Journalism, as a practice and a profession, stands at a financial crossroads. For much of its history, the money ledger has resided on the “other side” of the journalism business. While journalists pursued truth, advertisers seeking an audience provided the cash flow. Traditional approaches are being supplemented with dynamic, leading-edge practices that demand that content creators and editors understand more about the financial health of their media entities. Oct. 12–13, 2017, the Donald W. Reynolds Journalism Institute and the Missouri School of Journalism hosted an intimate, powerful and resonant conversation on the importance of creating engaging content while maintaining a monetization strategy that works. The opportunities for making money with strong foundational content have never been greater. We looked at best practices for how journalists, editors and other media leaders are engaging audiences while increasing the bottom line.