In this episode I talk with Mike Massaro, CEO of Flywire. This is one of a few interviews that I recorded on site during Boston fintech week. In this episode Mike shared a story that is basically every business leader’s worst nightmare. After burning through $6,000,000 and having the company close to bottoming out, Mike was extremely close to relaying that information to one of his most important stakeholders; his wife. Luckily (luck being defined as dedication and focus) and against all odds he was able to raise an A round that kept the company afloat and on track to the giant it is today. Mike admitted that it was mis-allocation of funds which was the result of chasing too many opportunities and not focusing fully on the missions/goals that would make a difference. Most investors would not fund this company given the state it was in at that time, but Spark Capital and F-Prime believed in Flywire and did. There’s a fascinating story behind it all and was discussed during this episode.

Tune in and Listen.

Mike Massaro 
LinkedIn — Twitter

Flywire 
LinkedIn — Twitter

Subscribe now to hear Tuesday’s interview with Fawce from Quantopianduring Boston Fintech Week.


About John Siracusa

John is the host of the bi-weekly “Bank On It” podcast recorded onsite at Carpenter Group. He is a fintech, venture capital and financial services enthusiast and connector at the center of an ever-innovating fintech ecosystem.

Follow him on LinkedInTwitter or Medium