Ryan Breslow seeks up to $27M pay-to-play bridge round to save Bolt

Ryan Breslow, the entrepreneur who returned as CEO of Bolt last year after years of legal battles and clashes with investors, is raising a bridge round of up to $27 million for the checkout-processing startup he co-founded in 2014, he told TechCrunch. Bolt hit an $11 billion valuation in early 2022 before plummeting 97% to $300 million.

The capital is coming from existing investors and is structured as a convertible note that will convert to equity at a discount once Bolt closes a future funding round. It also includes a punitive pay-to-play provision: backers who don’t participate will lose a large portion of their equity in the company. According to a company press release, the financing is meant to let Bolt capitalize on its recent operational milestones, clear legacy obligations, and ensure a smooth transition as it works toward closing a full Series E2 round.

Breslow declined to disclose how much cash Bolt has left, though he claims the company is nearing profitability and returning to growth after years of shrinking revenue. He is personally committing $5 million to the round and estimates participation from Bolt’s roughly 100 investors will total at least $15 million, though he said not everyone is expected to join. “I believe in Bolt more than anyone could possibly imagine. I believe Bolt is worth saving,” he said.

The new round comes two years after Breslow attempted a $450 million raise at a $14 billion valuation, a deal that collapsed after existing investors, including BlackRock and Hedosophia, sued to block it, following revelations that one investor named as a lead backer denied participating at all and another had offered $250 million in “marketing credits” instead of cash. That lawsuit was later voluntarily dismissed. Breslow said that, unlike the failed round, Bolt’s board and a majority of preferred shareholders have signed off on this fundraise, and at least one angel investor has confirmed plans to participate.

Breslow maintains Bolt would be in a stronger position today had he continued running the company during the three years he was away, and says the startup lost customers in his absence. He is betting on the “super app” Bolt introduced last year, which combines financial services, peer-to-peer payments, crypto, and credit cards into a one-click checkout. Despite shrinking headcount from 900 employees in 2021 to about 60 today, Breslow says AI is letting the company operate far more efficiently.

Why it matters

A pay-to-play bridge round is typically a sign a startup is running low on options, and Breslow’s bet that Bolt’s remaining investors will keep funding a turnaround — rather than write off the company — will determine whether it gets another shot at its stalled Series E2.