From CIA to AI: Brian Raymond’s Journey Building Unstructured.io into a GenAI Powerhouse

What does it take to go from CIA officer to founder of one of the world’s fastest-growing AI startups?In this episode of The Mark Haney Show, I sit down with Brian Raymond, Founder & CEO of Unstructured.io, to unpack his remarkable story and the explosive growth of his company.• Brian’s journey from UC Davis → CIA → Investment Banking → Startup Founder.• Why 90% of enterprise data is useless for AI—and how Unstructured.io fixes it.• The Fortune 1000 race to adopt GenAI, with billions being invested.• How AI agents are changing the game (and why they don’t sleep).• Lessons from raising $65M+ in funding in just three years.• Where Brian sees the biggest opportunities for entrepreneurs in this new AI era.This isn’t just a story about AI—it’s about risk, resilience, and building at the bleeding edge of technology.Website: https://unstructured.io/Youtube:  @unstructuredio  LinkedIn: https://www.linkedin.com/company/unstructuredioX: https://x.com/UnstructuredIOGithub: https://github.com/Unstructured-IO👉 Watch now to learn how Brian Raymond is helping shape the future of AI and what it means for entrepreneurs everywhere.00:00 – Cold Open: “Agents don’t sleep”00:32 – Intro & Guest Setup02:47 – What Unstructured Does + LLMs’ 3 Problems05:06 – RAG & the Modern AI Stack07:17 – Data Security Realities09:10 – Video/Podcast & Surveillance Use Cases13:18 – “Intern” Analogy: Retrieval vs. Fine-Tuning16:46 – Infrastructure Role & Enterprise Examples20:01 – Talent Arms Race & Startup Paths24:23 – AI Ripple Effects: Energy, Data Centers, Trades29:11 – Brian’s Path: CIA → MBA → Startups38:59 – Funding & Breakout Growth44:57 – GTM, Deployment, Partnerships50:08 – AI Agents at Scale & New Challenges53:18 – Who Buys (AI Maturity), Vision & Exits1:03:01 – Tools to Try & Closing______________________________________________________________If this episode inspires you to be part of the movement, and you believe, like me, that entrepreneurs are the answer to our future, message me so we can join forces to support building truly great companies in our region. -Subscribe to my channel here: https://www.youtube.com/channel/UCom_​... -  Mark Haney is a serial entrepreneur that has experience growing companies worth hundreds of millions of dollars. He is currently the CEO and founder of HaneyBiz -  Instagram: http://instagram.com/themarkhaney​ Facebook: www.facebook.com/themarkhaney LinkedIn: https://www.linkedin.com/in/markehaney​ Website: http://haneybiz.com​ Audio Boom: https://audioboom.com/channels/5005273​  Twitter: http://twitter.com/themarkhaney-This video includes personal knowledge, experiences, and opinions about Angel Investing by seasoned angel investors.  This content is for informational purposes only and should not be construed as legal, tax, investment, or financial advice.  Nothing in this video constitutes a solicitation, recommendation, or endorsement.#thebackyardadvantage #themarkhaneyshow #entrepreneur #PowerOfWith #SacramentoEntrepreneur #Sacramento#SacramentoSmallBusiness #SmallBusiness #GrowthFactory #Investor#Podcast