MyPillow CEO, who once caused a $6 million problem, explains how to learn from money mistakes

MyPillow founder and CEO Mike Lindell.
Courtesy Jeniece Pettitt | CNBC

Learning from failure is a skill that Mike Lindell, the founder and CEO of MyPillow, has had to master over time.

In 1979, after just one semester of college, Lindell dropped out of the University of Minnesota with hopes of becoming an entrepreneur. His first venture was a carpet cleaning business. He also tried to become a professional card counter in Las Vegas and to raise pigs for money. Although those businesses didn't succeed, Lindell persevered.

In 2004, Lindell decided to turn his idea for a pillow that would never lose its shape into a company. Since then, MyPillow has grown into a business raking in around $300 million a year.

There were challenges and missteps along the way, though. In 2012, Lindell says, a mistake cost him big: "I was $6 million in the hole because I didn't look at my costs and I wasn't tracking my stuff."

Still, Lindell believes his detours were crucial parts of his journey to success: "I wouldn't be where I'm at today if everything would've been smooth back then. I wouldn't have learned what I did and know what I know now."

Here are two ways Lindell suggests you too can learn and make the most from your mistakes.

1. Track wins and losses to learn from both

When Lindell started MyPillow, he had no experience in the bedding industry. "I didn't know anything about the products. I did a lot of due diligence to figure out where to get supplies and to find different vendors."

When the company started rapidly expanding, Lindell no longer made due diligence a priority. That's how he ended up needing to solve that $6 million problem.

To learn from his mistake, Lindell started tracking what was working and what wasn't. Now, he says, "I track everything as a CEO. I get daily reports of every little commercial to every customer review, and that's what I base my decisions on. I'll see something good, and I've trained my employees to recognize a deviation."

I wouldn't be where I'm at today if everything would've been smooth back then. I wouldn't have learned what I did and know what I know now.
Mike Lindell
the founder and CEO of MyPillow

Lindell believes reflection is a crucial part of tracking your success. "If you see something that just spiked up and did really well, you have to find out what and duplicate it," he says. And when you experience setbacks, understanding why is just as important. "If all of the sudden there's something bad that happens, figure out what went wrong, because the same input is going to keep giving you the same output."

You can apply the strategy to your ordinary life and see results, too. Kristy Epperson, 23, was able to pay off $20,000 in debt in one year by following a similar approach. After tracking her expenses, Epperson realized her key problem area was credit card use. "I would look at my credit card bill and not even remember some of the charges," she told Grow in 2019. So she ditched her credit cards and wiped out her debt by going cash-only.

Wharton professor Adam Grant even suggests you compose a "failure resume," because it's important to be open about the challenges you face and to show yourself that you can cope with setbacks. "I don't think there's any skill more critical for success than resilience," Grant told CNBC in 2017.

2. To solve big problems, start small

Today, MyPillow sells a range of products in addition to their flagship pillow, from beds and linens to pet beds. But if it wasn't for a technique known as reverse engineering, Lindell says his company wouldn't even exist today.

When sales started to pick up steam, MyPillow had a problem: It had future orders in its pipeline, but the company didn't have an established history of sales that would qualify it for bulk discounts on materials. In search of a solution, Lindell broke the pillow down into parts. He spent hours testing configurations until he was able to keep costs down without sacrificing quality. "I reverse engineered the pillow, or problem, to come up with a solution," he says.

When tackling a big problem, start small, Lindell suggests.

Amber Jamieson, the author of the financial newsletter "Better Have My Money," says the same is true when it comes to investing. Saving for financial goals like retirement can seem daunting, but you don't have to start with huge sums of money to set yourself up for long-term success, she told Grow earlier this year. Likewise, if you have loans, you can build momentum by tackling, and eliminating, the smallest debts first.

If you're not too afraid of failure to start, you're more likely to achieve your goals.

Take chances, Lindell says: "You have to make calculated decisions based on logical odds. ... Learn all you can about everything: business ... investments. But don't sit there and be too frugal or too careful. You have to take chances to learn."

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