
Real Lifestyle Design
We are kicking off a new post series today, the Expat Entrepreneur Life: the real Lifestyle Design. These are the lives of entrepreneur who have decided to start or run their business abroad. Every Friday, you will step into their extraordinary lives, their adventures overseas and how they manage to run a profitable business in the most interesting environments.
Our first real lifestyle designer is Robert Dempsey who when he is not building online marketing strategies for his clients can be found riding elephants with his family.
Who are you and what do you do?
I’m Robert Dempsey, the CEO & Founder of Dempsey Marketing, a marketing firm specializing in direct response social media marketing. We help our clients attract and convert
their ideal customers. And by “we” I mean mainly myself and a network of partners, though we’re looking at starting to hire some folks. I’m also the producer of The New Social SEO Podcast (available in iTunes) and the Editor In Chief of Dempsey Marketing Magazine – an eMagazine dedicated to enhancing and celebrating the lives entrepreneurs, exclusively on the iPad.
Why did you move abroad?
My wife Kookkai is from Thailand and we wanted our young daughter to spend time with the Thai side of the family, learn Thai, and experience Thai culture. In addition Kookkai teaches Thai cooking classes in the U.S., so she’s learning more regional cuisines so she can expand her classes when(ever) we return to the U.S..
Also I can work from anywhere with an Internet connection so why not move abroad?
What are some the challenges running your business in Thailand?
I’ve been working virtually for more than 8 years, however the one challenge with that is not being able to meet clients and others in person. In-person communication is the best. Video is a close second with audio being third. Text-based communications can be taken out of context so it’s lowest on the totem pole.
Having said that online marketing is what I do, and if I wasn’t able to do it for myself I’d be out of business.
Aside from that the biggest challenge is time management and knowing what and when to delegate work to a contractor. I have very high standards of work and while it’ll sound bad, finding people that meet those standards is difficult. I find it easier though to work with other entrepreneurs that are highly driven to get a ton of stuff done. Those types of people typically deliver every time.
Which advice would you give someone who wants to run a business abroad?
Focus on building a massive online network of contacts. Use Twitter, Facebook, LinkedIn, Google+, niche forums and more. And I don’t mean a network of potential customers. There are two groups of people you need to build up around your business:
- Potential customers – a very small percentage
- People who will help spread your content and point to you as an authority – an enormous percentage, like 95%+
Also focus heavily on publishing content. The #1 way to build up the two groups of people I just mentioned is to publish content on an ongoing basis. And never, ever stop.

Which part of your life abroad do you enjoy most?
Experiencing another culture with my family is awesome. There is so much we can learn from other people, and the more we can learn the better our work will be, especially in marketing.
Also being in Thailand the exchange rate is awesome, so we have a very nice condo near a mountain with quick access to the city. Try that in the U.S. – not as easy, but achievable.
So far in Thailand we’ve seen monkey shows, ridden elephants in the jungle, played with tiger cubs, and much more. We also have access to other fantastic Asian countries. I’m a huge fan of Asia in general and the people. So much culture to learn about, so little time.
Hi I'm a coach who believes life is an adventure, and entrepreneurs need to cultivate an adventure mindset to succeed.



{ 12 comments… read them below or add one }
Robert, it’s a pleasure to have you here and as you know I have always been a big fan of your work ethic (as Gini mentioned) and that great talent you have to connect with people.
I loved the fact that you shared your story here, and how cool are those elephant!
Thanks for having me share the story John. And you and your family have an open invitation to come to Thailand. We’ll ride elephants too
The photos are the best part of this! Super cool!
You know what Rob left out? He works the same hours as his clients. For instance, I talked to him this afternoon, but it was 1:30 in the morning for him. I think that takes a certain discipline to be able to do that, especially if you’re going to work with people in your native country.
It was great chatting with you Gini, and on Twitter no less! We continue to see your social media savvy and knowing my love of Twitter.
You bring up an excellent point. I do all of my client calls and interviews at night time. It can make for some very long hours but totally worth it. If I was in the US I’d just be doing more work at night and talking with clients during the day.
Either way I have enough coffee to take me through!
And speaking of getting a lot done, you’re a bit of a machine yourself lady! You get a lot done.
You are my hero. #thatisall
Whoa! Tiger cubs! I’ve always wondered…
Sounds like a great way to be. When I think about how technology has advanced to the point we can drop someone just about anywhere on the planet and they can stay just as connected as they would be across town, I can’t help but wonder why it’s still so prevalent for us to live where we work (or have such focused business models).
Some day, I’m gonna do something like this. Start small, scale. That’s the plan.
Thanks for sharing (and the introduction).
I know many a manager that is afraid that if they allow their employees to work from home then they won’t work at all. As for we self-employed business owners, we know different. However it really depends on the business and your clients. This is my second business that I’ve been 100% “virtual” and talk with my clients (all over the globe) via Skype and email.
If your clients are cool, then you can be completely mobile.
Good read and always heart-warming to know the stories, trials and tribulations of other expats. I’ve just recently met Robert on G+…I think via you, John and he’s good people.
Liked the advice to be heavy on content and never stop… Good weekend John and Robert.
Hey Jacob great to see you here. I’m supposing that your flight was good. Am I remembering correctly?
Already flown home mentally, but still waiting on wife’s visa to complete. Never visited Thailand (unfortunately) after all my years on this side of the globe, but was a great view via this post…hope you guys are enjoying yourselves.
This is a lovely interview and I think that Robert is a great guy. It must have been quite daunting as well as scary to move abroad but he has and seems to be very successful.
Meeting someone is, indeed, the most preferable method of communication – luckily there is skype.
I wish you all the best in your endeavors, Robert!
Look forward to the next post, John
Thanks Gabriella I appreciate that. I’m fortunate in that my wife is from here so it made the move much easier. Outside of that I’d probably be lost.
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