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My failed bootstrapped startup: a retrospective.

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Re: My failed bootstrapped startup: a retrospective.

#2
These kind of posts always leave me with a mix of inspiration and discouragement.

It is awesome to read about someone like you (local developer, similar learning style, beginner entrepreneur) who actually builds something. There is a lot to be proud of for just Doing Something - even if you fail. But at the same time, I feel like I would fall into the same pitfalls that you mentioned.

I am not looking forward to doing anything related to setting up an LLC, doing sales calls, etc. I like my job and don't want to quit. I know other developers but end up working on my own stuff alone in most cases.

Thanks for sharing Aaron - I'll have to try to make it out to the next Devs With Side Projects meetup.

Re: My failed bootstrapped startup: a retrospective.

#3
Most of the time, if your startup is a side-project (IE: you have a full-time job), it won't be successful. Not to say that this is impossible.

I've found that when you are working full-time on something, your mind is in a different place. You can also move much faster.

Re: My failed bootstrapped startup: a retrospective.

#4
post #3

Most of the time, if your startup is a side-project (IE: you have a full-time job), it won't be successful. Not to say that this is impossible. I've found that when you are working full-time on something, your mind is in a different place. You can also move much faster.

So very true. I struggled with that decision a lot, but ultimately chose not to. Mostly because of the impact it would've had on our adoption.

Re: My failed bootstrapped startup: a retrospective.

#5
Sometimes, the best startups start when you are dissatisfied with your present job, have nothing else to lose, but are smart, and have a couple of ideas you think are really awesome and a game changer. Check out this TechCrunch article where one of the cofounders of DoubleClick, Kevin O'Connor talks about the attributes of an entrepreneur: http://techcrunch.com/2011/08/19/founder-stories-kevin-oconn...

He lists a few signs of a successful entrepreneur. A desire for control and the ability to challenge authority are near top of the list. A way to detect the second trait? "Have you told your boss to shove it?"

Re: My failed bootstrapped startup: a retrospective.

#6
I've been writing a similar tale of my own - with a surprisingly similar name, as a matter of fact.

It's never easy to watch something you've poured so much work into fall apart like that, so my condolences on your loss

http://lookingbackaretrospective.posterous.com

Re: My failed bootstrapped startup: a retrospective.

#7
I fought against the need to quit my job for over a year while I was working on startups on the side. It took an idea that I was wildly passionate about and a well-timed layoff to make me realize that being "all in" wasn't just a poker metaphor the already-successful used to look down on plebes like me.

That said, I'm stupidly well-placed to be working on my own idea, unpaid - I'm using the self-employment assistance program through my state's unemployment department to get UI checks without having to job hunt (I do, however, have to submit business plans and the like). I also have enough in the bank to cushion me when the government cheese runs out.

Re: My failed bootstrapped startup: a retrospective.

#8
The long and sometimes lonely path of a start up... apologies as this maybe slightly off topic.

I keep seeing stories of start ups that are a huge success, launching or died.

Where are all those companies in between? Perhaps it's a combination of not being exciting to report on and founders being busy (both of which could be related to working hard).

Anyone know of place for those between launch and dead?

Re: My failed bootstrapped startup: a retrospective.

#9
post #7

I fought against the need to quit my job for over a year while I was working on startups on the side. It took an idea that I was wildly passionate about and a well-timed layoff to make me realize that being "all in" wasn't just a poker metaphor the already-successful used to look down on plebes like me. That said, I'm stupidly well-placed to be working on my own idea, unpaid - I'm using the self-employment assistance…

What state are you in?

Re: My failed bootstrapped startup: a retrospective.

#10
post #8

The long and sometimes lonely path of a start up... apologies as this maybe slightly off topic. I keep seeing stories of start ups that are a huge success, launching or died. Where are all those companies in between? Perhaps it's a combination of not being exciting to report on and founders being busy (both of which could be related to working hard). Anyone know of place for those between launch and dead?

Anyone know of place for those between launch and dead?

In between "I'm shutting down because of lack of traction" and "I just got acquired for $20 million" I know a few people whose startups have become "lifestyle businesses". Though that term seems synonymous with failure on HN, for the people I know, it means being the boss, not having one, working from home (or Hawaii, Thailand, etc. for a few weeks at a time) instead of working in a cubicle. They're making anywhere from $150k to $240k per year, and will likely continue to earn that but not much more because the businesses don't scale easily, but they're doing what they love.

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