As the founder and CEO-turned-Chairman of Sailthru, Neil Capel has spent many of his days helping brands personalize every interaction they have with consumers. In fact, thinking about these meaningful interactions is something he and his family have been doing in real life for generations as greengrocers in England. Sailthru, however, was his way of offering them at exponential scale while solving the growing complications brands faced as digital evolution was distancing them from their customers.

Ironically, by starting a company to help solve these problems for others, he was presented with a new set of worries: learning the ins, outs and pure mistakes of raising money, the art of using improv in sales meetings, the importance of work-life integration, and ultimately how to truly evolve a company from startup to a fully-functioning corporation.

AND, just before this episode was set to launch, we learned that Neil was experiencing a new set of obstacles; as a follow up discussion, he shared with us his most recent undertaking in replacing himself within the company as he transitioned from CEO to Chairman, making his life all the better.

For more from him, check out @neiljcapel and Sailthru.