A digital bank that raised $110 million from investors including Leonardo DiCaprio has run into trouble

Key Points
  • The digital bank Aspiration has had difficulty closing its most recent funding round, according to people with knowledge of the matter. 
  • The company laid off 15% of its employees last month and has been withholding some payments to vendors since at least the summer, these people said. 
  • "This is a company that would've gotten funded a year ago," said a fintech CEO who requested anonymity to speak frankly.
A celebrity-backed digital bank is now scrambling to find funding
A celebrity-backed digital bank is now scrambling to find funding

A digital bank that raised $110 million from venture capital funds and celebrities including Leonardo DiCaprio is scrambling to find funding, a potential sign that investors are cooling on risky start-ups after the WeWork debacle.

At first blush, Aspiration has all the trappings of a successful disruptor.

Part of a new breed of online-only banks, the Los Angeles-based start-up has celebrity backers including DiCaprio and Orlando Bloom, rapid growth and a trendy socially responsible model that brought it plenty of media coverage.

In April, Aspiration CEO and co-founder Andrei Cherny told Reuters he was seeking a round "larger than anything we've done before." The article cited an anonymous source saying the company wanted at least $200 million and a $1 billion plus valuation.

But Aspiration, which allows its customers to choose how much they pay for services, has so far failed to persuade enough investors to participate in its latest fundraising round, according to people with knowledge of the situation. Last month, the company laid off 15% of its employees and has been withholding some payments to vendors since at least the summer, these people said.

The start-up may have been caught in a shift as previously high-flying unicorns slammed into the reality of public markets. The disappointing Uber IPO in May and the collapse in WeWork's valuation in September has meant that money-burning companies with a murky path to profitability are finding it harder to secure funding. What may be unfolding is the first sign of a painful adjustment for unicorns or companies seeking that status.

"This is a company that would've gotten funded a year ago," said a fintech CEO who requested anonymity to speak frankly. "What you're seeing is VCs becoming more discerning about the outcomes on latter-stage rounds. If you're going to fund something at a $1 billion valuation, are you sure you can get a $3 billion valuation in an IPO?"

For so-called challenger banks like Aspiration, the problem is exacerbated by an increasingly crowded field. Chime and Varo have gained in popularity, investing start-ups like Betterment and Stash now offer checking accounts, and U.K.-based competitors Monzo and Revolut are coming to the U.S.

CEO response

In an emailed response to this article, Cherny said Aspiration had raised more than $50 million this year, with more coming in commitments.

"More than 1.5 million Americans have signed up with Aspiration to start making the move to spending and saving with a conscience," Cherny said in the statement. "During the past year, Aspiration has seen phenomenal growth in customers and revenue. Anyone saying otherwise doesn't know the facts."

He added that "prudent cash management and changing up your team structure is part of being a startup."

While Aspiration has taken steps to conserve cash, that doesn't mean that it is financially distressed, according to a person involved with the start-up who didn't want to be named. The job cuts last month were tied to a major project that was completed, this person said. The company also recently hired two senior staffers – a general counsel and a chief business officer – and is planning several product launches, which this person cited as evidence that Aspiration was still in growth mode.

Still, the Series C round mentioned in the April Reuters article has yet to be closed, and that's unlikely to happen before year-end, this person said. The $50 million raised this year is a combination of equity and convertible debt, the person said.

Irate vendors

Aspiration employees started getting antsy this summer as news of fresh funding failed to materialize.

At the same time, concern over the company's funding spiked as irate vendors called Aspiration's customer service line or appeared in person at the firm's Marina Del Rey, California, headquarters to demand payment, according to former employees. Vendors even reached out to employees on LinkedIn, asking if Aspiration was still in business. The vendor complaints became so pervasive that most of the company's acquisition team quit, the ex-staffers said.

Then, about two months ago during an all-hands company meeting, managers insisted that it was "normal" to not pay some vendors, the ex-workers said.

One vendor, a Los Angeles-based recruiter who didn't want to be named until pending litigation was settled, said Aspiration failed to pay him after he helped the company hire several top engineers.

"The last thing I want to be is another creditor in line in a bankruptcy," the vendor said, explaining why he filed a lawsuit seeking repayment. "Everyone over there wants out because they see the writing on the wall."

He was told by Aspiration that the company found some funding — a "partial round" — during the summer, because it paid half of what he was owed in August.

Then last month, Cherny terminated 31 of his 200 employees. Several who remain said they are actively searching for employment elsewhere.

Aspiration has several possible options to consider if it can't secure more funding, according to industry experts. Cherny could sell Aspiration to a strategic buyer like another fintech firm. (The April Reuters article was a signal that Aspiration was open to being bought, several venture capitalists said.) Or investors could offer him a rescue line of debt financing that would convert into a majority equity stake if performance metrics don't improve.

Many start-ups have hit turbulent periods before going on to become successful, and that's entirely possible at Aspiration, according to an investor in the company.

As with many fintech start-ups, customer deposits are kept at separate FDIC-insured institutions; Aspiration listed eight partner banks that held users' money.

'The bubble will burst'

But the larger issue is that for too many start-ups, the cost to acquire customers is "dramatically greater" than the economics they provide, said Ben Cukier, a fintech investor with Centana Growth Partners.

As investors around the world sought yield, some of those dollars made its way to venture capital funds, including Softbank's Vision Fund. Some investors accepted shaky metrics tied to growth and start-ups gamed their businesses accordingly instead of creating sustainable operations, according to Cukier and others. Fintech start-ups took in a record $39.57 billion from global investors last year, more than double the 2017 figure, according to CB Insights.

"I think the bubble will burst or at least slowly deflate," Cukier said in a phone interview.

"There's certainly going to be consolidation" along with failures, Cukier said, adding that he had no knowledge of the specifics of Aspiration's situation and he didn't know when the broader reckoning would occur.

"To some extent, tying two drunks together [in a merger] and hoping they walk straight is not what I call a feasible long term strategy," he said.

For Aspiration's ex-employees, the real disappointment is that everyone from Cherny on down seemed genuinely invested in the firm's mission: to provide a socially conscious, sustainable alternative to the big banks.

Co-founded in 2014 by Cherny, a former Democratic speechwriter for Al Gore, Aspiration provides "fossil-fuel free deposits" and gives 10% of what it earns to charities. That approach helped it snag DiCaprio as an investor and adviser.

"This really could've worked," an ex-employee said. "The people I worked with were insanely talented. They really could've changed finance."