Can Your Failure Make You a Better Leader and Investor?

Can your failure make you a better leader and investor? Many people ask that question, and honestly, it depends. For some, a failure will devastate them — for others; the smack-down is what makes the difference in their success. So what is your experience?  — I’d really like to know.

When things are going good, you have the money. When things are going bad, you can lose it all in a heartbeat. –Aaron Amuchastegui

I talked this issue and question over with Aaron Amuchastegui about a year ago, and the logic of the question and the actions the question demands often come to my mind.

Here is a copy of the podcast. I know you’ll enjoy it.

At one point, Aaron had a million dollars saved, yet he still wasn’t investing. He says that he wasn’t spending his money properly, either, and he lost a bunch.

To do things differently

One day Aaron said something interesting to himself. He said that if he ever got another chance with the “big money,” he would do it differently. He “wasn’t going to buy stupid sunglasses and stupid cars.” Instead, Aaron said he would invest in things that mattered, like memories with his family.

Keep your word to yourself

It is amazing, but Aaron Amuchastegui kept his word — to himself. How many times have you been the person who will keep their word to everyone — except yourself? When Aaron was up flipping houses again, he decided to keep 10% of them as rentals. In his words, “if he kept just 10% as a rental, if he lost everything, it just wouldn’t matter.

The mindset change

Deciding to change the mindset came when Aaron decided to invest more for the long term and less for the short term. This would have been a hard switch from being totally on top and at a peak — he was unstoppable — then he lost it all. So Aaron Amuchastegui decided that he was going to “give-back-more.” And he has given back and become a tremendous charitable donator.

“We lost it because we didn’t know any better — but now we do.”

I love this statement about how Aaron didn’t know better. Aaron also didn’t know about finding mentors and guides to teach him the business, and that there are many people out there who know stuff and are willing to help you.


Aaron hadn’t really experienced depression either — and in 2013, when things were bad, he felt it. In the podcast, Aaron Amuchastegui describes what this feels like. He is SO open that I could almost taste what he was saying, and what a blessing for me to hear him share this. If you’ve ever been “stuck” and felt like things couldn’t change, you will want to listen to Aaron describe this experience. You will gain hope and be better for listening to this part of the podcast.

He talks about how he was stuck in the mistakes and thought about them down to the very last detail. Aaron kept saying over and over and lamenting, “I can’t believe I did this or spent money on that…”

Things are things

Aaron learned that all the trips they missed and all of the things they didn’t do were just things — and he has changed how he does those things now. He doesn’t sit back and miss out anymore. He doesn’t make the same mistakes anymore because he is paying attention — all.the.time.

Aaron is quick to say that God blessed him with a second chance to be able to get on top again. He looks at the resale value of items. For instance, when he was down (a situation that lasted nearly two years), he would look around the house for what they could sell.

His 2k sunglasses wouldn’t even sell for $100, and he committed himself, right then, that when he was on top again, he would create and live experiences — not live with meaningless stuff.

Changing other mindsets

You have to learn to relax in different ways about many things — and change your mindset about many things in life. Something Aaron and his wife changed was about their kid’s homework. They were on a trip for two weeks, and this child had been overly stressed about school for a long time. So finally, the Amuchastegui’s said that they would enjoy a two-week vacation without all the homework, and they did.

On the way back, Aaron helped his daughter get caught up in about a two-hour amount of time — plus taught her the extra things (long division) that were on the list. When his daughter got back to school, her class hadn’t even had the time to teach that concept yet.

Aaron decided that sometimes your mindset has to be to relax on some issues while out of town and catch up as soon as you get back. So he went for quality vacations from then on and decided to have other quality experiences, too.

Help others

Keeping his word to help others, at first, when the Amuchastegui’s were traveling, they kept up with social media. Then, they shared their journey with others so that many people could benefit from their experience. Finally, Aaron’s wife documented all the information and wrote a book about the kids’ experiences on their trips and with the school system.

Everyone has their best way for them

Have you ever read something and wished that it was you? I have. But like Aaron pointed out to me, there is the best way for him, and there is the best way for me. We can ask around and find that “best way” — by searching and listening. Each person can find the way that is best for them.

As I’ve thought over my interview with Aaron Amuchastegui, I am amazed at how much I learned and what an intelligent, motivated, and well-centered individual he is.


And as far as the question, can your failure make you a better leader and investor? Failure has made Aaron better at nearly everything in his life. I’d say in the last year, just thinking about the podcast interview with Aaron has made me think differently and search for different answers than I might have otherwise.

So, yes, I believe that failure can make you better at almost everything if you let it.

Image Credit: Mikhail Nilov; Pexels; Thank you!

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