Kevin O'Leary on buying his Porsche as part of the 'decade of Daddy'

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He made his fortune after selling his software company to Mattel. In the business world, as a venture capitalist and private equity investor, Kevin O'Leary is ruthless, arrogant and opinionated.

The risk taker and TV show host also gambled on a vehicle that wasn't exactly practical for his family. To mark a milestone, or what some might call a midlife crisis, O'Leary bought himself a birthday present a few years ago - a 2004 Porsche 911 Carrera C4S convertible.

"When I turned 50, something clicked in my head and I said, 'I'm not going to live to 100. I'm half-cooked already.'"

"I set the family down and I said, 'Listen everybody, we're now entering the decade of Daddy. We're going to start doing things that I want to do.

'Once in a while, I'm going to make crazy economic decisions like buying this car, which has nothing to do with getting everybody to school, packing up boxes, because you can't even put your golf clubs in here, but it's a lot of fun to drive and it's part of my decade to Daddy.'"

When he rolled into the driveway of his Muskoka cottage, his wife Linda had one comment, "'Oh, great. Look another bald asshole in a Porsche!' That's exactly what she said," he laughs, before adding "don't print that, my wife will kill me!"

His two kids, aged 10 and 14, weren't too fond of the Porsche, either. "I once put all four of us in it because it does have a back seat. But my daughter said, 'This is crazy! There's not enough room.'

"My wife doesn't like it that much because, let's face it, you feel the road. It's wound very tight. You feel every bump. She's not a big fan," says O'Leary, who cohosts the SqueezePlay TV show on the Business News Network and will be shooting season two of the Dragons' Den show on CBC this summer.

"I don't want to sound like I'm selfish or anything. It's just that I'm starting to think about things that I want to do, things that are fun.

"One of them is driving a car like a Porsche. I've driven a lot of cars - sedans, trucks and big family vehicles all year long. But there's nothing like a four-wheel-drive Porsche.

"When I come up here for vacation, I want to scream down the highway at 120 miles an hour and know that car is stuck to the road. Nothing handles like a Porsche. They build a car like nobody else does.

"It's not the fastest car. This is not a turbo. This is under 400 horsepower. But in terms of handling, I love it. It just feels rock solid. It's such a pleasure to drive this thing," he says passionately.

"It's not that you can accelerate to 100 easily, it's [that]you can stop easily. I wouldn't trust anybody doing 100 miles an hour in anything but a Porsche, or maybe a Ferrari or Lamborghini, because they can decelerate and stay in control as you're decelerating.

"If someone is behind me doing 100 in a Porsche, okay, I'm alright with it. I don't want a Ford, I'll tell you that."

On the downside, the Porsche lacks trunk space and an iPod jack. "If you spend that much money on a car, you want to be able to put in some decent audio equipment.

"There are a lot of impractical things about owning a Porsche. But they're all offset by the driving experience. It really is unique.

"Lamborghinis and Ferraris come close. And they are more powerful, but they don't handle like a Porsche," says O'Leary, who sold The Learning Company to Mattel in 1999 for $3.5-billion dollars (U.S.) - one of the largest tech deals in Canadian history. Shortly after, Mattel basically gave TLC away.

When O'Leary bought his Porsche, it was the first time he bought, rather than leased. "I don't think cars are a good investment. I don't buy cars. I lease everything, except this Porsche. I just walked into the dealer and said give me a Porsche. That's what happened.

"But the practical reality of managing cars in the family - I do 36-month leases. I think they're horrible investments. And you want to give them back after their warranty is over," he says adamantly.

O'Leary divides his time between the Muskokas and Boston, where he runs trust funds.

In Boston, he drives a "very, very boring car" - a GMC Envoy truck. "I don't know if you're familiar with New England winters, but when you get stopped in there, you better have a truck."

He has also been stopped for other reasons. "I was driving on Marlborough Street in Boston and I wasn't looking at what I was doing.

"A woman was pulling out from the left side and I nearly hit her car. I stopped and I missed. And she beeped at me and I kept driving. Of course, the light turned red and we were right beside each other and it was that really embarrassing moment.

"I rolled down the window and I said, 'I'm sorry.' She said, 'You should look at what you're doing!'"

O'Leary loves speed, but he's trying to curtail the habit. "I just can't afford to be clocked at high speeds. I don't do that any more. It has taught me a lesson.

"It [speeding]costs me a lot in insurance and everything else. That's the problem with owning performance cars. You never get to drive them. By the time you're pulling out of second gear, you're already speeding," he says.

"You're always trying to achieve the perfect shifts and you can never get it into third or fourth without speeding. It's just a heartbreaker.

"Those cars aren't very practical in the city. Even the Porsche in the city is a headache shifting out of first and second. These cars want to be going a 100 miles an hour. They're completely comfortable at that speed. That's the speed they're just humming at. The gears are set up that way. They feel comfortable."

At the moment, O'Leary has a dilemma on his hands. "My big debate is do I keep it another year? It has only got 15,000 miles on it.

"I took it out when I got up here to check it out. It was sitting there all winter. It roared into life with one turn of the key. I put the top down - it was 32 degrees. It was freezing.

"Heated up the seat, went ripping down the road. It was wonderful. And, no, I wasn't speeding!"