Will WeWork’s rescue plan backfire on SoftBank?

The Embarcadero WeWork offices in San Francisco. Photographer: Michael Short/Bloomberg

WeWork’s valuation keeps sliding. SoftBank Group Corp., its largest outside investor, is now targeting $8 billion through a rescue package it’s putting together, according to Bloomberg News. But Masayoshi Son ought to be careful. While the deal may set a floor under WeWork, it could also diminish his standing along with SoftBank and its $100 billion Vision Fund.

Mere months ago, WeWork was seeking an IPO at a $47 billion valuation, now withdrawn amid whispers that the real value should be closer to $15 billion. SoftBank’s new plan goes even further and represents an 83% haircut that means serious pain for The We Co., founder Adam Neumann, and other shareholders including venture-capital investors and employees.

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 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.

Bloomberg

Singapore Reporter/s

In Singapore, we are looking to double our reporting team by this year-end to comprehensively cover the fast-moving world of funded startups and VC, PE & M&A deals. We want reporters who can tell our readers what is really happening in these sectors and why it matters to markets, companies and consumers. The ability to write precisely and urgently is crucial for these roles. Ideal candidates must have to ability to work in a collaborative, dynamic, and fast-changing environment. We want our new hires to be digitally savvy and ready to experiment with new forms of storytelling. Most importantly, we are looking for hard-hitting reporters who work well in a team. Collaboration and collegiality are a must.

Following vacancies can be applied for (only in Singapore).

Following vacancies can be applied for (only in Singapore).   

  • A reporter to track companies/startups that have raised private capital, and have the potential to become unicorns. SEA currently has over 40 companies with a valuation of over $100 million and under $1 billion.
  • A reporter who can get behind the scenes and reveal how funding rounds are put together, or why they’ve failed to materialise. She/he in this role will largely focus on long-format stories. 
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Singapore Reporter/s

In Singapore, we are looking to double our reporting team by this year-end to comprehensively cover the fast-moving world of funded startups and VC, PE & M&A deals. We want reporters who can tell our readers what is really happening in these sectors and why it matters to markets, companies and consumers. The ability to write precisely and urgently is crucial for these roles. Ideal candidates must have to ability to work in a collaborative, dynamic, and fast-changing environment. We want our new hires to be digitally savvy and ready to experiment with new forms of storytelling. Most importantly, we are looking for hard-hitting reporters who work well in a team. Collaboration and collegiality are a must.

Following vacancies can be applied for (only in Singapore).

Following vacancies can be applied for (only in Singapore).   

  • A reporter to track companies/startups that have raised private capital, and have the potential to become unicorns. SEA currently has over 40 companies with a valuation of over $100 million and under $1 billion.
  • A reporter who can get behind the scenes and reveal how funding rounds are put together, or why they’ve failed to materialise. She/he in this role will largely focus on long-format stories. 
  • A journalist to track special situations funds, distressed debt and private credit (from the PE angle) across Asia.