Fresh out of a public social media debacle, Gary Vaynerchuk needs to reconsider the approach he takes in leading his digital media agency, VaynerMedia. Founded in 2009 by Gary and his brother AJ, VaynerMedia has grown into an unconventional creative marketing agency. With notable clients and a savvy and personable approach to maintaining attention arbitrage, the future looks bright with Gary at the helm of VaynerMedia. Or does it? This case explores Vaynerchuk's strengths and weaknesses, VaynerMedia's successes and challenges, and the overall command of the marketing firm as it continues to grow and evolve in an ever-changing digital media landscape. Ultimately, the case highlights a tension many ventures face as they mature from initial founding to growth sustainability: should the visionary CEO continue leading the charge forward, or should he consider stepping aside and allowing his firm to lead its own way forward?