Episode 381: Mike Massaro - CEO, Flywire

Episode 381 of The VentureFizz Podcast features Mike Massaro, CEO of Flywire, a global payments enablement and software company. This is the full lifecycle story of an idea to a pillar publicly traded tech company in the Boston tech scene and it has it all. An international founder who discovered a major problem while trying to pay his tuition at MIT, to Mike joining the company after its Series A, an evolving business model from consumer to B2B, navigating choppy near death experiences to scaling aggressively, then raising multiple rounds of venture funding to an IPO, and more! It really is an inspirational story for all entrepreneurs to hear, as it is never an easy up & to the right story. There is so much that goes into building a successful company and this one does not disappoint. Chapters 00:00 Intro 02:17 Learning to Lead & the Importance of Communication 04:51 Mike's Background & Getting Started in Tech at edocs 15:00 Carrier IQ 19:47 The early days of Flywire 19:52 Navigating the Go-to-Market Strategy 29:52 Moving into the Role as CEO of Flywire 31:55 Challenging Times 35:09 Scaling the Company & Playing Long Ball 39:17 Expanding into New Industries 41:47 The Impact of COVID-19 45:20 Flywire IPO 50:06 Looking Ahead: Growth and Innovation 51:42 Building a Strong Company Culture 57:12 The Importance of a Strong Board of Directors 59:50 Hiring for Leadership Roles 01:02:13 Apps, Books, & Fun Episode Sponsor: As a longtime champion of the local startup ecosystem, Silicon Valley Bank supports innovative companies with the solutions and financing they need through every stage of growth. With more than 1,500 bankers and relationship advisors, and $42B in loans as of Q2 2024 – SVB delivers the right people, service and resources to support your entire financial journey. Learn more at SVB.com.