When my startup last year did terribly, I felt like crap. While it wasn't really a surprise (I kinda knew it was going to happen), it was a pretty painful experience.
Having said that, it's nothing compared to what I feel now. I sincerely, truly believed that my current startup had potential to grow but I lost the one chance I had. After failing our startup last year, we picked up on advice from HN- we started over. We finally found something we truly believed in and created our first iPhone App after 6 months. Given that we didn't have any programming or design experience, we worked like hell to really make up for all the areas we were lacking in. Were barely surviving by (we had left our jobs since the last failed startup) and working nonstop because this was THE idea we believed in.
One of the startup advice that I hear most often is to create a product that solves a problem of your own (37signals) because there's bound to be people like you who have the same problem. During our last startup, we sacrificed all the time we had with friends, family, and ignored our relationships for the most part. It was miserable and lonely but we were naive and still dreaming of get rich quick schemes. We decided to finally create Grooovy after months of brainstorming ideas and really felt a connection with it. Grooovy (http://www.grooovy.me) was designed to be a social meetup app for iphone that allowed users to meet over drinks, food or a snack within 75 miles of their current location. That was the key- it would really tackle the problem of not being able to meet people and just socialize especially when you're working odd hours and unable to meet anyone new outside of school or work. We wouldn't have to feel lonely!
We asked everyone we knew, even tried to find complete strangers to get an honest opinion. People were excited, we criticized ourselves harshly and improved on all the feedback/suggestions we got. When we were finally close to launching, we ran a series of beta tests which passed with flying colors. Everyone who had a chance to use it (Thank you again) thought it was a very valid and new way of socializing. It would be something new, a networking tool used for platonic relationships and not just dating. We spent extra time revising, bug testing, fixing whatever we could to the best of our abilities.
But then geotargeting happened. When we launched, we had about 3,xxx downloads starting the first few days- everything looked good. What we didn't expect was how far each user be from one another. A limit of 75miles is nothing when you're selling an app to the entire United States. We immediately got 2 reviews and a ton of feedback telling us that our idea was worth 5 stars but the app didn't work! The reason why it didn't work was because nobody was close to one another to see each other's events! This was a terrible mistake that we should've caught on. By the time that we launched a new revised update and let users know how many people were in their current area and fix what we needed, our app rank had plummeted to the 799th place under social networking. I'm still getting emails occasionally asking me when the app would be fixed, and it's ridiculous that I have to tell them that the App is working but there's not not enough people in their area!
At this point, I don't see much hope for recovery- We're at the end of our string and don't know what else we can do. I really needed to rant because this was something I had truly believed it, I truly worked hard for and believed that it wasn't just something stupid I created again on a whim. We tried to follow every piece of advice we were given, learned to be humble, continued to believe in ourselves but feel like all is useless now because we can't geotarget specific cities with the iphone like SF Bay Area or San Diego!
Edit: Sorry for the long rant, just had to let out some anger. Thank you.
With startups, it's never over. That's a good thing and a bad thing! It's bad because you never really know when to quit, and there's always something else to do. It's good because there's always another chance.
Also, I've been thinking about this "solve your own problem" and "build the dream" kind of thinking for a while. I used to be a BIG supporter of this, but I'm not so sure any more. If you look at good investors, they have learned to separate what makes them excited from what the right investing decision is. I think startup founders should be a little more like this: sitting back dispassionately determining where to invest their time and energy. This is probably much more practical than trying to find the idea that makes them the most excited. Build the right thing, the right way, get traction -- you'll get excited. Trust me. Build something that turns you on, you could be in for a LONG slog of self-abuse. Startups are hard enough as it is -- for me, at least, tying my emotional self-worth closely into all that work is a really bad thing to do.
Odds are you will fail. Any amount of fanciful thinking is not going to change that. So, when it happens, it shouldn't be the end of the world. Instead, you should be emotionally in a position where you go, "Interesting! These 7 things worked. These 2 did not. What can I take from this and move forward? New idea? Change brands? Pivot? Etc." Being wrapped up in chasing "the one" only makes this kind of self-analysis extraordinarily more difficult. At least it does for me.