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A conversation with Rajesh Thiagarajan · Part 1 · ~44 min

Strong opinions, loosely held.

Twenty years of memory lane with a friend who walked into my career with foundations — and what it takes to be a consultant people actually listen to.

23 May 2026Recorded on MeetLong-form · Part 1 of 2

Rajesh and I met in 2018, at a moment in my career when we were building software the way you build a bullock cart — frugally, by force of will, without good product practice or good engineering practice. It worked, in the loosest sense of the word. It did not scale. He walked in with foundations, and a lot of what I am able to do today at Travelopia traces back to the layers we built together over those years. This conversation was long overdue.

The story I wanted him to tell first was from fifth standard. His small school had two factions — the studious Jaymohan group and the mischief Kamalesh group — and a boy who refused to join either. Why can't I start my own? The same streak showed up a decade later, in the first English class of engineering college, when a professor announced he would teach differently and Rajesh — a first-year, in a fairly traditional Indian classroom — put his hand up and asked why he thought any of them would actually change. The professor called him Prophet for the next three years. Part rebel, part rule-follower. He still carries it.

The phrase he keeps coming back to is the one I borrowed for this title — strong opinions, loosely held. It gets thrown around in tech circles to license stubbornness; Rajesh actually means it. He arrives with opinions because every conversation needs a starting point, but he treats the opinion as a way to open the question space, not close it. That is what made Equal Experts the right home for him, and it is what I needed when I called him in. Within the first week, when I showed him an Excel backlog of five hundred items, he said: let's not even look at it. Tell me the biggest problem. Let's start building.

"I didn't join to document your thoughts."

The most quotable moment in the conversation, though, is from earlier — three months into his first real product role at Recruiter Box. He called the two founders, both deep thinkers, both very capable, and told them this isn't going to work. You two go off, think hard, come back with the answers, and then ask me to execute — which means I am not getting the space to own anything. I did not join to document your thoughts. They heard him. The founders separated. One started talking directly to him. The product matured. I think of this story as the consultant's lesson disguised as a job complaint: you have to demand the space to own a problem, or you will spend a career converting other people's thoughts into JIRA tickets.

Toward the end I asked him about something I have observed in him since the Enchanting days — a kind of fearlessness, but not the projected sort. There is a Sanskrit word, abhaya, often loosely translated as fearlessness. The translation is wrong. Fearlessness is the acknowledgement that fear was once present. Abhaya is the absence of fear altogether — a state where the question simply does not arise. He pushed back, gently. He has fears, he said; the day he caught himself thinking what will Ragu think? about a product decision, he made it go away because what mattered was the user, not the founder's opinion of him. So perhaps it isn't abhaya. Perhaps it is the practice of seeing fear and watching it leave. Either way, I have watched it operate.

There is a Part 2 we promised each other — on Infosys, the company that shaped his professional ethics during his first seven years. Worth waiting for. For today, this is enough: the mosaic of a career, and the principles a thoughtful person carries through it.

— SREE

Six-panel comic strip illustrating Rajesh Thiagarajan's career arc: fifth-standard refusal to join either group; leading school prayer; the Prophet professor; late nights at Infosys; strong opinions, loosely held; and not fearlessness, but the absence of fear.
The conversation, told as a strip — six beats from a fifth-standard classroom to the absence of fear.

Chapters

  1. 00:00Cold open — thanks for waking up early
  2. 00:19The prompt: how did the Rajesh of today get built?
  3. 02:58Two groups in 5th standard — and starting a third
  4. 05:38Stepping onto stage, leading prayer, intensity
  5. 06:3911th & 12th — feeling lost in a bigger pond
  6. 07:42Engineering college, and the "Prophet" story
  7. 09:00Part rebel, part rule-follower
  8. 10:29Joining Infosys (1999): ethics, integrity, all-nighters
  9. 11:37Carrying work in his head — for years
  10. 12:48ISB, and the choppy years that followed
  11. 13:50Brio Tribes — first startup, first scars
  12. 15:00Casino machines and insurance fine print
  13. 16:11Recruiter Box — hitting product-market fit
  14. 17:25Back to "Prophet" — what was going on in his head
  15. 20:04Collaboration, dialogue, and holding space for questions
  16. 23:50Meeting Sree at Enchanting — strong opinions, open mind
  17. 27:02Why JK Krishnamurti's "dialogues" are one-sided
  18. 28:08500 backlog items — let's not even look
  19. 30:33How Enchanting & Travelopia scaled from that foundation
  20. 32:53Where the deep product sense came from — Joel Spolsky, 2006
  21. 35:05Recruiter Box: "you two go think — this isn't working"
  22. 38:21Three things he carries forward
  23. 39:42On abhaya — the absence of fear, not fearlessness
  24. 41:50The day he caught himself thinking "what will Ragu think?"
  25. 42:38Closing reflections — fortune, technology, what lies beyond
  26. 44:05Wrap — what we should chat about next
About Rajesh Thiagarajan

Engineer, product thinker, consultant

Rajesh Kumar Thiagarajan is an independent consultant who has spent the last two decades building software products and the teams that ship them. Seven formative years at Infosys, a business degree from the Indian School of Business, two of his own startups, and a long product chapter at Recruiter Box — followed by years at Equal Experts, where his philosophy of "strong opinions, loosely held" found its natural home.

His work today is about helping leaders see their product clearly, ask the right starting questions, and move without flinching once the answer arrives.

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Part 2 — coming soon. The Infosys story: the culture that shaped one of India's most ethical companies, and what Rajesh carried out of his first seven years there.