Why I Chose to Become a Homeless Entrepreneur

You’ve probably heard about people who make a radical lifestyle choice relating to their living abode. Remember that into an apartment? Or the Silicon Valley product designer who ?

This year, I made a similar choice. I got rid of my home.

Goodbye, Las Vegas condo

A few years ago, I saw a killer real estate opportunity, and snatched up an condo overlooking the Las Vegas strip.

It was a comfortable place to live.

The greatest feature of the condo? The views! They were fantastic.

Every bedroom had a great view of the Strip.

Even the bathrooms had a view!

The real estate market worked in my favor, and I made a profit when I sold the condo.

Now, I do not have a home. I do not rent a home. I do not have a vehicle. I have a briefcase, a suitcase and a few things to put inside them. That’s it.

Why did I get rid of my home?

Even though my condo was nice and comfortable, it was a distraction for me — something that sucked away my energy, time and money.

Besides, I didn’t spend a lot of time there. I travel a lot due to my work. It didn’t make sense to leave a nice place abandoned most of the time. What good were the views if I wasn’t enjoying them? Why pay to keep a place that’s just sitting there? Those were the practical reasons why I chose to become homeless.

But there were other reasons, too.

I don’t need stuff to make me happy. In fact, the more stuff I have, the more hassle I’m forced to deal with. And a house is the ultimate hassle. If my air-conditioner breaks, someone has to notice it, find a repair company, make the call, schedule the appointment, let the repair person into the house and pay for the repair.

That, for me, is a headache. If I’m going to spend my time and energy solving problems, I’d rather spend it on meaningful problems. I realized that getting rid of my home would add to my life in the areas that mattered.

• I would have more time to work on my businesses.
• I would not waste my energy dealing with silly problems.
• I would be free of the worry of maintaining a house.
• I would eliminate a major distraction.

It seemed like a perfectly logical and empowering choice. So I sold the condo, and became officially homeless. This was an easy choice for me — one that presented itself as the next natural step in my life.

Here’s how it happened. A few years ago, I met while I was on business in India. We became friends, and I began to learn a lot from this man, an older and wiser tech entrepreneur. He told me that every year he chooses to give up one thing. He selects something that is limiting his potential or holding him back in some way. This practice, he explained, has revolutionized his life. I decided to give it a try. At the start of the New Year, I said no to coffee.

I was surprised at the impact it had on my life. It was a deeply energizing experience, giving me a sense of control and ownership over the direction of my life. Who knew that giving up something so small — a daily morning beverage — would have such a big impact?

I did this again the next year. I said no to tea. Then I got rid of sugary, carbonated, and energy drinks. I eliminated red meat. I even denied myself pie. (Yes, pie.) If these small sacrifices were having such a profound impact, then what impact would a bigger sacrifice have?

I decided to go radical. I decided to get rid of my home.

What else did I get rid of?

When you get rid of your house, you have to let everything go. Unless you want to rent a storage space (not for me), you’ll need to leave behind your bed, TV, chairs, dishes and whatever else is in the home.

I got rid of everything. I don’t own a car, boat or helicopter. Heck, I don’t even have my own yoga mat!

All my possessions fit in a small Tom Ford briefcase and international size carry-on. (Full disclosure: I keep a couple of suits, a tuxedo and a winter coat in my parents’ house in Orange County.) The things I directly own are:

• 1 carry-on
• 1 briefcase
• A few miscellaneous toiletries — toothbrush, deodorant, razor, etc.
• 4 polo shirts
• 6 t-shirts
• 2 pairs of gym shorts
• 2 pairs of jeans
• 1 belt
• Underwear
• Socks
• Tennis shoes
• Casual shoes
• Sweater
• Gold Macbook (it’s getting old)
• iPhone SE (the cheapest one)

Where do I live?

So the obvious question is, where do I live? I have to live somewhere, right?

As I mentioned, I travel a lot for work. If I have a meeting in a certain city, I’ll live there for a few weeks. I’ll find a decent hotel that provides room service. I don’t have to worry about meals, laundry or even making my bed. I can be focused and productive wherever I go. In this manner, I’ve stayed in New York City, Sydney, Paris, London, Sao Paulo and Toronto (to name a few).

Every couple of months, I stay with my parents in California for a while. If I ever get homesick, they’re there for me.

The more I roam, the more I learn. I network like an addict. I’m constantly meeting and learning from fascinating people all over the world.

It’s not about what I got rid of. It’s what I gained.

Letting go of things is one of the best ways to discover yourself. Growing up in a middle-class neighborhood, I always heard people say, “Get a good job.” “Buy a nice house.” “Settle down.” Etc. Why did so much of life revolve around having a house? What if that lifestyle isn’t for everyone?

Through a series of events in my life, I realized that life wasn’t about the things that I had, but about the relationships that I built with people. A house doesn’t fill me with passion. It doesn’t energize me. It doesn’t give me purpose. It’s not a source of joy.

By leaving my condo behind, I was able to learn more about who I am and what I’m passionate about. I live to work on my businesses and to help others. That’s it.

If a house, an apartment or other stuff gets in the way of my passions, then I should leave it behind.

What has been the result of my choice?

The minute I signed the papers on the sale of my condo, something within me — primal, deep, and powerful — was ignited. I felt free. Completely, truly, internally, externally, and absolutely free.

I wasn’t tied down to a zip code or the four walls of a dwelling place. I could go anywhere I wanted to.

Sometimes, people wonder, what would it feel like to have just a few possessions? My own experience was huge relief. My worries vanished. Suddenly, my disposable income shot up, too!

I don’t have a water bill, gas bill, electric bill, property taxes, homeowners association dues and all the other costs that come with home ownership. My fixed costs of living involve some life insurance policies, and that’s about it.

My life is ultra-simple. Minimalism might start with getting rid of your possessions, but it goes much deeper than that. It reorients your mind, helping you focus on the things that truly matter. My minimalism makes my life easy, stress-free and streamlined.

Looking back, I can’t imagine why I clung on to my condo as long as I did. What a waste of money, time, and energy! By eliminating the clutter in my life, I encountered the freedom and power of simplicity.

This lifestyle choice won’t work for everyone. Not everyone has a location-independent job. People choose to settle, buy a home, raise a family and put down roots. That is a good and healthy thing. But individuals and families should make the decision that allows them to enjoy and experience life to its fullest.

For me, minimalism and homelessness have been my path to fulfillment and discovery.

Conclusion

Right now, I’m sitting in a hotel room in Florianopolis, Brazil. My “home” is the seventh floor. I have a view of the beach. I’m not shopping for condos, and I’m not looking for another place to settle down. My mind is clear. My life is simple.

I’m homeless, and I think I’ll keep it that way for right now.