Rajive Keshup

Partner, Cathay Innovation
Rajive, a former founder who exited a US pet-services company, is an operator-oriented SaaS investor—often founders' first call—who analyzes contracted-versus-reported ARR and writes on healthcare AI for MedCity News.
How to contact Rajive Keshup
Stages their fund invests in
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Sectors their fund invests in
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Avg Check
$5M - $40M
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Does their fund Lead?
No
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Geos their fund invests in
USA, Canada, LatAm, Europe, Asia-Pacific, India, Africa, Israel, MENA
Rajive Keshup
Stages their fund invests in
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Sectors their fund invests in
Fintech
AI
Consumer
Health
Energy
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Avg Check
$5M - $40M
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Leads?
No
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About Rajive Keshup

Rajive is a former founder who built and exited a US-based pet services startup before becoming a VC, and he approaches companies "less as an investor and more as an operator" while positioning himself as founders' "first phone call in great and not-so-great times." He describes himself as "in my heart of hearts, a SaaS investor" who digs into nuanced metrics like the relationship between contracted ARR and ARR at different stages, and he actively writes about healthcare AI as a MedCity News contributor, showcasing a cross-sector perspective that blends tech, healthcare, and data-driven transformation.

Rajive Keshup's Interests

What they've been talking about across their social media accounts
  • Strong conviction in the Indian market and capital efficiency. Frequently highlights regional economic growth, noting developments like domestic manufacturing and frugal innovation. A notable example is praising the national space program for executing a successful moon mission on a small budget, contrasting this directly with tech startups that raise massive funding rounds without generating any revenue.
  • Deep interest in artificial intelligence applications that create meaningful real world impact rather than just technical hype. Views finding AI solutions that genuinely change lives and human outcomes as a highly personal mission. Additionally, shows active involvement in the Southeast Asian AI ecosystem, recently speaking on local panels and championing diverse representation in tech.
  • Targeted focus on specific enterprise sectors like insuretech and cybersecurity. Actively participates in industry events for insuretech, referring to it as a favorite sector. For cybersecurity, points out that startups capable of solving complex multi layered security vulnerabilities at an enterprise scale will ultimately dominate the market.
  • High respect for bootstrapped entrepreneurs and resilient founder mindsets. Compares the bootstrapping journey to surviving a high stakes poker game from the very beginning, emphasizing that founders who endure early financial constraints can handle any future business challenges. Values proactive mentalities, advocating for immediate daily execution rather than waiting for the perfect moment to build.

About their Fund

Cathay Innovation

Sectors
Fintech, AI, Consumer, Health, Energy
Rounds
Series A - Series B+
Avg Check Size
$5M - $40M

Cathay Innovation operates as a unified global venture platform that connects startups with 20+ Fortune 500 strategic partners for active product co-development and commercial partnerships, while being structurally tied to a private equity platform that can support companies from early-stage through M&A. The fund positions startups as "transformation partners" rather than disruptors of incumbents, orchestrating collaborative relationships where large industrial players and startups co-build products and business models across highly regulated industries like healthcare, financial services, and energy.

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