20 Entrepreneurs Reveal Their Toughest Business Lessons 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 .

#1- Importance of taking time to research

Photo Credit: Ross Cohen

The toughest lesson I learned was how important it is to take the time to research and pinpoint your target market. For business success, it is crucial to not spend years developing a product that doesn't have a distinct customer base. I wish someone had given us that advice earlier, but maybe it's one of those things you have to learn yourself. You have to feel the pain before you appreciate it. It was difficult to pinpoint our market, as we knew we would never make money off the job seeker. Instead, we went after the broader consumer market. Another tough lesson I learned was: don’t depend on anyone else to make your business a success.

Thanks to Ross Cohen, BeenVerified!

#2- Two Lessons

Photo Credit: Grainne Kelly

The toughest lesson I learned in business is: sign a confidentiality agreement before discussing your business ideas with potential partners. The biggest mistake I ever made was expecting that others would have the same degree of integrity as I do. I visited a Chinese factory with my original design and did not ask them to sign the confidentiality  agreement before sharing my design. While I was sitting in their office, the MD drove to Shanghai, 3 hrs away, and applied for a utility patent. Now, I don’t talk to anyone about anything without first signing a confidentiality  agreement. It has cost us tens of thousands of dollars, but I have learned so much about Intellectual Property along the way. Another lesson learned: don’t expect anything from anyone and you won’t be disappointed.

Thanks to Grainne Kelly, BubbleBum!

#3- Hiring too quickly and without any help

Photo Credit: Eddie Lou

When building a high growth, venture-backed company, it’s often easy to move too quickly without adopting operational processes. I and the two other co-founders of Shiftgig learned this the hard way. After experiencing a revenue spike, we decided to hire 18 new people, doubling our headcount at the time. However, we realized we were in over our heads when we had two people show up on the same day for the same position. We were hiring too quickly and without any help so we decided to improve our HR processes before bringing on any new people. Eventually, we found the right balance of keeping up with the company’s quick growth while still taking the time to put operational processes in place.

Thanks to Eddie Lou, Shiftgig!

#4- Micro-managing or re-doing things myself

Image Credit: Fabiola Hesslein

Balancing my inner-control freak has been one of the biggest challenges in owning and operating a business. I'm Type A; I'm very hands-on; and I'm very maternal about my company. But you do a disservice to yourself by getting burnt-out micro-managing or re-doing things yourself which adds to your existing workload. It’s important to be at your best, look your best, and feel your best in your work environment. So find people you really trust to handle what you need so you can let go a little and concentrate on your work-life balance. I’m finally getting better at it.

Thanks to Fabiola Hesslein, Tryon Entertainment!

#5- Why only 4 products?

Photo Credit: Fern Koh

I find customers asking me “why only 4 products?” and this is a challenge that I have always patiently address. Fernberry believes in the Slow Movement because we believe in the quality of life. While we are not techno-phobic, nor do we claim to eschew technology, we believe in making life’s choices in a very intentional and slow way. We believe in eschewing consumerism and connecting with the products we use, at a deeper level; by intentionally choosing what we want and how we want it. This is why Fernberry has a very strong work-ethic. Whatever we are going to do, we are going to do extremely well, while enjoying every single step of the journey, and putting in our soul at it.

Thanks to Fern Koh, Fernberry Skincare!

#6-  It's really hard to build a great team

Photo Credit: Steven Benson

There were a lot of challenges when I started Badger Maps, but the toughest business lesson learned is that it's really hard to build a great team. You need a team of great people to do great things, but it's hard to hire people who have the expertise that you need to build a company. I'm sure this is more true in some industries than others, and it's certainly true in our industry – software. The challenges to building a great team starts with finding great co-founders. Bringing in great people, who are the right fit, with the right skills onto the team early on when you face insurmountable odds is one of the toughest parts of launching a business. After you lock in the core team, making your first few hires are critical in terms of shaping the culture and getting your future leaders in place. The toughest lesson for me and for a lot of people I've spoken with is getting the right people in place on a team. It takes way longer and it's way harder to do well then I ever realized before I set out to do it.

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Thanks to  Steven Benson, Badger Maps!

#7- I couldn't help everyone

Photo Credit: Courtney Barbee

As cliched as it might sound, the hardest lesson I learned while growing my  company was that I couldn't help everyone. There were clients who weren't going to implement our advice, even if it meant saving their business. At some point, you have to learn to let clients go, because if they make terrible financial decisions, it reflects poorly on your services. I used to spend too much of my off-time worrying about the fiscal health of difficult clients, and I had to accept that there are some people who simply will not let you help them. Since I have learned to let go of some of that anxiety, I have been able to focus my efforts on the people whom I can help, and my life and business have improved because of it.

Thanks to Courtney Barbee, The Bookkeeper!

#8- Importance of indicators to signal when the market is changing

Photo Credit: Heidi Pozzo

One of the toughest situations I’ve seen was a business that did not have indicators built into the business to signal market changes. As the market began to change, they missed the front end indicators. At the same time, they had significant fixed cost structures through labor agreements and facility costs. When the market dropped out, they could not adjust the business in time and were forced to file bankruptcy. Many people lost their jobs without notice. The lessons: (1) Have front end indicators to signal when the market is changing (2) Manufacturing facilities in cyclical businesses should be owned, not leased, to protect cash flows in down turns (3) Labor agreements should have flexibility to allow the business to survive during market downturns.

Thanks to Heidi Pozzo, Pozzo Consulting!

#9- Always show contracts to an attorney

Photo Credit: Tara Langdale-Schmidt

The toughest lesson I’ve learned is always show contracts to an attorney. We had hired a company that was going to help us market our magnetic pelvic pain dilators to physicians and physical therapists. We mistakenly did not send it to our lawyer to review. The potential partner agreed on commission for sales, but made a drastic change in the contract one month later. At that point, we informed our attorney and he sent a termination letter immediately. But the situation could have been avoided if we had sent it initially to our attorney to review. Going forward, we now have our attorney review all contracts and business agreements in advance.

Thanks to Tara Langdale-Schmidt, VuVatech!

#10-If you don't trust your people at some point, your business is going to struggle

Photo Credit: Andrew Schrage

One of the toughest business lessons to learn is that if you don't trust your people at some point, your business is going to struggle. It'll be important to be as involved as possible in the beginning of launching a small business but once things are up and running and you have quality workers, it'll be important to take a step back, especially when it comes to the more menial stuff. If you don't, you won't have the necessary time needed to expand your business and maintain a focus on the really important stuff, such as maintaining or boosting customer service.

Thanks to Andrew Schrage, Money Crashers!

#11- I can't do everything

Photo Credit: Andrew Warner

By far the toughest business lesson I've learned so far is to allow myself to ask and receive help when needed. I'm typically a person that likes to try to do everything themselves. And when it comes to strategic business, that doesn't always work.  There's been many times where I've tried to: (1) Create Infographics and graphics (2) Crunch numbers and do accounting (3) Edit audio or video (4) etc. And none of those things are my strengths. My main strength of my business is my ability to write. That's what I enjoy doing. So, it took a while to learn that's what I really enjoy doing and looked for suitable individuals that specialized in things that I wasn't good at. This has helped me tremendously and taught me that just because I'm an entrepreneur, I'm not Superman. I can't do everything.

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Thanks to Andrew M. Warner,  Content Ranked!

#12- When to let employees go for the viability of the company

Photo Credit: Tanya Sammis and Mario Ochoa

Owning a small business it's always a challenge itself. Everything from the financial decisions to the shade of blue your logo will be makes an everlasting impact on the history of your company. In the seven years Sammis & Ochoa, a public relations agency, has been successfully running we have learned some lessons the hard way. The toughest one, by far, being the importance of knowing when to let employees go for the viability of the company. In the first and second year of founding the agency the dilemma of letting a couple of employees go due to their unsuccessful performance or keep them and hope they'd learn arose. This had become a roadblock that needed to be handled as soon as possible and with the company's future in mind. When things weren't moving fast enough due to these employees it became apparent that with a limited cashflow the company was not going to survive. It was not only costing us money to have them onboard but also energy. A situation like this really puts into perspective what is important and how businesses stay not only afloat but successful.

Thanks to  Sammis and Ochoa!

#13- You have to tell people no

Photo Credit: Kyle Brost

You can’t be everything to everyone, which means people will tell you “no” AND you’ll have to tell people “no”. It seems like a simple thing, that in the course of doing business, people will tell you no. That’s not necessarily the hard lesson to learn, the hard lesson to learn is that you have to tell people no. It’s always tempting to take on as much work as your company has capacity to fill, no matter where the work is coming from. However, you soon realize that there are people and organizations you’re not aligned with and shouldn’t work with. Learning how to identify these people and organizations and avoiding the temptation to say yes is challenging. It took me several brutal client engagements to realize the pain of working with them wasn’t worth the revenue. Once I became comfortable with saying “no”, I then had to learn what I was saying “no” to. I had to learn what personal and organizational characteristics were going to lead to a bad client relationship. However, learning that lesson and identifying those characteristics was one of the best things I could have done for my business. Our team is more productive, more efficient, more effective and our clients are more satisfied when we don’t just accept any and all work that is available.

Thanks to Kyle Brost!

#14- Be willing to fail fast and and fail small

Photo Credit: Jeff Greenfield

My advice is be willing to fail fast and and fail small. Often times when starting a business you will try a number of different tactics to achieve a goal and many will fail before you discover the most efficient and cost effective solution. If these failures can be small and fast then you will more quickly find a fitting solution. This mindset can save you valuable time and assets and keep you on track to achieve your goals.

Thanks to Jeff Greenfield, C3 Metrics!

#15- Resources and time don't always equal success

Photo Credit: Shawn Rubel

Entrepreneurship is rewarding, but it's not without its challenges. Unfortunately, I learned that resources and time don't always equal success. Several years ago, I tried to start up a website that targeted vacationers (specifically RV and camper-based vacationers), but unfortunately, I did this right before the recession hit. As you can probably guess, people weren't interested in traveling or buying RVs in a broken economy. I was certain, however, if I could just put enough time and  resources into the site, it would be a success. But some ideas simply don't pan out. It's frustrating, but I'm glad I learned this early on, because now I know when to call it quits on an project. Having this knowledge keeps me from wasting valuable time on something that ultimately isn't worth it.

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Thanks to Shawn Rubel, Vecteezy!

#16- I can’t do it all myself

Photo Credit: Tatyana Kozhevnikova

My learning in business is that I can’t do it all myself. I need to let control go off to some extent and trust that well qualified people can deliver – I need to become a Leader rather than a Manager within my own business. I need to focus on strategy and direction and share visions rather than detailed instructions with my team.

Thanks to Tatyana Kozhevnikova, Artefact London!

#17- There are terrible ideas out there

Photo Credit: David Siracusa

There are a million great ideas out there, and tens of millions of terrible ideas, that you can spend your money on. You would think that since this is my third business that I have started, that I would understand that. And yet, I still wasted tens of thousands of dollars on marketing and conventions and other ideas that I should have known would not work. I have finally gotten a hold of my spending and made sure to direct it only to the most effective areas possible. But I wish I had back half of what I spent. The best advice that I have heard to help with this, is to have a NO person. If you tend to spend money on everything, make sure that someone you trust can tell you NO! Or at least to slow down.

Thanks to David Siracusa, Siracusa Staffing & Leasing!

#18-  Building a business doesn’t make for an overnight success

Photo Credit: Lori Cheek

The toughest lesson I learned is that building a business doesn’t make for an overnight success. I believed so much in my idea that after our launch, I thought I was going to be a billionaire by the end of the year! Seven years into the entrepreneurial hustle, I’ve learned that entrepreneurship is being on a mission where nothing can stop you. It will take twice as long as you'd hoped, cost exceedingly more than you'd ever budgeted and will be more challenging than anything you'll ever try but if you give it your all and refuse to give up, you can trust it will be the ride of a lifetime. No matter what… this has been the most rewarding journey of my life. My advice to other aspiring entrepreneurs is to be brave and follow your instincts. You can't cheat the grind, but if you give it your all, you can trust that the payoff will be worth it.

Thanks to Lori Cheek, Cheekd!

#19- Have the courage and power to listen to that still small voice

Photo Credit: Alexis Davis

The toughest business lesson I've learned is *having the courage and power to listen to that still small voice* (inner voice) when others don't see your vision. When transitioning my jewelry business Hoo-Kong by Alexis Davis to a digital media company H.K. Productions Inc ( some people within my team just didn't get it. However, I knew deep down inside that my intentions to empower the users of my jewelry went far beyond jewelry itself. I wanted to expand and create a premier destination of thoughtfully filtered information from around the world that would help people help themselves. In business, you have to trust yourself, see the bigger picture, and be willing to go against the grain. A quote to remember is “You don’t have to explain your dreams, they belong to you.”- Paulo Coelho

Thanks to Alexis Davis, Hoo-Kong!

#20- Always have an outside inspector check your inventory shipments

Photo Credit:Chris Gronkowski

The toughest lesson I've learned in business is to always have an outside inspector check your inventory shipments. After receiving multiple perfect prototypes, we moved ahead with a big purchase. When the product arrived there was a slight defect with the pop top on the cups. We had to damage all the lids and get new lids rushed in which put us way behind. We now have every shipment inspected by an outside company before shipping to stop this from ever happening again

Thanks to Chris Gronkowski, Ice Shaker!

What has been your toughest business lesson learned? Tell us in the comments below

Mercy - CBNation Team

This is a post from a CBNation team member. CBNation is a Business to Business (B2B) Brand. We are focused on increasing the success rate. We create content and information 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 Blue16 Media.

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