Ryan Breslow

Once Silicon Valley royalty (Breslow changed his middle name to “King” in 2021), the cofounder and chairman of payment startup Bolt was one of the world’s youngest billionaires when investors including BlackRock and H.I.G. Growth valued Bolt at $11 billion in early 2022. It all unraveled over the following 18 months, between acrimonious lawsuits and early backer Activant alleging that Breslow forced out board members who questioned a plan for Bolt to reimburse Bolt for a $30 million loan he had taken out years prior. Bolt’s value crashed, and the company bought back shares from investors and employees at a 97% markdown in January 2024, suggesting a $300 million valuation. 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. Breslow dropped out of Stanford University to build a Bitcoin wallet startup. Mr. Breslow has become something of a legend in the Valley, for his fund-raising prowess and his outspoken behavior. In just over three years, Bolt has soared in valuation to $11 billion from $250 million, making it a Valley success story. Mr. Breslow abruptly stepped down as chief executive in January 2022, blindsiding some investors. One of Bolt’s biggest customers, Authentic Brands Group, which owns and licenses brands like Brooks Brothers, is suing the company. Bolt has around 800 employees. An expected partnership with Shopify — which Bolt hoped would bring much of its future revenue — never came about, and Bolt had to stop processing payments for merchants using that platform.