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This episode is from the Bootstrap Confidential podcast, featuring InsTech CEO Matthew Grant in conversation with Charles Green. Matthew shares the eight year journey of building InsTech from the ground up without outside funding, growing a 30,000 strong insurance community and achieving a successful exit through disciplined, sustainable growth. The discussion covers bootstrapping as risk management, paying yourself from day one, testing products quickly and focusing only on what customers will actually pay for. Topics include: -Why Matthew sees bootstrapping as risk management, not risk taking -Paying yourself early and building a profitable business from day one -Lessons from testing and killing products that did not work -Hiring curious early career talent and growing leaders internally -What most founders misunderstand about options and equity -Managing financial stress and near cash crunch moments -Why co-founders matter more than investors -Building the business customers want, not the one you wish existed 👉 Listen on your preferred podcast platform: https://www.instech.co/knowledge-cent... 📌 Subscribe for more InsTech podcast episodes: / @instechofficial 🔍 Explore the InsTech podcast archive: https://www.instech.co/item-type/podc... --------- If you enjoy the episode, please leave us a review or 📨 Contact Matthew Grant: / matthewjggrant 🗞️ Sign up to the InsTech newsletter: https://www.instech.co/sign-up-to-the... 🎙️ Leave us a voice message: https://www.speakpipe.com/widget/inli... --------- 00:00 Why we started InsTech 01:30 From corporate career to bootstrapping 04:00 Paying yourself from day one 06:00 Profitability vs growth trade-offs 08:00 Testing and killing products fast 10:00 Monetising events and membership 12:30 Hiring curious early career talent 15:00 Options, equity and founder mistakes 18:00 Cash crunch moments and survival 22:00 Why co-founders matter 25:00 Preparing for exit 29:00 Lessons for founders