Episode #113: Howie: The AI Secretary I talked to @awwstn at @howie_ai about why AI assistants are so hard to build, deciding to make Howie super narrow, and everything that went into build the product, brand, naming, and viral launch video. Thanks to @Hanover_HQ for supporting this episode! Stream here on X + link in the replies. Timestamps: 3:35 Howie: The AI Secretary 6:08 Why AI assistants are so hard to build 16:19 Why Howie started in email 20:49 Adding a human in the loop 30:48 AI software vs AI-powered humans 36:21 How a meme inspired Howie 39:29 Inside the making of Howie’s launch video 44:15 Howie’s viral launch video + Discussion 53:47 Designing the brand 1:01:37 Long-term opportunity and roadmap 1:07:53 Working for Jason Calacanis 1:12:00 Jason’s media lessons 1:16:51 How Howie got its first users 1:19:35 Pitch deck strategy that raised $6m 1:24:09 The mistake of optimizing for growth too soon 1:29:48 Building an AI company outside of SF 1:33:13 Being Superhuman’s 1st customer, Mercury’s 3rd