01:35 – Shepherd’s big year: Growth and ambition
02:15 – Expanding beyond construction insurance
04:17 – Two antiquated industries collide
09:46 – The challenge (and secret) of hiring for insurtech
14:20 – Shepherd’s in-person work culture
19:42 – Founder reflections: current challenges and champagne problems
01:35 – Shepherd’s big year: Growth and ambition
Justin shares why 2025 has been the company’s most ambitious and fulfilling year yet, as Shepherd begins to reach greater scale and industry recognition beyond its early adopters.
02:15 – Expanding beyond construction insurance
The conversation reveals Shepherd’s aspirations to expand into other major sectors, such as energy, renewables, real estate, and agriculture, building on their success in risk management innovation.
04:17 – Two antiquated industries collide
Justin highlights how Shepherd sits at the intersection of two slow-to-evolve sectors: construction and insurance. Drawing from his early, clipboard-centric experiences, he explains why this makes their problem (and solution) so compelling.
09:46 – The challenge (and secret) of hiring for insurtech
Diving into recruitment, Justin discusses attracting both insurance veterans and top tech talent, and how they leverage the tangible, visible impact of their work in real-world projects as a unique draw.
14:20 – Shepherd’s in-person work culture
Justin explains the company’s commitment to in-office collaboration, particularly for product and engineering teams, and shares why being together fosters creativity, facilitates fast problem-solving, and promotes culture-building.
19:42 – Founder reflections: current challenges and champagne problems
As the episode wraps, Justin reflects on Shepherd’s current “champagne problems” — managing growth, resource allocation, and rapid iteration — underscoring his preference for these challenges over more fundamental startup issues.
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