5 Lessons from an English Major Turned Entrepreneur


Originally written May 1, 2012

I recently gave a talk to a group of students, faculty & staff who participated in Career Week at my Alma Mater, UMBC. The talk was titled: “Blue Skies & Beyond: 5 Lessons from an English Major Turned Entrepreneur.” The theme was “real life after graduation.”

I was not only honored by the opportunity & experience, but it was also an amazing opportunity to look back on life a bit, and think about some of the important things that I’ve learned along the way. The list began to get very very long, so I had to force myself to filter the list down to a few key lessons that are embedded into the fabric of how I operate today.

I also thought about what might be motivational or inspiration for the audience. What kind of information may help them take the next step or make the next move to go for their own WIN, in all of their pursuits.

The talk was probably the most personal I have ever given. Thats not too surprising since it was about my story and my journey. I started from my early days in high school and went all the way through starting & selling Blue Sky Factory, and finished with the efforts that I am working on today. The talk was a great framework for future speeches, and can be greatly expanded on.

So, with that I wanted to share the 5 lessons that I spoke about, with a little bit of commentary on each:


1. Never Doubt Yourself: You are capable of FAR more than you can ever imagine.

When I was in high school, my high school guidance counselor told me not to bother applying to college. Given my performance in high school, he felt I was best suited to attend a vocational school in hopes that I could obtain a skill like an electrician or a carpenter. The theory was, develop some kind of skill set now, so that I would be employable after I graduated from high school. The message was loud and clear, university was not in the cards for me. This was the best advice that my high school guidance counselor had for me.

I’ll never forget the UMBC commencement in May 1997, and the sense of achievement that I had when I personally mailed that high school guidance counselor an invitation to attend my commencement ceremony. Needless to say, he didn’t show up 

The important thing here is to realize that occasionally life delivers you experiences when others doubt your abilities, and sometimes, if we don’t persevere in our own right, we can fall into the “trap” of believing those people. This lesson is really about never falling into that trap.

I can only imagine what my life would have been like if I had taken the advice of that high school guidance counsellor.

2. Be Curious: Experience as much as you can.

Many folks don’t know my back story, and the very odd path I took to entrepreneurship. I came to UMBC for an Emergency Medical Services degree (they have one of the best programs in the country). When I was 16, I had been a cadet on my local first aid squad in New Jersey. I quickly became a certified EMT (Emergency Medical Technician) for years before I moved to Baltimore in 1992.

I was two years through the program when I had an epiphany about my life. I quickly realized that I no longer wanted to go down the path of a career in EMS. I pondered for a semester while I picked up some elective courses, then decided on an English degree. My thesis for English, was that no matter what I did in life, I would need to know how to read and write well.

My path to entrepreneurship was a culmination of experiences and exposures throughout college. Think about this: I’m a former student of emergency medicine, turned English major, turned marketing technology entrepreneur. A wild road indeed, and it was a series of events and experiences that exposed me to the people and things that would shape my thinking, interests and ultimately my opportunities.

When I was a student at UMBC, I was busy living and being active in a variety of activities outside of my studies. I was involved with the Student Events Board, a fraternity, held an on campus job as the tech crew manager, was an off campus promoter, etc.. its no wonder I didn’t have a 4.0 GPA, I was busy living at a young age 

So, how did I find my way to entrepreneurship? I truly believe that it was my sense of exploration and curiosity, and having a generally open mind that led me to a series of collective experiences that put me where I am today.

As I said during my talk, when I was a senior at UMBC if you told me I was going to start, scale and sell an email marketing company, I would have told you you were nuts 

Keep your mind open and always be learning and exposing yourself to new things. You never know where you will find your calling. Keep that sense of curiosity flowing.

3. Trust Your Gut: Your sixth sense never fails you.

When I tell the story of Blue Sky Factory, I’ve been known to say that I ran the company for 10 years purely by my gut instinct. I’m known to say this because its true. All of the constant managing, maneuvering, strategy, developing the vision, thinking ahead, hiring, making timely big decisions, etc.. all of those things as I look back on them were yes sometimes made with the help of facts, but ultimately most were made on my “gut feel.”

I know many great entrepreneurs who feel the same way as I, and in my talk I mentioned the large amount of test data that I have on this 

When I look back on the things that never sat right in my gut, or didn’t “feel” like they were in the flow, and also when I allowed myself to be influenced by other people even when my gut was crawling, those were things that ultimately either didn’t work out or had less than desirable outcomes. I am not sure how you describe the feeling I am talking about exactly other than, you just know. Its innate in all of us.

I recommend reading & tracking that barometer closely.

4. Make Bold Moves, Take Risks: They move you further than you could ever imagine.

There is no doubt you’ve heard the saying before, no risk, no reward right? Many of you know that its a true statement. One example I would like to share with you follows: In life, we are presented with a variety of options for our career paths, and much like the earlier thought on continuously nurturing your curiosity, sometimes the comfortable option, or the path of least resistance, is not always the best option in the long run. And sometimes when you DO introduce a little bit of risk and challenge into your life, things can change, forever.

I’ve also come to realize that there are very defining moments in life when you make a decision to either do something or not to do something, and that decision could literally be a fork in the road. The decision you make can impact your future in a very big way.

Before I started Blue Sky Factory, I briefly worked for a startup in the Emerging Technology Center in Canton for a year, it was the only job I ever had after I graduated from UMBC. When I decided to leave that company at the age of 27, I was being courted to join another startup based out of Philadelphia as a regional biz dev rep here in Baltimore. The job came with a $90k salary, a commission plan, and equity in the company. A rather compelling offer for a 27 year old who was making $50k at the time. I was greatly pondering this opportunity versus starting my own company.

Clearly, the job offer was incredible and would have been the comfortable choice and most definitely the path of least resistance for me. It was either that or starting up a business in an absolutely horrible economy with no money, and no chance of getting any investment.

So, what did I decide to do? Of course, I turned down the job offer and started up Blue Sky Factory in one of the worst economic climates (March 2001) with no money, being forced to bootstrap ie. white knuckle it. A defining moment in my life for sure.

Much like the story of my high school guidance counselor, if I had taken the “advice” or in this case “the easy path,” the past 20 years of my life would probably look a lot different. If you are new to my world, the story of Blue Sky Factory ended very well. As for the company in Philly, they closed the Baltimore office a year after they offered me the job, and closed their doors for good a couple of years ago.

In my life, as I look back so far, there were many defining moments based on decisions that were bold and full of risk. In all of our lives we are presented at one time or another opportunities like these. These can be defining moments, ones that you find out what you are made of. So, in short, be bold and take risks! If you continuously play it safe and take the path of least resistance, you are going to be leaving a lot of personal growth, self discovery and overall awareness on the table when it comes to life. Just my personal $0.02.

5. Stay Humble & Have a Sense of Mission

“Check your ego at the door.” You may have heard that statement before as well, and I have found that its a very POWERFUL statement as well as a POWERFUL practice, and has served me well in both life and in business. Lets face it, no one really likes to be around with someone with a big head or who comes across as if they are above everyone else in the room. I call those folks “Oneupsmen,”  No matter what, they are always bigger and better in everything being discussed and their head is BIG.

There are many lessons in life, and in business, and I believe if you take each of your lessons to heart, they should ideally lead you to a state of humility. You should continuously be in a state of thanks and humility for every lesson you receive in life. My life’s work currently is focused on helping other entrepreneurs achieve their dreams. I take the lessons very seriously, experience & knowledge gained is critical in every situation.

When I think back on my early days at bootstrapping Blue Sky Factory, and what I learned from the UBER lean days, when there were just a few dollars in the bank, and when often there were no dollars in our pockets. Back when we lived on peanut butter and jelly sandwiches, and the mere thought of taking out our then girlfriends, now wives, couldn’t even enter our minds as a possibility. Times like that will humble you. You don’t forget, nor should you. Give thanks for everything you have no matter what, and try to help others achieve their dreams if and when you can. In short, karma is what karma does.

This was the overall theme and thesis of the 5 lessons that I chose to share with the audience at UMBC. I had about 12 pages written out and I read, off paper, for the first time, a very personal speech that gave a little insight into the fabric of this entrepreneur.

The feedback overall was great, and I enjoyed talking to the future generation for quite a while post-event. In closing, these are just some of my truths based on my own experiences. My only hope is that some of the above either inspired or moved you in some way. I would love to hear your thoughts, reactions and additions in the comments. Thanks always for reading.