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18 Most Common Mistakes Entrepreneurs & Startups Make and How to Avoid Them

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14 Minute Read
Posted by Wade Myers on March 14, 2022

A Startup’s success hinges on numerous factors. Since nearly 90% of businesses fail within the first few years, entrepreneurs must familiarize themselves with the most common mistakes to avoid.

According to my significant research on the predictability of success and failure of startups, I would argue that it’s not only a few things, but a whole host of primary business principles that collectively lead to success or failure. And this goes way beyond the amount of capital raised or the quality of the business team. Much of the issue is all this collection of business principles that make up the business model, touching on all aspects of the market context, the financial context, the operational context, the customer relationship context, etc.

To set the stage, let's look at the incidence of failure. According to Harvard Business School research, 70 to 80 percent of all startups fail to deliver a return on investment to investors and a whopping 90 to 95 percent fall short of meeting projections. Many experts agree that between 50% and 90% of all startups shut down completely within the first few years. Harvard Business School’s Shikhar Ghosh explains the problem like this:

How to Avoid Them

"Start-ups often fail because founders and investors neglect to look before they leap, surging forward with plans without taking the time to realize that the base assumption of the business plan is wrong. They believe they can predict the future, rather than try to create a future with their customers. Entrepreneurs tend to be single-minded with their strategies—wanting the venture to be all about the technology or all about the sales, without taking time to form a balanced plan…failure is the norm."

But startups aren’t alone. According to my research, most business opportunities from startups to acquisitions to new product launches have similar failure rates. In addition to an incidence of high failure rates, if a business does successfully get off of the ground, the likelihood of ever reaching meaningful size and revenue are slim indeed.

What are the most common mistakes first time entrepreneurs make?

entrepreneurs make

In a survey conducted by the Association for Corporate Growth and as mentioned frequently in Fortune magazine, only 5% of companies ever reach a paltry $1 million in revenue and only 0.625% make it to $10 million in revenue, that’s only 1 out of every 160 companies that successfully get launched that ever make it to the lower middle market in terms of size. Given all of the above, it’s safe to say that most business opportunities of any nature fail.

Here are some of the most common mistakes entrepreneurs and startups make:

1.  We Make Decisions Emotionally

Single Biggest Mistake = Entrepreneurial Passion > Careful, Rational Analysis

I’ve been there. More than once. On every startup I’ve been involved in.

Nearly all entrepreneurs will make huge mistakes whenever their entrepreneurial passion and zeal outweighs or overshadows or overpowers their ability to slow down and carefully and rationally analyze what is happening. And then reorienting as necessary.

We get blinded by our passion. We overlook obvious issues. We are certain that we will overcome it. “It will be HUGE!” rules our minds.

We will over talk to employees, co-founders, or advisors. We speed up our cadence. We increase our volume. We don’t listen. We don’t want to know. Don’t even try to show us the financials or the burn rate. We will just raise more money. We are about to close a huge deal. Don’t burst our bubble. It might kill our culture. It might kill our special vibe. What if employees lose their mojo? We must keep believing! We must keep trying!

If you are in this place – STOP IT! You are about to fail…

You need to learn what fighter pilots learned when dogfighting. When your heart is pounding like the North Atlantic surf, when your life hangs in the balance on each split second decision, when you’re taking in new information and making decisions at Mach II, you learn to follow what’s known as “Boyd’s OODA Loop”:

Observe, Orient, Decide, Act.

And then repeat.

Over and over again at Mach II.

The trick is to do all four steps. Entrepreneurs in high gear tend to fail in the first two steps of Observe and Orient. We tend to keep drinking our own Kool-Aid instead of being open to changing up our plan or process based on reality and based on changing conditions.

Decisions Emotionally

To diagnose the issues, first, let’s look at how decisions are made by entrepreneurs (and everyone else).

When we pursue an opportunity, whether it is the next big startup idea, a very attractive acquisition or investment candidate, that new franchise that is exploding, or a new product idea that might change the world, we get emotionally attached to our opportunity. As neuroscientist Antonio Damasio has discovered, we make decisions emotionally, not rationally or logically. Damasio explains his findings:

"Often we feel emotions instinctively…gut feeling “marks” the chosen alternative, coloring it with a certain emotional hue so that it is more salient than the other alternatives…As psychologists and behavioral economists have shown, the average person’s day-to-day reasoning is often quite faulty. The human mind is terrible at calculating probabilities and a vivid, dramatic image can dominate someone’s mental landscape. For instance, a person may be quite scared of flying after picturing a plane full of screaming passengers dropping 6,000 feet out of the sky and exploding. Yet the same person may be quite comfortable traveling by car. The irony is that the odds of dying in a plane crash are far lower than the odds of dying on the freeway."

Pursuing an opportunity is rather like that exuberant emotional rush of being in love and overlooking the other person’s flaws that are obvious to everyone else. That leads to a very real problem. Our emotional attachment to our opportunities means we tend to turn a blind eye to the potential issues and not fully explore the downsides.

Every venture capitalist sees this with entrepreneurs during a “pitch” meeting. The entrepreneur is often so wildly enthusiastic about his or her idea that they don’t seem to rationally listen to any potential risks. On the other side of the table, in the “deal” world, those pursuing an acquisition or investment will often go with their “gut” because they really like the entrepreneur, the management team, or the deal itself. There is a saying that acquirers and investors tend to “cave to close” and give up key terms just to get a deal done. It’s the same for any opportunity. We are emotionally wedded to our pursuits and we don’t want logic and reasoning to get in the way.

But even when we do analyze an opportunity, there is another problem.

2.  We Resist Deep Thinking or Analysis

The Nobel Prize–winning economist Daniel Kahneman points out that even if we take the time to analyze something, we tend to stay on the surface in our analysis and come to quick, erroneous conclusions in the problem he identified as the “Law of Small Numbers.” We tend to take a few inputs and then make huge leaps in our judgment and fake ourselves out to think that we’ve properly analyzed the situation. We rarely spend the mental effort to really analyze a situation, much like how we tend to hate to learn math because it is mentally grueling. Kahneman describes the two-system theory of emotional vs. rational decision making as follows:

Resist Deep Thinking or Analysis

"Many of us who study the subject think that there are two thinking systems, which actually have two very different characteristics. You can call them intuition and reasoning, although some of us label them System 1 and System 2. There are some thoughts that come to mind on their own; most thinking is really like that, most of the time. That’s System 1. It’s not like we’re on automatic pilot, but we respond to the world in ways that we’re not conscious of, that we don’t control. The operations of System 1 are fast, effortless, associative, and often emotionally charged; they’re also governed by habit, so they’re difficult either to modify or to control. There is another system, System 2, which is the reasoning system. It’s conscious, it’s deliberate; it’s slower, serial, effortful, and deliberately controlled, but it can follow rules. The difference in effort provides the most useful indicator of whether a given mental process should be assigned to System 1 or System 2."

He goes on to explain the problem with why decision makers rarely delve into System 2 thinking:

"Emotion becomes dominant. And emotion is dominated primarily by the possibility, by what might happen, and not so much by the probability. The more emotional the event is, the less sensible people are. So there is a big gap."

He also pointed out the real problem of optimism that we see so much in entrepreneurs and business opportunity sponsors:

3.  Entrepreneurs Are Too Optimistic

Khaneman's research also showed that one of the major biases in risky decision-making is optimism. Optimism itself is a source of high-risk thinking. But aren’t business decisions usually rational decisions? Let’s look further at how we actually act rather than how we should act.

4.  We Resist Tracking Decisions and Applying Lessons Learned

Resist Tracking Decisions and Applying Lessons Learned

Kahneman further notes that typical business decision-making processes are flawed because of the lack of decision analysis and the lack of capturing lessons learned:

"The thing that astonishes me when I talk to businesspeople in the context of decision analysis is that you have an organization that’s making lots of decisions and they’re not keeping track. They’re not trying to learn from their own mistakes; they’re not investing the smallest amount in trying to actually figure out what they’ve done wrong. And that’s not an accident: They don’t want to know…they won’t want to do it."

Now that we know we need additional rigor and accountability in our analysis of opportunities, where do we turn to find that?

5.  We Lack a Rigorous Opportunity Analysis or Due Diligence Framework

The more I studied this issue of high failure rates, the more I realized that there wasn’t a good framework or construct for analyzing an opportunity. Most decisions and business due diligence were simply ad hoc. I saw this in the Fortune 500 world, the venture capital investment industry, the investment banking industry, the M&A process, and with startup entrepreneurs. There was a lack of process discipline around what to analyze and how to objectively measure the opportunity to assess its probability of success or failure. There didn't seem to be a good process for filtering out all of that dangerous optimism.

Over the years I’ve read thousands of business cases in business school, thousands of news stories about business, and thousands of business plans. And I’ve advised hundreds of businesses, from rank startups to Fortune 500 clients. I’ve also invested in startups, launched many businesses, and acquired quite a few others. So I went on a journey of discovery and analyzed everything – what went wrong and what worked well in all of those different situations.

What I discovered was that in most cases, the outcome of a particular opportunity was completely predictable. No matter how much entrepreneurial energy, no matter how much wild optimism, and no matter how many hours of effort poured into an opportunity by a high-quality management team, if the business model was fatally flawed, the opportunity failed.

As it turns out, there are many core principles at play that can be identified and measured to predict success or failure and used to vastly improve an opportunity once the weaknesses are known. In response to this issue, I created Opportunity IQ with 50+ proven principles ranging from the market dynamics to the financial characteristics to the operational characteristics to the offering itself to the customer relationship – all of which can be used as a tool to measure and assess any business opportunity.

6.  Example Principle That Affects Success or Failure

For example, let’s look at just one of the principles and its impact on potential success: the Cash Cycle. I define the Cash Cycle as the average amount of elapsed time between when an opportunity experiences the costs of the offering being delivered and when the cash is collected from the customer. The more efficient the Cash Cycle, the faster you get paid, and the better the opportunity. The more efficient the Cash Cycle, the more cash flow is generated, and the less the need for external financing for working capital and growth.

Affects Success or Failure

Many business models have problematic Cash Cycles, especially any opportunity that requires an offering to be produced ahead of demand. Let’s look at two easy to understand examples: spec homebuilders and automakers. Both types of businesses invest heavily in labor and materials for up to several months in advance of selling a home or a car. Both types of businesses consume enormous amounts of cash to fund growth, usually in the form of debt. And during economic downturns, they often go bankrupt when sales slow down, their Cash Cycle lengthens, and they can no longer service the debt on their balance sheets.

By contrast, e-commerce business models like Amazon are usually amazingly capital efficient because they get paid up-front by charging the customer’s credit card first and only later experience the costs associated with processing and fulfilling that order, which in Amazon’s case, is outsourced to the publisher or manufacturer. (Because of Amazon’s scale, it has the negotiating leverage to extract extended payment terms.) This type of Cash Cycle means Amazon continues to grow their cash as their business grows rather than consume cash. The faster they grow, the more cash they produce.

Objectively and rationally measuring the Cash Cycle of an opportunity is one example that should be on everyone’s due diligence list prior to launching or investing in an opportunity, yet most entrepreneurs are completely unaware of the principle and very few ever measure its impact.

7.  Aim, Aim, Aim…Instead of Fire, Adjust, Fire, Adjust…

Less planning and more selling. Stay in front of customers. Consult with your customers prior to building out your offering. Never do it in this order: 1) plan, 2) launch, and then 3) try to find customers, instead, do it in this order: 1) find customers that are willing to pay you to solve their problem while you “perfect” your offering, 2) do that over and over again (and you will be launched), and then 3) measure the results and fill in your plan and make adjustments as necessary.

Aim

8.  Investing in Infrastructure that Already Exists/Trying to Create Too Many Capabilities

Never invest in any infrastructure that already exists. Outsource everything except for the most strategic nature of your offering. There’s already tons of capacity for everything – just tap into it. Creating capabilities from scratch in a startup is really hard. Focus on the most important capability in your value chain and partner for everything else.

9.  Not Owning the Sales Pipeline

Don’t hire a sales team and expect them to just deliver sales while you focus elsewhere. As the entrepreneur, you need to live, eat, and breathe sales. You need to be the primary rainmaker. You need to inspire your sales team. It also helps you stay grounded in terms of what’s working and what’s not working. And that way, your sales leader can never BS you.

Don’t underestimate how hard it is to land customers. It is really hard to grow. Really focus on how you identify prospects, how you qualify prospects, how you quote prospects, the sales process, the stages, the failure points, why you lost deals, and the sales cycle time.

10.  Hiring Too Fast and Firing Too Slow

Instead, hire slow and fire fast. Never confuse a few early wins with a trend. It’s a fluke. Never hire in the euphoria of winning a few deals. Contract for someone’s work first, kick the tires, test them out. Once you sign them up, it’s really, really hard to unwind.

Firing Too Slow

On the other hand, if someone is not working out, let them know immediately. If that continues after additional feedback, let them go immediately. Once you see the issues with an employee, everyone else already knows they need to go and are wondering why it is taking you so long to fire them. And always pay a severance, but get them to sign a release in exchange for their severance.

11.  Launching with a 50/50 Partner or Three Equal Partners

It almost never works. Someone needs to be in control and have the ultimate decision-making authority.

12.  Hiring Friends and Associates Instead of Experts That Know Exactly What to Do

There is no time for on-the-job training in a startup. Only hire staff that have done exactly what you want them to do, with the tools you want them to use, in the context in which you are operating, at the stage in which you are operating, at the pace in which you run, and with values that match yours. Anything else is going to fail or cause misery or be misaligned.

13.  Not Owning the Financial Model

You don’t have to be a finance or accounting expert, but you better know your financial model. You need to know your customer acquisition cost, your CLTV, your unit economics of each major offering, your cash economics, your overall business model. You need to own it, you need to be able to explain it, and you need to make sure your CFO or Controller is on top of it.

Financial Model

14.  Trying to Finance a Bad Business Model Instead of Fixing It

Having a cash crunch in the early stages? Add two more zeros to your revenue and you will still have a cash crunch unless you fix your business model. Focus on the ability to fund your own growth rather than trying to raise capital to fund your growth. Raising capital is hard. Prioritize your ability to gain liquidity and improve your cash cycle. Get customers to pre-pay. Negotiate extended terms with vendors. If you get paid upfront with a low customer acquisition cost, you can grow indefinitely without external capital.

15.  Focusing Too Much on Selling Stock Instead of Selling Customers

Every startup thinks raising capital is the answer to all of their problems. It’s not. It solves one problem, but creates new ones (managing a board, answering lots and lots of questions all the time, a deep long-term financial stewardship relationship, a prioritization of the financial outcome over everything else, including your personal life, family, health, etc.) Selling customers creates more value and makes you more attractive to investors. Focus more on selling customers.

16.  Not Realizing that Raising Venture Capital Means You Just Gave Up Control

Chances are really good that by raising capital: 1) you no longer control the series (A, B, etc.), 2) you no longer control the board, 3) you no longer control the majority of shares, 4) your stock was turned into 5-year vesting options, 6) you can get shot and replaced at any time, etc.

17.  Worrying Too Much About the Competition

They have their own issues. Ignore them. Focus on selling and delivering a great offering and you will do just fine.

Competition

18.  Not Focusing Enough on Repeatability and Scalability

Having a repeatable offering (the exact same offering for all customers) and a scalable offering (very little COGS or Direct Labor for each incremental unit of offering) are the two most powerful components of a highly successful and profitable business. Do not deliver customized anything – it doesn't scale.

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