough holdings

Choose breadth that gives a realistic chance of an outlier.

When to use this

When planning an early-stage portfolio or judging whether it is working.

When not to use it

Do not assume power-law patterns apply equally to later-stage or income-focused private investments, where outcome distributions are narrower.

How investors actually did it

A recurring pattern: return concentration in venture data

Analyses of venture capital fund and deal-level returns published by industry data providers and venture firms have repeatedly found that a small percentage of investments account for the majority of total returns, and that many individual investments return less than their cost.

Return concentration is not a feature of a few lucky funds; it is the normal shape of venture returns.

Do this now

  • Calculate your portfolio multiple with and without its best company
  • Work out the chance of at least one outlier for your planned number of holdings

Create a free account to read the rest and apply it to your own investing.

Related lessons

  • The first ten holdings do most of the work; the next fifty do much less — Adding holdings reduces the damage any single failure can do, but the benefit falls away quickly. Beyond a point, more names add admin and dilute your best ideas without removing much risk. (10 min)
  • One investment in twenty pays for the other nineteen, or nothing does — There is no coupon and no dividend here. The return is realised only at an acquisition or a listing, most positions return little or nothing, and the entire portfolio's economics usually rest on one or two outcomes out of many. (12 min)
  • The same company can be a good investment at one price and a bad one at another — An investment decision weighs the range of outcomes against the price paid. Scenario-based expected value shows how quickly a higher price erodes the return from the same company. (11 min)

Next: Ownership at exit is ownership today multiplied by every round's dilution