1Mby1M Virtual Accelerator AI Investor Forum: With Sailesh Ramakrishnan, Managing Partner at Rocketship.vc (Part 1)

Sailesh Ramakrishnan, Managing Partner at Rocketship.vc, discusses his AI investment thesis and shares his firm’s use of AI in monitoring investment-worthy startups.

Sramana Mitra: Today, we’re going to start the conversation with Sailesh Ramakrishnan, managing partner of Rocketship VC. Sailesh, welcome to the show. I’ve known Venky and Anand for a long time, so I’m very happy to meet you. And this is going to give us an opportunity to get to know each other a bit.

Sailesh Ramakrishnan: Absolutely, thank you so much for having me.

Sramana Mitra: So Sailesh, why don’t we start with a little bit of introduction about yourself and Rocketship.vc, and then we’ll dive into the core topic on the table today, which is AI investments.

Sailesh Ramakrishnan: Anand, Venky, and I had started Rocketship back in 2014. Anand and I are classmates from IIT Madras. Venky is also from IIT Madras. We actually shared the same dorm. I came to the Bay Area when I started a job at NASA, at the Ames Research Center, where I was working as a computer scientist on the Mars Rover project for about four years. I thought working at NASA was dream come true. When I was a kid, I actually wanted to be an astronaut, but at least it was fulfilling to at least work at NASA. But then I discovered an even greater passion, if you will, and that happened to be startups.

I left NASA when Anand and Venky were starting their second company. I joined them early in that company, and I really enjoyed this journey of going from zero to one or starting things from scratch. You’re empowered to pretty much build anything, see it go out into the wild, and see if people like it. So with that experience, I really learned a lot about building startups, building software, and working on things that eventually become very large in scale. As a consequence of our approach, we were acquired in 2011 by Walmart.

We went into Walmart as a new division called Walmart Labs, which was supposed to be the innovation arm at Walmart. That gave me an even more different and interesting perspective working at Walmart scale. Walmart was and perhaps still is the world’s largest retailer. There was a lot of opportunity to figure out how to do things that we were interested in doing, but at Walmart scale.

But at the same time, I still had a remnant wish. While I had worked with Anand and Venky in their startup, I had not founded a startup myself. There were several ideas that we had developed along the way. So, a coworker and I decided to start a company. So in 2011, about 6-7 months at Walmart, I decided to start this company. Anand and Venky were one of the earlier investors in the company.

We created a marketing platform for small and medium sized businesses; and in 2014, we were acquired by Square, the cash register company. That’s when I had another decision point. I could have continued with Square do something new. I was really excited to go back once again and try and do something from zero. So, the three of us got together to start Rocketship.vc.

Rocketship.vc is a global VC, very similar to your podcast. We’ve investments in 14 different countries, 20 different sectors. The key innovation we are bringing to the process of venture capital is that we use AI and machine learning algorithms to find a prospective investment candidates. We have one of the largest databases of startup data of about 400TB. We’ve multiple families of machine learning algorithms that run on this data set every day and recommend which are the hottest companies for us to reach out to. Also inside these algorithms, there’s a lot of cutting edge GenAI algorithms at work that help us understand the large amounts of unstructured data that is available about startups,

To quickly summarize where we are with Rocketship.vc, we manage just over $250 million invested in companies globally. We are an early stage investor. Most of our investments are clustered around the Series A, but we have investments earlier than that as well as at seed level. We have also invested in companies that are at the Series B stage. So, this approach has actually allowed us to find some of the best companies in the world and have the opportunity to invest in them.

Some of the notable investments are several Indian companies- B2B e-commerce provider Moglix, India’s most recent space launch company Agnikul, and Wasabi, which is one of the largest storage companies and a competitor of Amazon S3.

Rocketship.vc also happens to balance out our multiple interests. It gives us an opportunity to live, for a tiny bit of time, the startup life vicariously through most of our entrepreneurs. In a sense, we are also building something from scratch. It also allows us to scratch our computer science itch. We are actively building these algorithms on a daily basis. It’s always an interesting challenge to figure out how to improve these algorithms.

Sramana Mitra: So Sailesh, Rocketship does both B2B and B2C, right?

Sailesh Ramakrishnan: That’s correct.

This segment is part 1 in the series : 1Mby1M Virtual Accelerator AI Investor Forum: With Sailesh Ramakrishnan, Managing Partner at Rocketship.vc
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