The 5 Best (and Worst) Tech Execs of All Time


Analyst, Software Advice

Running a major tech company has to be one of the harder callings in the world of business. Not only do you have to be an extremely innovative individual, but you also need the innate ability to be a leader and extract the most out of your employees. Below is a list of the standout winners and losers of the various tech executives in history. Some were endlessly successful innovators, and others could never quite rally the troops enough to get the job done.

The Winners

1. Bill Gates of Microsoft (1978 – 2006)
Dropping out of Harvard doesn’t necessarily make you a failure. The obvious poster boy for life after dropping out is Bill Gates, who left Harvard to follow his passion for his fledgling startup, Microsoft. He and his friend Paul Allen played a huge roll in the desktop computer revolution of the 1980s and 90s. Gates revolutionized personal computing by offering an operating system that could be used on computers from different manufacturers, and by expanding Microsoft’s product offering into the Office suite many of us rely on today. Not only did he grow his company to a 94% market share, and subsequently swallow competition, he guided his company through an antitrust case in the late 90s on his way to becoming one of the greatest executives in history and one of the wealthiest men in the world.

Market Cap

  • Start – $700 million (when first traded in 1986)
  • During – $600 billion (on January 1, 2000, when he stepped down as CEO)
  • Currently – $253 billion

2. Steve Jobs of Apple (1996 – 2011)
There may be no more admired executive than the late Steve Jobs–also a college dropout. While he was known to be difficult to work for, he was respected and loved by those who worked for him. Though not an engineer, he is widely known for introducing many of our most beloved tech gadgets including the Mac, the iPod, the iPhone and the iPad. His relentless drive for product perfection resulted in aesthetic beauty in devices so intuitive that anyone can use them, young to old. Under his leadership (the second time around), Apple enjoyed the second most remarkable gain in value of any company in history.

Market Cap

  • Start: $3 billion
  • During: $376 billion
  • Currently: $460 billion

3. Mark Zuckerberg of Facebook (2004 – present)
Third place features yet another college dropout, but this one had a couple of role models to follow. What started as a dorm room operation with a zero-dollar bankroll has since exploded into an $80-100 billion company that is expected to have its IPO any day. Not a bad return for eight years of work. What is most impressive is the fact that Facebook is not a traditional product-driven company like the others on this list; therefore, Zuckerberg is noted as one of the greatest executives of all time because he has created this massive market cap with a very untraditional product.

Market Cap

  • Start: Raised $2.8 Billion
  • IPO Valuation: $80 -100 billion
  • After: TBD

4. Mark Hurd of Hewlett-Packard (2005 – 2010)
While he did graduate from college, Mark Hurd didn’t invent anything or start a company; he is a manager who worked his way up through the ranks of Corporate America. In 2005, he took the reigns at HP, a large company with a troublesome board, legacy products and a rich history of internal strife, and turned it around in less than two years. In fact, during his five-year reign as CEO, Hewlett-Packard was a world-class performer. Not only did HP stock gain $50 billion under his leadership, Hurd led HP to an impressive six-percent increase in sales (as reported in CNN Money) during the Great Recession of 2008. HP stock gave back that $50 billion within a year of his departure.

Market Cap

  • Start: $57.01 billion
  • During: $107.48 billion
  • After: $51.18 billion

5. Eric Schmidt of Google (August 2001-January 2011)
Google. Enough said. No, but seriously, you can’t create a list of successful tech figures like Steve Jobs and Mark Zuckerberg without the mention of the all-powerful Google and its three-headed Hydra of Larry Page, Sergey Brin and Eric Schmidt. After raising just $1 million from family, friends and other investors, Page and his partner officially launched Google in 1998, and ever since it has been an impressive chain of product launches and acquisitions that has helped transform Google into a verb spoken by people around the world. Between buying YouTube in 2006 for $1.65 billion in stock and Google’s employee-friendly super campus work environment, Page has not only built up a baffling market cap of $208.55 billion, but has created a culture that has become a household noun-turned-verb that we could never imagine a life without.

Market Cap

  • Start: $1 million
  • During: $208.55 billion
  • After: TBD

The Losers

1. Steve Ballmer of Microsoft (January 1, 2000 – present)
Now that we’ve witnessed the winning side of tech execs, Steve Ballmer has to be tops of the The Biggest Loser within the industry. When Steve Ballmer took over as CEO of Microsoft on January 1, 2000, the market cap of the mega computer monopoly was just over $600 billion dollars. Within months, that number plummeted by $350 billion, among the worst declines of any company in history. You can hardly blame Ballmer for the dotcom bubble bursting, but in the last 12 years he has failed to capture any momentum. The current value of Microsoft is almost exactly the same as it was after the crash, and over the last four years half of Apple’s gains seem to match Microsoft’s losses. Critics attribute the $150 billion dip in the last five years to Ballmer’s winning personality, collaborative approach and vision for the company–not.

Market Cap

  • Start: $600 billion
  • During: $237.43 billion
  • After: TBD

2. Leo Apotheker of Hewlett-Packard (2010 – 2011)
The motto of many lean startups is, “if you are going to fail, fail quickly.” This is less of a virtue when you run a company worth over $100 billion and failing means destroying half that value. When Leo Apotheker took over as Hewlett-Packard’s CEO, the move ushered in a reversal of HP’s typically positive numbers. Cutting the market cap nearly in half during his 10-month tenure, Apotheker’s failure can be attributed to the fact that he tried to turn HP from a consumer products company into an enterprise computer services company that could go head to head with Oracle and IBM. He quickly destroyed the Palm hardware unit and planned to sell off the computer division so he could focus on fighting his personal battles with Oracle and IBM. Cutting the value of your company in half in less than a year is a definite fail.

Market Cap

  • Start: $107.48 billion
  • During: $87.36 billion
  • Currently: $57.00 billion

3. Jonathan Schwartz of SUN Microsystems (2006 – 2010)
As the CEO of SUN Microsystems, Schwartz somehow managed to take a company on the climb and launch it into a disaster in free-fall. Under his watch, SUN experienced a string of failures, including losing its main computer server market to HP and an unsuccessful attempt to monetize the Java development environment–a blow that caused the company’s shares (and market cap) to plummet and thousands of employees to lose their jobs.

Market Cap

  • Start: $16.77 billion
  • During: $8.18 billion
  • After: $3.86 billion

4. John Sculley of Apple (1983 – 1993)
Don’t let the numbers fool you. Despite the fact that John Sculley was able to increase Apple’s sales 10X from $800 million/year to $8 billion/year during his decade in charge, many still consider him one of the worst American CEOs of all time. Not only did he force out Steve Jobs, he squandered a 10-year lead Apple had on the competition. It wasn’t until Windows came out in 1993 that the PC industry have anything remotely competitive with the Macintosh OS. Sculley thought marketing was everything and tried to battle head to head with IBM by selling computers aimed at the enterprise, turning Apple from an innovative, product-oriented company to a manufacturer of generic beige boxes. A prime example of his leadership is when he gave each Apple employee a copy of his own book, at Apple's expense, in the hope of inspiring "excellence." Presumptuous much?

Market Cap

  • Start: $2.4 Billion
  • During: $4 Billion

5. Gary Forsee of Sprint Nextel (2005 – 2007)
Last but not least on the list of “tech executive failures” is a man that didn’t necessarily have the big shoes of a former success story to fill, but rather, Gary Forsee managed to underperform all on his own. While the numbers are not all bad during his stint as CEO of Sprint Nextel, Forsee’s attempt to merge with Sprint coupled with driving away millions of subscribers and his $5 billion investment in a failed WiMax network proved to be catastrophic miscalculations that have kept Sprint a distant #3 in the U.S. wireless market.

Market Cap

  • Start: $23.35 billion
  • During: $70.26 billion
  • After: $49.73 billion

We hope you’ve enjoyed this list of successful tech executives and the peak at the others that weren’t so successful. Above all, we hope you’ve learned a thing or two and that you’ll only follow in the footsteps of the first five!

The thumbnail image for this post was pulled from Microsoft.

  • JoAnn

    As a Leadership consultant and coach, I wonder what leadership competencies the “winners” had that the “losers” did not have or at least leverage.  Also who did these leaders surround themselves with? And did they listen?  If nothing else what these comparisons tells us is that extremely smart people do not always make the best leaders, right?   

  • Blogs by Market:
  • Subscribe to the Software Advice Enterprise Blog

Popular Blog Posts