How To Move Money

Will Messina - CEO, Grailpay

January 29, 2026

I hadn't written a check (or cheque if you’re British/ Canadian) since I was 12… and then I moved to America.

Two years in, I use a modern fintech bank but I still can't send money to anyone without using a third-party app. Why do I need Venmo to split a dinner bill?

The payments system here in the US is NUTS! So I asked Will Messina, CEO of GrailPay, to help me understand it better.

We cover: 

  • Why businesses still mail checks like it's 1987
  • How Venmo actually makes money (it's not from moving money)
  • Why banks charge $20 for a wire transfer
  • What stablecoins will actually be used for.

One thing that blew my mind: Delta makes $2 billion a quarter from payments alone - they're basically a payments company that happens to fly planes.

So if you’re as baffled as I was by how banking works in the US, this one’s for you. Listen now on Spotify and Apple Podcasts!

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