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The Briefing: Bolt’s Breslow Plots His Return

Bolt founder Ryan Breslow is proposing to return to the e-commerce startup in a bizarre deal that could squeeze out existing investors. Plus, Elon Musk’s legacy for his Twitter lenders.


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The Briefing
Bolt founder Ryan Breslow is proposing to return to the e-commerce startup in a bizarre deal that could squeeze out existing investors. Plus, Elon Musk’s legacy for his Twitter lenders.͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­
Aug 20, 2024

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You really can’t beat tech industry founders (and a few venture capitalists) when it comes to setting new standards of chutzpah. The latest example? As my colleague Erin Woo scooped today, Bolt founder Ryan Breslow is proposing to return as CEO of the once-hot e-commerce startup. He claims to have the backing of an overseas investor who would put up a couple of hundred million dollars while existing shareholders would be effectively forced out of the company.

There's no guarantee investors will go along with it, however, as we detailed here. Still, the proposal itself represents a bizarre turn of events, even for a company that has had its share of twists and turns (for a recap of past history, see here, here, here and here). Some will recall that Breslow stepped down as CEO in January 2022 after referring to Stripe and Y Combinator as “mob bosses.” Since then the e-commerce sector has cooled down and Bolt’s tiny business has stalled. Oh, and Breslow engaged in some sharp-elbowed wheeling and dealing to retain control of his baby.

You might have thought Bolt was destined to be another ZIRP-era startup that fell by the wayside. That may still turn out to be the case, but Breslow is determined to paint a different picture. Bolt’s interim CEO, Justin Grooms, sent a letter to investors on Monday revealing Breslow’s proposed return and claiming that a new fundraising had valued Bolt at $14 billion—above its peak 2021 valuation. That number makes absolutely no sense, by the way, and readers should take it in with a truckload of salt. 

The cherry on top of this baked good was the assertion by interim CEO Grooms that “e-commerce is evolving rapidly and we must lead the charge or risk becoming obsolete.” With that in mind, Breslow plans to launch a “superapp” to integrate everything from one-click buying to shopping to financial services. Hmmm. 

This is a letter from this week, not 2021, although you could be forgiven for any confusion. Aside from the overhyped language, superapps were a hot concept a few years ago, attempted unsuccessfully by companies ranging from PayPal to Klarna and (more recently) Elon Musk’s X.

Whatever the outcome of Breslow's latest gambit, it seems time for an enterprising filmmaker to pitch a series based on the saga. It could be called “Bolt Action.” So who should play Breslow?

Bolt’s investors aren’t the only ones with regrets. As The Wall Street Journal reminded us today, the banks that loaned $13 billion to Elon Musk for his Twitter buyout in 2022 have not done well. They’re still holding the loans, unable to sell them.

The Journal cited data from PitchBook to suggest the deal was the worst for banks since the 2008–09 financial crisis. It’s been such a disaster that some bankers had their pay slashed last year as a result, the report said. You have to wonder—what happens when the next overhyped mogul tries to borrow money for an overpriced deal?

  • Publisher Condé Nast, the owner of magazine titles including Vogue, The New Yorker and GQ, has struck a multi-year licensing deal with OpenAI, the company’s CEO, Roger Lynch, announced in a memo to staff (more here). 
  • Alex Cooper signed a deal with SiriusXM for her popular “Call Her Daddy” podcast, as well as her network of other shows (more here).
  • State Street, the Boston-based custody and financial services giant, has tapped Swiss startup Taurus as a technology vendor for its digital assets services (more here).

AI Agenda by Stephanie Palazzolo separates hype from reality and explains how AI is transforming industries. The 4x/week newsletter details the innovation and disruption happening in AI, from the AI startup funding frenzy to the major technological breakthroughs that will set the agenda for decades to come. Sign up today.

Some call them plagiarism bots, while others see them as a new capital asset that will change economies and societies. Some call them stupid, while others believe it’s stupid not to recognize their full potential. So what’s the right way to think about large language models? This summer, The Information surveyed our readers in collaboration with Comcast NBCUniversal LIFT Labs to understand their perspective LLMs. Read up on the insights they provided here.

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