Learn from the Devil

Al Pacino got it right in The Devil’s Advocate: for all our advances in greed, lust, and gluttony, vanity is still the Devil’s favorite sin. If your users want to tell you how they’re exploiting your systems: let them.

A few weeks back, the NYT wrote an article about Matthew Gallagher and how his two-person, AI-powered company selling pharmaceuticals online was on track to do $1.8b in sales this year. I can’t tell if the reporter, Erin Griffith, just didn’t do much fact-checking or was gleefully content to let Gallagher dig his own grave but the article is a trainwreck.

Gallagher meets her at Soho House and namedrops VC advisors, but says he has “told hardly anyone about his company.” For good reason, it turns out. Griffith briefly mentions some “AI slop” and faked before-and-after weight loss photos. But as the internet quickly took over the investigative part of her job, it was revealed that Gallagher’s company has an F with the BBB, is being sued, and the FDA is already circling.

Gallagher is an experienced serial founder who has worked in VC. And this is not his first time doing shady shit; the Reddit stories about his previous company, Watch Gang, are a horror show and he is, fairly objectively, not a good guy.

So why paint a target on his own back by doing the article?

Because this is the era of Trump, of Tate, of Musk. It seems ahistorical to argue that they are more greedy, lusty, or gluttonous than previous generations; we have plenty of evidence that wealth has always been exploitative. But vanity, coupled with the powerful channel that is the internet, has become an irresistible lure.

This may be temporary; someday, an SEC with teeth will come for Musk, just as an FDA with teeth will come for Gallagher, and those public examples will force folks like them back into the shadows. But for now, vanity is a powerful tool for finding the fault in your own systems.

Start with a Reddit search for your company. Are folks sharing interview answers? Exploiting coupon codes? Loading up with pricing mistakes? Chances are, if you’re big enough, you’ll find at least something that you can use to improve your service.

While you’re there, consider leaving a honeypot, a la Pacino. “Anyone found a way to cheat on the Oceans Talent aptitude assessment?” will bring the vain out of the woodwork, because for many, the only thing more fun than cheating is bragging about it.

And sometimes, a “hack” is just an invitation to build a new feature. I’m always reminded of Mike Flowers’ team in the NYC government, who were amazing at finding clever ways to close gaps. For restaurants that were dumping their grease down the drain, Flowers’ team introduced them to biofuel companies that would happily recycle their oil for free. For ambulances that were parked instead of circling, they introduced new parking spots that were better distributed. Just because Gallagher needs to go to jail doesn’t mean the only response to subversion is punishment.