How to Succeed at Failing in Business: Lesson #001

Sell, sell, sell…

Matthew Caiazza
4 min readDec 2, 2019
Photo by Element5 Digital on Unsplash

Today is Lesson #1 on How to Succeed at Failing in Business. As The Failure Guru, I am dedicating these lessons to help you fail. Everyone assumes that people who start businesses want to succeed but some don’t…they actually set out to fail, or appear to want to fail in the eyes of everyone who tries to help.

The one thing I regret about my business failures is that I did not have someone like me to teach me how to fail. In the coming months I will provide you with critical lessons that I wish I would have had: how to succeed at failing. What follows is the first lesson, I hope it helps.

Let’s face it, nothing happens until something is sold. Therefore it is really important to make sure that you never stop trying to drive the top line. One of my first mentors once said to me: “Get the order first, then worry about how you are going to make it”. At another time, I asked him when his business really started to take off. His answer was “When the bank called me to tell me they were foreclosing”. Obviously, he knew what he was talking about when he gave me that piece of advice. He never stopped selling no matter how little gross profit he made, no matter how short his production runs became, and no matter how tight his cash flow became. The point was that the top line was growing so eventually the bottom line would take care of itself. As an entrepreneur you know that you are only one big customer away from breaking thru, and until that time comes, at least make sure that margins contribute to overhead. Driving the top line no matter what the margin or product/service will actually lead to an increase in your overhead due to all of the extra work it causes, but remember, you set out to fail and it is a lot harder to fail with low overhead.

Selling to drive the top line will also help reduce your concentration risk (having too many eggs in one basket) because it will ensure that you have a revolving door of customers, and lots of them. Many of them will be on the smaller side and have a high cost of service but it is really important to fail big so you need to be big. With all of these new customers you will require a large customer service department and they will get great training making lame excuses to small, pain in the ass customers so that when they have to deal with a big one, they will sound confident.

Production will love it too because they will get to push the boundaries of what can be done since you will be taking in business that is increasingly outside your company’s core competencies and there is nothing that production loves more than sticking a square peg in a round hole. In fact, your whole company does because being able to come thru for you is important to them, even if you are the one who made the hole round in the first place.

Employees will love the overtime that comes with doing things outside of the company’s core competencies and since they need the money more than you do it only makes sense to take every sale you can.

Selling to drive your top line so you can contribute to overhead until you become profitable or land that elephant customer is also really good for the economy. How, you ask? Since you are smart enough to take any sale, not only will your employees have more disposable income, you will need to hire even more employees to work second and third shifts to make or provide all of those overhead contributing, outside of your core competency products or services. After all, you want to be accomplished and no one will notice a small failure so the bigger your operation, the better.

The only parties that will be concerned with your strategy are other stakeholders such as investors or lenders. These types of people tend to think they are smarter than you just because they have many more years of experience than you do. You recognize that it is a problem for you if they actually are smarter than you. However, since you are fantastic at selling, you will be able to handle them on your way to being very profitable. Profitability is what all of your stakeholders want, and they need to know you can deliver. It is critical for them to think you can deliver if you want to fail.

Takeaway: Keep selling with reckless abandon, because, since nothing happens until something is sold…you won’t succeed at failing without the sales...lot’s of them.

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Matthew Caiazza

I am an entrepreneur and CEO who is passionate about helping businesses and helping others.