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This article was published on January 25, 2017

12 entrepreneurs discuss their biggest business fails and the lessons they learned

12 entrepreneurs discuss their biggest business fails and the lessons they learned
Neil Napier
Story by

Neil Napier

Neil gave up his corporate career to indulge into startup SaaS world, helping community benefit and automate most of their business. He is a Neil gave up his corporate career to indulge into startup SaaS world, helping community benefit and automate most of their business. He is a serials entrepreneur and CEO of Jobrack and Adaptively.

No matter whether we are starting, already onto something big or still kicking it small, the journey is tough and the wisdom is hard-gained. A crucial part of hitting it with success is making mistakes, and not repeating them!

When preparing for the entrepreneurial journey, many set out on a quest of a perfect path. It is usually about having a short and successful cycle full of right decisions to their desired goals. Everyone has their doubts, but the majority think what we are doing is the best way and we often fail to see the long-term effects.

The truth is – there is plentiful of mistakes every entrepreneur makes. Some hurt our ego (or budget) more and some have a lesser impact. But, what about the biggest ones? They stay engraved and are not to be repeated again. Or, so it should be.

We often regret what we didn’t do, as opposed what we did – but failed still. However, in business, the downturns can be caused by taking either turn.

This is why we asked 12 entrepreneurs to talk their biggest business mistakes, what they learned from them and what is the one thing they will not fail to avoid doing the next time.

1. I tried to do everything by myself.

The biggest mistake I made was trying to do everything by myself. Instead of getting out and about meeting new people, sharing ideas and exposing myself to new opportunities, I chose to work in isolation.

The more people you know in business the more likely it is you will find new opportunities and connections that help you succeed earlier. These days I make it a point to meet as many people as possible from bloggers and journalists to local business people and entrepreneurs. A large network of connections makes starting a new business much easier.

David Mercer is the founder at and a best-selling author.

2. We gave up instead of pivoting or partnering up with an expert.

One of the biggest business mistakes I’ve made was in one of the first companies I built when I was in my early twenties. It was a web agency creating websites and e-commerce solutions. I and my partner knew nothing about the web but were just really proactive about sales.

Pretty quickly we had over 200 clients, but our project management and solutions were crap, often giving too low prices and promising too much. The mistake we made was that we gave up and sold it to a bigger agency for pennies.

We had customers and we’re good at sales, so I really regret not pivoting a bit and maybe getting a third partner that had experience in the web industry. Since then I’ve really learned that it takes time to create a business and just starting from scratch the whole time is not the solution. That was a great lesson to learn early!

Nikolaj Astrup Madsen is the CEO and founder at Refuga.

12 Entrepreneurs Share their biggest business mistakes

3. I didn’t push my ex-partners to work harder.

My biggest business mistake was not doing my due diligence. Also, I didn’t check up on the work of my previous business partners. As a result, I got screwed over too many times.

This is most often the case with technical co-founders who are often taken for granted by their marketing counterparts. The marketers feel it’s okay to only start working on ‘their’ thing after you have first invested months (or years) of your time and money to build something and it’s ‘finished’.

I’ve lost about 14 months of my life due to this happening twice with now ex-business partners. Luckily I’ve now finally found a great (marketing) business partner!

Steven van der Peijl is now CTO and partner at JobRack.

4. I took on clients only to cover costs.

Taking on clients only to cover costs but not feeling a great connection was my biggest mistake.

It brings cash in the first place, but a lot of unhappiness and misunderstandings later on. And that cash really doesn’t cover up for your wasted nerves, nor brings you good experiences or further business.

Pamela Wagner is a digital entrepreneur and paid ads specialist.

5. I didn’t realize I started a business.

My biggest business mistake would be not realizing that I started a business. When I first started my blogging business, it was all just a hobby, and, therefore, I didn’t take it very seriously. I started on the wrong website, made some design mistakes, and so on.

This held me back in the beginning because many people didn’t take me seriously in the beginning.

Michelle Schroeder-Gardner is a personal finance and lifestyle blogger behind

6. I allowed myself to work with no clear strategy.

The biggest mistake I’ve made is to not focus on strategy, first and foremost, rather than doing work and getting stuck in the weeds of the day to day.

If you have a solid, clear strategy in place and continue to make that the top priority regularly, it’s much easier to determine all of the actions and next steps that need to take happen, instead of simply doing for the sake of getting work done.

It’s key to understand your direction, know how to make decisions, and focus on what is most important next. I set aside time at the beginning of each week to review quarterly and weekly strategy at a minimum for my business.

Victoria Chemko is the Principal and Chief Inbound Strategist at Umarmi Marketing.

7. I didn’t incorporate right from the start.

The biggest mistake I made when launching Impressa Solutions was not incorporating right away. Starting a sole proprietorship was a little cheaper and easier at first, but restructuring two years later ended up costing me even more — in time and money!

Julie Ewald is a founder and CEO of Impressa Solutions and a digital entrepreneur.

8. I trusted a complete stranger to manage my finances

I have had 18 businesses, so there have been lots of mistakes and with that lots of lessons. The biggest one was trusting someone to manage my accounting and bill pay. That person ended up stealing over eight thousand dollars. The lesson learned? Never trust anyone without doing a background check first.

Sue Zimmerman is also known as #TheInstagramExpert and founder of Sue B. Zimmerman Enterprise, LLC.

9. I waited too long to make the jump.

My biggest mistake was to wait for too long before jumping into the entrepreneurial world. I wanted to make everything perfect before launching my side. It is better to launch with whatever you have, experiment along the way and improve based on the learning and feedback.

Harry Vaishnav is the co-founder of the consultant company SmallBizViewpoints.

10. I should’ve stuck to the course

My biggest business mistake is and has always been giving up too quickly. There were a couple of times when I had an idea, would run with it for a few months, and then give up after lackluster results. If you truly believe in something, you have to stick the course.

Brandon Lewin is a marketing professional and entrepreneur.

11. I lost $20,000 trying to scale up too quickly

My biggest business mistake which cost me over $20,000 was trying to hire and scale up too soon. It was in early 2015 when I was selling t-shirts through Teespring with Facebook advertising. I was having a few successful campaigns myself so I thought if I could hire a proper team I could scale this up quickly and make a ton of dollars.

So, I decided to bring on a full team of one project manager, one FB ads manager, one researcher, and one graphic designer. But things didn’t work out as well as I thought. I didn’t have the skills to train my team properly and ended up spending so much time on unnecessary things. My burn rate was quite high at $2,000 – $3,000 a month so after six months I decided to call it quit.

If I could do it again, I’d hire only one person first and get him up to speed then hire the next.

Tung Tran is the founder of

12. I did not invest in the right team members.

My biggest mistake was not investing in the right team members. Early on, I spent money on cheaper products and services and just ended up becoming frustrated. I started living by the philosophy “do what you do best and outsource the rest” and started hiring people who were better than me in different areas of my business. That was the turning point for me.

Chirag Kulkarni is a Serial Entrepreneur and Marketer.

Final thoughts

Some mistakes are monumental and so costly that you feel that you will never recover from them. But, rises and falls are equal parts of any cycle – either business or life. Do not lose your enthusiasm long-term over a current failure.

However, do bear in mind that the act of making a mistake itself will not cause you most problems.

You will have far more work to get over the regret. And continue to work regardless of the tough times.

Follow these 10 quotes as living proof that mistakes can be overcome and get successful – as long as you set your mind to it.