“You need to come face-to-face with the past, not as some naive, easily wounded boy, but as a grown-up, independent professional. Not to see what you want to see, but what you must see. Otherwise, you'll carry around that baggage for the rest of your life.”

The entrepreneurial journey runs deeper than Facebook Ads, Co-working spaces, and drop-top Lambos. It transcends brainstorming sessions and well-orchestrated marketing campaigns because as the great Mike Tyson once said, "everybody has a plan until they get punched in the mouth."

How do you react when you take a hit? Can you maintain discipline or do your emotions consume you?

Entrepreneurship, similar to boxing, has NO room for emotion. Stepping into the ring with your emotions can only guarantee a loss by points, at best, or a knock-out. Emotions make it impossible to withstand the 100 “No’s” as well as the highs and lows.

More importantly, the process of removing my own emotions required coming face-to-face with my past. Often times, emotional reactions are a result of past traumas being triggered.

My fear of rejection in my business life stemmed from my problem with rejection in my personal life.  By getting to the root, I hoped to finally get an understanding of my problem with rejection and break down why I viewed failure as death and not as a lesson.

“You are only free when you realize you belong no place—you belong every place—no place at all. The price is high. The reward is great.” — Maya Angelou

In July, a couple days before The Bag Lady’s A-Alike article was released in a conversation with Danny, I subconsciously revealed that I based my value on the amount of or the depth to which others wanted/validated me.  

After I made the comment he responded, “Nate, did you deal with abandonment/ rejection growing up?” Being that it was such a loaded question I quickly replied “No”.

I responded “no” with such assurance because in my mind there was no way I could have. I grew up with both parents and I come from a HUGE loving family.

But as the conversation continued, it suddenly hit me like a sack of bricks, maybe I do have a problem with rejection? I decided then that this question was worth exploring more on my own.

The Romanticized Struggle

Unfortunately, too often in our community, the struggle is romanticized. Like any good novel, we want to start from the bottom and rise to the top. But life isn’t fiction,  it’s real.

Having friends that had no parents or one parent, I believed that coming from a stable two-parent home made me immune to abandonment or rejection issues. In fact, had it been someone other than Danny I may have been offended by the comment.

Growing up people attempt to make you feel guilty if you had a little more than they did and you dared to complain. Although I’m grateful and blessed, having parents, more money, or more influence doesn’t mean life won’t touch you.

Overcoming the idea that it was impossible for me to have a problem with rejection was the first big step in facing my past.


“Mentally strong people don't make sweeping generalizations when they're rejected. If one company turns them down for a job, they don't declare themselves incompetent. Or, if they get rejected by a single love interest, they don't conclude they're unlovable. They keep rejection in proper perspective.”

Whether it was on the football field or in the corporate office, my struggle with rejection was present in all areas of my life. And by making sweeping generalizations, I was subconsciously telling myself that I was not enough.

Some feedback I received from my Coach at PwC was that I’m not consistent. She said, “Nathan on some projects you perform really well and display qualities of a top performer. While on others you’re average and make some careless mistakes.”

Knowing this was true I thought it was connected to my level of autonomy. On projects where I had a lot of autonomy and felt empowered I performed my best, and when I felt like a cog in the wheel I got very passive.

But it’s deeper than autonomy. Inconsistency has been a running theme throughout my life. For some reason, on certain football teams, I played like a true champion and on others not so much. In certain classes, I was an avid participator and in others, I confused class with nap time.

The real issue was that my motivation was connected to external validation. Despite loving the game of football, it was difficult to honor the craft when I thought my coach and teammates saw me as a throw-away and not an essential member of the team.

Or in class, my level of participation sharply declined if I felt that most of the class was smarter than me, believing that my perspective and opinion was no longer valuable or enough.  

This desire for external validation created the two driving motivators in my life, the desire to either prove someone wrong or make someone proud.

Prove Others Wrong

One Friday, in late July, I was having one of those NYC summer nights.  It was 3am and I was about to walk home after an eventful night when I met a group of friends from Canada/UK who were looking for a late night meal.

Being the kind soul that I am lol, I took 4 of them to get empanadas and the last one to get pizza. On our way to the pizza spot around the corner, Mowgli and I had an interesting but unexpected conversation.

Walking and talking, he said, “Nathan, I feel like you are too hard on yourself. Idk what's telling me to say this but I sense something and I feel like you need to hear it. The world will shit on you so there's no need to shit on yourself too. You are great and you are going to be fine.”

Experiencing rejection throughout my life I’ve always had an enormous chip on my shoulder to prove others wrong. And since a lot of successful people discuss how they leveraged the chip to get to where they are, I thought it was ok.

However, from that conversation, I realized that although the desire to prove others wrong will allow me to accomplish my goals/dreams. The desire to be my best self will get me there with less baggage, allow me to enjoy the process, and result in fulfillment when the goal is accomplished.

Baggage -  The passion to prove others wrong is fueled by the pain of rejection. I have every college and company rejection letter. One day when I finally “make it” I plan to call them out for rejecting me, hoping they would be consumed with regret and experience the hurt I felt. That Friday night my friend recognized I was carrying a load that I needed to let go in order to move forward.

Process - “The journey isn’t so much about becoming someone. It’s about getting rid of everything that isn’t really you.” - Paulo Coelho When I aspired to prove the naysayers wrong my actual goals became secondary. Above all was the ambition to prove them wrong. This makes it impossible to enjoy the process because I get consumed with getting to a place where I can say “Hi Hater” or more like “Bye Hater”. Lol When you aspire to be your best self you can embrace that every day is an opportunity to progress. The process is no longer a means to an end but an enjoyable experience.  

Fulfillment - The accomplishment won’t fill the void. When I first started writing I was waiting for my break-out article. Last July I met the Co-founders of Goalcast and I was able to get an article published on their website which got over 1,000 shares. At the moment it felt great to finally have my work recognized but after a while the void I’d suppressed, reemerged. I began to wonder when my next big article would come. However, now I take great pride in writing daily because each day is an opportunity to sharpen my saw. I truly enjoy the process and it’s no longer about having an article that goes viral but getting better every day.

Unconditional Love?

Quitting PwC further exposed my fear of rejection. Despite making the decision on the night of Tuesday, August 7th, I couldn’t muster up enough courage to tell my parents until Sunday, August 12th. Because I knew that it would be difficult for my mom to understand and I didn’t want to be rejected.

The day after dropping the atomic bomb, in typical Nate Perro fashion I left home and returned to NYC. Despite usually calling my mom during my afternoon walk each day, I avoided calling for a few days. I could sense the potential rejection in the air. And it came.

About 70% of the time before getting off the phone my mom and I say “I love you”. When it was finally time to hang up, my chest started to beat. I was waiting to see if she would say it and when she didn’t I was crushed.

Although it happens about 30% of the time and I normally think nothing of it. This time it felt like me quitting my job was the reason.

I knew it was a serious problem when the next time we spoke and 100 pounds came off my shoulders when she said: “I love you”. At that moment I realized that my concept of unconditional love was flawed.

That although in my head I believed it was real, in my heart I felt otherwise. The shift happened during my childhood. Usually getting a “D - C” on my weekly Friday report, one week I wrote my own grade, giving myself an “A - A”.  

Thrilled by the improvement, my parents took me to Giant and I got two packs of Reese's Cups. Despite feeling guilty, the love and attention felt worth it at the moment. I was finally the good kid.  

But that all came crashing down when I got caught. Although mentally I knew they were in their right to punish me, in my heart I felt rejected. Being on punishment and receiving the cold shoulder from my parents for months, I felt like the black sheep of the family.

Over the past few months, I’ve been trying to figure out why I struggle with saying I love you first. Three simple words shouldn’t cause my stomach to turn upside-down especially when it’s to a parent or sibling.

It’s my flawed perception of unconditional love. In my heart, I believed that when things got tough or I was no longer an “A - A” student, that the people who claimed to love me would disappear.

The fear of abandonment resulted in me being afraid to say it first. Also, believing that vulnerability was a weakness, I subconsciously thought by getting others to say it first gave me power over them.

So when they did leave, I could trick myself into believing that they loved me more to cope with the pain.

“Someone’s ability to love you has no bearing on your lovability” - Brene Brown

In a recent interview with Lewis Howes, Kobe told a story about his experience in a Philly summer league that he played in at age eleven. After playing for the entire summer he scored zero points.

Disappointed, his father said to him “Whether you score 0 or 60 points I’m going to love you no matter what.” Kobe said that gave him the confidence he needed to fail.

The rejection I experienced in my moments of failure conditioned me to believe my lovability was connected to my success. But Brene Brown reminded me that we are inextricably connected to each other in a way that is unbreakable.

Operating in this new understanding allowed me to realize that failure does not mean death. In fact, as an entrepreneur, I’m supposed to “Fail fast, fail often”.

Permission To Fail

After watching the Kobe interview I thought hearing my parents say, “Nathan we give you permission to fail” would relieve some of the tension. However, after hearing comments from them such as,

“why didn’t you stay longer at PwC and wait until you completed more deals? The real estate market isn’t doing so well. I don’t understand why you are making this move.” I decided to give up on asking for permission to fail and grant myself permission.

Recently, I watched a Jeff Bezos interview where he discussed what his wife/parents said when he decided to quit his job and start Amazon. In short, he said, “My family bet on me. They believed that I could be successful not necessarily Amazon.”

His remarks reminded me of a popular saying within the Venture Capital space, “bet on the jockey, not the horse”. Meaning invest/place a bet on the person, not the business.

Regardless of their intentions, the boatload of questions asked in doubt by my parents communicated, Nathan you are not a capable jockey, you’re not enough, and you don’t have what it takes to be successful.

And although it was a difficult pill to swallow and it took some time to understand, every day I remind myself that people will not always understand what you are called to do. And that’s it not my job to make them understand rather just live in my purpose.

Build A Foundation

“You’re building up without building down...And it’s shaking because it was built on a weak foundation.” - Eric Thomas

In the False Prophets article, I wrote about receiving the “Outstanding Black Student Award” for the class of 2016 at the Multicultural Student Services Center graduation and how I felt unworthy.

At the moment, I perceived that my lack of clarity on my future/career was the cause. Believing that I was undeserving of the award because I didn’t have it as together as it appeared. But I now understand that it was a bit deeper than that.

In that article, I was speaking from a perspective that assumed progression only required leveling up or building on top of what I had already created. I now realize that no building can stretch beyond the strength of its foundation.

In other words, to build up I had to first build down.

Mentally I still saw myself as the same Nathan whose parents wanted to put him on hooked-on-phonics/almost got held him back. Originally, I thought it meant that I was humble because I hadn’t forgotten the glo-up.

But my fake humility was a result of not dealing with the pain and holding on to it for so long that it became a part of me. I still saw myself as less than. Not really knowing my true value.

The optimism of believing I could be great and well accomplished despite never fully seeing myself as larger than life got me to this point. And as my future got brighter, I thought I could just move on without addressing the darkness of my past.

Prior to this moment, I thought optimism/ positive thinking was all I needed. But what got me to where I am now, cannot take me to where I want to be, optimism wasn’t enough.

As I alluded to earlier, every new stage requires more digging because to build the biggest building in town I needed to have the deepest/strongest foundation.


Over the past 8 months, writing has meant more to me then just sharing my story and breaking down different concepts. It’s become a platform for therapy and self-healing.

But being that quitting my job was the most difficult decision I’ve ever made, my emotions escalated to a point where writing was not enough.

It got to a place where my thoughts had to transition from being in a Google Doc to being apart of the difficult conversations I needed to have to begin tearing down the wall I had built between myself and the world.

Over the past month of being home, I’ve danced with rejection and wrestled with my fear of abandonment. It’s been an uneasy experience but in all, it has strengthened my relationship with my parents because they’re finally getting insight into who I am.

And although the difficult conversation I had with my mom didn’t go as well as I would have liked, having it has taken the burden off my back which has resulted in a higher level of self-awareness and confidence in who I am and what I’ve been called to do.

In parting, get it off your chest! A year ago I thought the only thing on my chest was an “S” which stood for Superman Perro. Lol I had gotten so used to carrying the load that I didn’t realize it was there until others began to point it out.

Moreover, I started off this year with the goal of facing my issue with vulnerability and it took me 11 months to pinpoint the exact location of its root. So if you find yourself on a similar journey, just keep doing the work. It won’t be easy but it will pay off in the end.