Three Mistakes That Cost Me Ten Million Dollars

Three Mistakes That Cost Me Ten Million Dollars…and what they taught me!

Entrepreneurship isn’t a steady upward climb, in fact it’s riddled with challenges and setbacks. Even 7-8 figure CEOs make costly mistakes, so if you’re reading this and thinking success is all about luck and assets that are unattainable to you, think again. Everybody fails. It’s what you choose to gain from those mistakes that makes all the difference. So without further ado, here are the three very real mistakes I made that cost me a whopping 10 MILLION DOLLARS. You read that right, 10 MILLION DOLLARS. YIKES.

Mistake Number One

I put a high performer in a leadership position who could do the job, but wasn’t a team player. 

Leadership can make or break a company. As CEO, it’s important to assign leadership roles to people who embody your company values. This is something that should be considered when making all hiring decisions, but ESPECIALLY when it comes to those you put in charge. Your leader sets the tone and expectations for the rest of the team, and if they’re unable to motivate and inspire your employees to work together and push themselves, eventually your whole company will suffer, as will your bottom line. We unfortunately needed to fire this person, which was a huge waste of time, energy and resources. Performance matters, but culture matters too. Your leaders need to be the people who most deeply possess the company’s DNA, and model the type of culture you want to duplicate. 

Mistake Number Two

I didn’t move quickly enough to staff the sales team sufficiently to get the results we wanted.  

When you aren’t hitting your numbers, it’s easy to look at your team and wonder what they’re doing wrong. Before firing anyone or wasting time on more training, consider the possibility that you might just be short staffed. There isn’t a trick or tactic in the world that can fix your sales if the math doesn’t add up. You have a finite number of employees who can complete a finite number of tasks, so if they’re motivated, talented, working to your standards and still not seeing results, they likely aren’t the problem. I knew our conversion rates in and out and could have easily hit the numbers if we were staffed properly. I didn’t do it, and it cost me big time. 

Mistake Number Three

I didn’t get involved soon enough in the day to day direction and management of the sales team to correct what I knew was not working.

As CEO, it’s important for me to delegate day to day responsibility in order to fulfil my role as the company’s visionary leader. I assemble a team of trusted advisors and leaders for this reason. However, what I lack in direct management of day to day tasks, I still need to make up for in awareness and attention to detail. At the end of the day, the buck stops with me. If something isn’t working and isn’t getting better, it’s my duty to analyze the situation and get involved if necessary. I built this company off of my own personal sales skills, and I have the insight and experience to quickly identify and solve problems. In this case, I hesitated, and in doing so wasted time and money. 

The important takeaway here is that I identified and even had a gut instinct that these were issues before they were even issues and didn’t act on them fast enough. Had I trusted myself and acted sooner, things may have worked out differently.

These experiences taught me the hard way that I need to be more forceful in acting quickly on my inclinations even when I am not the direct leader of that department or division.

I hope in writing this that you know as an entrepreneur, you will fail, maybe even epically, but if you get back up and LEARN from your mistakes, nothing will be able to stop you, not even leaving 10 million dollars on the table. 

Above all, learn to TRUST YOUR GUT and take action when necessary.
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