The IIT Madras founder who sold to Amazon & Walmart; Now owns a cricket team | Anand Rajaraman

Episode Summary

In this captivating episode, we sit down with Anand Rajaraman, a trailblazing tech entrepreneur, investor, and sports team owner. Anand takes us on an exhilarating journey from his days as a student at IIT Madras to becoming a pioneer of early internet innovation with Junglee, which was acquired by Amazon in 1998. 

The conversation traverses his remarkable career spanning venture capital investments (including being an early Facebook investor), his data-driven approach to VC with Rocketship, and his latest passion project as co-owner of the San Francisco Unicorns cricket team in Major League Cricket. 

Join Amrut and Anand as the latter shares invaluable insights on first-principles thinking, the thrill of zero-to-one innovation, and the fascinating parallels between entrepreneurship and T20 cricket. This episode offers a masterclass in recognizing opportunity, embracing calculated risk, and the delicate balance of luck and preparation in building transformative ventures.

Amrut’s Comment

When I was a student (IIT Madras, 2003-08), Anand Rajaraman and Venky Harinarayan were famous on campus as alumni who had sold their company, Junglee, to Amazon (in 1998). That's how I remembered Anand. Now I know that it was only the first chapter of a longer story.

He was in India last month, and I got lucky: we met for the Best Place to Build podcast. In my opinion, this is the best Build podcast we've done so far. Anand packed so much information in an hour, it's clear why he's so well-loved by one and all. 

Key Highlights

[00:01:22] Anand Rajaraman: A self introduction

[00:02:45] Junglee: The beginning, its use case and the founding team

[00:05:00] Acquisition by Amazon: The forest connection

[00:06:56] Junglee: The story behind the name

[00:10:25] The Washington Post: Junglee’s first investor

[00:12:30] Zero to One Journey: Why is it so special for Anand?

[00:14:58] Sports Team Owner: Taking cricket to America

[00:16:51] Major League Cricket: An overview of the format and the teams

[00:20:41] Anand as an Investor: His venture journey

[00:21:30] Facebook: Their first investment

[00:25:23] Mini Masterclass: Venture Capital firm and VC investing

[00:27:34] Data-Driven Venture Capital: How does that work?

[00:29:30] The Ph.D Journey at Stanford: Why does he call himself a failure?

[00:30:55] Foray into Teaching: 20 years of teaching and writing a textbook

[00:36:02] AI and Computer Science split: What does he think of the future of AI

[00:37:30] Collaboration with Venky Harinarayan: A journey that started with grocery shopping

[00:39:05] Kosmix: Evolution into Walmart Labs

[00:41:23] IIT Madras: An opportunity rich environment

[00:43:20] Medibuddy: Story of another IITM startup funded by Rocketship.vc

[00:45:00] Talk at ICSR: Beginning of the IITM entrepreneurial fund

[00:47:32] India’s Potential: Technical talent and big market for technology

[00:50:27] Advice for Parents and Students: What does joining IITM today mean?

Institutions mentioned

[00:00:13] IIT Madras 

[00:02:06][00:29:21] Anand went to Stanford University after graduating from IITM

[00:10:30][00:22:47] The Washington Post Company was one of the first companies to invest in Junglee

[00:16:51] Major League Cricket 

[00:18:22] Adobe’s CEO is also an investor in the San Francisco Unicorns

[00:37:51] Anand’s partner Venky studied in UCLA after IITM

[00:45:00] Anand gave a talk at ICSR about Entrepreneurship in 2012

People mentioned

[00:03:01][00:37:30] Venky Harinarayan was the co-founder of Junglee and Anand’s business partner

[00:03:07] Ashish Gupta was the co-founder of Junglee who is an alumnus of IIT Kanpur

[00:04:32] [00:45:25] Rakesh Mathur was the co-founder and CEO of Junglee

[00:05:06] Jeff Bezos is the founder of Amazon which acquired Junglee

[00:08:58] Sergey Brin and Larry Page, the co-founders of Google, were in the same batch as Anand.

[00:15:06] Anand mentions Indian cricket legend Kapil Dev as his inspiration

[00:17:48] Satya Nadella is the CEO of Microsoft who has also invested in the Seattle Orcas

[00:18:09] Anand talks about Nita Ambani being present at the Major Cricket League finals last year

[00:18:21] Shantanu Narayen is the CEO of Adobe who is also an investor in San Francisco Unicorns

[00:18:51] Shane Watson is the coach of the San Francisco Unicorns

[00:19:01] Ricky Ponting is the coach of the Washington Freedom team

[00:19:04] Amrut and Anand talk about how football picked up in the US after David Beckham went to the US and joined a football team 

[00:19:14] Pat Cummins is the Australian cricket captain who also plays for the San Francisco Unicorns

[00:21:45] Mark Zuckerberg is the founder of Facebook, now Meta.

[00:22:32] Sean Parker was the connection between Anand and Zuckerberg

[00:24:29] Anand mentions Rishabh Pant when he mentions how investing is like a T20 game

[00:30:47] Professor Hector Garica-Molina was a professor at Stanford

[00:31:37] Professor Jeffrey Ullman is a Turing Award winner and Anand’s co-instructor at Stanford

[00:33:10] Mayank Singh Bawa is the co-founder of Aster Data who was also a PhD student at Stanford

[00:36:57] Professor Balaraman Ravindran is the head of the AI Department at IIT Madras

[00:43:07] Sharan Jagathrakshakan is the co-founder and CTO of Mindgrove Technologies

[00:43:34] Satish Kannan and Enbasekar D are the co-founders of Medibuddy and an IIT Madras Alumnus

[00:45:50] Professor Bhaskar Ramamurthi was the former Director at IIT Madras

[00:46:04] Swaroop (Kittu) Kolluri, Arvind Purushotham and Rohini Chakraborty are all alumni of IIT Madras

Companies mentioned

[00:03:00] [00:37:53] [00:45:25] Junglee was Anand’s first venture - an online comparison shopping platform

[00:04:25] Amazon acquired Anand’s company Junglee where he had worked for 2 years

[00:08:44] Stanford students founded Google after Junglee

[00:09:07] Anand mentions Yahoo as another student-founded company which was a precursor to Junglee

[00:11:17] eBay was just getting rolling towards going public

[00:16:51] Anand is the owner of one of the Major League Cricket teams

[00:17:23] The Texas Super Kings are affiliated with the Chennai Super Kings

[00:17:33] The MI New York are affiliated with the Mumbai Indians

[00:17:38] The LA Knight Riders are affiliated with the Kolkata Knight Riders

[00:17:43] The Seattle Orcas have been invested in by Satya Nadella

[00:18:13] The San Francisco Unicorns are owned by Anand and his partners

[00:18:25] Washington Freedom is coached by Ricky Ponting

[00:20:48] Facebook, now Meta, was one of Anand’s early investments

[00:21:18] Kosmix was the second company founded by Anand after Junglee

[00:22:42] Accel is the VC firm that invested in Facebook

[00:23:50][00:37:53] Anand co-founded a VC fund called Cambrian Ventures

[00:27:36] Rocketship.vc which is Anand’s current VC firm is a data-driven VC firm

[00:34:07] Aster Data is a firm that was started by Mayank Singh and funded by Anand

[00:34:25] Aster Data was acquired by Teradata which is one of the biggest database companies in the world 

[00:39:25] Anand’s company Kosmix was acquired by Walmart

[00:39:29] Anand and Venky set up a group called Walmart Labs within Walmart

[00:43:10] Mindgrove Technologies is funded by Rocketship.vc

[00:43:25] Medibuddy is also an IIT Alumnus founded company that is funded by Rocketship.vc

[00:44:41] Ather and Hyperverge were founded in 2012 to 2014 - the same period as Medibuddy

Books & Other Media

[00:32:09] Anand and Professor Jeffrey co-wrote a textbook called Mining of Massive Datasets

Concepts & Models

[00:04:11] Comparison Shopping - The concept pioneered by Junglee that helped transform e-commerce

[00:06:09] Marketplace Model - The third-party seller platform that Anand helped develop at Amazon

[00:12:20] Zero-to-One Innovation - Creating something entirely new rather than incremental improvements

[00:13:17] First Principles Thinking - Questioning fundamental assumptions to find novel solutions

[00:16:25] T20 Cricket Format - The shorter, more action-packed cricket format suitable for American audiences

[00:25:05] Portfolio Theory in Venture Capital - Distributing investments across multiple companies to manage risk

[00:28:20] Data-driven Venture Capital - Using data analytics rather than networks to identify promising startups

Additional Links

Episode 12    |    54 Mins
Guest Bio

Anand Rajaraman is a distinguished tech entrepreneur, investor, and sports team owner. He is an alumnus of IIT Madras (class of '93) and Stanford University. After graduating from Stanford University, Anand co-founded Junglee, one of the first online comparison shopping platforms, which was acquired by Amazon in 1998. After his time at Amazon, where he helped build the Amazon Marketplace, Anand returned to Stanford to complete his PhD and discovered a passion for teaching, which he has continued for over 20 years. He co-founded Cambrian Ventures and Kosmix (acquired by Walmart), and continues to be deeply involved in the tech ecosystem through Rocketship.vc, a data-driven venture capital firm. Most recently, Anand has ventured into sports entrepreneurship as the co-owner of the San Francisco Unicorns cricket team in Major League Cricket, bringing his passion for cricket to the United States.

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