Rajive Keshup is an Investor at Cathay Innovation. Prior to Cathay, he held roles at Strategy& and AT&T and has been an operator at startups in the region.

👋🏼 How would you explain your job to someone outside tech?

Every day, I get parachuted into a situation or an opportunity that may change the course of history, transform the world and shift value globally. Every. Single. Day.

I love what I do, and more importantly, I love the team I get to do it with at Cathay.

🧐 What's something about you or your job that would surprise us?

About the role: Venture Capital is not as glamorous as it looks. It is incredibly impactful (when done right!)

However, what may surprise you is that we spend more time than we would like to admit in deep research, interviewing experts to test new hypotheses, working on portfolio management, admin and reporting.

About me: I am less an investor and more an operator - Surprise! It is on that level where startup founders and I connect. I founded and sold my own business and have worked at startups and enterprises before as a CFO, so I typically take on an operator lens across everything I do.

I can relate to having to move mountains to make payroll every month, managing cash and runway and being unable to forecast with pinpoint accuracy. I have lived through all that, along with a couple of economic crises for good measure!

🏆 What has been the biggest highlight of your career so far?

I will give you four, because why not?

1) Attending business school at Cornell. That time, the post-financial crisis in 2010 truly changed the trajectory of my life. The classmates and professors I got to spend time with, the doors the Cornell alumni network opened up and the path I put myself on...all life-changing.

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2) Founding (and exiting) my own startup. What started as a side hustle in New York City took on a life of its own, and I am so grateful for taking the leap of faith with my wife and co-pilot!

We made SO MANY mistakes, but along the way, a few years of entrepreneurship in the toughest city in the world taught us more about business than any school or job ever could!

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3) Joining Cathay and getting to build out Southeast Asia and India for the firm with Nicolas Du Cray!

It's rare to find a partner that will back you unconditionally but, at the same time, is everything you are not. We are stylistically and individually polar opposites but deeply admire each other's opinions and are bonded by a common value set.

Joining Cathay and getting to learn every day from legends like Denis Barrier and Jacky Abitbol is easily a career highlight for me!

4) My first markup. Getting another set of investors you have a deep admiration for, to believe and have a high level of conviction in one of your portfolios, in the same way you do - is easily a career highlight for me.

By the time this goes live, there should be 1-2 other markups, but I'll never forget the way I felt the first time it happened. More so because I take an operator view of all this.

🔍 What's a startup trend or space you're watching this year?

In my heart of hearts, I am a SaaS investor, so I chase all the SaaSy stuff, horizontal, vertical, no code etc. These days I'm intrigued by trying to figure out the right relationship between CARR and ARR and the right mix at varying stages. More on this soon!

The best companies compound over time and become great businesses. Still, even these businesses will be impacted in the short term. Where I am spending time is trying to unpack which of these businesses truly flip the script from fire fighting mode to opportunistic, winner takes all machines!

💼 What advice would you give someone starting out in your industry?

If you are fresh out of school, don't start in VC. Go do something else, build some perspective on product or strategy and then layer your investing approach on top of that perspective.

While you are doing something else, if you can, write a handful of angel checks and keep track of that portfolio. It will help you understand where your biases sit and what types of businesses you naturally gravitate to!

🗣 What's one thing you can keep talking about for hours?

So many things! Food, New York City, cycling, my son and watches would probably be the Top 5 non-startup topics.

🎥 What's your favorite movie/TV show?

Seinfeld. I am a healthy mix of Jerry, George and Kramer...sometimes all at once! Just ask my teammates!

🍨 What's your go-to ice cream flavor?

Some combination of Dark Chocolate and Mint. After Eight?