Software People Stories Loving Failure and Learning Daily with Kumaran Anandan
In this podcast episode, Gayatri Kalyanaraman is in conversation with Kumaran Anandan, CTO of TinyMagiq and Enterprise Architect —shares a refreshingly honest journey across hardware, industrial automation, embedded systems, startups, consulting, and Microsoft. From writing programs on a programmable calculator (and storing them in audio cassettes!) to building deep learning habits through daily compounding, Kumaran explains why modern technologists must fall in love with failure, understand fundamentals, and stop building software without users who will pay. A thought-provoking conversation on architecture, human psychology, AI hallucinations, and what it really means to create value.
00:00 – 01:00 — Kumaran’s self-introduction: experimenting constantly and looking forward to failures.
01:00 – 02:25 — Earliest career memory: building a DBase 3+ application for a school and earning a watch as his first “payment.”
02:26 – 03:29 — Not getting campus placed, being an average student, and the early struggle of finding a job.
03:29 – 05:20 — First software experience in 10th holidays: programmable Casio calculator, BASIC programming, and saving programs using an audio cassette tape.
05:20 – 07:56 — Early career direction: interest in hardware, industrial automation, 8085 assembly programming, and learning through real-world constraints.
07:56 – 10:12 — Moving up the stack: C/C++, antivirus software, Wipro’s hardware + software work, and “mobile apps” before mobile became mainstream.
10:12 – 11:34 — Entrepreneurship journey: starting a company during the internet boom, shutting it down after the bubble burst, then transitioning to Microsoft.
11:36 – 12:29 — Kumaran’s definition of good technology: anything that protects evenings and weekends from work.
12:31 – 13:48 — A conscious career decision: taking a salary cut to work on hardware because learning mattered more than comfort.
13:48 – 15:39 — Microsoft Consulting Services: being called only for complex “fires,” shorter engagements, and high learning intensity.
15:39 – 17:23 — The daily learning habit: “Kumaran of yesterday won’t be Kumaran today,” and how small learning compounds over time.
17:24 – 19:28 — Curiosity beyond the surface: learning “under the hood,” connecting ideas across psychology, neuroscience, and technology.
19:42 – 23:16 — Microsoft culture: self-learning, asking better questions, getting pointers instead of hand-holding, and building independent thinking.
23:39 – 26:10 — Fundamentals matter: software is predictable (input–process–output), hardware is ambiguous, and AI changes predictability in software.
26:36 – 29:21 — TinyMagiq and mentoring: serendipity, a clear timeline to quit corporate life, and why enterprise software rarely creates joy.
30:39 – 33:35 — A common founder mistake: building for 14–18 months with no paying users and confusing “features built” with “value delivered.”
33:35 – 36:46 — Pricing reality check: if nobody pays even ₹100, the problem isn’t the market—it’s unclear value and weak conviction.
36:46 – 38:35 — “I don’t like code”: code as debt, and why architecture must fight unnecessary complexity.
38:35 – 41:19 — Loving failure: video games as a metaphor, why software needs failure-tolerance, and a warning to those who want “safe IT careers.”
41:56 – 44:01 — Entrepreneurship mindset: de-addiction to monthly salary, India’s services legacy, and why playing safe kills learning.
44:01 – 46:40 — “Unlearning” is reframing: the hardest failure is success because it reinforces old patterns and makes change difficult.
48:11 – 51:27 — AI hallucinations and “Maya”: why we’re already trained to handle uncertainty, and how that applies to building AI systems.
51:27 – 52:08 — Architecture simplified: an architect ensures user happiness through people, process, and technology.
52:44 – 53:06 — Closing advice: be curious about how you can enjoy failure.
Quotable Quotes
“A person who keeps experimenting… and looks forward to failures.”
“Kumaran of yesterday will not be the Kumaran who goes to sleep today.”
“The power of compounding becomes very high.”
“If you don’t have a user who wants to pay for it… what is the value of your product?”
“Even if you can’t get somebody to pay you hundred rupees… you have not delivered that value.”
“To me, a lot of code is nothing but debt.”
“People should fall in love with failure.”
“An architect is somebody who ensures happiness of the user.”
“Be curious about how you can enjoy failure.”
Kumaran Profile:
Technology professional with 20+ years experience (Unix, Windows, Cloud AI)
Conducts two podcast series: "Saturday Architecture" and "Mindset Matters"
Experience spans from hands-on development to business architecture
Known for: Connecting technical and philosophical concepts
Key Philosophies:
"If you don't have pain, you haven't done anything"
Long-term thinking reveals patterns short-term goals miss
Age brings pattern recognition advantage despite reduced raw capacity
Common sense is the most uncommon thing
Kumaran can be contacted at https://www.linkedin.com/in/akumaran/
@ctomentor is Kumaran’s twitter handle