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.

In this conversation, Matthew shares:

Why he sees bootstrapping as risk management, not risk taking
The importance of paying yourself from day one and how that shaped InsTech’s trajectory
Lessons from testing (and killing) products that didn’t deliver
Why hiring curious, early-career talent paid off
What most founders get wrong about option schemes and equity
How to handle financial stress without losing your team or your sanity
Why co-founders matter and why investors aren’t a substitute
The hard truth about building the business your customers want, not just the one you’d love to run

If you like what you’re hearing, please leave us a review on whichever platform you use or contact Matthew Grant on LinkedIn.

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

InsTech - insurance & innovation

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