Couldn't agree more. I fell into this trap for a number of years. Once I started taking my business seriously and treating it like a job (an intense one at that), I've had far more success.
Have you ever written about this period of your life? Having a family and the time/energy/freedom to play the startup game seem so mutually exclusive to me, although I do admit that's mostly my gut speaking out of fear of aging and settling down. I'd really love to hear more about how you managed it all.
It helps not to look at it as a game. Matasano is a business, growing steadily, with a serious team and serious management. It isn't something that might pivot after some networking meetup thingy tomorrow, or if Facebook buys the wrong company next week.
I'd read a lot of 'patio11 if you're interested in this stuff too.
While we all eat shit at different tables there is no question in my mind that being an entrepreneur gives you greater flexibility and to be able to play less games that you do when you are an employee. (Or for that matter have partners).
I'm reminded of this when I do some side consulting and help people with what I am really good at. (Negotiating) I have to spend time convincing them of something that when I do the same for myself I have to convince nobody but myself. (And it's worked real well. For many years.) The amount of extra time I have to spend selling a concept (and writing emails) is a big drain.
Likewise I have a person who does some work for me on the side who holds a full time job with a big corporation doing security consulting. He does the work for me (on the side) because he enjoys the freedom he has to implement his ideas without having to convince his companies consulting clients (or his co workers) that his ideas are right. So he gets pretty much cart blanch with me to try something (and I write the check without all the red tape and effort).
This. This. A thousand times, this.
Really? That's a surprising sentiment coming from you.
Something I agree with is "someone who can play the game as an entrepreneur can also successfully play the game in a conventional career, but most 'regular' people don't play the game at all". Is this what you're talking about? Because I have to say, most of my entrepreneur friends are very different people to most of my "regular career" friends.
Pretty much this. At a cube job you work for managers, at a startup you work for VC investors.
>* Even with significant obligations, a startup failure is unlikely to result in your opportunities being limited for very long.
It depends on the obligations, I assume you mean mainly family. If you are lucky(?) you may have a spouse crazy enough to follow you down that uncertain path, but that is not the case for most people.
My point is:
* Even with significant obligations, a startup failure is unlikely to result in your opportunities being limited for very long. Yes, you'll probably end up needing a "real" job for awhile, but (a) not necessarily for very long and (b) if you crater a startup, a normal job is probably a good move anyways.
* If the only job you can secure after killing a company is as "cube rat", consider whether your prospects as an entrepreneur are really all that much better. People like to believe that entrepreneurship is something totally different than executing a conventional career, but that's mostly a myth.