Lay of The Land

Hosted by Jeffrey Stern

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273

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Oct 2026

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About the show

Telling the stories of entrepreneurship and builders in Cleveland and throughout Northeast Ohio. Every Thursday, Jeffrey Stern helps map the Cleveland/NEO business ecosystem by talking to founders, investors, and community builders to learn what makes Cleveland/NEO special.

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October 22, 20261 hr 24 min

#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/

October 15, 20261 hr 6 min

#265 Daniel Asbury & Ben Goehner — Western Dominion

Daniel Asbury and Ben Goehner are co-founders of Western Dominion Land Company, a vertically integrated housing platform combining land acquisition, large-scale community development, and structural panel manufacturing all under one roof. In our conversation, we explore why the collapse of smaller and midsize homebuilders after 2008 left entire communities without meaningful new housing supply, and why Daniel and Ben believe the next generation of housing companies will need to manufacture, develop, finance, and deliver homes as an integrated system. We talk about the economics of attainable homeownership, land banks and public-private partnerships, the role of structural panel manufacturing, rebuilding the middle market of American homebuilding, and Western Dominion's ambition to take what they've proven in Mansfield and scale it across Ohio and, ultimately, the country to help rebuild the American Dream of homeownership Daniel and Ben are refreshingly candid about the state of the housing market, the structural problems they believe are holding it back, and what it will actually take to build at scale, making this one of the more educational and insightful conversations I've had on housing. Please enjoy my conversation with Daniel Asbury and Ben Goehner. 00:00 Introduction to Western Dominion and its mission 00:14 Introduction to the housing challenge in rural America 00:50 Founders' backgrounds and how they met 02:51 Ben Goehner's background and approach to land banking 03:20 The distinction between affordable and attainable housing 04:54 The collapse of small builders and market gaps 06:04 Western Dominion's approach to land and construction 07:00 The organic growth of their project and national potential 08:02 The importance of manufacturing and scale 11:05 Addressing land bank and public-private partnerships 11:57 Research efforts and university studies on rural markets 13:58 Innovations in modular and panelized building methods 16:00 Government programs like RED and infrastructure funding 16:52 Overcoming development bottlenecks and cost challenges 20:02 Scaling solutions nationally and manufacturing in Ohio 20:03 Challenges with large home builders and market competition 22:48 The future of off-site construction and local manufacturing 25:09 The importance of community-focused, attainable housing 27:03 Building community and local labor involvement 30:00 The impact of Western Dominion's model on housing affordability 30:13 Scaling solutions and the role of innovation in construction 34:54 The nonprofit element and community impact initiatives 40:11 The future vision: national standard panels and modular construction 45:02 Collaboration with other builders and industry players 50:00 The entrepreneurial journey and lessons learned 54:53 The importance of mission-driven business models 01:00:07 Closing thoughts and how to get involved ----- LINKS: https://www.linkedin.com/in/daniel-r-asbury-jr-3a3b24181/ https://www.linkedin.com/in/ben-goehner/ https://www.westerndlc.com/ ----- 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/

October 8, 202655 min

#264 Bernie Kosar

The timing of this conversation feels especially meaningful. Cleveland is moving to recognize October 13 as Bernie Kosar Day — honoring one of the most beloved figures in the city’s history and marking 41 years since his first regular-season start for the Browns. Bernie Kosar has spent his life figuring out a way — from a kid in Youngstown with an improbable dream, to becoming the quarterback of the team he grew up loving, to navigating extraordinary adversity far beyond the football field. Known and beloved as the legendary quarterback of the Cleveland Browns, Bernie’s story extends far beyond football. In this vulnerable conversation, Bernie and I reflect on the experiences that shaped him — the resilience, fear of failure, pain, and relentless belief that somehow, someway, you keep going. We explore his journey through addiction and bankruptcy, business and entrepreneurship, the health challenges that nearly took his life, and the perspective he carries today: deep gratitude for another chance at life, optimism about what lies ahead, and an enduring belief in Ohio and what can still be built here. I’m excited to share this conversation in advance of that recognition, and grateful to Bernie for being willing to reflect so openly on the extraordinary highs, lows, and lessons of his life. Please enjoy this special conversation with Bernie Kosar. 00:00 Introduction and Bernie’s background 02:07 Bernie’s health journey and recent transplant success 04:48 Resilience and persistence in life and football 08:49 From childhood dreams to NFL reality 13:02 The role of adversity in shaping success 16:50 Mental health, masculinity, and vulnerability 21:57 Bernie’s connection to Ohio and community pride 26:01 Optimism for Ohio’s future and economic growth 28:03 Lessons from sports applied to business and life 34:02 The impact of setbacks and bankruptcy 38:09 Bernie’s perspective on entrepreneurship and wellness 43:55 Collective ambition and community confidence 46:00 Reflections on playing for the Browns 49:56 Bernie’s message to the next generation 52:14 Hidden gems of Youngstown and local pride 53:50 Closing thoughts and gratitude ----- LINKS: https://x.com/BernieKosarQB?lang=en https://www.instagram.com/berniekosarofficial/?hl=en ----- 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/

September 30, 20261 hr 12 min

#263 Jeff Charney

Today is a special episode with Jeff—or, as you’ll come to learn, Jeffrey—Charney. Jeff grew up in rural South Carolina and went on to become a two-time Chief Marketing Officer of the year across firms like Progressive Insurance, Aflac, and QVC, helping shape some of the most enduring characters and concepts in modern marketing, including the Aflac Duck, Flo, Dr. Rick, and *many more.* But this conversation is less about his résumé than the patterns and philosophies underneath it: seeing around corners, advocating for real creativity and risk taking, and pursuing things that had never been done before— After leaving Progressive at the top of his career, that instinct took him to—founding MKHSTRY, building his digital twin Madison, and now working with neuroscientist Dr. Julius Fridriksson at ALLT.AI on a new approach to artificial intelligence inspired by the human brain rather than by language models, to vastly increase the efficiency and capability of AI as we understand it today. In our conversation, we explore why concepts endure while ideas expire, what meeting Muhammad Ali taught Jeff about people, the BRAND → BOT → BRAIN → BEYOND trajectory, why he walked away from Progressive at the top of his career, whether creativity and taste can be encoded into AI, why understanding how our brains work will teach us about building more efficient and explainable intelligence, and why the tallest nail gets hammered first. We also talk about time, discomfort, relevance, family, legacy, and why Jeff believes he’s never really been in the marketing business at all…. but rather in the business of history. Jeff is one of the most creative, highly intentional, and deeply caring people I’ve gotten to know and it is a real privilege to call him a friend and have him on here today — please enjoy my conversation with Jeff Charney 00:00 Introduction and Jeff Charney's background 02:08 The philosophy of being in the history business 04:42 The meaning of the nail metaphor and disruption 06:16 Jeff's roots and early influences in marketing 10:53 How Jeff sees around corners and makes history 12:22 The importance of concepts over ideas 17:45 Operating principles: change, growth, better, family 20:36 Knowing when to kill an idea 23:43 Why Jeff is drawn to unprecedented ideas 29:32 The future of AI and brain-based technology 36:03 The development of Madison and digital twins 43:12 Why Jeff waited to share his AI innovations 47:45 Jeff's legacy and the impact of AI on society 52:53 The importance of time, relevance, and authenticity 01:00:20 Inspiration from historic campaigns and creativity 01:07:32 The importance of being in the relevance and making history ----- LINKS: https://linkedin.com/in/jeffcharney ----- 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/

September 10, 20261 hr 15 min

#262 Paul Benner — Platform Beer Company

Paul Benner is the founder of Platform Beer Company. What began in 2014 as a tiny neighborhood brewery grew remarkably quickly through constant experimentation before ultimately being acquired by Anheuser-Busch in 2019. Platform was also personally meaningful to me…. with many formative conversations in my own entrepreneurial journey and life having occurred within its walls. In our conversation, Paul and I unpack the full Platform story—from his early interest in entrepreneurship and homebrewing, to Cleveland Brew Shop, Platform’s founding insight, hypergrowth, acquisition, COVID, and its eventual closure. We then explore what came after: separating his identity from the company, leaving and ultimately returning to Cleveland, going deep on Bitcoin and building a mining operation in West Texas, his thinking on money, inflation, affordability, and the K-shaped economy, and his return to beer as U.S. CEO of Pinter here in Cleveland. 00:00 Introduction and guest background 02:25 The significance of Cleveland and Platform's legacy 05:42 Early entrepreneurial influences and interest in beer 10:27 Starting the Cleveland Brew Shop and market insights 12:46 The power of doing and first-mover advantage 16:05 Launching Platform Beer Company 22:33 Growth, experimentation, and industry trends 28:09 Scaling challenges and navigating rapid growth 33:17 Impact of COVID-19 and strategic reflections 39:56 Post-Platform identity and exploring new ventures 42:15 Discovering Bitcoin and its influence 55:09 Building in the world of Bitcoin mining 01:00:11 The role of reading, learning, and curiosity 01:03:22 Reflections on success and happiness 01:08:13 Returning to Cleveland and local appreciation 01:11:33 Favorite hidden gems in Cleveland 01:13:22 Closing thoughts and contact information ----- LINKS: https://pinter.com/ ----- 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/

September 3, 20261 hr 1 min

#261 Gerald Hetrick — Round III (CentSight)

Gerald was one of the very first guests ever on Lay of The Land, back on episode 6, where we talked about his path through Vox Mobile, building Able, and what it took to grow a venture-backed software company from Cleveland. We then picked the story back up on episode 142 after Able’s acquisition by Bullhorn, exploring what an exit actually feels like, what Gerald had learned about company-building, and his work with Bezlio, Docket, and EOS. Today, we continue that arc with Gerald’s newest chapter: CentSight, an AI financial analyst platform designed to help founders and small business owners move from financial data to financial clarity, having just closed a $1.5m seed round. In our conversation, Gerald and I talk about what it feels like to build again after an exit, the evolution from pursuing success to pursuing happiness, what coaching other founders taught him about decision-making, the gap between financial fluency and financial honesty, how AI changes the speed and shape of company-building, and why Gerald is still committed to building from Cleveland. We also explore the tension between velocity and taste in the AI era, the importance of human judgment, and what it means to start from zero again with more experience, more humility, and still a lot of joy. Gerald is a thoughtful repeat founder, a candid operator, and someone whose story has become something of a living chronology of entrepreneurship on this podcast. Please enjoy my third conversation with Gerald Hetrick. 00:00 Introduction and Gerald's entrepreneurial background 03:34 Gerald's journey from Vox Mobile to SenseSite 07:55 The joy of building something new from scratch 11:31 Lessons from coaching entrepreneurs and EOS 17:55 Introducing SenseSite and its origin story 22:55 The core problem SenseSite addresses for SMBs 27:46 Building trust with AI products 33:00 The future of AI in finance and decision-making 41:45 Reflections on product market fit and team building 48:50 Gerald's current focus and excitement about the future 55:46 Gerald's thoughts on building in Cleveland 57:55 Closing thoughts and how to connect with Gerald ----- LINKS: https://centsight.com/ https://linkedin.com/in/geraldhetrick Episode 6: https://www.layoftheland.fm/6-gerald-hetrick-able/ Episode 142: https://www.layoftheland.fm/142-gerald-hetrick-part-ii-bezlio-eos/ ----- 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/

August 27, 202643 min

#260 Josh Friedlander — Jam by Josh

Joshua Friedlander — also known as The Jam Man — is the founder of Jam by Josh, a Cleveland-based small-batch jam company he started at just 10 years old. What began as a childhood love of cooking, gardening, and canning has grown from a backyard hobby into a formidable and rapidly expanding food brand, now sold in more than 75 stores across Northeast Ohio, Pennsylvania, Illinois, and beyond. At 16, Josh has taken Jam by Josh from his home kitchen to grocery shelves national wide. In our conversation, Josh and I talk about the origins of Jam by Josh, learning to sell through trial and error, what it takes to earn trust as a young founder, the persistence required to turn rejection into progress, scaling a food business, building a brand that makes jam feel fresh and exciting again, and what Cleveland has meant to his journey. Josh is the youngest guest we’ve had on Lay of The Land, and this was a genuinely inspiring conversation about bravery, persistence, and starting before you feel ready. Please enjoy my conversation with Joshua Friedlander. ----- LINKS: https://jambyjoshcle.com/ ----- 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/

August 13, 20261 hr 0 min

#259 Finn & Bowen Alexy — Alexy Metals & Bowfin Capital

Bowen and Finn Alexy are brothers, entrepreneurs, and investors based in Willoughby, Ohio. They serve as Co-Chief Operating Officers of Alexy Metals, a second-generation brazing alloy manufacturing and precious metals refining company, where they have helped lead the business through a period of significant growth while becoming the two youngest executives in their industry. Beyond manufacturing, they are the Co-Founders and Managing Partners of BowFin Capital, an early-stage venture investment platform focused on backing exceptional founders across healthcare, fintech, industrial technology, and consumer businesses. They became angel investors in a fast-growing New York City startup while still in their early twenties and are passionate about expanding access to entrepreneurship and early-stage investing. Finn and Bowen are the first brothers / dual recipients to ever receive Fast Track 50's Young Entrepreneur Award together, and recently became the first brothers in the 20-year history of the Cleveland Professional 20/30 Club’s Top 25 Under 35 list to be honored in the same class. Under their leadership, Alexy Metals was also recognized as Ohio Business Magazine’s Most Innovative Ohio Company in 2025. Through both operating businesses and investing in the next generation of founders, they are working to build enduring companies in Ohio while helping inspire more young people to pursue entrepreneurship. 00:00 Introduction to Bo and Finn Alexy and their business journey 02:07 The importance of innovation in legacy industries 03:02 The story of Alexi Metals and their industry niche 07:28 Explaining brazing alloys and precious metal refining 09:52 Innovating in an industry resistant to change 14:32 Valuable insights in scrap and recycling 16:45 Creating a circular economy in precious metals 22:24 Growth opportunities and market expansion 24:16 The role of technology and e-commerce 27:33 Building in Northeast Ohio and community impact 29:09 The origin of Bofin Capital and venture journey 36:16 Lessons learned from early investments and trust-building 40:01 Storytelling, narrative, and building brands 45:24 Leadership lessons from parents and ambition 50:48 Reflections on entrepreneurship and future goals 53:26 The value of building publicly and inspiring others 58:46 Closing thoughts and hidden gems in Cleveland ----- LINKS: https://alexymetals.com/ https://www.linkedin.com/in/finnalexy/ https://www.linkedin.com/in/bowenalexy/ ----- 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/

August 3, 202647 min

#258 Kumar Arora — Arora Ventures

Kumar Arora — entrepreneur, investor, brand-builder, and the founder of Arora Ventures, a venture studio and portfolio of businesses spanning hospitality, apparel, events, creative agency work, and consumer brands. Born and raised in Cleveland’s Little Italy, Kumar grew up between science and art, a duality that continues to shape how he builds today. In our conversation, Kumar and I explore the cohort of ambitious Clevelanders he came up alongside, his early path through nightlife, events, and entertainment, the lessons embedded in failure and reinvention, and how ventures like Sora, ILTHY, Underdogs, and FutureLAND reflect a broader vision for Cleveland — one rooted in creativity, collaboration, and the belief that this city can think bigger, see in color, and export far more of its talent, culture, and ambition to the world beyond it. 00:00 Introduction to Kumar Arora and Cleveland's Building Scene 00:27 Kumar's Background and Cleveland Roots 01:15 Changing Perceptions of Cleveland 02:11 The Cohort of Cleveland Disruptors 03:24 Early Entrepreneurial Ventures and Failures 05:17 The Role of Personal Taste in Business 06:24 LA vs Cleveland: Roots and Energy 07:59 High Standards and Ambition in Cleveland 08:53 Evolution of Entrepreneurship in Cleveland 10:25 The Importance of Human Connection 11:49 Arora Ventures: From Exit to Investment 13:17 Brand and Taste: Living, Breathing Systems 15:35 Can You Improve Taste? Insights from Kumar Arora 17:17 The Pillars of Kumar's Business Evolution 19:00 Systems and Processes in Portfolio Management 20:07 Lessons from Failures and Resilience 22:30 Working Towards Freedom and Empowerment 23:52 Cleveland's Unique Perspective and Color 25:30 The Subjectivity of Color and Perception 26:55 Building Cleveland's National Profile 28:22 Cleveland's Identity and Future Potential 29:19 What Keeps Kumar Arora Up at Night 30:17 Empowering Local Operators and Artists 32:53 Futureland and Supporting Black and Brown Entrepreneurs 35:12 Lessons from Restaurant to CPG Business 36:48 Building Relationships with Big Brands 40:08 Planting Seeds for Cleveland's Future 42:33 Upcoming Projects and Cleveland's Visibility 43:31 The Power of Collaboration and Local Pride 44:16 Follow Kumar Arora and Stay Connected ----- LINKS: https://www.kumar-arora.com/ ----- 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/

July 23, 20261 hr 4 min

#257 Alec Shankman — HeartRock Partners

Alec Shankman is the founder of HeartRock Partners. Alec has spent more than two decades at the forefront of entertainment, talent representation, reality television, digital media, podcasting, brand-building, and the creator economy. Before launching HeartRock, he was a Senior Partner at The Gersh Agency, following its acquisition of his division from A3 Artists Agency, where he built the Alternative Programming and Digital Media Division into a nine-figure 60-person bi-coastal team. In our conversation, Alec and I explore his path from Cleveland to LA and back again, how he built new lanes in Hollywood by being early to unscripted TV, digital talent, and creator-led brands, and why he returned home to launch HeartRock. We also talk about the shifting power dynamics in media, why talent is increasingly becoming the network, what separates fleeting attention from durable enterprise value, why work ethic still matters the most, and why Cleveland’s strengths in entrepreneurship, manufacturing, consumer products, and community make it a compelling place to build this next chapter. please enjoy my conversation with Alec Shankman. 00:00 Introduction and Alec's Cleveland roots 02:18 Alec's childhood exposure to entertainment 05:06 Seeds of a career in entertainment 06:45 Moving to LA and industry insights 09:59 Early waves of entertainment and Alec’s entrepreneurial approach 12:25 Leaving agency work to pursue entrepreneurship 14:54 Lessons from Hollywood and industry shifts 20:41 The evolution of media and talent representation 33:40 The vision behind HeartRock Partners 37:26 Why Cleveland? The geographic thesis 44:26 The creator economy and future opportunities 58:30 Looking ahead and Alec’s excitement for Cleveland 01:00:47 Closing thoughts and Alec’s advice for success ----- LINKS: https://www.linkedin.com/in/alecshankman https://heartrockpartners.com/ ----- 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/