These Two Mistakes Cost Me Millions in Business

But I don’t regret making them. Here’s why.

I’m the biggest failure here.

I’ve failed so many times in business, I have all these cuts and bruises all over my body (metaphorically speaking). I just might be the unofficial ambassador of Murphy’s Law.

Here are two of my biggest mistakes in business, so that you can avoid them. I will also share how you can let your team fail so that you can grow a culture where everyone wins:

1. I drove an old, beat-up truck.

This was what I was driving …

When people saw my truck, they thought they were gonna get a good deal. “Discount” was the first thing on their minds. This made it hard to charge for what I was worth.

To go from a discount brand to a premium brand, I did these two things:

  • I bought a brand-new truck
  • I got a high-quality vehicle wrapper

2. I worked in the business for too long.

From 2007 to 2014, I was the guy running service calls. And I was juggling a ton of other stuff including payroll. (No wonder I didn’t have a life!)

I needed to do all that to get out of debt, but here’s what I’d have been doing to make myself 10x more efficient:

  • Building operating manuals (grateful for my mentor, Al Levi)
  • Hiring the right people and incentivizing them with performance pay
  • Mapping out the vision of the business

Now, I don’t regret making these mistakes and many other ones, because …

I learned how to overcome each and every mistake

I went snowboarding for the first time ever. I fell again and again and my body ached. But during the last run, I didn’t fall at all — I was going down the hill fast. Each time I fell, I learned. And that’s the approach I take in business, too.

If I make a mistake, I reflect and I ask myself: “How can I do better?” I talk to my mentors, I hire consultants, and I read books on the topic so that I don’t make the same mistake again.

But that’s not enough. As business owners and leaders, we also need to help our people fail better:

Why you should let your team fail

When I was a kid, my parents took the training wheels off my bike. They got me to sit on the bike, and they ran with me for about 20 feet … and they let me go.

Did I fall? Yes. I fell a few times, but after that, I learned how to ride on my own.

My point is, if you want your employees to be A players, you’ve gotta let them fall down and fail. You can’t be there protecting them from mistakes every single time.

One of Amazon’s products, the Fire Phone, was a failure. It was a $170 million hit. But guess what Bezos said to the executive who was in charge?

“You can’t, for one minute, feel bad about the Fire Phone. Promise me you won’t lose a minute of sleep.”

Letting your team fail is how you grow a culture where everyone wins. Why? The flip side of failure is success — you will never get to the big wins if you don’t risk losing.

But what if they keep making the same mistakes?

I would not start by blaming my employees. I’d first look at what we could have done to support them. Here’s what I would go through:

  • Did you give them enough training?
  • Were the systems, processes, and checklists clear? Were there any missing steps?
  • Are they in the right role?
  • Did they have the authority to make the right decisions?

And even if it was the employee’s fault, it’s important to start from a place of care. The question I’d ask is: “How can I support you?”

When you care, their fear of failure will go away, and that’s when work will feel like play!