Top 10 strangest characters in IT

The day before we do a top 10 list Shaun and I have lunch in a local diner and go over ideas for something timely but interesting.

Last week the big news was Michael Jackson so we did the thrilling list, but after we finished lunch, someone (in the interests of collective responsibility) made a comment about another Michael Jackson list we could have done – the strangest people in IT.

Jackson may have been keen on the title King of Pop but his life can hardly be considered normal. But let he who is without sin cast the first stone. Techies are by nature a little different from the rest of the population.

Some of the people on this list are successful billionaires, Some Nobel prize winners or high-tech nomads. However, some individuals are weird even by geek standards. Those who made this week's top 10 list have managed to not only be hugely successful in the business, but also generate some great stories of oddball behaviour.

Honourable mention: Thomas Dolby

Shaun Nichols: Not too many tech executives can also lay claim to a hit song and landmark video.

Most people know Thomas Dolby only as the man behind the early 80s new wave hit "She Blinded Me With Science." When not creating or producing fodder for MTV, however, Dolby has in fact been a very influential character.

In 1993, Dolby started a small digital music outfit called Headspace. As the web took off, the company developed the RMF music format and the Beatnik browser plug-in. The company now known as Beatnik Inc. is an established developer of music software for PCs and mobile phones.

Dolby has proven to be both a musical and technological visionary. Certainly an odd, if not wonderful combination.

Iain Thomson: I'll give you this one Shaun, but not for the horr ifyingly bad "She Blinded Me With Science."

I've a soft spot for Mr Dolby because he did a lot of good work on Def Leppard's seminal 1983 album Pyromania, under the name Booker T. Boffin. He did get sued by Ray Dolby, inventor of Dolby noise reduction and co-inventor of the video tape, who coincidentally has a son called Thomas.

I can't help thinking that the internet needs more rock stars, especially those who care enough about music to create their own format.

Honourable mention: Steve Ballmer

Iain Thomson: I can't decide if Ballmer's genuinely weird or it's all just an Uncle Fester impression, put on to freak people out.

His conference exhortations have gained him an amused following and there were moves at the UK launch of Windows XP to get the crowd chanting “Do the dance monkeyboy!” but sadly people chickened out.

There have been reports that the wild Man of Microsoft dismembers office furniture in fits of temper and he is apparently a very tough man to face over a board room negotiation. This is what makes me think that he's acting up – when he starts to sweat and get bulgy eyed there's still plenty of people who aren't willing to take the risk that he won't vault over the table and sink his teeth into their throats.

Shaun Nichols: One can never accuse Steve Ballmer of lacking passion. From the aforementioned "Monkeyboy" dance to the enraged "developers developers developers" mantra, Ballmer has given us some classic YouTube clips.

When you get down to it, however, there are few people I would rather have running a large tech firm than Ballmer. He may seem a bit like Uncle Fester on a three day speed binge, but he also runs a pretty tight and well-oiled ship at Microsoft. It is said that Windows Vista was Bill Gates baby, but Windows 7 is Steve Ballmers' baby. Given how smoothly Windows 7 development and rollout has gone, and given what a disaster Vista turned out to be, one has to give a tip of the hat to the Ballmer way of doing things.

Yes, Microsoft has had some clunkers as of late, but that is more due to years of sloppy practice and bloated software that had little to do with the CEO. Even with the company in the worst situation it has seen in years, it seems a great many Microsoft employees still hold a firm belief in the company, and a lot of that has to do with Ballmer.

10. John Perry Barlow



Shaun Nichols: Okay, so I guess Thomas Dolby isn't the only one who can claim a hit song and a major IT outfit.

Alternately described as a lyricist, activist, anarchist and libertarian, John Perry Barlow has done a great many things in his quest to bring freedom and openness to the world.

The one project that endears him in our hearts, however, is his work for online freedom. In 1990, Barlow was one of three activists that helped to establish the Electronic Frontier Foundation. Since the early days of the internet, the EFF has been on the forefront of the battle for user rights. The group has launched extensive legal campaigns against everything from DRM to heavy-handed use of the Digital Millennium Copyright Act.

Not bad for a guy best-known for co-writing Grateful Dead hits.

Iain Thomson: John Perry Barlow was a nightmare for people whose default conversational gambit is “So what do you do?”

His career spanned animal husbandry, Grateful Dead writer, rancher and social activist.

Steve Jobs once reportedly said that Bill Gates would be a broader person if he'd dropped acid. Barlow seems to have got that out of the way first, along with heroic doses of Wild Turkey with fellow Grateful Dead members for over a decade before discovering the Well in 1986, the very dawn of the internet community movement. He brought a little rebel attitude to the web, and left a lasting mark.

Since then his co-invention, the EFF, has been in the vanguard of protecting our online freedoms. It keeps companies and governments honest and is willing to fight for the rights of computer users everywhere.

9. William Shockley



Iain Thomson: The co-inventor of the transistor was a difficult man to work for, and had some distinctly odd ideas about the human race.

Shockley was one of the three men behind the invention of the transistor at Bell Labs, work for which they shared a Nobel Prize. But he was reputedly so abrasive to work for that he passed over fro promotion and left to use his skills to set up Shockley Semiconductor Laboratory, America's first semiconductor firm based in Mountain View, California.

The new company didn't change his management style and he annoyed staff due to paranoid fears that his inventions were being stolen. At one point everyone in the company had to take a lie detector test to prove their loyalty. This riled many staff and the so called 'Traitorous Eight' left and started Fairchild Semiconductor, which begot Intel.

Later in life he became devoted to the subject of genetics. He believed that humanity was doomed if people of low intelligence reproduced more than clever people and advocated paid sterilisation for anyone with an IQ lower than 100. When he sued for libel after the accusation that he was 'Hitlerite' he won, but was awarded just one dollar in damages. He even donated sperm to a Noble Prize sperm bank so his genes could be passed on.

In the end he died a lonely, embittered man, estranged from most of his family, a sad end for one of the pioneers of Silicon Valley.

Shaun Nichols: One thinks that Shockley and Steve Jobs might have hit it off rather well.

Many of the people on our list either overcame or leveraged their oddball status to become very successful in business and happy in life. This was not the case with Shockley.

His controlling ways and paranoid point of view drove away many of his employees. One can only imagine how huge Shockley Semiconductor would have been had he not alienated his most talented engineers. Even Steve Jobs and Larry Ellison have the good sense to keep their best talent happy, and so within company walls.

In the end, Shockley's eccentricity was his greatest liability, not his greatest asset.

On another note, his views on stupid people reproducing sound a lot like the plot for the Mike Judge film "Idiocracy," perhaps someone at the Shockley Estate should give the lawyers a call...

8. Charles Simonyi

Shaun Nichols: So who among us didn't at one time or another dream of becoming an astronaut? Hungarian-born software icon Charles Simonyi got to live that dream, even if it was a little later in life than he had imagined.

Simonyi emerged from Eastern Europe to attend college in California and later join the Xerox Palo Alto Research Center in the late 70s. In 1981 he was hired by Microsoft and helped lead the development of Word and Excel. This of course endowed Simonyi with enough money to buy and sell all of us several hundred times over.

But that's not all. In 2006, Simonyi decided to leave his sizeable bank account, ground-breaking software firm and 28 year-old Swedish millionaire wife behind here on Earth and hitch a ride to the International Space Station.

Okay, so maybe it's not "strange" so much as "really, really cool," but there's no doubt that Simonyi is very much a one-of-a-kind person.

Iain Thomson: By the Pratchett definition Charles Simonyi is not strange; he's eccentric. It's like strange, but with a lot more money.

As a programmer he developed the idea of a master infrastructure to code development. A central designer would show the goal and coders could noodle around so long as they achieved it in the most efficient manner possible. Also, by developing a central architecture, Simonyi made applications development much more efficient.

But he has his moments. He's the only time return visitor to the International Space Station, spends much of the year on his custom-built yacht and threw over a fifteen year relationship with Martha Stewart of a Swedish girl under half his age.

That said, he's also founded the Simonyi Professorship of the Public Understanding of Science at Oxford University (first holder: Richard Dawkins), so maybe a little oddness isn't too bad.

7. Seymour Cray

Iain Thomson: Silicon Valley is a wonderful place to live and do business, or so millions of people seem to think. However, for Seymour Cray, it was just too full so the father of supercomputing was happier in to Chippewa Falls, Wisconsin.

He spent the Second World War in Europe and supporting the Philippino Guerilla army in the Far East. He then came back, got a degree and set about changing the way we build and design computers. For decades later in life the name Cray would be synonymous with high performance computing.

He was by all accounts an odd person to work for. He was brilliantly inspired, but insisted on an absolutely quiet workplace and part of his move to Wisconsin was to get away from customers who kept disturbing his work. The other was reputed to be a fear of nuclear war.

Cray was also something of a loveable oddball. He claimed once that his skills were given to him by the elves, he dug tunnels to relax and was a talented windsurfer. But what makes him special for me is his single-minded purpose and his willingness to walk away so he could do things his way.

Shaun Nichols: Some people spend their downtime at work cruising Fark.com or catching up on the latest celebrity gossip. Seymour Cray used to sit at his desk and design logic circuits.

He was so focused that as soon as he was able to run his own facility, he promptly moved the entire operation from the hustle and bustle of Minneapolis, Minnesota and into the frozen forests far outside of town so that he would be able to work free from the reach of those pesky management types and get some peace and quiet.

The results speak for themselves. Cray was one of the driving forces behind the development of the supercomputing field, and many of his designs remained in use for decades. His Cray I and Cray II supercomputers both sent shockwaves throughout the industry, the later holding the top speed ranking for five years.

Personally he was also rather remarkable. An electronics genius since early childhood, he also possessed business savvy and an uncanny knack for setting off on his own when he first formed Cray Research and Cray Computer Corporation (though the latter went bankrupt after the end of the Cold War deflated the supercomputer industry.)

6.Gary McKinnon

Shaun Nichols: Okay, not to disparage Mr. McKinnon or make light of his legal struggle, but the guy is a little weird.

It's one thing to believe in UFO's and government conspiracies. It's another to actively seek out government documents which prove it. And it's a completely different level to then hack into NASA computers in order to obtain evidence that aliens have landed on Earth.

That's not to say we aren't huge fans of Gary McKinnon and strong supporters of his cause. That the US government would put so much effort and malice into charging McKinnon for his actions is completely absurd.

For those who would preach about bringing a criminal to justice, I say that as an American citizen I am far less concerned about charging a non-destructive computer criminal than I am about the fact that the US military had dozens of its systems compromised by a systems administrator from Glasgow looking for photos of little green men.

Perhaps rather than sending McKinnon to jail, the government should put him to work teaching network security to its own IT admins.

Iain Thomson: Despite attempts to portray McKinnon as a master hacker the facts show that this was simply an odd character who got lucky.

By some accounts McKinnon got into highly classified US military accounts just by typing admin into the password box. The admission that the US Navy was still using Windows NT4 was even more shocking.

I've met McKinnon and he's nothing more than a skilled script kiddie. By all accounts he entered these networks just to search for evidence of ETs. The fact he had any damage seems down to ineptitude rather than ill-will.

5. Mark Cuban

Iain Thomson: Plenty of people who made it big in the software industry and cashed out at the right time. Some of them even bought sports teams. But Mark Cuban has taken things to another level.

The man behind Broadcast.com is every inch the rough diamond. He owns the Dallas Mavericks basketball team and to date has been fined over $1,665,000 for improper behavior at games. That still hasn't stopped him screaming from the sidelines ,wearing his 'I'd rather be fighting the man' tshirt.

He's funded the legal fight by file sharing service Grokster, distributed a film highly critical of US conduct in Iraq and has started his own stimulus plan looking for good business ideas. Cuban is certainly one of the stranger characters in the industry.

Shaun Nichols: Like Simonyi, Cuban is one of the rare individuals who did not get consumed by his business success and, rather than become an obsessive boardroom zombie, he went back to living like a regular person would... if they had billions of dollars.

Cuban's life is a bit like one of those movies where an average Joe (usually Tom Hanks or Adam Sandler) falls into a huge pot of money and proceeds to cause utter chaos amongst the moneyed elite. One of the first things he did after cashing out Broadcast.com to Yahoo was to buy a lifetime ticket on American Airlines and spend months travelling the world.

He then came home and did what any American sports fan would do; buy your favourite team and run it better than those stuffed-shirt bozos that had it before you ever could. Rather than sit up in the box wining and dining clients, Cuban is down on the floor, usually in a team jersey, cheering on the players and screaming at the officials.

Though he is a bit irritating to some people, I find it very hard not to like and respect Marc Cuban the individual. He is a shrewd businessman, but he is not defined by it. He's able to have a great time and still contribute to some very noble causes.

4. Peter Thiel

Shaun Nichols: Peter Thiel comes off to me as something of a cross between Larry Ellison, William Randolph Hearst and Ayn Rand.

He made a boatload of money as the founder of PayPal, and then moved into the venture capital industry with investments in the likes of Facebook, LinkedIn, Yelp and Friendster. Not a bad record at all.

But it's Thiel's actions outside of the board room that are the most interesting. A hardened Libertarian, Thiel was a big supporter of 2008 presidential candidate Ron Paul and earlier this year he wrote an article for the Cato Institute that was a bit contentious, to say the least. Among the main points of the article was the suggestion that women's suffrage was partly to blame for the decline of capitalism.

Thiel has also put his backing behind several major research projects, including anti-aging studies and artificial intelligence development. Don't be surprised if 30 years from now Thiel emerges as some sort of cryogenically-preserved computer-aided politically fanatical financial genius James Bond villain.

Iain Thomson: Thiel really worries me. He's surfed the technological wave for fun and profit but there's something about him that makes me think of Ross Perot.

Thiel is gaining a certain ideological following in Silicon Valley and the wider world beyond. While some of his ideas are good a lot are simple bull-headed stupidity. However, he has a fleeting bully pulpit to push them.

Technologists should stay out of politics. Human beings aren't bits and bytes, no matter what market researchers will tell you. Getting good at software doesn't make you a world leader.

3. Ada Lovelace



Iain Thomson: Ada Lovelace had a rather unusual upbringing. Her father, the poet Lord Byron, spent most of her early years organising revolution in foreign climes and her mother was that most unusual person of the 1800s, so meone who believed a woman should be educated too.

The notion that women could do just as well as men if given the same opportunities was a radical one but Ada repaid it in full, by excelling in science and mathematics. She became a close friend of Charles Babbage, then building the first non-digital computer - the Difference Engine. In 1843 she translated a book on the engine by Italian mathematician Luigi Menabrea and included, in notes three times longer than the original book, that the engine could be used to calculate a sequence of Bernoulli numbers. It was the first computer program.

Babbage called her "The Enchantress of Numbers" and society was wowed by the woman. She married the Earl of Lovelace and bore him three children before carrying on her work in the fields of mathematics.

But by the standards of the time she was even more outrageous. She pawned her jewellery to cover gambling losses, drank prodigious amounts, smoked opium regularly and there were rumours of many infidelities. Certainly not a woman Jane Austen would have approved of.

Shaun Nichols: A hard-drinking, fun-loving empowered woman that also happens to be a computer genius is pretty rare today. But in the early 19th century it is downright amazing.

As Iain mentioned, Lovelace was rare for her time in that she was a highly educated woman, but she also had an immense natural intellect. When Babbage was designing his Difference Engine, it is said that Ada Lovelace wrote a series of instructions for manipulating the machine and creating an intended result. Thus, she is widely regarded as the first computer programmer.

That she managed to do it all while living in aristocratic 1830's England is absolutely mind-blowing.

2. Steve Jobs

Shaun Nichols: Iain, we really have to stop putting Jobs or Woz at the top of every list we make.

That said, Saint Steve most certainly deserves a spot on this list. The Apple chief executive may be a marketing genius and technological visionary, but he's also more than a little weird.

How many consumer electronics companies can trace their entire design philosophy back to a college calligraphy course? It is said that much of Jobs' tastes for the simple yet elegant style of Apple's products comes from a calligraphy he took in his days before Apple.

After founding Apple, it got even stranger. As it grew from a garage operation to a major tech firm, Steve Jobs took a very hands-on approach to running things. He was said to have recruited one engineer by simply unplugging his computer and carrying over to the Macintosh project office, all while the stunned engineer was sitting in front of his desk.

Then, he became chief executive of the company, and it got even worse. Jobs strict management style and unpredictable nature have become legendary, and many who have worked at the company speak of his micromanagement. Tech columnist Dan Lyons once likened Apple as "the church of Scientology goes into the computer business," and he wasn't far off in my opinion.

Iain Thomson: Silicon Valley historian Robert X. Cringely once told a tale about Steve Jobs that rings strangely true.

In Apple's early days Jobs would wander the corridors, find an employee and ask them “I thinks xxx is an asshole; do you agree?” If the employee said no he would walk on, but if they said yes he'd walk with them to someone else and say “We think xxx is an asshole; do you agree?” With bosses like that who needs an excuse for an evening with a high tower and a rifle.

The problem is that Jobs has really good ideas. You can put up with a lot so long as you're surfing the winning wave and Jobs is so good for Apple. Seeing how the company languished when he was away shows how Apple is dependent on strangeness.

It helps that Jobs at his best is the consummate salesman. Want a computer you can't modify? Don't like having removable batteries? Want an iPod without a screen? Apple's got the brand for you.

1. Richard Stallman

Iain Thomson: Bill Gates once said that he'd be stunned if there were more than 50 people in the world with as much programming experience in the world as him when he started Microsoft.

Stallman was one of these but rather than become the richest men in the world he has devoted himself to a vision of how computing should be. In many ways he shares a lot of attributes with Steve Jobs in his self-belief, but peppers his life with such oddity he had to make the number one spot.

After a knee injury forced him to abandon folk dancing (I'm not making this up) Stallman devoted his time at MIT to polishing his software skills. When DARPA introduced a password system at the computing centre he hacked the system to give unlimited access to those that wanted it.

His trailblazing work at the GNU project has made a world of free software available to all but Stallman retains his odd side, living a nomadic existence without the trophy house or even a mobile phone to his name. He looks the part of the hairy hacker down to a tee too. One wonders what government leaders think when Stallman bears down on them, but it certainly works.

He also inspires strangeness in others. Stallman was presented with a Japanese fighting sword after the popular XKCD started publishing strips with him wielding one, or two. As Hunter S. Thompson put it: “When the going gets weird, the weird turn pro.”

Shaun Nichols: Not only can Stallman program better than Gates, but he can dance better than Woz.

He may look like an Appalachian hermit, and be as hard for journalists to contact as one (the pre-conditions one must meet before interviewing him are quite extensive,) but Richard Stallman is also a very admirable person.

As Iain mentioned, Stallman's was such a brilliant programmer that had he gone commercial, he would likely have made himself a billionaire several times over. Instead, he went completely the other way and devoted his efforts to creating and maintaining free software. One has to admire the person who can turn down millions of guaranteed dollars and instead opt to give out his work for free, because almost none of us would have done the same thing in Stallman's position.

His vision may also be a bit impractical, however. While Stallman himself enjoys a more or less lifelong appointment at MIT, there are only so many Universities in the world, and while many developers have made a nice living writing Linux applications, the GNU licenses have also proven to be difficult for developers to work with, particularly when trying to interact with closed-source outfits such as Microsoft that don't especially enjoying opening up their code to the outside world.

But I digress. Stallman has for the last four decades been an unconventional and highly influential force in the computing world. It's safe to say there is no one like him in the world.