An Interview With Rajive Jain

6 hours ago
4 min read

Rajive Jain does not describe himself as a disruptor, but his thinking quietly challenges many of the assumptions that dominate modern investing. A former software professional turned private investor and founder, Jain built Kenshin Investments on a simple but disciplined belief: sustainable wealth is created through ownership, patience, and data-driven decision-making, not hype, speculation, or short-term trends.

What began as a personal shift away from a career that no longer aligned with his strengths has evolved into a firm focused on long-term value creation, scalable capital strategies, and businesses with the potential to compound over time. At Kenshin, Jain works with companies that are fundamentally strong but strategically underleveraged, helping them unlock growth through operational discipline and thoughtful capital deployment.

In this IndustryLeaders.org Q&A, Rajive Jain shares the philosophy behind Kenshin Investments, his views on global opportunity, the lessons that shaped his approach, and the principles guiding his leadership.

1. What inspired you to start Kenshin Investments, and how has your vision evolved since day one?

Rajive: I was miserable in a software job, but over time I had built strong investing skills. At the same time, I noticed more businesses coming to market that needed strategic capital to reach their goals. I decided to bring those two interests together. The vision itself hasn’t really changed. It has always been about helping individuals and companies build assets and enterprise value through stock ownership and capital events.

How do you define your role as both a founder and a private investor?

Rajive: The intent is exactly the same. As an investor, you aim to create returns. As a founder, you must create value and returns for the effort you put into your own enterprise. The mindset is identical.

In a competitive investment landscape, how do you differentiate Kenshin’s approach to value creation?
Rajive: We provide strategic investment approaches to building value inside companies. We also create scalable capital events for business owners who may not have considered financial structures that can significantly increase their exit value.

What leadership principles guide your decision-making, especially when the stakes are high?

Rajive: Pragmatism, and maintaining a non-emotional approach to capital allocation decisions.

How would you describe your investment philosophy in three principles?
Rajive: Let data do the talking. Keep emotion out. Always maintain a margin of safety.

What core criteria do you look for in a potential investment?

Rajive: The ability to generate above-average returns on capital, and the ability to scale that opportunity.

Can you share an investment that reflects your approach?

Rajive: We sourced and acquired a private education company with a strong geographic moat. The core business was good, but it hadn’t scaled to its full potential. By implementing operating systems, delegation pipelines, and scaling the sales function, we created the opportunity to triple the business.

How do you balance short-term performance with long-term value creation?

Rajive: Long-term criteria always override short-term results. Short-term performance often depends on luck aligning with the original premise. Over time, however, it’s not luck—it’s the numbers that confirm the thesis.

What role does ESG play in your investment decisions?

Rajive: For now, not much, since I am an investor rather than a direct operator within my portfolio companies.

Which sectors do you believe are most poised for disruption over the next decade?

Rajive: Infrastructure and energy. They will be essential to AI expansion, global business scaling, and addressing environmental challenges.

How is Kenshin positioned to benefit from macro trends like digital transformation?

Rajive: Digital transformation is really about efficiency. Wherever we see efficiency gaps, we see opportunity because reducing costs improves returns on capital.

What is your perspective on global diversification and cross-border investing?
Rajive: Diversification is really about avoiding fatalities, not diluting quality. Its purpose is to prevent complete wipeouts when things don’t go as planned, not to water down your best ideas.

How do you evaluate geopolitical risk when investing internationally?
Rajive: Much of it comes from a lack of understanding of international markets. Some of the world’s best compounders have come from places like Sweden. Deep value exists globally if you’re willing to look.

What is the biggest lesson you’ve learned as an investor?
Rajive: Avoid hype and conventional thinking. Many retail investors are taught not to beat the market, which leads to unhealthy habits like headline chasing and shiny object syndrome.

Is there a decision you would change in hindsight?
Rajive: Yes. I would have focused earlier on my top seven opportunities and ignored even the “good” ones that were less than excellent—and I would have started much earlier in life.

Who has influenced your thinking the most?
Rajive: Warren Buffett, Charlie Munger, Philip Fisher, Mohnish Pabrai, and Christopher Mayer.

What personal habits support your leadership effectiveness?
Rajive: Staying focused on positions without emotion, making decisions based on data, and constantly updating my knowledge through reading.

What goals excite you most for Kenshin Investments over the next five years?
Rajive: Growing the capital we manage and deploying more of it into high-return opportunities.

How do you see the role of private investment evolving?
Rajive: AI will make due diligence faster. I also believe businesses less affected by technological obsolescence may offer better long-term value.

What advice would you give the next generation of founders and investors?
Rajive: Be optimistically cautious. Learn from people who have actually practiced successful investing, not just from theory.