Mike Murchison, co-founder and CEO of Ada, has an enviable dilemma. Launched in 2016 by Murchison and his co-founder David Hariri, Ada is an AI-native company that aims to revolutionze how businesses approach customer service. The company has already attracted a buzz, having successfully raised its Series A in 2018 and securing dozens of enterprise customers. Thanks to the strength of Ada's product and Murchison's unconventional approach to fundraising, numerous investors have indicated their excitement for the startup's next round. Now, on a short but packed trip to San Francisco to kickoff their Series B in January 2020, Murchison must decide which investor to select, as potential contendors clamor like suitors with ostentatious displays of intent. In so doing, he and his team must wrangle with the tradeoffs of valuation, dilution, reputation, and more in considering what best suits the vision they have for Ada's future.