Michael Dell, Founder of Dell — Early Failures, Battling Carl Icahn, Learning from the Competition, and How to Play Nice But Win (#534)

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“You learn a lot more from your customers than you do from the competition.”

— Michael Dell

Michael Dell (@MichaelDell) is chairman and chief executive officer of Dell Technologies, an innovator and technology leader providing the essential infrastructure for organizations to build their digital future, transform IT, and protect their most important information. He is the author of Play Nice But Win: A CEO’s Journey from Founder to Leader.

Michael is an honorary member of the Foundation Board of the World Economic Forum and is an executive committee member of the International Business Council. In 1999, he and his wife, Susan Dell, established the Michael & Susan Dell Foundation.

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The transcript of this episode can be found here. Transcripts of all episodes can be found here.

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What was your favorite quote or lesson from this episode? Please let me know in the comments.


Want to hear another episode with an innovator who understands the value of failure? Listen in on my conversation with Sir James Dyson in which we discuss what it means to think like an engineer, how many tries it took to get a working prototype of his famous Dyson vacuum, the trials and tribulations of funding research and development, why invention is more about persistence than brilliance, experience as baggage that can get in the way, and much more.


  • Connect with Michael Dell:

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  • How does meatloaf figure prominently in the story of Michael’s life? [05:28]
  • Who is Carl Icahn? [06:57]
  • Where did the title Play Nice But Win originate? [07:53]
  • Does playing nice make it harder to negotiate or compete against people who don’t live by such a code? [09:02]
  • How did Michael make $18,000 selling newspaper subscriptions at age 17? What tactics did he employ to gain an edge that wouldn’t normally occur to most 17-year-olds? [10:26]
  • During this time, were there any entrepreneurial heroes Michael looked up to? [15:07]
  • Michael wrote his first book, Direct From Dell, in 1998. What does he feel more comfortable discussing now that he may have hesitated to share back then? [16:16]
  • Memorable mistakes and failures — how Michael felt about them in the moment, and how they drove him to adapt. [18:03]
  • Is the ability to be more vulnerable something that comes with age? [21:54]
  • What considerations are especially stressful for a CEO of Michael’s stature when things don’t go according to plan, and what has gotten him through the particularly tough times? [23:15]
  • As an introvert, how does Michael navigate his high-profile vocation? [26:23]
  • In retrospect, would Michael have handled his company’s unsustainable early hypergrowth differently? [28:05]
  • Michael explains what happened when Dell walked back from being publically traded to privately held — and then public once again. [29:49]
  • What is a tracking stock? [34:16]
  • What were the risks of going private, and how did Michael think about mitigating them? [37:28]
  • How was the decision to go public again made? [39:12]
  • Who was particularly helpful during the take private chapter of this experience? [41:02]
  • The most worthwhile investments Michael has made. [42:05]
  • How does Michael think about competition while remaining true to his Play Nice But Win ethos? [43:51]
  • What are some common mistakes Michael sees when companies engage in a direct-to-consumer business model? [45:47]
  • As busy as Michael already is, why did he dedicate the time and energy to write Play Nice But Win? What does he hope the reader will take away from it? [50:10]
  • Parting thoughts. [52:17]


“Failure is a key ingredient in any success.”
— Michael Dell

“You learn a lot more from your customers than you do from the competition.”
— Michael Dell

“I believe fundamentally that organizations like ours and others will be successful if they solve the future problems that customers have. If they don’t, they’ll just go out of business.”
— Michael Dell

“I have this belief that a lot of human potential is left unrealized because people are afraid to fail.”
— Michael Dell


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