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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 background02:07 Bernie’s health journey and recent transplant success04:48 Resilience and persistence in life and football08:49 From childhood dreams to NFL reality13:02 The role of adversity in shaping success16:50 Mental health, masculinity, and vulnerability21:57 Bernie’s connection to Ohio and community pride26:01 Optimism for Ohio’s future and economic growth28:03 Lessons from sports applied to business and life34:02 The impact of setbacks and bankruptcy38:09 Bernie’s perspective on entrepreneurship and wellness43:55 Collective ambition and community confidence46:00 Reflections on playing for the Browns49:56 Bernie’s message to the next generation52:14 Hidden gems of Youngstown and local pride53:50 Closing thoughts and gratitude ----- LINKS:https://x.com/BernieKosarQB?lang=enhttps://www.instagram.com/berniekosarofficial/?hl=en----- SPONSOR:Cerity PartnersCerity 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 InsuranceRoundstone 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/

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 background02:08 The philosophy of being in the history business04:42 The meaning of the nail metaphor and disruption06:16 Jeff's roots and early influences in marketing10:53 How Jeff sees around corners and makes history12:22 The importance of concepts over ideas17:45 Operating principles: change, growth, better, family20:36 Knowing when to kill an idea23:43 Why Jeff is drawn to unprecedented ideas29:32 The future of AI and brain-based technology36:03 The development of Madison and digital twins43:12 Why Jeff waited to share his AI innovations47:45 Jeff's legacy and the impact of AI on society52:53 The importance of time, relevance, and authenticity01:00:20 Inspiration from historic campaigns and creativity01:07:32 The importance of being in the relevance and making history ----- LINKS:https://linkedin.com/in/jeffcharney ----- SPONSOR:Cerity PartnersCerity 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 InsuranceRoundstone 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/

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 background02:25 The significance of Cleveland and Platform's legacy05:42 Early entrepreneurial influences and interest in beer10:27 Starting the Cleveland Brew Shop and market insights12:46 The power of doing and first-mover advantage16:05 Launching Platform Beer Company22:33 Growth, experimentation, and industry trends28:09 Scaling challenges and navigating rapid growth33:17 Impact of COVID-19 and strategic reflections39:56 Post-Platform identity and exploring new ventures42:15 Discovering Bitcoin and its influence55:09 Building in the world of Bitcoin mining01:00:11 The role of reading, learning, and curiosity01:03:22 Reflections on success and happiness01:08:13 Returning to Cleveland and local appreciation01:11:33 Favorite hidden gems in Cleveland01:13:22 Closing thoughts and contact information ----- LINKS:https://pinter.com/ ----- SPONSOR:Cerity PartnersCerity 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 InsuranceRoundstone 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/

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 background03:34 Gerald's journey from Vox Mobile to SenseSite07:55 The joy of building something new from scratch11:31 Lessons from coaching entrepreneurs and EOS17:55 Introducing SenseSite and its origin story22:55 The core problem SenseSite addresses for SMBs27:46 Building trust with AI products33:00 The future of AI in finance and decision-making41:45 Reflections on product market fit and team building48:50 Gerald's current focus and excitement about the future55:46 Gerald's thoughts on building in Cleveland57:55 Closing thoughts and how to connect with Gerald ----- LINKS:https://centsight.com/https://linkedin.com/in/geraldhetrickEpisode 6: https://www.layoftheland.fm/6-gerald-hetrick-able/ Episode 142: https://www.layoftheland.fm/142-gerald-hetrick-part-ii-bezlio-eos/ ----- SPONSOR:Cerity PartnersCerity 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 InsuranceRoundstone 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/

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 PartnersCerity 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 InsuranceRoundstone 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/

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 journey02:07 The importance of innovation in legacy industries03:02 The story of Alexi Metals and their industry niche07:28 Explaining brazing alloys and precious metal refining09:52 Innovating in an industry resistant to change14:32 Valuable insights in scrap and recycling16:45 Creating a circular economy in precious metals22:24 Growth opportunities and market expansion24:16 The role of technology and e-commerce27:33 Building in Northeast Ohio and community impact29:09 The origin of Bofin Capital and venture journey36:16 Lessons learned from early investments and trust-building40:01 Storytelling, narrative, and building brands45:24 Leadership lessons from parents and ambition50:48 Reflections on entrepreneurship and future goals53:26 The value of building publicly and inspiring others58:46 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 PartnersCerity 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 InsuranceRoundstone 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/

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 Scene00:27 Kumar's Background and Cleveland Roots01:15 Changing Perceptions of Cleveland02:11 The Cohort of Cleveland Disruptors03:24 Early Entrepreneurial Ventures and Failures05:17 The Role of Personal Taste in Business06:24 LA vs Cleveland: Roots and Energy07:59 High Standards and Ambition in Cleveland08:53 Evolution of Entrepreneurship in Cleveland10:25 The Importance of Human Connection11:49 Arora Ventures: From Exit to Investment13:17 Brand and Taste: Living, Breathing Systems15:35 Can You Improve Taste? Insights from Kumar Arora17:17 The Pillars of Kumar's Business Evolution19:00 Systems and Processes in Portfolio Management20:07 Lessons from Failures and Resilience22:30 Working Towards Freedom and Empowerment23:52 Cleveland's Unique Perspective and Color25:30 The Subjectivity of Color and Perception26:55 Building Cleveland's National Profile28:22 Cleveland's Identity and Future Potential29:19 What Keeps Kumar Arora Up at Night30:17 Empowering Local Operators and Artists32:53 Futureland and Supporting Black and Brown Entrepreneurs35:12 Lessons from Restaurant to CPG Business36:48 Building Relationships with Big Brands40:08 Planting Seeds for Cleveland's Future42:33 Upcoming Projects and Cleveland's Visibility43:31 The Power of Collaboration and Local Pride44:16 Follow Kumar Arora and Stay Connected ----- LINKS:https://www.kumar-arora.com/ ----- SPONSOR:Cerity PartnersCerity 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 InsuranceRoundstone 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/

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 roots02:18 Alec's childhood exposure to entertainment05:06 Seeds of a career in entertainment06:45 Moving to LA and industry insights09:59 Early waves of entertainment and Alec’s entrepreneurial approach12:25 Leaving agency work to pursue entrepreneurship14:54 Lessons from Hollywood and industry shifts20:41 The evolution of media and talent representation33:40 The vision behind HeartRock Partners37:26 Why Cleveland? The geographic thesis44:26 The creator economy and future opportunities58:30 Looking ahead and Alec’s excitement for Cleveland01:00:47 Closing thoughts and Alec’s advice for success----- LINKS:https://www.linkedin.com/in/alecshankmanhttps://heartrockpartners.com/ ----- SPONSOR:Cerity PartnersCerity 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 InsuranceRoundstone 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/5f0c1e28faConnect with Jeffrey Stern on LinkedIn — https://www.linkedin.com/in/jeffreypstern/ Follow Lay of The Land on X @podlayoftheland https://www.jeffreys.page/

David Gilbert is the President and CEO of Destination Cleveland and the Greater Cleveland Sports Commission. For more than three decades, David has worked to help Cleveland compete, attract visitors, host major events, and change the way the city is perceived — both by the outside world and by Clevelanders ourselves. Under his leadership, Cleveland has hosted events like the NFL Draft, NBA All-Star Game, MLB All-Star Game, NCAA Women’s Final Four, and the Republican National Convention, while Destination Cleveland has helped drive meaningful growth in visitation and visitor spending across the region. In our conversation, David and I explore what it means to get people to “say yes” to Cleveland, the evolution of the city’s brand and civic pride, the role of major events in building momentum, the importance of place branding, and the generational opportunity to reconnect Cleveland to its lakefront. David has been one of Cleveland’s most important civic storytellers and builders, and this was a thoughtful conversation about pride, perception, and helping a city more fully believe in itself — please enjoy. 00:00 The Mission to Change Perceptions of Cleveland08:30 David Gilbert's Journey and Community Engagement09:07 Understanding the Greater Cleveland Sports Commission and Destination Cleveland19:52 The Emotional Connection of Place Branding24:18 The Evolution of Cleveland's Brand and Local Perception27:27 Transforming Cleveland's Image30:48 Cleveland's Pride and Community Engagement36:48 The Future of Cleveland: Growth and Development44:02 Harnessing Cleveland's Natural Assets47:57 Hidden Gems of Cleveland51:23 Outro----- LINKS:https://www.linkedin.com/in/david-gilbert-26427b7https://www.clevelandsports.org/https://www.thisiscleveland.com/ ----- SPONSOR:Cerity PartnersCerity 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://www.ceritypartners.com/NPR or call 216-464-6266. Roundstone InsuranceRoundstone 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/

Duane Mancini, Founder and CEO of Project Medtech, a Cleveland-based platform helping medical technology companies move from promising invention to real patient impact. What began as a podcast has evolved into a broader ecosystem of consulting, events, education, investor connectivity, and community-building for Medtech founders navigating the difficult path from idea to market. In our conversation, Duane and I explore his path from science and research into entrepreneurship, how Project Medtech grew from a curiosity-driven podcast into a larger platform, and what founders often underestimate about building in Medtech. We talk about regulatory strategy, reimbursement, clinical validation, fundraising, the importance of team over product, and why Ohio may have a unique opportunity to become a more important node in healthcare innovation. Duane is thoughtful, mission-driven, and deeply committed to helping more life-changing technologies reach patients. Please enjoy my conversation with Duane Mancini. 00:00 Building Trust Through Storytelling07:53 The Evolution of Project MedTech12:30 The Entrepreneurial Journey Begins20:37 The Founding Team Dynamics23:43 Lessons from 250+ Conversations28:58 De-risking in Life Sciences33:38 Navigating Capital in Life Sciences38:35 Redesigning the Market Entry Process41:24 Understanding Economic Impact in Healthcare44:18 Measuring Impact and Success48:11 Optimism in Life Sciences and Med Tech50:46 Opportunities for Ohio's Life Sciences54:44 Building Supportive Ecosystems59:23 Outro----- LINKS:https://www.linkedin.com/in/duanemancinihttps://www.projectmedtech.com/ ----- SPONSOR:Cerity PartnersCerity 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 InsuranceRoundstone 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/

What does it take for AI to matter inside a real operating business? Not as a demo, not as a dashboard, and not as a generic productivity tool — but as something that answers calls, reduces clicks, quotes freight, improves service, and helps people spend more time doing the work that actually moves the business forward. Today we're republishing an episode from The O.H.I.O. Fund Report with Mark Kvamme — co-founder, CEO, and CIO of The O.H.I.O. Fund — Peter Coratola, founder and CEO of EASE Logistics, and Andy Jenks, co-founder of JAKIB.ai. Together, they unpack one of the clearest examples we’ve seen of applied AI in Ohio: a service-heavy logistics business navigating a difficult freight market, partnering with an AI company to start small, solve real operational bottlenecks, and eventually build Amy — an AI layer embedded directly into how EASE works. They discuss track-and-trace calls, customer service, quoting, user adoption, CEO-level ownership, and why AI at its best may be less about replacing people and more about multiplying their output. So please enjoy this conversation with Mark Kvamme, Peter Coratola, and Andy Jenks. 00:00 Introduction to the Ohio Fund and Ease Logistics05:12 Challenges in the Logistics Industry09:50 AI Transformation in Logistics13:55 First AI Project Implementation17:26 Integrating AI with Existing Systems20:12 User Adoption and Trust in AI23:20 Operational Efficiency and Cost Savings26:36 AI as a Knowledge Transfer Tool31:39 Lessons Learned in AI Implementation33:04 The Supercharged Engineer: AI's Impact on Productivity34:28 Empowering Non-Technical Users: AI for Everyone38:03 AI as a Multiplier: Enhancing Workforce Efficiency40:47 Customer-Centric AI: Transforming Client Interactions44:26 Mindset for AI Adoption: Insights for Business Leaders47:26 Evaluating Business Readiness for AI Implementation51:03 The Ohio Advantage: Why Midwestern Companies Thrive53:28 Future Predictions: The Next Big Leap in AI and Business----- LINKS: https://easelogistics.com/https://www.jakib.ai/https://www.linkedin.com/in/peter-coratola-jrhttps://www.linkedin.com/in/ajenks/https://www.linkedin.com/in/markkvamme/----- SPONSOR:Cerity PartnersCerity 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 ceritypartners.com/NPR or call 216-464-6266. Roundstone InsuranceRoundstone 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/

Teddy Baldassarre has built one of the most influential watch platforms in the world — and just as compelling as the watches themselves is the entrepreneurial story behind it. I first met Teddy almost ten years ago at StartMart in Terminal Tower, before any of this existed: before millions of followers, before the global audience, before the authorized retail partnerships, and before the beautiful physical boutique we recorded this conversation in at Crocker Park. In this episode, Teddy and I explore where his passion for watches began, how a first YouTube video evolved into one of the largest educational platforms in the watch world, and how he turned content into trust, trust into community, and community into a real business. We talk about entrepreneurship, self-expression, building online credibility, navigating the leap from digital media to commerce and physical retail, working with traditional watch brands, the enduring appeal of mechanical watches in an age where no one technically needs one, and what watches can teach us about craft, memory, status, meaning, and time itself. At its core, this is a conversation about building something that is an honest extension of who you are — and what can happen when curiosity, taste, discipline, and timing compound over the course of a decade. 00:00 Introduction & Meeting Teddy01:00 Early Days: Startups, YouTube Beginnings03:00 Discovering a Passion for Watches06:00 Watches as Craft & Self-Expression08:00 Turning Passion into Business & Monetization11:00 Launching E-Commerce & the Pandemic Pivot13:00 Brand, Community, and Content16:00 Building an Approachable Watch Platform18:00 Opening the First Store & Physical Expansion20:00 Partnering with Legacy Watch Brands22:00 Storytelling, Heritage, and the Value of Watches25:00 Watches in Modern Culture & Technology28:00 Entrepreneurial Learnings & Scaling a Personal Brand32:00 Team Building and Company Culture34:00 Pride, Impact, and Alignment with Life’s Work36:00 Building Trust Online38:00 Defining Success39:00 Personal Curiosity & The Future of Watchmaking41:00 Looking Ahead: Growth, Retail, and Community42:00 Why Cleveland? Building Local Roots45:00 Reflections on the Journey46:00 Cleveland Hidden Gems & City Pride49:00 Outro & Closing Remarks----- LINKS:https://www.youtube.com/teddybaldassarrehttps://teddybaldassarre.com/https://www.linkedin.com/in/teddy-baldassarre-70795890/ ----- 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/

Hochan (CJ) Jang is the co-founder of Balance Pan-Asian Grille. What began for CJ as an effort to build a healthier, more creative, and more everyday kind of Asian fast casual concept more than 16 years ago has grown into a beloved regional brand with locations across Toledo and Cleveland — one defined by scratch-made food, bold flavors, affordability, and a real commitment to hospitality. In our conversation, CJ and I explore his journey from growing up in his mother’s restaurant after immigrating from South Korea, to discovering the potential of fast casual, to building Balance with little more than conviction, credit cards, and a willingness to learn everything the hard way. We talk about how the business found its footing, why location and customer feedback were so pivotal early on, how he thinks about quality, pricing, and menu innovation today, and what it takes to scale a restaurant brand without losing the culture and standards that made it special in the first place. I very much enjoyed this conversation, and I think you’ll hear in CJ both a deep humility and a real love for the craft — I hope you enjoy it as well. 00:00 Introduction & Entrepreneurial Roots00:26 Welcome & Background03:00 Early Relationship with Food06:19 From Food to Entrepreneurship12:09 Inspiration from Fast Casual Concepts13:36 Challenges of Ethnic Fast Casual16:20 Launching Balance Pan Asian Grill19:40 Opening the First Location22:58 Importance of Location & Customer Feedback27:53 Balance’s Identity & Values31:07 Navigating Pricing & Affordability35:41 Scaling & Building Culture40:11 Vision for the Future44:57 Hard-Earned Lessons49:02 The Role of Upbringing & Community51:47 Closing & Hidden Gem in Cleveland----- LINKS:https://www.linkedin.com/in/hochan-j-88513510a/https://www.linkedin.com/posts/balancegrille_2-first-generation-entrepreneurs-are-redefining-activity-7351709996880998400-LM0l/https://balancegrille.com/the-balance-grille-leadership-advantage/https://balancegrille.com/story/ ----- SPONSOR:Cerity PartnersCerity 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 InsuranceRoundstone 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/

Aidan Meany, Founder and CEO of Found Surface. Aidan is building a programmable knitwear factory in Cleveland that is reimagining what American apparel manufacturing can look like What began for him with learning to sew from his grandmother and making clothes as a teenager has evolved into a much larger ambition — rebuilding the whole infrastructure to make apparel at scale here in the United States. Today, Found Surface develops its own yarn relationships from American farms and spinning partners, uses digital flatbed knitting and rapid assembly to make product close to home, and is building toward a future where brands can design, iterate, and produce without the waste, delay, and opacity of the traditional offshore model. In our conversation, Aidan and I explore the through line from his early fascination with clothing and making, to researching the fragmented state of American manufacturing during college, to building Found Surface first as a kind of supply chain connector and eventually into a serious manufacturing operation in Cleveland.  We talk about why he believes this city is uniquely suited for the work, the deeper thesis behind vertical integration and domestic production, how digital knitting changes the economics of speed, customization, and minimum order size, and why overproduction — not just outsourcing — sits at the heart of so much of the apparel industry’s dysfunction. We also discuss the partnership between Found Surface, the Cleveland Cavaliers, and the Cleveland Museum of Art, the company’s broader sustainability philosophy around natural fibers and proximity, the challenge of building an organization where young people can find meaningful work, and Aidan’s belief that Ohio has a real opportunity to help lead the next chapter of American industrial renewal. Aidan is a genuine inspiration and I hope you enjoy our conversation 00:00 Inflection Point in Apparel Manufacturing09:48 Found Surface: Origins and Evolution15:20 The Made in America Challenge21:43 Building a Smart Factory: The Future of Production30:30 Sustainability in Apparel: A Dual Approach35:08 Sustainable Fashion and Health Concerns41:29 Cleveland: A Hub for Innovation and Collaboration49:47 Rewriting History: The Future of Manufacturing55:19 Lessons in Leadership and Trust01:02:57 Outro----- LINKS:https://foundsurface.com/https://www.linkedin.com/in/aidanmeany ----- SPONSOR:Cerity PartnersCerity 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 InsuranceRoundstone 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/

This is the 250th episode of Lay of The Land, and to mark it, I wanted to do something a little different. Most episodes of this podcast are centered on founder stories — what drives someone to take the very difficult leap of trying to build a company, what problem they feel compelled enough to devote their life to solving, and what they learn along the way. But for this milestone episode, I wanted to step back and talk about the thing that ties these stories together… the community itself. And there was no one I’d rather have for that conversation than Chris Heivly. Chris is a serial entrepreneur, early-stage investor, startup community builder, and the founder of Build The Fort. He’s also was a co-founder of MapQuest, a bestselling author, a longtime writer and speaker on entrepreneurship and ecosystem development, and someone whose thinking had a real influence on the direction of Lay of The Land when I was starting it back in 2018…  Chris came to Cleveland in 2018 and shared his assessment of our startup community through Techstars and at the City Club, and a lot of what he said stayed with me and this podcast became my own attempt to act on it. Over the last 250 episodes, Lay of The Land has grown into something much bigger than I originally imagined — not just a repository of entrepreneurial stories, but a kind of connective tissue for entrepreneurship in Cleveland: dozens of events, thousands of introductions, new friendships, mentorship relationships, hires, investments, co-founders, and I’m sure many second- and third-order effects I’ll never fully know about. So for this episode, it felt worth reflecting more directly on this whole journey and linger on how entrepreneurial communities actually form, what makes them stronger, what gets in their way, and what that has looked like here in Cleveland. In our conversation, Chris and I talk about what he saw when he first came to Cleveland, why density and storytelling mattered so much in his original assessment, why founders have to be at heart of it, why confidence is contagious, why you have to build upon your credible strengths…we talk about the Give First mentality, about mentorship, trust, meaningful connection, the limits of top-down ecosystem design, and how cities actually get better. Chris has spent years studying how startup communities form, evolve, and endure. I’m grateful to Chris for joining me, and grateful to all of you who’ve listened, shared, supported, and helped make 250 episodes possible and will help make the next 250 possible. 00:00: Introduction07:40: Ecosystems13:02: Storytelling18:33: Give First24:34: Strengths in Community29:48: Meaningful Connections38:45: Human Complexity43:31: Mentorship48:51: The Role of Capital58:38: A Novel01:04:04: Reflections01:08:54 Outro ----- LINKS:https://www.linkedin.com/in/chrisheivly/https://heivly.com/https://buildthefort.com/City Club Talk: https://www.youtube.com/watch?v=Sc4zWbXURU8&t=2s ----- SPONSOR:Cerity PartnersCerity 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 ceritypartners.com/NPR or call 216-464-6266. Roundstone InsuranceRoundstone 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/