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

ℹ️ EPISODE INFO

Released

February 13, 2026

Duration

1h 28m

Channel

Best Place To Build

Watch on YouTube

▶ Open ↗

📝 EPISODE DESCRIPTION

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

🎤 SPEAKERS

• S. Anil Kumar

  guest

• Amrut

  host

🧾 EPISODE SUMMARY

In this episode of Best Place To Build, featuring S. Anil Kumar and Amrut, Valentine's Day Special: Building Human Connections, one pair at a time; S. Anil Kumar, Jodi365 explores human-centered matchmaking: solving modern dating with trust, service, and AI Jodi365 evolved from a platform into a fully personalized matchmaking service that handles searching, screening, curation, and sensitive verification for clients.

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