Sometimes social media works and sometimes it doesn’t. For Matt Epstein, Chief Marketing Officer at Rippling, it is a little bit of both. In 2011, Matt went viral after uploading a Youtube video detailing why Google should hire him. It was also accompanied by a propeller plane with his URL attached, flying over the Google campus. Apparently, Google was not impressed, however, this bold decision ultimately worked in his favor. The video attracted many companies, which eventually led to the beginning of a fast-paced and fulfilling marketing career.In this episode, Matt discusses his unconventional way of attracting Google’s attention and what it was like to pass on other companies in lieu. He talks about how his brashness, which as he puts it, is just a “chip on his shoulder”, attracted the attention of Rippling founder, Parker Conrad. Now, he is along for the ride as he surrounds himself with other like-minded “crazy ones.” Matt also shares his take on why generalists and marketing ops should be “first hires” in SMB and SaaS, and how when you’ve got something to prove in that space it only increases your ambition. In this episode, we cover: How Matt’s plea to work for Google went viral - and why he hates social media. (01:48)Matt’s professional evolution from SigFig to employee #1 at Zenefits and his role in garnering the first customers. (08:04)Why Matt recommends generalists and marketing ops as the first hires in the SMB SaaS space - and a deep dive into how a “chip on your shoulder” and insecurity are powerful motivators for success. (17:00)Matt’s decision-making process from applying to Google to passing up on job offers from major tech companies - and Matt reflects on lessons learned at Zenefits. (24:16)How Rippling founder, Parker Conrad, convinced Matt to join the company - and Matt explores the next phase of Rippling’s app ecosystem. (34:26)Matt’s thoughts on Rippling’s recent product launch, marketing their catalog of products, and the challenges of scaling up at a startup. (44:32)A discussion about coping with pressure, why Matt looks for “the crazy ones” when hiring, and why he has no interest in being a founder. (53:26)Links:Connect with MattLinkedInEmail: mepstein@rippling.comRipplingConnect with JoubinTwitterLinkedInEmail: gtmg@kleinerperkins.com Learn more about Kleiner Perkins