How I'm Bootstrapping a Startup While Raising Three Kids

> I'd like to point out that unlike Calacanis I don't feel comfortable suggesting to people what they can and can't do as I believe it all really depends on the individual and the context in which they're operating.

That's a key insight right there, most people will go around and tell others what they can not do based on the experience of what they themselves can or can't do, and then they automatically extrapolate to the rest of the world. The reverse also holds true.

Whatever works for you is something you will only know by trying and doing, nobody can tell you what you can or can not do.

> Taking the kids to the gym is probably where I gain the most leverage of the day because it's a kill three birds with one stone, triple-jump move.

Very clever!

> Also, you know all the time that most employees and on-site contractors spend in meetings or other such unproductive organizational activities, well I engage in none of that.

Haha, score one for all the guys and girls that work from home. I try to avoid meetings like the plague, though I do have an 'office' in an IRC chat running. It's where I gather with everybody that I work with and where you can dump questions or have a few minutes of 'watercooler' talk.

> Another thing is that we keep our expenses pretty low and don't tend not to live very extravagantly.

Another winning quote. People that freelance sometimes fall in to the trap of adjusting their lifestyle upwards when the money is coming in quickly, but can't scale back when it does not. The safe approach is to stay low to the ground and be frugal all the time.

Once your saving account is nice and fat and you've been consistently performing at a certain level you could consider raising your monthly allowance (a bit!), if you feel the need to do so. For myself, I keep our personal expenses to an absolute minimum.

> Another circumstance that allows me to pursue a startup is that my wife and I have figured out a very clear division of labor and separation of concerns.

Clarity and openness are another key element in both a relationship and running a business. Having things clear is going to make sure there are no underwater time-bombs too.

What a super article, bookmarked and I'll re-read it again in a couple of days, lots of it applies to my situation directly and I'll try to get as much mileage from it as I can squeeze out of there.

One key insight that is not spelled out here is that you seem to be living a very regular life, and I suspect that that structure helps you to optimize what you get out of a day.

Thank you very much for writing this all up, (you even found time for that!), it is certainly inspiring.

A friend of mine started VC-backed company when his 3 kids were 2-4 years of age. That was several years ago and since then the company has grown to 400+ employees, millions of paying customers and went public with the market cap of over 500 mil. Call it an "old-school" start-up if you will.

His HowTo is nannies. That freed up lots of time without making him feel like he was neglecting or taking away from his children.

YMMV however, because many people simply do not accept the very idea of letting strangers care for children of a very young age (them being the formative years of the personality and for other reasons).

I am currently bootstrapping a startup (http://www.wellhubstudios.com) while working at another startup and have a 1 year old with another child on the way. Couple tips that I picked up along the way:

1. Patience. Building a company is a time-intensive process that can be frustrating when family is demanding a lot of your time. Just focus on the goal and slowly pick away at your giant todo list for launch.

2. Its Good enough. Sometimes it seems like things are not moving forward or moving forward at a glacial pace. At these times I try to switch gears and say to myself "whats here is good enough for V1".

3. Time Management. I work 8-5 at my job. Come home and hang out with the family from 5-10. Then work on my startup from 10-1 pretty much every night. This takes both discipline and the ability to handle being a bit sleepy.

I was horribly inefficient when just getting out of college (I'm 26, 4 years out). I largely owe my improvement of work-life balance/awareness to my better-half; I think I'd still be struggling with it if I were single.

This is a generalization, but from what I can see, the same thing happens in grad-school students as in startups. People that are coming directly out of undergrad have less of a sense of work-life balance and how important and helpful it can be to your productivity and happiness.

this is a great post that adds a lot of great tips to the discussion for parents. it really moves the discussion forward. Thanks for writing it.

I agree that commutes, meetings and starbucks runs are out of the question for folks with limited time to dedicate to their startup.

I see people doing two 20 minute Starbucks runs a day and I'm like how can they waste 40 minutes a day/200 minutes a week/$50 a week on Starbucks.... then i realize they don't have to get home by 7:30 to put their kids to bed and wake up at 6am to feed them breakfast.

I'm uber efficient these days.... even my email list was designed to make my life more efficient.

I don't need to go to networking events, read blogs, recruit developers, do PR, do SEO or do any kind of social media or marketing.

I simply pull my thoughts together in 30-60 minutes and hit the send button. 20k+ folks get it in their email box, 250k get it on the web as folks discuss it and forward it around and 1,000+ responses wind up in my inbox.

Many of the responses I get are from entrepreneurs who want:

a) me to angel invest (so i get deal flow!) b) developers from outside of the major cities who want to break in to the internet industry ("well hello! please meet my Director of Technology who will fly you in for a recruiting/cult meeting") c) investors who want to hear about ThisWeekIn.com, LAUNCH.IS or Mahalo. d) press who want to re-run the piece e) partners who want to leverage Mahalo's 20m+ uniques.

Efficiency wins..... efficiency and leverage can be found anywhere--you just have to be open minded.