Cup 20

Person: Sam Rosen

Drink: regular coffee at Lovely, a bake shop

If I handed you a pen and said, “what is this?” you would say “a pen.” If I asked what you do with a pen, you would say, “write.” And you would be correct because that’s what it is, and that’s what it does.

But what if I handed the same pen to a dog? He wouldn’t use it to write, he would use it as a chew toy. Is he wrong? No, from a dog’s perspective, a pen is more useful as a toy than writing tool.

Hand the pen to an absent-minded college student and it could become a bookmark. An engineer might see it as a bunch of parts—a plastic casing that holds a tube of ink with a dispensing mechanism. You get the picture.

A pen doesn’t have to be a pen—it can be whatever you make it.

This was a concept Sam Rosen told me after we’d been volleying stories back and forth for 45 minutes inside an adorable café. The snow outside was blowing fiercely, but Sam’s relaxed demeanor and creative perspective made for easy and enjoyable conversation. I told him a little about myself and he chronicled the bohemian steps he had taken—starting from his formidable years spent behind a computer—that led to his current role as a founding part at One Design Company.

At some point in the conversation, he stopped and said there were two ideas he lived by. The first was a quote by former US baseball administrator, Branch Rickey:

Luck is the residue of design.

The second, a Buddhist principle he explained with the pen parable—a lesson in perspective and value—a reminder that there is more than one right way to approach a situation.

Sam has an interesting approach to life, especially school. One of the first things he said to me was that he always knew he was good at computers—not necessarily the best, but certainly good enough to make it into a career. The value of a traditional education wasn’t much to Sam, he had self-taught skills and knew what he wanted to do with his life. Arbitrary learning didn’t seem worth the effort.

That perspective likely explains the 2.1 GPA on his high school diploma. In fact, during his last week of high school, he had to beg one of his teachers to give him a passing grade so he could graduate. 

It’s not that he wasn’t capable of getting good grades. Sam decided he wanted to go to the Art Center College of Design in Pasadena—a leader in art and design education. He had visited the school a few times before he applied and he fully understood getting in was a stretch. The school rarely admitted anyone under the age of 20; the average age of an incoming freshman was 28. Sam applied anyways. He didn’t get accepted, but he did receive a handwritten rejection letter saying they liked him, but with a 2.1 GPA, they weren’t sure he could handle the rigorous academics of the school.

They said if he went to another college and proved he could get good grades, they would let him in. The value of school had changed for Sam; it became his passport to Pasadena. He spent a semester at Colombia College in Chicago, finished with a strong GPA, and transferred to the Art Center.

He left after a year. From his perspective, college was just a place where you spent a lot of money so someone could force you to do work and then criticize it when you finished. Sam had been starting projects his whole life; he didn’t need to pay someone to for that, so he dropped out.

At that point in time, he found work with a web-design firm. The owner, who made $150 dollars an hour for each project, would contract work to Sam, who worked for $50 dollars an hour. Sam looked at the situation and realized something—if this guy could make $150 dollars an hour and Sam was doing most of the work, there was no way Sam couldn’t do the same—or better. So he decided to start his own web design firm.

He figured if his idea failed, he would just go back to working for someone else.

That was six years ago, and from the looks of it, he won’t need to apply for jobs anytime soon. One Design has seen double-digit growth for the last five years, has about a dozen employees and a client list that includes Groupon, Xerox, and New York Magazine.

Sam’s approach doesn’t work for everyone—in fact, it doesn’t work for a lot of people. But Sam was successful because he was passionate about what he was doing and willing to spend hours developing his skills. Whether knowingly or not, Sam took an honest assessment of himself—his likes and dislikes, strengths and weaknesses—and decided what path worked best for him. With a supportive family and the courage to take calculated risk—he made his approach work. 

Which leads back to the first idea he told me about: luck is the residue of design.

Translate that with a thesaurus and you get: good fortune is the remnant of ambition.

Essentially, when you put yourself out there for something you’re passionate about and you pursue it with tireless effort, opportunities emerge, unexpected doors start to open. The lucky people in the world are those that go out and create their own luck. Sam’s ambition created opportunities that helped One Design prosper. 

Now, I’m not advocating a lax approach to school, or dropping out of college. I’m simply pointing out the value of finding what works best for you. I told Sam about my approach to school, which was the opposite of his. I had the perspective that if I didn’t do well in school, get into a good college, and earn a college degree, I would let myself and my parents down. As a result, I was a devoted student and left school with a great GPA. My approach served me well; my academic record helped me get a scholarship to Michigan State, which was exactly where I wanted to go.

Just like there is more than one right way to look at a pen. There is more than one way to approach life, school, careers, etc—pick one and put in the effort to make it work.

That’s a reoccurring lesson I’ve been learning over the past 20 cups. But what was different about Cup 20 is that instead of helping me find my own approach, Sam reminded me to respect the choices others make. Everybody’s approach is different. and just because they don’t do things your way, doesn’t mean they are doing things the wrong way.

I don’t want people judging my life ambitions, I shouldn’t judge theirs. Because it’s easy to discount the kid that barely survived high school and left college early.

But one day, that kid could be your boss.