$20m · 2000
Masayoshi Son
Alibaba, 2000
A $20m cheque into a Chinese company that barely existed, held for more than two decades — frequently described as the single most profitable venture investment ever made.
What happened
In 2000 Masayoshi Son invested $20m in Alibaba, then an obscure Chinese e-commerce startup. The decision is usually retold as having been made in minutes, which is the sort of detail that survives because it is entertaining; the substantive fact is the size of the position and the length of the hold.
Alibaba listed in New York in 2014 in what was at the time the largest technology public offering ever completed, and SoftBank's stake was worth a figure in the tens of billions. Son did not sell into the listing.
He sold, in stages, over the following decade. Reporting on SoftBank's divestment describes gains on the original outlay of a magnitude that puts the investment in a category of its own, and by the mid-2020s SoftBank's run as Alibaba's largest shareholder had come to an end.
Peak valuations attached to the stake vary wildly by source and by date — figures from $75bn to around $200bn appear in credible outlets depending on when the calculation was performed. This page therefore anchors to the multiple actually realised rather than to a peak paper value.
Where sources disagree
What we do not claim
Peak stake valuations reported by credible outlets range from roughly $75bn at the 2014 listing to figures near $200bn at later dates. Because these are paper values at particular moments rather than realised proceeds, we do not present any of them as the return.
For your own cheque
What an angel takes from this
- The holding period is the lesson, and it is the opposite of the Thiel entry. Twenty years of not selling is what converted an excellent investment into a historically unusual one, and almost nothing in the structure of professional investing makes that easy to do.
- For an angel the parallel is exact and the constraint is different: your problem is not quarterly pressure but liquidity and life. Money you might need is money you will sell at the wrong moment, which is why the allocation rule — only capital you can lose entirely and not miss for a decade — is the thing that makes long holding possible at all.
- Note also what this entry does not claim. Son has made investments of comparable size that went very badly, several of which appear in our post-mortems section. A single spectacular outcome is evidence about a distribution, not about a person.
Checked, not remembered
Sources
Every figure on this page is traceable to published reporting. Where credible sources disagree we say so above rather than picking the most quotable number, and we do not state what a stake is “worth today” — that moves with the share price and is stale the moment it is written.
The mechanics