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:

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