Why Entrepreneurs Fail: 18 Business Winners Explain Their Biggest Fails

“Failure should be our teacher, not our undertaker. Failure is delay, not defeat. It is a temporary detour, not a dead end. Failure is something we can avoid only by saying nothing, doing nothing, and being nothing.” – Denis Waitley

Failure is a fundamental part of entrepreneurship.

Only half of new businesses survive the first five years. Move forward another five years, and two out of every three businesses have failed.

why-entrepreneurs-failIf you’re persistent, failure becomes just another lesson on the road to success. But in order to learn that lesson, you have to understand why you failed.

Or even better, you can learn why those who went before you failed and avoid their mistakes while minimizing your own.

So why do entrepreneurs fail?

That’s the question we sought to answer by seeking out 18 of the most successful entrepreneurs we know and asking them the following 3 questions:

  1. What was the biggest failure of your career?
  2. Why did you fail?
  3. What did you learn from it?

We got some pretty incredibly responses, and we’re excited to share them with you today.

Let’s get started!


Fail #1: Focusing On Things That Don’t Matter

One of the biggest mistakes new entrepreneurs make is getting distracted by things that don’t really matter, while ignoring the core pieces of building a business.

Business is ultimately just about sourcing something of value and then selling it to customers.

You can grow your Twitter account, take world-class headshots, and print a batch of stylish business cards, but at the end of the day, if you aren’t acquiring customers, you aren’t building a business.

Ross Simmonds, co-founder of Crate and Hustle & Grind, describes how he wasted his early days focusing on stuff that didn’t matter.

ross-simmondsRoss Simmonds, Hustle & Grind

While my entrepreneurial journey has been full of ups and downs, I’d say one of my biggest failures came right after I graduated from University. Fresh out of school with a marketing degree and excited about the industry after watching a few episodes of Mad Men, I decided I would start my own agency.

The company was named Altego (no one could pronounce it) and we started off on the wrong foot. You see, similar to many new entrepreneurs, we made the mistake of focusing on things that really don’t matter in the long term. For example, we spent months designing a logo, business cards, registering the business, negotiating shares, coming up with the name and designing the website. We were investing MONTHS and THOUSANDS of dollars into doing these things without any revenue. Unfortunately, it was our downfall. We spent too much time doing things that didn’t matter and had no choice but to find full-time jobs after maxing out credit cards on these busy tasks.

The lesson is simple. Focus on things that move the needle for your business from the start. It’s easy to get excited in the early days about getting a new website, designing a logo, picking a name and getting your business registered. But at the end of the day, you’re better off spending that time talking to real leads, closing real clients and hustling up the work that puts money in the bank.

Thankfully, I learned that lesson young, and the next time around, I was able to do things the right way. Over the last few years, my consulting business has thrived to a point where I’ve been able to launch multiple companies, make a couple investments and travel the world.


Fail #2: Partnering With People Who Have Similar Skillsets

Virtually every successful business person has a story to tell about how teamwork and networking propelled them forward in their careers. In fact, a survey by Salesforce found that 86% of respondents cited lack of team collaboration as a primary cause of company failures.

But as anyone who ever completed a group project in school can tell you, teamwork is only effective with the right teammates.

When you partner with the right people, you can leverage each other’s skillsets to grow more quickly and create something more valuable than you could ever accomplish alone. When you partner with the wrong people, things are guaranteed to go downhill fast.

When most people think of “bad partners”, they think of lazy, unmotivated, dishonest, or unfocused individuals, and while those qualities certainly make for a doomed partnership, sometimes the real cause of failure is much more subtle.

As Benji Hyam, co-founder of Grow & Convert and Wordable, explains, sometimes partnerships fail simply because the partners are too much alike.

benji-hyamBenji Hyam, Grow & Convert

In my first business, I partnered with someone that was really talented at what they did but that had a very similar skill set as me. When it came time to focus on scaling the business, we had a hard time scaling because we couldn’t divide and conquer large tasks. We had the same weaknesses and there was no one to fill those, so we got bogged down doing tasks that we weren’t the best at instead of focusing on our strengths. Ultimately, I decided that long-term, the partnership wasn’t a good fit because of so much overlap in our skills so I decided to exit the business.

From that experience I learned that for a partnership to work, it’s important that Co-Founders have different strengths and weaknesses so that they compliment each other. You’re able to get more done and think through harder problems when you have partners that have different skill sets. For example, a non-technical and technical founder, a creative and analytical founder, etc. In my current business, I found someone who compliments my skills very well. I’m good at the marketing side (content strategy, promotion, partnerships, etc.) and my partner is good on the analytical side (conversion and measuring success). We’ve been able to challenge each other and focus on our strengths which allows us to do our best work.


Fail #3: Neglecting Your Customer Base To Chase A New Segment

Today’s global marketplace moves fast. To lead the way, you have to act quickly, adapt constantly, and persistently maintain customer growth.

Competition and innovation are rarely problems for entrepreneurs, but in the rush to the top, it can be easy to forget the fundamentals

One of the most devastating mistakes any business can make is neglecting its core customer base. Mitch Miller, author of Consulting Exposed, describes how he lost a large chunk of his core clientele while pursuing new customer segment.

mitch-millerMitch Miller, Opposed Media

My biggest failure was a few years ago when we decided to aggressively expand into a part of the industry we had no clue about but thought we did.

We decided to create an arm of the business that sells coaching to financial advisers. We hire two in-house phone sales guys, fly in a sales trainer to train them, buy lists of phone numbers, and let them get to work. It was harder than we had imagined, and the cost was significant before we axed it. But… there was one hidden cost that is the real reason this is my biggest failure to date.

We neglected our main business to chase the shiny object, and that gutted us in a big way. Business turned away, we lost $70k/month in revenue, clients backed out, and stuff got messy. Fast forward 3 months, we were literally sleeping under the desk in our office, because we had no house. The office rent was one month overdue and we had already sold everything there was to sell.

Luckily we would rather die than give up, so we worked 20 hour days until we got back on our feet. The lesson here is, if you are going to expand, do it, but never do it at the expense of what you already have unless you are ready to not have it anymore.


Fail #4: Neglecting The Human Part of Business

There are a lot of intangible reasons to invest in your employees and facilitate a positive work environment. But even if we ignore the intangible and stick to the bottom line, companies with engaged employees see 233% greater customer loyalty and a 26% greater annual increase in revenue.

Simply put, your people are important.

Eric Siu, CEO of Single Grain and Growth Everywhere, found this out the hard way after taking over the business.


Eric Siu, Single Grain

The biggest failure for me was almost losing my entire company because I wasn’t empathetic enough. I had many of our team members quit and it took me awhile to realize that people quitting meant that they were basically firing me as the leader of the company. All because I didn’t built enough rapport with the team.

That’s because I originally came in to help save the company and I made sweeping changes without establishing relationships with teammates. Always, always, always communicate with your team so they’re in the know. It’s your job as a leader. Over-communicating is better than not communicating.

Your company will only go as far as your team takes you. If they aren’t fond of you, you won’t be able to build something for the long term. I’m grateful for learning that lesson early in my entrepreneurial journey.


Fail #5: Failing To Anticipate Future Costs

Different business models have different needs. While certain models allow for slow, steady, organic growth, others require that you hit a certain critical threshold within a short timeframe.

Understanding your business model and your critical milestones are crucial to success. Failure to understand where you are, where you’re going, and what you need to get there can stagnate or even cripple your growth.

Wade Floyd, founder of CoachTube and NeedTo, explains how failing to anticipate the cost of scaling caused him to reject financing offers that could have catapulted the business.

wade-floydWade Floyd, CoachTube

When I launched NeedTo.com, it was essentially a first-to-market platform. We had major traction early and reached profitability much more quickly than I’d expected. Our brand was new and sexy and we were getting a ton of regional and even national press coverage.

During this hot streak, we had a bunch of heavy hitters interested in investing in the platform, and I made the mistake of rejecting some financing opportunities I should have taken. It was my first time hitting this level of success, and I failed to anticipate just how much capital we needed to scale outside our region and how quickly the market would turn into a competitive land grab.

While the business remains profitable to this day, my ultimate goal, which I’ve carried into Coachtube, has always been to create something truly revolutionary, and I learned that to accomplish this, you have to be willing to embrace outside help and understand that big-time visions often require big-time financing.


Fail #6: Skipping Due Diligence When Hiring Key Players

Hiring will make or break your business. It’s not a matter of if but when.

You can get away with hiring a bad freelancer from time to time, but when it comes to key employees or major project outsourcing, getting the right people makes all the difference

While most entrepreneurs understand in this, in a fast-paced market, it can be tempting to cut corners, skip due diligence, and rush to execute on new ideas. This is especially true for newer entrepreneurs, who tend to severely underestimate the time and monetary cost of turning their ideas into reality.

Wyatt Jozwowski, founder of DripApps and co-founder of Demio, explains how

wyatt-jozwowskiWyatt Jozwowski, DripApps

Like most entrepreneurs, I have a countless number of failures under my belt; my failures go all the way from shutting down projects, running out of money, bad partnerships, and other similar things of that nature. My most recent and notable failure is one of patience. Typically, I’m incredibly ambitious, and I never hesitate to take action; I want things to get done as quickly as possible. These traits came back to bite me in starting my latest software company, Demio.

Before Demio, I had only been involved in smaller, less complicated software projects. You could even say, I got lucky with finding the right people. So when starting Demio, I didn’t waste any time finding a group of people that claimed that they could build this far-fetched software in a record amount of time. I should have seen the red flags, but my ambition blinded me. I had hired an agency that I knew little about. Months later and 6-figures gone, I had nothing to show. My partner and I even learned that this Agency had outsourced the work to $10 per hour Indian developers. Yup, my outsourced project was outsourced. We scrapped everything, and we started from scratch. While it didn’t completely kill the company before it even started, it did make a huge dent on the financial side, cost us a ton of time, and crushed our early spirits.

Since this failure, we’ve gone on to hire a team of absolute A-players. They’ve single handedly made Demio a reality. I’ve learned how vitally important it is to find the right people from the very beginning. “Get the right people on the bus,” as Ben Horowitz would say. It takes patience, and it takes discipline to purposely slow things down in the beginning while looking for those people, but it will speed things up 10x when it matters; it will be the difference between success and failure.


Fail #7: Neglecting Core Relationships During A Busy Season

There’s more to life than money, and while succeeding as an entrepreneur often requires sacrifices, the core relationships in your life shouldn’t be counted among those sacrifices.

Nurturing your relationships through busy seasons is a book unto itself, but ultimately, it’s all about keeping open lines of communication, taking personal responsibility for yourself, and maintaining awareness of the needs of those around you.

Geoffrey Woods, founder of The Mentee Podcast, explains how his marriage struggled during one particularly busy season and the revelation that bought things back from the brink.

geoffrey-woodsGeoffrey Woods, The Mentee Podcast

The biggest failure of my career was in my marriage. I had sought my wife’s approval before starting a new company. I communicated that launching this new company would be a fulltime job, but I would still need to perform at my corporate job. Working two fulltime jobs, our marriage was going to have to take a backseat. My being “present” was going to have to take a backseat.

She gave me the green light at first, but then, fast forward six months of me not being present, and the marriage really started to get strained. My mistake here was thinking that since I had been upfront with her at the beginning, I was off the hook. I wasn’t accepting accountability or realizing that I still had a part to play, so when things got tough, I went to blame, shame, and justification. “Why isn’t she being more understanding? Why is she being so aggressive?”

I placed the blame on her, and it wasn’t until I met with a mentor to seek guidance on why she wasn’t understanding my needs that I realized I wasn’t understanding her needs. He whipped out a metaphorical 2-by-4, slapped me across the face, and said, ‘Bro, this is on you. You need to take responsibility for your part and do a better job of identifying specific ways that she needs to feel loved through this process.’

I think this is a mistake that a lot of entrepreneurs make. It’s easy to feel like the victim: to look at the people in our lives and think, ‘Why don’t they understand what I’m going through?’ and make it about us instead of taking responsibility for our own part.

I was not showing up in the way I needed to as a husband to then deserve that support back from my wife, but once I embraced that and became proactive about identifying what she needed from me, it was much easier for her to give me what I needed during that season.


Fail #8: Dividing Focus Between Too Many Projects

It’s very easy for modern entrepreneurs to succeed. There are a million ways to win, and you can find exact, proven strategies all over the web, many of them completely free.

Sometimes, however, this access to limitless information can paralyze us or cause us to divide our focus, jumping from one project to the next rather than focusing on one thing at a time.

This can be equally tempting for both new and veteran entrepreneurs, but as Scott Oldford, founder of Infinitus, describes, it is especially dangerous for experienced entrepreneurs who are leveraging more financing and have higher stakes at play.

scott-oldfordScott Oldford, Infinitus

As an Entrepreneur the biggest challenge was two fold, in the end it brought me to $726,000 in debt. The first was a lack of focus, many of us believe that we can split our focus and leverage our time in a way that allows us to do multiple things at once – typically, this isn’t true unless we have far more financial backing.

Fooling myself like this, made me invest my resources (time and money), incorrectly, leading to a level of leverage that was far too high and in exchange, I failed.

There is a phrase that says, “Your talent may bring you places your character can’t keep you”, this is ultimately, very true. It’s very important that you work on your character, every day, that you improve 1% every day and that you are both humble and grateful for where you are and where you’re going.

I didn’t have the right character and combined with being over leveraged, it led to a very difficult time – a character building time in my life.


Fail #9: Holding Back Instead Of Going All In

There’s a time to test the waters and time to dive in head first.

Many entrepreneur begin their journey while they are still fulltime employees. For these individuals, it’s good to identify a product/market fit, do some due diligence, and land a client or two to before ramping things up. But at some point after you’ve validated your idea, it’s time to lose the safety net and pull the trigger.

Allen Brouwer, blogger and co-founder of Best Self Co, describes how he wasn’t able to achieve any meaningful results until he dove head first into his new business.

allen-brouwerAllen Brouwer, AllenBrouwer.com

My biggest failure as an entrepreneur was not being all in. I remember when I first started my company I was half in, half out. I was timid to jump in with both feet. It was scary and I was afraid to remove the safety net (my 9-5). Then, the safety net disappeared. Turns out, a 9-5 wasn’t as safe as I thought it was.

I only had one choice so I took the leap. Having my back against the wall I was forced to go all in, forced to make it work, forced to believe in myself. This was the game changer.

Since this day forward I’ve had amazing results and accomplishments. I’ve had dreams come true and experienced life in a whole new way. Have there been hard parts? Absolutely. But only because I became 100% committed, I’ve been able to bust through those challenges without turning back. What’s the teaching here? Believe in yourself, believe you can do it, and then go for it with everything you got!


Fail #10: Spending Money Carelessly Instead of Investing Back Into The Business

Let’s face it, we all love spending money. That’s a big part of what being a successful entrepreneur is all about: living the type of lifestyle we couldn’t before.

That said, entrepreneurship is usually a marathon rather than a sprint. One of the smartest things you can do with early wins in your business is invest that money back into the business.

The market is always shifting and evolving. Staying ahead of that shift requires investment, and as Ben Fisher, co-founder of Gurus NYC, explains, spending too carelessly in the early days can leave you out in the cold in short order.

ben-fisherBen Fisher, Gurus NYC

At 19, I struck gold and made over a quarter million dollars with Adsense in just a few months time. I had been making money online for years but never anything quite like this. Rather quickly, my teenage self started buying designer clothes, expensive cars and hotel suites.

As I watched my account balance dwindle, I continued to blow through my money without thinking twice.

By the time I turned 21, over 90% of my money was gone and so was my income source. This was my wake up call. It was time to grow up. Instead of thinking about my next purchase, I started to think about my next business venture.

I worked extremely hard over the next few years and lived quite frugally. I bought only the essentials and invested everything I made. For the past 2 years, I’ve been running a marketing agency for nonprofits called Gurus NYC. Everything that happened has led me here, so I can’t say I have any regrets. Sure, I could have been a millionaire much sooner, but dwelling on this idea serves no purpose. Live and learn!


Fail #11: Following The Advice Of People Who Haven’t “Done It”

Sage advice and experienced mentoring can make all the difference for your business, but as soon as you experience some success, everyone and their mother will have something to say about how you should do things.

It’s important to differentiate between those who have actually accomplished something you want to emulate versus those who haven’t. This can be especially tricky when director investors are involved, as Daniel McGaw, founder of Effn Amazing, explains.

daniel-mcgawDaniel McGaw, Effin Amazing

Being an entrepreneur is hard. This is why it can be so important to have an outside opinion to help you grow the business. In many cases, when I was having a hard time, I would turn to my advisors, investors and so on. In many cases, this has worked for me, but in one case, it ended up ruining the entire business

I used to run a company called Fuelzee which is a simple gas app which will help you find local gas prices. Was a fun company to start, but working in the convenience store space was tough and we ran into dozens of huge hurdles. In one of these situations I turned to an investor and asked their advice on how we should roll it out. I figured hey, this is my investor and he has been there and done that, so his advice would be good.

His advice though was one of the reasons the product ultimately failed. When launching a localized product you have the hard decision to go nationwide or just focus on a region. In my opinion you need to focus regionally till you get good traction, but this was not the advice i got back. I was told go national or no one will care you exist.

So, I did was I was told, even though I felt they were wrong. This simple decision made it so we never got any traction in the app. We just could not build any density in a region because there was too many regions. All in all, we could not retain our users and the product has yet to get any real success.

My failure though is listening to someone who does not know enough about the situation to be qualfied. This is a mistake I have made multiple time and many other make as well. Just because someone is an investor, richer than you or even smarter than you, does not mean they have the right answers to your problem.

You need to find people who have been there and done that, not people who think they know or people who have written a book about it without actually doing it. These people need to be a grain of salt in your decision, but should not drive the direction of your business.


Fail #12: Ignoring The Advice Of People Who HAVE Done It

While you should always be careful about who you allow to influence your business, it’s easy to waste time trying to reinvent the wheel.

Sometimes the best thing you can do is follow the exact steps of those who have gone before you and accomplished what you are wanting to accomplish. As Pablo Picasso once said, “Learn the rules like a pro so you can break them like an artist.”

Jamil Velji, founder of Easy Automated Sales, explains how he wasted time and money trying to prove his advisers wrong instead of learning from their experience.

jamil-veljiJamil Velji, Easy Automated Sales

When I started out down the road of becoming a marketing consultant, I had a lot of advice thrown at me by people much, much smarter than myself. One big piece of advice I got was to aim narrow, position myself as an expert of one service to one market and it would be a piece of cake to scale.

Being the head-strong type, like most entrepreneurs, I set out to prove that theory wrong. Hundreds of hours, thousands of dollars in advertising and marketing dollars and a handful of burned clients later I had to shut down my consulting shop and start fresh.

I had two big lessons taken away from that experience. One, there is always someone out there who’s done what you want to do, learn from them, don’t throw away their advice.

Two, paying to have mentors, coaches and shortcuts is essential to move forwards quickly. I could have saved nearly 6 months of my life, a lot of headaches and a lot of stress if I had just listened to what a bunch of really, really smart people told me.


Fail #13: Getting Complacent And Taking Shortcuts

As popularized by Tim Ferriss’ bestseller, The 4-Hour Workweek, the web provides modern entrepreneurs with relatively easy access to business automation. If you know what you’re doing, it’s not difficult to build a profitable business quickly and then put it on autopilot.

When things are difficult, it pushes us to work hard and do things the right way. But when things get easy, we are often tempted to become complacent and start taking shortcuts.

Sam Oh, ecommerce expert and founder of Money Journal, describes how taking shortcuts destroyed his first successful business overnight.

sam-ohSam Oh, Money Journal

Comfort is a key ingredient in the recipe for failure. Over the span of 2 years, I was able to grow a new eCommerce site into a $50K per month business, starting with a hundred bucks. I put in 18 hour days, 365 days a year to get to that point, and I felt like I deserved a break.

For the next year, I golfed twice a day, and travelled wherever and whenever I wanted. It was the first time in my life that I had money to spend and no one to stop me.

But it all went south overnight. One day, I woke up and was expecting to see roughly $1,000 in sales. There was less than $100.

Translation: My $50K/month autopilot business turned into $5K (if I was lucky).

During my comfortable days, I had tried black hat SEO techniques that shattered my life of “financial freedom.” Worst of all, I wasn’t building an email list outside of customers.

I diverted my attention from traffic to leads and quickly rebuilt the company and was eventually acquired by some tech guys. Since then, I’ve generated over a million leads and sales. The best part? No one can take that away from me (except the unsubscribe button).


Fail #14: Wasting Time On Small Thinking

While most of the failures we deal with today involve some form of backward motion, sometimes failure is more about a lack of forward motion.

For example, what is worse? Losing $1 million overnight or spending 2 years underperforming by $200k per month?

This is the first thing that came to mind for Johnathan Dane, founder and CEO of KlientBoost, when we asked him about his biggest failure.

johnathan-daneJohnathan Dane, KlientBoost

As weird as it sounds, one of my biggest failures as an entrepreneur has been thinking too small. While in college, I was thrilled out of my mind doing PPC management and making around $10k/mo. I felt like I had it made.

After college, I spent 18 months working with the cofounder of a PPC agency and quickly realized I had set the bar WAY too low. Now three years later, my own agency is on the verge of hitting $250k/mo in revenue. We have goals of reaching $500k/mo in revenue within another year, and even then, I still think I’m selling myself short.


Fail #15: Losing A Big Piece Of Recurring Publicity

There’s nothing worse than when you’ve fought hard to take a big step forward in your career and then you get knocked right back.

Responding to and learning from setbacks is what entrepreneurship is all about. There’s no avoiding this. You can either hop right back up or you can waste time bemoaning your circumstances.

Aaron Orendorff, founder of IconiContent, explains how he handled one such setback in his career: losing a major piece of recurring publicity he had worked hard to attain.

aaron-orendorffAaron Orendorff, IconiContent

Failure isn’t easy. And past success is no guarantee against it. In fact, past success isn’t even a guarantee of thick skin.

My latest failure hurt something awful. From August to November, I had my own column at Inc.com. My articles were shared over 15k times and I had a couple of big wins, including an infographic with Backlinko’s Brian Dean and interview with the co-founder of $2 billion company. And then came the email from my editor’s editor: “Can we set up a time tomorrow to talk about your Inc.com column?” Nothing good ever follows a message like that: not in our personal lives … not in our professional.

Sure enough, we met the next morning and they told me straight: “We’re canceling your column.” Why? Turns out, I’d written too many “person focused” articles instead of “topical” pieces. I was crushed, especially my ego. Getting the column had been a big forward step in my career.

So what do you do after bad news like that. You get the f*** back up. Immediately, I turned around and took the articles I’d been working on for Inc. and (after just slight editing) got three of them placed on Success.com and another on Entrepreneur. Hustle, people … hustle.

The deeper lesson is this: you can’t afford to identify yourself with your work. When you do that — when I do that — success means I’m on top of the world … and failure is unbelievably crushing. You are not your work. Freedom from failure only comes when you connect yourself to something deeper: purpose, service, and (for me) spirituality. Plus, I’ve got a little motto I tell myself over and over again: #LetsGetRejected. When I make rejection the goal, it’s far easier to take chances, fight the fear, and balance my wins with my losses


Fail #16: Failing To Delegate

Many entrepreneurs begin as solopreneurs, but at some point, if you want to grow and scale, you have to begin building a team.

Waiting too long to hire and delegate can significantly hamper your growth, as Jodi Gonsman, founder of By Jodi, explains.

jod-gonsmanJodi Gonsman, By Jodi

One of the most valuable lessons I have learned as a business owner is the importance of delegation. You can’t run a successful company and wear all the hats. I would say my biggest failure was trying to do it all for far too long. Trusting other people with your brainchild is challenging, but it is absolutely essential for growth. It is also incredibly rewarding when you find amazing employees who are as passionate about your business and product as you are.

It’s important to have employees build trust and demonstrate competence before you give them additional responsibility. If you don’t, you can get burned very easily. Giving them basic, simple tasks and seeing how they respond will give you insight into their ability to think and grow with your business over the long term.

That said, it’s an amazing moment when you see an employee take ownership of tasks that are out of their immediate project scope in order to benefit the company. Many entrepreneurs take these people for granted, which is short-sighted. When you have an employee who is going above and beyond, you should begin looking to provide incentives for their performance and make sure they share in the reward for growing your business.

Good communication is key in this approach to team building. Make sure your expectations and milestones are clear and then reward employees who meet those expectations. Different employees respond to different incentives, and never underestimate the power of verbal affirmation. It’s also important to differentiate between honest mistakes and mistakes that suggest a poor employee attitude. When you respond to honest mistakes positively and treat them as a learning experience, you foster loyalty.

Letting go of the reigns enables you to focus on your strengths where they are needed most and opens the door to growth for your business, and your team, that could never be accomplished alone.


Fail #17: Trying To Be A Jack Of All Trades

When you are just starting out, it can be tempting to look for opportunities anywhere you can find them, and in some cases, saying “Yes” to everything can be beneficial.

But only for a season. Once you begin gaining momentum, it’s important to focus and develop actual expertise in one area versus trying to be a jack of all trades.

Jacob McMillen, copywriter and founder of The Digital Careerist, explains how he wasted years spreading himself too thin.

jacob-mcmillenJacob McMillen, The Digital Careerist

When I  started in digital marketing, I spent the first few years learning a pretty wide array of skills. I had a solid grasp of SEO. I could write decent copy. I was competent at email marketing. I could build great looking websites. Etc etc.

As my career progressed, I ended up getting clients in all of these areas and I thought that staying a jack of all trades would prevent me from missing out on any clients who came my way.

A few years in, however, I started to realize that most of this activity was a waste of time. By becoming an expert in just one area, I could deliver a higher quality service and make more from a single client than I was making by doing mediocre work for 10 clients before.

I followed through on this revelation and honed in on my craft as a copywriter and content strategist, and within a year, I was getting big time wins for my clients and landing the type of recurring contracts I could only dream about in the early years.


Fail #18: Focusing On Minutia

There are a million things that can keep us busy as entrepreneurs, but only a handful of those activities will be the driving factors behind our success.

Identifying the “One Thing” we need to pursue and focusing on it will accelerate our success.

Brad Campbell, essentialist and founder of Brad’s Ads, calls this approach “less but better” and describes how learning to focus revolutionized his business.

Brad Campbell, Brad’s Ads

I took a trip down memory lane trying to single-out my biggest business fail.  It took a while.  There were plenty! And, after some serious thought–and enough coffee to kill a donkey–here’s what I decided:

Rather than a website that nobody saw or a product that no one bought, my biggest fail was not training my mind early-on. I thought it was all about tools and tactics.  Software and systems.  Gurus and gadgets. As a result, I majored in minutia.  I busted my butt and got nowhere.

So what changed?

I picked up a book.  And the book sucked.  And didn’t help me at all.  However, sooner or later, I picked up another one that did: The Millionaire Fastlane by MJ DeMarco. I cannot give that book enough credit for setting me straight.  If it was a human?  I’d hug it.  Lollipop?  I’d lick it.  Puppy?  I’d pet it.  (You get the point.) It’s must-read for anyone who wants to build a multi-million dollar business.

Anyways, after MJ’s concepts peed all over my previous projects, I began building smarter businesses. And whaddya know, results soon followed.  There were still hiccups, sure, but I was at least headed in the right direction.

Then another book found its way into my library: The ONE Thing by Gary Keller.  Which put what I was doing on steroids.  (You even lift, bro?) And, finally, Essentialism by Greg McKeown–holy moly–that book is just stupid-good.  Like, it’s maddening how powerful those pages are.

Those three books, specifically, steered me away from failure; toward success.

So let’s bring it full circle: my biggest business failure was neglecting my noggin.  I had to “get learned” before I could get paid.  I think every entrepreneur has to have a few critical ah-ha! moments–from books or coaches or trial and error or all the above–before their work becomes meaningful; then profitable.


Conclusion: What’s Been Your Biggest Fail?

Thanks for reading this discussion of why entrepreneurs fail.

We plan to update this post in the future, and we’d love to include you. Just jump down to the comments below and tell us about your biggest failure as an entrepreneur.




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  • Rusty Pang

    Dave, I enjoyed reading this article. Currently, I’m in the middle of a situation myself. I had a partner who was too similiar to me (both ENTJs), but we have different mindsets. He’s still a good friend of mine, but we had to part ways and that hurt. It hurt my pride because I thought I could mentor him along the way and it hurt my heart in that I felt alone again.

    You see, I realized something recently and it was that I’ve been trying to bring my old friends into the business world so I could have business friends. What I should have been doing is finding friends through the business owners I meet in the world. This has a been a fundamental shift in my mentality and it is like closing the final page to good book. I have the simultaneous feelings of satisfaction, sadness, and hope.

    I am satisfied because I’ve lead a good life so far. I am sad because that season has ended. I am hopeful because a new story is being written. Although I do not know where it will lead, I know it will involve me becoming a better man of character and helping a hell of a lot more people.

    Thanks for a great article Dave and Happy New Year!

    • Dave Rogenmoser

      Thanks Rusty!

      I like your thought there on not trying to bring all the old people into this new world you have. Not going to work.

      I think it’s hard as entrepreneurs finding good friends who understand us and get where we are coming from. That’s one of the problems I’m trying to solve in the Entrepreneur Alliance.

      We’ve got your back, Rusty. Glad to have you along for the journey.

  • Awesome tips. And I love how you got to interview all those people who have been through it all