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Ryan Breslow, the controversial entrepreneur who returned as CEO of Bolt last year after years of legal battles and clashes with investors, refuses to give up on the checkout processing startup he co-founded in 2014. The company, which hit an $11 billion valuation in early 2022 before plummeting 97% to $300 million, is now raising a bridge round of up to $27 million, Breslow told TechCrunch. Bridge rounds are short-term financings meant to tide a company over until its next major fundraise. The capital is being raised from existing investors and structured as a convertible note, meaning it will turn into equity at a discount once Bolt closes a future funding round. It also includes a punitive “pay-to-play” provision, meaning backers who don’t participate will lose a large portion of their equity in the company. Although Breslow didn’t frame it as such, the new financing may be the company’s last shot at survival. “This financing allows us to capitalize on our recent operational milestones, clear legacy obligations, and ensure a seamless transition as we progress toward the closing of our full Series E2 round,” according to a company press release. Breslow did not respond to requests for comment on what constitutes those legacy obligations. Startups generally raise bridge financings in two situations: when they are performing well and need six to 12 months to hit their next milestone, or when they are running low on cash and need time to restructure or reach profitability. Breslow declined to disclose how much cash Bolt has left, though he claimed the company is nearing profitability and returning to growth after years of shrinking revenue. While it is not clear if Bolt is indeed running out of capital, Breslow is clearly determined to see the startup he founded 12 years ago, at age 19 as a Stanford dropout, survive. “I believe in Bolt more than anyone could possibly imagine. I believe Bolt is worth saving,” he told TechCrunch. Breslow is personally committing $5 million to the round to demonstrate his belief in the company. Whether Bolt’s backers share that confidence — and help it hit its fundraising target — remains to be seen. Breslow estimates that participation from Bolt’s roughly 100 investors will total at least $15 million, though he noted not everyone is expected to join in. Breslow told TechCrunch shortly after being reinstated as Bolt’s CEO in March 2025 — three years after stepping down from the role — that he was in “early conversations” about a new round. Ultimately, bringing the company to a point of a publicly announced fundraise took more than a year. The new financing comes two years after Breslow attempted a $450 million round at a $14 billion valuation. That deal collapsed after existing investors, including BlackRock and Hedosophia, sued to block it, following revelations that one investor named as a lead backer of the round denied participating at all and another had offered $250 million in “marketing credits” instead of cash. (The lawsuit was later voluntarily dismissed by all parties.) Breslow says that unlike the failed $450 million round, Bolt’s board and a “majority of preferred” shareholders have signed off on the new fundraise. While he didn’t disclose how many of Bolt’s nearly 100 existing investors will double down, at least one angel backer, who asked not to be named, confirmed through his wealth manager that he plans to participate in the round. Breslow maintains that Bolt would be in a much better position today had he continued running the company from 2022 to 2025, saying that the company lost customers when he was not at the helm. He remains convinced he can restore Bolt to its former glory, telling TechCrunch, “I think we can be the Lyft to Stripe’s Uber.” Breslow is betting on the growth of the “super app” Bolt introduced last year, which integrates financial services, peer-to-peer payments, crypto, and credit cards into a one-click checkout. Despite shrinking its headcount from 900 in 2021 to about 60 today, Breslow claims AI is allowing the company to operate far more efficiently. “We’re getting probably 10 times more done, shipping 10 times faster because of AI,” he said. While running Bolt today is difficult, Breslow refuses to throw in the towel, arguing the company has a moat that would be impossible to replicate from scratch. Unlike other founders of fallen unicorns, Breslow isn’t ready to walk away and launch something new, even though he has been offered that option. “I have friends who said, ‘Ryan, I’ll give you $10 million to start a new company. You don’t have to deal with this turnaround and this nightmare of a situation with Bolt,’” Breslow said.
document fetched 2026-09-01 02:49 · canonical https://techcrunch.com/2026/08/31/ryan-breslow-is-raising-up-to-27m-in-pay-to-play-bridge-funding-to-save-bolt