November 20, 2017

5 Reasons Why I Left A Fortune 50 Company To Join A Startup & Become An Entrepreneur

Not long ago I found myself in a conference room, accompanied by a handful of individuals, as well as the Vice President of finance and other high ranking executives from a Fortune 50 company.  Now, you’re probably thinking, what an incredible opportunity right?  Well, not quite.  

You see, I always knew I wanted to get involved in business and one day start my own.   Throughout my life I played basketball and worked out tirelessly, to the point of an obsession I will admit.  I remember having anxiety on my days off and never felt accomplished until I had multiple workouts completed.  NBA star for the Cleveland Cavaliers Isiah Thomas has this montra “stay paranoid,” and I lived by this; working out as hard as I could imagining someone was coming to steal my spot.  So, I have an inkling that the inception of my desire to build a business came from that competitive, obsessive nature of proving myself on the court.


Therefore, upon graduating from college, I believed a fantastic way to learn how to build a business was to get involved with an extremely successful company, and in my case that company was United Parcel Service (UPS).  My thought process was working in finance with a Fortune 50 company would be the opportunity of a lifetime to learn how a business fiscally operates and how they manage their funds for continued success.  Money is the oxygen that allows a business to breath, so a finance position at a Fortune 50 company seemed like a no-brainer.  Quickly, I learned quite the opposite.

Now, before I get into why I decided to quit I want to make clear that the people I worked with everyday were truly amazing people.  I am extremely thankful for the relationships I have built and can honestly say I have life long friendships that were constructed during my time there.

Working with such a large corporation, as you can imagine, there was a ton of bureaucracy.  UPS employs roughly 400,000 people which in itself is amazing and the work they do is top notch.  Getting a package from Europe delivered right to your doorstep on time, still fascinates me.  But, the size of the company created a situation where being innovative was difficult.  

I wanted to learn how to build a business, how to improve as an entrepreneur, be a part of innovation and learn how a business operates fiscally, yet I found myself in almost a secretary type position.  I sat at my desk staring at two computer screens, doing the same thing each and every single day, often having the feeling of dejavu.  I had to dress a particular way, had to keep clean shaven, was held accountable to a 30 minute lunch break which often led me to eating at my desk while working, my ideas were not heard because I was not one of those “higher-ups,”, I was never once asked what my long-term life goals were, the monotony of it all was eating at my soul.  I felt like a robot who was programmed to do the same thing everyday and keep quiet while doing so.

I could not stop reminding myself of the Henry David Thoreau quote where he so famously stated “most men lead lives of quiet desperation.”  I knew I could not grow into one of those men, and then it finally hit me, I needed a change.  I needed a spark in my life.  

I recently spoke with entrepreneur Jon Vogel Co-Founder of 215 Marketing on my podcast and he said something that resonated with me.  Jon, when speaking about sparking a change in life, stated “it’s about looking in the mirror and fundamentally challenging yourself and sacrificing who and where you are, for who, and where you want to be.” After speaking with Jon, some family and friends, I knew what I needed to do.  And that was the day I put my two weeks.  What a liberating feeling that was.   

And so, I decided to reach out to a few startups in the Philadelphia area where I knew I could grow and learn.  Thankfully, I was able to connect with Mac Frederick at Momentum Digital.  Below are my five top reasons why I knew leaving the security of my well paying finance position at a Fortune 50 company and joining a startup would be worth the “risk”.

  1. Mentorship & the Ability to Learn Directly From A CEO

This one is pretty simple, if you want to get good at basketball who would you rather consult, LeBron James or Mick Jagger?  At a startup you are fortunate to work directly next to the startup’s CEO in most cases.  This was the leading factor in me joining Momentum Digital because Mac Frederick is a proven entrepreneur who values mentorship.  Having the ability to work closely with an individual who is building a business or for Mac’s case, has built multiple, is an education that you truly cannot put a price tag on.  Therefore, if you have the inkling that you are an entrepreneur or want to build a business, working for a startup is the perfect place to do so because you will see how a CEO operates on a daily basis and understand their vision and what goes in to their decision making process.  Working for a large corporation you may never have the opportunity to work closely with their CEO or even meet the CEO.  I’ve learned over the years how crucial mentorship is for success and this was a huge factor in me deciding to work for a startup.

  1. Culture By Design

Company culture is one of those cliche sounding topics but from firsthand experience, I can see how it creates problems when not done properly.  I was exposed to working in an environment where there was no emphasis on culture, but more about doing things how they have always been done.  Company culture, when done right, allows employees to feel like they are cared for as a person first and an employee second.  This is huge for productivity and an overall vibe in your workspace.  Something that I craved was to be apart of creating that culture, to create a positive workplace and not an environment of “this is how it has always been done.”  I love what John Tabis CEO of The Bouqs said about the importance of company culture when he stated “when employees feel cared about as people, I’ve found they do their best work. They also stay longer, work harder, and produce more, which makes caring an amazing rate of increase.”  I can attest to this because if the person I am working for is willing to create a strong relationship with me not solely based on work, then I know they care about my success and in turn I will go above and beyond because of that relationship.  It’s a win win.

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  1. Size Does Matter

Who doesn’t like to have their voice be heard?  I would assume not many, just like myself.  Working for such a large corporation there are tons of employees and layers of management which can create a situation where your voice is drowned out and this is quite the opposite at a startup, hence, size does matter.  When working for a startup something that is always present is continuing to generate new leads, sales and ultimately, to make more money.  Therefore, this creates an environment where ideas need to be valued and listened to.  Mac Frederick preaches this concept.  He believes, as many other startup CEOs do, if you have an idea please speak up.  If you hire smart, driven and talented people then those people will most likely be constantly thinking of how to better contribute to the team and grow the business.  It is in everyone’s interest, especially if the startup offers equity, to make sure the business continues to grow.  I wanted to be a part of an environment where I could not only learn but one where my ideas and voice would be valued.

  1. Be A Part of Disruption

I have alluded to this earlier, but when working for a large corporation there is a lot of bureaucracy and levels of management.  When a company operates at such a scale and also one that is publicly traded, innovation and implementing new strategies can be quite sluggish.  We all have seen firsthand how Uber disrupted the taxi industry and how Netflix put Blockbuster out of business.  Whether it is my background in sports or the social media generation I’ve grown up in, I love that fast-paced mentality. I love innovation, new ideas and disruption.   

When speaking with serial entrepreneur Rob Monster, CEO of Digital Town, he stated he left P&G after nine years because he wanted to build something that would disrupt the e-commerce giants in the world and help empower local communities and small businesses. Working for a startup I have that ability to be apart of building a business that does things differently and potentially disrupt the digital marketing industry.  Startups have more freedom to take risks, try new things and lead the way for disruption.  When Momentum Digital laid out some of their plans moving forward to do things differently and disrupt the digital marketing industry, I had to be a part of that.

  1. Create Your Own Lifestyle

This last reason encompasses a little bit of the prior four points in the sense that they all contribute to growing as a person and as an entrepreneur.  When working for a startup you absolutely need to be entrepreneurial in finding solutions to problems and be a self motivated person.  Working at a startup you will be able to learn directly from the CEO how they are building their business for you to one day do the same.  And, in doing so, as an entrepreneur, create your own lifestyle.  I love the way serial entrepreneur Suzy Ryoo, Venture Partner and VP of Technology & Innovation for The Atom Factory & Cross Culture Ventures phrased it when she stated to me ”Work tirelessly to build your own adventure.  Be patient, take big swings, and surround yourself with peer mentors along the way. Make your life an iterative, passionate journey of doing what you love.”  This summarizes my thoughts on working for a startup beautifully; I wanted to surround myself with other like-minded individuals and receive that mentorship to one day build something of meaning and be passionate about what I am doing with my life.  I want to create my own lifestyle and being apart of Momentum Digital and the startup scene, I know I will be equipped with the necessary tools to do so.


In conclusion, I wanted to write this article because of how passionate I feel about this topic.  I have plenty of friends and family members who work for large corporations and have had similar experiences that I had.  One thing that I want to state loud and clear is, you have control of your life.  Please do not allow the facade of a well-known brand name and consistent paycheck chain you down from chasing a life with more meaning and more purpose.  I knew I wanted something more.  I knew I wanted my voice to be heard.  I knew I wanted more responsibility.  And I knew I wanted to be apart of building a company that has an emphasis on people first and developing their people as entrepreneurs.  I ask of everyone reading this to not be that person leading a life of quiet desperation, but one that constantly seeks to improve theirs and others lives.  Do your due diligence in researching the startup or new company before joining, but please do not be afraid to take that leap of faith and take that less traveled path that Robert Frost stated because you never know, it could make all the difference.  If you found any value from my story please share this so others can hopefully gain something from it as well and I would like to challenge anyone else who had a similar experience to write about it.  Design the life that you would love to lead, not the one that is designed for you, but by you.

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