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Best Place To Build

Anand Rajaraman| The IIT Madras founder who sold to Amazon & Walmart; Now owns a cricket team| Ep.12

Meet the tech visionary whose journey spans three decades of innovation. Anand Rajaraman has consistently been ahead of the curve, from revolutionizing online shopping in the 1990s to transforming venture capital with data science today.

Feb 7, 202554mWatch on YouTube ↗

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Chapter summaries

Back on IIT Madras campus: alumni homecoming, Saarang memories, and a quick career snapshot
Anand Rajaraman returns to IIT Madras during Saarang (formerly Mardi Gras) and reflects on the campus energy. He gives a high-level overview of his path: IITM ’93, Stanford, entrepreneurship, and investing—setting up the conversation’s arc.
- •IITM nostalgia: Saarang/Mardi Gras and the feel of campus
- •Anand’s self-introduction: alum, technologist, entrepreneur, investor
- •Teaser of the journey: PhD track → startup → investing → sports team ownership
Stanford PhD research sparks Junglee: data integration meets the early web
Anand explains the Stanford research context—information/data integration across databases—and why the web became the most compelling data source. The team shifts from academic ideas to building structured querying for real-world use cases like product lookups.
- •Information integration/data integration research roots
- •Realization: the web holds the most valuable information
- •Focus on structured queries vs keyword search
- •Early comparison-shopping as a killer application
Founding Junglee and inventing online comparison shopping
The four co-founders (IIT and other Indian institute alumni) form Junglee, with Anand leaving his PhD (officially a leave) to build it. They create a technology stack enabling comparison shopping and begin operating in the capital-intensive pre-cloud era.
- •Founding team: Venky, Ashish, Rakesh, Anand; early roles and context
- •Dropping out/leave of absence from PhD to start up
- •Building a comparison-shopping platform before the category was mainstream
- •Operational reality of the era: buying/hosting servers, overheating, moving to data centers
Amazon acquires Junglee (1998): Bezos’s vision beyond books and the birth of Marketplace
Amazon approaches Junglee soon after Amazon’s IPO, when it primarily sold books and was still small. Post-acquisition, the Junglee team helps build Amazon’s third-party marketplace—now central to Amazon’s business and especially relevant to India’s marketplace-only model.
- •Timeline: Junglee founded 1996, acquired 1998; Amazon post-IPO
- •Bezos’s vision: Amazon as ‘any product’ destination
- •Junglee’s web-integration tech as an enabler
- •Junglee team’s contribution: early Amazon Marketplace/third-party sellers
Why the name ‘Junglee’ stuck: Yahoo! joke, branding story, and investor pushback
Anand recounts the last-minute naming scramble before pitching investors and the playful logic: ‘What comes after Yahoo!? Junglee.’ The Washington Post invests but initially dislikes the name as “not corporate,” yet the founders keep it by challenging them to propose a better alternative.
- •Naming pressure: pitch deck ready but no company name/.com availability
- •Origin: ‘Yahoo!’ precedes ‘Junglee’ (song-inspired)
- •Post-hoc narrative: the internet as a jungle needing a guide
- •Washington Post funding and objections to the non-corporate name
The appeal of ‘zero to one’ and how first-principles thinking drives it
Anand explains why he gravitates to building new things despite risk: it’s the most rewarding path when it works. He connects this to first-principles thinking—questioning hidden assumptions behind how problems are “normally” solved to find non-obvious solutions.
- •Motivation: doing what hasn’t been done before
- •Risk/reward tradeoff and ‘low-hanging fruit’ for pioneers
- •Definition of first principles: surfacing and challenging assumptions
- •Why first-principles thinking often yields unconventional approaches
Taking cricket to America: diaspora critical mass + T20 product-market fit
The conversation shifts to Anand as a sports team owner and his ambition to grow cricket in the US. He argues the timing is right due to a sizable cricket-aware South Asian/Indian-American base and the T20 format aligning with American sports consumption patterns.
- •Personal origin story as a cricket fan (Kapil Dev era)
- •Bringing a beloved sport to his adopted home in the US
- •Market premise: millions in the US already understand/love cricket
- •Format premise: T20 fits a ~3-hour entertainment window better than Tests/ODIs
Major League Cricket explained: teams, IPL affiliations, and the San Francisco Unicorns
Anand breaks down Major League Cricket’s structure, its six city-based teams, and connections to IPL franchises. He shares ownership details for the San Francisco Unicorns and highlights prominent tech leaders involved across teams.
- •Six teams/cities: Seattle, SF, LA, NY, DC, Dallas
- •IPL tie-ups: Texas Super Kings (CSK), MI New York, LA Knight Riders (KKR)
- •Anand & Venky as majority owners of San Francisco Unicorns; other notable owners
- •Early seasons (2023, 2024) and credibility from marquee involvement
Building fandom: star power, ‘Beckham moments,’ and intimate stadium experience
They discuss how leagues gain traction via recognizable talent—coaches and international stars—and compare it to soccer’s US growth via Beckham. Anand notes fans value being physically closer to the action in smaller venues, reinforcing the entertainment product.
- •Need for elite players/coaches to validate the league
- •Pat Cummins positioned as a ‘Beckham-like’ global draw
- •Indian player availability constraints in foreign leagues
- •Fan insight: smaller stadiums create intimacy and higher engagement
From entrepreneur to investor: early Facebook story and the role of luck + networks
Anand recounts how he and Venky noticed Facebook’s campus pull at Stanford before it was widely known. A later connection led them to invest personally in a round led by Accel, illustrating both the importance of observing user behavior and being ready when chance opportunities arise.
- •Spotting Facebook via student attention at a Stanford event/panel
- •Full-circle connection: Washington Post as Zuckerberg’s alternative lead investor
- •Personal (angel) investment rather than through a fund at that moment
- •Lesson: luck matters, but preparedness and pattern-recognition matter too
How venture capital works: funds, portfolios, and expected outcomes
For younger listeners, Anand explains venture capital fundamentals: pooled capital investing in startup equity with the expectation most will fail and a few will return outsized gains. He contrasts entrepreneurship’s single-bet control with VC’s diversified-but-indirect exposure.
- •VC = pooled capital investing in startup equity for exits (IPO/M&A)
- •Portfolio logic: ~20–25 companies; many go to zero
- •Return distribution: a few ‘home runs’ drive most fund performance
- •Entrepreneur vs investor: control vs diversification
Data-driven venture capital at Rocketship: replacing warm intros with machine learning
Anand describes Rocketship’s thesis: use data and ML to systematically identify promising startups rather than relying solely on referrals and networks. They build a global startup-activity database and proactively reach out to companies flagged by models.
- •Traditional VC sourcing via introductions and networks
- •Rocketship approach: build/aggregate a startup activity dataset
- •ML models to surface ‘interesting’ companies earlier or off-network
- •Inverted funnel: the fund approaches founders, not the other way around
Returning to Stanford to finish the PhD and a two-decade teaching journey in data systems
Anand shares how he completed his PhD after Amazon and began teaching at Stanford, initially covering distributed databases and later data mining. Teaching keeps him close to technology, forces clarity of thought, and brings continuous exposure to fresh perspectives.
- •Timeline: leave in 1996, acquisition 1998, Amazon till 2000, PhD finished after returning
- •Teaching origin: filling in during an advisor’s sabbatical
- •Shift to data mining; early days had tiny enrollments before ‘big data’ boom
- •Teaching as learning: students challenge assumptions (ties back to first principles)
Deep-tech investing via academia: Aster Data story and why Cambrian existed
Anand explains how teaching and university ecosystems surface deep-tech startup ideas, exemplified by Aster Data originating from a TA’s insight on new hardware architectures. He connects this to founding Cambrian Ventures to back university-born companies that struggled to raise early funding—like Junglee once did.
- •Aster Data formed from a Stanford TA’s observation about commodity clusters
- •Innovation: blending MapReduce concepts with SQL/relational systems
- •Outcome: acquisition by Teradata
- •Cambrian Ventures mission: seed and mentor university/deep-tech founders early
AI as a standalone discipline: IITM’s BTech AI, ‘AI+X,’ and where CS is headed
The discussion turns to education trends: IIT Madras splitting AI into its own undergraduate program. Anand argues AI is becoming pervasive (‘AI+X’) and may justify separation as CS expands, noting similar conversations at Stanford.
- •AI’s cross-cutting impact: ‘AI plus everything’
- •IITM’s move to create a dedicated AI program
- •Stanford’s AI center and internal debates about restructuring CS
- •AI reaching critical mass to stand as an independent discipline
Decades-long partnership with Venky: from grocery trips to Kosmix and Walmart Labs
Anand narrates how he met Venky at Stanford (not IITM), collaborated under the same advisor, and repeatedly built together—Junglee, Cambrian, and Kosmix. Kosmix’s acquisition by Walmart leads to the creation of Walmart Labs (including Bangalore), aimed at competing with Amazon through tech talent and brand repositioning.
- •Met at Stanford despite both being IITM alumni (5-year gap)
- •Shared advisor and research → repeated founder collaboration
- •Kosmix: ‘AI before it was cool,’ acquired by Walmart (2011)
- •Walmart Labs as a talent/brand strategy; Bangalore office setup
IIT Madras as an opportunity-rich environment: co-founders, mentors, and early ecosystem wins
Anand argues IITM offers the ingredients that increase ‘surface area of luck’: strong peers, mentors, and brand credibility for fundraising. He emphasizes the importance of co-founders and points to Rocketship’s IITM-linked investments like Mindgrove as ecosystem proof.
- •Opportunity-rich environments amplify serendipity and venture outcomes
- •Advice: prioritize finding stress-tested co-founders
- •Mentorship flywheel via alumni engagement
- •IITM startup examples in his orbit: Mindgrove and more
Medibuddy and the IITM Entrepreneurship Fund: seeding a generation of startups
Anand describes mentoring and funding Medibuddy and highlights how IITM’s entrepreneurship program structure created value for both founders and the institute. He recounts a pivotal 2012 ICSR talk, the low show-of-hands moment, and the creation of a seed fund with Silicon Valley alumni that helped back companies like Medibuddy and Hyperverge.
- •Medibuddy growth: major telemedicine/health platform scale and brand presence
- •Equity-for-support model benefitting IITM (stake sale proceeds funding more startups)
- •2012 ICSR talk catalyst and director-level push to encourage entrepreneurship
- •Formation of IITM Entrepreneurship Fund with alumni; early seed checks and portfolio impact
India’s tech inflection: talent + market, and why it’s different from 1993
Anand frames India’s promise along two axes—world-class talent and a massive fast-adopting market—and explains why this wasn’t true in the early 1990s. He uses the shift in IIT graduate migration patterns to show how opportunity has moved decisively toward building in India.
- •Two theses: India as talent engine and as large domestic market
- •Contrast with 1993: smaller market and narrower talent pool
- •Migration flip: earlier most went abroad; now a minority do
- •Counterfactual: if graduating today, he’d likely build in India
Advice for students and parents: branches matter less than networks and problem-solving
Anand advises parents not to over-index on majors like CS, arguing branches are increasingly artificial and outcomes diverge from degrees. He emphasizes IIT’s core value: peer cohort, faculty, alumni network, and the formation of durable relationships that power careers and startups.
- •IIT achievement as entry into a high-caliber peer group
- •Branches as ‘outdated’ labels; real skill is general problem-solving
- •Choose IIT network over non-IIT CS in many cases (network effects)
- •Relationships, all-nighters, and shared challenges build lifelong leverage
Parting message: enjoy college, build bonds, and carry the network forward
In closing, Anand encourages students to savor their IIT years while still aiming high. He returns to the theme of relationships and networks as enduring assets that compound over time.
- •College memories as uniquely valuable (Saarang/Mardi Gras nostalgia)
- •Balance ambition with enjoyment and community
- •Bonding with peers creates future opportunities
- •Appreciation for the podcast and its role for students/prospective students

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