Introducing Cowbell

Stephanie Khoo
2 min readMar 15, 2022
Cowbell Co-Founders Prab Reddy, Jack Kudale, Rajeev Gupta and Trent Cooksley

Today, we are ecstatic to announce our investment in Cowbell, alongside lead investor Anthemis (shout out to Matt Jones!) and co-investors Permira, PruVen and Viola. As we’ve said before, at Nyca, we view our job as finding great entrepreneurs, attracting great teams, while addressing real problems. We continue to be impressed by Cowbell co-founders Jack Kudale, Prab Reddy, Rajeev Gupta and Trent Cooksley. Many companies are beginning to recognize that cyber insurance is increasingly a must have product, but the product is notoriously difficult to underwrite and distribute.

Our solution? More Cowbell.

Our focus on cyber insurance was driven by compelling macro and micro trends:

  • Greenfield TAM — one of few product lines where TAM is growing exceptionally quickly (global cyber CAGR ~25+%; vs. auto ~9% and home ~7%). Coverage is fast becoming a pre-requisite to doing business, especially in a post-covid world where remote work and an increase in cashless transactions has presented more opportunity for cyber breaches. As digitization continues, “cyber insurance” will simply become synonymous with “insurance”.
  • Low penetration — despite cyber attacks having increased in both frequency and severity, coverage, especially among SMB’s, remains low.
  • Incumbents have no competitive advantage in data — unlike auto and home, where incumbent carriers have over a century worth of data; cyber is a new line and presents a more even playing field.
  • Prevention is paramount and insurtech can attract strong engineering talent — a robust and continuous monitoring program is essential to underwriting profitably, and insurtechs are able to cultivate a professional culture that attracts top tier talent.
  • Silent cyber — incumbent carriers are more likely to face unexpected cyber exposures through existing general liability and business owners policies where language remains ambiguous on cyber. Standalone cyber policies are better positioned to avoid uncertainty.

So, why Cowbell?

I’ll keep it brief.

✅ Phenomenal team — wildly intelligent individuals, collaborative work culture, unparalleled commitment to diversity. ⭐️⭐️⭐️

✅ Strong underwriting, pricing, monitoring— outside-in, inside-out, innovative monitoring capabilities, collaborative dashboard.

✅ Balance sheet capacity — impressive redundancy despite a hardening market, driven by best-in-class loss ratios.

✅ Shared risk dial — continuous monitoring that provides carrier and policyholder with equal transparency, aligning incentives to minimize loss.

Amazing distribution — multi-channel and secret sauce!

✅ Traction 🚀 — as measured by growth in revenue, no. of policies, size of policies, no. of products, capacity, employees, distribution / producers, etc.

We recognize that the cyber insurance journey will be a rollercoaster 🎢 over the next decade, but we couldn’t have found a better group of thrill-seekers to join the ride!

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