If SoftBank pulls it off, the move would cement Son’s reputation as a feared dealmaker, one that earned him the nickname Big Stack Bully. That’s because SoftBank would be a huge beneficiary of such a massive down round while everyone else could be clear losers.
The Vision Fund(1) paid top dollar when it built its stake of around 29% in the office rental startup. By buying more shares, at an $8 billion valuation, Son might get to increase his stake while lowering the average price at which he paid. That would boost any possible upside from a future IPO, even if it were to happen at a substantial discount to $47 billion.
While talks are fluid and terms could change, as Bloomberg noted, a likely result of such a rescue package is that existing shareholders might lose on all counts: Their stakes get diluted and the value of their investment gets slashed, yet they’re stuck with a much higher average price of acquisition. Shareholders who didn’t pay cash for their stakes, such as employees, wouldn’t suffer that third consequence, though they’re no less disadvantaged since they’ve effectively bartered cash salary for shares.
What would be more troubling than SoftBank making this offer is WeWork’s board actually accepting it.
Currently, they’re weighing up two options: the SoftBank equity deal and a debt package being put together by JPMorgan Chase & Co. Many board members will also be equity holders — representing investors such as VCs — so anything that cuts their stake or valuation wouldn’t be welcome. Debt, on the other hand, transfers risk to bondholders.
Given WeWork’s current financial situation, though, debt investors have been growing increasingly skeptical of the company. Its 2025 U.S. dollar bonds plunged over the past month, with the JPMorgan-led financing package reported to include debt with yields as wide as 15%. Taking the SoftBank package would likely indicate that JPMorgan couldn’t put together an attractive enough deal for its consortium of about 100 investors to stomach.
It could be a pyrrhic victory for Son, though. I recently argued that his reputation is more important than his stake in WeWork. The Vision Fund should be able to write down that investment to zero and still churn out attractive returns. But there are signs that the halo surrounding Son and SoftBank is starting to fade.
Japan’s Finance Ministry plans to close a tax-avoidance loophole that SoftBank used to its advantage, Nikkei reported Sunday. The company paid no tax in Japan last year thanks to a series of complex paper transactions that booked losses by shifting assets within the group, according to the newspaper. In other words, a good portion of SoftBank’s returns last year came not from savvy investing but merely from exploiting tax laws.
That sort of thing feeds into an increasing distrust by regulators and the general public for tech companies and their billionaire bosses who dodge taxes, no matter how legally. SoftBank and Son need trust to raise a second $107 billion Vision Fund, get regulatory approval for the merger of its U.S. telco Sprint Corp., and have continued access to the best deals in the startup world. Forcing a haircut of this scale on WeWork at its weakest moment, and at the expense of other stakeholders, won’t help build that kind of confidence.
(1) The stake is held by theSoftBank Vision Fund and affiliates
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Tim Culpan is a Bloomberg Opinion columnist covering technology. He previously covered technology for Bloomberg News.
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