Sources: despite a November 2019 pledge to slow down, Masayoshi Son pushed SoftBank staff into investing $38B out of Vision Fund 2 across 180+ companies in 2021
Wall Street JournalEliot Brown
Context & Ripple Effects
The story closes a loop that opened with reporting on Masayoshi Son's hard-edged dealmaking style at the original $100B Vision Fund, which had already put $30B to work in its first year. After the fund's troubles, Son pledged in November 2019 to slow down — yet by mid-2021 Vision Fund 2 was accelerating, deploying about $13B into over 50 companies in a single quarter, up from under $3B the quarter before.
What the WSJ now reports is that the 2021 surge was not drift but push: $38B across 180+ companies in one year, driven personally by Son against his own stated restraint. The later arc matters too — filings show the US portfolio has since shrunk by almost $29B since the end of 2021 as Son pivots toward AI and chips, making the 2021 deployment the peak of the cycle.
First-order effects
SoftBank staff who were pushed into deploying $38B across 180+ companies in 2021 now sit on positions marked down sharply, with the US portfolio down almost $29B since end-2021.
Second-order effects
The earlier plan to lend employees up to $20B to buy stakes in the second fund ties staff balance sheets directly to Vision Fund 2's performance, amplifying the internal cost of the 2021 deployment spree.
Third-order effects
If the pattern holds — a founder overriding his own slowdown pledge, then pivoting the remaining capital to AI and chips — SoftBank's investment cadence is set by one person's conviction rather than fund governance, with the 2021 peak-to-2024 drawdown as the cautionary data point.
The trend: Mega-fund tech investing keeps concentrating deployment decisions in a single founder's hands, with Vision Fund 2's 2021 surge and subsequent shrinkage marking one full cycle of that model.
As DoorDash & Coupang surged, Masa opened the spigot on startups He made a big spreadsheet, where calls to potential investments by Vision Fund staff were logged. investors felt like salespeople; mentioned “Dial for Dollars” & “Glengarry Glen Ross” to describe it https://twitter.…
Take Klarna. SoftBank put $1.7 B(!) into Klarna, more than we knew earlier, in 2021, at a ~$35 B valuation It also struck a deal to put in another $2 B, though later scuttled those plans Klarna was recently valued at $6.7 B; SoftBank didn't participate
“When he believes something is the future he will literally take everything he has and bet it on that..I don't think that leopard changes its spots.” On Masa Son and SoftBank's latest rout @eliotwb https://www.wsj.com/...
SoftBank is a Mamet play: The process had an aura of “dial for dollars,” one former executive said. Another compared it to a sales-pitch list in “Glengarry Glen Ross,” the play about a set of anxious real-estate salesmen. @eliotwb https://www.wsj.com/...
After WeWork's 2019 implosion, SoftBank's Masayoshi Son told staff to be disciplined and more cautious in startup investing Then he accelerated and spent $38 B, the most ever, out of Vision Fund 2 in 2021, just as the market crested https://www.wsj.com/...
SoftBank CEO Masayoshi Son promised to curb his aggressive bets. Then he poured $38 billion into startups last year at the top of the market. https://www.wsj.com/...