I Went Bankrupt For $1.5 Million and This is What I Learned About Failure

By A.J. MacQuarrie 

Bankruptcy is considered the ultimate failure in business. When it’s referenced in our culture — in movies, television shows, or the news — there’s a stigma that gets attached. Those going through this perceived nightmare are shown in the worst possible light: villainized as corrupt, irresponsible, or fraudulent. In 2019 alone, 752,160 Americans filed for bankruptcy, according to U.S. Court statistics. I was one of those people.

I was an extremely proud entrepreneur who turned a $20,000 angel investment that I got from a customer at a Starbucks that I used to manage into a multi-million dollar business, from scratch — only to then be sitting in bankruptcy court with $1.5 million in debt. I failed big-time. The amount of shame, embarrassment, and guilt that came from that experience created such a large wound in confidence that I’m still healing from it, over two years later. 

It was one of the most difficult moments in my life. And yet I still remain an entrepreneur who believes that the exhilaration of starting a business far outweighs the potential risks, heartaches, and headaches. I learned so much from my last business failure that I almost feel that experience earned me an MBA. When you go through the roller coaster ride of a startup, you are equipped with knowledge and wisdom like no one else in the business world. 

So, for that reason, we should fail more. Let’s say the average entrepreneur has three failures before their final success. Well, each failure led them closer to their success. And maybe it took those first two failures to provide the know-how to make the third a triumph. Thomas Edison famously said, “I have not failed. I’ve just found 10,000 ways that won’t work.”

What are the benefits of failing?

  1. It builds a callus. It makes you stronger and stronger after each setback and failure. The more you go through, the more immune you will become. Setbacks, failures, and disappointments basically set the threshold for how much you can handle and how well you can handle it. You’ll start to develop a “bring it on” attitude and will be able to deal with whatever comes your way. You’ll be able to rise to the occasion better than ever. You will be able to handle each failure better and better and won’t get thrown off. Therefore, you will be one step closer to your success. You’ll be able to maneuver through setbacks with every one that comes your way.
  2. It provides valuable lessons. You’ll be sure to know what not to do next time. A wise man (Samuel Smiles) once said, “We learn wisdom from failure much more than from success.” We often discover what will do, by finding out what will not do; and probably they who never made a mistake never made a discovery”. We know touching a hot stove will result in a burnt hand, hence why we’ll never touch that stove. Somewhere back in time, someone tried to light a fire until the first person, forever lost to history, finally succeeded. And today we have gas stoves right in our kitchens.
  3. It gives you a chance to reset and recharge. When you fail, especially when you fail big time, you will take a step back and recalibrate. This will give you a chance to not be in the thick of things. The breathing room that failure provides will give you the chance to hit the reset button. A failure will have you travel a new path you might have never explored.
  4. It forces you to look at the bigger picture. That recalibration and rest will force you to revisit the bigger picture of what you originally set out to do. When you encounter a setback, you are often brought  back to a whole new, fresh drawing board. When I went bankrupt, well, I had a clean slate to work with again through a new lens of openness to possibilities. You’ll see opportunities where you may have overlooked them before and will be forced to evaluate the vision and plan accordingly.
  5. You gain experiences that you didn’t expect. It keeps you on your toes and brings a whole new level of awareness that you didn’t have before. This gives you an amazing advantage by keeping you flexible and open to change and. The experience of failure will change you in a positive way that at first you won’t even be able to articulate in words, just feelings. Failure in business leaves room for spontaneity, vision, and surprises- when you’re open to them.
  6. It adds to your personal story. The reality is that failure makes you a more interesting and humble person. Failure can add a dynamic layer to you that builds character. When I was the CEO of KarmaBox, I was starting to become an arrogant asshole and I think I needed to be brought down a few notches. A $1.5 million bankruptcy will do just that.
  7. It can bring you closer to the ones you love. After I went bankrupt, I was concerned that people who I once was close to would try to distance themselves for me. It wasn’t the case at all. Everyone in my life who I loved and cared about were nothing but supportive and loving. It may have even brought us closer together in a weird way. People actually love to support the underdog because they can relate more to them rather than the winners.

It’s clear to see that failures themselves are not going to take you down, it’s how you respond to them that will ultimately determine your success. Failures come in all different sizes, but even the biggest ones can be leveraged properly to be turned into advantages. 


The next time you encounter a failure or setback, try as hard as you can (I know it can be difficult) to have an attitude of gratitude rather than a sense of disappointment. For each hardship you endure, may very well put you on a new path that you would never have chosen otherwise. Everyone fails, it just takes one success to make it.


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