Best Place To BuildAnand Rajaraman| The IIT Madras founder who sold to Amazon & Walmart; Now owns a cricket team| Ep.12
CHAPTERS
Back at IIT Madras: Reunion vibes and Anand’s multi-hyphenate identity
The host sets the scene at IIT Madras’s innovation hub during Saarang (formerly Mardi Gras) and introduces Anand Rajaraman as entrepreneur, deep-tech investor, and now sports team owner. Anand reflects on the campus energy and frames his journey from IITM ’93 to Stanford and beyond.
- •IIT Madras setting, Saarang/Mardi Gras nostalgia
- •Anand’s background: IITM ’93, Stanford, startups, investing
- •Positioning: entrepreneur + investor + sports team owner
- •Theme teased: building and “zero to one” creation
Stanford PhD research that became a startup: data integration meets the early web
Anand describes the research problem he and collaborators worked on at Stanford: integrating data across multiple systems. They realize the web—not corporate databases—will hold the world’s most valuable information, and they aim to enable structured queries on top of it.
- •Information/data integration as the original research area
- •Insight: the web will be the most important data source
- •Focus on structured queries (not keyword search)
- •Early use case: product discovery and price comparison
Founding Junglee: inventing online comparison shopping
The team turns research into product, effectively pioneering comparison shopping by aggregating structured product information from the web. Anand outlines the founding team, early roles, and his decision to pause (effectively drop out of) the PhD to build the company.
- •Junglee’s founding team (Venky, Ashish, Rakesh, Anand)
- •Building a tech stack to compare products/prices online
- •Leaving the PhD program to pursue the startup full-time
- •Early internet era constraints: servers, hosting, physical infrastructure
Amazon acquires Junglee: helping create the Amazon Marketplace
Amazon approaches Junglee in 1998, when Amazon is newly public and mostly a bookseller. Anand explains Bezos’s vision for “everything store” and how Junglee’s technology helped enable third-party merchants—what becomes the Amazon Marketplace.
- •Timeline: founded 1996, acquired 1998
- •Amazon’s early stage: small company, post-IPO, books-focused
- •Strategic rationale: expand beyond books using web-derived product info
- •Junglee team’s impact: building foundations of Amazon Marketplace
Why the name ‘Junglee’ stuck: a pitch-night joke, a marketing story, and investor skepticism
Anand tells the origin story of the name “Junglee,” which started as a playful follow-on to “Yahoo!” and later gained a navigation-the-internet-jungle narrative. He also shares how Washington Post invested but disliked the name, and how the founders managed that tension.
- •Naming constraint: needed an available .com in the 90s
- •Name origin: “Yahoo… Junglee” joke becomes brand
- •Created a ‘internet is a jungle’ story after the fact
- •Washington Post invests but calls the name ‘not corporate’—founders keep it anyway
The “zero to one” addiction and first-principles thinking
Shifting from story to philosophy, Anand explains why he’s drawn to creating new categories and taking on hard, risky problems. He defines first-principles thinking as questioning hidden assumptions in established approaches to unlock novel solutions.
- •Motivation: doing new things before others (‘to boldly go…’)
- •Tradeoff: high risk/high reward and the pain of early creation
- •First principles: uncover and challenge unstated axioms
- •Novel solutions often come from rejecting conventional constraints
Taking cricket to America: why now works (community + T20 format)
Anand connects his lifelong cricket fandom to a practical thesis for the U.S.: there is now enough cricket-aware population (especially South Asians) and a format (T20) that fits American attention and event schedules. He frames it like a founder would—market timing plus product-market fit.
- •Personal origin: growing up with iconic cricket moments (Kapil Dev era)
- •U.S. thesis: critical mass of cricket fans (millions)
- •Format innovation: T20 fits ~3-hour sports consumption
- •Founder lens: timing, market readiness, and distribution (streaming, diaspora)
Major League Cricket (MLC) explained: teams, cities, IPL affiliations, and the Unicorns
Anand breaks down the structure of Major League Cricket: six teams across major U.S. metros, some affiliated with IPL franchises. He details the San Francisco Unicorns ownership group and how recognizable global cricket talent helps legitimize the league.
- •Six teams: Seattle, SF, LA, NY, DC, Dallas
- •IPL linkages: CSK (Texas), MI (NY), KKR (LA)
- •Anand & Venky as majority owners of San Francisco Unicorns
- •Star power: coaches/players (e.g., Shane Watson, Pat Cummins) as adoption catalysts
The live stadium experience: intimacy, proximity, and “talk to your customers”
Anand describes walking the stands and speaking to fans to learn what they value—an entrepreneurial habit applied to sports. A key advantage versus watching cricket elsewhere is the smaller, more intimate venues that bring fans closer to the action.
- •Customer discovery mindset applied to sports product
- •Fans value proximity and intimacy in smaller stadiums
- •Community experience as a differentiator vs. major venues abroad
- •Building fandom through engagement and feedback loops
Venture capital journey and the Facebook investment story (via Stanford signals)
Anand recounts how he and Venky noticed Facebook early by observing student attention at a Stanford panel with Mark Zuckerberg. A later connection—Zuck evaluating Accel vs. Washington Post—creates the opening for them to invest personally.
- •Early signal: disproportionate student interest in Zuckerberg at Stanford
- •Due diligence triggered by observing real user pull
- •Full-circle link: Washington Post relationship from Junglee days
- •Angel investment (not via fund) after Accel-led round
How VC works: portfolios, power laws, and entrepreneur vs investor control
The episode pauses to explain venture capital for younger viewers: funds pool money, buy equity in startups, and rely on a small number of outlier wins to return the fund. Anand contrasts the control entrepreneurs have over one bet with investors’ diversification across many bets.
- •Definition: pooled capital investing in startup equity
- •Portfolio math: many failures, a few break-evens, rare 10–100x winners
- •Entrepreneur control vs investor diversification tradeoff
- •Luck + preparedness as recurring ingredients in outcomes
Data-driven venture capital at Rocketship: inverting the sourcing model
Anand explains Rocketship’s thesis: instead of relying on warm intros and networks, build a global dataset of startup activity and use machine learning to identify promising companies. The fund then proactively reaches out to founders, broadening access beyond elite networks.
- •Traditional VC relies heavily on referrals and networks
- •Rocketship builds a database via licensing + web crawling
- •ML models surface emerging companies earlier
- •Outbound approach: investors approach founders, not the reverse
Staying technical: finishing the PhD, teaching at Stanford, and deep-tech investing
Anand revisits his academic arc: returning to Stanford after Amazon to complete his PhD, then discovering he loves teaching. He shares his long-running teaching involvement (distributed systems, then data mining), and how academia becomes a pipeline for deep-tech ventures.
- •Return to Stanford post-Amazon to complete thesis/PhD
- •Teaching starts via faculty request; becomes a 20-year habit
- •Data mining course grows with ‘big data’ wave; textbook creation
- •University ecosystems as a source of deep-tech startups
Long-term co-founder partnership with Venky: from grocery runs to Junglee, Kosmix, and Walmart Labs
Anand tells how he met Venky at Stanford (not IITM) and how their collaboration endured across decades. He then traces Kosmix (an early AI-ish company) to its acquisition by Walmart and the creation of Walmart Labs as a tech brand to compete with Amazon—plus building Walmart Labs Bangalore.
- •Met at Stanford due to different IITM graduation years
- •Shared advisor and research collaboration → startup co-founding
- •Kosmix acquisition by Walmart (2011) and mandate to compete with Amazon
- •Walmart Labs branding to attract talent; Bangalore office seeded early
IIT Madras as an ‘opportunity-rich environment’: co-founders, mentors, seed funds, and breakout startups
The conversation returns to IITM’s ecosystem: the value of co-founders, mentorship, and brand effects that improve a startup’s odds. Anand highlights investments/mentorship in IITM-linked companies like Medibuddy and HyperVerge, and recounts how a 2012 talk catalyzed the IITM Entrepreneurship Fund that helped seed multiple ventures.
- •Core advice: find stress-tested co-founders; IITM is ideal for this
- •Mentorship flywheel: alumni eager to help founders
- •Examples: Medibuddy’s scale and IITM’s equity model creating returns
- •2012 ICSR talk → IITM Entrepreneurship Fund → stronger incubation ecosystem
India’s tech moment + advice to students and parents: branches matter less than networks
Anand gives a VC-style view of India: both a massive talent pool and a rapidly adopting market—much stronger than in 1993. He advises parents/students not to over-index on branches (CS vs others), arguing IIT’s peer group, problem-solving training, and alumni network dominate long-term outcomes, then closes with a reminder to enjoy college.
- •India thesis: talent + huge market; stronger now than 90s India
- •Trend shift: fewer IIT grads feel compelled to leave for the U.S.
- •Branches are ‘artificial’; long-term careers often decouple from major
- •Value of IIT: peers, faculty, alumni network, and formative experiences
