In the years since he returned in 2007 to re-take the reins at Dell Inc, the company has bled market share to the likes of Hewlett-Packard and Lenovo and is now fighting to stem a steep decline in PC sales.
"Michael Dell is once again hungry. Thirty years ago, we think he hungered for success and wealth. In 2013, we think he hungers to restore his legacy and personal balance sheet," said Cindy Shaw, a managing director and research analyst at investment advisory firm Discern Inc.
Dell was upheld as a model of innovation as recently as the early 2000s, pioneering online ordering of custom-configured PCs and working closely with Asian component suppliers and manufacturers to assure rock-bottom production costs.
But as of 2012's fourth quarter, Dell's share of the global PC market had slipped to just above 10% from 12.5% a year earlier as its shipments dived 20%, according to research house IDC.
That the company will go private is not necessarily a new idea; Michael Dell told an investor conference in June 2010 he had considered it before.
But by pulling the trigger now, the 47-year-old billionaire can focus on reversing its fortunes by concentrating on higher-margin corporate IT and services - borrowing a page from IBM (IBM.N). He will do so free from the distractions of running a publicly traded company.
That's still no small task for a company that built its name on customized computers but whose star has waned, and now wants to go up against larger rivals like HP and IBM.
Dell, who has quietly built a highly successful investment firm even as the fortunes of his namesake company have waned, is upping the ante. He will put up more of his own money, contributing his 16% share of Dell's equity to the deal along with cash from his private investment firm MSD Capital. Dell buyout highlights PC sector woes: analysts
"This is an opportunity for Michael Dell to be a little more flexible managing the company. That doesn't take away from the fact they will have challenges in the PC market like they did before," said FBN Securities analyst Shebly Seyrafi.
Dude, where's my Dell?
Michael Dell started the company in 1984 out of his college dorm room with $1,000, and led it to the top of the PC industry.
The TV advertising slogan "Dude, you're getting a Dell" become one of the best-known catch-phrases of the early 2000s.
The company's early successes made him wealthy enough to start MSD Capital, which employs 80 people in three cities who invest his money in everything from stocks to real estate.
Dell chairman and CEO Michael Dell delivers a keynote at the Moscone Center in San Francisco during the Oracle OpenWorld 2011. AFP files
Forbes ranks him among the world's 50 richest, with an estimated fortune of nearly $16 billion.
But much of his success is still tied to the company he founded, and from which he has not been able to step away.
The first time he handed over the reins was in 2004, when long-time lieutenant Kevin Rollins took over as CEO.
The company was on top of its game when Rollins stepped in, but sales and customer service slipped in the ensuing three years, and there was a general sense of relief among investors when Dell reasserted control in January 2007.
"There's been no turnaround and the bottom line is Michael was the one who built the company," Needham & Co analyst Charles Wolf said at the time.
In the six years since Michael Dell resumed leadership, the company's market share has dipped even further, as has its stock.
From the start of fiscal 2007 to fiscal 2012, a $100 investment in Dell stock would have shrunk to just $75, including reinvestment of all dividends. That compared with $127 for the S&P500 IT index.
Dell, which derives more than half its revenue from sales of plain-vanilla PCs and servers, is struggling along with the rest of the industry with declining personal computer demand.
Even with the price surge since rumors of a buyout first broke, Dell shares are still down by roughly half from when he regained leadership. Though, to be sure, HP's stock has also fallen about as much.
During that time the market changed dramatically, and Dell's once-iconic built-to-order PCs have lost favor as consumers and even businesses move toward tablets and smartphones, a market where Dell has taken tentative and unsuccessful steps.
That slide was magnified by Michael Dell's brash confidence, which sometimes got him in trouble with peers, most famously Apple's Jobs.
When Jobs returned to lead the company he started in 1997, Dell famously suggested the co-founder would be better off shutting the company and returning the cash to shareholders.
Nine years later, Jobs had the last laugh when Apple's market capitalization surpassed Dell's. Even given its recent share price slide, Apple remains more than 20 times bigger than the former PC industry darling.
With Dell now choosing to go private, much will hinge on the willingness of future partners to support his potentially costly turnaround effort. Some support has already been received via a $2 billion loan from Microsoft to help fund the deal.
"This gives him flexibility. The market wasn't valuing the company at where he thinks it should be worth and who knows that better than him," said Phil Silverman, managing partner at Kingsview Capital.