Ask HN: Founders, what's your lifestyle like?

I'm also an undergrad and what I largely find is that it would be easier to be in an LDR with regards to your workload because you don't have as many daily "commitments" if you want to call them that, i.e. you're not trying to balance your projects with going out to eat a few times a week. The expectation is that you're not going to be seeing each other all the time, so theoretically you would have more time to spend on your work. I'd be interested to hear why you've found the opposite to be true (aside from CS, I think my true passion is relationships ;-) ). Now, give me a non-LDR relationship any day and I'll find a way to make time.

I have found that at about $30K a month in spending money, is more money than I need, even in the most expensive cities (as long as I’m hanging out with normal people with normal jobs and don’t do anything to crazy that month).

Currently, I live between Aspen, CO and San Juan, PR. I live in Aspen, because it is my favorite place in the world. There are so many amazing outdoor activities and the girls there are the best in the world (for me, I'm kind-of and extreme sports person and there are a lot of girls like that up there). The party scene is hard to beat up in Aspen, in both the summer and the winter.

Mostly though, I dirt bike all summer in the mountains and ski and snowmobile all winter.

I just recently moved to Puerto Rico for a percentage of the year for the great tax benefits of living here. So far it has been really good. I live in Old San Juan, which is somewhat like living in the Mission in SF. Dirty, grimy, hispstery and fun.

I walk or get driven everywhere I go. I don't like driving at all and don't really need to either place I live. I am in walking distance to 20 great bars and restaurants in both places.

I try to work every weekday from 8am-4pm EST no matter what timezone I’m in. That doesn’t always happen, but the more I work, the better, more stable and more profitable my business gets.

What I have found to be most important, is to make sure that I get up and get emails out early, so that no matter what is really going on in my life, it signals to everyone who interacts with my business that, I’m up early and working hard every day, which is often the case anyway.

However, for example, on Friday me my employee and a girl from down here, took the day off and had an awesome drunken brunch on the beach.

My number one employee and best friend, lives and travels around with me. We are an awesome team together and get shit done in all parts of our lives. We eat out every meal and I literally pay for everything for him when we are together. It feels a lot like he is my kid in a lot of ways, lol.

I’ve had girlfriends throughout the years, but almost every one of them has been unemployed or working on something like acting or trying to start a business. It is really hard for me to date someone with a 9-5, I think because my lifestyle is so flexible (I also require a lot of attention). My last girlfriend was a consultant and worked at home, which was the best set up so far. We would just work next to each other from each others apartments.

It took a good amount of time to get here. I’ve been founding companies for about 6-7 years. This is my third entity. Back in the day I was living on the floor in the ghetto of Berkeley, CA without an extra dime to spend on anything other than Ramen.

I’m looking to the future right now. Hoping to grow my business, save some money, spend a lot of money and have a lot of fun.

My next big plan, is to get a harem of girls to simultaneously be my girlfriends and travel with me between Aspen, Puerto Rico and the rest of the world. I’ve been working on it, getting apartments set up in both places that will work for this. Also, I’ve been looking for super smart, super hot girls who would be down for this.

So far, you’d be surprised at the reactions of most of the girls who I tell my plan to. Very few have been negative about it. Most have been at minimum supportive and they think it is cool.

I know it is a ridiculous “goal” for the future, but there are no real rules and boundaries in my life and I am going to do my best to take full advantage of this one awesome life :)

So far I think I’m on a good track.

It pays pretty well--even though I'm nowhere near charging what I've been told would be the going rate for my skill set--well enough that my wife and I took three camping trips and three international trips last year, and took the entire December holiday season off.

I don't own a car anymore; we are a one-car household now. Well, I do own one, but it hasn't ran for three months now and I'm probably just going to donate it. I exclusively work remotely. I'll occasionally walk to a coffee shop or co-working space (I live just outside of DC in the Old Town district of Alexandria). It's kind of lonely, but it's a hell of a lot better than having a boss.

The rest of the time, I (try to) make things that interest me and try to develop them into salable products. But, I'm having some issues with self-doubt. I've had tons of side projects over the years and none of them have led to anything, mostly because I've never managed to put any of them up for sale, because I believed they weren't good enough to sell, because I tend to focus on big chunks of interesting, technical work rather than the long-tail of chore issues, both technical and non-technical.

But finally, after 10 years, I got one project up and running on its own site with a "buy" button. Nobody has bought it, and I still don't really feel like it's worth buying, but at least I've gotten over that one particular hangup.

I'm hoping I can just keep whittling away at the hangups and skill deficiencies, one by one, until I've got something with all the right parts and all the right moves. I'd just like to know how close I am, though.