A Year on Airbnb

In recent months, I’ve stayed in over 60 Airbnbs in 25 cities. I’ve connected with many extraordinary people and had one of the most successful business years to date.

I’ve been exploring and testing methods to design a paradigm that supports my ideal lifestyle, rather than relying on default societal constructs.

It’s been an adventure of streamlining and optimizing life and business to create more time and the flexibility to work from anywhere. Here's my story….

I started this journey somewhat by accident. Less than a year ago, I was living in Venice Beach, CA. I had achieved a certain level of the success I had been striving for—my company established in multiple cities, high-end clients, a loft near the beach, cars, etc. However, I was beginning to feel that I was painting myself into a corner and not living my fullest potential. This left me feeling generally stressed, unfulfilled and not really in control of the most precious non-renewable resource: TIME.

While waiting for a new lease to become available, I used Airbnb to explore some new neighborhoods. I happened upon some incredible places, some of which were sprawling estates nestled in the hills of LA. I realized I could just as easily (and less expensively) live between a few favorite places rather than subscribing to a single-residence ideology.

I began venturing further afield, heading up the coast for extended periods to San Francisco and Portland, taking advantage of my newfound flexibility. I could choose to stay in a place for two weeks or two days. I was able to spend more time connecting with colleagues and expanding my network while continuing to refine this virtual lifestyle.

That’s when I decided to redesign my paradigm, and explore the full potential of this lifestyle experiment.

I got rid of unnecessary baggage, and I found detaching from all the stuff I had accumulated to be deeply liberating. I began optimizing and streamlining life and business wherever possible, stripping things down to their essential components. I leveraged services like Upwork.com to outsource financial and administrative responsibilities. I let go of my largest office in exchange for a much smaller space limited to essential staff only. All of these changes allowed for much more time, flexibility and freedom.

So far I’ve stayed in over 40 Airbnbs and I’ve had an amazing journey traveling between 20 cities, including…San Diego, Sedona, Santa Fe, Austin, New Orleans, Atlanta, Virginia Beach, Washington DC, New York, Toronto, Detroit, Chicago, Vancouver, Seattle, Portland, San Francisco and Mexico City.

Along the way, friends and colleagues began to ask me how they could apply these strategies in their lives and businesses, and I began to see that sharing insights from my experiences had real value for others. 

When it comes to giving advice, I think Derek Sivers sums it up beautifully.. 

“My approach is just one way, and I could argue against it as well. I’m pretty unconventional, so what works for me might not work for others. Enough people thought that the stories and philosophies that I developed from my experiences were worth sharing, so here we are."

*The aim of this project is to find freedom by leveraging modern tools and platforms, and to empower one another to consciously design a lifestyle which supports our deepest contribution.

Welcome to the adventure, my friend. I hope to see you out there…