My failed bootstrapped startup: a retrospective.

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 really enjoyed reading your story. I had similar experiences with my side project as well.

In my case, I tried to take on the behemoth that is Intuit. I spent 2 years working on the same side project. In my third year, I decided to quit my job and focus on it fulltime. Six months into working on my startup I realized that I made the mistake of trying to pick a fight with Intuit since the product that I was building was too much for me to handle.

I decided to switch course and focus on niche products for the Mac App Store. Two months after my pivot, I was making a few thousand a month from my apps. I've since accepted fulltime employment and am continuing to work on my Mac Apps as they are still generating the same amount of money.

From this experience I learned its best to focus on a niche market if you are a one man band. I think your failure was because your focus was too wide. Perhaps for your next project, you should consider focusing on a niche market.

Good luck.

Best of luck on your next startup. I honestly think that in the end you just had to ask yourself if you were willing to spend the next 10 years of your life working on Beautiful Savings. If your answer is "no" then obviously, pouring more time and effort into that startup seems painful. There's no point iterating continuously on a solution for a problem that you're not dedicated to solving.

I think though once you find that idea that you're genuinely excited and passionate about, you'll find that failure only occurs when you decide to stop iterating. If a person has a solid idea and solid execution, I find it hard to believe that the end result will be graded an "F", more likely it'll be a C or D, unless you are very very unlucky. The idea is the that the next iterations bring it to an A or B.

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-oconnor-good-entrepreneur/ ↗

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?"

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!