What are the chances of one succeeding with moonlighting?

This is like being a one-legged man in an ass-kicking contest. (paraphrasing Charlie Munger)

Self-serving bias all over. As far as I can see, the only valid reason for working on a startup part-time is risk/cost tolerance or some obscure personal situation.

Some 'advantages':

>You can fund your own startup.

Refer pg's equity equation. I'd love to have sequoia/YC worry about my company in addition to my co-founders.

> No one is going to kick you because your took money from them for your FAILED startup. No one even cares if your startup fails

That's not necessarily an upside. I think most people can deal with personal failure a lot better than letting someone else down. This affects motivation. To quote Bezos: Jeff Bezos: I think one thing I find very motivating -- and I think this is probably a very common form of motivation or cause of motivation -- is... I love people counting on me, and so, you know, today it's so easy to be motivated, because we have millions of customers counting on us at Amazon.com. We've got thousands of investors counting on us. And we're a team of thousands of employees all counting on each other. That's fun.

>If you love coding then you can enjoy it 24/7

Try it and notice your efficiency. I'd actually recommend switching roles for your day job and night job.

Regardless, Kudos for being the one-legged man - this shit ain't easy.

"# No one is going to kick you because your took money from them for your FAILED startup. No one even cares if your startup fails"

Actually, this is not the case. Your family is going to kick you big time if you were away of them for months, for a projects that fails. They are counting on you... (at least if you are married, or you have kids, etc)

Watch out in case you signed a contract that explicitly claims ownership of all your work, regardless of "nights and weekends" spent on your startup.

Also, watch out for non-compete clauses.

Both might be de facto safe if you have a cool employer, but an investor's top interest will be the protection of the IP of the company. Things that look risky are to be avoided, and a violation of a contract is a major risk.

It really depends on what you call success. If you determine success to be getting acquired and retiring, then no I don't think moonlighting will get you to that point. However, if you determine success to be creating a side business that is profitable and has a slower, but possibly more steady growth rate, I definitely think that is possible if not probable. I have succeeded in creating a profitable side business and regardless of what others may think, I consider myself successful because of that.

It sounds as though any strategy can work as long as you're serious about it.

Actually, he overlooked one very, very good reason:

You get requirements from your daytime job.

This is so important that when I stopped moonlighting and went full time on my start-up, I kept an outside client 2 days per week. Let me explain...

One of my biggest problems has always been WHAT to build, not HOW to build it. Many successful start-ups have been the result of building what one needed oneself. I just expand "oneself" to include my parttime clients. Think you have needs? Wait til you see the long lists of needs in almost any small business. Sure, I lose a little time in the development cycle, but I more than make up for it at user acceptance time. No cycles there - I already know what they want.

If you're curious about this, I suggest following the official Joel on Software "The Business of Software" Discussion Forum.

http://discuss.joelonsoftware.com/?biz

I tend to think of it as "Hacker News for people with a mortgage".

You can pull this off if your day job contract has no IP restrictions and there are no competitors coding full time as you divide your time between the start-up and your day job.

I enjoyed the article, I think the points are well thought out.

How are you going to get the initial users for your social marketplace?