The Top 11 Reasons People Fail When Transitioning into Entrepreneurial Ventures (Like outside sales)

This article will apply to anyone who tries to transition from the ranks of employed (being told what to do and when to do it), to the wild, wild, west where you hang your own shingle and have no boss…but also no safety net. This is where you operate solely on commission, or you have to create your own paycheck. We also refer to this as signing the checks on the back instead of signing them on the front.

I’ve been at the game for 37 years and watched hundreds…who’s kidding who…THOUSANDS of people fail in commission-based or entrepreneurial ventures, and, oddly, it’s usually for the same small group of reasons. It’s not that sales leaders, coaches or mentors, like me, don’t tell them what’s what or offer them the best training, we do, but human nature is a bitch.

Some people just ultimately do and think whatever the hell they want to do and think, regardless of the counsel available. LOL!

So, a lot of this failure to launch stuff comes as a result of a lack of openness, cognizance or willingness on the part of the person transitioning into a role where they have to govern themselves. So, since I miss David Letterman so much (the new guy isn’t as funny as Dave) let’s do the old top 10 list countdown thing and I’ll try to rank these in order of what I think the significance is. (But I will give you 11 reasons do David Letterman doesn’t sue me)


They Have No Exit (or advancement) Strategy

Outside salespeople and entrepreneurs often fail because they don’t think carefully enough about their possible exit (or advancement) strategies during the early stages of their business. If you are a sales rep, the range of advancement opportunities will become clear to you once you completely understand the industry and company you’re associated with. If you are a true startup, (not attached to an organization) things will become clear once your services hit the market. Your core customer, and the competition will tell you exactly what your options may be. Is your exit an IPO or an acquisition? Is it an acquire-hire or a recapitalization? Smart people have a sense of how the advancement or exit will occur within 12 – 18 months of their launch. Dumb people aren’t even thinking about this.


They Make Themselves INVISIBLE

If they can’t find you, they can’t buy your stuff. I swear that some people jump into sales, or start a business venture and then enter a self-imposed witness protection program. If you plan to be successful as you make this type of transition you have to tell the world about it. From my experience, some people either forget that they have to expose their products and services to anyone that’s willing to listen (direct or indirect lead) or they are too damn cheap to budget and spend a little money for marketing and advertising. Look, you can have or develop a best product in your class, but unless you become a crazy, committed evangelist for it, you will die a slow death. Smart, successful entrepreneurs get the word out early and often via all available media, especially digital media. Dumb ones don’t.


They’re Fixated on the Wrong Thing

This is one of the most noticeable explanations for why many entrepreneurs fail. If your foremost reason for jumping into outside sales or a new business is to make a ton of money rather that to create value and add value to those you serve and touch, then you’ve started off on the wrong foot. This may sound rather mystical to you, however, I have found that God and the universe will never bless and reward your business if you seek to GET something for yourself before you GIVE something of value to those in the marketplace. If this is where you are at the starting point of your new enterprise, you need to do some heavy soul searching and check your value system. I have never had an ounce of success financially when making money came before providing real value to the people I sought to serve.  


They Are Extravagant

If you are wasteful or flamboyant, spending money irrationally, you are on the path towards failure as an entrepreneur. Great entrepreneurs learn how to act frugally. They do more with less. This is about managing valuable resources and most people jumping into outside sales, or an entrepreneurial venture, have a limited amount of both money and time. A sure way to set yourself up for a crash and burn failure is to start showing off the success of your business by doing lavish things, or purchasing material things that are symbols of wealth. Operate with a strict budget and stick to it. Spend money on the things that make you money.


They Are Risk Averse

Fear of failure is another big reason why entrepreneurs fail to launch. Failures allow that fear to overtake them, even before they get started. Being entrepreneurial is about channeling your passions and creativity into something you really care about doing or achieving. People who succeed don’t fear being laughed at or care that somebody called them, “crazy.” Making positive change in the world and in their own life is a big driver and motivator for winners and it far outweighs any fears attached to the small risks associated with the venture.


They Have Unreasonable Expectations

While it’s good to believe that you can accomplish ANYTHING, even pull off an occasional miracle, that’s not a way of thinking to base your business plan on. Some entrepreneurs simply fail because they’re self-delusional believing that they’re brilliant enough to revolutionize a business or industry and become filthy rich in a year or so. When the world (or market), doesn’t welcome their authority and recognize their brilliance, it’s the world’s fault, not theirs. And then they quit.


They’re Short-sighted

This is about a lack of vision. You must be able to see what you and your business will look like far into the future. Anything less than this sets you on a path towards failure. If we agree that the essence of being an entrepreneur is to always be of great value to those you serve, then you must always be asking, “What work can I do today that will meet the needs of tomorrow?” Not having this mindset places you or your enterprise in a precarious position. If you are not getting better, then people with true vision, who are improving their business model each day, will eat your lunch.


They Don’t Change or Pivot Quickly Enough

Self-employed people sometimes fail because they cannot adapt to change or the unpredictable events that happen around them. (And things are always unpredictable when you’re an entrepreneur) All new ventures require a person to be flexible and require them to pivot away from their original plan occasionally. A person who makes the fateful decision to stay the course when everyone else around them knows that they’re about to crash and burn, are stubborn, and also a little bit stupid. I also call this phenomenon, “Falling in love with your own ideas.” This is not a good trait.


They Don’t Create the Right Team Around Them

Entrepreneurs sometimes fail because they don’t identify the right people to advise them. This includes locating a good small business accountant and properly assessing the skills and experience of legal counsel. They also fail because they don’t engage and build relationships with the people (hierarchy and/or peers) that would and could really help them see things clearly or differently. It’s about looking around and making sure you are surrounded with the right players. There’s a lot to know, and many entrepreneurs just don’t know enough as they’re getting started. You desperately need to make key these connections and to keep those players around you, close to you.


They Don’t Focus on Core Strengths

You and I, we talk about focus a lot. If you read, watch or listen to any of my content at you know that this word is prevalent. I see it all the time. A person new to the game of being an entrepreneur will try to do many, many things, some things that aren’t even close to their core strengths. What will eventually happen is that this person will not go deep enough, dedicate enough time to master the skills that will help them survive. They won’t achieve excellence in any skill or task. They simply bounce around, staying very busy, but creating no profitability.

Your success or failure will come as a result of how well you focus on and maximize your core strengths. I also refer to something called “genius work.” Your genius work is those activities you’re naturally good at and also enjoy doing. These are the things you would probably do for free. This is a key to how every great entrepreneur in history became successful. They fought the urge to be a jack-of-all-trades and they became a master at only a few. High-level entrepreneurship is about using your passion to make a positive contribution for the benefit of others. I want you to stay focused on what you do exceptionally well. 


They Operate in a Bubble (and don’t Invest in themselves)

 If you exist alone, in your own little world, operating in a bubble, there are very definite limits to what you can do and achieve. The new salesperson or entrepreneur who’s on the crash and burn path is the one who will never seek the help of others. Great things are seldom achieved, and great careers are rarely built, all alone. If you are an entrepreneur, it’s important to understand that you are only a vessel through which an idea, innovation or product/service is being launched. It is wise to get rid of any scarcity mentality you might have that someone else is going to steal your ideas or beat you to it. This way of thinking usually results in a person refusing to solicit the help of those better than you in certain areas. If you are a new salesperson it is critical that you invest time and money into the best investment you have…yourself.

I didn’t go to college. It wasn’t in the cards for me. However, I knew how important being educated was, and even if it wasn’t formal schooling, I was going to learn. Henry Ford famously said, “Many a man who’s putting a few dollars a week into the bank would do much better to put it into himself.” Just like investing in a business, investing in yourself can pay heavy dividends down the road. If you end your education after college you are doing yourself a disservice. The type of work we will do in the future isn’t necessarily being taught in school because that exact kind of work hasn’t been invented yet. The world of business changes fast. You will need to keep up. It’s imperative that you continue to invest in yourself as if you were a business, whether it’s with a high-level personal coach, seminars or online training. Most experts suggest you budget at least 3 – 5% for specific business coaching, mentorship and education. If you religiously do this you may find yourself having greater success not only in business but also in other key areas of your life. 

Go here for ACCESS to all of the good (FREE) stuff on our site:

Read the first two chapters of The CAP Equation (book) for FREE:

The CAP Equation© website offers free resources for commission salespeople and sales leaders such as:

Please click on the link below for FREE INSTANT ACCESS to all of this:


Joe Buzzello is a nationally recognized expert on the roles of direct selling, entrepreneurialism and leadership. He has built legacy sales teams and experienced unprecedented success in individual and business-to-business markets as well as the network marketing industry. Joe has held executive level positions for Fortune 500 companies, but he has never strayed far from the art and science of selling, which he loves. In early 2014, Joe began writing, speaking, and coaching through his platform, and The CAP Equation©.


If you liked this blog post, please share.

2 comments on “The Top 11 Reasons People Fail When Transitioning into Entrepreneurial Ventures (Like outside sales)”

  1. T Money


    I am fileing this under baiwiw (Blog Articles I Wish I Wrote.)

    The one thing I would add to your list is the inability for most people to balance long-term vision with short-term urgency. If your vision is not big enough the obstacles will appear huge. But if you don’t engage in serious prospecting/sales activity TODAY your vision will never come true. Rare is the man (or woman) who can truly ballance the two. What say you?


      A sense of urgency…yeah. All people who successfully transition get after it hard, like there is no tomorrow. Good one, Timmy. But then I’d have to have 12 reasons and I was using my 11 Creative logo as the image for this blog, which means I’d have to find an image of a 12, which would be extra work and this blog is free and stuff…

Comments are closed.