CEO of Argenia; Co-founder, past CEO of Agility CMS; Co-founder Inner Circle Meetups; Founder, Recall Media. Entrepreneur for life who loves helping others.
I was just in Thailand working for 2 weeks and I wouldn't worry about political issues. There are a lot of amazing places for remote work there that would support an active lifestyle.
My experience in Costa Rica last year was also excellent. I worked for 2 weeks there and didn't have issues with internet. I was in a fairly remote area as well.
SF is super expensive, but probably the best place to be for a web developer if you can afford it. You will probably get weather that dips below 10 degrees in the winter though. Wth incessant rain to boot.
Check out www.nomadlist.com for rich info on the best places in the world to work.
My wife and I are looking to do the same - from Toronto as well. Looking forward to seeing some other answers!
LOL @ Columbus Ohio ;)
I would start by calling media buying agenices. You're in NY, so no shortage of those :)
Sounds like you have experience cold calling, so maybe do the calling yourself until you gain traction with a couple of agenices. If you build good relationships and show results, you should get the same agencies coming back and buying for different clients.
You could try building relations with the big advertising agencies. They have access to huge consumer brands who are all jumping on the content bandwagon. These brands have lots of money to spend.
The agencies can provide a steady pipeline of work. They can help build your portfolio of brands while you're relatively unknown. Once you build a profile, you can start approaching the brands directly.
I would stick to companies with $10m+ in revenue. The cheapest customers are also the most demanding.
It doesn't hurt to learn the ropes on someone else's dime.
I started a web development company right out of school in 2002. The hardest part was winning business because I didn't have much of a network. If I were to do it again, I would prefer to work somewhere first for a couple of years.
However, if you can't find the right opportunity and you feel ready to start a business, then go for it! It worked out okay for me :)