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: Introduction
07:40: Ecosystems
13:02: Storytelling
18:33: Give First
24:34: Strengths in Community
29:48: Meaningful Connections
38:45: Human Complexity
43:31: Mentorship
48:51: The Role of Capital
58:38: A Novel
01:04:04: Reflections
01:08:54 Outro

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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

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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 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/

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