#266 Len Pagon — Robots & Pencils

Today I had the pleasure of speaking with Len Pagon, CEO of Robots & Pencils. Len has spent his career building and investing in technology businesses. He founded Brulant in his early 20s, grew it through multiple waves of technological change, later merged it with Rosetta, and then spent the next chapter investing through his family office, Next Sparc. Nearly two decades after leaving the CEO seat, Len found himself back in it at Robots & Pencils to take full advantage of the opportunity AI presents. In our conversation, we explore that return to founder mode, why he needed to wait for something sufficiently compelling to get him to make that leap, rebuilding Robots & Pencils as an AI-first company, why speed and constraints can fundamentally change how people work, and how AI is reshaping consulting, knowledge work, and organizational learning. We also talk about leadership the second time around, earned wisdom, and the renewed sense of purpose Len has found in building alongside a team again. Please enjoy this insightful conversation with Len Pagon. 00:00 Introduction to Len Pagan and Robots and Pencils 00:15 Introduction and overview of business growth 04:01 Why Len returned to CEO role amid AI opportunities 04:02 The competitive landscape against GSIs 09:59 The significance of constraints in AI project success 10:01 Speed of transformation and team rebuilding 14:48 Leveraging past experience in new AI wave 20:04 Rapid prototyping and AI zero milestones 20:18 Partnerships with AWS and other tech giants 25:04 The role of domain expertise in AI-driven business 30:05 Building AI proficiency across organizations 30:06 The impact of rapid decision-making and leadership 34:59 Unlearning old mental models for new AI realities 40:01 The strategic importance of being AI first 40:19 The importance of continuous learning and adaptation 44:56 The potential risks and ethical considerations of AI 49:57 The future of AI in organizational transformation 50:23 Future outlook and preparing for market corrections 55:01 Final thoughts on innovation and leadership 59:54 Lessons learned from AI project execution 01:09:57 The cultural shift towards AI adoption 01:19:53 Len's vision for Robots and Pencils in AI era ----- LINKS: https://robotsandpencils.com/robots-and-pencils-new-ceo-leonard-pagon/ https://www.linkedin.com/in/lenpagon/ ----- SPONSOR: Cerity Partners Cerity Partners, a full-service investment and wealth management firm serving high-net-worth individuals, entrepreneurs, and business owners, is proud to sponsor Lay of The Land. The firm has local roots in Cleveland and across Ohio, and like this podcast, Cerity Partners advisors specialize in serving the interests of local entrepreneurs and business leaders. The firm’s national presence means it can offer the resources and specialized knowledge of the largest institutions with the independence and service of a neighbor. The Cerity Partners Cleveland team understands the complexity that comes with wealth, and they adhere to fiduciary standards. Discover the financial lay of your land. Learn more at https://ceritypartners.com/NPR or call 216-464-6266. Roundstone Insurance Roundstone Insurance is proud to sponsor Lay of The Land. Founder and CEO, Michael Schroeder, has committed full-year support for the podcast, recognizing its alignment with the company’s passion for entrepreneurship, innovation, and community leadership.Headquartered in Rocky River, Ohio, Roundstone was founded in 2005 with a vision to deliver better healthcare outcomes at a more affordable cost. Over the past two decades, Roundstone has grown rapidly, creating nearly 200 jobs in Northeast Ohio. The company works closely with employers and benefits advisors to navigate the complexities of commercial health insurance and build custom plans that prioritize employee well-being over shareholder returns. By focusing on aligned incentives and better health outcomes, Roundstone is helping businesses save thousands in Per Employee Per Year healthcare costs. Roundstone Insurance — Built for entrepreneurs. Backed by innovation. Committed to Cleveland. Learn more at https://roundstoneinsurance.com/ ----- Stay up to date by signing up for Lay of The Land's weekly newsletter — sign up here: https://layoftheland.ck.page/5f0c1e28fa Connect with Jeffrey Stern on LinkedIn — https://www.linkedin.com/in/jeffreypstern/ Follow Lay of The Land on X @podlayoftheland https://www.jeffreys.page/