They gambled and lost. As long as you weren't funneling the money into your own account or fraudulently representing yourself you have absolutely nothing to feel guilty about.

I see where brianwawok is coming from. You shouldn't feel an overwhelming sense of guilt, but you also still let people down.

Also keep in mind that most entrepreneurs raise some very early money from individuals ("friends and family") who don't have portfolios with dozens of companies.

> but you also still let people down

This isn't true in my opinion. (Unless you didn't do what you said you'd do).

Quite. It seems rather misplaced guilt if anything; the investors presumably saw enough of an upside across all of their investments to make up for the majority that failed. Yourself and your employees, not so much.

What if your seed money came from your grandparents and family. Does putting a face you know to the source of the lost money change how you feel?

This is why you should think really, really hard about taking friends and family money. You might be able to handle the mental complexities of it, but I realized I couldn't.

It's sociopathic to not feel guilty that you accidentally made rich people slightly less rich?

Not because you made them slightly less rich, but because you did not help them make money when they trusted you with their money. But then i wouldn't call someone sociopath if they don't feel any guilt. After all we are not all wired the same way.

But if it was an accident, there is no need to feel guilty.

If you accidentally ran over a kid in the road would you feel guilt?

If it was truly and accident and you were watching the road and going the speed limit.. sure - don't become an alcoholic over it. But I sure would feel guilty!!!!

Now losing an investors money is a smaller offense to killing a kid, but it is still a "negative" event. Not sure accident or not matters, feeling guilt is natural. We need to acknowledge our feelings and move past them, not deny that they exist.

I think guilt is a first step to reflection. Feel guilty. Reflect how you can do better next time. Then move on and do better next time. I think you should do this in either case (accidentally ran over a kid, or failed a startup)

Its better not to feel bad about it. It allows you to fail faster and be more honest with investors and employees. The market pays for exploration. If you weren't a winner, you still did society the service of exploring that area.