What happens when your technology is solid, your traction is real, and the problem is not your company, but the system deciding whether to trust you? In this episode of The Capital Flex, I sit down with Annie Brown, Founder and CEO of Reliabl, an AI infrastructure company helping companies improve accuracy and reduce bias in machine learning by fixing what most people ignore: the data labeling layer. Annie is a bias researcher, former UC San Diego AI scholar, and repeat founder whose work has been featured in Forbes and Fast Company. Annie has built and scaled in public, from founding a creative platform for women and LGBTQIA+ creators to growing Reliabl to $600K ARR in 10 months. She shares what it felt like to raise for an LGBTQIA+ focused product, then raise again for an AI infrastructure product, only to get stuck in the middle, where highly technical funds question the founder and underrepresented funds struggle with technical diligence. Together, we unpack the uncomfortable realities of raising capital at the intersection of deep tech, identity, and pattern recognition. This conversation covers vice clauses, LP pressure, technical diligence gaps and why women founders are often forced to navigate both credibility and capital at the same time. Key Takeaways: Why bias in AI starts at the data labeling layer, not just in the language modelHow vice clauses and conservative LPs quietly restrict what gets fundedThe double bind for women building deep technical infrastructureHow to use “reflection questions” to disarm biased investor commentsWhy trusting your gut is data and not emotionWhy AI-based tools for VC sourcing and diligence risk reinforcing existing biasMy Reflection & Challenge: What struck me most in this conversation is how often women founders are asked to contort themselves or strip out the very value proposition of their business just to be considered fundable. Annie’s story is not about traction or capability, but about structural misalignment between belief, trust, and technical understanding. Too often, founders are told to edit themselves instead of being evaluated on the business, and scarcity makes bad opportunities look like lifelines. Your job is not to survive every room, it is to choose the ones that can fund you without rewriting you. This Week’s Challenge: Pay attention to the feeling in your body during meetings. If something feels off, don’t override it with scarcity thinking. Before your next investor conversation, write down: What support you actually need from capitalWhat behavior would be a dealbreaker pre-check and post-checkOne sentence you’ll use to calmly redirect biased commentaryCapital is not just money, it’s a long-term relationship. Links and Resources: http://reliabl.ai http:/linkedin.com/in/andreafrancesb If you enjoyed this conversation, follow The Capital Flex, leave a rating and share this episode with a founder who needs it. And if you’re looking for a more candid space to talk fundraising, power and building inside systems not designed for you, stay close. The conversation continues. Production and Administration work completed by Smart Podcast Solutions and Elevate Virtual Business Solutions.
