Ask YC: Where I went wrong?

It took some time to settle in US and then my brain started thinking again about how to become my own boss and to earn more money. So I joined few friends who already had idea but that didn't work well. I was last one to join that group so i didn't had much say so i just stopped working on that(Try 2).

So, I started working on my idea to create website with lyrics of all hindi songs in @Year 2000 (Try 3). That didn't go far because in part time it was too much work to do that and i didn't had any clue about whats VC and how to get funding.

So, I started working with friend on another idea about how to implement automated reminder system so that Dr. assistant doesn't have to make phone calls to remind patients ( Try 4). That didn't go far because I knew one Dr and he didn't show much interest and I didn't know how to find person who can help us in marketing my/our skills.

So, I started working with another friend to brainstorm idea about how to make paper view possible in small motels ( create a software and allow people from different rooms to select picture from available pictures - it is available in big motel/hotel but not in small motel ). At the end of analysis we found that it is not something we can do in part time without much funding( Try 5).

In meantime I started doing some work for startup which later got bought by big company but I opted out to join that startup fulltime so, i didn't get much money.

During that time I learn about value of Content Management System and found that there is a big market for that kind of software. We thought to use one open source software and then customize that software for different company but again ... who will market our skills for us ??? ( Try 6 )

So, I was back to my brainstorming session and my friend - came up with idea to invest in windmills which is alternate and growing trends to produce electricity. We found that investment is more and ROI is not as much as what software startup can provide ( Try 7??? )

Now I have applied to YC with one idea which is also seems not very good based on current market trends ( Try 8??? ) so we already have another idea ready to start working in short time - in case we decide not to waste more time on Try 8 ( if we don't get selected by YC or if YC selects us and doesn't like our idea)....

Anyway - where I am going wrong ??

To me

A. Part-time doesn't work B Need to find marketing person who can sell our skills

What else went wrong?? Don't worry..u can tell me whatever u think...i need good feedback so that next one doesn't stay in try zone but i wanna make that success...

The missing answer to this is the thing you're doing wrong.

You! In a startup, you do everything. If you aren't willing and able (or willing to become able through self-education or taking classes), then you shouldn't be in a startup...or you need to partner with a person who is capable of and willing to do the things you can't or won't do.

It's that simple. You have to build a team that answers every need in a business--and those needs are many. Some things can be removed from your plate with money, if you have some money. Some things can be put off until you have money. But some things, like getting customers, are absolutely vital. If you can't make something and get it into the hands of people that want it, you haven't done your job.

Also, you seem to like picking business ideas where you have no history and where having a history could make you far more successful in a shorter time. I once knew some folks who started a company that did water table surveys for city and state governments and they built an interesting business with two guys and a few contractors and no money up front. How did they get into something like that? Interestingly, they came in sideways...they had been in the oil and gas industry as drilling site managers (e.g. a non-technical management field), and many of the same geophysicists they had worked with in that industry worked in the water table business, as well. They had the in they needed to bump them into a multi-million dollar business without needing years to build a reputation (they had spent the years building a reputation working on oil platforms and in deserts and other crappy places).

If you want to be in windmills, you ought to work in the alternative energy industry...it'll teach you what those customers want, how it is currently delivered, and give you some ideas for making it better.

The thing about most companies that YC deals with, is that they are picking a problem that's new enough to have no established players, and requires very little money to start. That's a model that anyone in your shoes ought to consider, regardless of YC involvement.

Windmills aint it. CMS aint it (though some niche markets in that area might be). Lyrics to hindi songs...if you need VC funding for that, you're not thinking about the problem in the right way...that's just not a VC kind of business.

Another problem I'm seeing is: You need an idea that you can commit to. Find something you really believe in, and do it (or join the team that is doing it). It sounds like Try 8 is still-born already. When you start using phrases like "waste more time on", then you can be pretty sure you have an idea you don't believe in. If you don't believe in it, how the hell do you think you're going to convince customers and investors to believe in it?

YMMV. If I spent 2 years on every potentially good startup idea that came along I'd be 260 by now. Once you're flying, sure, give it a couple of years.

I think at the heart of every entrepreneur is a contrarian. I know that I'm just the type of person that if everybody else went left, I'd go right.

I don't see a conflict between failing fast and going deep. That's because when I'm in the mode to qualify the work (before I spend 8 weeks on it), I try to scope it down. Am I getting into six months of development effort? If so, is that because I want to make my technology hard to reproduce? Or is it just feature bloat -- I'm putting the kitchen sink in. I know now that I'm failing fast (giving it 4-12 weeks once approved) with small timeboxes, I'm seeing a lot more progress. Chase the users, right?

I don't think I'd go back to long timeboxes again, although I might very well chop off some really gnarly problems and chew on them a little bit at a time :)