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Best Place To BuildBest 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

S. Anil KumarguestAmruthost
Feb 12, 20261h 28mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Human-centered matchmaking: solving modern dating with trust, service, and AI

  1. Jodi365 evolved from a platform into a fully personalized matchmaking service that handles searching, screening, curation, and sensitive verification for clients.
  2. Anil argues matchmaking is not a scarcity problem but a trust-and-judgment problem made harder by anonymity, misrepresentation, and the paradox of choice in apps.
  3. He positions technology as an enabler—not the product—using tools like matching engines, masked calling, and video verification while emphasizing empathetic human guidance.
  4. Anil views the new wave of LLM-based AI as potentially valuable when used to “clone” high-quality counseling and reflection, but dangerous when used to scale deception or shallow swiping.
  5. His personal journey—from IIT Madras and a long U.S. academic/corporate path to entrepreneurship driven by heartbreak—shapes his focus on agency, readiness, and intentional commitment in relationships.

IDEAS WORTH REMEMBERING

5 ideas

Matchmaking is primarily a trust problem, not a search problem.

There are plenty of singles; the hard part is determining who is genuine, serious, and compatible, without wasting time or exposing yourself to manipulation.

A matchmaker’s value is asking the questions you can’t.

A trusted intermediary can surface sensitive truths (intent, background, finances, life constraints) while reducing awkwardness and preventing miscommunication breakdowns between two people.

Apps amplify the paradox of choice and reduce commitment.

Endless profiles make people delay investment, always hoping the next swipe will be better, which fuels “swiping fatigue” and undermines relationship-building.

Technology should support empathy-heavy service, not replace it.

Anil frames Jodi365 as an app-enabled services company: tech (graph-based matching, secure communications) improves operations, but the “product” is guided human decision-making.

AI is an opportunity when it deepens understanding, a threat when it boosts fakery.

LLMs can help capture counseling-like guidance (a “digital twin”), but in scale-first platforms they also enable better lies—polished bios, altered images, and synthetic personas.

WORDS WORTH SAVING

5 quotes

It’s not a search problem. There are enough singles out there.

— S. Anil Kumar

We are a solutions company, not a technology company.

— S. Anil Kumar

It’s not about just finding the right partner, but being the right person for each other.

— S. Anil Kumar

I see value in cloning myself… enabling a digital twin inside Jodi365.

— S. Anil Kumar

Don’t settle for an affluent life of quiet aspiration.

— S. Anil Kumar

Personalized matchmaking as concierge serviceTrust, intent, and verification in online datingParadox of choice and swiping fatigueAI as digital twin vs. AI-enabled deceptionCompatibility: values, readiness, adaptabilityMarketplace economics and weak network effectsFounder journey: IIT to US to entrepreneurship via pain point

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