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On this special milestone episode of FNO: InsureTech, Rob and Lee turn the microphones inward to reflect on seven years of recording, learning, and showing up. What began in 2018 at 470 Claims with an iPhone on a desk and no real expectations has grown into 300 conversations spanning insurance, InsureTech, startups, and emerging technology.

They walk through the genesis of the podcast and why the earliest recordings were driven more by curiosity than strategy. What started as a side project quickly became a consistent forum for thoughtful, unscripted conversations, shaped as much by listening as by asking questions.

From APIs to AI and everything in between
Rob and Lee revisit how the topics covered on the show evolved alongside the industry itself. Early conversations focused heavily on APIs, data access, and connected ecosystems. Over time, those discussions shifted toward artificial intelligence, large language models, and agentic intelligence, reflecting how innovation in insurance moved from infrastructure to interpretation and decision making.

They unpack how this progression mirrors a deeper change in how InsureTech companies think about value, moving beyond simply moving data to understanding it and acting on it in real time.

The shifts nobody talked about but everyone made
Looking back across seven years, Rob and Lee discuss the quieter changes they observed between 2018 and 2025. These were not headline grabbing pivots, but subtle shifts in mindset, operating models, and expectations that slowly became industry norms. Many startups adopted them out of necessity, even if they rarely acknowledged the change publicly.

They reflect on what these shifts reveal about maturity in the InsureTech ecosystem and why some ideas aged better than others.

Relationships, networking, and what surprised us most
One of the biggest surprises from 300 episodes was not a technology trend or business model, but the relationships and networking that emerged organically through the podcast. Rob and Lee share how conversations often extended far beyond the recording, turning into long term connections that reshaped how they view community within the industry.

Looking back with clarity
Rather than a victory lap, Episode 300 is a moment of perspective. Rob and Lee reflect on what consistency taught them, how their own thinking changed over time, and why staying curious mattered more than being right. The episode offers a rare behind the scenes look at how the podcast grew, not through virality or hype, but through patience and genuine interest.

Listeners come away with a thoughtful reflection on what seven years of conversations can teach you about an industry, about people, and about the value of simply pressing record and seeing where the discussion goes.

Listen to Episode 300 wherever you listen to podcasts.