To Bolt-ly go: a business derailed by an empty copilot seat
Bolt, the San Francisco fintech startup (not to be confused with the Estonian mobility company going by the same name), peaked at an $11 billion valuation in early 2022. But things did not go as planned: multiple rounds of layoffs were necessary to keep the pace, a total of three CEOs took the seat consecutively, the original founder-CEO, Ryan Breslow, was sued by his own investor over a $30 million personal loan taken from the company, and finally, just two years later, secondary markets predicted the company was still worth only $300 million, a 97% decline. In need of a "wartime CEO”, the board, in a cinematic turn of events, appointed Breslow back into the CEO seat from where he fired the entire HR department, proclaiming to the world that the motivation problems he saw disappeared when the people did.
I. Three times absent
My question in all this: where was the copilot?
She was not there when Breslow borrowed $30 million from his own company. Any business with a functioning finance and legal function requires board-level approval on related-party transactions, with documented terms, repayment schedule, and collateral: basic governance. At Bolt, regardless of whether the approval was given, the transaction was kept away from investors, and company funds had to bail Breslow out when he defaulted. It was only then the investors got informed that it had happened in the first place, making it a reporting failure on top of a potential governance oversight.
They were not there when the internal culture started drifting. Breslow first stepped away as CEO in early 2022. He came back three years later to a company he described as entitled, unproductive, and bloated. Regardless of whether that characterization is fair, cultural drift in a company that has lost 97% of its value shows up in the data long before the CEO fires the HR department: clustering of PTO utilization, sick leave, and discretionary spend, upwards drift of performance ratings, and dropping equity exercise rates. Nobody thought it necessary to investigate this and challenge the company’s decision to just cut more headcount.
He was also not there when valuation started plummeting in the secondary market. Bolt's management insisted its real valuation, estimated by them to be $14 billion, was supported by “The London Fund” who had pledged $250 million worth of “influencer marketing credits” at that valuation, even though none of their claimed existing portfolio companies had ever heard of them. Nobody forced the board to understand what had happened when that deal, unsurprisingly, fell through.
II. Why this mattered
None of these three failures are truly exotic: related-party oversight, workforce analytics in the board pack, and valuation benchmarking are all needed to enforce uncomfortable conversations to happen on schedule rather than in crisis. It is for that reason a seasoned copilot, reporting to the board, is needed, and its because that seat was empty that those failures happened at Bolt at the same time. Yes, they had people handling finances and HR, but in many startups board and investor communication lands on the founders. And because they are protecting different things than due process, like their status or autonomy, that stops working exactly when the stakes are highest.
A CEO transition is such a crucial moment where a more neutral pair of eyes matters most: the outgoing CEO's mental model of the company leaves with them, and the new one starts from scratch with whatever is available. Sitting across finance, legal, HR, and board reporting simultaneously, it is often the CFO or COO that holds the institutional memory through these transitions, and has the mandate to surface what the room would rather not discuss. If such a person is absent, the new CEO is operating from a partial model that feels complete but is not, because nobody, including those already at the table, is correcting it.
Bolt had three consecutive CEO transitions with no such continuity. The founder’s view on the product, the team, and the financials had to be reinvented every time. If the investor is not in the know on those, their model is only based on their own expertise, like valuation metrics and the milestones. Neither model includes what the other knows or what they are protecting, and because each model feels sufficient, those gaps stay invisible.
Moreover, the instruments that formalize relationships, like the shareholder agreement, the board reporting cadence, and the employment contracts, are a snapshot from the time of signing. They capture what both parties knew and were willing to write down back then. In Bolt’s case, governance was aligned to a strong founder-CEO, not internally promoted or hired ones. The instrument does not update itself as the models underneath keep moving without someone pointing out the world has changed, until a forcing event makes it visible all at once.
Unsurprisingly, in Bolt’s case there were two such forcing events working in tandem around the original founder: Breslow defaulted on his loan, and returned as CEO. The loan default lawsuit was settled through a repurchase of the suing investor’s shares, which also opened the way for Breslow to return, by removing the only vote that prevented a unanimous approval. What he discovered (the cultural drift, the productivity gap, and the organizational bloat) had been accumulating for three years. His response (firing HR, cutting 30% of staff, declaring wartime) was proportional not to the problems themselves, but to the shock of discovering them all at once with nobody having flagged them earlier.
III. Learnings
The lack of incentive to create a strong financial and legal structure could be felt across every single of Bolt’s failures AND their solutions. What happens next can go in two directions: either the company gets back into shape under Breslow's reign, or the board and its shareholders will have to accept that the secondary market’s valuation is closer to reality than they would want.
Every company's structure describes a version of itself that no longer exists. The only question is whether someone is incentivized to close that gap on an ongoing basis, or whether a forcing event does it all at once. Bolt got the latter and paid the price: most companies will too, unless they get the structure in place that incentivizes having the tough conversations early.
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