Skio, the Y Combinator alumni subscription payments company co-founded by self-proclaimed college dropout Kennan Frost, has been acquired by its competitor Recharge for $105 million. Frost, who had previously stepped back from his role as CEO, revealed that Skio only raised $8 million in funding but walked away with a hefty $105 million cash injection.

While the official press release did not detail the terms of the deal, Frost posted on X and LinkedIn about this unexpected windfall, stating that Skio had achieved $32 million in annual recurring revenue (ARR) and processed over $4 billion in payments. Frost’s journey from a solo founder to a multi-millionaire in just three years is nothing short of extraordinary.

According to Aidan Thibodeaux, the current CEO of Skio and its first COO, when he took over, the company focused solely on building the product rather than spending money on marketing or a sales team. Frost himself made every single sales call. This strategy paid off handsomely, highlighting that sometimes less is more in startup success.

Reflecting on his time at Y Combinator, Frost admitted that he 'completely failed during the batch' until he pivoted to subscription payments. His advisor Gustaf Alströmer confirmed the terms of the sale and praised Frost’s perseverance despite initial struggles within the accelerator program.

Frost is now back in the startup game with a new venture, Icon, offering AdMaker for ad generation and tracking. As TechCrunch Disrupt 2026 rolls around, one can only wonder if this event will provide more tales of unlikely tech success stories like Skio’s.