Jellaine Ross: The Mindset Behind Cherry Blooms

The first time I met Jellaine was when she showed up for a CouchSurf. She was working on a travel blog then called Backpacking in Stilettos. Her mindset was fascinating back then, and where it took her is the stuff of legends.

Despite debt, career and family problems she grew a million dollar business on her own. She didn’t have investors or a team to help her out. All she had was an unbreakable confidence that she would make it.

That’s exactly what she did.  I’m honored to introduce, Jellaine Ross.

“Law of attraction works. If you want something, put it out there and go and get it.” – Jellaine Ross (Tweet It)

Travel Topics:

  • The story of the birth of Cherry Blooms
  • Identifying ultimate dreams… and achieving them
  • The story of the first product and taking it to the flea market
  • How to leave the corporate job, and commit to the dream of creating financial freedom
  • Inspirational books and authors
  • Her six week trip to Europe that shaped her as a dreamer
  • How previous experience in PR cultivated a vast product knowledge
  • Advice for starting a new business, developing a new product and making the first million
  • The importance of studying and reading
  • Listening to audio books to grow business acumen on the road
  • Three things Jellaine recommends to keep in mind when building a business
  • On the struggle of building a business
  • On fearlessness
  • The future of Cherry Blooms

Lovely Links:

Cherry Blooms | Twitter | Facebook | Instagram

Music Credit:

Jonny Blair: Unstoppable Travel Mindset for Going Wherever You Dream

He has been on the road for 10 years.

He’s gone everywhere and he writes about it.

He can find a job anywhere and his stories are unreal.

If you want to see the world this is the mindset to make it happen.

Say g’day to the travel connoisseur, Jonny Blair.

“Anyone can do any thing if you want it.” – Jonny Blair (Tweet It)

Travel Topics:

  • How Jonny got started on his 10 year journey
  • How much money he saved
  • How picking apples in Tasmania got Jonny to Antarctica
  • What separates long term travelers from the still
  • On the perils of international travel
  • On the road less traveled
  • The key to a successful travel blog
  • Personality traits of  successful travel bloggers
  • From travel jobs to entrepreneurship
  • How he developed an Unstoppable Travel Mindset
  • Getting to Antarctica
  • How to do the Inca Trail
  • How a Northern Irish man sees world peace and how travel impacts his perspective

Lovely Links:

  • Connect with Jonny:

Website | Twitter | Facebook

Music Credit:

Take Action:

What are your thoughts? Do you have faith that you could go to any country on earth and find a job?

Jacob Sokol: Taking on the World to Find True Happiness

Jacob Sokol thought he had it all.

Yet something was missing.

His search took him to South East Asia.

Now he helps turn other people’s pain into purpose and power.

It’s a pleasure to introduce, Jacob Sokol.

“Travel is a vehicle to learn who we are, what’s important to us and what’s possible in life.” – Jacob Sokol  (Tweet It)

Travel Topics:

  • How traveling helps self-understanding
  • Why not having it all figured out can be liberating
  • How understanding other people’s pain can lead to a high quality life for you
  • Why quit a 6 figure salary job to travel the world
  • Why it is realistic to be unrealistic 
  • How Jacob got Tim Ferris to take him to a Jets game with Gary Vaynerchuk
  • How travel has helped to create meaningful true happiness…. by understanding the world
  • Recreating the thrill of travel at home

Lovely Links:

Sensophy | Twitter | Facebook

Music Credits:

Take Action:

Take a look at your environment and relationships around you at the moment – are these conducive to the changes you want to see in life?

Let us know in the comments.

How to Hitchhike the South Pacific with Ben Owen

He left the UK with about $1,000.

To this day he is still living out his dream.

He’s got a blueprint for sailing the world.

It doesn’t cost much at all.

Please welcome the great sailor, Ben Owen.

“8:00 a.m. is the Sailors Midnight.” – Ben Owen (Tweet It)

Travel Topics:

  • How Ben moved to New Zealand with $1K
  • An expert description of the Bay of Islands, New Zealand
  • How Avatar was inspired by the beauty you see there
  • How to sail the world inexpensively
  • Tips for finding the best boat and crew out of The Bay of Islands
  • Best practices to follow before setting sail with someone new
  • Essentials of sailing from New Zealand to Fiji
  • The importance of having an idea on maintaining boats
  • Financial safety nets for sailing the world on the cheap
  • Lifestyle notes for life at sea
  • Navigating immigration problems on the high sea
  • Why to Bring Science, Math and History Textbooks to the Solomon Islands
  • Sailing into New Guinea
  • Exploring Darwin, Australia with Crocodiles
  • Shout out to Lisa and Erik from Tasmania
  • Crazy fishing stories from Northern Australia
  • The value of traveling with a First Aid kit
  • How to catch fish while you sleep
  • What troubles to expect with immigration when sailing into Bali
  • The whole trip was $4,000 including flights
  • How to Hitchhike the South Pacific

Lovely Links:

  • Want to go on the boat trip we discuss at the beginning of the show? Check out The Rock
  • Want to Go Where Ben Did? (In order of Discussion)

Pihia | Opua | Fiji | Vanuatu | Luganville | Santa Cruz Islands |

| Honiara | New Guinea | Darwin | Bali | Queenstown |

Facebook | E-mail

Segment Credits:

Music Credit:

Take Action:

Do you ever dream of sailing the world?

Do you think you’d be willing to take on an adventure like the one Ben did?

Luxurious Housesitting Lifestyle & Firing Fantastic Bosses with the Globetrotter Girls

Leaving high paying city jobs isn’t easy.

Especially if your plan is to travel indefinitely.

But leaning into uncertainty is the first step in living THE dream.

Having lived the location independent lifestyle for years these two girls have specific steps to save you money.

Welcome Dani and Jess, The Globetrotter Girls.

“The idea that you can run your own business from your laptop and travel the world is the ultimate goal.” – Globetrotter Girls (Tweet It)

Travel Topics:

  • Deciding to leave high paying jobs for nomadic freelancing
  • Dealing with a quarter life crisis
  • Why housesitting is the best way to travel the world and build a business that you love
  • How to hack classy accomodation, pools, jacuzzis & workspace
  • Tips on running an online businesses while you travel the world
  • World traveler time management
  • Should I Start a Travel Blog?
  • Travel is not as expensive as you think
  • Why slow travel is the best way to see the world

Lovely Links:

Website | Twitter | Facebook

The Top 3 House Sitting Websites:


Music Credits:

Travel Tools:

Take Action:

What’s your favorite hobby?

Do you think you could make money writing about it?

Leave a comment below! We’ll send pizza if you’re lucky!

Alan Perlman: A World Traveling Cost of Living Analyst finds The Holy Grail

He’s travelled to over 60 countries.

Researching the cost of living.

The Indiana Jones of the Internet World.

Give it up for, Alan Perlman.

“Fortune favors the bold!” – Alan Perlman (Tweet It)

Travel Topics:

  • How he became A World Traveling Cost of Living Analyst
  • The magic of getting off the beaten track
  • Why human connections fuel his long term travels
  • An expert’s opinion on the best places according to cost/lifestyle ratio
  • Leveraging travel experiences and a blog into a career
  • How spare time in travel (waiting for visas, bribing officials) helped him through his Personal MBA
  • Running on adrenaline and shooting from the hip – how dealing with unusual situations rocketed his professional goals
  • Living out an Indiana Jones fantasy: seeing the temple of the Holy Grail in Petra, Jordan

Lovely Links:

 Hubspot | Twitter | Website

Music Credits:

Travel Tools:

Take Action:

Tweet us if you enjoyed the show!

Erik Snare: How We Got Work on an Outback Cattle Station

If you’re planning on working on an Outback Cattle Station, you’re going to be in for something that very few people on this earth ever experience. Most Australians never traveler more than 100 kilometers away from the coast.

Think about that.

If that excites you, you’re going to enjoy this conversation.

Erik and I met on the Gold Coast in Australia and drove 2,000+ kilometers into the outback. Our goal was to attend the Mt. Isa Rodeo and meet some cattle people. We thought they would want to give us a job.

It was a silly plan. The Rodeo claimed to be the largest in the Southern Hemisphere. When we got there, we realized it was smaller than the Reno Rodeo.

We did end up finding a job. It took longer than expected, but the adventure was one that we both cherish to this day.

I hope you enjoy this episode, and I hope it helps you find that station hand position if that’s what you’re shooting for.

“Even if I get stranded out there & I die out there, it’d be a better life experience than what I’m doing right now.” – Erik Snare (Tweet It)

Outback Cattle Station Topics:

Have you ever dreamed of working on a Outback Cattle Station in Australia?

On this episode of the Love Affair Travel Podcast, I talk with my cattle station companion, Erik Snare about the process of selling all his things, leaving his job in the United States and moving deep into the outback to join me in the hunt for a Jackaroo position on a 500,000 acre cattle station.

While I was in South Africa, Erik and I spoke over Skype about how awesome it would be to work as station hands on an Outback Cattle Station. We came to the conclusion that this would be an excellent career path and decided to make it happen.

I met Erik at the Robina Train Station on the Gold Coast of Australia in my struggling 1984 Mitsubishis Express. We drove for five or six days to the Mt. Isa Rodeo in order to find some work in the most exciting way we could imagine.

Believe it or not, this hair-brained strategy worked out and we had an amazing time. At the end of it all, we came out with a hand full of cash and (for more valuably) a wealth of experiences.

In this Episode You will Learn:

  • To avoid the hamburgers and increasing waistline of a desk jockey job
  • How much money Erik had when moving to Australia
  • How long it took from landing in Australia to getting a job
  • That driving in Australia is actually really, REALLY a big deal.
  • What it’s like finding work at the Mt. Isa Rodeo
  • The best way to find employment on a cattle station in northern Queensland, Australia
  • What it was like working as station hands in the Outback
  • How much a Station Hand (Jackaroo) position pays in Australia
  • The intensity of doing dangerous cattle mustering work
  • How learning to canter is like kissing a woman for the first time

Music Credits:

Take Action:

Natalie Sisson: Going Pro as an Entrepreneur, Adventure Junkie and a Digital Nomad Author

Image Property of Natalie Sisson

Natalie Sisson isn’t inspirational because of the things she has done. What makes her inspirational is the nonchalant attitude that she has towards it all.

Want to ride a bike across Africa? Yeah! Let’s do it.

Want to start making $15,000 a month? Where do we start?

Her attitude is contagious. No wonder she wins body sculpting and boating competitions. When your attitude says, “lets do it.” Things happen faster and it’s more fun. She takes this to business, social enterprises and even book publishing.

It’s all quite inspirational.

Thank you for coming on the show Suitcase Entrepreneur. Enter Natalie Sisson.

“Luck is preparation meeting opportunity. I’m always opportunistic and I’m usually prepared.” – Natalie Sisson  (Tweet It)

Travel Topics:

  • How Natalie Sission went from broke to earning $15,000 a month
  • Why a SuitcaseEntrepreneur lifestyle feels stable
  • On deciding to go pro as an entrepreneur and digital nomad
  • Secrets to managing the ups and downs of a traveling entrepreneur lifestyle
  • Natalie Sission shares moments of awe in Brazil, Africa and Australia
  • The story of when Natalie Sisson biked across Africa
  • Why pushing limits in business and adventure feels good
  • Natalie Sisson shares her concept of The Perfect Day

Links by Natalie Sisson:

Suitcase Entrepreneur | Twitter | Facebook

Music Credit:

Take Action:

Grab her book, after all the second edition is out. It’s called Suitcase Entrepreneur.

Whats your next big adventure?

Luke Metelerkamp: Global Sustainability, Travel and a Purpose Driven Business

Image Property of Luke Metelerkamp

Luke Metelerkamp and I met on the farthest southern island of New Zealand. It’s called Stewart Island. This is pretty much the farthest point into the middle of nowhere a person can go without doing a trip to the Arctic or Antartica. That’s the kind of guy that Luke is.

We went our separate ways after meeting at a lodge on this remote island. I think he went back to South Africa where he is from. That was when I went to Australia. We exchanged Facebook friendship while chilling at the lodge.

I knew I was headed to Cape Town for the FIFA World Cup and he was certain to be there wrapping up his studies. He said he would take me surfing and I thought that would be great.

If I knew then what I know now, that invitation should have been viewed with a comfortable level of trepidation. Luke likes to surf big waves in frigid Cape Town water during the nastiest parts of the winter. He’s a machine.

“Travel gets you outside of your comfort zone & open to new ways of thinking & being.” – Luke Metelerkamp  (Tweet It)

Travel Topics:

  • How Luke was inspired by his 5 year journey to start a Purpose Driven Business – An education program
  • On the sustainable practices of the Nepalese and how they inspired Luke to build his program
  • Contrasting the effects of pit mining in India with Nevada and Australia
  • The story of Luke’s treks around far west Nepal
  • Costa Rica: The Environment, Ecology, Surf and Permaculture
  • How to hack a month of snowboarding in Kashmir for about $700

Lovely Links:

Website | Facebook

Music Credit:

Take Action:

What do you think about Luke’s take on sustainability? Could Costa Rica really be the most developed country in the world?

Wandering Earl: Kidnappings, Entrepreneurship, the Taliban and 14 Years on the Road

Image Property of Wandering Earl

He likes to travel to the least visited places on earth.

His first trip was 14 years ago in South East Asia.

It was only supposed to last for 3 months.

Today he is still on the road going as strong as ever.

He’s a hero in the long term travel space.

Please welcome, Wandering Earl.

“The overwhelming number of people on this planet are nice, good people.” – Wandering Earl  (Tweet It)

Travel Topics:

  • How a short trip to South East Asia turned into a 14 year travel lifestyle
  • How blogging helped to focus Earl’s travel driven entrepreneurship
  • Why desperation is a useful tool for a travel lifestyle
  • The tools Earl used to build his first business on the road (hint: pens and paper)
  • How to start a language training business in any (non-english speaking) country in the world
  • Earl’s stories of traveling in Pakistan, Yemen and getting blitzed with the Taliban
  • How Earl was kidnapped in Bangladesh
  • We go on a tangent on how to learn to surf in Mexico or Australia
  • All about Romania and how it is the friendliest country in the world
  • Comparing the cost of living in Australia with that of Romania
  • The opportunity for a Working Holiday in Australia for those under 30
  • Advice for those that want to live a permanent travel lifestyle
  • Developing an open minded approach to making money while traveling
  • Independent traveling with the support of small groups
  • All the other Lovely Stuff

Lovely Links:

Website | Twitter | Facebook

Music Credit:

Take Action:

Now it’s your chance! Share this show on twitter.

Everything you need to know about the Australia Working Holiday Visa

Have you ever had a job on a cruise ship?

Do you find interesting ways to maintain your travel lifestyle?