Entrepreneurs Struggle

What Do Entrepreneurs Struggle With Most?

Entrepreneurs struggle is real but it shouldn’t define you.

A little more than a year ago, I realized I needed more from my life. I quit a promising, lucrative job to build an app that would make it easier to give to charity.

I convinced one of my best friends from college and my brother to work full-time on my vision. We even managed to get a summer intern.

I didn’t know it then, but I was about to enter one of the most difficult periods of my entire life.

Two days after, our App was rejected from the Apple App Store.

“No big deal,” I would tell my team, “apps get rejected all the time.” We submitted an appeal and continued our daily grind.

Entrepreneurs Struggle
Photo Credit: Apple

We were dead-broke, so we wrote our patent ourselves. We were cold-calling nonprofits and pitching the few that would pick up. We were spending hours making content that, though we didn’t know it at the time, few people would ever notice.

Anything to keep my team, to keep myself, from asking the question we feared most:

“Is this all going to be for nothing?

READ ALSO – Entrepreneurship Life Is Not For Everyone, Do You Agree & Why?

A month passed with no word from Apple. Two months. Four months. I called their support line every single day. I sent emails. I tried to find connections on the inside. Every day, knowing that my team looks to me for morale. Crickets. Nothing. Not an email. Every once in a while, I would sombrely glance at the sealed bottle of bourbon on my shelf. We agreed not to open it until we were live.

But we had one more shot in the chamber, and I rallied the team.

We abused the whiteboard, brainstorming every single possible reason we might have been rejected. We wrote a 25-page appeal. We poured every ounce of our collective commitment, brainpower, and fear into the project that could have been our last.

As I upload the document, my co-founder turns to me and says, “Pete, if you get us through this one, I’m with you to the end.”

A week later, we were accepted without changing a single line of code. The moment I found out, I was the happiest person in the world.

That night, we popped the bourbon that symbolized our dreams. We might just pull this off.

Then we launched.

And nothing happened.

All of our months of “marketing,” the countless friends and family who “couldn’t wait” to start using our app; none of it materialized. A month after launch, we had fewer than 150 users.

Months later, nothing had changed. But we kept on. We thought we were doing everything right. We had read all of the books.

READ ALSO – What Comes First In Entrepreneurship; The Passion Or The Idea?

We kept wasting time on things that didn’t matter.

Things got dark.

I slipped into what I now recognize as a depression. Colors became less vibrant. Music lost its magic. Things I once loved: working out, playing guitar, building my business, suddenly became chores.

As my leadership crumbled and our countless hours consistently let us down, we started losing focus. We started getting lazy. Our 7am team workouts became less frequent, then stopped altogether.

“The next feature will change everything,” I would say, reassuring my team and myself.

Anything to keep our thoughts from straying to that terrifying question:

“Is this all going to be for nothing?

To keep the business alive, we turned to friends, family, and yes, personal credit cards for funding. But it wasn’t enough. If cash is oxygen, we were holding our breath.

Then one day, we suddenly had an interested investor. I drove out to meet him in person (I’m intentionally keeping the details vague here, as he remains a close family friend) and he agreed to invest $50k, a godsend for us at that point. More importantly, he offered to act as lead syndicate for our entire round. In fact, he was part of an angel group that could meet with me the very next day.

Entrepreneurs Struggle
Image credit: Maskot | Getty Images

Ecstatic, and eager to build on this new momentum shift, I accepted on the spot. That night, I slept as if the weight of the world had finally fallen off my shoulders.

The meeting went smoothly, until it didn’t. After a streak of home runs, I foul-tipped a question. It wasn’t a big deal. But it was to one of the investors.

If you’ve ever watched Shark Tank, you can imagine what happened next. As if I weren’t in the room, the investors turned on each other. I watched in horror as bad blood splattered all over our chances at funding. They left, one by one, until I was left with the original investor who had arranged it all. None invested.

“Well, that was interesting,” I said to ease the tension.

“Yea, I’ve never seen anything like that. I have no idea what [Jeff] was going on about! But while we’re here…”

Words can’t describe how I felt as he told me he was backing out of the deal.

My desperate attempts to sway him were met with shifty responses about his conversation with his wife, and his liquidity, and all of that. But the truth was clear: I had failed, again, when my team needed me the most.

I picked my chin up as I looked him in the eye and shook his hand. I kept it up as I called my team to tell them the devastating news. I kept it up as I walked through the hotel lobby and up the elevator. I kept it up until my hotel room door closed behind me. Then I broke down.

But even as my single hope was ripped from the sky and crushed into the dirt, I did not let myself ask the question I feared more than anything in the world.

“Is this all going to be for nothing?

As I drove home, I tried to find reasons to keep going. I couldn’t find any, so I made them up as I pulled into the driveway. I mustered a fake smile and marched up the steps, determined to be strong for my team.

I could tell something was off before the door had shut behind me. My brother had a concerned look on his face. My co-founder walked in and asked if we could speak privately.

He told me he was leaving the team. He had said that he would be with me to the end, and I guess from his perspective he kept his promise. In his eyes, we had reached the end of the road. We had failed as a team. had failed him.

It’s a unique feeling, to pour your soul and every fiber of your intellectual, emotional, and physical being into something, only to fail over and over again. To have the evidence directly indicate that YOU aren’t good enough.

But there’s also something uniquely powerful about hitting true rock-bottom.

The Navy SEALs are famous their “40% Rule.” When you are ready to quit, when you KNOW it’s time to quit, you’ve only given 40%. You have more than twice as much grit and struggle left in you.

It’s hard to hit rock bottom. There are too many opportunities to give up, to pretend, to lie to yourself before you get there.

But when you do reach that point, you realize that you have what it takes to be an entrepreneur. Everyone else would have quit long ago.

A few weeks after my co-founder quit, my parents convinced me to take some time to visit them in Florida. The space and sunshine gave me time to think and reconcile the events from the past few months.

I couldn’t have known that I would bounce back from rock bottom stronger, sharper, and wiser. I couldn’t have known that we would figure out funding, and that the business would take off.

I do know that during that trip, I had an “AHA!” moment, and it all finally clicked.

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I realized that the raw essence entrepreneurship is inordinate risk, coupled with consistent disappointment and failure. I realized that, and I accepted it.

What prompted that breakthrough moment?

I finally found the courage to answer for myself the question I had feared for so long.

“Is this all going to be for nothing?

That answer was “No.

Struggle doesn’t break an entrepreneur.

It defines them.

Credit: Pete Ghiorse

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