Steve Ballmer invested nearly $10 million into Aspiration in March 2023, which followed his initial $50 million investment 18 months earlier, according to legal filings reviewed by The Athletic and corroborated by a former executive with the company. Ballmer’s $10 million investment came as Aspiration was quickly losing cash, laying off employees and struggling to raise funds.
The March 2023 investment by Ballmer followed a December 2022 investment of $1.99 from Los Angeles Clippers minority owner Dennis Wong. Wong is Ballmer’s college roommate and vice chairman of the Clippers.
A $1.75 million payment by Aspiration was made to Kawhi Leonard shortly after Wong’s investment.
The March 2023 round of fundraising had a target of $75 million, but they came up nearly $9 million short. Nearly all of the investors had previously invested into the company.
Leonard and the Clippers are under investigation for possible salary cap circumvention. Leonard received a no-show endorsement deal with Aspiration worth $28 million over four years. Leonard also received $20 million in stock.
Aspiration co-founder Joe Sanberg introduced the deal to the company, but it received scrutiny from executives as they believed it held little value.
“I am personally contributing stock to Kawhi to make this partnership possible,” Sanberg wrote members of his leadership team in a May 2022 email obtained by The Athletic. “Aspiration’s CEO judged the deal to be not worth doing. For avoidance of doubt, any and all benefit to Aspiration from the Kawhi deal is being subsidized by my contributing my equity to make this happen.”
Aspiration employees said that Sanberg built and maintained a relationship with Ballmer to convince him to invest in the company.