Matt Tara is the CEO of an e-commerce fashion company that failed, but is still very much alive in his head. As a former venture capitalist in private equity, Matt thought he'd be swift to success as an entrepreneur. When the road turned rocky, Matt was forced to put his company to rest, and he was left with many multifaceted feelings -- among them: failure, grief, and the understanding of what it means when an entrepreneur says "this is hard." Most of all, he felt abandoned and at a loss for peers who could really listen to him. In this conversation, Jerry helps Matt conceptualize the latest speed bump in his life. They begin to unpack all of the gifts and lessons received from this experience and propose tactics for keeping Matt's inner critic at bay as he considers what's next.