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They Say He’s Nice. The Truth Is He’s Shrewd.
Methods of Prosperity newsletter no. 117: Michael Dell
Sean Allen Fenn
September 11, 2025
Ideas are a commodity. Execution of them is not.”
Most entrepreneurs who go public stay public.
Michael Dell orchestrated something unprecedented in the tech industry.
In 2013, he took his company private.
It was the largest technology leveraged buyout ever ($24.9 billion).
This gave him the freedom to make long-term strategic decisions.
This kind of freedom came without quarterly earnings pressure.
Which is a luxury most public company CEOs don't have.
Most entrepreneurs avoid excessive debt.
Dell embraced it.
He piled on an astronomical $70 billion in leverage to acquire EMC Corporation for $67 billion in 2016.
This contrarian approach turned into “the biggest buyout coup of all time.”
What made it possible?
Cheap money and Dell’s cash-generating business.
Michael Dell is founder of Dell Technologies.
He was born February 23, 1965 in Houston, Texas. Dell demonstrated an early interest in business and technology. He invested in stocks and precious metals as a teenager. He taught himself about electronics. He earned significant income selling newspaper subscriptions and computer upgrade kits. He attended the University of Texas as a pre-med student. Then he dropped out at age 19 to pursue his computer business full-time.
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In 1984, Dell started his company from his dorm room with $1,000.
He named it PCs Limited. He started the direct-to-consumer business model for computers. Which disrupted the traditional retail model.
This was at a time when computer manufacturers sold through retailers and dealers.
This wasn't only cost-cutting.
It was a fundamental reimagining of how technology businesses could operate,
This move gave him direct customer relationships, eliminating middleman costs.
Many tech entrepreneurs build companies only to sell them for a profitable exit.
Dell has remained at the helm of his company for over 40 years.
Forbes called him “technology's last man standing, the final original founder of the computer era still running his baby.”
As KKR's billionaire co-founder George Roberts noted: “Michael is financially sophisticated. He's not a technology geek by any stretch of the imagination... He bought the company back at the right time.”
Dell approaches business with a different mindset.
He’s not only a tech visionary.
He’s a financial engineer.
The result?
Dell's net worth has grown to approximately $50 billion.
He now owns 52% of Dell Technologies plus a 42% stake in VMware.
This is a level of control and wealth that few entrepreneurs achieve.
Such unconventional methods can lead to extraordinary financial freedom.
Dell’s contrarian approach proves it.
He also happens to be a very nice guy. That’s his reputation anyway. Which is rare for a billionaire. His story is counter-evidence to the phrase: Nice guys finish last.
Michael Dell might be nice, but he’s also a shrewd business man.
“As you start your journey, the first thing you should do is throw away that store-bought map and begin to draw your own.”
I like you,
– Sean Allen Fenn
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