Creating an AI Clone with Diann Wingert

AI clones and GPTs are increasingly common, which brings forth so many questions! But the “aggressively human” question we’re exploring today is how much care, curation, and legal scrutiny goes in before you release it to real people.In this episode, we talk with return guest Diann Wingert, ADHD business coach and host of the ADHDish podcast, about Di AI — her newly launched digital coaching clone. Diann is a former psychotherapist turned business coach who works exclusively 1:1, and she just released a Coachvox-built AI version of herself in beta to current and previous clients.We get into the technical, client experience, and ethical questions of cloning a coach. We cover what Diann chose to include (and exclude) in the training data, the months of fine-tuning behind the scenes, the legal work she did before launch, and why she’s not trying to turn this into a passive income stream.* Why Diann has been wanting to “clone herself” since Dolly the sheep — and what finally made it possible* Choosing Coachvox over other clone platforms (and why support and training mattered more than the tech)* Why guest episodes and client success stories were excluded from the training data* The painstaking fine-tuning process: ~100 questions per framework, batched over months* Removing language she’d never use — like “ADHD is a superpower” and “work with your brain, not against it”* The legal work behind the launch: hiring an AI-savvy attorney to rewrite her privacy policy and terms of use* How she’s drawing the line between coaching and therapy inside the bot* Why she’s giving Di AI away in beta — and what data she’s actually trying to gather* The OCEAN personality score and how it’s reshaping how Diann talks about her ideal client* Risk tolerance, exit strategy, and what it looks like to run an experiment in public“I don’t want somebody going to the internet or to Gemini or Perplexity or Claude or ChatGPT when they’re running a business and they have an ADHD brain. I would much rather they go to something that is just my information. Not because I know everything about running a business with ADHD — ‘cause nobody knows everything — but because the information has already been filtered through 30 years of experience, multiple frameworks and models. And they can’t get an opinion at this point from Di AI that is not entirely consistent with that.” — Diann WingertAbout our GuestDi AICoachvoxWebsitePodcastLinkedInOCEAN personality testConnect with UsListen on SpotifyListen on Apple PodcastsMeg CaseboltJessica Lackey This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit aggressivelyhuman.substack.com