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Stern Singles Presents: Ryan Mason

Overheard during one of my first experiences at Stern, at a Red “Block Game:”

“Wait, which one?”

“The tall, cute one. In LIO with us, he’s smart.”

“No. The one without the beard.”

“Oh, he IS cute!” 

“Yes! I know, I told you he’s hot!!”

This mysterious man, my friends and fellow classmates, is Ryan Mason. The man of the hour and the hope for all single Sternies. An admired man, whom I would bet, will not be on the market for long. 

Just take a look at his professional career! Ryan started as an analyst at an ad-tech startup out of undergrad. Soon, he shifted gears to join VaynerMedia, a large independent  media consultancy, where he worked to build up the media buying & analytics practices under Gary Vaynerchuk. Over 4+ years, Ryan held a number of different leadership posts across Gary’s holding company, VaynerX. He eventually made his way to BCG to join their Digital Ventures group, where he helped build and scale digital-first startups backed by large global firms. Recently, Ryan was recruited to be Head of Growth for Direct-to-Consumer at Constellation Brands Inc. This is a new venture under CBI that will be built on the foundation of a recent acquisition: CBI acquired a digitally-native DTC wine brand, Empathy Wines, founded by – you guessed it – Gary V. (More here). 

Yes, you got it, this is the type of job that doesn’t get posted, that you can’t apply to. A job that one can only hope to hear about through connections and through an endorsement that carries weight. It’s one of the reasons that I want an MBA from Stern, and here it is – this guy is doing it before he even graduates! 

After Ryan told me he worked directly with Gary Vaynerchuk, I must say I was intrigued. If you follow Gary on Linkedin or listen to his podcasts, you know that he is super passionate about everything he does. 

DK- Question, based on Gary’s aura on TV, does he take 2 Adderalls before every meeting or 4? 

***Let the record show that Mr. Mason was too smart to dignify this question with a response***

Fortunately for me, Ryan has been in my block and in most of my core classes since we both started at Stern in the Fall of 2019. He’s one of those people who you can tell is not just intelligent, but also keenly aware. I noticed in class that he speaks only when he needs to, not anytime time he wants to, and people definitely listen. That and he, along with our other group member Michelle, saved me in Operations Management from near guaranteed failure. Cycle times, Lamda, Little’s law- not my strongpoint. 

Mr. Mason is originally from NJ, currently lives in NYC, and went to University of Michigan for undergrad. Don’t you worry my fellow Sternies, if you went to Ohio State or Michigan State, Ryan is objective enough to still give you a shot, but will talk $hit on your team nonetheless. Respect.

DK- What are you most hopeful for (save a speedy, safe and effective vaccine)?

RM- First and foremost, that New York revives, that the city comes back to life. I want to continue to be here for a long time.  

DK- So New York is long-term play, yeah?

RM- Yes, New York, stay on the East Coast.  There are other places on the table, I could do LA, San Francisco, but ultimately I want to be in New York long-term. 

(I also would love to be in the Bay Area. Only problem is I just need another cool $3-5m to afford a place there.) 

DK- I remember when I was single, a particularly horrible first date. A girl tried to tell me that the Middle East was all jacked up because Obama invaded Iraq. I knew at that moment that I had to immediately get the bill, and we didn’t even order drinks yet. 

RM- Yes, there’s nothing quite like an intellectual turnoff. When you’re just like, this person just doesn’t… 

DK- (interrupting, due to uncontrollable excitement) There’s just so many of them now!? These nonstarters –  do you only get your news from one place? Are you Anti-Vax? Are you Anti-Mask? It feels like basic questions like this can filter out 60% of the population outright?

RM- Oh for sure. If we are talking elimination factors, for me, you have to be at least somewhat liberal or moderate, conservative is also ok, but a 100% subscription to the “Trumper, anti-mask, conspiracy theory” thing, just no. There has to be a certain amount of critical thinking, with empathy for other people, where you put yourself in their shoes. That’s foundational for me. Someone who wants to learn and thinks about how their decisions affect others. 

(If more people thought this way, how much better could the world be? Ryan Mason for Stern Singles or Ryan Mason 2020?) 

DK- Shifting gears a bit, what are you most scared of?

RM- I would say I’m most scared of not being fulfilled at the end of the day. I want my life to be fulfilled, I want to know that, I want to be aware of it. I want to be happy with a potential partner, but also continue to pursue that happiness, together. 

(A question about fear transforming into chasing happiness communally? Who is this guy, Lancelot?) 

DK – I remember in college, I was taking Arabic, and the professor asked:  “ما هو أكبر قرار في حياتك؟” , which means: “What’s the biggest decision in your life?”

At that time, I couldn’t hold myself to reply in Arabic, I just blurted out in English: “By far, whoever the woman I choose to marry will be the biggest decision in my life”. And the professor just stopped. She paused and realized that I was being authentic, and I kind of blushed because I had a huge crush on her. The professor also realized this, and cordially mentioned that she was married to an Isreali pro basketball player and that I didn’t have a chance. What is the biggest decision for you? 

RM- Your answer to that question is absolutely true, I think it’s the most important decision in anyone’s life.  It can affect every other facet of your life- how you grow, what you do, what your values are, how you raise a family- all that really needs to line up. 

And there you have it my friends. Ryan Mason, the colleague you want at work, the student who saves you at school, the somehow single man who you can bring to meet both the family and the crew. Did I mention he’s 6’2?

If you would like to nominate a classmate for future features of the Stern Spotlight, please email the Oppy staff at

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