Subscription billing firm Skio exits for $105 million cash in acquisition by rival Recharge

Subscription billing fintech Skio has been acquired by its direct competitor Recharge in a deal valued at $105 million in cash. The transaction was officially announced on Thursday, 30 April 2026, marking a significant exit for the company founded by Kennan Frost. Frost, a 2020 Y Combinator alum, confirmed the terms of the sale via social media posts, noting that the company had raised only $8 million from investors prior to the transaction.

The acquisition highlights a substantial return on capital for Frost, who established Skio after leaving his engineering role at Pinterest. At the time of the sale, the company reported $32 million in annual recurring revenue (ARR) and had processed a total of $4 billion in payments. Frost described the outcome as a healthy exit, particularly given the modest amount of external funding secured before the deal was finalised.

Leadership changes within Skio played a role in the company's trajectory leading up to the sale. Current CEO Aidan Thibodeaux confirmed that Frost had not been running the company for approximately two years. Thibodeaux, who began as the startup's first COO, took over operations and steered the firm with a strategy focused exclusively on product development rather than spending on marketing, advertising, or a dedicated sales team. He and founding CTO Andrew Chen reportedly made every sales call personally during this period.

Frost's journey to the acquisition was marked by significant personal and professional challenges. He founded the company following a panic attack that led him to resign from his position at Pinterest, a move compounded by the onset of the pandemic shortly thereafter. Frost noted that he initially failed during his Y Combinator batch before pivoting to the subscription billing concept. It took three years to reach $10 million in ARR and achieve profitability before the current team scaled the business further.

Following the announcement, Frost indicated he is moving on to a new venture called Icon. This new startup offers a product named AdMaker, which focuses on ad generation and tracking campaigns. The sale was widely noted in the tech community, with Frost's announcements reposted by Y Combinator and Nicolas Wittenborn, founder of the venture capital firm Adjacent.

Gustaf Alströmer, Frost's YC advisor, confirmed the sale terms on X, emphasising the resilience required during the accelerator program. Alströmer highlighted that Frost struggled during his time at the accelerator but never gave up, ultimately executing a final pivot that led to the successful sale. Frost, Recharge, and Wittenborn could not be immediately reached for further comment regarding the specifics of the deal.