Masa Son's big tech dream is fading as more bets sour and key people leave

Hong Kong (CNN Business) SoftBank (SFTBF) founder and CEO Masayoshi Son wants to shape the future of technology for centuries to come, but that bold dream may be fading as his Vision Fund stumbles and investors press for much more focus on the present.

Son is expected to yet again defend his investing prowess Wednesday when SoftBank releases quarterly earnings, but it's becoming harder for him to explain away his company's biggest tech misfires.

While he has long argued that his company is in the best position to capitalize on the coming artificial intelligence revolution, it has become increasingly clear that some of Son's massive tech bets are not going to plan.

Losses among flagship start-ups in the $100 billion Vision Fund portfolio are mounting. An activist investor is pressing for changes at the firm. Staff are heading for the exits amid the deluge of bad news. And plans for a second mega fund are reportedly running into trouble with investors.

Losses are piling up for the Vision Fund

SoftBank has had a rough few months.

In November, the company revealed that the Vision Fund and one of its affiliates had taken a $9 billion hit as investments in WeWork, Uber (UBER), Slack (WORK) and other major startups soured.

In December, SoftBank abandoned its investment in dog walking company Wag, a $300 million bet that many had questioned in the first place.

And last month, India's top hotel company OYO — one of the biggest startups in the Vision Fund portfolio — said it was slashing jobs and warned that more layoffs could be on the way as it scrambles to turn a profit. The Vision Fund has pumped more than $600 million into OYO to date, according to Chris Lane, an analyst with Bernstein.

Son's "belief in the disruptive force of AI pushes him to want to allocate as much capital [as] possible to gaining footholds into the future," Lane wrote in a note this week. "But markets are much more short term and need to see evidence of a greater commitment to near term returns."

Bernstein maintains that despite the losses from WeWork, Uber and other investments, SoftBank is deeply undervalued. The firm pointed out that the Vision Fund generated a rate of return of 24% through September 2019.

But there have been additional signs of strain.

On Monday, Brandless became the first Vision Fund-backed startup to shut down. The direct-to-consumer company is halting operations, cutting 90% of its staff and will stop accepting online orders, according to a Brandless spokesperson.

"Brandless set a new standard in the wellness and sustainable products industry, and while we weren't able to compete competitively in today's [direct-to-consumer] market, I'm confident the next great brands of tomorrow will be built from this experience," Brandless CEO Evan Price said in a statement.

The Vision Fund declined to comment on Brandless shutting up shop. It led a $240 million funding round for the company back in 2018.

Under scrutiny from a legendary activist investor

Jefferies analyst Atul Goyal has doubts whether SoftBank can regain in 2020 what it lost in 2019: Its reputation.

SoftBank's roughly $10 billion bailout of WeWork set a bad precedent, according to Goyal, because the rescue signaled Son's firm is willing to throw good money after bad projects.

SoftBank will continue to suffer if it's "unable to explain how it will limit risks from future investments that fail" and "unable to show financial discipline in its investments," Goyal wrote in a research note in December.

Legendary activist investor Elliott Management wants to see SoftBank exercise some discipline, too.

The New York-based fund revealed earlier this month that it has built a "substantial" stake in SoftBank, and said it has held private talks with SoftBank leadership — including Son — aimed at making changes to improve performance at the Japanese firm.

Elliott's position effectively turns the tables on SoftBank, which has long wielded vast power through the mega Vision Fund. Now, SoftBank is the one under pressure from an influential investor.

SoftBank's corporate governance has also seen a shakeup since the company last reported earnings. In December, Uniqlo founder Tadashi Yanai resigned after 18 years on the board. That departure was perceived as "a major negative development," according to Lane, of Bernstein.

SoftBank's current board is comprised of 11 members, of which only two are classified as independent.

"Against nine other members all loyal to Masa it's questionable whether true independent debate is happening on key issues," said Lane. He added that Yanai was considered the only board member that had the independence and stature to push back on Son.

Key staff abandoning Vision Fund and potential investors are spooked

The Vision Fund has also been losing some key staff.

The Financial Times reported last week that top US executive Michael Ronen was leaving the Vision Fund after expressing concerns about "issues" at SoftBank. Ronen is one of five managing partners handling Vision Fund investments in the Americas.

Ronen, a former Goldman Sachs (GS) banker, joined the fund when it launched in 2017 and helped it grow from a staff of about 20 to 200. A person familiar with the matter confirmed Ronen is moving on, adding that his portfolio will pass on to other members of the team.

Ronen's departure follows that of partners David Thevenon and Praveen Akkiraju, both of whom left in the last few months.

With the slow and steady drip of bad news dogging SoftBank and its Vision Fund, Son's goal of forming a second mega tech fund is now in doubt.

SoftBank announced last July that it had signed more than a dozen agreements with companies such as Apple (AAPL), Foxconn Technology Group (HNHPF), Microsoft (MSFT) and Standard Chartered (SCBFF) to form Vision Fund 2, saying the anticipated amount of capital would be about $108 billion.

But many of those companies are reportedly now refusing to commit to the new fund, scared off by the WeWork debacle and the way the fund operates. The Wall Street Journal reported last week that Vision Fund 2 could end up being less than half its planned size, with nearly all of its capital coming from SoftBank itself.

A SoftBank spokesperson referred CNN Business to comments given to the US newspaper, saying the company had nothing further to add.

SoftBank told The Wall Street Journal that it could still attract outside cash, and expects money from some corporations. "Other investors continue to assess potential future commitments," a SoftBank spokesman told the newspaper.

Microsoft declined to comment on the matter. Apple, Foxconn and Standard Chartered did not respond to requests for comment.

"Let's stop putting numbers on it," Scott Galloway, marketing professor at New York University's Stern business school, wrote in a newsletter last month. "This is the first and last fund from SoftBank."

— Matt Egan and Rishi Iyengar contributed to this report.