James Kawas is Co-Founder and CEO of The Selling Company, where he is working to change the way people sell their things.

From a young age, James has thought outside the box about the way he works and creates. When he was 17, after already starting his first company, James wanted to meet Brian Chesky, so he created a side project idea for Airbnb, found emails for key employees at the company, and pitched them on it. They liked it so much they invited him to come to present it in person in San Francisco.

In this episode, James shares the story of his Airbnb pitch and a lot more about how to hustle and create opportunities for yourself.

In this episode:
* How James at age 17 cold pitched Airbnb on an idea and ended up meeting and pitching Airbnb leadership in-person
* Applying the same strategy to Facebook
* Starting a company at age 15 to help people buy and sell used goods
* Why James didn’t go to college and getting the Thiel Fellowship
* What the transition from being a founder to employee was like when his company was acquired
* What is The Selling Company and why there is incredible potential in re-selling goods
* Why getting any job is a sales process
* Connect with James Twitter:
* Connect on LinkedIn:

We also want to hear your story. If you’ve created an opportunity and found a career that makes you feel alive, send it to Isaac [at]

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Meet the hosts

I'm an entrepreneur, thinker, and communicator dedicated to the relentless pursuit of freedom. I'm the founder and CEO of Praxis, an intensive ten-month program combining real world business experience with the best of online education for those who want more than college.


  • I’m curious to hear ideas, best practices, and habits or paradigms that other entrepreneurs and business owners find effective when it gets tough and lonely.  Trying to build out your vision, win customers, best competitors, outperform naysayers, motivate partners and employees, and keep a positive energy going all take a toll on you personally.  Sometimes, there’s no one around to help pump you up after you exert a lot of energy pumping up others! How do you keep confident and optimistic?  How do you keep the “eye of the Tiger”?  I’ve got some things that often help me, but I’d love to hear from others what works well for you…

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  • With companies like Airbnb and Homeaway making it easier to rent out a property or just a spare room, there is quite a lot of tax compliance issues arising.  I happen to be one in the crosshairs due to a county based tourism tax that applied to the hotel industry in the Orlando area — each county varies from what I understand thus far. I am still researching where I stand with it all,  and I have until May 4th to respond to the tax collector’s letter.  They don’t really give one much time, do they? I was wondering if any of you had similar issues or knew what the best course of action would be.  Or, if anyone knows a tax attorney for Orlando, that would be helpful. Here is a recent related link ambiguously discussing Airbnb’s attempt to resolve these issues:

    Jump to Discussion Post 9 replies
  • I am currently in the process of ‘opting out of the job paradigm’ in order to free myself and be more independent from the whole government controlled crony capitalist system. Since I am really into bitcoin and think it is going to change the world fundamentally, I am considering starting a business involved with bitcoin, but I need some ideas and inspiration and of course this is where all you wonderful freedom fighters come in! So, are any of you involved in bitcoin professionally, or would be interested in a new venture? What are the next business opportunities in the bitcoin environment? How should one go about basing a business on bitcoin? Looking forward to any input!

    Jump to Discussion Post 4 replies
  • I’m trying to set up a new liberty themed T-shirt business and am looking for a fellow liberty minded T-shirt printing expert for advice or a business that provides a worldwide drop-shipping service. My business model requires a printing method that can operate on a made-to-order basis. If you are that person or know someone who is I would love to hear from you. Thanks David

    Jump to Discussion Post 15 replies