Best Place To Build

Valentine's Day Special: Building Human Connections, one pair at a time; S. Anil Kumar, Jodi365

In today’s episode of the Best Place to Build Podcast, we continue the theme of the last few episodes - Builders who are building something unconventional. Today’s guest on the podcast is building human connections through a personalised matchmaking service. Yes, you read it right. Anil Kumar is the founder of Jodi365, a matchmaking service that he has built over 15+ years. Anil is an IIT Madras alumnus whose journey spans a PhD, marine consulting in the US, an MBA from Booth, and eventually a deeply personal realisation: professional success does not automatically translate to personal fulfilment. Join Amrut as he speaks to Anil about not just dating, culture, technology, ambition, heartbreak, and building solutions rooted in lived experience. Of course, AI finds it place in this conversation as well as our guest talks about its role in building matches. In this episode: Why matchmaking is still an unsolved problem How technology changed relationships - for better and worse Swiping fatigue, paradox of choice, and authenticity in an AI era Why being the right partner matters more than finding the right one How Anil is blending human intuition with AI to scale personalized matchmaking If you’re interested in how technology intersects with culture, psychology, and long-term decision-making, this conversation is worth your time. Also, this conversation broke the record of our longest-ever podcast episode! Chapters: [00:01:16] Intro [00:01:51] How does Anil Kumar describe what Jodi365 is? [00:07:52] Why is matchmaking a problem to be solved? [00:22:53] His personal journey from IIT to the US [00:27:05] How a personal pain point led to an entrepreneurial insight? [00:38:52] What is broken in dating apps and how can technology fix it? [00:47:10] Anil’s definition of compatibility [00:55:28] Is introducing AI in matchmaking a threat or opportunity [01:13:40] Anil’s advice to young people navigating relationships [01:25:45] Closing reflections from Anil #Matchmaking #ModernRelationships #AIAndRelationships #SwipeCulture #FounderJourney #Jodi365 #HumanConnection #BestPlacetoBuild #IITMadras

SKS. Anil KumarguestAMAmruthost

Feb 13, 2026·1h 28m·Watch on YouTube ↗

📖 CHAPTERS

1. 1

   Podcast setup at IIT Madras + meet S. Anil Kumar (Jodi365)

   Host Amrut introduces the show’s premise—meeting builders at IIT Madras—and brings on alumnus S. Anil Kumar. Anil frames himself not as a “startup founder” anymore, but as someone running a durable, growing business in matchmaking.

2. 2

   What Jodi365 actually does: high-touch matchmaking as a concierge service

   Anil explains Jodi365 as an app-enabled, fully personalized matchmaking service that does the searching, screening, and curation for clients. He emphasizes meeting people where they are on the “readiness spectrum,” from marriage-ready to wanting to start as friends.

3. 3

   Why matchmaking is still a hard problem: trust, intent, and social friction

   The core challenge isn’t finding singles—it’s identifying who is genuine, aligned, and serious. Anil describes how modern life reduces community-led introductions and increases ambiguity, awkwardness, and safety risks, making a trusted intermediary more valuable.

4. 4

   Technology as an enabler (not the solution): from automobiles to “online watering holes”

   Anil reframes “tech disruption” as a long continuum: cars expanded partner search radius, phones enabled distance, and apps widened access further. But online spaces also become “watering holes” with predators and noise, requiring guardrails and better filtering.

5. 5

   What’s broken in dating apps: paradox of choice, swiping fatigue, and shallow profiles

   Anil argues many apps train people to judge via two-dimensional profiles, amplifying choice overload and reducing commitment. He challenges the “soulmate” narrative, emphasizing that relationship success also depends on becoming the right people for each other.

6. 6

   Under the hood at Jodi365: matching engine + human-centered service

   While Jodi365 runs robust technology (including a graph-database matching engine), Anil insists the company is a solutions/services business rather than a pure tech company. The differentiator is the human work—context, judgment, counseling-like guidance, and careful introductions.

7. 7

   AI in matchmaking: opportunity (digital twin) vs threat (deception at scale)

   Anil describes a ‘second wave’ of AI enabled by LLMs: useful when it deepens understanding, coaching, and reflection—like “cloning” the best parts of a seasoned matchmaker. He also warns AI can worsen fraud and misrepresentation on scale-first platforms.

8. 8

   Building trust features early: privacy, verification, and safety guardrails

   Anil shares concrete product choices aimed at safety and authenticity—masked calling, video-based verification, and processes designed to reduce catfishing and misinformation. He draws parallels to hiring: written applications are less trustworthy in the age of AI-generated content.

9. 9

   From Chennai to IITM: early life, family story, and finding his path

   Anil recounts growing up in Chennai in a multicultural family, navigating expectations of engineering/medicine, and discovering IIT Madras as a dream campus. He describes early academic struggles, perseverance through a second JEE attempt, and entering Naval Architecture almost by accident.

10. 10

    US journey: MS/PhD, consulting career, and the restlessness to build something larger

    Anil details specializing in computational ship hydrodynamics, research funding realities, and later marine consulting work. Despite success, he felt his ambitions exceeded the narrow domain and began seeking broader impact—eventually via business and entrepreneurship.

11. 11

    Personal pain point → entrepreneurial insight: heartbreak, time scarcity, and India’s cultural realities

    Anil connects repeated relationship setbacks, visa/green-card constraints, and modern professional busyness to the need for a better matchmaking model. He positions Jodi365 as a culturally aware hybrid—more intentional than dating apps, less rigid than traditional matrimony.

12. 12

    Why the business is hard: weak network effects, churn, CAC, and ‘glorified databases’

    Anil critiques mainstream matrimonial products as databases and explains why matchmaking economics are brutal: users churn quickly whether they succeed or fail, and marketing spend stays high because supply must constantly be replenished. He emphasizes focus (a clear beachhead) and aligning the service with real outcomes.

13. 13

    Compatibility and assessment: personality models, horoscopes, and what the market actually values

    Anil shares attempts to formalize compatibility—integrating Big Five (OCEAN) personality inventories and exploring horoscope-based approaches—then learning what users in India did and didn’t adopt. The broader lesson: frameworks help, but real matchmaking must respect context and human nuance.

14. 14

    Family influence + brother’s national recognition: struggle, trust, and responsibility

    Anil reflects on family dynamics, sibling influence, and the role of parental trust in shaping character. He discusses his brother’s national award as recognition of goodness and craft, and connects upbringing to resilience and accountability.

15. 15

    Closing advice: career choices, learning mindset, and ‘don’t settle for quiet affluence’

    In final reflections, Anil offers guidance on choosing fields with growth potential, striving to excel, and using today’s information access to make better decisions. He ends with a motivating refrain from business school: build, add value, and avoid a comfortable life of muted ambition.