Archive for the 'Travel' Category


In episode #92 of The Dating Abroad Podcast Archives - Kyle welcomes his good friend Sam to the show to talk about Sam's experiences as a black dude in Ukraine for the past 3+ years.

1:23 - Quick introduction of Sam's general life story

8:30 - Why is Kiev the best city?

13:30 - I was helping them trying to get to American schools overseas. So that's basically what I'm tutoring them in

20:44 - One interesting fact that really surprised me...the maternity leave for girls is really weird here.

26:24 - (Talking about Sam's girl) Are there any tradeoffs to that feminine softness and charm that you've noticed?

32:14 - There's a niche here where there are Ukrainian girls who are super into black guys

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In today's episode of the show, I talk about why some guys who travel from Southeast Asia to Eastern Europe are in for an ugly surprise - when it comes to dating, business, and more. Also discussed is the poisons of the "$200 Chiang Mai" lifestyle, and why moving every month is a surefire way you don't hit the next level with business.


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TDT 026: How to Fly For Free


In today's show, I go into details about "Mile + Points Hacking" and explain how it's pretty simple to fly anywhere in the world for absolutely free.


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Thank you to those of you who sent me emails yesterday concerned with the situation in Ukraine --- and the fact that I'm living here.

All I have to say is this:

It's all good.

So far, nothing seems out of the ordinary in Kiev. The next snow wave is coming in, so people are naturally staying indoors more and more. That said, we don't have the martial law imposed here. There will not be any impact on civil liberties or anything of the sort. I'm sure that's NOT the case in cities that are in a bit more conflict in both the East and down near the Black Sea, but as far as the capital city, all is fine and dandy here.

I mean, the current president here has an approval rating of something like 8%, and while he decided to "only" impose martial law for 30 days, who knows how it might play out in the coming months with elections right around the corner. My Russian is good enough to order in restaurants and make a small bit of chit-chat. I'm glad it's not good enough to understand a word on the news channels.

But, we've known they're completely fake news for a while, haven't we?

The hysteria is certainly overblown by the Western media.

Anyways, the latest podcast goes into details about it from the boots on the ground.

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In today's Daily Trouble, Kyle explains the situation he recently had while traveling in Eastern Europe. The sad reality is that if airlines out here want to break into the Western market (which is good for everyone), they are going to need to step their game up.

$372 for a checked bag!

Listen to the whole story in the episode...

As a follow up, Citi did credit me the fee back and even tacked on an extra 5,000 Citi Thank You pionts for no reason.

Here's the card I use (not an affiliate):



Ryan Holmer and his course



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In the latest episode of Troublesome Radio (now on YouTube!), I dive into some quick thoughts on Belgrade, Serbia.

I spent 15 days in Serbia recently, and while I enjoyed my time, I just don't think the Balkans mesh with me as well as other places such as Ukraine, Poland, etc. Something about the region just doesn't click with my personality.

To hear some of the crazy Serbian stories, I'd suggest you tune in to this podcast episode with my friend Papi Rico:

The people of Belgrade, and Serbia has a whole, are fantastic and great folks. Very warm and welcoming, and no, they don't hate Americans (I do mention in the video which political affiliation they prefer you to have...).

Finally, Belgrade and Serbia as a whole are quite affordable.

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Today's episode dives into a variety of Q&A questions about what makes women, travel, and general expat life tick. Many of these questions were answered in daily emails. If you'd like content like this delivered straight to your inbox, sign up at:


Show notes:

4:12 - Kyle gets into the Q&A questions (mostly about women, some about business)

12:20 - The feeling of unrest when always moving

16:10 - How men should have already internalized game

19:30 - Kyle talks about how women can have so many choices once they grab hold of a smartphone (with Tinder, Instagram)

23:00 - The first steps in moving abroad

26:45 - Why the man should be the leader and be able to dictate how things will be with the woman



Jim's amazing comment

Getting girls on Instagram



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In episode 110 of the show, I welcome back Michael Knight of to the show, this time to discuss St. Petersburg, his long-term Russian relationship, and other ins and outs of The Motherland.


Michael’s first appearance on my show was in episode 30 of The Dating Abroad Podcast, where we discussed Albania and Kosovo.


Relevant reading/listening:


Michael’s book, Fundamentals of Female Dynamics


St. Petersburg Travel Guide


Russian Visa for US citizens


17 Things to Know About Russian Culture


Russian Cupid Review


Q&A, Russian Girls


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TR 104: Why Living Abroad Sucks


In episode 104 of the show, I tackle the oft-asked question regarding what's BAD about living abroad.

Truthfully, it's good most of the time. But sometimes, oh yeah - it'll make you tear your hair out.

Make sure you check out the Bang Black Friday package here.

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In episode 100 (!) of the show, I welcome James Maverick of Maverick Traveler to the show. 

James' story of quitting his job was a huge inspiration in my own journey and subsequent success. It was great to have him be the guest on the 100th episode of Troublesome Radio. Time has really flew since I started this show way back in 2015.

Make sure you check out his books, courses, and website. He's on Twitter here.


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Troublesome Radio runs every Sunday at 10am EST.



Podcast notes:


Quick background of who you are, journey from cube monkey to nomad
Struggles - did you ever have moments of doubt, from a financial or personal perspective?
What advice would you give up front to young folks wanting to travel and build online businesses?


How do you make money online?
What businesses have you dabbled in; which ones have been successful, which ones have flopped?
What's your usual routine and schedule look like?
Any tips for being productive whilst in monthly Airbnb rentals, always on the move, etc.


What is your best story or memory from all your travels about the worst?
Favorite 3 countries, and 3 favorite least (and why).
Do you think you will ever settle down, own property, and have a family?

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