Voices of PropTech by VendorPM

Navigating the Founder’s Journey: Insights and Lessons Learned with Josh Pillsbury

34 min · 8. juli 2025
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In this conversation, Josh shares his journey from aspiring lawyer to successful entrepreneur in the insurance tech industry. He discusses the challenges of balancing work and family life, the misconceptions he had about starting a business, and the emotional rollercoaster that comes with entrepreneurship. Josh emphasizes the importance of having a co-founder, finding fulfillment in his work, and the transformative potential of AI in the insurance sector. He concludes with advice for future entrepreneurs, highlighting the necessity of resilience and experience.

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episode Martin Kelly on Building, Scaling, and Betting Big in PropTech cover

Martin Kelly on Building, Scaling, and Betting Big in PropTech

In this episode of Voices of PropTech, Emiel Brill sits down with Martin Kelly, President of Blueprint, for a behind-the-scenes look at what it really takes to build one of the most influential events in the built world. They discuss the early risks, bold pivots, and leadership philosophy that turned Blueprint into a must-attend destination for founders, VCs, and real estate leaders. From scaling roundtables to redefining tech adoption in the space, Martin shares the moments that shaped his journey — and what most people don’t see behind the scenes. You’ll hear about: * The evolution of Blueprint and the power of event-driven ecosystems * Why risk, timing, and team culture matter more than ever * How founders and operators can better understand each other * The story behind Blueprint’s acquisition and what’s next Tune in for a candid, insightful conversation on leadership, growth, and the future of proptech.

22. mai 202546 min