Three $10M Mistakes…And What They Taught Me!

Entrepreneurship isn’t a steady upward climb. It’s riddled with challenges and setbacks. Even 7 and 8 figure CEOs make costly mistakes. So if you’re reading this and you think success is all about luck and assets that are unattainable to you, think again. Everybody fails. But, it’s what you choose to gain from those mistakes that make all the difference. Here are three very real mistakes I made in the past that cost me $10 million. Yes, you read that right!

#1: 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 the people you put in charge. Your leaders set 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. And so will your bottom line. Performance matters, but company culture matters too. Your leaders need to be the people who most deeply possess the company’s core values and beliefs.

#2: I didn’t staff the sales team quickly and sufficiently enough 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. 

#3: I didn’t get involved soon enough in the day to day direction and management of the sales team, to correct what I knew wasn't working.

As CEO, it’s important for me to delegate day to day responsibilities and BE the company’s visionary leader. I have a team of trusted advisors and leaders for this reason. However, what I lack in direct management of day to day tasks, I 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 job to analyze the situation and get involved when necessary. I built this company off of my ownsales 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? I identified, and even had a gut feeling, that these issues were issues. Before they were even actual issues. The problem was, I didn’t act fast enough. Had I trusted myself and took action sooner, things may have worked out differently.

But, with that being said: these experiences taught me -- the hard way -- that I need to act more quickly and forcefully on my inclinations, even when I'm not the direct leader of that department or division.

Understand that as an entrepreneur, you will fail, maybe even epically. But, if you can get back up and LEARN from the experience, you will truly be unstoppable. Not even leaving $10 million on the table.

So trust your gut. And take action when necessary.

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