Aug 31, 2026 · 13 min · 6 segments
This episode explores how AI is making phishing scams more convincing—and why nonprofits need stronger staff training, verification procedures, and financial safeguards. Learn how scammers impersonate…
Hit home for us recently, and it began with a random email that I got from a past client and they're like, was this you guys sending me this? And essentially, in the subject, it was like, hey, quick security update, and it came from our president, or it seemed as though it came from our president, except, except, even though it had the signature of Megan Ann Holt, like, had her picture in there, had it, like, the email came from megan.wholewhale.gmail.com, which is not an email address, right? that Megan uses.
And clearly it's a Gmail account, but it was basically trying to fish our past client.
And I think George, we're entering into an era where AI makes running scams like this excruciatingly efficient, right? You can set agents upon the internet and have them scrape staff at companies to en masse and in bulk kind of fish pretending to be executives at B2B companies, marketing, inbound.
And you can make it sound like you are representing a US tech company or any company right and i think that was the blocker and the old scams it's pretty easy to tell right if these scams were written by someone english not their native language not to be biased but like that is where the majority of the scams originate right um george you can do that sounds like everyone else sounds like because we're all using the same ai model these and really kind of authentically spoof real people.
Americans lose billions and billions of dollars a year to email and phone scams, particularly senior citizens.
But George, importantly, Never, ever respond to an email with any type of security information or a request for a two-factor authentication code.
You always need to make sure if you're getting asked for a code and you didn't ask for a code, that's a scam.
If you're a nonprofit, conduct kind of training exercises, have meetings about this, explain to employees what not to disclose over email.
And George, for us, this is very kind of easy to tell because we don't use email, we use internal like, you know, Slack, quite frankly, internal communication systems.
Hit home for us recently, and it began with a random email that I got from a past client and they're like, was this you guys sending me this? And essentially, in the subject, it was like, hey, quick security update, and it came from our president, or it seemed as though it came from our president, except, except, even though it had the signature of Megan Ann Holt, like, had her picture in there, had it, like, the email came from megan.wholewhale.gmail.com, which is not an email address, right? that Megan uses.
And clearly it's a Gmail account, but it was basically trying to fish our past client.
And I think George, we're entering into an era where AI makes running scams like this excruciatingly efficient, right? You can set agents upon the internet and have them scrape staff at companies to en masse and in bulk kind of fish pretending to be executives at B2B companies, marketing, inbound.
And you can make it sound like you are representing a US tech company or any company right and i think that was the blocker and the old scams it's pretty easy to tell right if these scams were written by someone english not their native language not to be biased but like that is where the majority of the scams originate right um george you can do that sounds like everyone else sounds like because we're all using the same ai model these and really kind of authentically spoof real people.
Americans lose billions and billions of dollars a year to email and phone scams, particularly senior citizens.
But George, importantly, Never, ever respond to an email with any type of security information or a request for a two-factor authentication code.
You always need to make sure if you're getting asked for a code and you didn't ask for a code, that's a scam.
If you're a nonprofit, conduct kind of training exercises, have meetings about this, explain to employees what not to disclose over email.
And George, for us, this is very kind of easy to tell because we don't use email, we use internal like, you know, Slack, quite frankly, internal communication systems.
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