Most conversations about AI are about what it can do. Very few are about who pays when it gets things wrong.

This week on Reframing Perspectives, I sit down with Catharine Montgomery — Founder and CEO of Better Together Agency, creator of TogetherAI, and one of the most important voices in the country on AI bias and inclusive technology. Catharine walks us through the mammy moment — the day she asked ChatGPT to generate content about Black women and watched it return a full historical stereotype — and the structural insight that has guided her entire body of work since: AI doesn't go neutral. It reverts to how it was originally trained.

We talk about the Biases in Generative AI survey she has been leading since 2024, the only longitudinal consumer study of its kind. The framework she calls born-inclusive technology — building with diverse voices from day one rather than auditing for bias after the fact. The creation of TogetherAI, a private AI platform built for nonprofits and mission-driven organizations, trained only on a client's own materials, drafting in their voice, detecting bias before anything goes public.

And we talk about what Catharine herself has carried to build all of this: a childhood of being bullied by her own community in rural Alabama, microaggressions her parents never taught her to name, a colleague who created a racist work environment at a progressive Boston agency, and a March 2022 morning when she woke up in a hospital bed with no memory of how she got there and a partner who, three days later, drove her home and never came back.

This conversation is for every changemaker carrying something invisible while still showing up. Every founder building from scratch in a system that wasn't built for them. And every leader who is finally ready to ask the question Catharine wishes someone would ask out loud: what has this work actually cost — and has it been worth it?

What we explore:

• Growing up in rural Alabama: being bullied by your own community and the long shadow it casts on identity and belonging
• Why Catharine chose PR and communications — and what she eventually learned about the gap between making money and making impact
• Moving to Boston in 2019 expecting progressive — and discovering the gap between liberal language and lived experience
• March 2022: a seizure with no medical explanation, a partner who said goodbye three days later, and the loneliness of carrying something terrifying while performing like you weren't
• Anthropic's Alignment Faking and the Othello reference (I am not who I am): why AI reverts to how it was originally trained
• The mammy moment: when ChatGPT returned a stereotype — and what it taught Catharine about who needs to be in the room
• Born-inclusive technology: why diverse teams must build AI tools from day one, not audit them after the fact
• The annual Biases in Generative AI survey — what consumers actually experience, and why most AI companies aren't yet incentivized to care
• Inside TogetherAI: a private AI platform built for nonprofits, trained only on a client's voice and values, detecting bias before content goes public
• Why every PR agency that doesn't incorporate AI thoughtfully will disappear — and what ”thoughtfully” actually requires
• The cost of building: racism at a progressive agency, seizures with no diagnosis, and what Catharine has learned about asking for help as a leadership strength

A question to sit with this week: If someone asked you what your work has actually cost you — and whether it's been worth it — what would you say?

Connect with Catharine and Better Together Agency:

• Better Together Agency: bettertogetheragency.com
• TogetherAI: the private AI platform for mission-driven organizations
• The annual Biases in Generative AI survey

Listen, subscribe, rate, share: If this conversation moved you, the most meaningful thing you can do is share it with one person who needs to hear it. Subscribing and leaving a review helps more changemakers find this space — and that is how this work compounds.

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