The 27-year-old billionaire takes on the elite of Silicon Valley

Bolt is one of many companies trying to simplify the online checkout process. Since 2017, when Amazon’s patent on one-click payment expired, there’s been a race to bring the feature to the rest of e-commerce. Many merchants see an urgent need for this service: online carts are abandoned around 70% of the time in transactions that require more than one checkout step.

Breslow, a Miami native, co-founded Bolt in 2014, just two years after his freshman debut at Stanford University, envisioning a company that would enable digital currency payments. The company eventually turned to regular purchases. In addition to offering fast checkouts, Bolt’s software allows shoppers to purchase items from any page, not just the shopping cart page, and helps businesses collect data. The startup does not charge merchants for using its software, but earns money every time a buyer who has already signed up for Bolt’s system checks out. Bolt’s take on business is that the startup will only make money when it does.

In Bolt’s early days, fundraising was a challenge, as was hiring engineers and trying to get media attention. “It was brutal,” Breslow said. He winces as he recounts the two times Bolt nearly ran out of money and had to cobble together small checks from a group of investors. “Sand Hill Road would not invest in my business,” he said. “I went to the four corners of the earth to find capital.”

Venture capitalist Marc Andreessen criticized Breslow’s four-day work week. Credit:Bloomberg

Eventually, Breslow raised money from major New York companies, including funds managed by BlackRock, General Atlantic, and Dan Och’s Willoughby Capital. He hired Matt Mochary, a CEO coach who has mentored founders including Brian Armstrong of Coinbase Global. Breslow self-published two books, Fund raising and Recruitment. And he learned to attract attention. In September, Bolt launched a four-day work week, which Breslow said would allow every employee to work “like a lion, not like a cow.” The move drew a slew of positive stories.

As the company grew, Breslow also began tweeting more, mostly about management and startup tips, buying Twitter promotions to boost his profile. In January, Breslow tweeted: “Over the past 4 months I’ve taken everything I’ve learned in business and written threads. The result: 4,000 to 104,000 subscribers.” Asked about the Twitter ads, Bolt said he pays for distribution on company-related accounts and that “the majority of the growth has been organic.” Now, while Breslow’s profile has increased following his fundraiser and his incendiary tweets, he has 154,000 followers.

Some close to Breslow say they have become uncomfortable with his growing interest in self-promotion. A Bolt shareholder has called for the publication of a book titled Fund raising while in the midst of a “rash” fundraiser. And when Breslow took his Twitter anger out on Silicon Valley, several people around him privately expressed surprise at the tone of the tweets and concern at the backlash that followed.

Breslow, for his part, says he was emboldened after raising $355 million and securing an $11 billion valuation to finally vent the frustrations with traditional tech VCs that had been simmering for years. The money reached Bolt’s account the same week he tweeted. “That’s the point where we finally felt we didn’t need it,” he said. After receiving nearly $1 billion in total funding, he said it was clear “they couldn’t stop us.”


The biggest question mark for Bolt now is its high valuation relative to the revenue it generates, a closely watched metric that helps investors determine whether a company is overvalued. The startup doesn’t disclose its financial results, but according to two people, last year it took in around $40 million. (Two people familiar with the industry said they thought even that number seemed high, based on their understanding of Bolt’s market share.) With $40 million in sales, that would mean the multiple of Bolt’s earnings run into the hundreds — a big number even in a frenzied market for startup funding, where valuations often outpace real-world traction. For comparison, the public marketplace competitor Shopify Inc.’s projected revenue for 2021 is $4.57 billion, according to Bloomberg estimates, giving the company a multiple of 24.

Several private venture capital firms have stopped investing in Bolt due to its uncomfortably high valuation and unproven activity, people familiar with the talks said, and others have been put off by Bolt’s unorthodox style. Breslow.

At a time when Bolt should have become a Silicon Valley force, the company’s fundraising announcement ran into unusual difficulties. Bolt’s press release in January said BlackRock funds led the round, but in an odd twist, BlackRock did not lead the round, forcing Bolt to correct his statement. On Zoom, Breslow explained that it was an innocent mistake and easy to make since BlackRock had committed the most money. But two people familiar with the deal who asked not to be identified said BlackRock was not actually the biggest investor in the round. A Bolt spokeswoman said, “BlackRock is the biggest new outside investor. No further comment.

The idea of ​​stepping down as CEO came to Breslow while pondering, he said. In an interview with CNBC this week he said he came up with the idea after the funding round closed, although two people familiar with the situation said he told them he thought about it months ago. Regardless, some people involved in the funding round felt “blindsided” by the news, according to another person familiar with the situation.

As Breslow steps down as CEO to take on the role of executive chairman, Bolt is adding seasoned leaders to day-to-day roles. The new CEO is Maju Kuruvilla, 44, who served as Bolt’s chief technology officer and chief operating officer after leaving in 2020. He also added two other executives. Twitter’s head of human resources, Jennifer Christie, recently joined the company, as did Joanne Bradford, formerly chief marketing officer and chief operating officer of SoFi Technologies.

Ultimately, Bolt’s success will depend on how many big clients he can sign. Bolt and its competitors, like Shopify’s PeachPay and Shop Pay, try to create the largest possible pool of merchants and shoppers who use their software. “We all build networks of buyers and sellers,” said David Mainayar, one of the founders of PeachPay. “Networks are more valuable based on the number of people opting into the marketplace.” It’s a strategy similar to that of the credit card giants: retailers accept Visa because many consumers want to use it.

Bolt says it has 300 live merchants on its platform and aims to increase registered buyers from its current 12 million to 112 million by the middle of next year. Currently, however, its customer list is dominated by smaller regional retailers. One of the few notable exceptions is Forever 21, which is trying to bounce back from bankruptcy.

Bolt's fundraising press release in January said BlackRock funds led the round, but in an odd twist, BlackRock did not lead the round, forcing Bolt to correct his statement.

Bolt’s fundraising press release in January said BlackRock funds led the round, but in an odd twist, BlackRock did not lead the round, forcing Bolt to correct his statement.Credit:PA

According to people familiar with the matter, Bolt has spoken to major social media companies about using his service. These people told Bloomberg that the list includes Pinterest, which previously worked with Bolt, and discusses details of an ongoing relationship. Bolt also met with representatives from TikTok. Bolt, Pinterest and TikTok declined to comment. In the interview with CNBC this week, Breslow said he’s signed “huge deals” over the past six months.

Convincing more large companies to use Bolt could be difficult as other vendors offer more functionality at this stage, said payments industry consultant Richard Crone. That leaves Bolt a narrow path to reach his potential, he says. According to people familiar with the business, if his social media conversations are successful, Bolt could be on track for $160 million in annual recurring revenue within a year. But the process of defending the competition could be difficult: “Bolt is entirely dependent on beating all other types of wallets,” Crone said. “Do they have the components to pull it off?”

No longer CEO, Breslow is settling into his new role as executive chairman, where he says he will focus on his “superpowers”: closing deals and leading the company’s culture and vision. He created Conscious Culture, an organization dedicated to building a humane corporate culture, with Mochary as a founding partner. From Breslow’s home office in Miami, where he moved at the start of the pandemic, he says he still makes time to meditate and practice yoga every morning. He also says he dances every day, sometimes between meetings: “That’s how I feed my soul.”


Breslow says he took out a loan against his Bolt shares to start the non-profit dance association The Movement, offering free dance lessons. He credits San Francisco’s dance scene with an authenticity that he says is lacking in Bay Area tech. “I learned more about alumni leadership in dance than in a lot of tech circles,” Breslow said.

He also tried to give some of his trust to other founders, telling them they don’t need to curry favor with the powers that be in Silicon Valley. “Always remember that you are worthy,” he wrote in one of his books. “Money is plentiful these days.”


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