Being ready for this may require you to improve the robustness of your service.

Support - have someone monitor it

General office phone - employ an answering service. A human should answer phones for business image reasons.

Infrastructure - design it right. Assume that fiber to your datacenter can get cut any second. Now what? Provision remote storage in case local drive dies. Boot the OS into RAM so if the local drive dies it won't affect your server. I am going a step further and configuring everything to boot from PXE using iPXE. The goal should be that a monitoring script that hasn't received a heartbeat can reset your infrastructure. Payments - have multiple payment methods defined for your critical services, prepayment may help.

As long as the infrastructure can reset itself and your phones are answered and support is handled, enjoy yourself.

This is how my processes are setup, but my product is relatively simple so support is usually not an issue. However, I rely on so many APIs that getting all that robust enough for me to be confident to take a break was a significant challenge.

it seems your vostimonial.com service has been hacked by a hacker from Bangladesh though... that or your HN profile page is outdated.

I've been on both sides of this. I was hired to cover for 1 man dev shop for 2 weeks. I was briefed, given necessary details, introduced to client(s) and just sort of jumped in. Handed it all back over when he returned. I think it went pretty well, it seemed like an immense amount of trust on his part. I am not sure I would have been comfortable if the roles were reversed.

As for taking vacations with my startup... I just left. But my startup is mostly automated and doesn't require much direct input from me. If I stop working or disappear for a bit, nothing bad should happen other than a server crash (which hopefully my setup will recover from). I won't get any marketing, or new features, but I am just providing an informational site. So really, it tends to just stagnate if I'm not working on it, but not decline.

I've been a solo founder for 10 years. Not only do I work only a couple of hours each day, I take lots of vacations. I've traveled for 40+ days at a time without problems.

However, when you say "remote" places, do you mean places with absolutely no internet access? If that's the case, you're going to have a tougher time. But there are really few places in the world that don't have internet access.

I recommend you read a book called "Work the System". It will teach you step by step how to create processes and train people to run aspects of your business that either you don't want to do yourself, or can't do due to travelling, etc.

http://www.workthesystem.com/

If it's a true business (not a hobby), you'll be able to justify contracting/employing someone to run your systems and serve customers. But checking-out for an entire month is a recipe for disaster.

The longest I have been able to be "on vacation" has been 3 days straight in the last 12 years. And on Day 4 I spend half of it on catchup work.

That is why you need a team.

Not every year.

If that's your main problem, don't start.

I am not saying this is my main problem (it is not). It is a question of logistics and I wonder how other people in a similar situation/lifestyle have solved it. If you want to imply that taking time off even as a founder is a sign of lacking passion or commitment: my personal experience is that people who don't recreate tend to blow things up really bad in the long run.

"people who don't recreate tend to blow things up really bad in the long run."

Including themselves.

This sounds like a pretty legitimate, forward-thinking question. I am interested in other people's responses.