Jay Gould co-founded Yashi, a platform that helped advertisers buy ads on video content. Yashi grew to more than $25 million in revenue and more than $5 million in EBITDA when Gould received an offer of $33 million from Nexstar Broadcasting. The offer represented around 6 x EBITDA and Gould was conflicted. He knew he could probably get more, but he had also seen how quickly a successful company can go to zero.