In October 2008 a Gmail engineer named Jon Perlow shipped a fix for his own worst habit. He'd once told a girl he had a crush on her over text. Another night he emailed his ex-girlfriend to suggest they get back together. "Sometimes I send messages I shouldn't send," he wrote on Google's blog.
So he built Mail Goggles. Switch it on, and from 10 p.m. to 4 a.m. on Fridays and Saturdays, Gmail made you solve math problems before anything went out. Basically a breathalyzer made of homework.
Mail Goggles never read a word you wrote, which was the clever part. Love letter or grocery list, it had no idea. It only watched the clock and bet that 1 a.m. on a Saturday was when you'd do something dumb.
Five months later Gmail shipped Undo Send, which doesn't unsend anything either. It just holds your email for five seconds while you panic.
Both features sell the same thing: one extra beat between finishing a message and losing it for good.
Lawyers need that beat too, just not at 1 a.m. Their danger hour is 10:41 in the morning, stone sober, pasting a client's email into ChatGPT to clean up a reply. A math quiz won't save anyone there.
Clio's 2026 numbers on solo lawyers:
- 71% use AI for legal work
- 47% use consumer tools like ChatGPT
- 57% have no written AI policy
Then in February, Judge Rakoff in Manhattan ruled that a defendant's chats with Claude weren't privileged, partly because he'd accepted Anthropic's consumer privacy policy. (You read yours, right?)
Today's idea is Mail Goggles that reads the email. A browser extension holds the prompt locally before it reaches ChatGPT, Claude or Gemini, catches the client's name, the kids and the docket number, and swaps them for roles like [CLIENT_01] so the AI still knows who's who. Five-second review, then send. Start with family law, where every prompt is a whole household.
Pricing is $19 a month for solos and $59 for small firms of up to three lawyers. That's about $15,000 MRR at 500 solos and 100 firms, with no AI bill per prompt, because the detection runs on the lawyer's own computer.
Read the full playbook here:
71% of solo lawyers use AI, nearly half on consumer ChatGPT, and a federal judge ruled a consumer AI chat isn't privileged. The wedge is a $19 browser extension.
From the Vault:
Korea's wakppu ball, a $2 wax-shell sphere cracked once on camera, spiked 500% and turned a sensory toy into self-shooting content. TikTok Shop has the supply and no brand.
Seoul's Buddhism pop-ups log 3,000 sales a week and phone-free events are up 913% on Eventbrite. The U.S. version fits in a 10-by-10 booth, and the participant isn't the customer.
