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Awesome post! I can relate to a lot of what you are saying. Start With Why is one of the best business books I have ever read, really makes you realize why a lot of companies fail. I’ve even dropped iGoogle and just switched to core blogs on Google Reader (mobile is better). It is much more productive.

I haven’t read Hackers and Painters yet, let me know how it is, it’s on the next list to order.

Keep up the good work!

This post was mentioned on Twitter by theReviewGuy: A failed entrepreneur: a thorough look at my past, a necessary preparation to look into the future http://bit.ly/dyjJsx...

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However, some could argue that taking the 2nd path, will almost guarentee you will fail. What I mean by this is that, the lack of time you will have available to work on the side start up (outside of your job) means that things will potentially move slowly, a unique idea you release may be copied for a competitor within weeks. Not to mention that it relies on you sacrificing your life completely, you work all day, then you go home and work all night… then you wake up tired the next day. Repeat. The disadvantage of this is that you’re going to wear yourself out and perhaps end up making more cut throat decisions / having a nervous breakdown. I know running a start up is not an easy business, bootstrapped or not, but having to sacrifice time to keep fit or see friends, to run your start up in the evenings is a potential ‘life fail’ – I almost wonder whether this is why in your tale above, you seem so bitter about everything.

On the plus side, working as a bootstrapped company you don’t rely on the income, so even if you only make a small amount of money, it’s an extra piece of income ontop of your normal salary and you can potentially offset any ‘business costs’ against your overall wage to reduce risk and costs.

The only problem is, that at some point (in theory) your start up will grow to a certain size, where it needs better servers, more staff and your full time. This is where finding a partner and getting funding from the start is helpful.

Potentially bootstrapping could kill a really good idea which grows fast overnight. By the time you decide you need to expand and get funding, the competition has tasted the idea and executed it better (bigger servers / more staff etc).

This is why, as stated above – I have a list of ideas, some so easy to implement I could get them online within a day and some more complex that’ll take a long time to get going. My plan is to start bootstrapping the easy and simple ideas, allowing them to gain traction – this may be enough to earn me a nice side income, this may get aquired for a small amount allowing me to fund future projects… however, the biggest thing this should do is give me a launch pad to go from and prove I’m able to execute an idea successfully – which should help when it comes to funding.

Then once this is all complete, my aim is to perhaps take some of the bigger ideas, find a partner and then go for funding (around March 2011), preferably Y Combinator (as I think the mentoring / networking is worth more than the money it gives), hopefully aim for around $100,000 funding to gain a start up visa and then see what happens.

Out of interest, from your experience, what sort of hosting have you used in the past for your ideas? Is a modern day VPS from a hosting company enough? is it worth buying your own servers and going for co-location in a data centre or is a stack of dedicated servers required to have a proper stab.

Apart from my own time, hosting is currently one of the greatest costs that stand in the way of getting to where I want to be.

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A very interesting read. It’s good to see the story from the ‘unseen’ side of start ups. Obviously everyone only hears and reads about the successes, it’s interesting to read about someone who’s come close but not quite got there.

I recently had a wake up call a bit like you, I’m an asp.net developer in a microsoft gold partnered company – it’s an ok life, it pays the bills, but ultimately doesn’t excite me. I’ve always been a high achiever, being top in class through college and university. I also have a very active mind with constant idea’s, but generally a lack of money / time (while bootstrapping) to try them all out properly.

About a year ago, I read about someone I was at school with, in the same class with me. He had gone on to start a company through Y Combinator, got funding and sold the company for millions. It made me feel sick, I felt that, it should’ve been me – that’s what my life should be, not me wasting years in a boring office job making software I’m not passionate about.

This is why, in 2010 I have decided it’s the time for change for myself too. I plan to launch a start up and see where it goes, however reading your tale makes me realise how realistic failure is.

Interestingly, the start up idea you have, sounds very similar to one which I also have on my list (I have a note pad with loads of ideas written in), all to do with helping people reach their goals / self improvement. I have also figured out a way to make it ‘unique’, attract a social aspect and most importantly of all generate income from the user driven content other than just ‘eye balls’.

However, I’m not sure if I’m ready to take the plunge right now to go dive fully in and quit my job.

My plan of action was the following:

While working, boot strap my new company:
– The company would start by releasing smaller products, which have no direct business model, but almost guarenteed success in gaining a following. I don’t want to divulge in too many details, but this would provide to assets. One it would provide a general ’small’ income off the advert due to traffic, but also it would provide a great launch pad and following for future products to be launched from.
– Once this phase was complete, I would look at moving into some of my bigger ideas, e.g. the ‘Goal / Self improvement one’ listed above, plus some of the other ones. I would aim to approach Y combinator, or many of the smaller funding companies that now exist to get basic funding, using my success on the previous platfrom to help gain trust that it can be done. With Y Combinator or any startup, they generally suggest having at least 2 founders, so at this point I would be looking for someone, probably with business / marketting knowledge (bonus if they are a good designer too). I have knowledge of marketting and business too, but my main expertise is in coding.
– The final aim would be to turn each of these ideas into a profitable commodity. This means, even if they were never aquired, I would make money and not need to go work in a boring office job. Of course, with profit coming in, other ideas could be explored, staff hired and it would only be a matter of time until a bigger fish offers to aquire the whole network.

- At this point, I would go buy a house, a nice car, and sit thinking of the next big idea.

Regards.

@PaulJoslin

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