Bolt Financial, a startup specializing in e-commerce software, is seeking a $450 million Series F funding round, aiming for a $14 billion valuation, which marks a significant recovery from a previous low. Ryan Breslow, the company's founder and former CEO, is set to return to the helm, proposing controversial terms that include a $2 million bonus and $1 million in back pay. The funding round includes unusual 'pay-to-play' provisions that could force existing shareholders to invest more or risk losing their stakes. Despite raising nearly $1 billion in previous rounds, Bolt has faced challenges such as lawsuits and internal conflicts, leading to multiple layoffs and a drop in investor confidence. The latest deal, which has raised eyebrows among investors due to its aggressive terms, requires approval from a majority of shareholders by the end of the week. Bolt's fluctuating valuation and Breslow's contentious past highlight the precarious nature of startup funding in today's market.