SSS #12: My Biggest Business Failure


Once in a while I read, hear, or see something that unlocks my brain. It's like I've been plugged into the matrix for a particular problem I've been dealing with. I may not have even realized I had that problem to begin with. I don't quite know how to explain it. But stick with me...

A random example would be... you're listening to a podcast about "X" and the host says something in passing about "Y" and that one sentence is the final piece to a puzzle you've been trying to solve. This random after-thought for someone else is the exact message you needed to receive to make significant progress in your life.

I hope I didn't lose you. And I hope I'm not the only one this happens to...Cause it's awesome when it happens. I call these moments brain-gasms.

Anyway, these types of revelations have happened a handful of times for me. For each instance, I can remember the feeling of my subconscious thoughts being put into words in a way I couldn't explain myself. In today's post, I want to share with you one such instance.

It's a story about the time a short book called Ego is the Enemy helped me realize I could shut down my biggest business venture without letting that massive failure define me as a person.



Driven to Massive Failure by an Unchecked Ego

In October 2017 Dia and I closed the doors to our frozen yogurt and smoothie restaurant. I still remember the last time I twisted the key twice to the right, listened for the deadbolt to click, pulled on the handle to make sure it locked, and looked inside to check if I left any lights on.

That routine was the last step of a closing checklist I performed a thousand times before. Except on this final run-through, I looked through the window into an empty restaurant. No more seating for families to enjoy their Fro-Yo. No more blenders to make strawberry-banana smoothies. No more machines to make sweet green juices. No more cash registers to ring in sales.

I was looking into an abyss. A blackhole that sucked in whatever we were willing to give it: Three years of 12-hour days, hundreds of thousands of dollars, and so much more.

The Struggle

It was the most difficult decision of my life. For about two and a half years, giving up never crossed my mind. I was determined for this business to be my Tour-De-Force. It was going to make for the ultimate comeback story.

I went as far as envisioning the story we’d tell our future children. I’d include all the struggles we faced and how we ultimately prevailed. How we sacrificed everything to make it work. How we’ll hand down this business to them, if they decide that’s what they want.

That was the story I grew up on. My parents are the immigrant couple that came to America in their late twenties with one kid and less than $100 in their pocket. They started as housekeepers in an Atlantic City motel. They worked their way up to managing a property in Pine Brook, NJ. They ultimately risked everything to buy the business they worked so hard to improve. Most of what I am stems from this origin story for our family.

But that story didn’t play out for us the way we wanted it to. And that’s ok. I finally came to terms with the idea of shutting the business down after my thoughts were so clearly put into words by one of my favorite authors, Ryan Holiday.

Protecting My Ego

Ego is the Enemy was Ryan’s second book in his Stoic philosophy based Trilogy. A little blue book happened to be the ultimate guide for me to get past the one thing most often standing in the way: myself.

As I read, and re-read that book (3x in one year), I realized the BIGGEST reason I hadn’t quit that business earlier: I was afraid of how failure would make me look.

I was afraid of my uncles and aunts taking pity on my parents. I was afraid of being a failure in front of my massively successful friends. Many of whom were in the midst of obtaining graduate degrees while working full time at big name firms. I was afraid to admit defeat in front of my wife and her family.

All of these thoughts were driven by my ego.

The fact is people make mistakes all the time. Ego is the Enemy helped me realize the real problem occurs when you begin to tie your identity to the mistake. The negative feelings compound when you can't help but worry people think you’re less valuable because of that failure.

My ego was asking “Why is this happening to me? How do I save this situation and prove to everyone I’m as great as they think?” How silly. Only ego thinks failure and embarrassment are more than they actually are.

The Effort is Enough

Reading Ego is the Enemy instilled the mindset that we can control our efforts, but we can’t control the outcome. For the longest time, I was banging my head against the wall thinking, “if I try harder, I’ll get the result I want.”

The reality is there will be times when we do everything right, yet the result can somehow still be negative. If we let ego determine our emotions, we’re doomed. Ego requires compensation, recognition, and full appreciation for even the smallest effort.

Like Cutting off a Leg

I had failed in business before, but this time was different. This was the first time I raised outside capital to open a business. This was the first time I quit a 6-figure salaried job with damn good benefits to dive head first into an industry (restaurants) that’s infamous for being an entrepreneur slaughter-house. This was the first time I went against the advice of people who have my best interests in mind when they told me to stick to my day-job and keep hustling on the side.

I didn’t listen. Instead, I risked it all. I was 25 years old, about to enter my prime earning years working in the exact field I got my degree in. I was recently married and somewhat ready to start a family. I quit my job, and dumped my entire life savings ($100K+) into one venture. I didn’t stop there, I also raised money from friends and family to back me on this venture.

I was testing the depth of the river with both feet. You can begin to understand the amount of pressure I put on myself to perform.

We tried everything to make it work:

  • We negotiated a new rent payment schedule with our landlord. We agreed to significantly reduce rent in the 4 winter months and moderately increase rent across the other 8 months.
  • We went outside the Franchise Agreement by acquiring most of our goods from places like Restaurant Depot & Costco instead of the preferred food distributors we were required to use.
  • We went outside the Franchise Agreement by hiring outside of the required vendor list for services like credit card processing, marketing material, and equipment maintenance.
  • We worked ourselves and our high school student employees to the bone because we couldn’t afford to have more people on shift during the busier summer months.
  • We catered multiple events per year only to break even on costs in hopes to garner more brand awareness in the local area.
  • We tried delivery. I was delivering juices and acai bowls in the convertible my sister let me borrow for free because she had a company car.
  • We introduced new product lines that weren’t approved by our franchisor.
  • We did a bunch more [suspect] cost-cutting stuff I’d rather not publish online.

Sales were stagnant. We lost money on a monthly basis. After 12 months, Dia went out and got “a real job”. She was in an office from 9-5 and in the restaurant with me from 5-9. Thanks to her, we were able to subsidize losses ourselves instead of continuously raising more money from friends and family.

After another 6 months, we wanted to move out. I started working full time at my parent’s business so I could start contributing to help make ends meet. My parents were kind enough to pay me slightly more than I paid my employees so I can keep the difference.

It was like going to work to pay for daycare just to get away from the baby for 8 hours a day.

I found myself in a hole, but I couldn’t stop digging.

Early Pride

The Fro-Yo fad was over. I was late to the party. The location was bad. There wasn’t enough parking and only one side of the highway could enter conveniently. The competition was heavy. An ice cream shop less than 1/4 mile away had been thriving for 3 generations of ownership.

The writing was on the wall early on. Everyone saw it except for me. I was too busy making excuses and being blinded by my ego. I can actually remember telling myself, “I’m going to figure this out. I’ll show them.” As other franchisees across the country were shutting their doors in droves, I told myself, “That’s not going to happen to me.”

I reached out to at least a dozen people with extensive retail / restaurant / hospitality experience. I showed them my financial books. I asked them to tour my market with me. I ran all my plans by them: marketing, new products, etc. At least I had no problem asking for help. But I was desperate. I was willing to do anything, but the feedback was almost always, “recover what you can, shut the doors, move on to the next thing.”

I wasn’t there yet. I was driven by an unwavering ambition. I had already talked myself into making this business work. I counted my chickens before they hatched.

After reading the Aspire section of Ego is the Enemy I finally understood how much entitlement I operated on and how little self-awareness I had. I had no business opening a restaurant. I grew up in Real Estate and studied Finance. I worked in lodging, audit, business development, and client financial management.

But that’s the problem with even the smallest amount of accomplishment. Up until that point in life, most things came easy for me. School was a breeze, especially college. I’ve always been able to make deep & meaningful connections that continue to stand the test of time. I played the career advancement game well while experimenting with multiple side-hustle businesses. Finding and ultimately marrying my soul-mate practically fell into my lap on a chance encounter in another country. There were a few speed bumps along the way. But nothing major. I thought I was the shit. Then came my...

Fight Club Moment

You know the end scene of Fight Club when the buildings start blowing up and Ed Norton is just standing there watching in utter disbelief. That’s what this failure felt like. The world crashing down around me.

Although, if the restaurant literally blew up it would have been better because the insurance pay-out would have covered more of my losses.

I overestimated myself. I lost perspective. Today, I constantly remind myself of my limits. I have spent hours at a time sitting and thinking about what I can and can not do. For the things I can not yet do, I identify the cost to acquire that skill and ask myself if I’m ready to pay the price to learn it. I wouldn’t have this approach if it weren’t for this failure.

I often wonder what would have happened if that business turned out to be a success. I probably would have failed at the next thing. Which would have likely been an even bigger investment of time, money, and other resources.

Although the outcome is regrettable, I feel lucky to have experienced my fight club moment at such a young age with such good people around me.

Reverend William A. Sutton says, “We cannot be humble without experiencing humiliation”.

Ernest Hemingway says, “The world breaks everyone and afterwards, many are strong at the broken places. Those who do not break are killed”.

This event absolutely demolished me. Everything I thought I knew about the world was rendered false. I had to reconcile something I knew with something I was too afraid to admit. But from the ruin, came a great opportunity for progress and improvement.

Ego makes it so difficult to face the symptoms and cure the disease. It’s so much easier to delay or double down before deliberately making any change.

Through reading Ego is the Enemy I finally came to terms with what everyone was trying to tell me but my ego wouldn’t allow me to hear. I was in a chronically leaking boat. Energy devoted to changing vessels is more productive than energy devoted to patching leaks.

How About You?

I’m begging you to start asking yourself:

  • What are you (not) doing out of fear of judgment from others?
  • Where are you giving yourself credit when it belongs to someone else?
  • Where are you bending so much you’re on the brink of breaking?

Take some time to think about it. Before it’s too late, and the false reality you’ve built comes crashing down around you.


If you want to read my notes on Ego is the Enemy, click here. Disclaimer: My “notes” on this one are more like an abridged version of the book.

If you never read Ryan Holiday’s work, I highly recommend his trilogy on Stoic Philosophy.