My failed bootstrapped startup: a retrospective.

I don't recommend anyone to quit a FT job unless startup is already generating cash flow and need more hours of your time to scale further. My last startup failed because we foolishly quit our jobs prematurely, it created pressure on us to generate income, we had to abandon bootstrapping, forced us to look for outside financing, wasted too much time trying to chase angels and VCs instead of focusing on business, made us quit 12 months before cloud backup (our target) took off.

Now, whenever someone tells me that such an such angel asking him to quit job to show commitment to startup, I tell him to tell angel to write a check for $X and then you will leave your job. Don't quit job if someone want to see that as your commitment to the cause.

Please Note: This might seem critical but I'm just pointing out three problems i.e. lack of effort, lack of measuring effort and other statistics, lack of empathy with customers.

My argument would be that without at least 2 of these 3 the OP will keep running into problems and keep blaming extrinsic meaningless things.

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Credit to the person (aaron?) for writing this. However, the lack of measured numbers is terrifying. And the disconnect with the customer perspective is just hard to fathom.

1) How much time did you spend on this? Over what period of time?

2) How much traffic did you get? How many people bought coupons? How many people went to other sites from your sites?

3) What amount of money did you spend? On what areas? What amount of money did you make? From what sources? *

You say that you didn't listen to your customers. My point would be that you didn't realize that you were making something FOR THEM and not for you.

You should consider thinking from your customers' perspective.

They really don't care about some of the things that you think are successes i.e. using hosted services and learning Ruby and the site being BEAUTIFUL because you think a site being beautiful is important to you personally.

Unless Indianapolis is 99% users of HackerNews.

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You say that you were shocked that small business owners don't track things - yet you write this post without giving any figures. Which makes a great post meaningless because we don't know what 'You had no skin in the game' means.

Did you spend 40 hours a week after doing your day job? Did you do that for 3 full years? Did you put in $100K of your own savings?

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Finally, you went into a space where you had very few competitive advantages - not the first mover, not the best product, not the most money, not the most resources, no brand recognition.

If you had tried a niche within coupons or a new area you might well have seen much better results.

Also, you don't mention anywhere how much total time and effort you spent on this which makes it difficult to know whether your lessons are worthwhile or not.

If you spent 10 hours a week for 6 months - then obviously all your 'learning' is probably useless.

If you spent 40 hours a week for 2 years - then it's very valuable stuff.

which one is it?

I think starting anything in the coupon space is difficult as it's not about the technology, it's about the sales. Groupon has an extremely simple website...it is merely a platform to display the deals: their success is essentially totally driven by the massive sales force they have at work them.

I think that technology in this space will play a greater role in the future (mobile, targeting, etc.) but for now the winners are those who sign up the most businesses and the most consumers.

I don't think the author should give up on startups entirely; it sounds like they have indeed learnt some skills and can apply those to any number of future projects. At least they have worked out this space is not for them!

All fair questions (even if your conclusions about the value of my learning are a bit bogus ;) -- the value in learning does not always depend directly on the cost paid to learn.)

I have (almost) all the numbers. I can tell you what I spent, to the dollar. I can tell you about the traffic to the site, what they did, what was successful and what wasn't. I can't tell you how much time I spent on it because it varied so drastically over the past year. It ranged from 10 hours a week to 0 hours a week. It just depended on how busy things were at work and with the fam. (EDIT: my wife tells me it was more than 10 hours a week. ;) )

The point of the post wasn't to give detailed numbers, but just to generally convey what I took away from it. Whether or not you know my numbers doesn't change what I learned. And just because I didn't mention it in the post doesn't mean I don't have it, that is a large assumption. I'm not sure how it makes the post meaningless. Perhaps you can't tell if you can trust it or not because you can't measure it? But even if there were numbers, that doesn't tell you whether you can trust it any more or less, so perhaps that's not it.

I wrote the retrospective post about the things I care about, not the things my customers cared about. You're absolutely right that almost all the stuff I listed is meaningless to my customers, and I never even mentioned it to them -- they don't care! :)

Also, I didn't go into it in the post (I was going for something shorter and readable/consumable) but I had two customers. Small businesses listing coupons, and people using the site looking for coupons. I thought about it from both perspectives every moment I worked on it. I geeked out about how I was doing it, but never lost sight of my customers. Sorry if that wasn't clear in the post.

You're also absolutely right that it was a poor choice of spaces. That was a huge lesson I learned. :)

So to summarize, take it for what you think it's worth. There's no law that says you have to read my lessons learned and apply them. But they are lessons I learned, regardless. Thx for reading!

Don't worry, I haven't given up. :) Well, I haven't given up for good... in the short term, I just can't swing work+fam+startup. For now I'll just keep working on side projects and see if any of them make any headway. ;)