Even if you just intend to visit and and up doing some work you'll get in deep trouble, but if you lie about it from the start it'll be much worse.
And they do sometimes check.
A tourist visa and a work visa are not interchangeable.
You can work for your outside-the-US employer, you can collaborate with US customers, suppliers, partners, you can train them,you can sell, demonstrate and install products. About the only thing you can't do is work for a US company.
Picture if he was an engineer from Rolls Royce aero engines going to Boeing - everything that engineer might need to do you can do on a visa waiver.
I wouldn't touch the topic of Bitcoin with a 10 foot pole around strangers, let alone people with the authority to deport me. I still can't explain it to my friends in a way without making it sound suspicious.
(As an American, I hate crossing the UK border just as much as crossing the US border. What's the point of being in the EU if you aren't going to act like it? :)
I've been told my visa wasn't valid because there should be a blue copy instead of a red copy (he was wrong - as the INS eventually told me) I have been told that I'm only allowed so many visa waiver visits (wrong), that I can't visit my companies US office under visa waiver (wrong)
It's as if every time an airbus landed at a US airport it was upto the baggage handler to decide if it met FAA requirements
http://www.schneier.com/blog/archives/2009/07/laptop_securit...
1) You are there on a holiday. Telling them you are self employed and going to work in an office you are renting there is only asking for trouble. It confuses the hell out of them. You think where you do the work from doesn't matter, they think you need a visa. You lose.
2) If you are going for a conference, print the badge off before your flight and have it with you.
3) Email or upload all your files to dropbox/some server in a TrueCrypt container, and wipe all devices you will be crossing with, including your phone. What do you need them searching through your stuff for? Who knows what they will do with it. It's just asking for it.