In 2011, Rafat Ali launched Skift, a B2B publisher that covers the travel industry. At first, Skift was mainly monetized with advertising, but Rafat quickly realized that scaling a B2B niche outlet required a diverse set of business models that included memberships, research, events, and advertising. He also acquired multiple other media outlets that operated in adjacent industries. In an interview, Rafat walked us through this journey and explained how he managed to simplify the company’s value proposition while embracing the complexity of multiple revenue models. We also spoke to Walter Frick, who ran the membership program for business publisher Quartz for nearly three years. He answered our questions about what motivates readers to convert into subscribers and what he learned when Quartz made the radical decision to completely remove its website paywall.