Following his fiery Twitter tirades, Bolt founder Ryan Breslow is no longer CEO — and he says it’s his choice

Ryan Breslow, who founded the “one-click” checkout tech company Bolt as a Stanford student and dropped out of college to build it, is stepping away as the company’s CEO seven years into his reign. Breslow, who says the decision is his own, is being replaced as CEO by Maju Kuruvilla, who joined the company as its chief product and technology officer in 2019 and became its COO in August of last year. Breslow is assuming the role of executive chairman.

On its face, the decision would seem to make sense for the 600-person company, which is currently raising a round of funding that is expected to value the outfit at $14 billion, up from the $11 billion valuation it was assigned just earlier this month when it closed on $355 million in Series E funding.

Bolt — which earlier this month decided to give employees a four-day work week permanently — has raised nearly $1 billion altogether to date.

In Kuruvilla, Bolt gets some serious operational chops. He previously spent seven years at Amazon, the last three of them as a vice president and general manager, helping to scale Amazon’s worldwide Prime logistics and fulfillment business. Kuruvilla also worked previously on products at Microsoft, Honeywell, and Milliman. Put another way, he may be viewed as a safe bet by potential business partners, private investors, and, ultimately, if the company later attempts to go public, investment bankers.

Of course, it’s easy to wonder how closely the move is also tied to the attention that Breslow, 27, attracted after publishing a series of tweets last Monday afternoon and who was back at it this past weekend.

YCombinator is not worth it, a thread:

— Ryan Breslow (@theryanking) January 29, 2022

In what he described in his first series of tweets as a kind of public service to other founders, he warned that rival Stripe and famed accelerator Y Combinator (YC) — which counts Stripe among its biggest success stories — are “mob bosses” that will pull “every power move imaginable” to squash competitors.

One of power moves, wrote Breslow, is to keep any threat to Stripe out of YC, which he says rejected Bolt’s application earlier in time. He also accused Stripe of “co-running” the link aggregator and message board that’s owned by YC, Hacker News, and thus limiting how much attention Bolt received.

Not last, he accused Stripe of deliberately funding a direct competitor to Bolt at the same valuation that Bolt enjoyed at the time.

The last accusation seems fair, given that Stripe did lead a $102 million round in the upstart checkout company Fast a year ago. But defenders of both YC and Stripe were quick to dismantle Breslow’s other claims, including Stripe’s power over Hacker News, YC’s unwillingness to fund rivals to Stripe (it has funded other payments startups), and Stripe’s relationship to Lyft, which Breslow tweeted was a YC alum (it is not).

Some wondered if Breslow might be having a meltdown. Other assumed the whole thread was a marketing stunt.

Breslow also found plenty of support for that first thread, which has now garnered nearly 9,000 “likes” on Twitter, and may have encouraged him to tweet more about YC on Saturday. (He warned founders that YC takes far more from them that it delivers, a message that was also both criticized and celebrated.) In fact, asked Friday if he regrets going after the two powerful Silicon Valley institutions so publicly, he noted the many hundreds of supportive messages he received from other founders.

As far as he is concerned, adds Breslow — who grew up in Miami and still lives there — there is a lack of “authenticity” in the region. “I felt like I was being given lip service a lot and that’s just not how I roll. Especially with the tier one VCs, I just kept getting the run around [despite that] I’m building a great business.” Being in Miami “definitely empowered me to do this.”

Whether investors, like YC, that have passed on Bolt will regret it is the question.

By Breslow’s telling, the company, whose checkout technology is already used by a wide number of retailers, signed roughly 10 major deals in the second half of last year, and each is bigger than any that Bolt has signed in the company’s history previously.

These exclusive partnerships will “generate billions in revenue” when rolled out, he says, offering that the process takes time given the “large technical lift” of some of these “large merchants and commerce platforms.”

As for how Bolt makes money, it takes zero fees off transactions for first-time customers and 2% off every transaction completed by a customer it already knows, so as the “larger our network [of retail partners] grows, the higher percent of transactions we’re charging for,” says Breslow.

Currently, he says, just 5% of all transactions involve shoppers it has seen before across its network, meaning it is charging a fee on just one out of every 20 transactions. But “because we know we have hundreds of millions of shoppers coming on board the network,” he continues, “a majority of our transactions will be network powered . . . and our profit will grow exponentially with the network.”

So goes the expectation anyway. The proof, naturally, will come when those partnerships go live. In the meantime, Bolt has no shortage of competitors that, like Bolt, are selling retailers on the data they gather and their accompanying ability to offer a more personalized shopping experience, along with one-click returns and order tracking. Just one of its many rivals, Checkout.com, raised $1 billion at a $40 billion valuation two weeks ago. Payment giants like PayPal, Block, Shopify and (yes) Stripe, are also racing to garner more of the online checkout action.

Breslow, unsurprisingly, sounds undaunted. He says that already, Bolt’s new CEO, Kuruvilla, “has completely transformed the organization,” adding, “I get to take credit for a lot of stuff that he does [but] I’ve learned more from him on how to execute than anybody in my life.”

Breslow also underscores that while he’s officially handing off day-to-day management of Bolt, he’s not going anywhere. “Without going into specifics,” he says, “I have a lot of votes in the company.” (Like many tech founders, Breslow holds super-voting shares, meaning he owns a class of stock that provides its holders with outsize voting rights; a source close to the company says that because of those shares, “Ryan controls the board; he is the boss.”)

Indeed, Breslow suggests that installing Kuruvilla as CEO has been a strong likelihood since Breslow began recruiting him in 2019, and that Kuruvilla’s appointment right now has nothing to do with Breslow’s tweet storms but instead ties to Bolt’s fiscal year, which begins tomorrow, February 1.

In the meantime, says Breslow, he’s excited about his new role as executive chairman. “I have the self awareness to know when someone’s better than me at certain things, and Maju is better than me at a lot of things.” Now, he says, he can step away from those things and “exclusively focus on culture, vision, landing company-defining deals, and fundraising. Those,” says Breslow, “are my superpowers.”

To date, Bolt has raised funding from BlackRock, Schonfeld, Invus Opportunities, H.I.G. Growth, CE Innovation Capital, Tribe Capital, Untitled Investments, General Atlantic and Activant Capital, among many others.

That newest tranche is expected to close soon.