Masayoshi Son has now lost more than $4 billion on a series of side deals he set up at SoftBank Group Corp. to boost his compensation, a painful blow triggered by the broad downturn in the technology market.

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The Japanese billionaire took the unusual step of establishing personal stakes in a series of SoftBank ventures in recent years, a mixing of company and executive interests that drew the ire of investors. Son holds 17.25 percent of a vehicle set up under SoftBank’s Vision Fund 2 for its unlisted holdings, as well as 17.25 percent of a unit within its Latin America fund, which also invests in startups. He has a 33 percent stake in SB Northstar, a vehicle set up at the company to trade stocks and derivatives.

Son has racked up a deficit of $2.1 billion from his Vision Fund 2 interest, and $205 million at the Latam fund, according to disclosures for the June quarter. His cumulative loss at SB Northstar is 274.6 billion yen ($2 billion). The amount Son owes SoftBank from his interests in Vision Fund 2 and the Latam fund rose to about $1.9 billion in the last quarter.

“It is controversial for a business leader to mix his personal financial interests with corporate responsibilities,” said Marvin Lo, an analyst with Bloomberg Intelligence. “But Son explained before that he wanted to use co-investment to provide financial benefits to managers, similar to venture capital firm partners getting a 20 percent to 30 percent performance fees, but with a downside too.”

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A representative for SoftBank said it is more accurate to call the figures for Son linked to the Vision Fund 2 and Latam fund as “net payable” to the company rather than losses. There is no deadline for repayment and the value of his positions could improve in the future. For SB Northstar, Son has already deposited cash and other assets so his remaining deficit is 222.8 billion yen. The founder would pay his share of any “unfunded repayment obligations” at the end of the fund’s life, which runs 12 years with a two-year extension.

Son has deposited 8.9 million of his own shares as collateral for Vision Fund 2, and another 2.2 million shares as collateral for the LatAm fund, the company said in its disclosures. The stock will only be released once the receivables are settled.

Son’s net worth stood at $12.1 billion after Thursday’s close, after adjusting for his deficit from his interests in Vision Fund 2 and Latam fund, according to calculations by Bloomberg Billionaires Index.

SoftBank announced a record $23.4 billion loss for the June quarter on Monday, a staggering sum driven by the declining value of portfolio companies such as Coupang Inc., SenseTime Group Ltd. and DoorDash Inc. Son pledged to implement sweeping cost cuts at his conglomerate to shore up its finances, along with a more measured pace of investments.

Son is also selling off assets to raise cash and bolster his balance sheet. SoftBank expects to post a gain of more than $34 billion from selling a chunk of its stake in Alibaba Group Holding Ltd., its most valuable asset. He also said SoftBank has begun talks to sell Fortress Investment Group, the asset manager he acquired for $3.3 billion in 2017.

SoftBank shares rose about seven percent Friday in Tokyo trading after the Alibaba disclosure.

Compensation has long been a problematic issue at SoftBank. Japanese companies pay some of the lowest executive salaries in the world, in part because leaders tend to work their way up slowly from within. Son himself has kept his pay at 100 million yen, now roughly $740,000 — a rounding error in the US where CEOs routinely make more than $100 million.

But SoftBank’s parsimonious pay led to problems as Son repositioned his telecom company into the world’s largest technology investor. He hadn’t set up the kind of deal-by-deal “carry,” or profit sharing, that startup investors typically get, leading to a near-constant stream of defections.

Most recently, two more managing partners are leaving the Vision Fund, bringing the number of top-level departures from the organization to at least 10 since March of 2020. Rajeev Misra, the long-time head of the Vision Fund, is giving up most of his titles and responsibilities as he starts his own investment fund.

To boost compensation, SoftBank increasingly allowed executives to cut side deals by which they benefit personally alongside the company’s activities. Misra, for example, borrowed $463.5 million from SoftBank to invest in T-Mobile US Inc., the telecom firm that bought SoftBank’s Sprint Corp. in 2020. Marcelo Claure, the now-departed chief operating officer, also borrowed $515 million, according to company filings.

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Son led the way in cutting deals for himself. In 2020, he revealed that he would take a one-third share of SB Northstar, which was set up to buy stocks like Amazon.com Inc. and to trade highly leveraged derivatives.

Analysts and fund managers complained to Son at the time that the structure would lead to corporate governance concerns. Son denied there was a conflict of interest and described it as remuneration for his investment expertise. Other fund managers charge fees, he said, a person familiar with the matter said at the time. Son added that SoftBank’s board cleared the structure in a vote from which he recused himself, the person said.

Son’s expertise has not worked out well since. He unveiled the original $100 billion Vision Fund with the idea of backing the world’s startups, then followed it up with a smaller second Vision Fund. But the unprecedented bet on fledgling companies backfired with missteps like WeWork Inc. and then a sharp downturn in valuations.

Vision Fund 2 reported a 1.32 trillion yen unrealized valuation loss in the second quarter, led by declines at WeWork and AutoStore Holdings Ltd. The LatAm funds had a loss of 325 billion yen.

Son’s interests in Vision Fund 2 and the Latam fund were structured so the billionaire didn’t pay cash up front for his 17.25 percent stakes. Son is obligated to pay three percent on the “unpaid equity acquisition amount” until repayment, an interest that has been wrapped into his liabilities.

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“The investment company losses hurt (no one wants to lose a billion dollars) but not as much as the valuation loss in his Softbank shares which are down 50 percent from the all-time high,” said Kirk Boodry of Redex Research who publishes on SmartKarma. “That is a $22 billion decline.”

In a press conference after earnings this week, Son was sombre and said he bore responsibility for the company’s mistakes.

“We really believed we could do it and we had our heads in the clouds,” Son said. “Of course, the market was bad, there was a war, and there was the coronavirus. We can point to a lot of reasons, but these are all excuses. We have to self-reflect about the fact that if we’d been more selective and had invested more properly, it wouldn’t come to this.”