In mid-January, Jimmy Finkelstein privately conceded to some friends and business associates that his last-ditch efforts to save The Messenger, his media startup built on a decidedly anachronistic business strategy, might not pan out. By that point, of course, the full scope of his mediaco’s rapid yet entirely predictable demise had been laid bare for all to see. The company that he brought to market in May 2023, propped up by $50 million in funding and an audacious business plan to make $100 million in annual revenue, never passed the smell test. Not only was it predicated on the sort of disintermediated, traffic-at-all costs strategy that nearly euthanized the entire industry, and run incredulously by the indestructible Richard “Mad Dog” Beckman, but it was… nowhere. Did you ever read a Messenger story? I didn’t.

In many ways, in this very public industry, the story of The Messenger was akin to a chronicle of a death foretold. Sure, there were rumors about the company’s exorbitant burn rate, but no one thought it would burn out so quickly. Instead, over eight painful and humiliating months, The Messenger spent around $43 million, generated a mere $3 million in annual revenue, and, by the end of 2023, had less than $1 million in cash on hand. Needless to say, this was well short of the necessary cash to sustain its $5-million-a-month burn rate. And the horrific governance and cash management made it a D.O.A. rescue or bridge investment opportunity, even to Finkelstein’s many well-heeled Palm Beach friends.