A Chip on the Shoulder

Sean Scott
6 min readJul 21, 2021


I had no idea we were a “week to week” family growing up. Food was rationed but I thought it was just due to principle, not economics. Rice was at every dinner to fill us up. Milk was never drank; only to be used on off brand cereal. We were always full though. House was warm. Family meals were always together. I’m sure my dad was stressed looking at the checkbook; something I didn’t appreciate until becoming a father.

So when I was offered $400/wk, 23 years ago, to hang out with two little boys from NYC from the summer, I thought I had hit the jackpot! The family was based in Manhattan during the school year but lived up in the Berkshires for the summer. Their house was a damn mansion to me! I didn’t recognize the difference in what life could be until I started working for them. Everything from appliances to sofa materials to cars (never mind the daily eating out) revealed a whole new world of access and privilege. It was fascinating to see how loosely money was spent. How could anyone afford to pay someone $400/wk to hang out with their kids WHILE they were home?!?!? Blew my mind.

I spent the next 6 summers with those boys. My relationship grew with the family. They always treated me well and valued who I was. But as the years progressed, the allure of their life faded. The dad wasn’t home much. He flew in via helicopter/drove from NYC on Friday night and then left at 4 am on Monday. His mind was occupied. Never fully present. He was about my age at the time. I could sense that there were issues in the marriage.

Being from a poor/lower middle class family, I always felt insecure though. I knew my path through life wasn’t like theirs. But maybe it could be? Maybe they saw something in me that would prompt them to invest in my life beyond just babysitting their boys. The husband took me to work in the exchange a couple times. He traded futures in oil, gas and wheat. I remember vividly standing on the floor, mostly men yelling, pushing and speaking in a language I couldn’t comprehend in the least. It was a fraternity of sorts. The two days I was there, they made fun of me for the shirt I was wearing. I didn’t care. At least they noticed me. But the stress was real for them! That was apparent.

After that experience, and watching the grind of his daily life, the toll it took on his family, I wasn’t interested in pursuing that path. I wasn’t great at math and most definitely couldn’t do it as quickly as trades required so I quietly declined any invitation (if there even was one.) I can’t quite remember if there was an offer or if I had just imagined one, hoping he saw the talent in me.

Fast forward about 2–3 years after I had stopped working for the family. . . I had started the initial exploratory phase of launching my first coffee shop. After many months of research and meetings with electrician, plumbers and equipment dealers, I had learned everything I could about the business of coffee but ran into the block most do when trying to start a company . . . access to start up cash. At the time, I was making $26k yr and had a loan on my car. Zero collateral. A 780 credit score but that was it. Not exactly the safe investment a bank is looking for when lending. I clearly remember the banker looking over my business plan and saying, ”Wow! This looks great! Really clear and thorough. But you do realize that we need collateral in order to lend to you? Do you own a home? Have about 20–30% of loan amount in cash?” No. Nope, don’t have that either. I was quickly realizing that I’d need to find someone that believed in me if I would ever be able to launch this dream of mine.

My network was only made of other blue collar people that didn’t have the margin in their own life to give money to a young start up. But I did know the family I’d worked for. I didn’t know their net worth but I did know they lived next to Robin Williams in a high rise over looking Central Park west, subsidized a couple off broadway theaters and had a small mansion in the country. Those three seemed to indicate that the $20–30k I needed as collateral wouldn’t be a problem. They knew me well, trusted me with their children so they had to believe in me, right?

I nervously called “Steve” and shared what the plan was. I said I could email the business plan for more details and answered all his questions. I felt completely prepared. He was my ONE way to reach the goal. But I’ll never forget his response.

I was sitting on a plane, at the end the 20 minute conversation with him and he said, “Sean, I appreciate you sharing. You’ve definitely done the groundwork you should. But the food service market has an extremely high failure rate. I don’t feel comfortable investing at this time. Good luck and we’ll talk soon!” That was it. No discussion. The air left my lungs. Just like that, the dream felt as out of reach as the moon. But it wasn’t just the money. It became clear as day that he turned me down because he didn’t believe in me. He could lose all of that seed money and never even notice it was gone. A literal drop in the bucket. So if he didn’t value me enough to even risk that money, it seemed like who I was to his family wasn’t worth that much at all. Six years of relationship that didn’t even = $20,000 to a multimillionaire. Ouch!

I never had a chip on my shoulder until that moment. But it’s funny how rejection can do that to you. It can strike SO deep that it shifts who you are and what motivates you in a moment! It did to me. I’ve never been the same since. The fighter in me was born. Once that initial disappointment faded, a fire replaced it. I had no idea how I’d achieve my goal but I was going to. As I often tell people, even if I wasn’t offered a seat at the table, I’d build one and pull it up so I could be part of the conversations I needed to be in. You could be damn sure of that!

Twenty years later, I think about that moment of rejection often. Each victory won, each successful venture birthed, each conversation with those that are “out of my league” had, I thank Steve for lighting that fire in me that has now turned into unshakeable confidence. When you’re younger, there only seems to be one path to success. It looks like it is impassable and full of immovable hurdles. But that just isn’t the truth. If you’re determined, smart and thorough, you’ll have that Matrix moment at some point. Everything shifts from 3 D into seeing the code behind it. You start recognizing another opportunity to explore rather than a boulder to climb. You care less about the degree you have and more about the ability to access creative innovation that is seemingly without end.

I was talking with a buddy the other week about how I approach important pillars in my life that tend to lead to opportunity. I focus on about 5 things and strive to be in the top 5% in each. If you can achieve that through focus, relationship, determination and creativity, GOOD things happen! I promise you that. Don’t try to be everything to everyone, just be REALLY good/competent/intentional in a hand full of things!

And let the path evolve! What once was just a coffee dream is now a spider web of ventures that have a common thread but are drastically different in application. It creates such a fun and fulfilling life! The streets way of giving you an MBA-

I share all that to encourage you if you’re still seeing roadblocks and feel like no one believes. See rejection for what it is. Learn from it. Work on yourself. See others for who they are. Let it motivate you. Understand how to keep your fire alive. Understand how things work. Pivot quickly if need be and then get comfortable with risk! Failure WILL happen but it’s way more important in how you react to it.

So Steve, thanks for giving me that chip on my shoulder! It’s now a building block for my life. I built it into the chair that now sits at many tables of influence.



Sean Scott

I create space and experience…. and write a bit.