STRIPE, one of the world’s most valuable startups, told investors it plans to use money it receives in its latest round of fundraising to help cover a roughly US$3.5 billion tax bill.

Using an illustrative valuation of US$55 billion, the payments giant said it is looking to raise about US$2.3 billion to cover tax withholdings in the first quarter, according to an investor document seen by Bloomberg News. It plans to withhold an additional US$500 million and US$700 million in taxes later this year and next year, respectively.

The company also expects to use US$600 million of the fundraising to exercise some employees’ options, according to the presentation, handed out to wealthy clients of Goldman Sachs Group.

A spokesperson for Stripe, which has dual headquarters in San Francisco and Dublin, declined to comment. Goldman representatives didn’t immediately respond to a request for comment.

The document shows just how much Stripe is looking to raise from investors in the coming weeks as it continues with a fundraising push it started in January, when it hired investment bankers at Goldman Sachs and JPMorgan Chase & Co as it evaluated options to raise cash or go public. In recent talks with investors, the company has discussed a US$50 billion valuation, compared with the US$95 billion valuation it received when it last raised cash from outside investors.

Throughout the fundraising, Stripe has been adamant with investors that it doesn’t need the cash to fund normal business operations. Rather, at the centre of Stripe’s quest for cash are the company’s so-called double-trigger restricted stock units. For years, the company handed out the units to attract and retain talent.

GET BT IN YOUR INBOX DAILY

Start and end each day with the latest news stories and analyses delivered straight to your inbox.

Sign UpVIEW ALL

Normally, employees given such shares have to clear two hurdles for them to pay out: First, the shares have to vest. Second, the company has to have a liquidity event such as an initial public offering so they can sell their shares. Whenever that happens, the employee faces a higher personal tax liability, and they can use the proceeds from the sale of their shares to cover it.

But equity capital markets have been largely shut for months, making it hard for Stripe to make its public debut. Now the company is facing a looming issue. Many of Stripe’s earliest employees’ shares could soon expire unless the board waives that second trigger. But doing so would leave employees suddenly facing the higher personal tax liability without having a way to sell shares to pay for it.

The document shows that Stripe has two goals for its latest round of fundraising: raising enough money to cover the looming tax bill that early employees will soon face, then organising a tender offer to allow those staffers to sell at least some of their shares.

Some elements of Stripe’s plans to cover tax obligations through its fundraising efforts were previously reported by The Information.

Winning competitions

In the presentation, Stripe said it generated US$14.3 billion in revenue as it processed US$816 billion in payments volume last year. The company’s so-called transaction margin before losses — a measure of net revenue — rose to US$3.17 billion, or 0.38 per cent of total volume. That compares with 17 basis points for rival Adyen, according to the presentation.

“Secular market-share trends favour Stripe and other tech-forward competitors,” Stripe said in the document. “Payments growth is not a zero-sum game.”

The company said it wins about 44 per cent of new opportunities it competes for, and just 9 per cent of potential business go to a competitor. The remaining 47 per cent “represent opportunities where prospect abandoned process or where reliable data on the ultimate outcome is unavailable”, Stripe said.

The company also touted newer efforts, including its issuing business. That unit, which allows Stripe to compete with other startups such as Marqeta, offers customers the ability to create a commercial-card programme.

The business is on track to earn US$127 million in transaction margin before losses by 2024, up from US$37 million last year, Stripe said in the presentation. BLOOMBERG