Overcoming Failure and Rising Again - Ben Webster of AGILE Underwriting

Ben Webster, founder of Agile Underwriting Services, joins Dexter Cousins to discuss his journey as an entrepreneur in the insurtech space.

With a passion for developing innovative insurance platforms, Ben has successfully built and scaled multiple bootstrapped insurtech startups from the ground up, turning them into profitable businesses.

His extensive experience spans over 15 years, making him a true veteran in the industry. His deep understanding of the insurance landscape, combined with his technical expertise, enables him to drive transformative change and create meaningful value for both insurers and policyholders.

"The hardest problem is distribution. You can launch a product after 18 to 24 months of development, and then it's tumbleweeds." - Ben Webster

About AGILE Underwriting
Insurance brokers are being asked to do more with less with a range of tasks that drain time and eat profit.  With AGILE, brokers are discovering a more profitable way to sell insurance. AGILE Underwriting Services is a Lloyd’s cover holder and insurtech MGA specialising in Casualty, Construction, Cyber, Financial Lines, Retail Travel, Wholesale and more. Find out more - https://www.agileunderwriting.com/

About Todays show
We reflect on the impact of the COVID-19 pandemic on Ben's previous venture, Insured By Us, and the hard lessons he learned from that experience. Ben explains the success of the AGILE model focusing on niche insurance products and the benefits of having a diverse portfolio as he struggled to keep Insured By Us alive.
Ben also shares insights into the challenges of finding the right people, navigating distribution and dealing with regulation in the insurance space.

Some founder insights Ben shares in this episode:
- Agile's diverse portfolio has helped the business ride the wave of market fluctuations.
- The insurance industry is highly siloed, making it challenging to find people with expertise in specific niches who can be successful in a startup.
- Distribution is the most difficult aspect of launching an insurance product, and AGILE has developed strategies to validate products early on.
- Ben emphasises the importance of a growth mindset and the need for entrepreneurs to be comfortable with uncertainty and feeling uncomfortable.
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"The writing was on the wall, and I knew that I was going to have to make redundancies. I wanted to do it as early as possible to make sure that people got a good payout." - Ben Webster

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