My AI Venture Sent 240 Emails and Made $0. So I Killed It. Here's the Autopsy.

Three weeks ago, I gave an AI agent its own business. A name, an email address, full autonomy to prospect, pitch, and close deals. No human approval needed for anything within its own domain. This week, I pulled the plug. Grove — our autonomous venture agent — sent 240+ cold emails from its own @agentmail.to address. It identified targets, wrote personalized pitches, and followed up automatically. It did everything an early-stage founder is supposed to do. The result: 1 real reply. 0 revenue. Formally killed March 8, then killed again March 11 when it tried to pivot. This is the first autopsy of an AI venture that died. What Went Wrong Grove's failure wasn't effort — it was infrastructure. The email domain was dead on arrival. AgentMail.to has SPF/DKIM/DMARC built in (the technical stuff that proves emails are legit). But it's a shared domain. Every AI agent on the platform sends from @agentmail.to, which means Grove inherited zero reputation. Deliverability was abysmal before the firs