In the face of failure, entrepreneurs come to recognize their transformative power, utilizing setbacks as a means for personal and professional advancement. It is through past challenges and errors that we grasp the significance of perseverance and flexibility, understanding that each stumble is an opportunity for growth. When we embrace failure as a stepping stone towards success by showcasing resilience and determination, we'll be likely to emerge stronger from adversity.
We asked entrepreneurs, and business owners how they have failed and what they have learned. Here are some responses.
#1- Underestimated the importance of cash flow
One of my early failures was underestimating the importance of cash flow management. I was so focused on growth and expanding the business that I neglected to monitor our expenses and incoming revenue closely. We faced a brutal financial crunch that nearly jeopardized the business. What I learned from this mistake is the need for disciplined financial planning. I now prioritize cash flow forecasts and maintain a buffer for unexpected expenses. It was a hard lesson, but it reinforced the importance of balancing growth with financial stability and having systems to manage both.
Thanks to Burak Özdemir, Online Alarm Kur!
#2- Inability to find the right language for communication
Yoga therapy is a concept many people are not familiar with, which can make it a challenge to educate others who might benefit from working with a yoga therapist or from becoming a yoga therapist themselves. On my journey as a yoga teacher, yoga therapist, and co-founder of a yoga school that trains yoga therapists, I’ve had to learn from my mistakes and develop nuanced language to explain this work. It has been rewarding to spread the word about yoga therapy more effectively and help others harness the healing power of yoga.
Thanks to Anna Passalacqua, Breathing Deeply Yoga Therapy!
#3- Not investing enough time to building a strong team
One of my early failures was not investing enough time in building a strong team. I thought I could manage everything independently, but it quickly became overwhelming and led to missed opportunities and slow growth. I learned from that experience the importance of trusting and empowering others. Surrounding yourself with talented, passionate individuals who bring diverse strengths to the table is essential for business success. Delegating not only helps you scale but also allows you to focus on the bigger picture and long-term strategy.
Thanks to Tim Johnson, Revolution Health Marketplace!
#4- Two failures
I’m extremely proud of my team for making it work even when projects are challenging. We consistently produce strong designs and overcome logistics issues that arise. In these situations, the failure tends to be in our decision to take on the project in the first place or to undercharge for work that requires more time, effort, and resources. Over time it has gotten easier to spot these sorts of issues and avoid them. We’ve also learned that we can recoup the losses on an initial smaller project by winning a customer’s trust and selling them on more projects in the future.
Thanks to Thomas Samuels, Cardinal Expo!
#5- Rushing growth without proper testing
One of my failures at ShipSage was trying to scale our technology too quickly. We rolled out a new system without fully testing how it would fit with everything else, which led to delays and inefficiencies that impacted our team and clients. I learned that rushing growth without proper testing can backfire. Now, we take a more careful approach—phasing in new systems, getting feedback, and making sure everything runs smoothly before expanding. This experience taught me that growth needs to be ambitious but also well-planned.
Thanks to Ben Pu, ShipSage!
#6- Not recognizing when to let go
One of my biggest failures was not recognizing when to let go. Early in my career, I held onto a project far longer than I should have, believing that sheer grit would somehow turn things around. But sometimes, a sinking ship isn’t a test of endurance; it’s a lesson in letting go. It took me too long to realize that pouring more time and resources into something that wasn’t working was actually holding me back from new opportunities. The lesson? This does not mean avoiding failure, but knowing when to walk away and start fresh.
Thanks to Peter Murphy Lewis, Strategic Pete!
#7- Neglecting my own health
As a business owner, attorney, and legal expert, my initial focus was on growing my practice and meeting the needs of my clients. But, I was so caught up in this that I started neglecting my own health. It wasn’t until I faced burnout and saw my personal relationships suffer that I realized success isn't just about pro milestones. I make it a point to set clear boundaries and delegate more. I've also made time for self-care an absolute must in my schedule. These changes have not only made me more productive, but I also feel stronger and more well-built. It's clear to me now—maintaining a healthy balance is really important for long-term success.
Thanks to Steven Rodemer, Rodemer & Kane!
#8- Making a product that didn't resonate
I once launched a product that I was convinced would be a market hit—a lavish floral arrangement designed for a niche audience. Despite my confidence, it didn't resonate with customers as expected, leading to disappointing sales. This experience taught me the priceless value of truly understanding consumer needs before diving into development. Engaging directly with my clients through surveys and feedback sessions has since become my cornerstone strategy for innovation.
Thanks to Kate Hill, Kate Hill Flowers!
#9- Not pre-selling
We recently tried to launch a new (digital) product. Projections were between $15-20k, but we made less than $3k. Before launching and building it, we surveyed our 20k+ email subscribers. Everyone said, “I want it!” But then they didn’t buy it. I learned that just because people say they want something, doesn’t mean they’ll actually swipe their credit card. Always pre-sell! (I’ve pre-sold before, but for silly reasons skipped it this time. Sometimes you have to learn a lesson multiple times!)
Thanks to Heidi Weinberg, Successful Fashion Designer!
#10- Managing people as opposed to workflows
As an entrepreneur, getting knocked down is a regular occurrence. I faced this when my business was doing well, but tasks were starting to slip through the cracks, and important items were being overlooked. Around that time, I read The E-Myth by Michael Gerber, which helped me realize the need for repeatable systems. By putting the right people in the right roles and organizing our processes, we stopped managing people and started managing workflows. Since then, our operations have become stronger, client satisfaction has increased, and the company has grown sustainably.
Thanks to Michael Mejer, Green Lane Communication!
#11- Launching a campaign too quickly
Failure is part of every entrepreneurial journey, and for me, one of the biggest lessons came from launching a marketing campaign too quickly without fully understanding my target audience. The campaign fell flat, and we didn’t get the engagement we expected. What I learned from that failure is the importance of research and preparation. Now, before launching any initiative, I make sure to spend time understanding the customer’s needs, gathering insights, and testing strategies before fully committing. It was a tough but invaluable lesson that taught me patience and the power of data-driven decision-making.
Thanks to Jordan Figueredo, Pelicoin!
#12- Spending lesser probation periods
One of our biggest lessons came from hiring an interim manager who, on paper and in
interviews seemed like the perfect fit. However, once in the role, it became clear that her performance didn’t meet our expectations, which ultimately clashed with our company’s vision and objectives. It also impacts our team’s effectiveness. We learned the importance of spending more time during the interview process to not only assess a candidate's skills but also to understand their values. We’ve implemented longer probation periods for unproven hires, providing a safety net for unforeseen issues.
Thanks to Max Milstein, Apex Tuition Australia!
#13- Failing to do rigorous analysis
One of the biggest lessons I learned from failure was during an investment in a tech startup. I was captivated by the innovative product and the charismatic founder, and I let my enthusiasm get the better of me. I didn’t dig deep enough into the company’s financials. The startup ran into cash flow issues, and eventually, it folded, taking my investment with it. It taught me to temper enthusiasm with rigorous analysis. No matter how exciting an opportunity seems, you have to get into the weeds—scrutinize every detail, question every assumption, & always have a plan B.
Thanks to Austin Rulfs, Zanda Wealth!
#14- Taking time to get the momentum
For the entire time I have been in business, which is coming up to eight years now, I have failed my way to success. It took me over a year to get the momentum of my business moving. Even today, the new projects we put in place sometimes take a few attempts to get traction – we make mistakes. It is not only the ‘new' projects but in today's fast-paced & continuously changing environment, the things that have worked brilliantly in the past are always evolving and changing. This means that you have to keep moving and improving. What I have learned is that any improvement will have mistakes with it. It is the creative, excited, and nimble mind that will help you expand.
Thanks to Suzana Mihajlovic, Your2Minds!
#15- Overlooking generation of valuable content
Early on, we focused heavily on building a visually appealing website, thinking that a polished online presence alone would drive business. But we quickly realized that without traffic, no one was seeing it. That's when we invested in our blog, creating content that addressed key client concerns like zoning regulations, approvals, and feasibility reports. The lesson? Don't just build something that looks good—invest early and fast into generating valuable content. A blog is crucial for visibility, driving organic traffic, and ultimately connecting with your target audience.
Thanks to Ryan Giorgiutti, EzFeasy!
#16- Forgetting my own power and what worked
I failed after achieving success, it happened because I forgot my own power, I forgot what really worked for me. I ended up listening to too much noise around me and took paths that were really not the best ones for me. The valuable lesson I learned is that everyone has their own unique superpowers, what is right for someone else is simply not always going to be right for you and whilst taking advice is important it's more important to ensure the advice you're taking and acting upon is actually in alignment with you. Finding what works for you and sticking to it is the most important thing.
Thanks to Jane Baker, House Of Motorsport Brokerage!
#17- Several failures
I have failed many times in my journey, but I have learned valuable lessons from each setback. Don't be afraid to pivot. Sometimes, the original idea or product is not what the market needs or wants. Don't try to do everything yourself. You need to delegate tasks, outsource functions, and hire experts who can help you grow your business. Also, don't neglect your personal life. Running a business can be stressful and time-consuming, but you should not sacrifice your health, happiness, or relationships for it. You need to find a balance between work and life and make time for yourself too.
Thanks to Lily Stoyanov, Transformify!
#18- Not doing enough research
One of the biggest mistakes I made was jumping in without doing enough research on a new market. I didn't realize how important it was to understand the local culture, and I made a product that didn't do what it was supposed to. The moral of the story? Get to know your audience before you jump in. Another mistake I should have made was hiring. I've come to understand that finding the right people for the job is more than just about what they can do on paper. It's about finding people who share your values and goals.
Thanks to Matt Little, Festoon House!
#19- Not shifting focus based on workload
In every business, there are ups and downs, but I’m determined to grow and learn from my mistakes. I lost 2 clients who’d only been with me for 1-2 months. On the upside, another client had to pause because I was getting her too many meetings. Now, I have learned to refine my onboarding process, and I’ll be regularly checking in with clients. What I learned was to shift focus each month based on workload, to plan out the day more efficiently, being selective with meetings, strategize with the team to be well-prepared, pick the right networking events. Also, ensure I’m working with clients who are the right fit. Life and business go on.
Thanks to Jordan Knight, Spicy Pineapple Marketing!
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