OS3: Tynan, Beyond “The Game” – RV Living, Buying an Island, Chipotle & More

Tynan The Game

What then is freedom? The power to live as one wishes.

~ Cicero

Tynan The Game
Tynan on his shared island off the coast of Nova Scotia.

For us, Tynan is the Ownstream prototype.

It was through Tynan’s example that we became aware of how many people were experimenting at the fringes of lifestyle design, with Tynan leading the way.

No area of his lifestyle is untouched by an original approach and a fresh point of view. All aspects of his life are uniquely his own, building an overall portrait which radically lies outside of the box.

And, yet, when talking with him, one realizes that his way of life makes perfect sense revealing the conventional path to be all the more absurd.

In 2004, Stephen lived with Tynan for some 7 months when both were pick-up artists at Project Hollywood (well-chronicled in Neil Strauss’s book “The Game”). It is from here that our interview begins, and where Tynan’s choices carve ever more individually and originally. Specifically (time stamps noted):

  • Buying and refurbishing a school bus for long-term road trips with his friends [17:17]
  • Selling most of his stuff within just a few hours, prior to traveling the world for a year [26:48]
  • Living for years in an RV all over San Francisco, and inspiring others to do the same [57:29]
  • Building multiple, successful online businesses [39:54]
  • Embracing minimalism, and always wearing things he truly loves [53:49]
  • Buying an island off the coast of Nova Scotia [1:03:10]
  • Spending 2 hours each morning drinking tea [1:15:08]
  • The sites he uses to snag awesome flight deals [45:30]
  • Eating the same meal at Chipotle every day for lunch [1:19:11]
  • Participating in the World Series of Poker [25:10]

These are just some of the many topics we cover in this revealing portrait of a true original. Tynan is a continuous source of inspiration for us, being the example for minimalist travel that we followed during our 3-months in Asia in 2014.

We are certain you too will be challenged to look at things a bit differently, with fresh eyes, from a clearer angle.


Tynan The Game

Selected Links from the Episode



Show Notes
  • Early experiences w/online “automated” gambling, RTW travel, living in an RV [7:03]
  • Setting up home-bases all over the world (island, Budapest) [9:40]
  • Dropping out of college, how he always knew he would & the 8am class that drove him to quit [10:38]
  • His view on college & traditional learning [13:10]
  • Handling disagreement/disappointment from his parents and how he learned to always trust himself [14:24]
  • Buying, remodeling and traveling with friends in a full-length yellow school bus [17:17]
  • How his professional gambling career began at a party [21:42]
  • Playing in the World Series of Poker [25:10]
  • How he became a minimalist, sold everything he had via Craigslist and then traveled around the world [26:48]
  • Backpacks: how he and his friend decided to live out of smaller, 28L backpacks [29:46]
  • “I do it almost no matter what”, and the value of leaving open your options [31:59]
  • How poker has helped him make big life decisions [34:00]
  • The truth about options and choices in life and how there are always many more than meet the eye [36:58]
  • That time he lost all of his money, his casual response to it, and how it doesn’t control his life [39:54]
  • The only job he ever had [41:13]
  • Time should only be spent building assets [43:46]
  • Paying for travel, how to get great flight deals & working while on the road [45:30]
  • First round-the-world trip [47:48]
  • How has designed his life to be location independent [52:07]
  • His current travel gear essentials (+ ripping his closets out) [53:49]
  • Full-time living in an RV & how not to get parking tickets in San Francisco [57:29]
  • How to buy an island [1:03:10]
  • The value of learning on the fly, and using YouTube as a resource [1:06:55]
  • The power of excitement and the rare time when he wouldn’t follow it [1:07:52]
  • What fuels his excitement and how if no one has done it before, he’s more likely to do it [1:09:30]
  • Being the “least spiritual person on earth” & the worldview that allows him to take massive risks [1:12:37]
  • AM routine – 2 hours of drinking tea? [1:15:08]
  • 3 must read books: [1:17:36]
  • What he eats for lunch & dinner everyday [1:19:11]
  • The possession he has owned for the longest amount of time [1:21:32]
  • The secret Chipotle deal available to celebrities [1:21:58]
  • The entertainment career he secretly craves [1:22:31]

Photo credits – top: Todd Iceton; bottom: Tynan

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