Ask why it won’t work — Rick Song’s lessons from Square and building from 0 to 1

Today’s episode is with Rick Song, the co-founder and CEO of Persona, a platform that enables companies to create the ideal identity verification experience for their customers. Before founding Persona in 2018, Rick was an engineer at Square for 5 years, and an early team member at Square Capital.  Rick is at an exciting inflection point in his journey of building from zero to one — just last week, Persona shared that they’ve raised a $50 million Series B round. The company plans to double the team this year to keep up with revenue that’s surged more than 10x and a customer base that’s grown to include big logos like Square, Postmates, and Gusto. In today’s conversation, one theme stands out: Rick is somewhat obsessed with the idea of pre-mortems, or figuring out why things might not work out. From all the ways a candidate might fail, to why a customer won’t want a product, to how a commonly-used framework might not be a good fit, Rick brings this mindset to every aspect of running Persona.  From hiring lessons to go-to-market strategies, Rick offers up some counterintuitive thinking, including why his engineers sell and cold-email prospects, and why he doesn’t try to convince candidates that Persona is a company that will change the world. Today’s episode holds tons of insights for anyone who’s a founder or thinking about starting a company one day, but there’s also plenty in here for engineering leaders and hiring managers. You can follow Rick on Twitter at @rickcsong and learn more about Persona at https://withpersona.com/  You can email us questions directly at [email protected] or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson