This subreddit is full of stories of success. I have a few of them, but far more businesses I have tried to start failed. Here are some of the worst.

Thanks for sharing. It can be useful to do a "post-mortem" of your failures to learn lessons from them.

My Hall of Shame:

Project: Becoming a freelance web designer. I realized I didn't like dealing with clients, and I rejected even the few offers I got. Every meeting, I just had these nightmare visions of websites that never got done due to endless revisions from clients.

Lesson: You'll be happier if you can pick customers you like to serve.

Project: A blog about open-source graphics software. There are plenty of entrepreneurs who've built businesses on open-source software--WordPress themes and plugins come to mind--but I failed.

Lesson: I think the crowd I was targeting was resistant to buying anything. Go for people who actually want to buy stuff.

Project: A blog about credit cards to make money from affiliate commissions if people signed up for the credit cards. The problem? I hate debt and couldn't handle trying to get other people to add to their debt.

Lesson: Don't promote things you don't believe in.

Project: Travel website, various incarnations. Blog, podcast, YouTube videos. I was really passionate about travel, and wished I could figure out a way to monetize it.

Lesson: it's easier to get into a market where people are already getting sales and earning profits. Not try to "monetize" a passion project that was never set up to make money to begin with.

I still shake my head at how bald-faced obvious those lessons are. But I was young and thought I knew better and learned the hard way.

I think my big problem was swinging too far to the extremes of passion-but-not-profitable to profitable-but-not-a-passion. Finding the right balance was tough.

My big realization was that I was doing everything I could to avoid selling. Took me years to face up to this. I was really into creating content, but that doesn't necessarily translate into making money. I thought making something popular would automatically make it profitable.

I needed to do the grunt work of:

  • finding good markets. If there is no competition, there's probably a reason. Everyone else has failed, and you won't be the first to magically get it right.

  • discovering what customers really wanted, not trying to get them to want what I wanted, or worse, tell them what I thought they should want.

  • coming up with irresistible offers. The more you can make the customer think, "I'd be an idiot not to buy such a great deal!" the better.

  • presenting those offers with persuasive messages.

  • broadcasting those messages out via advertising.

Reading over the other comments, a recurring question was, "How do you know when to quit a project?"

It's not perfect, but one gauge that's helped me decide to quit things was this question: "Would I still be miserable even if this business succeeded?"

A lot of times, it was people problems. If I didn't like my customers, employees, vendors, etc. it was usually game over.

The work itself is also a big factor. When I dreaded if a new order came in, instead of getting excited. I'd want to get out and start over with something else.

Another thing to look at is if you are seeing some results. If there are signs of life (i.e. sales), it might be worth it to keep going. But if you really are seeing no results and that's not going to change, might be time to move on.

/r/Entrepreneur Thread