15 Entrepreneurs Share Their Biggest Failures and Lessons They Have Learned

The start and ongoing of a business can be rewarding and exhausting at the same time. Running a business successfully encompasses learning from mistakes that happen along the way which in the end, helps your business to be more strategic and to get back on track. We asked entrepreneurs and business owners about the tough lessons they have learned along the way.

#1- Trying to be the expert on all

Photo Credit: Henry O'Loughlin

I started a marketing agency that failed. It lasted about a year before I had to give up on it. Ten years later (and after working with many smart entrepreneurs since), I learned that I was way too cheap to ever make the business work. We needed a website, so I learned some HTML and built the site myself. We offered content writing as a service, and I'd be the writer. I did the accounting. I did the invoicing. The problem was that I was bad and slow at everything. I learned to invest to bring in experts where you need help, so you can focus on things you are good at.

Thanks to Henry O'Loughlin, Buildremote!

#2- Getting easily distracted

Photo Credit: Ron Tuch

Maybe it's my ADD or my ambitious personality, but as an entrepreneur, it's easy to get distracted by shiny objects. Unfortunately, at that point in my life, I was never able to move the needle in the right direction. There was a time I was trying to build three businesses simultaneously. Why is that a problem? Quite frankly, if your attention is split, your results will be too. I was getting average or above average results, constantly getting distracted, and was frequently suffering from burnout and fatigue. The biggest lessons I learned from this is to focus on your biggest passions, eliminate distractions, learn to say no, and to direct your attention on your purpose instead of the results. Following these principles helped lead me in the right direction and since then, I've never looked back.

Thanks to Ron Tuch,!

#3- A number of lessons

Photo Credit: Damian Birkel

I once served as a job search expert on a local tv station. There was even a weekly slot for me to share job search tips, tools, and techniques. It was great publicity for our nonprofit. My biggest mistake was devoting over 150%, and allowing myself to become emotionally involved with those at the tv station, instead of just coming in, doing my job and leaving. Looking back; over time; my expectations fell far “out of alignment” with management. I should have seen the signals and better anticipated the impact of shifting priorities, but didn’t. Yes, it flattering to be recognized when you go to the store or are running errands, but when it ended, I was completely “blown out of the water.” I didn’t even get a chance to say goodbye. It was truly one of the hardest crash landings in my career. But, I lived through the trauma, humiliation, burns and scars. I learned how important it is to precisely understand expectations, meet them, and stay on course. I also learned how blind I was to nonverbal communications. Perhaps the most valuable lesson was, that to survive & thrive, I needed to develop a protective outer shell. No longer do I have a “bleeding heart” or wear my feelings on my shoulder. It’s made me a more effective leader; increased my professional strength & grit; reduced stress and improved my business perspective. As painful as my experience it was, it was life-changing, and one of the most valuable lessons of my life.

Thanks to Damian Birkel, Professionals In Transition® Support Group, Inc.!

#4- Overlooking mismatched core values with clients

Photo Credit: Dana Look-Arimoto

One failure that I had early on as an entrepreneur was taking on a client that didn’t fit with my values. My business was new and I was worried about risk and not having enough clients, so I overlooked our mismatched core values. I learned that not only did this customer not fit with my values, but it hampered my ability to get better-matched clients later on. I ended up having to fire the client. That is never fun, but it taught me that it is ok to end relationships that aren’t working. It also proved that you can respectfully end a relationship without burning bridges. This resulted in happier clients that were a better fit with my values.

Thanks to Dana Look-Arimoto, Settle Smarter!

#5- Not being on top of my finances

Photo Credit: Andrea Heuston

My first employee – the office manager – had been recommended to me by two different sources, neither of whom knew each other so I thought that was a good sign and she was a solid hire. She didn’t work out. It was only after I fired her that I discovered she’d been embezzling from me, and the bookkeeper—who had had been my maid of honor at my wedding—was party to it, knowingly signing false expense reports. I signed a lot of checks not knowing what I was signing for. It was a big lesson to learn, that I needed to be on top of finances and I couldn’t even trust somebody who I believed was my best friend. I now review all payments and sign all checks.

Thanks to Andrea Heuston, Artitudes Design!

#6- Saying yes to everything

Photo Credit: Daniel Warmuth

My biggest failure was accepting every opportunity no matter how qualified it was because I thought I needed the money. Saying yes to everything filled up my schedule and used up my available capital. When I had a once in a decade opportunity very early on in my business I had no way of moving and taking action on it. It passed right in front of me. Ever since then I follow Derek Sivers advice of opportunities being HELL YEAH or no. Only go for the big shots. Scary in the short term, but has paid off big time in
the long term!

Thanks to Daniel Warmuth, Sprigbox!

#7- Copying another business

One of my biggest failures was investing lots of money in a business I thought would work for me simply because it worked for others. A few years ago, my sister and I opened a bakery business because we knew many people who had become successful with this kind of business. We didn’t know how to make our own products and we simply hired people from a popular bakery to bake products for us. After 3 months, we closed it down because we were not making any profit. I think my biggest takeaway from this experience was: don’t try to copy others. To build a successful business, you have to create your own products or brand. And that no matter what happens, you can keep recreating this product without relying on other people. I kept this lesson in mind when I started my next business, which is my blog, thismamablogs dot com. I built this blog all by myself, and although these days I hire people to help me with the tasks, I know that I can run my blog myself because I know the ins and outs of my business.

Thanks to Jane Sardoma Susaeta,!

#8- Agreeing to an unrealistic delivery date for a project

Photo Credit: Milosz Krasinski

I was subsequently unable to meet the date and the client refused to pay the bill. From this, I learned a very important lesson – never promise something unless you are 100% sure that you can deliver; however tempting it may be.

Thanks to Milosz Krasinski,!

#9- Not hiring right

Photo Credit: George Willison

I'm mid-70s and have a startup making a new Home Improvement type product that I invented. My whole career was with manufacturing companies. I did a lot of work in manufacturing and associated fields like accounting, HR, P&IC, minor engineering, etc. and all of that is very easy for me now. But I probably wasn't out of the plants more than 10 days in my whole career doing anything related to sales or marketing. So needless to say I have fallen flat on my face on the sales and marketing side of my company. (Right now it's a one-man show.) I read an infinite number of articles about how you can now sell and market anything and everything online and of course, believed it, and I've done what they said to do. But it's like a basketball coach reading 4 articles on how to play zone defense and then installing that for the big game. You just have to have done it a lot. Good marketing people make a ton of money and it is well deserved. Supposedly everything they do is available in on-line articles but reading and doing are two different things. What I've learned is that you have to find good people who are doing exactly what you need done, and doing it well. Then hire and motivate them to do outstanding work in that area, which for me is sales and marketing. I'm just beginning at that point.

Thanks to George Willison, theDECKtool™!

#10- Landing in jail

Photo Credit: Chetan Mahajan

My biggest failure was when I landed in jail for a month. I was an employee fronting for my employer, and was arrested in a case against my company. While in jail I realized that the company had made compromises. It had been twisted out of shape because the leadership was more interested in building a great valuation instead of building a great business. Eventually, I was released and my name cleared. I then started the Himalayan Writing Retreat (five years ago) and Old Hill cheese (three years back). Each grows at a natural pace, each is doing well, but neither has been forced or pushed into making any compromises.

Thanks to Chetan Mahajan, Himalayan Writing Retreat!

#11- Fear of taking risks

Photo Credit: Benjamin K. Walker

If we’re talking in terms of business, I’d say my biggest failure would be having the fear of taking risks. This was most prevalent during my first years as an entrepreneur, and it very much limited what I would’ve been able to do. Regret is my least favorite emotion, and I have lots of it because of my fear of taking risks. The biggest lesson I learned is that taking risks is part of the venture. Heck, the venture itself is a risk. Fortunately for me, I’ve learned to get past that.

Thanks to Ben Walker, Transcription Outsourcing!

#12- Micromanaging and lack of trust

Photo Credit: Karl Armstrong

My biggest failure so far is making bad decisions due to lack of trust towards my team. I am a perfectionist by nature. Thus, I want everything error-free and excellence-driven. This caused me to develop a habit of micromanaging and lack of trust towards my team. Eventually, it led me to make insensitive and raw decisions that disrupted my team. Lesson learned trust starts with leadership. If you don’t trust your team enough, they will not trust you with their brilliant ideas and outstanding efforts. As a leader, be the one to reach out. Be an example of how trust should be cultivated within the team. Give them your trust, so they could give theirs too. Trust between you and your team is always two-way.

Thanks to Karl Armstrong, EpicWin App!

#13- Lack of a launch plan

Photo Credit: Anastasia Schmalz & Tomer Arwas

Build up anticipation for your new offer with a launch plan! Our first launch was an absolute disaster! We had spent 2 months behind-the-scenes on creating a great travel coaching program. We ran surveys and interviews with prospects, connected with industry experts, drafted a program curriculum, and created a beautiful sales page. So far, so good. Once we were ready to launch, we announced the launch in three 15-seconds Instagram stories and went on vacation, hoping that sales would rush in. They did not and we got terribly demotivated. Our biggest mistake was that we didn’t have a launch plan. Lesson learned? Carefully craft a launch plan to build up anticipation for your upcoming offer. Having a plan of how you will promote your offer with a series of communications (emails/posts/videos) will warm up your prospects and help convince them of your offer. We implemented our learnings into our next launch and reached our sales goal within 5 days. As important as the quality of the product is, marketing is at least equally as important.

Thanks to Anastasia Schmalz & Tomer Arwas, Generation Nomads!

#14- Trying to do everything on my own

Photo Credit: Jacob Martinez

Every business owner, even the greatest ones, has made mistakes and experienced failures at least once in his/her life. And, of course, I am no exception. What I consider my biggest mistake is trying to do everything on my own. There was a time when I lost my employees and almost lost my business. During that time, I wanted everyone to listen to me but I didn’t want to listen to anyone. I made plans on my own and I made decisions on my own. Through that experience, I have learned that success cannot be achieved on your own but can be achieved through collective effort. I have learned that it is important to be open to other people’s insights and opinions.

Thanks to Jacob Martinez, SwiftClean!

#15- Falling deep on my debts and loans

Photo Credit: Timo Wilson

I thought that as an expert I have been doing what I tell to my clients and that I am careful with my finances. But things happened, knowing that I could have money anytime I got out of control. I have been overspending and I’m letting my due dates pass. It is when my business was not doing great when I realized that I've made such a big mistake with my personal finances. Since then I started managing my expenses very well and I always keep in mind spending only on essentials and things that I need. I also learned the value of money in a hard way so now I try my best to save for emergency situations that may occur and invest in the stock market and other industries. Keep in mind that being a CEO and financial expert is not an excuse to be comfortable enough on your expenses.

Thanks to Timo Wilson, Asap Credit!

What has been your biggest failure? What have you learned? Tell us in the comments below. Don’t forget to join our #IamCEO Community.

Mercy - CBNation

This is a post from a CBNation writer. CBNation is a Business to Business (B2B) Brand focusing on increasing the visibility of and providing resources for CEOs, entrepreneurs and business owners. CBNation consists of blogs(, podcasts ( and videos ( CBNation is proudly powered by Blue 16 Media.

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