As technology has evolved, the distribution channels for audiences and consumption of content are at an all time high, the world of journalism is facing unprecedented pressure to “evolve or die.” This problem, however, is not new. It’s an ongoing struggle for balance that’s existed since news organizations appeared online over two decades ago. No one knows this more than Gabriel Snyder. As a writer in this pivotal time, he has been witness to the last decade plus of digital media evolution at major publishers like Gawker, Newsweek, the Observer, and the New Republic. Over rum old fashioneds provided by Fool’s Gold, he recalls that while each suffered from nuanced challenges, no publisher was spared and his insight to what he has seen and the lessons learned along the way are critical to understanding where the industry is headed.