Even in Silicon Valley, a place teeming with entrepreneurs where fortunes are made seemingly overnight, Ryan Breslow stands out.

He has promised to shake up the boring but important business of online payments with Bolt Financial, the startup he founded eight years ago at 19. He has fashioned himself into a fundraising maven. Forbes magazine put him on a recent cover, estimating his net worth at $2 billion.

Breslow’s charm and vision captivated investors, allowing Bolt to raise funds at a blistering pace. From Peter Thiel’s fund to BlackRock, blue-chip investors have put in nearly $1 billion, drawn to Bolt’s technology — essentially, a version of Amazon’s “Buy Now” button that can be plugged into an online merchant’s website, making checkout a breeze.

In just over three years, Bolt has soared in valuation to $11 billion from $250 million, making it a Valley success story. “There’s almost a cult of Ryan” at Stanford University, which Breslow attended, said Trevor Traina, an early investor in Bolt.

But Bolt’s meteoric rise has been fueled at least in part by a pattern of stretching the truth, according to interviews with more than 50 former and current employees, clients, investors and others with whom Bolt discussed partnerships and fundraising, as well as a lawsuit filed recently by a big customer. Most of them sought anonymity because they were not authorized to speak publicly.

In a rush to show growth, Bolt often overstated its technological capability and misrepresented the number of merchants using its service, some said. In presentations to investors, it included the names of customers before verifying whether those merchants were able to use its technology. For a time, a fraud detection product it was pitching to merchants was more dependent on manual review than Breslow implied.

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Breslow, 27, abruptly stepped down as CEO in January, blind-siding some investors who just weeks earlier had put money into Bolt at an $11 billion valuation.

Now Bolt’s troubles are mounting. Some investors are looking to sell their stakes, while customers are questioning Bolt’s technology. One of Bolt’s biggest customers, Authentic Brands Group, which owns and licenses brands like Brooks Brothers, is suing the company for having “utterly failed to deliver on the technological capabilities that it held itself out as possessing.”

Breslow declined to be interviewed for this article.

Hilary Neve, a Bolt spokesperson, said that the company was proud of its technology and that the vast majority of its customers were thrilled with their partnership with Bolt.

Using the gut to spot fraud

While attending Stanford, Breslow and his friends mined bitcoin out of their dorm rooms, but he dropped out to start Bolt in 2014 with a fellow student, Eric Feldman, who left the company five years later. Bolt started as a bitcoin wallet company but soon pivoted to e-commerce payments.

Breslow began to build software that would handle online payments for retailers, offering fraud protection and, later, an emerging technology that allowed customers to buy a product with a single click. Amazon already had the one-click technology but offered it only to merchants selling products on its platform. Bolt pitched a decentralized alternative: one-click checkout software that could plug into the existing payments platform of any business.

In 2018, Bolt began publicly pitching merchants on its fraud protection service. Breslow talked up Bolt’s algorithm for detecting fraud, saying that it additionally used “human review” when cases looked risky.

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Companies lose $20 billion to fraudulent transactions every year, according to Juniper Research. Fighting fraud is expensive — especially for small businesses — and Bolt offered to cover the cost of fraudulent charges, making it an attractive pitch.

In the beginning, risk analysts manually reviewed hundreds of transactions a day, according to a former employee with direct knowledge of the product. Analysts had access to enough transaction data to identify customers online and would sometimes approve or decline transactions based on their gut — such as by visiting their LinkedIn pages — rather than an algorithm, the person said. Bolt later began using its software to process more transactions automatically.

Employees were encouraged to approve transactions even when they looked risky, which contributed to large losses for Bolt, former employees said. But the approach kept merchants on the platform, which was important because Bolt used its merchant count as a key metric in fundraising.

Neve of Bolt said in her statement that it was “false or misleading” that employees were encouraged to approve risky transactions but said that losses, which were expected, have gone down.

Building the business

Bolt’s sales team sometimes signed deals without always verifying that the merchant’s payments technology would be able to integrate with Bolt.

An internal document viewed by the Times laid out what to do if a merchant asked whether Bolt’s technology could integrate with its e-commerce platform. “If it’s a big merchant, you probably want to act like our integration is already underway, not lie about it being done, but act as if it’s close,” the document said. “If it’s a smaller merchant, gauge how much we want them vs how excited they are. If we want them a lot and they’re not absolutely ecstatic, then act as if we’ll build it.”

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Neve said the company could not locate the document but that it does not reflect “the practices or policies of Bolt.”

In 2018 and 2019, Bolt raised $71 million from investors in stages, at valuations ranging from $250 million to $357 million, according to the company. The money allowed Bolt to hire more employees, who began to sort out which clients would actually be able to go live. It also honed its fraud detection algorithm, which was now being used to review most of the transactions that came through its system.

In the summer of 2020, Bolt raised money at a $425 million valuation. Months later, it raised another $75 million.

In 2020, Bolt also struck a strategic partnership with Authentic Brands Group — a big get, since Authentic Brands owns more than 30 retail brands, including Forever 21, Lucky Brand and Brooks Brothers, and licenses their use to others.

Although only Forever 21 and Lucky used Bolt’s technology, Bolt would often cite Authentic Brands’ total revenue of more than $14 billion in its marketing materials. For instance, Brooks Brothers does not use Bolt but was cited on Bolt’s website as recently as April 25.

In November 2021, Authentic Brands sued Bolt, saying the startup used the bigger company’s brand to raise money. It said that Bolt failed to deliver a free shipping service for shoppers across its merchant network that would have been similar to Amazon Prime. The complaint also alleged that problems with Bolt technology cost Forever 21 $150 million in sales and prevented Brooks Brothers from using Bolt’s products — all while Bolt used the company’s brand, implicitly or explicitly, to raise money.

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In its motion to dismiss the suit, filed March 18, Bolt said Authentic Brands was trying to rewrite its contract so that it could purchase shares of Bolt at a discounted price. Bolt disputed which elements of the subscription product it needed to deliver by the deadline. It did not deny that it had used the brand but argued that investor presentations did not legally count as advertising and that listing Brooks Brothers on its website did not imply that the retailer was a customer.

New pitch

Beginning last summer, as he continued his push to raise funds, Breslow began telling investors that Bolt was now targeting shoppers in addition to merchants.

Bolt’s one-click checkout would become the predominant way to pay for the next generation, Breslow told investors. Rather than creating accounts with individual merchants, shoppers would hop between online merchants using their Bolt accounts, paying with a single click, since their credit card and other data were already uploaded.

Breslow urged investors to value the company on the basis of the 5.6 million shoppers who were signed on to Bolt’s network, rather than just the roughly 250 merchants using its service, according to the pitch deck.

Investors lapped it up.

In 2021, Bolt raised $333 million at a $4 billion valuation. A bigger jump came in January, when Bolt raised $355 million at an $11 billion valuation from investors.

Since January, Bolt has approached other investors to gauge their interest in putting money in at a higher valuation of $14 billion, according to three people with knowledge of the outreach. Neve said the company is not currently fundraising.

Shortly after Bolt closed its January funding round, Breslow went on Twitter to accuse Stripe, Y Combinator and top investors of conspiring to lock entrepreneurs like him out of fundraising. He said venture capitalists would express excitement at his “game-changing” product, only to “mysteriously” back away later.

Then, Breslow decided to step down as CEO of Bolt, but remains its executive chair. Breslow has co-founded a new company in Miami to let people fund clinical trials, Neve said.