14 Entrepreneurs Share Their Biggest Business Mistakes

The best have become the best because they have learned — and a lot. Although we like to believe that we are learning from books, seminars, webinars and courses, it does seem that, in the end, the best business lessons are the business mistakes we make. Especially in the entrepreneurial world, the things we empirically learn, tend to stick for good. Thing is, it’s highly unlikely that you’ll learn in school about capitalizing your hobby or the perfect moment to exit and sell your business. These lessons are mostly learned from practice, more often than not the hard way.

These business mistakes also make the entrepreneurial journey ever so interesting. What’s more, what separates true business leaders and achievers from those who just couldn’t cut it are in fact the mistakes that they make.

The business hunch, the gut to continue when you’ve obviously had a huge fail, and to maintain your confidence in the next steps… These phases are mission critical when overcoming the down points in your entrepreneurial career.

To see whether our thesis sticks, we have talked to 14 entrepreneurs to give us their thoughts on their biggest, but most significant lessons. Behind their failures of yesterday, are now their today’s successes and healthy businesses.

Whether it was about poor hiring decisions, bad choice of partners or failing to recognize the power of timing, read away and try to sink as much wisdom as possible.

1. I Started the Business for All the Wrong Reasons

For me, the biggest mistake was starting a business for the wrong reasons. Apart from bad motivations as money, lifestyle, trends, vanity etc. the biggest mistake is to start a venture around an idea that you are not really passionate about. The problem you want to solve, the people you solve it for (your potential customers) and the people you co-found with should really mean something to you. And by meaning I mean you should LOVE it. You should be prepared to work on that for the next 10 years. Otherwise, you waste your time and you will most likely burn out. Search for an idea that really means something to you.

Andreas Diehl is a digital entrepreneur, consultant, and public speaker.

2. I Trapped my Business in an Office and Bills

In growing my web agency I was way too quick to hire full-time employees, lease long-term office space, and take on other fixed-cost commitments. That put me in a position where I was constantly just trying to get enough business through the door to pay the bills, rather than having the flexibility and freedom to spend time finding the right clients and the right business model.

Matt Inglot is the founder of web agency Tilted Pixel Inc and helps freelancers build their own businesses.

3. We Confused Thinking Big With Acting Big

When I just started my business, I confused thinking big with acting big. This resulted in me being impatient, expecting the immediate results and progress. Each delay in getting there felt like a failure. After discovering One Thing by Gary Keller, I learned to think big but act small. I focused on one critical thing each day, week, month, or quarter that was strategically connected to the desired outcome. It helped with setting direction and executing on it over time without burning out or getting distracted.

Maria Dykstra is the co-founder of the marketing company TreDigital.

4. I Failed to Capitalize on my Hobby

My biggest business mistake started before I actually started Simply Stated Media. It was back when I was blogging for fun and created a local, lifestyle blog. I worked on it for years, attracting readers and building notoriety. But I didn't realize then that I should have been capitalizing on my audience by funneling them into an email list. If I would have been doing that, over the years I would have been able to build an engaged email list that I could have sold once I started my business. I failed to see the potential in my audience and therefore lost a big opportunity to generate business from the attention I attracted. Don't make this mistake. Always be list building, even if you haven't started your revenue streams yet.  

Raubi Perilli is the founder of the marketing company Simply Stated Media.

5. I Let my Business Die Instead of Selling It

My biggest business mistake was not selling my previous SIM unlocking business at its high point. At that point I also started losing interest in it, so instead of exiting and cashing out – a concept I simply wasn’t aware of at the time – I let it die out.

Steven van der Peijl is now CTO of JobRack, a job board website.

6. I Compromised on my Standards When Hiring

When heading a startup, you're starting from scratch and manifesting an abstract idea, often working with a shoestring budget. Putting together the right hive is crucial, but because there is a lot of rolling up of the sleeves and shitty pay, you come from a place of gratitude and give a person more leeway. Many times my gut indicated that a person didn't have the stamina it takes for whatever reason. To work in a startup, you need to be a self-starter with vision and ideally team members need to be aligned with the greater mission. I realize now that it's not worth compromising your standards even if you have to keep looking. I've wasted my time with a lot of people who turned out to be ‘freaks' and ‘flakes.' I recommend a 30 trial before offering any equity.

Maryam Henein is an investigative journalist, founder, and editor-in-chief of HoneyColony.

7. Instead of Working on my Solution, I Chased After PR

A mistake I've made more than once was allocating too much staff time to getting PR for our self-funded startup's products. Journalists have sold their souls to investors because they want early investment opportunities, freebies, and perks. If you bootstrap what you're building, approaching major news portals is futile. They may present themselves as discoverers of tech breakthroughs but what gets their attention is who – other than the founders – have footed the bills. I know now to let press come to us.

Saul Fleischman is the CEO at a social media toolkit company RiteKit.

8. I Thought I Needed to Mirror my Competitors’ Marketing Budgets

My number one mistake was made with my second company in thinking that I had to mirror budgets of our big-name
competitors. I thought that in order for us to make it through the noise we had to spend top dollar on advertising, just as much or more, than some of our biggest competitors. I soon found out the hard way that it would not work for us. We were constantly in the red and thought we would have to close doors.

My husband and I decided to make one last-ditch effort to save the company by pulling 90 percent of that ad money. We were thrilled to see that we brought in just as much traffic to CorpNet.com organically via other marketing efforts. We immediately went into the green and became a profitable business. I learned my lesson that as a small business; you don’t need to try and beat big-name competitors. Instead, make a niche for yourself and stick with that.

Nellie Akalp is the CEO of CorpNet.com.

9. We Thought We Could Succeed With Minimum Effort

My biggest mistake was probably starting a joint venture with another successful entrepreneur, and assuming we'd be able to succeed with it with a minimum effort. We did make sales, and we did an okay job on the service, but overall it was a failure. In hindsight, we could have promoted it better and could definitely have spent more time working on it successfully. There was a lot of short-term damage at the time, in terms of time wasted, refunds given, and people's opinion of both of our brands being harmed. Overall, though, you live and learn and focus on what you're good at instead, and people will be much more forgiving.

Dom Wells is the CEO and founder at Human Proof Designs.

10. I Made my Business Decisions Based Only on Money

When I ran a branding studio in Los Angeles, I often pursued work that helped me earn a lot of money but didn't allow to me feel particularly challenged or fulfilled. I eventually learned that allowing yourself to make business decisions based on more than just money tends to result in better work, a better reputation, but also a sense of earned accomplishment and happiness that would be difficult to come by, otherwise.

Colin Wright is an author, blogger and international speaker.

11. 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.

12. I Should Have Started my Blog in 2005

My biggest business mistake is not entering the online business world soon enough. Businesses of any niches favor first movers – this also holds true with online business niches.  It's way easier starting a, say, business blog in 2005 than in 2017: Acquiring new readers are easier, thus it's faster to build a community and generate profits at the same time.

Ivan Widjaya is a serial entrepreneur and founder/CEO of online publication Noobpreneur.com

13. I Hadn’t Done my Homework Properly

My biggest mistake was thinking that I researched my market in depth when starting Richtopia, it took me a year to realize that I hadn't done my homework properly so I went about doing it a year late.

Knowing your field of operation is of the utmost importance. During Richtopia's growth, I was introduced to Tim Campbell MBE at Bright Ideas Trust who helped me refocus my business efforts to really make even more impact with thousands of unique users regularly visiting our website to get insightful business information.

Derin Cag is the founder of digital platform Richtopia.

14. I Rushed to Launch (More Than Once!)

Hands down my biggest mistake in business has been (repeatedly) rushing to launch products and services that I thought the world absolutely needed, without first taking the time to validate those ideas with real, paying customers. With my very first product, the iStash, I spent over a year prototyping, tweaking my business plan and working with overseas manufacturers and eventually placing a huge first order of more than 3,000 units all without even pausing to ask my target market if the product was something they'd be willing to pay for. After receiving that shipment, I realized I had a major problem: I had just created a product that nobody really wanted. This experience and others like it, have forced me to no longer pursue building a new business or creating a new product without getting a handful of excited, paying customers first.

Ryan Robinson is an entrepreneur, writer and freelance content marketer.

Final Thoughts

Do any of these sound familiar? Or, better said, do any of these sounds like something you’ve been doing without realizing it?

Hard as it may sound, business mistakes are bound to happen. Some may even come in disguise as perfect decisions at the time. But, truth be told, making a mistake is not the hardest thing to do. The toughest part is getting past around it. Sticking in spite of the tough times.

If you truly believe in your business idea, want it to succeed, then follow the lead of these 14 entrepreneurs. Remember the regrets, but keep going.

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Written by:
Neil is the founder of JobRack. He is a digital nomad and has created multiple SaaS solutions to help small and medium businesses with lead generation and funnel building. His current focus is helping businesses create better growth systems.
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