How to Make High-Stakes Decisions with Only 10% Information ft. Hiten Shah
Today I'm talking to Hiten Shah, serial entrepreneur and co-founder of Crazy Egg, KISSmetrics, and Nira — which he sold to Dropbox. Hiten has been building SaaS companies for over 20 years and has quietly become one of the sharpest operators and thinkers in tech.We go deep on metacognition, self-improvement, and what it actually takes to understand yourself well enough to build great companies and great relationships. Hiten opens up about his process for "poking at the world" to test his own thinking, how he uses Enneagram and Human Design with AI to unlock blind spots, and the mental models that have shaped how he works with co-founders, teams, and his own family.
We cover
- His "purple bruise" approach to giving advice — and how he trained himself to go from six-month-delayed feedback to next-day impact
- The Batman and Robin framework for co-founder relationships, partnerships, and even marriage
- Why building faster with AI doesn't mean learning faster — and the companies that have figured out the difference
- "Trust takes ten years" — the advice from a relative in India that keeps proving itself right
His life philosophy: "It was all a dream" — and what that has to do with presence
- SO much more!
Timestamps
00:00 Intro
01:45 Start Your Year in October
06:15 The Purple Bruise Method
12:23 AI as a Thinking Partner
20:13 Thinking About Your Thinking
25:06 Find Your Triggers First
29:32 Decide Fast With Less
34:50 Entrepreneur Since Age Four
42:17 Shed Judgment, Stay Curious
46:09 When Strengths Become Sabotage
49:56 Batman and Robin Partnerships
52:43 Finding the Right Co-Founder
59:53 Trust Takes Ten Years
1:05:04 Fast Success Hides Lessons
1:11:57 Build Faster ≠ Learn Faster
1:21:31 The Lost Craft of Startups
1:29:38 Follow Energy, Not Goals
1:36:05 The Crisis Nobody Sees
1:44:03 Selling at Peak Value
1:52:00 Know Yourself Through AI
2:07:15 One Idea, Many Posts
2:19:20 "It Was All a Dream"
Links
Hiten Shah
X: https://x.com/hnshah
LinkedIn: https://www.linkedin.com/in/hnshah/
Luba Yudasina
Instagram: https://instagram.com/lifeoflubaa
X: https://x.com/LubaYudasina
LinkedIn: https://linkedin.com/in/yudasinal Receive SMS online on sms24.me
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