Checkout startup Bolt is raising a $27 million bridge round featuring a 'pay-to-play' provision as CEO Ryan Breslow attempts to stabilize the company.

Bolt co-founder and CEO Ryan Breslow is raising up to $27 million in new bridge financing to support the checkout processing startup. The round is structured as a convertible note and includes a 'pay-to-play' provision, which penalizes existing investors who choose not to participate. Breslow, who returned as CEO in March 2025, is personally contributing $5 million to the effort as the company works toward a future Series E2 funding round.

Financial Structure and Investor Participation

The bridge round is designed to provide short-term capital for Bolt until it can secure a larger funding round. Breslow estimates that participation from the company’s approximately 100 existing investors will reach at least $15 million. Unlike a previous attempt to raise $450 million in 2022, which collapsed amid investor lawsuits and disputes over deal terms, this current round has received approval from Bolt’s board and a majority of preferred shareholders.

Operational Changes and Future Outlook

Bolt has undergone significant downsizing, reducing its headcount from 900 employees in 2021 to approximately 60 today. Breslow attributes the company's ability to maintain productivity despite the smaller staff to the integration of AI tools. While the company's valuation previously reached $11 billion in early 2022, it has since fallen to $300 million. Breslow claims the company is nearing profitability and is focusing on a 'super app' that integrates financial services, crypto, and credit cards into its checkout platform.