#29: Catching Up On Twilio's Big Moves With Captain Twilio and Justen Stepka

Twilio has had an exciting fall. First, Microsoft announced Azure Communication Services, viewed as a shot across the bow at Twilio in the developer driven communications space. Then, Twilio had its first investor day in three years, refreshing investors on their trajectory. Lastly, Twilio announced the purchase of Segment, a customer data platform that signals Twilio’s climbing of the value chain. To break it all down, we bring on Captain Twilio, an experienced investor whose portfolio features one stock, Twilio, and Justen Stepka, our frequent guest and an Atlassian and, more relevant to today’s conversation, Docker alum who has firsthand experience with Segment as a user. This is a fun conversation for anyone following Twilio, and it also adds interesting perspective on business strategy and SaaS valuations. Topics Covered 3:15 minute mark - The Segment value proposition 9:15 - Recapping Twilio Signal and what it says for Twilio’s strategy 13:15 - So why did Segment sell? 19:15 - How Segment fits in 24:15 - Single customer risk as well as enterprise opportunities 28:45 - The analytical edge that comes from a data tool like Segment  31:45 - Build vs. buy and microservices architecture vs. monolithic when thinking about data 36:45 - Entering another giant’s territory…the pending showdown with Salesforce 48:15 - The right valuation approach and what metrics (and dollars) matter most References: Segment blog on gross margins: https://segment.com/blog/the-10m-engineering-problem/ Jeff Lawson interview with Ben Thompson: https://stratechery.com/2020/twilio-acquires-segment-what-is-segment-an-interview-with-twilio-ceo-jeff-lawson/