47: From Math Teacher to AI Founder (with Joe Sessions)

For more on building AI products and careers, along with early course announcement and special pricing, subscribe to the AI Career Boost mailing list at https://aicareerboost.com/interested THE GUESTJoe Sessions is the COO and co-founder of Optimize, where he helps companies automate routine tasks and build the foundation for scalable AI adoption. With a career spanning hands-on software development, product leadership, and operational strategy, Joe brings a rare blend of technical depth and big-picture vision. He’s known for his ability to dive into the details when needed, while also guiding teams to step back and think strategically about long-term impact. A lifelong innovator and educator, Joe is passionate about empowering people and leveraging cutting-edge tools to drive meaningful growth—for businesses and individuals alike. Today, he joins us to share his insights on how thoughtful automation and AI can transform the way organizations work, scale, and lead in the digital age.THE SUMMARYRPA Before AI: Joe Sessions, COO and co-founder of Optimize, argues that most mid-sized companies shouldn’t start with AI at all — they should start with automation. Robotic Process Automation (RPA), he says, is the real foundation that enables scalable AI adoption later on.Simple Beats Flashy: Joe believes too many businesses jump straight into AI experiments without solid systems in place. His advice: simplify your workflows first. No databases, no endless code updates — just connect the dots between tools and eliminate repetitive tasks.Real-World AI Use Case: Joe shares his capstone project — an AI-powered document extraction system that detects features like fences in construction PDFs. He breaks down how he used workflows and Gemini to handle complex image data, showing how AI can add value only after automation does the heavy lifting.AI with Ethics and Practicality: A former Microsoft Responsible AI developer, Joe brings a measured view to the hype. He’s writing a book on ethical AI, aiming to ground the conversation in realism and responsibility — not fear or hype.Advice for Newcomers: Start small. Joe recommends OpenAI’s $20 plan and experimenting with custom GPTs for repetitive tasks. The ROI? He cut a five-week project down to three days using smart automation.Takeaway: Stop “AI-washing” your business. Nail your processes, automate smartly, and let AI follow naturally.THE SHOWWeekly conversations with the AI’s top product leaders. Join Polly Allen as she discovers the paths to success in the world of AI.THE LINKSHave a question you want us to answer? Send it through to [email protected] SessionsLinkedIn: https://www.linkedin.com/in/joe-sessionsMy linksLinkedIn: ⁠https://www.linkedin.com/in/pollymallen/⁠ AI Career Boost: ⁠https://www.aicareerboost.com/⁠

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