InsTech - insurance & innovation with Matthew Grant & Robin Merttens Bootstrap Confidential Episode 11: Building a bootstrapped exit with Matthew Grant (390)
Jan 18, 2026
Matthew Grant, CEO and co-founder of InsTech, discusses his journey of building a bootstrapped company that achieved a successful exit. He shares insights on viewing bootstrapping as risk management, emphasizing the importance of paying oneself from the start. Matthew highlights the value of hiring curious early-career talent and maintaining control over decision-making without investors. He offers cautions about equity schemes, financial stress, and the reality of crafting a business around actual customer needs, not just personal aspirations.
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Hire Practical Freelancers Early
- Matthew hired a freelance bookkeeper from PeoplePerHour who grew with the company into a trusted finance lead.
- That low-cost, practical hire gave them reliable numbers without expensive fixed overhead.
Use Fractionals Strategically, Temporarily
- Use fractional specialists when you need expertise but avoid expecting full immersion from one-day-a-month roles.
- Hire fractionals to solve specific problems, then transition responsibilities in-house once processes are established.
Hire Curious Early-Career Talent
- Hire curious, early-career people who value exposure and rapid responsibility over salary.
- Offer fast career growth and real ownership of work to attract candidates you can't out-pay.
