Why Krishna Iyer Left Big Tech for a 170-Year-Old Railroad

He spent two decades at the frontier of tech. Then he chose a 177-year-old railroad instead.In this episode, I talk with Krishna Iyer, head of software engineering at BNSF, a Berkshire Hathaway company. Krishna spent years building enterprise software at Microsoft, scaling consumer products at Amazon's Kindle, and working at the edge of generative AI at AWS, before deciding the biggest opportunity wasn't in another tech company. It was in applying AI to a foundational industry the world can't live without: freight rail. We talk about how he thinks about career decisions in decades, not years, why intellectual humility matters more than expertise right now, and what parenting has taught him about growth. This conversation covers executive search themes around fit, timing, and how leaders evaluate the right career move, even when it looks like a detour to everyone else.Key Takeaways:- Why Krishna compares AI's impact to the arrival of electricity - The "power plant vs. transmission lines vs. appliances" framework for thinking about where to build in AI - Why freight rail is one of the most consequential, least understood industries in the country - How to know when it's time to stop iterating and pick a direction - The "2,000 coins" analogy for thinking about time and weekly output - Why "just delegate" is bad leadership advice, and what situational leadership looks like instead - The "heart, tree, star" exercise for understanding what actually motivates someone - How three 90-minute blocks a day can change your output - Why intellectual humility is now a "need to have," not a "nice to have"Connect with Jason: https://www.linkedin.com/in/jasonbaumgarten/ Email the show here: jason@fithappens.fm00:00 Introduction to Fit Happens 00:38 The Fit Happens Thought Experiment 01:30 Krishna's Path From India to Microsoft 03:16 Moving to Amazon and Kindle 04:03 Why AI Is Like Electricity 05:16 Power Plants, Transmission Lines, Appliances 05:50 Choosing BNSF and Berkshire 06:06 What Fit Really Means to Krishna 06:31 What Most People Don't Know About Rail 07:53 Reactions From His Tech World 09:19 What Transfers Across Careers 12:14 The 10,000 Hours Philosophy 13:32 Unlearning Tech Instincts at BNSF 15:41 Failing at the Right Goal 16:22 Advice for Feeling Stuck 18:16 The Oxen in the Field Story 19:39 The Power of Doubling Your List 20:06 Finding Your Best Work Ever 22:35 Helping Your Team Find Flow 24:08 The Heart, Tree, Star Exercise 25:11 Three 90-Minute Windows a Day 26:41 Deep Work and the 13-Minute Reset 29:07 Waking Early for Deep Work 30:18 Peter Drucker on Deadwood 31:12 The 2,000 Coins Analogy 34:15 What Parenting Teaches About Fit 36:10 Speed Round Begins 37:39 Leadership Advice That's Actually Bad 39:05 Balancing Delegation and Depth 40:27 Best Career Advice Krishna Got 42:10 One Piece of Advice for His 25-Year-Old Self 42:41 What Skill Becomes Obsolete With AI 44:09 Closing Thoughts on Freight and Fit