Who more exemplified the libertine lifestyle than the late, great Hugh Hefner?

Just that name brings forth the image of him in his smoking jacket with a few buxom and scantily clad ladies a lifetime his junior behind him.

It could be reasonably argued that his work single-handily sparked the American sexual revolution of the 60’s and 70’s. He had the ability to elevate the naked female body into a sophisticated and elegant tapestry of art.

But it was never just about the boobs.

Beyond the ladies, beyond the expensive cars and high-class cigars, and beyond all the rest of the glitz and glamour there was a message. That message was one of personal freedom. That individuals, and therefore society, should be free to choose what they want to do and how they live and to not be shackled by the way your parents, or anybody else, think you should behave.

“Progress necessarily requires the exchange of outdated ideas for new and better ones. By keeping open all lines of communication in our culture, every new idea—no matter how seemingly perverse, improper or peculiar, has its opportunity to be considered, to be challenged and ultimately to be accepted or rejected by society as a whole or by some small part of it. This is the important advantage that a free society has over a totalitarian, for in a free exchange of ideas, the best will ultimately win out.” – Playboy’s Philosophy

This philosophy, displayed in the much-praised articles of his magazine, vaulted Hef into his place as an American icon. Far more than just showcasing naked ladies would have done.

Hugh began his journey to change the minds of America when he left his job as a copywriter for Esquire magazine after they denied him a $5 raise in 1952. After raising $8,000 from investors, he started Playboy and eventually built a fortune that was estimated to be worth over $400,000,000 at its peak.

This sort of success is almost uniquely American. Hef imagined the life he wanted to live and made it real by becoming the persona in his dreams. Others wanted to be him and would pay him for a glimpse of his life. This money enabled him to continue to live that lifestyle. The whole concept is pure genius. I salute you, Hef.

Hef died last year, leaving an estate valued around $50 million. Still a fortune, but far lower than it once had been. Playboy had been in trouble for decades. Its success in diminishing American Puritanism opened the doors for a multitude of competitors. Competitors who wrote less and showed more. Then came technology, specifically the internet, in which Playboy never managed to gain traction in.

Still, Hef never changed his relaxed and carefree lifestyle.

So I asked myself, how much does it cost to live the life of an international, jet-setting Playboy/Playgirl? A pleasure-seeker who can spend the week in Prague, fly to London for the weekend, then end up in Lisbon before heading off to Switzerland to ski? Someone that even their friends or family can’t explain how they have the time, ability, and money to live such as they do?

What secrets do they know that the majority of people do not?

Believe it or not, there are many people that live like this – and no, they are not multi-millionaires like Hef.

Secret Number 1: They aren’t tied down.

To be able to travel whenever you want, you have to not be tied down. No spouse, no kids, a job that they can do anywhere at a time they choose. It’s hard to live the Playboy life when you only get two weeks of vacation per year or have to get the kids to school in the morning.

They answer to no one but themselves.

Secret Number 2: They live in Europe.

To Americans, all these European locations sound exotic. But to travel to another country in Europe is almost the same as heading to the next state over – both in time and expense. For an American to get to Europe it might cost a bit, but once you are there it is ridiculously cheap to travel around. A flight from Prague to Paris costs in the neighborhood of $70 or about a weeks worth of groceries. Add in some bargain last-minute hotel rooms or AirBnB rentals and it might not cost more than $500 for the week.

They have the flexibility to grab last-minute deals and can travel cheaply between exciting locales.

Secret Number 3: They own little and what they do own is an asset.

Some Playboys own an abode in multiple European countries, but instead of costing them money every month they support this lifestyle. How? The real estate was purchased with the intent to rent it out when they are not using it. So if they stay in that city, they use their property. When they are away, it is rented out. The management of which is often hired out for not too much at all. Income making machines. This strategy enables the income of the property to cover the mortgage and other expenses and then some.

Smart purchases make them a profit while they stay on permanent vacation.

Secret Number 4: They pay less in taxes.

In Portugal you can be a “non-habitual” resident and receive 10 years in which you pay no taxes on income earned outside of Portugal. That’s not the only country with a reduced income tax for non-domiciled residents. Ireland, Cyprus, Czech Republic, Andorra, Bulgaria, Montenegro, Gibraltar, and possibly others have similar offers. Less taxes paid means more money to have fun with.

Of course, Americans get screwed here. Only two countries in the world require taxes on your personal income whether not you ever live in the country - the USA and Eritrea. Still, passive income from real estate and dividends have tax advantages and reduced rates.

Secret Number 5: They chose the unconventional.

What is luxury? Is it something everyone else wants or is it something that is expensive and therefore out of the range of most people to afford?

Why does a London or New York City ‘ritz’ area apartment cost $3+ MILLION dollars? Is it really better than other places or are most people too unimaginative to think outside the box?

To a Playboy of good, but limited, means these places are too obvious. You want to be mysterious and different, don’t you? Hugh Hefner wasn’t just wealthy, he was wealthy with STYLE.

That’s why a Playboy would choose a much less obvious, but still full of amenities, a city like Prague or Budapest to spend more of his time in. You get all the fun for a whole lot less money. For under 100,000 euros you can OWN a fancy flat near the city center - in Manhattan that might rent you a parking spot for a year or two.

You save thousands every month and your enchanting urban locale shrouds you in an enigmatic veil. You can now afford those amazing hand-made $1,000 crocodile-skin cowboy boots. A choice that is far more attainable than some overpriced and run-of-the-mill luxury item from Gucci.

Speaking of mills, why settle for an ordinary house? Find an old windmill or watermill somewhere in those less expensive places and renovate it. I recently saw an old watermill for sale in Portugal for less than 50,000. Renovate it for 20,000 or so and now you have a unique abode. And when it comes time to rent it out, your property will stand out from the crowd. The less obvious and little heard of choice is the better deal when you have just a little imagination.

The same way of thinking goes for cars too. Why drive around a Ferrari, Lamborghini, or Bugatti? Those are for shmucks that can't think for themselves and need to be told what is cool. You, my friend, can grab more attention for far, far, less.

Ever heard of a Morgan Three-Wheeler? You can buy a used one from a private party for around $30,000 or about 1/60th the price of a Bugatti. A Morgan is just as luxurious but even more of a head-turner. And when you aren't using it, have it up for daily rent.

Don't want the obvious. The obvious is overplayed. Be rare or unique.

The same goes for clothes. Why dress in a luxury brand when you can get a bespoke suit made from the finest materials for a tenth of the cost of something from Savile Row? Head to Istanbul or Ankara and you will see what I am talking about.

What Does This Lifestyle Cost?

The ability to do and go when and where you please will require some financial backing, but not as much as you may think. What you want is the vast majority of your wealth earning you income while you sleep. Passive income that comes in continuously whether you are there or not.

I read that Hef had a monthly income between $200,000 and $300,000 per month in his final years. You don't need that much. You can have everything you need living the lifestyle I outlined above with a monthly income of $6,000 to $8,000.

A life of carefree and luxurious living for what the average American family brings in, except yours doesn't require you to wake up at 6 am to sit in traffic for 90 minutes Monday thru Friday for 40 years.

Take $1, $1.5 million and put it into smart income producing assets and you would never have to work again.

Sound good? Now just ask yourself how you start to build those assets.

How much is between you and the jet-setting international Playboy lifestyle?

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Images courtesy of Newsweek.