

143. The Habit that Cost $100MM to Learn and Why It Was Worth It (Part 1) - Keith Cunningham
Jun 11, 2018
Keith Cunningham, business expert who lost $100MM and built habits to make it back, discusses the ONE habit at the heart of his success, the dangers of making decisions based on emotions, and the three questions that can change everything in your business. He also shares his experiences meeting Mr. Milken, the five core disciplines for mitigating risks, and the importance of staying engaged in your business. Lastly, he emphasizes the power of clarity, accountability, and honest feedback, promoting his book 'The Road Less Stupid' and an opportunity to win a free signed copy.
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Milken's Scheduled Thinking Time
- Keith Cunningham met Mike Milken in a 1980s cable TV financing meeting lasting about 1.5 hours.
- Milken scheduled specific early morning thinking time, which sparked Keith's lifelong habit of purposeful thinking.
Losing $100M as Tuition
- Keith lost $100 million due to not using his intellectual tools and letting emotions drive business decisions.
- He views the loss as tuition for a life course, making him $100 million smarter.
Ask 3 Key Risk Questions
- Always check assumptions and ask hard questions to mitigate risk in decisions.
- Ask three key questions: what's the upside, what's the downside, and can I live with the downside?