Ep 496 After the Deal: CK on Selling for $510M, Taking a Sabbatical, and Redefining Success

·56 min·5 clips

CK sold his company for $510 million but hesitated because he thought it could become a unicorn in three years.

This episode of Built to Sell Radio features host John Warrillow interviewing Chang "CK" Kim, who sold his company Tapas Media for $510 million. CK discusses his decision to take a year-long sabbatical after the sale instead of immediately launching another startup. Tapas Media was a publishing platform for serialized digital comics and novels, ranking second in its U.S. app store category with 40,000 content creators. The company had about $40 million in annual recurring revenue and was profitable when CK sold it to the Korean firm Kakao in 2021 after nine years of operation. He explains the sale process took three months and emerged from what began as a Series C funding round discussion with an existing investor. CK stayed with the combined entity for about two years post-acquisition before beginning his sabbatical in 2023. He shares that a key factor in selling was his assessment that the business's future winning factor would shift from technology to intellectual property and content creation. CK traveled extensively with his family during his sabbatical, taking 22 flights in 2023, including a two-and-a-half-month summer trip across Europe. A surprising challenge was the volume of meeting requests he received despite being on leave, which he managed by being intentional with his time and learning to say no. He intentionally sought to meet people outside his tech industry circle, finding conversations with parents from his children's school and workers during a home renovation particularly rewarding. CK reflects that turning off social media and avoiding comparison with peers still advancing in their careers was crucial for his mindset. He recommends that anyone contemplating a sabbatical research the experience thoroughly, just as they would any major business decision. One regret he mentions is not undertaking one "crazy" personal challenge, like hiking the Camino de Santiago solo or a similar transformative physical journey. He advises creating a tangible fixed-income stream from investments to enable spending without the psychological stress of "eating into" principal capital. The conversation is conversational and reflective, blending practical exit advice with personal introspection on life after a major liquidity event. Entrepreneurs nearing a business sale who are curious about the emotional and practical transition will find this episode highly relevant. Listeners primarily seeking tactical negotiation strategies or valuation frameworks for selling a business might find the post-exit lifestyle focus less immediately applicable.

As heard by us

The sale matters less than the life that follows it.

Chang Kim's story is mostly about what came after the sale: a sabbatical, a move from founder mode into full-time fatherhood, and the awkward business of adjusting to sudden wealth at home.

Read the full review in PlayNext →

Why you'd press play

A $510 million exit, then the harder question: what do you do next?

Read the full recommendation in PlayNext →

Listen to the show on

Apple Podcasts Spotify

Play clips from this episode More from Built to Sell Radio