E-commerce startup Bolt wants to raise new money under aggressive terms that could make its once-ousted founder rich, reports say

• Bolt founder Ryan Breslow proposes returning as CEO with a $2 million bonus and $1 million back pay.
• Breslow left Bolt in 2022 due to investor conflicts and has since run wellness marketplace Love.
• The proposal includes terms that favor Breslow and his other venture.

Bolt's founder and ex-CEO wants to return to the driver's seat — and he's asking for a hefty payday to come back.

Ryan Breslow, who founded e-commerce software startup Bolt a decade ago, proposed a deal to investors this week, The Information and Eric Newcomer reported Tuesday.

The terms of the funding round were highly unusual, including a $2 million bonus for returning and $1 million in back pay for the two years he was away from the company, the outlets reported, citing a private equity partner who was involved in the deal. The partner has since said that his firm is no longer involved.

Breslow left the company in early 2022 because of conflicts with investors. The 30-year-old entrepreneur's career has been marked by controversy, including lawsuits, a fight with an early investor, and a public spat with competitor Stripe and Y Combinator.

Bolt's interim CEO Justin Grooms wrote in a letter to investors reviewed by The Information that the company was raising $450 million in a Series F round that would value Bolt at over $14 billion. According to Newcomer, Bolt's annualized run-rate revenue was $28 million, and its gross profit was $7 million.

The deal comes with several other eyebrow-raising clauses that would further benefit Breslow, reported Newcomer and The Information:

• Breslow would get an option to sell 10% of his shares and the right to purchase Bolt subsidiaries conscious.org and fourdayweek.com from the company for $1 at any time. Breslow had championed a four-day workweek .
• He would also get a new equity grant that would be "no less than the 90th percentile of CEO equity compensation packages of similar companies in Bolt's industry."
• If Bolt hits a $50 billion valuation in a $100 million or greater fundraise, Breslow would receive an additional stock grant of 5% of the issued and outstanding Bolt shares.
• The company would partner with Love, a wellness marketplace run by Breslow since he was ousted from Bolt.
• Bolt would invest $10 million into The London Fund, a venture capital firm that appears to be one of the main investors in its current funding round. The Information reported Breslow is a director at the fund, which also invested in Love.

Bolt's investors were also told that they would need to chip in more money for this funding round. If they fail to do so, Bolt would buy most of them out for one cent a share, a particularly aggressive "pay-to-play" move in the startup world, reported Newcomer.

The proposal requires approval from an investor majority, and shareholders have from late Monday to Wednesday to decide, reported The Information.

Bolt's prior investors include BlackRock, Sequoia Capital, Founders Fund, and Intuit, per PitchBook.

Neither Bolt nor Breslow immediately responded to Business Insider's requests for comment, sent outside standard business hours.