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at what point do you know if your startup idea is bad or has potential?

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The first crack at the idea may be wrong, but you just keep going.

Test the idea out with a lot of people, get their feedback, and then end up with something that they would use.
 
The best entrepreneurship book I've read is "Anything You Want" by Derek Sivers. It's really simplistic and gets to the core of a lot of ideas when it comes to starting a business.

One thing you have to be careful of is that there is a general tendency to want to tear you down, even if it isn't intentional. People capable of starting their own business often do not because they are cynical, able to identify every little thing that may go wrong. They bring the same attitude to your idea and aggressively attack it. Their intention may be good but they don't understand that a business plan is something of a joke, most of it will not go according to plan and you're going to have to improvise a lot along the way.

I talked to a bookstore owner today that told me she is $50,000 in debt, lost money for 3 years straight, and considering quitting the business. That's when you know it might be time to fail. If you have the passion about your idea then 2 months before it starts is not the right time to quit.

At the same time, back to the Sivers book, he makes a good point to wait until you have an idea that sells itself rather than something you have to try to force upon people. So I'd expand it beyond one person and see others' reactions, specifically potential customers.
 
You might want to take his negative input & see if there are any positives to extract from it. I'm a person of details & ask tons of questions with anything that's new to me. So it might make sense to break down his feedback into parts. Some you may like, some you may not, but at least you'll have a more thorough understanding of what he meant.

From that, as mentioned above, ask for additional feedback / input. Once you have input from a few friends / family members, share the first person's feedback & see if anyone else shares his opinions. Then you really start breaking everything down, one part at a time.

Once you have this information, you can really start brainstorming & see where the parts start to land. Maybe they land in your favor, maybe not, but at least you'll know & you won't be second guessing yourself.
 
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