Bootstrap Confidential Episode 11: Building a bootstrapped exit with Matthew Grant (390)

Episode notes

This week we bring you an episode of Bootstrap Confidential featuring InsTech’s very own CEO, Matthew Grant, who joined Charles Green in the latter half of 2025 to reflect on the eight-year journey of building InsTech from the ground up without outside funding, and with an intentional focus on sustainable growth. Matthew’s route to growing InsTech wasn’t typical. With a background in risk, analytics and around 400 podcast episodes as a host, he brought a deep understanding of the insurance sector and what it takes to build a commercially viable, insight-led business. The result? A thriving community of over 30,000, a high-margin membership model and a successful exit achieved through discipline, focus and clear-eyed decisions.

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