30 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- To solve the problem and move on

Photo Credit: Cyrus Claffey

First, nothing ever works in the real world as well as it does in your testing environment. So you have to be prepared to tweak and improve your product a lot. Second, your product’s manufacturer can make or break you. Choose the right one! Finally, and most importantly, I learned that all you can ever do is solve the problem and move on. You’re going to hit a lot of bumps in the road, but the faster you can fix the wheels and keep driving, the better off you’ll be.

Thanks to Cyrus Claffey, ButterflyMX!

#2- To invest properly in the right hires

Photo Credit: Madi Waggoner

Hiring poorly. I hire all the time for clients, and like most entrepreneurs, I panicked when I felt I needed help and hired someone who came across my path instead of using my tried and true process. Even as someone who lives in the hiring world, I can still experience mental and emotional struggles like other entrepreneurs. I wasted money and time by not following my process. If I had instead invested properly in the right hires, my business would likely be in an even stronger place now.

Thanks to Madi Waggoner, Building Remote!

#3- Accountability is the key

Photo Credit: Charmaine Chan

My biggest failure as a business owner was mixing up the orders of my clients.  I mixed up the orders and ended up sending each order to the wrong person. What did I learn on that very unfortunate day? Accountability is the key. Checking and cross-checking are absolutely important in a business. Whenever you think you've got something covered, check again. When signing that document, check it again. Making a purchase? Check again. It will save you much more than rectifying your mistakes ever will.

Thanks to Charmaine Chan, IceSword!


#4- To hire the smartest and most talented

Photo Credit: Marina Vaamonde

My biggest failure at the start of my business journey was not delegating work to my employees. I was so obsessed with maintaining control of my company that I didn’t want to hire anyone to take some tasks off my plate. Doing everything myself burned me out and led to worse customer service because I was always running on fumes. I learned that the best CEOs hire the smartest and most talented employees so that they can delegate the day-to-day work of the company to them while the CEO does the big-picture strategic planning.

Thanks to Marina Vaamonde, HouseCashin!

#5- To always be in control of the company's direction

Photo Credit: James Becker

I nearly lost control of my company to two people I trusted to help run my business in C-Suite positions. They conspired together in an attempt to bankrupt the company and me in order to take control of it. The company and I only survived through some dear friends and the Grace of God. I learned that I should always be in control of the company's direction and decision-making to that extent.

Thanks to James Becker, Fusion Growth Partners!

#6- To be able to change perspective

Photo Credit: Tomek Mlodzki

One of my biggest failures was to limit myself to only what I knew. Sometimes this attitude can limit your success by not showing you the other possibilities. This failure, in the beginning, then drove us into a great and successful opportunity that turned our business around. In fact, we often remain locked into what we know with the fear of exploring new horizons, but with this approach, we are going nowhere, which is a big failure. Being able to change perspective is the biggest lesson I learned.

Thanks to Tomek Mlodzki, PhotoAiD!

#7- To work on something you love

Photo Credit: Gauri Manglik

I think the biggest failure I've had in my career is when I worked at a startup and we didn't have enough funding to grow. We were working on something very different from what we'd originally envisioned, and it just wasn't sustainable. I learned that it's better to work on something you love than something you think will make you money. If you don't love what you're doing, it's going to be a lot harder to get up every day and keep going.

Thanks to Gauri Manglik, Instrumentl!

#8- To always test the efficacy of your product

Photo Credit: Konstantin Soukhovetski

When I launched my product after years of research, I was very certain about its success. But, life planned to teach me the first lesson of business. The lesson I got from my first failure is this – Your product can be so good and useful but you can't be sure of success unless it creates a demand from the customer side. So, You should always test the efficacy of your product by taking surveys and putting the prototypes on display so that you would know the customer's perspective before the actual product launch.

Thanks to Konstantin Soukhovetski, Luxury Pianos Inc!

#9- To create a product that really hones

Photo Credit: Trey Ferro

More so than a failure, my greatest struggle over time has been figuring out the best way to reach people, at the right moment, with the right message. Operating in a space that is relatively new, we’ve had to test constantly and test everything in order to build a strong foundation for our business. Creating a product that really hones it in for both the customer and the business has been a challenge, but an empowering and liberating one, nonetheless.

Thanks to Trey Ferro, Spot Pet Insurance!

#10- To not be vague with what your business does

Photo Credit: Brett White

My biggest failure in business was trying to expand too quickly and being too vague with my niche. However, this couldn’t be further from the truth, in fact, having a niche that is refined as possible and having customers come to you for a very specific reason is the best way to sell products and services. I learned that if you are too vague with what your business does, it can confuse customers and they are way more likely to go to a company that does exactly what they need.

Thanks to Brett White, Addicted to Veggies!

#11- To get the most out of it

Photo Credit: Radhika Gupta

I have invested a lot in the irrelevant areas and targeted even those people to whom my products concerned less. However, It turned out to be bad. In the end, I have spent more than enough to generate leads. However, life gave me a chance to rectify my errors. I have learned a lot from my failure in business– ideas, planning, and targeting the right people matter the most to get the most out of it. Just pouring money into a business doesn’t make it a success.

Thanks to Radhika Gupta,  One Digital Land!

#12- To do things your own way

Photo Credit: Elijah Miller

I went into business with someone I thought I could trust, but soon learned that my so-called partner wasn’t as invested as I was in making the business a success. All he wanted to do was spend the profit without putting the hours in, and I realized that if the shop was ever going to succeed I needed to buy him out and do things my own way, so I raised the capital and that’s exactly what I did. And it taught me that the only person you can really trust in business is yourself.

Thanks to Elijah Miller, RC Ride On Cars!

#13- To always listen to your heart

Photo Credit: Adam Enfroy

My single biggest failure was believing the idea that I needed to work for someone else and should have had my life figured out by the time I left college. That failure taught me one hard, important lesson and that was always listening to your heart. Ignore what your brain insists is the correct thing to do and listen to what your heart and your gut tell you and follow that path. If you’re not happy, you’ll never really be successful, so follow your heart and be who you were meant to be.

Thanks Adam Enfroy, AdamEnfroy!

#14- To exit roles and delegate work

Photo Credit: Ashley Amor

My failure to structure the work and delegate tasks taught me the importance of human resources and task management. The thought that I could do a particular job better and faster was complicating my daily schedule and was blocking my employees from reaching out to me. This experience taught me to exit roles, delegate work, include my employees in the business, and function as a team, which helped me grow and work efficiently.

Thanks to Ashley Amor, People Find Fast!

#15- To be consistent and disciplined

Photo Credit: Michael Woods

In my early years, I *used to strive for perfection*, which can be beneficial in some circumstances but can backfire if it is overemphasized. I was so preoccupied with carrying out every task flawlessly that it caused me burnout and I lost out on a lot of great chances. I took away the lesson from that experience of being consistent and disciplined rather than striving for perfection because doing so will only result in personal development and growth.

Thanks to Michael Woods, Uniwide Formations!

#16- To know how to read the business

Photo Credit: Jim Campbell

A big mistake that I made, and one I see in many businesses is not knowing when to expand. When my business was small, I was scared of expansion, I didn't want to expand too quickly and waste money on personnel and space that I didn’t need. Because of this reluctance to expand, I ended up overworking myself and my small team of employees. This mistake taught me how to read the business I am in, and when best to trust other people with the work that you are doing.

Thanks to Jim Campbell, HoneymoonGoals!

#17- Making and maintaining personal connections

Photo Credit: Rob Greene

The gradual disintegration of my marriage. I was so busy working that I forgot that life should, and needs to be more than business, and how important the life and work balance really is. While professional success is an addictive high that we all crave, without someone to share it with, and spend time with, it feels a little hollow and meaningless and loses its appeal. My failure taught me the importance of making, and maintaining those personal connections that remind us what being human really means.

Thanks to Rob Greene, Price of Meat!

#18- To take everything one step at a time

Photo Credit: Karl Tippins

I was impatient and wanted an instant result. I rushed everything and because of that everything got out of hand. Ineffective planning, delays, mismanagement, and poor business progress have been the result of my rushed process instead of success. It was hard, but on the brighter side, I learned how to take everything one step at a time. It doesn't matter how slow the progress is, progress is still progress.

Thanks to Karl Tippins, Pension Times!

#19- To better work-life balance

Photo Credit: Paul Bowley

One of my biggest failures early on in my career as a CEO was getting lost in work. While work is important, it led to me neglecting my home life and familial responsibilities. What I learned from it was that I needed a better work/life balance otherwise it would lead to me being unhappy and burn out, which I often suffered from during the first year. Now I have a much better balance.

Thanks to Paul Bowley, Abbeycare Group!

#20- To make a product for niche audiences

Photo Credit: Ryan Cassidy

My biggest failure came to me when I was just a newbie entrepreneur. Wanting to grow quickly and make my company popular, I made a terrible mistake. I went too broad with my first product. I targeted every demographic, hoping to get more customers. My first product performed miserably, and I had to pull it from the market. I've since learned that you need to make a product for niche audiences. It makes your marketing much more focused and reduces the chances of product failure.

Thanks to Ryan Cassidy, Triangle House Hunter!

#21- To take on more rewarding projects

Photo Credit: Werner Jorgensen

Saying yes to everything people say has got to be my biggest failure. Agreeing to everything people said meant that I had a busy schedule and couldn't spend time on things I liked. I wasn't happy doing projects because my heart wasn't in it. That's when I decided to say no. I learned that it's better to take on more rewarding projects. After all, everyone is not your friend in the business world; people tend to exploit your kindness. So, it's best to look out for yourself.

Thanks to Werner Jorgensen, HeatXperts ApS!

#22- To plan ahead

Photo Credit: Liam Johnson

My biggest failure as a CEO is that I didn't realize how much work it takes to run a company. It sounds like a simple thing, but there are so many moving parts and people involved that I didn't realize how much time it would take to manage them all.  I've learned that the best way to avoid failure is to plan ahead and think through all of the potential issues before they happen. This will prevent you from having to deal with them in the middle of an emergency or crisis situation.

Thanks to  Liam Johnson, TheHitchStore!

#23- To be more careful when taking risks

Photo Credit: Kate Zhang

I had this great idea for a new product, but I didn't have the funding to bring it to life. So, I took out a loan and invested everything I had into making it happen. Unfortunately, the product didn't take off like I thought it would and I ended up defaulting on the loan. But, I learned a lot from that experience. I learned that I need to be more careful when taking risks and that I need to make sure I have the financial resources in place to weather any storms.

Thanks to Kate Zhang, Kate Backdrop!

#24- To always pay attention to current market trends

Photo Credit: Alvaro Moreira

I think that my biggest failure was when the time I wasn't able to close a deal because I was too young to understand such niches at a young age. I've learned that with age and experience comes intelligence and stoicism. That biggest failure taught me how to navigate my company, which led me to the professional that I am today. I always pay attention to current market demands and trends, as well as study beyond the jargon so that I can close a deal better and, in turn, help people who are in need of my assistance.

Thanks to Alvaro Moreira, Moreira Team!

#25- To define your goal with your company

Photo Credit: Marty Spargo

One of my biggest failures as an entrepreneur was not understanding the purpose of my business. I thought that it was to make money, but in the end, that's not what it's all about. It's about providing a service or product that people need and want and doing it in a way that makes them feel good about themselves by helping them reach their goals. One of the biggest things I learned from this experience is to define your goal with your company, not just profit, but also the purpose.

Thanks to Marty Spargo, REIZE!

#26- One step at a time

Photo Credit: Danilo Coviello

I failed to recognize my money is rather in the value I can create. That my money is the satisfaction I can give my client. I was biting more than I could chew. I didn't include my fellow competitors in my thoughts, that they too can offer the same service which would attract my clients to them. I overcharged anyway, and the dissatisfaction turned them away. My revenue level was affected. It took a while before I noticed this. I adjusted quickly. I took my business back. One step at a time is the valuable lesson I learned.

Thanks to Danilo Coviello, Espresso Translations!

#27- To build trust and keep clients

Photo Credit: Jason Ball

Early in my profession, I intercommunicated with a client. This cost the department money. I took responsibility when I discovered my mistake. I went to the customer & explained the missing facts. We finally convinced the client to cooperate with us again once he respected my honesty. I learned the importance of communicating, even bad news, to build trust and keep clients. It was a painful way to learn, but I only made this mistake once.

Thanks to Jason Ball, Considered Content!

#28- To focus on listening and speaking well

Photo Credit: Tiffany Payne

I was one of ten in a reputable media agency. I was new to corporate culture. Labor taught me discipline and hard work. I interacted with large clients and understood their needs. As a freshman, I ignored project details. I emphasized ethics and discipline. My poor listening abilities cost the company a major project. It affected my evaluation, and I discovered where I lacked. I discussed the matter with my supervisor, & he taught me how to handle projects efficiently. This project taught me to focus on listening and speaking well along with core principles.

Thanks to Tiffany Payne, Replace Your Docs!

#29- To optimize the website regularly

Photo Credit: TimConnon

My greatest failure has been not optimizing or touching my website for over 2 months. This resulted in a drop in my SEO rankings and my client base decreased by 20%. I learned from this that a website needs to be actively optimized on a regular basis and you should not take long extended breaks from link building. I managed to get the website back on track but this experience showed me that to have a good SEO-optimized website you must work on it with a regular schedule and not neglect it.

Thanks to Tim Connon, ParamountQuote!

#30- The need of communicating effectively

Photo Credit: Richard Mews

Early in my profession, I under-communicated with a client. I suffered a revenue loss as a result of this. As soon as I understood what I had done wrong, I went to the client and addressed the missing information as well as the reasons I had neglected to convey it. Unfortunately, I could not get the client to collaborate with me again. I gained insight into the need of communicating effectively, and how doing so may help build relationships with clients and keep them loyal.

Thanks to Richard Mews, Sell With Richard!

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

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