15 Entrepreneurs Share the Mistake That Cost Them Success


Plenty of people have dreams of starting their own business or launching a startup, but the truth is, as many people fail as find success when it comes to being their own boss or striking it rich. You might have a leg up if you read through these 15 honest confessions about the mistakes that were made by others who have gone before you.

#15. In hindsight.

“Entered an over saturated market with zero business, marketing or sales experience.

In hindsight, my chosen niche wasn’t specific enough. I’ve had a follow up idea from the experience I had, but I have zero intention of actually executing it.”

#14. Legalities.

“Years ago I tried freelancing hooking up electronics. I made a decent amount of mistakes but nothing totally crazy. I also most definitely didn’t know as much as I should have before starting something like that. But my biggest mistake was not getting bonded in any way. I had a really close call where a customer threatened to send me to court for breaking some electronics I didn’t even touch. I doubt he would’ve won but who knows what I do know is I would’ve have been able to afford to find out. I shut it all down after that.”

#13. Lessons.

“In the startup community + have watched many a start up fly and fail (mine is still breathing). Here’s what I’ve learned:

Pick your co-founders like you pick a marriage partner — with the expectation that they may very well screw you over anyway.
Don’t invent a product for a problem that doesn’t exist. If you do, you will have to spend a lot of time inventing the problem as well.
Take your experience and apply it to what you want to do. Don’t jump in to app building b/c all the cool kids are doing it.
Don’t get in it for the money. You will likely be working for AT LEAST two years without adequate (or any) pay.
Don’t try to be a BFF to your employees/boss. It seldom ends well.

Specificity and focus are your friends. You can’t be or do everything for everyone.
Your first customers are your employees. If they don’t see value in you or what you’re selling, you’re in trouble.
Working for smart, kind people is totally okay. There are hundreds of ways to do cool things, without entering the startup world.
Take care of yourself first. Throwing everything you have into a biz is no good if you destroy your health in the process.”

#12. Be prepared.

“Lots of things:

I sold clothing wholesale:

Had sales experience, but came from a different industry. It took a little bit to learn the law of the land and how things worked.
Made home base where I did (and also currently) live instead of moving to a more regional hub. This caused extra travel time and expenses when I could have been closer to my accounts. There’s a reason why reps work out of those hubs.
I was not prepared for the amount of stores who wouldn’t pay. If an account gives you trouble about placing a deposit or prepaying then you’re probably not getting paid.
Some of the lines we represented were off trend. We were newbies in the market so we kind of went with what we could get, but there are reasons that longer established and larger firms were repping certain lines and not repping other lines.
I didn’t watch my business partner close enough and took him at his word. He was a lying piece of shit who was out for himself and he no problems screwing me over and running off with some of the money we did have.
I learned a lot though, and while I don’t own a business currently, I certainly will be more prepared for when I try again.”

#11. Self-confidence.

“Lack of self-confidence.

This was about 23 years ago, when the Web was really taking off. I knew it was going to be huge, and I knew that businesses really needed to be online, but my lack of self-confidence kept me from convincing others. It really held me back, and after a year and a half I had to find a full-time job.

But I don’t regret the time I spent trying; in 2001 the web development firm I was working for (and we had done some really high-profile projects) burst in the dot-com bubble and the resulting recession kept me from finding another full-time position. But everything I had learned from them, plus what NOT to do the first time, meant that I was able to freelance for the next 8 years.

So I always tell people to go for it. It may or may not work out, but you learn so much and it takes you where you need to be. It sucked but I wouldn’t have traded that experience for anything.

Edited because time flies.”

#10. Friends.

“Hired friends.

Didn’t do that this time around. Worked out.”

#9. No art collectives.

“I started an independent engineering consultant firm that was made up of only me. Turns out I spent so much time trying to get old customers to pay me, that I didn’t spend enough time looking for new customers. Side note: I will never ever sign a contract with an “Art Collective” ever again. They agreed to pay me a flat rate ($5000) to automate a project they were building that involved some motors spinning some disks or something. The job took me maybe 4 hours not counting the travel (but hey they agreed to a flat rate). They never sold the piece and never paid me, even though my contract had no language tying my compensation to project success. Anyway they dissolved the “Collective” and reopened it under a new name… and I never got my money. Repeat that story about 4 more times and I went back to working for someone else.”

#8. More than drive.

“Didn’t have enough starting capital. So we shifted our business plan to bring in some small capital to save up for our major plans. During that process, I realized my business partners were not what I was looking for. They just didn’t have the right mentality for what we were doing. The drive was there, but drive isn’t all we needed.

So I bailed out of it before I lost anymore of my money.”

#7. Follow the money.

“When it came to marketing channels, I didn’t follow what the numbers said was working.

I had my heart set on building a blog to promote my products. But all my sales success came from influencer marketing. If I had to do it over, I would have dropped the blog and put everything I could into the marketing channels that worked.”

#6. Pick a lane.

“I’ve launched multiple pen names for smut, and a fair few of them have just died in the water. (At least, I hope that’s water…)

The biggest failing was assuming that I could try and use one name for all the fetishes I wrote about, assuming that people who bought in one niche would buy in others. Not so. People like what they like, and they like to know they can buy more of it consistently.

Pick a lane and stick with it. It’s a lot easier to build a reputation for quality in one niche than all niches simultaneously.”

#5. Year one projections.

“I didn’t have enough money to operate the first year at a loss. Seriously, it is so important to have that. I mean technically my business could have survived, but I’d have starved. When factoring in year one projections: don’t forget your salary!”

#4. Market research.

“I never started a business but I work in accounting and have seen a lot of businesses succeed/fail. I think the most simple thing that goes wrong is just people often don’t really do market research and start a business that they are passionate about but it’s for a product or service that the people in that area don’t want or need. Also I think some people have good idea but don’t have any or enough experience in owning or running a business and underestimate the work it takes.”

#3. Too naive.

“I was too naive. As an engineer, I just wanted to build a product for the customer and then hope that it would sell itself and I would be on my Merry way. So I built dispatching software for a local truck company. After I finish building it out, I do some research and there are at least 10 other competitors with better fetaures and have been around longer.

Then I try cold calling other truck companies in the hopes of selling my software to them. Lo and behold, they were already using a competitor’s software to power their operations. I also had to price myself lower in order to try to be a compelling offering. So now, here I am with 1 customer getting paid $150 a month.

In essence, I fucked up in not doing enough research, not coming up with a more unique product, trying to be 5% better that competitors, not being able to get help on the sales end, and much more. The only thing I did well was to build good software.

Now, I wake up everyday depressed, not knowing what the right next step is, running out of money and time. The hardest part is the loneliness of it all. I miss having a team.”

#2. The wrong investor.

“I got the wrong investor….my dad.

My dad was the kind of parent who couldn’t trust me, and unfortunately still thinks he’s a fellow kid who totally understands today’s tech scene when he’s…….well. Let’s just say his idea of a great app is to load everything with ads, create 50 unnecessary additional steps to force everyone to see what our app can do, and oh…the 80s silver, blue & yellow gradient effect everywhere.”

#1. Get it in writing.

“I trusted my banker without getting anything in writing.

I had been thinking for a while about leaving the law firm I was with to start my own practice. I spoke with my banker who said it would be no problem for me to get a loan or line-of-credit if I needed it. I had some savings, but I relied pretty heavily on her representations. We had a great history and she had never let me down before. Big mistake.

So I started my own practice, did okay for a few months, then hit some slow months. I went to talk to her and she said there was no way she could do anything to help me until I had shown two years of profit. I got angry and asked her what about our previous conversation when she said that she had multiple ways she could help me. She claimed she never said anything of the sort. I remember standing up and leaning over her desk and saying “You told me you could get me a $15,000 line of credit within 24 hours based on my customer history with the bank. And now you’re telling me I dreamed this conversation?” She basically said she would never had made such a specific promise, and I clearly was trying to bully her. I left her office and immediately went to another branch to close all my accounts.

Every time I think of that conversation, I get furious. I had sent her God knows how many customers over the years, had a long history of banking at her branch, had been to lunch with her numerous times, yet she called me a liar when I had to ask her for a help for the first time in the history of our relationship.

In hindsight, I was stupid and a little arrogant. I knew it would take a couple of years to truly establish my practice, but I thought I had enough in savings and current clients that I could make it. When she told me about the financial options I would qualify for, I knew I had enough of a safety net. I made it 14 months before I had to close up shop and find a job (happy ending though: LOVE my current job).

Still, it’s a little frustrating to be on the verge of making it on your own and have the rug pulled out from under you by someone you considered a reliable ally.”