I failed my 3 business (in different domains). The key reasons:

Thank you for sharing. I can totally relate with #2 and #7. I know I shouldn't be doing them, but still I end up adding a lot of features before validating the idea.

What do you mean by "not confident enough" in #4?

I agree with most of them. One I would add is not getting on with it and planning it too much instead of getting going and learning as you go. There is a story that there were two men who sold cars. One man took a month practising his sales pitches, learning the contract small prints, checking the vehicles were safe, printing up marketing materials to hand out, studying retail law to deal with faults or warranties. The other guy rolled up his sleeves, walked out on to the forecourt and went up to a stranger asking if he would like to buy a car. At the end of the month, the careful and planned guy had not yet started selling so had sold no cars. The other guy had sold 60 cars that month. The first guy asked, "but what happens if someone finds a fault or fails to keep up payments on a contract?" The second guy said, "I deal with it if and when it happens, in the meantime, I am selling 3 cars a day, can now hire a lawyer to deal with any problems, and buying a hot tub for the garden tonight!" The moral to the story is that you can take forever to prepare a project, add more and more features to it, worry about "what if's", worry about market researching and feedback tests and so on, but while you do that, usually at a cost to sustain you and the project, someone else is just getting on with it and making a success of it. Take an idea, spend a couple of days researching it and mapping it out and then just get on with it and launch a working version as soon as you can. Get it going and then while it is gaining traction/sales get on with polishing that turd up.

Hi Rajan, I agree with most of your points but not number 2. I think at the beginning you should try to launch a first version, which looks okay (doesnt have to be excellent) and has some of the features that are necessary to add value to the user, then all you need to focus on next is talking to users and build features even if you have 5-10 users in the first 2-3 months, that's fine, but the most important thing is to always try to get feedback and add / iterate accordingly. During that process you can try to have some presence online, FB, Instagram, Quora, PH, IH, whatever, but some presence online which would help you to get some users which could then provide you with valuable feedback. Ofcourse, some people are lucky and get tons of users at the beginning, but that's not the norm.

Thanks for sharing, Rajan. These are all good insights!

I failed my second business even before I got started. Bought the domain the very day Robinhood shut the unofficial API off.

All points nail it, awesome Rajan. I'm just a bit concerned about the fact that you never mention anything about your team here. So many businesses actually fail because of the team issues (especially if they manage to move further from the launch stage). Do you feel that your team has nothing to contribute to your business success of failure?

for me its first 2 :). Btw I am very focused on my current start up. DropUrCard ( www.dropurcard.com) try it out and let me know your feedback.