Kennan Frost, the founder of Skio, a 2020 Y Combinator alum, recently hit a pretty cool milestone. The startup he sold? His cash-out sale of his startup was a record-setting $105 million in cash! Skio may have only raised $8 million from investors so far, but it has proven that less can be more in the subscription management space. By the time of its sale, the company had processed more than $4 billion in payments and reached an ARR of $32 million.
Frost, a self-proclaimed college dropout, launched Skio to help make subscription payments easier for the brands he promotes. Through this work, he’s addressing an immensely important and growing problem in the e-commerce industry. In fact, he was dealt an incredibly tough hand to start out. A debilitating panic attack made him walk away from his engineering career at Pinterest. This seismic shift was the beginning of his path as an entrepreneur, and eventually led to him founding Skio.
After founding Skio, Frost continued to experience the ups and downs of entrepreneurship as a solo founder. He worked closely with his Y Combinator advisor, Gustaf Alströmer, who observed the challenges that come with being a solo founder. Even when the business went through multiple painful pivots over the course of the Y Combinator program, Alströmer said that Frost’s doggedness stood out.
“Being a founder is hard. Being a solo founder is much harder. Kennan did YC in S20 with Skio. Applied with one idea, pivoted during the batch, then pivoted again. Never gave up. The last pivot worked. Today Skio sold for $105M in cash. There are very few straight lines to success.” – Gustaf Alströmer
Bill Frost was true to his vision. With co-founder Andrew Chen, he did every sales call himself in those early days of Skio. The grit of the entire team, from production through post and even business affairs, got the creative team started on that momentum. Frost departed Skio around two years ago. His subsequent launch of a new company called Icon is further proof of his entrepreneurial spirit and dedication.
Recharge’s acquisition is a huge achievement for Frost. It’s a huge victory for Aidan Thibodeaux, who founded Skio and is now CEO of the company. Skio’s transition shows the intrinsic value it has established in its highly specialized, niche market. This remarkable change lays the groundwork for thrilling progress to come under new leadership.
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