Whether you’re wondering how savvy entrepreneurs survive their blunders or looking for inspiration because times are tough, in this article we’ve compiled 103 micro-lessons that should do the trick. Over the years we interviewed hundreds of ambitious people out there putting themselves on the line. Obstacles come with the territory.
As you’ll discover when you start skimming, one thing they all seem to share in common is the ability to see an obstacle as an opportunity. Truth be told, we can’t control what happens to us and our companies, but we can control how we react, right? Enjoy!
I wasn’t always careful to have the right people around me. Financial and legal issues have never been my strong suit and, looking back now, I should have had a business partner who I could trust to handle those things. But I also made bad decisions about who I hired, and held on to staff I should have fired.
I had people on my team who stole from me and who leaked private business matters to the press. I also had people who weren’t good enough at their jobs to contribute meaningfully. Some of the staff I hired just weren’t really passionate about Skai Blue Media and our vision.
The lessons I learned from that mistake were hard but valuable. Now, I only hire people who are genuinely interested in my success and understand what we do at Skai Blue. They have to be the best at what they do so they can pull their weight and handle their strengths while I handle mine.
Anything less than that won’t cut it. I tell my staff all the time that Skai Blue is going to the penthouse and some people are going to get off at lower floors. I’ve learned to be okay with that because I understand now that your team will make or break you.
The obstacles turned out to be linked to the opportunities. We started the company in one of the worst downturns in the tech industry. That obstacle meant everything was on sale! People, equipment, office furniture, office space … some things we got for 5 cents on the dollar. We still had to find business, but even here obstacles were opportunities.
All the people I worked with at my old company were landing new jobs around town, and our startup story caught their attention and they started hiring our company to help them. Early sales were unnaturally easy to land because we had built up a good reputation based on our previous work.
Cash was still tight, so we had to be creative. We ended up creating a leveraged play model where we traded significant amounts of cash revenue for equity and royalty in the products we were helping other companies build.
This kept us busy and there was enough cash in every deal where we didn’t have to starve, and we were planting great seeds for future success.
There are roadblocks in every business no matter how well you plan or how hard you work. There’s no way to anticipate turns in the market, the economy or events leading to headwinds that feel like a jet blowing in your face. For that matter, nobody has ever built a great business without failure and roadblocks. It’s what makes all of us stronger. I don’t think of things as failures as much as setbacks. Either you learn from these setbacks or they can doom you.
For Fountainhead to finance SBA 504 loans, we have to be funded. I enjoyed great success in my former company, so it wasn’t hard to obtain startup capital for Fountainhead. Just a few months after opening our doors, we were set to close a significant capital round that would enable us to quickly go national in our lending ability. We did all the right things, but circumstances out of our control influenced the process and it took me nine months to finally close that round of capital.
It wasn’t rocket science. I got up every morning determined to make it happen. It probably took a year off my life, but I took on a bulldog mentality and refused to give up. That funding was crucial in scaling Fountainhead and helping more small business owners, so I absolutely wouldn’t accept failure as an option.
Every business has to have someone who will push and do whatever it takes to achieve what feels impossible at times. The person that will leave it all on the table to create a tipping point that changes the future. I knew that if I didn’t power through and lead, then Fountainhead would never become what I knew it could be. We’ll have other challenges, but if I hadn’t made it through the first one we wouldn’t be here discussing Fountainhead.
To me, the moment that you enter the startup world, the first thing you should realize is that being a startup means making mistakes. After making several mistakes, we learn to not be afraid of them anymore.
Because we know that we should always adapt ourselves to changes, changing becomes habitual. We discover that learning, investigating and changing is the nature of startups. And if you can change quickly, you shouldn’t be afraid of mistakes because you can recover from it easily.
However I can still name several mistakes that we learned a lot from. For instance, in the beginning we thought that our business should be B2C, business to customer, but soon after we realized that we offer more for businesses than direct individual customers. So we quickly switched to B2B and that brought us many new clients.
Also, our first and biggest mistake was that we thought our product could sell itself and growth would be automatic. So we published the website, launched our application, set pricing and waited for customers to come rolling in.
We banked on the uniqueness of our product, its capabilities and our pricing but forget to reach customers and gain their trust. Then we quickly realized that we should first introduce ourselves to them and build a relationship. After that, hunting became our new growth strategy and we win most of our customers from related strategies.
I mean, it might be good to make mistakes if you can learn from them and adapt yourself accordingly. So far, our mistakes have made us smarter and taught us a lot.
Two stand out — jumping too fast and having a scarcity mindset.
I’m fast in my decision making and thinking process. It helps me fix, adjust and be flexible but sometimes, I get too excited or jump into things too fast without diving deeper or waiting to see if that client would really become a client or not.
Now that I’m a year into the business, I get less jumpy about the decisions I make and always add extra buffer time for myself to think through my decisions to make ones. It also makes the decision process less stressful if I feel like I don’t have to do everything immediately which is how I felt sometimes early on.
Mindset is powerful. For a while, I focused on how to save money, resources, and energy. This caused me to step back from certain decisions and take less risks. But it wasn’t working. My saving would only save a little. It was only when I started to change my mindset as an investor and marathon runner that I saw more opportunities to grow than to save.
As someone told me ‘you can’t expect to grow without spending,’ I realized my attitude of wanting to save too extremely early on was the cause of limiting my growth. As soon as I changed that mindset of abundance, I have not only felt more free and reflective but also made decisions that made direct improvement in my business.
Abundance will come to those who think and live like they have abundance. Note, this is different from thinking that you have the abundance of money. That’s different.
A little more than a year before getting into real estate, I started a satellite dish business. The first few months were great. I was making more money than ever before. After working the #’s, I figured out a plan that would make us 1M over the next 12 months.
So I got a business partner, a big office, lots of staff and we set out to make this plan a reality. One year later instead of a million dollars, I had $120,000 in debt, a partner that was stealing from me, and a failed business model.
Looking back it’s hard to say EXACTLY what the biggest mistake I had made and honestly that experience is a huge part of where I am today. So I don’t want to encourage people to be overly paranoid. I think the #1 thing I could have done differently was to be more open and direct with people. I was so afraid of “conflict” and therefore did not address concerns as soon or as directly as I should have when they arose.
The plan itself was still solid but I should have been more direct (or broken up with sooner) with my partner when he always was late to meetings and didn’t follow through with commitments.
I could have been more direct with the sales guy who worked when he felt like it therefore messing up the schedule for the installers and I could have been more open and direct with the recruiting manager who didn’t have one person ready for our summer sales program.
Leadership is probably the #1 attribute you need to succeed as an entrepreneur. Sometimes, that includes having needed somewhat uncomfortable yet crucial conversations with those you work with. This might be a partner, loved one, employee or vendor or contractor of sorts. Sometimes we feel like when we give someone direct, open and honest feedback or constructive “criticism” we are being “mean” but what I have come to find over the years is it is actually more mean when you don’t, because it never ends well for either of you.
Having those conversations sooner than later allows them to grow and develop or helps you each to realize it’s not the right fit sooner than later.
I doubted my own abilities. I didn’t believe in myself. As a result, when I first started my own business I looked to, in fact paid, other people to tell me what to do. I assumed that they were better and smarter than me.
After wasting a lot of money and time, I figured out that they weren’t any better or smarter than me and I didn’t need them. This is different than hiring a business coach, which I eventually did do. My coach didn’t tell me what to do. He asked me what I wanted to do and then helped guide me to do what I wanted to do. This allowed me to build the business I wanted, not what someone else wanted for me.
Initially, I wanted Papilia to be an app. I was fixated on the idea that I had to build an app. I kept telling people Papilia was going to be an app, and they were waiting for it to be released. The fact that I don’t have a software development background was hindering the development of Papilia.
To overcome this issue, I went back to the drawing board. I worked within my technical capabilities and turned Papilia into an online web service which allows me to create a more personalized experience for clients.
I do not see this other issue as a failure, but a deeply personal issue I am working to overcome. Earlier this year, my Mom passed away unexpectedly. I was not able to meet goals I had set for Papilia for obvious reasons.
But, I have learned to take each day as it comes, to embrace the challenges and to act upon what my Mom always advised me to do: work hard, stay focused, and to be fearless.
The biggest roadblock to date has been trying to open the doors of partners that can contribute to our growth. This has been difficult because we’re early-stage which most potential partners view as higher risk. In addition to that perceived higher risk, our ambitious goals usually lead potential partners down the road of believing lower probability of success. This reality makes it very difficult to solicit the support of partners in the early stages.
The way Xcellent Life has progressed past this reality is a change in mindset, so that my focus is squarely on doing everything that I can do and that we can do to move forward toward our vision and not look to seek the assistance in the same way. Now, I progress and provide updates to targeted partners.
As we move forward, our persistence, tenacity, and ability to execute provides more leverage to bring those desired partners to the table. Those partners generally recognize the underlying attitudes and company attributes that lend to success, in particular in the absence of having plentiful resources or capital. In short, control what you can and move forward with an unnatural tenacity and don’t worry about not getting the help you think you need. Just worry about what you can control and everything else works itself out.
The list of that is way too long. From people not understanding our value and thinking we weren’t worth anything to people thinking it was very easy to copy. That was a pressure we faced a lot before we built a brand and ran programs at places like MIT, Harvard, and Stanford.
We definitely got punched in the face by roadblocks and obstacles. But in the end, they always seemed to benefit us and make us better at what we did. We had competitors who seemed to be growing faster, but we just kept our heads down and kept focused on being the best at what we do.
The biggest mistake I’ve made in business is trying to grow too fast. It’s easy to get caught up in the next thing and miss out on what’s right in front of you that needs to get handled. By focusing too much on the future, it has, at times, drained the energy from my business.
It’s key to acknowledge the timing of where you’re at and not move too slowly or too fast. Just keep incrementally growing. Don’t try to scale before you’re ready. Timing is everything.
Biggest mistake: not creating a sales funnel early on.
Right out of the gate, I landed a HUGE client and was “set” for several months. But I was so good at what I was doing, I worked myself right out of a job (which was the entire point). Unfortunately, I hadn’t been actively working to attract other clients during that period, and when the job was over, it was like starting from scratch, but much harder.
You need to be constantly putting clients into the sales funnel to set yourself up for success. A lot of people will be “just about to sign” with you – which could mean two days or more likely – six months. Never count on anything being a “sure thing” until you have a signed contract or a cleared check in the bank!
Finding our North Star and owning it has been the toughest decision along with the business structure. You have an idea of why you’re going into business and where you want to go, but the “how” takes time to solidify.
Making the decision to hold-off on defining Let’s Vibe and legally forming until we matured as a solid pilot was very tough because it caused discomfort to be “uncooked” while everyone wanted to consume us and our value. This made me and my team much better by teaching us patience.
PATIENCE. Patience preserves time, energy, financial resources, and sanity. It makes you a better listener, student, co-founder, service provider, leader, and person overall. Creating value takes time. Creating sustainable value may take even more time. Patience, boo. Patience.
The interesting thing about living in a country as large as the US is that you come to understand that we have a lot of stereotypes and inherent geographic biases when it comes to sections of our country. Being headquartered in the South and with our first three centers located in the Southeast, we had to initially overcome the preconceived notions that the talent in our smaller cities wouldn’t match the talent found in the larger metro areas.
What we found and what we’ve proven for our Fortune 1000 clients located in those metropolitan areas is that there is exceptional talent spread all across our country. I do occasionally have to remind our clients and prospects that Bill Gates got started in Albuquerque, New Mexico, home of our 4th software development center.
Many of our colleagues have worked in large metro areas and for some of the world’s most recognized brands. Yet they have decided that they prefer the quality of life offered by these smaller cities. Consequently, at RSI they get the best of both worlds – an exciting career in software development working with the latest technologies and the quality of life afforded by living near the Gulf Coast, the Sandia Mountains, or wherever they grew up.
We have certainly made a lot of mistakes. One of my biggest failures wasn’t having the proper paperwork in place to protect me and getting ripped off by some former business partners for 6-figures. This setback was absolutely devastating at the time and I was at the point where I didn’t think I’d be able to recover.
Luckily, I now look back at that incident as a blessing and accredit it to the journey I’m on now.
Learn from my mistake and also think about what the most important part of your business is and how to protect it. We now have a locking mechanism that occurs with a user who switches multiple state forms. This prevents would-be competitors from mining data and processes from MissNowMrs.
We have had failures. We’re not perfect but we are constantly improving. The best way to overcome a failure is after things settle down look at the source and ask why did this happen? I will be the 1st one to take responsibility. In this case, we would have a discussion with our leadership team to review all the steps taken that caused such a failure, then we will change the process, improve and move on.
I think the biggest mistake in anything is to become complacent.
At some point with Young Slacker, I stopped producing good content and was posting less often. People weren’t entertained as much (maybe because they were now holding my stories to a higher standard) and engagement numbers dropped. I had to rethink my strategy and get back on track with quality content.
With Flux Chargers, since growth was so unpredictable, we weren’t fully prepared when we went viral. Our inventory was running low and our supply chain logistics weren’t optimized. We struggled for a couple months with low cash and low inventory. We eventually solved this problem but we could have done that so much quicker. We learned the lesson (which cost us a lot of sales) and we’re now fully cushioned with inventory.
My biggest business mistake was waiting. Not taking action and just thinking “If I build it, they will come”. That vision of dropping a piece of content and then having it go viral was always something I thought would naturally happen.
Also, thinking I could do it all by myself was a big mistake. I made strides with what I was learning, but once I got around people who were playing the game at a higher level than myself, I was able to really advance forward and experience true progress.
What you do not have expertise in will be your most expensive mistakes.
As a nontechnical founder, I had to take outside advice on tech platforms that we were forced to scrap over and over, which cost time and money. Advice is given through a highly biased lens it’s that idea that surgeons advocate cutting; therapists suggest talking; and pharmaceuticals recommend chemicals.
Ultimately, the CEO must make the final decisions and be accountable for those decisions, so she has to learn how to make the most informed decision, even if she doesn’t have all the experience personally.
So I learned quickly that most advice is not useful, and the best advice comes from those who have continual skin in the game you’re playing. I also recognized that owning that accountability is hard, but crucial in an organization.
The biggest challenge I have as a business owner and entrepreneur is balance. As I work on the business to continuously market and network for business I need to also have time to work in my business on projects. And since I am a home-based business, I also have to balance work and life. It is real easy to get caught up doing work vs. spending time with family and friends.
Another challenge is working solo. Without a team to bounce ideas off, help you get out of the weeds, or see other perspectives, it gets lonely. To combat these challenges, I have my business coach, am a member of Vistage, I started and run a women’s networking group and am an active member of a professional women’s organization.
I also frequently reach out to business colleagues that have become good friends for idea generation and support; and I have outsourced services such as a virtual assistant and bookkeeper.
Splitting with a co-founder very early on in the life of the company. Something that took me years to reconcile, honestly. It happened to be the best decision for the both of us, and the company, and so I don’t regret it.
That said, we sometimes forget that at the end of the day we are all human. Going through difficult work situations can be stressful. It has taken me a long time, but I’m much more careful now to appreciate each individual in their entirety – not just for what they do (or don’t do) for the company.
A few months in to starting my business, I partnered with a small, local agency. Although I intuitively knew it was the wrong move, and I never felt like they had the client’s best interest at heart, I spent almost a year building accounts under their business and wasn’t able to use that work as examples, even when Facebook wanted to recognize the achievements of one of the accounts.
Although it wasn’t the best experience, my partnership with another agency taught me about trusting my instinct and staying true to myself even if financially it’s tempting to make a deal.
The biggest struggle will always be that little voice inside your head that tells you your not good enough, that the idea is stupid, that you will fail, or that you will be laughed out of the room. The voice in our head can be so darn mean!
Quieting that voice, believing in yourself, and truly knowing your power is a constant journey that every entrepreneur is on. Recognize that there isn’t a one-size-fits-all solution to self-confidence but rather something you have to work on each day.
No entrepreneur or creator can create a successful business or products without taking risk. A risk does not have a guaranteed or known outcome, but with experience and the right ingredients, one can take calculated risks. In a traditional sense, an entrepreneur has to fail to succeed, otherwise they did not take enough risks. Failure can be on a small scale, that gets refined to reach success, or sometimes on a larger scale, where one looses a business.
No matter what the scale of failure in a traditional sense, one should be able to learn and keep evolving and innovating. My entire career has been about taking risks, evolving, refining and keep moving on to create better businesses and greater products.
My husband and I were six figures in debt and striving to change our finances by learning to live an extremely frugal lifestyle when I started my own business. This frugal mindset carried over to my business. I was afraid to spend any money and tried to learn everything on my own. I thought I was smart to use YouTube and Google to self-educate but I was actually stifling my success.
Now, I have the opportunity of sharing with others how frugal living almost killed my business and encourage them to make wise investments into their success. From this, I am fortunate to see the bloggers I mentor reach success much quicker than I did.
Tenzo is relatively simple. But, there have been challenges related to hiring and the business model. We were much too diversified in the beginning. Instead of doing a few things really well, we did a lot of stuff okay. Let me be the first and last to tell you – average work does not grow a business.
The Tenzo Team believes in the process of “iteration” and the “iteration cycle”. From top to bottom, no process in the company is perfect. We can always get more information or become more skilled in order to make better decisions and work more efficiently. This philosophy of iteration is all geared toward providing the best drinking experience in the world.
ACCESS is different because the staff isn’t paid. It’s run completely on volunteers. All the board members, advisors, and day to day managers work for free. In the beginning, it was difficult to get work finished because it’s not practical for everyone to spend significant amounts of time working on something with no financial return. Gotta keep the lights on. Although, I have to say that because of our great team, everyone has bought into the mission so this isn’t too much of an issue anymore.
Funding was big problem for me, as without any corporate sponsors or partners, I lacked the financial resources necessary to sustain a nonprofit. So, I began reaching out to various small businesses and applying for grants, and after seeing much success with this, I’ve been enabled to expand my nonprofit and broaden my horizons.
We thought raising VC money was going to accelerate our business. Actually, it almost killed our startup. In the end we learned that building a real business with real revenue is all that mattered to survive.
I think most entrepreneurs give up when things become hard. You start to doubt yourself and you can get into a death spiral. It’s important to understand that you will always fail. Once you learn that, you won’t be afraid to go out there and take risks.
I think the toughest part of Freelanship has been finding a good and reliable co-founder. It can be wildly difficult to find someone who is as passionate as you are about your baby.
I have zero interest in learning to code. I’ve tried and hated it numerous times. I just can’t get into it. That’s definitely a problem too since getting a custom platform built requires mad money – like around $100,000 – and that’s on the low-end of quotes I’ve received.
To solve my co-founder problem, I utilize my rich network of brilliant friends and mentors, who are 1,000 times smarter than me. They help through any and every technology issue.
As for the platform problem, I have a solution in the works. Stay tuned. (Remember, be resourceful when you don’t have the resources.)
I’ve made a few hiring mistakes along the way. A couple of years ago, we hired someone who disappeared on us just after 2 weeks of working with our clients. I had to scramble to find replacements, and I offered our services for free for a month as an apology for the terrible inconvenience. We’ve refined our hiring process so much since then!
The costliest mistakes so far relate to paying people who didn’t deliver. I won’t go into details, but on the flip side, this past summer I had a college intern who was absolutely amazing – better than many people I’ve worked with who’ve graduated with years of work experience.
I think one of my biggest mishaps was hiring a designer that wasn’t aligned with me and had a very different communication style than I do.
It was an expensive and emotional lesson, but I learned the importance of discovering communication preference and style prior to hiring and outsourcing. This has helped tremendously as it allowed me to find a phenomenal online business manager and virtual assistant that feels fully aligned with me and my business.
Don’t try to be everything for everyone. Find your niche and really excel at that. By trying to accommodate an offering for everyone, you tend to dilute and diminish the strength of your offering, and ultimately, your brand.
We built too many features of Admit.me too fast. We should’ve built a more basic product, gotten feedback and made improvements after that. It left us in a more challenging situation, but we learned from it. It seems obvious and easy to execute, but it actually takes quite a bit of discipline because you are constantly comparing your product to more established products from more established companies. Don’t do that.
Other than the “time demon” which we all battle, the challenge I struggle with is bridging the gap between vision and boots on the ground execution. Between falling in love with the problem you are trying to solve versus falling in love with the solution.
For any entrepreneur or business owner, the real challenge is to solve the customer’s problem, hopefully with a solution that makes money. But it’s the problem – not your vision or solution – that is the core issue.
So my advice to future entrepreneurs is to focus on the problem you are solving, not the solution that you are convinced will work! If a better solution comes along, be ready to rip up your business plan, adopt, adapt, and move forward. It will be better for the customer – and that means better for you and the company.
Our biggest struggle is managing growth. We went from Brett, myself and my mother to 53 employees so quickly. We went from a customer list of Mom and Pop shops across the country to box houses and retailers across several continents. It takes a lot of planning and a few leaps of faith to make things happen at this speed.
Hiring the best people and working with a good banker that can see your vision is always a must.
I can think of two mistakes that taught me powerful lessons: Rushing things and trying to set concrete expectations instead of flexible ones.
When I rushed to get my first domain name up and running, I felt really great about it; as time passed, I realized that I could’ve waited a little longer instead of having a domain name that is now hard for me to use the way I want to.
It’s not the end of the world, but at the same time, now I find myself stuck with trying to figure out how I can best use this domain or I’ll basically just have it sitting there. This experience ties in with setting concrete expectations, the reason I chose the domain name was because I had created a vision of where I was heading without really knowing what was to come.
When you’re an entrepreneur driven by your passion to help the world, you can’t necessarily give it shape and actually all the entrepreneurs I’ve met along the way have gone through the same transformation. They started out with a set idea and then found themselves in a totally different place they thought they would be.
I call these mistakes, but essentially they are life experiences that help us remember to keep our heart in the forefront and to trust that the shape of our business success will show itself in time. Step-by-step actions and trust in what I want to achieve with my business are the lessons I gained from those experiences, “mistakes.”
Relying on one large client who, as their needs grew, made it both impossible, as well as unnecessary for us to continue developing our demand pipeline. This made it so that when the inevitable slowdown on their end materialized, we had to hustle to avoid shrinking too much. We’re still working on preventing this in the future in order to be more diversified and resilient.
For me, it was going into business, my first dog company. Going into business with people that I trusted without getting it on paper. Basically giving them the benefit of the doubt and not ensuring that my best interest were also being taken care of. What I learned from that is A), you’ve got to do that. Trust is something that has to be earned but it should always be only to a point.
At the end of the day you have to make sure that you’re covered. You’re basis are covered legally. In terms of what deal you’re getting yourself into, what the expectations of you are, and what your expectations of everybody else is. It has to be very very clear cut before you ever agree to do anything.
Don’t go into anything with it just, “yeah it seems like it would be a good deal. Everything will work out and we’ll figure it out as we go.” No. Make sure that you understand everything of what’s going on and what the agreement is before you sign and get into business with somebody. Whether it’s a single contract or a business partnership and everything in between. Make sure that you understand what’s what.
The biggest thing I struggle with as a business owner is time management. I have a hard time saying no. I am a people pleaser. Because of this, I get roped into a lot of projects that sidetrack me from my businesses.
They are all great projects, but I have learned saying yes to everything leaves me little time to work on my own business. Without my business, I cannot help others. So I am getting more careful about what I say yes to now.
My advice for a future star is to take care of yourself first. If you don’t take care of yourself, how can you take care of anyone else?
To say what happened to us was a mishap would be an understatement. We watched the business we had built with blood, sweat and tears over ten years nearly get destroyed in ten days by the financial crisis of 2008. It took us two years of 20 hour days to save what took ten years to build.
And it was really my change in perspective that was the difference between us succeeding and us failing. Looking at problems differently under the greatest of pressures – much like the pressures that all entrepreneurs feel – was really where all the fixes came from.
The biggest lesson I ever learned was “Don’t take your eye off the ball”. Back in about 2002, we went through a big change in my consultancy business. We grew to about 12 staff and I pretty much handed the reins for things like book keeping and financial management to other people while I tried to focus on writing code and customer relations.
About a year down the track, I realised that financially, we were in a real mess, and owed the tax office a large debt. To be fair, it wasn’t really the fault of the people I let take charge. It was entirely my fault for ‘delegating by abdicating’, rather than making sure that they were making the right decisions and doing the right thing long term.
We recovered from that, but it was a lot of hard work and stress, and since then, I have promised myself to always stay on the ball and keep an eye on all aspects of the business. It is so easy to ignore or de-prioritise things like book keeping and invoicing, especially if you don’t enjoy doing it (as I don’t). But a good business person, in my opinion, has to make sure that they spend the same amount of care and energy on things they don’t enjoy, as well as the things that they love doing.
The biggest mistake that I have learned from is making sure that you be very careful who you let in and around your business. People will deceive you. They will subvert your goals and intentions to better their own path to success.
It’s the Machiavellian characteristics that you learn in upper division management class, however, systematically ensuring that you vet every person that you let into or around your business is a learning process.
I spent 6 months studying my intended target market before launch. Developed branding, marketing message and media around said market. Half way through our first year, I observed that of all the customers we had, not a single one was from our targeted market.
Somehow we managed to grow a business doing it all wrong. I immediately began surveying our repeat buyers and studying their traits and habits. This allowed us to literally rebrand, not only the look but the services we offered and products we produced, right in the middle of the season. This experience totally shifted how we approach the business and our customers.
At the beginning of the year, we lost 30% of our revenue in 60 days which has made us become very lean and mean. We’re a bit smaller now and much more of a family. It hasn’t been an easy year but we’re still providing killer results for our clients and our staff is all in it together, and that makes me so happy.
I typically view mistakes as lessons-learned. There will always be trial and error throughout all the stages in business. However, my greatest lesson learned was to find a niche market to do business in.
At one point, I found myself marketing my services to various industries that I technically wasn’t considered a subject matter expert in. But the key here was I identified quickly that I needed to find a few industries to do business with as opposed to opening the door to any prospect who called or inquired about my services.
Everyone faces failures, obstacles, and adversities in life. The question is not will you face failure in life, it’s about how you choose to handle it. It’s all about your perspective of the situation. You get to choose! You choose how you respond to what happens to you in life.
So like everyone else, yes, I face adversity and obstacles and failures but I choose to utilize those times to build character, learn from it, and WIN more in life. I have been through crazy situations when most people would have folded, but I am only the man I am today because of these situations. What challenges you, will change you. The difference is, I have a game-plan in place on how to WIN through adversity. Most people are not prepared and when adversity hits, they don’t know how to breakthrough and create a WIN.
It starts with your MINDSET which leads to your ATTITUDE which determines your ACTIONS which creates your results and ultimately your life! So if you want to WIN through obstacles and adversity, have a game-plan in place to train and prepare when it comes.
We’ve been very lucky in that we haven’t made a whole lot of mistakes. When we do make a mistake, we own up to it quickly and fix it as soon as possible.
There’s a saying that goes, “When you win, use ‘we’. When you lose, use ‘me.’” I like that saying and think it fits the Istation culture well.
My biggest mistake was to publicly launch a product before establishing “product/market fit”. Marc Andreessen coined this phrase to describe the discovery phase of validating a product concept, the market potential and the actual market acceptance of the product.
I learned that confirming that a market exists and that customers will pay for your product is an essential part of the product development phase. It’s the reason companies launch a beta version of their product. This gives the company a chance to evolve their product based on the direct input from their paying customers.
Trust is a big issue for me – I always think the best of people, and by moving from a small country like Denmark to the US, I had to adapt.
I come from a place where a person’s word is worth just as much as their signature on a contract. Most of my mistakes have come from trusting the wrong people – from a shady landlord to a potential customer who turned out to be an incredibly talented scam artist.
Every episode has taught me to be more careful, and I have learned from every single one.
Early validation, we did not ask potential students what they wanted, we basically decided for them. Many of them struggled with some of web development courses. But now, we know most of them were looking for the easy way out and that is what gave birth to CT4B.
My biggest mistake was trying to copy what other people had done too much. As I mentioned above briefly, I had role models, and I would try hard to copy their style, rather than develop my own. Wealthy Gorilla is now my own style, and that’s made all the difference!
The biggest mistake I made was definitely that at first I was afraid of failure. I didn’t want to be a failure and not live up to the hype I was creating around my business to friends and family. I was afraid to cold call/email people to buy a website from me, this is something I quickly realized was a huge mistake and something that is a part of business.
It is essential to understand that failure is likely, but you have to keep moving forward for the vision that you have for your company. You have to move on, make decisions, and pitch the sales you need to pitch.
Sometimes, I wasn’t always focused and I caused myself unnecessary heartache! If you spread your message over broad waters this can sometimes be frustrating and take much longer to see results. It’s important to target efforts properly to those who really want what you’re offering.
Not hiring fast enough. In the beginning as a founder, you have to wear many hats but as soon as you can afford to hire more people you should definitely do so. At the end of the day, your team is your company, you should focus on hiring the best candidates and fast, they will help you grow.
One of the early ones was around fundraising. After winning the best music tech company at SXSW with only the beta version of our product, we spent most of the next six months talking to wrong stage investors and giving the wrong pitch. I wasn’t getting help from other people who had been through one or more rounds of fundraising and consequently took much longer to learn.
In the startup world, time is your enemy. The faster and more effectively you and your organization can learn the more successful you will be.
For me, it was remaining as a partner in the law firm I co-founded far too long. My passion wasn’t there. Far sooner I should have followed my instincts and the advice I gave others to create an exit plan and execute it!
My biggest business mistake was scaling EnvoyNow before fully locking down product market fit or unit economics on each order. We were so concerned with “growing” the business to show numbers for existing investors and potential new ones that we ignored some seemingly minor inefficiencies at the scale we were already at.
Therefore, when we added more campuses, more drivers, more managers, these inefficiencies became massive issues within the business, draining a lot of cash and a lot time.
The whole idea that I would build this business without leaving my home was a joke. That year, I only made $12,000. Then at the end of the year, I got invited to speak for the very 1st time at a luncheon. I said Yes quickly before I could change my mind and during that 20 minute talk, I made a $97 offer and had 21 people hand me money.
I realized at that moment that speaking provided a different level of relationship and that I could get new clients and make money quickly through speaking. At my 3 day event a couple of years ago, I sold $300,000 in coaching programs from the stage. I knew at that moment that this was my sweet spot.
I’ve made a lot of mistakes. I’d have to say that my biggest mistake was going into business in the past with partners that didn’t share my values. Seems pretty obvious, but when you have a great idea and a product that’s in high demand and starts making you a lot of money, it’s hard to step back and say, do I really want to be “married” to these people? I found out the hard way: it never ends well.
Of course this was way before I started EcoPlum. I’ve worked with like-minded people since I entered the social enterprise space.
I started my business after getting fired (on my 39th birthday) and had to overcome numerous obstacles in the first year including having our original investors back out (after 90 days) dealing with a cancer (melanoma) as well as a $15,000 embezzlement (supplier). And it didn’t get any easier in year 2 when I had to buy out my business partner which almost destroyed the company.
Several years later, we had to deal with a $250,000 employee embezzlement (accounting manager) on the “Day My Business Almost Died”. Some of the ways that I fixed these problems was to not to dwell on them and keep pushing forward.
I also was fortunate in hiring some really good people through the years who have been by my side through the difficult times. Since those days, I also adopted the mantra that “if it doesn’t destroy you it will make you stronger”.
I face challenges every day at Fitzroy that we have to overcome. The challenges are part of what make my job fun and get me excited to go to work in the morning. We’re working on a giant puzzle and every day we work on a new piece of that puzzle.
It’s not to say that there aren’t setbacks and disappointments but great things take time. Rejection and failure are things everyone deals with and your job is to push through them to keep building. What helps me is listening to or reading interviews with people who I admire, talk about their failures – it’s inspiring to hear about the struggles people have had to endure to get to where they are now.
Every month, we face new and exciting challenges at cove. We started with two people and have grown to nearly 100 full- and part-time teammates. I always tell my team that a mistake is not actually a mistake the first time—it’s a learning. We try to have learnings, but never mistakes. Learnings are an important part of any growing business.
The single greatest failure in all of our lives is not trying.
My failures include not trying to freelance sooner. Not applying to speak sooner. Not writing my book sooner (coming out in January!).
The conventional failures I’ve racked up are far and wide but I failed because I tried – and the trying, is what I celebrate.
Oh, the fact that I didn’t record processes, failures, and successes while initially building my company and working with clients. Now even if we’re a very small team, we record each step of our activities so we don’t make the same mistakes.
Many people don’t need this as it’s so corporate. But I believe this is the biggest less we should get from corporations. Learn how to write out your process so when someone new comes into the team or when we need to do things again, it’s much easier.
Too many to count. I’ve had investors sign documents and not wire money. I’ve had investors invest and then immediately demand the money back and threaten to sue. I’ve had customers sign and not pay. Just keep calm, and navigate the political waters. Don’t get angry, and don’t let others pull you down.
The biggest business mistake I made was miscommunication. We almost set our beta launch back a couple weeks because of miscommunication with our developer. I have learned that it is very important to be super clear when explaining specifics that you want done for your business.
I learned that I have to let go a lot more and trust my team to deliver the talents they truly have without interruption. In this regards, I see myself as a conductor in an orchestra and I need each sound to play their own part for the overall symphony to work.
We haven’t faced any major failures that have haunted us. I would say our biggest failure is our inability to discontinue work with clients once they’ve outgrown us. We need to push our clients to hire internally when they’re ready instead of holding onto us. At a certain point, they need someone internally who can drive the programs.
I think like many business owners, one struggle very often is when there are not enough hours in the day. I think another struggle is coming up with ways to get in front of the audience we need to be in front of where potential clients would be.
There have been many, many mistakes so it’s hard to pick out just one. Most fall somewhere in the category of not listening/communicating effectively. Ultimately, I believe that the root cause of many mistakes (if not most) is the failure to listen carefully and think before reacting.
Most things we do fail. We’re probably at a 1:5 or 1:8 success-to-failure ratio in all facets of the business from production to sales. But that’s just the startup lifestyle. It’s all trial and error until you find what works.
Once you figure out what works, do more of it. It’s that simple. When it comes to enduring the failure, then I usually lean on my answer to the above question.
Business arrogance kills. I have found that in periods when I rested on my laurels and thought that we were in the cat bird’s seat, bad things happen. At TechCXO, we incorporate an attitude of always learning. If we are not at the top of our game, others will come along who are and they will take your business.
Over-promising and then under-delivering. You need to realize early on, you need to solve your customer’s problems and meet expectations. Once you know you can, then slowly over-delivery while keeping expectations the same. This produces great work, and something clients will not only love but keep coming back for.
I think every small business goes through start-up pain and that there’s a steeper learning curve than they anticipated.
One of my struggles was narrowing the focus of my marketing services. I have over 20 years of experience and tried to communicate too much. It’s overwhelming to clients and they don’t have a clear picture of how you can help them.
To change that, I thought about the aspects of marketing that I enjoy the most and focused on that as our specialty.
As I narrowed my business focus, I also revised my target market to coincide with the change in strategy.
Myself. I’m my own worst enemy. Every day I have to work on myself, question my own beliefs and expectations, and make sure I’m not getting in my own way.
Life becomes a whole lot easier when you realize that you are in complete control of what you choose to do, and that what you choose to do is what will determine your future results.
Once you understand that, the only thing you need to do is get to work and be patient, knowing that if you do the right work, you will get the right results.
We’ve had many failures, the most recent of which was losing our funding to manufacture our product and having to wind down the business for almost a year until we could find the capital to re-launch. Once again, we overcame this challenge by listening to our customers who told us that if we launched an updated version of the product on Kickstarter they would support us.
And sure enough – they did. We had one of the most successful campaigns in the history of Kickstarter and we may not have gone that direction without the encouragement of our customers.
Taking on too much responsibility at once. I am the first one to volunteer to do something, even when I know I can’t realistically get everything accomplished. Eventually you become overly stressed and just can’t operate at your best.
I’ve learned to delegate, and to manage my time more efficiently. It’s made me hyper focused on the tasks at hand, and I now weigh out the pros and cons before taking on a new venture.
I started Inkwell with the intention of helping people find greater work-life balance—but sometimes I don’t live that balance very well! I’m working on overcoming this by setting better boundaries and taking unplugged vacations with my family.
It’s hard to have boundaries when it’s your own business and you are really invested in it. What do you do when you’re on vacation and a great opportunity comes through? Keeping boundaries, and knowing when to let them go, is an ongoing challenge.
Two things come to mind.
I stayed in a business partnership out of a sense of obligation to a partner who helped me get started in the business. As I began developing a clear vision for Arizona Partners and securing my own clients, she went in a different direction with her own vision for the business.
I trusted that the natural order of respecting each other and the differences in our goals for the business would transition our business relationship and it did. She went on to develop her own business and I kept Arizona Partners and secured new partners.
I didn’t protect my idea and ownership over it well enough. I definitely appreciate the contribution everyone who has been involved with AK Kerani has made to its growth. However, I wish I had been more confident and discerning about what the company needs instead of opening it up to others’ involvement too soon.
I think some of my decision to make AK Kerani a collaborative venture stemmed from being on a college campus as opposed to my more solitary current environment. However, some of it was insecurity and the lack of a strong sense of self. I felt that my business was only valid if others were a part of it. Now, it’s become such a strong entity on its own that I know exactly what it needs and who I need to contribute on a contract basis.
Starting anew, I’ve learned to ask for informal feedback way more regularly but at the same time have committed to keeping internals private until the company is ready to formally expand.
The biggest business mistake I made was hiring someone to help them out when they weren’t quite a fit for the role. It’s great to help a friend but not at a detriment to your business. I had to do a LOT of extra hand-holding and my productivity and the community suffered for it, as did our personal and professional relationship that had before been so strong before.
Since then, I’ve really honed in on the type of employee that is the best fit and have hired based on factors – and not my past relationships. Mistakes like this always remind me to adapt, find a new way of looking at it, and keep going. Cheers to your own failures. May each one bring you closer to success!
My biggest mistake was hiring the wrong person. Ultimately, the experience taught me that (1.), I can make mistakes and still be successful and (2.), that it was just the miss-step that I needed in order to know exactly what type of person I needed to hire, and of course, finding her!
Debt. Debt destroys a business. It has been the biggest mistake I have made in any business. Debt is not the answer, it is not the key, it is not the way to go. Learn to operate your business with no debt and that is where true profit begins and grows. I only operate Frugi Home Organizer debt-free and I encourage all our partners to live debt-free.
Around 2012 or 2013, I went on a vacation and noticed tons of people reading online publications on their phones and tablets. It was something I could see being really valuable for small business owners, so we decided to create one of our own, a digital magazine called Onward.
We spent a lot of money on the app and the design of the magazine. It took so much work putting together the content every month, and it just never took off.
We finally took a step back and looked at the big picture. We liked the idea of this online publication, but it had turned out to be a drain on our resources without a lot of return. I decided that we’d gotten too far off course, too far from our niche, so we closed it down.
Sometimes, as a business owner you have to be ok with walking away from something that isn’t working. You’ve got to choose your battles, and that wasn’t the battle we wanted to focus our time and money on.
Taking a client that I knew had a reputation for being difficult in ways that I knew I couldn’t control or get past. I got over confident, in thinking that I could conquer the obvious issues. Sometimes you have to know when to say “pass” or “no” instead of shooting off your own foot.
If you hold on too tightly to a tarnished object, it will drag you under and destroy you. The particular client I am thinking of set me back 6 months on another more promising and profitable project. I am more careful now.
When starting a business, you realize VERY quickly that EVERYONE has an opinion. What you should be doing, what you shouldn’t be doing, who to do it with, what to wear while you’re doing it, etc. The best gauge for who has final say in your business is the person that you are looking at at 3AM getting things done.
Trust the gut and expertise of your core team because while there are experts for every stage of your business, YOU, too, are an expert for your business (don’t marginalize it). Do not make costly business decisions based on advice solicited or unsolicited from any person who is not in the trenches with you.
As entrepreneurs, specifically because you’re moving a mile a minute, it is so tempting to accept offers that are “too good to be true” – 99.9% of the time it is exactly that! Don’t fall for immeasurable help that comes with a cost, any cost. Trust yourself (after all you’ve gotten this far)!
Every experience and encounter has improved our business acumen and has help us to seek multiple solutions before landing on one.
There are always obstacles along the way for any entrepreneurial journey, and you must find a way to overcome them. At first it was hard to sell the idea to others, because the show had never happened before and there was some skepticism. After making a deal with YouToo Cable, that changed everything. Hard work, drive, and passion for the project put us on top.
Not exactly a failure, but sometimes it’s hard always being “on the clock.” As an entrepreneur, your company is 100% your responsibility. There’s no room to point fingers at anyone; everything is on you. Therefore, I feel compelled to always be connected. And in this day and age with technology, it’s easy to always be plugged in.
But always having your earphones in and email up isn’t healthy. I think sometimes we’re programmed to see people who are always working as hard workers. That may be the case, but constant work doesn’t mean constant quality. Instead, pick and choose your times when you work and put in the best quality.
One of my New Year’s resolutions was to not check email after 8 pm! I’ve also grown to a point where I could hire a team of staff so I can focus on growing the company instead of just continuing to maintain it.
I realized just running myself into the ground with work and responsibility wasn’t helping Headbands of Hope grow. Instead, I needed to focus on quality of work versus quantity and hire when it hurts. When our wholesale partnerships with stores started significantly increasing, I hired a Director of Wholesale.
However, I still do all the graphics and social media myself because that’s something I feel that I can manage and that I excel in. Don’t just hire because you can. Hire only when it hurts.
I started my business with a partner. I lacked the confidence to do it myself. That was a disaster, we had different expectation and priorities. I bought her out and built the business the way I felt was best.
I learned not to completely rely on someone else. But I don’t do it alone – I have a great virtual support team who handles customer support, newsletter creation, and much more. No long-term promises, but still a lot of trust.
Building too robust of an MVP (minimal viable product). We spent way too much time building out a comprehensive product that did everything our customers could have imagined right out of the box, only to find that the deployment took way too long and we couldn’t scale it the way we thought we could. We were truly convinced at the time that we couldn’t make a leaner MVP and this was the fastest/best way to market. Wrong.
It wasn’t until we were backed into a corner and time was against us that we had to go back to the drawing board and come up with a significantly leaner/faster approach. We learned this lesson later than I wish we did, but I’m glad we learned it before it was too late to do anything about it.
I used to think that the more successful I became the fewer problems my business would have. I’ve since realized that it is the opposite. The problems never stop, but as your level of success grows, they change and you are presented with new problems that you will need to guide your business in overcoming.
The way you fix problems is to first understand the problem and what is causing it, find a solution and then implement it. This process involves one thing: persistence. There are easier ways to make a living than owning a business, but I don’t care about easy, I want fulfilling and meaningful.
I’ve definitely faced failure. Any time I’ve written a client proposal that wasn’t accepted, it stung. It’s not just because a contract wasn’t signed, but because I invested time and energy to create something just for that individual or organization. Still, I wouldn’t have become a consultant if I couldn’t handle rejection.
And I fully recognize that just because my proposal didn’t make the cut one time doesn’t mean it won’t next time. I keep in mind that I’m not just trying to find clients; I’m working to build relationships.
My biggest business mistake that is related to my life is that I used to manage a very poor work-life balance. Working online means that it can be quite hard to stop working, as technically you can work forever and there still would be more to do.
Eventually, I realized that I had a problem, and that working 24/7 wasn’t good for me. Now, I try to take off most of the weekend, work ahead of time so that I am not stressed trying to complete work, and so on.
Managing a good work-life balance is so important!
We face challenges every day. To be honest, it’s one of my favorite parts of business. I enjoy logic, problem solving, trial and error, etc. You can’t be right 100% of the time, and if you learn from your mistakes—weaknesses can turn into strengths. I get motivated when I see a challenge.
Some of our biggest clients turned us down for years before we got in the door with them. Each time we were turned down, we came up with a better strategy. Needless to say, our playbook is now stacked with awesome plays for landing new clients and excelling our business.
One of my biggest business mistakes as an entrepreneur is trying to do everything myself. It’s really difficult to scale a business alone, and I’ve failed at that in the past. Having partners makes a huge difference. You can bounce ideas off each other, specialize in different areas of the business, and grow much faster.
Our biggest mistake was launching our product with a price comparison feature: offering buyers the cheapest alternative for their daily shopping. Within 2 weeks, we realized that vendors had a visceral reaction to this “race to the bottom” we created. By week 3, we removed the price comparison feature from our platform.
I have always encountered troubles with both apps. For Safe Ride, I had to deal with speaking to developers in another timezone & apple blocking 3rd party messaging. These weren’t huge troubles but a bit annoying. With Nito, I had to deal with things like school.
It was pretty annoying and hard in school to deal with creating the application while paying attention in class. Luckily, my co-founder Cooper Weiss and I were placed in the same 2nd period free. This allowed us to work on creating more design & making the overall application better.
One of the biggest mistakes (there have been many) was hanging on to toxic clients too long because I thought I needed the money. I have learned that I am happier and more productive when I’m working with people whom I like and who resonate with me.
I’d have to say taking on consulting projects that I didn’t believe in but needed the money. They were massive time sucks that led to nothing but a minor paycheck. Turning those kinds of jobs down was difficult but it allowed me to focus on things that turned out more successful, like my LinkedIn groups.
All entrepreneurs will face many, many failures. We celebrate our failures in our company. Each week in our meetings, we go around the room & state our celebration and our fat failure for the week. We don’t want to overcome failures; we want to embrace them and celebrate them!
Know what else really helps fix business problems? Tools. Know what helps to minimize the likelihood they’ll occur? Tools. What kind of tools you ask?
Accounting, incorporation, compliance, and less expensive online legal services. How about user-friendly business planning software? If you’re facing some obstacles you should checkout our resources review page. Cheers!