Endeavor Unfiltered ft Rajat Bhargava (Co-Founder & CEO, JumpCloud)
10th Time’s a Charm
What does it take to build a company not once, not twice, but ten times?
Endeavor Unfiltered is a founder sharing session that goes beyond the success stories to explore what entrepreneurship really looks like: the mistakes, hard decisions, failures, breakthroughs, and hard-earned lessons that shape a builder over time.
For this edition, we’re sitting down with Rajat Bhargava, ten-time entrepreneur, investor, author, and Co-Founder of JumpCloud, to unpack what more than two decades of building companies has taught him about resilience.
With seven exits, including two IPOs and five trade sales, Rajat has experienced entrepreneurship across multiple cycles: starting from zero, scaling teams and companies, navigating setbacks, exiting, and choosing to do it all over again.
It will be a candid conversation about what changes, and what doesn’t, after ten companies. How do you recover when things go wrong? How do you know when to persist, pivot, or walk away? Does experience actually make entrepreneurship easier? And perhaps most importantly: after nine companies, what makes someone want to build a tenth?
No polished playbooks. No highlight reels. Just an honest conversation between founders about what it really takes to keep building.
🔥 About Rajat Bhargava
Rajat Bhargava is an entrepreneur, investor, author, and Co-Founder of JumpCloud. An MIT graduate with over two decades of high-tech experience, Rajat is a ten-time entrepreneur with seven exits, including two IPOs and five trade sales.
🚀 About JumpCloud
JumpCloud powers modern work by intelligently and securely connecting every identity, device, and agent to the access they need. JumpCloud has raised over $400M, most recently closing a $225M Series F at a $2.6B valuation, and today serves organizations across 160+ countries. Its investors include Sapphire Ventures, General Atlantic, BlackRock, CrowdStrike, Atlassian Ventures, and Endeavor Catalyst.
✨ About Endeavor
Endeavor is the leading network of entrepreneurs scaling exceptional businesses around the world. For 30 years, Endeavor has searched for, selected, and supported founders scaling extraordinary companies outside Silicon Valley and China. Its goal is to establish thriving entrepreneurial ecosystems in places where talent is abundant, but access is not. Today, Endeavor's Global Network of Trust encompasses 3,100+ entrepreneurs across 50+ countries. Endeavor guides these founders through pivotal moments in their journeys and encourages them to mentor and invest in the next generation of entrepreneurs — an impact Endeavor calls the Multiplier Effect. It's time to redraw the innovation map. It's time to look Elsewhere.
🇸🇬 About Endeavor’s Global Hub in Singapore
Endeavor’s Global Hubs are strategic innovation nodes in the world’s most connected cities. Launched in 2026, Endeavor’s Global Hub in Singapore creates a second home for diaspora entrepreneurs building beyond their original markets, and connects exceptional local founders with global mentors, investors, and operators. The Global Hub also anchors foreign scale-ups and accelerates local ones in alignment with Singapore’s recent Economic Strategy Review.
Founders will be prioritized to join the session. Come ready for an open, candid conversation.