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An 11 Month Road Trip Funded by Making Money Online While Traveling

Compliments of Ian Robinson

In 2015 V (Veronica) and I ran an internet business which empowered us to spend the whole year island hopping in the Caribbean and driving across the United States.

During that time we took a boat from the Dominican Republic to Puerto Rico, flew to Miami, drove to New Orleans, New York, Canada, Detroit, Chicago, Yellowstone National Park, British Colombia and down to Reno, Nevada.

V graces the show with her presence today. Unaware this is about to go down, until I shove a microphone in her face, she’s a willing participant. The aim is for her to help me tell this story. We have alot of fun reminiscing. This was the best year of my life and I’m deeply grateful to share this story.

Note: This is an enhanced podcast so while you listen on your iPhone (subscribe to the podcast) you can see images on the screen.

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Cross Country Links Mentioned:

Cross Country Talking Points:

  • Introducing V [0:28]
  • Why Live in Dominican Republic [0:46]
  • Taking a Ferry from the Dominican Republic for Puerto Rico [1:37]
  • On moving to Rincon, Puerto Rico [2:35]
  • How we flew to Miami, bought a car and drove across the USA [4:44]
  • Thoughts on living in New Orleans, Louisiana for a month [7:23]
  • On the drive from New Orleans to New Jersey [11:02]
  • Hanging with the Mennonite Communities in Harrisonburg, Virginia [12:16]
  • Veronica’s mixed experience with Washington DC [15:00]
  • House sitting in beautiful Livingston, New Jersey [17:03]
  • How we lived in Brooklyn for a month with no accommodation expense [18:20]
  • Explaining how we make money to afford this travel lifestyle [20:14]
  • Leaving New York City to drive North – Disaster strikes! [20:45]
  • Driving across the midwest and into the North West United States [24:22]
  • The decision to drive to Canada on the fly [25:58]
  • The buffalo encounter [26:53]
  • RVing around British Columbia, Canada [28:36]
  • Driving from Glacier National Park to Reno, Nevada [30:24]
  • The overall experience of road tripping across the USA as digital nomads [32:02]

Music Credit:

Take Action:

When was your last road trip? Where did you go? How did you fund it?

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Detroit is a Great Place

Do you have a day or two in Detroit? Here is a list of the cool stuff to do from a local who lives in the motor city.

Downtown

I would just walk around the downtown area. There are a lot of beautiful buildings. Everywhere in Detroit is safe during the day, and you can see a lot just by walking around downtown.

  • Guardian Building – It’s really beautiful on the inside. Check out the Guardian Building Website
  • Greektown – It’s a little strip of restaurants, etc. next to the Greektown casino. There’s always a lot of people around here, and it’s a cool little area.
  • Belle Isle – It’s a bit of a drive out of downtown, but you can see the entire Detroit skyline, and across the river to Canada. Along the drive, you could also cut back into Indian Village which is kind of a standard Detroit neighborhood – there’s blocks of beautiful homes in perfect condition and the next block is abandoned.
  • Check out a Tigers Baseball Game – Not sure if you’d want to see it, but you can usually get $10-15 tickets, and the stadium is really pretty
  • Riverwalk/Hart plaza/Renaissance Center – You can stroll along the river (Canada is right across it), Hart Plaza has some iconic Detroit statues. Renaissance center is GM headquarters, and you can walk in and look at cars on the ground level. Renaissance Center is the giant black, glass tours next to Hart Plaza.

Midtown

  • Detroit Institute of Arts (DIA) – It’s a beautiful building with an incredible art collection. Make sure to see the Rivera/Kahlo mural.
  • Motown museum – Gives you a great history of Detroit and the Motown music movement
  • Jolly Pumpkin Brewery – A brewery on Canfield St has great beers and good pizza.
  • Cass Corridor – If you drive along Cass Corridor between Midtown and downtown, you’ll see abandoned buildings and a lot of cool restaurants and bars.

Corktown

  • Batch Brewery – Brewery on Porter St. surrounded by awesome beers
  • Johnny Noodle King  – A new pho and noodle restaurant on W. Fort which is really cool. The bartender/servers here can tell you a wealth of information on great things to do in the city.
  • Mexican Village – It’s across the freeway from Corktown, but it has THE BEST MEXICAN FOOD!
  • Walk along Michigan Ave. There are a lot of car restaurants and bars. There is a large grassy lot at the corner of Michigan and Trumball – This is where the old Tigers baseball stadium was until they moved it downtown in 2000.

Have fun exploring!!!!!

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Cocktails at the Commander’s Palace in New Orleans Louisiana

What is the Commander’s Palace?

The Commander’s Palace is a legendary restaurant in the Garden District of New Orleans, Louisiana. It’s one of the top ranked restaurants in the city and it’s one of the most famous restaurants in New Orleans. Of course, this makes it a bit of a tourist trap, but it’s a good one.

It opened in 1890. That is really old for the USA.

It’s across the street from the gothic Lafayette Cemetary. It’s a fun place to walk off the martinis and contemplate life.

Final Recommendation

Big thanks to the Rebirth Brass Band for their timeless music. If you’re in New Orleans, go see Rebirth on Tuesday at the Maple Leaf on Oak Street.

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Jock Purtle: How to Build, Buy and Sell an Online Business and Live a Life of Travel

Selling businesses isn’t just for multinational corporations.

Indeed, all you need to do is create a recurring cash flow.

Anything that generates cash flow, can be sold.

Our next guest is the master of this process.

He travels the world, brokering big deals and you can too.

Here he is, Jock Purtle of Digital Exits.

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“There’s risk in everything, but I’ve positioned myself so that I know I’m making the right move.” – Jock Purtle (Tweet It)

Travel Topics:

  • Where he is and where he is going
  • How to mix business and travel for pleasure
  • The story of Mardi Gras and business conferences in New Orleans
  • What it took from Jock to sell his first business
  • An unstoppable strategy for getting a big list of clients fast
  • Why and how Jock sold his cash flowing websites and went full time with business brokering
  • Jock’s vision for Digital Exits
  • Jock’s moments of awe: thousands of elephant seals during mating season
  • The guy who sells “dead things” and why it matters
  • How to start making money with an online business
  • How to sell an online business
  • Logical thinking strategies for business deals
  • How to see the numbers when selling businesses
  • The best way to measure success
  • Plus, much more…

“I’m inherently lazy & what that means is, I’m always going to look for the most efficient path to the result.” – Jock Purtle (Tweet It)

Lovely Links:

Digital Exits | Twitter | LinkedIn

Music Credits:

Take Action:

Ready to start a business? Did you learn from something in this episode? Please let us know in the comment section down below.

Thanks so much for listening. 🙂

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Jeffrey Chernick: Tours as a Rock Star Drummer, Grows an International Business and has lots and lots of Fun

Jeffrey Chernick is a Rock Star.

He started in big finance.

Got out before it all burned down.

Off to Barcelona. Off to Malaysia.

Playing sold out shows with his band Story of the Running Wolf.

Still going strong.

Say hello to the ever so charming, Jeffery Chernick.

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“Malaysia was awesome. I’d go partying and to really cool places backpack style, then put on a button down and go to meetings with 13 Malaysian businessmen.” – Jeffrey Chernick (Tweet It)

Travel Topics:

  • 00.26 – Who is Jeffrey Chernick? What is his vision?
  • 03.15 – Transitioning for Lehman Bros to entrepreneur
  • 05.27 – How to learn the entrepreneurial skill set?
  • 08.35 – The ‘Big Phone’ call and what it sparked
  • 10.51 –  Backpacking in South East Asia and securing million dollar deals in Malaysia
  • 14.09 – Conference Events in Vegas and Barcelona
  • 17.08 – Cold Calling and it’s atlas like power
  • 19.30 – How to understand people and cultivate a persuasive message
  • 21.05 – Moments of awe for Jeffrey Chernick
  • 24.15 – Using an artistic mind to leverage powerful business moves
  • 29.40 – The power of thinking Big
  • 35.55 – How traveling has impacted the growth of Ride Amigos
  • 38.40 – Tips for quitting the job, building a business and traveling

Lovely Links:

RideAmigos | Facebook | StoryoftheRunningWolf

Take Action:

Do you think the artist in Jeffrey has helped him thru business?

Would you like to grow an International Business?

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Sean Ogle: The Location Rebel who Builds Businesses that Can Be Run From Anywhere on Earth

Dreaming of quitting the high paying 9-5 job?

Our next guest proposed a remote work agreement and received his resignation papers in exchange.

Now he runs his own business and lives where and how he desires.

He shares his lifestyle with the world.

Please welcome the Location Rebel, Sean Ogle.

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“People are getting more creative with businesses they create. It’s sort of the best of all worlds.” – Sean Ogle  (Tweet It)

Travel Topics:

  • Sean’s transition from portfolio analyst to Location Rebel
  • Agreeing to move to Thailand to work with Dan Andrews
  • The story of building a profitable blog
  • The value of giving back with a location independent business
  • Why the a selfish investment in lifestyle can lead to greater impact
  • Sean Ogle’s favorite places in the world
  • Reminiscing over the magnificence of Bali, Indonesia
  • Bali vs. Thailand – Starting a business and designing a lifestyle
  • The evolution of Location Independent hotspots
  • How Sean is making playing the Top 100 Golf Courses in the USA into a business exercise
  • The abundance of entrepreneurial solutions to be capitalized on
  • All the other lovely stuff

Three steps to becoming a Location Rebel:

  1. Build relevant skills – Basic Copywriting, SEO Basics, WordPress
  2. Freelance that skill
  3. Apply the skills you master to your own project

“Instead of complaining about what’s wrong, always look for problems so that you can provide answers for people.” – Sean Ogle (Tweet It)

Lovely Links:

  • Connect with Sean:

Personal Site | Location Rebel | Twitter

Music Credits:

Take Action:

Do you love toasters? If so, we’re sorry about all the negative toaster talk. But hey, you’ve got amazing potential as an affiliate blogger so maybe this is a turning point in your entrepreneurial career.

Thank you for listening. Comment below and tell us something you’re going to put to action from listening to Sean.

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Benjamin Jenks: Hitchhiking the USA and a New Perspective on Fear

A spontaneous decision led to a journey across America.

All with the goal of meeting people from all walks of life.

On that path he learned that helping people enriches, enhances and reflects who we are as human beings.

So sit tight for the stop-motion video genius.

The one and only, Benjamin Jenks.

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“Once you realise that we will all pass away some day, there is no fear.” – Benjamin Jenks (Tweet It)

Travel Topics:

  • How Benjamin started with a travel blog and no clue how to sustain himself
  • Willing Workers On Organic Farms (WWOOF) experiences on a flower farm
  • Tales of the Bayou with Timmy Joe Thibodeau, the French-Cajun outlaw
  • Quality of life vs. nominal value of your money
  • Hitchhiking USA… Yay or Nay?
  • The spiritual journey of entrepreneurship
  • How to travel on the cheap

Lovely Links:

  • Learn more about Gary Snyder the model for Kerouac’s “Dharma Bums”
  • Find out about Couchsurfing
  • Connect with Benjamin:

Adventure Sauce | Twitter | Facebook

Books Mentioned:

Music Credits:

Take Action:

Head over to AdventureSauce.com to learn more about Benjamin.

He’s got lots of sweet GIFs over there like this one.

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Ian Cooley: Solo Driving from Nevada, USA to Costa Rica in a Van

This is my philosopher friend.

We met deep in the jungles of Costa Rica.

I took a plane to get there.

He drove all the way from Nevada.

It’s time to go deep with, Ian Cooley.

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“It was good to be alive and it still is.” – Ian Cooley (Tweet It)

Travel Topics:

  • On overcoming the failure of convincing friends to join in your travels
  • An insight into the Mayan Ruins on the Yucatan Peninsula
  • Why Ian wanted to drive from the USA to Costa Rica
  • Core insights for anyone planning a roadtrip through Central America
  • Spending the night in a Jaguar Preserve
  • How often you are searched by the police when driving from California to Costa Rica
  • Why Lago Atitland reminds Ian of Lake Tahoe
  • About the Beauty of Grananda, Nicaragua
  • Why Puerto Viejo, Costa Rica is a great place to see American bands
  • How his journey cost about $500 a month
  • Plus much more lovely stuff

Lovely Links:

Music Credits:

Take Action:

If you could wave a magic wand and have the Love Affair Travel team help you out TODAY in YOUR LIFE, what would you want us to do for you? Who would you want to see on the show?