How about that? Young and brilliant Seeby Woodhouse is now old enough to have regrets.
He made $20 million selling his internet service provider Orcon in 2007. Part of the deal meant he was legally restrained from IT-type businesses.
So he did what everybody in New Zealand was doing in 2007 - he bought houses.
"I went and looked at about 50 houses all over Auckland and then made what I thought was ridiculously low offers to everyone.
"I spent $18 million in three weeks on residential property. I thought, 'cool, I'm bored now ... I'll flick them all off and I'll go on holiday in Europe'.
"Then the recession pretty much started and people started getting nervous and it never happened. It was a good lesson to not buy assets that don't produce income.
"I kind of regret the fact I didn't put the money in the bank and travel for a year and live off the interest. I didn't have as much time off as I wanted because I got stuck with a lot of property."
And that was how life after Orcon began. For Mr Woodhouse, now 35, it was trying to find something to do with the time which had previously gone into the business that he started in his garage as a teenager.
But it was also trying to work out who he was without the company.
Orcon was where his friends worked, and where the culture had shaped itself according to his drive. It was literally and figuratively his company - the logo is purple because he designed it and quite likes purple.
"It was quite hard in the beginning for someone young like me because a lot of my identity was tied up with Orcon."
The deal to sell the company included a restraint of trade agreement, barring Mr Woodhouse from starting a new internet business.
It also came with a two-year consultancy deal which ended almost before it began. "The day after I sold it I walked into my office thinking I'm going to be here for two years. They were like 'here's a box, pack up all your s*** and get out of here'. That was quite a shock.
"I didn't anticipate how hard it was going to be and it was actually really hard."
Mr Woodhouse had done little but work for the previous decade. Orcon was a second home - his first was a rental and the office had his art on the wall, his mountain bike parked in the office and most of his personal property stashed in company cupboards because there was no room in the modest home he rented.
"It was crazy to go home and sit doing nothing. I had $20 million in my bank account and [was] sitting at home in a rented two-bedroom house I had been living in for the last two years and going 'this is depressing'."
The young millionaire has a particular way of approaching problems. Knots don't get untangled without equations. Puzzles have solutions. He is a very systematic millionaire.
So he approached life in the same way.
The sale of Orcon exposed gaps in his life. "I hadn't gone out to the world and seen a lot of stuff and experienced everything."
He hadn't had relationships and says he didn't party. He decided to have parties. Now, after huge organised events and a dedication to Auckland's night spots, he counts Sally Ridge among his friends (Was it romantic? "No. I don't know. I think we just had a joint love of art") and is snapped with the beautiful people.
There have been relationships, and he has just started another. "She's really nice," he says. It's been about two months.
Other gaps were less easily solved. The business had always been a springboard to conversation.
"As soon as I wasn't in the industry, there was no opportunity to have a conversation with anyone and it was quite rough."
He learned to speak outside his immediate passions.
And that became life for three years. Dealing with houses which refused to buck the market and a restraint of trade, Mr Woodhouse's life found a new rhythm.
"I had no desire to do anything. I guess because I had a restraint of trade it kind of squashed thoughts of everything."
Then, one day, an alarm went on his phone calendar to mark the end of that restraint. "I had an alarm programmed into my calendar. I hadn't even thought about it."
It set off an urge to start something new. He had the same thrill as Orcon's early days.
It took six months of casting about before he settled on starting a new internet-based business. "I had no intention of ever doing IT again. I thought I was technology burned out."
The ISP Voyager has been around long enough that Mr Woodhouse worked there as a teenager. And he owned the domain names, among the hundreds of web addresses he had banked. "The universe is telling me something."
The message, eventually, was to turn Voyager into an internet business that cornered the market on connection speeds. With recent purchases of cloud-storage company Net24, and the domain name registry 1st Domains, the company has married its component parts into a model that offers greater value.
As it turned out, he wasn't finished with IT. "I get excited because most of the ISPs are doing such a crap job as they always used to. The service of most providers is so bad. Orcon, we had no money, I never had any funding. We were always poor as hell and we did really, really well because we had a good company culture and a great attitude to customer service. That's basically what made a whole lot of money.
"Now, I've got all of those things and a whole lot of money so I can back myself."
And it is fast. "That's the Seeby magic sauce I'll be adding. If you go to the supermarket you can buy 15 different cans of pumpkin soup. One will be gourmet."
The Government's commitment to ultra-fast broadband will see fibre throughout New Zealand by 2018. Voyager is providing extraordinary connection speeds now through VDSL (very high bit-rate digital subscriber line). The connection is fast enough to allow high-definition video conferencing. Cloud storage becomes as simple as drag-and-drop. Phone systems can be run over the internet.
The Voyager service is mainly aimed at business, isn't cheap ($95 a month plus 50 cents a gigabyte, up to 500GB), but pays for itself, says Mr Woodhouse. The gold-plated service comes with "really knowledgeable uber-geeks" on the help desk.
"I'm addicted to speed," he says.
Seeby Woodhouse bought an Audi and a Maserati with the proceeds of the Orcon sale. The latter car picked up a speeding ticket for travelling at 174km/h on the Napier-Taupo road. He appealed against the ticket, lost, paid it and lost his licence for six months.
"I have a Maserati. It is a car that can happily do 300km/h - not that that's an excuse.
"But there's a difference between doing it in an old rusty Cortina and in a new sports car.
"I love speed," he says. "There's a time and place for going nuts in a sports car.
"I've grown a lot as a person in the last five years. I feel a lot more prepared for the world."By David Fisher @@DFisherJourno Email David