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"Bank On It" podcast: Mike Massaro from Flywire during Boston Fintech Week

September 27, 2018

Every week, the host of the Bank On It podcast, John Siracusa, talks with amazing fintech leaders and entrepreneurs. Through these conversations, he uncovers the amazing stories behind them, their creations, and the most important topics in fintech.

In this episode, John talks with Mike Massaro, CEO of Flywire. This is one of a few interviews that were 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 $6M 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 become the giant it is today. Mike admitted that it was misallocation of funds that 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 that was discussed during this episode.

Tune in and listen.