Talking with an Ivy Leaguer on Wall Street

Another memoirs of sorts, this time reflecting the Ivy League alumni I've been meeting in NYC, both in the startup community and on Wall Street.  I've been spending more time in NYC instead of SF for a change of location (and people), but ironically, I'm running into sort of the opposite situation to that I had in my short story, Talking with an Engineer in Silicon Valley.  Whereas many I met in Silicon Valley lacked empathy, considerateness, and other traits but at least wanted them (even if superficially), the circles I'm getting into in NYC seem to simply accept that these traits don't genuinely exist and are always superficial.  Maybe it's just my luck that I'm just somehow always meeting the most 1-dimensional people, but the frustrating part is they always start off seeming normal in the beginning.  As with my other short story, the conversations below are nearly cut-paste from my personal experience, besides obvious name changes and other details to keep individuals anonymous and the story somewhat coherent.  For those easily offended, this obviously doesn't reflect every person from Ivy League or in Wall Street and is just a likely biased, limited subset of the real world from my own experiences.

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Sam: Hi, I'm Sam.  Nice to meet you.
Ivy Leaguer: Hello there! Nice to meet you too.  Where are you from? What do you do?
Sam: Oh, I just moved here from San Francisco.  I'm mainly a freelancer, although I am considering starting my own company to focus on my tech and creative interests.  So I guess you could say entrepreneur sort of.  I just like making stuff.
Ivy Leaguer: Oh, how interesting! I'm also trying to start my own thing - probably creating technology too as that's what I'm passionate about.  We should chat more some time.  Perhaps I can help you with the finance side of your company.
Sam: Sure, I could use some help there.  Let's talk more some time.

* A week later *
Ivy Leaguer: I just want you to know that I don't normally meet people if they schedule less than a few weeks in advance, but today I made an exception.
Sam: Okay? ...
Ivy Leaguer: I graduated from Ivy League colleges like Harvard, Princeton... and worked at many other top investment firms like-
Sam: What experience do you have with starting a company?
Ivy Leaguer: Check out my backpack.
Sam: What about it?
Ivy Leaguer: The name...
Sam: Goldman Sachs?
Ivy Leaguer: You got it.
Sam: But have you actually started a company before?
Ivy Leaguer: I've worked at Goldman, JP Morgan, ...

* An hour later *
Sam: Yeah, but what specifically have you done? I don't care about the names.  You haven't told me why I should trust you to know what you're talking about.
Ivy Leaguer: I did say why.  I'm from Harvard and Princeton, and I worked at all the top firms...
Sam: Right, but so are thousands of other people.  Also, some fraud could just say he's from every top school and firm in the country.  How would I know you're not just making this up?
Ivy Leaguer: Because I'm from Harvard and Princeton.  Because I worked at Goldman Sachs, JP Morgan...
Sam: You're just repeating yourself.  That's circular logic.  It's like saying something is good because it's good.  Give me proof.  The next Madoff could say he's from Harvard, worked at Goldman, all these big names.  Would you think him trustworthy just based on that?
Ivy Leaguer: Well, I would if I didn't know he was a fraud.  He did everything right until then.  Many people got fooled.
Sam: That doesn't make it okay.

* Weeks later *
Sam: Alright, I guess you can help me with my company's finances.  I'm not entirely convinced, but everyone seems to say you're the best at this.
Ivy Leaguer: Great, you won't be disappointed!
Sam: I guess even if you're Madoff, at least the numbers will look right.
Ivy Leaguer: But I'm not Madoff!
Sam: I'm just kidding.  It was a joke.
Ivy Leaguer: Oh. You know, I can't tell when you're joking.  You don't raise your voice or anything.
Sam: Well, yeah, that's pathetic if you have to raise your voice to signal you're joking.  You should be able to just tell by context.
Ivy Leaguer: But no one else I know does that.
Sam: What? Everyone I know jokes by context.  How would you know something was sarcastic in text then?
Ivy Leaguer: That's why humor doesn't carry in text very well.
Sam: What about all the books you read that use humor? Are you only able to know it's sarcastic when they label it? Have you never read satire?
Ivy Leaguer: What's satire?
Sam: Uh, parody but in literature form I guess - you know, like from English class.
Ivy Leaguer: I never read any satire at my school when I took English.
Sam: Well it seems like they didn't teach everything they should have.
Ivy Leaguer: My school is one of the top-rated schools in the world.  We score among the highest no matter what metric you look at and send the most students to Ivy League colleges every year.  Almost all of the people who graduate from my school end up successful in the career.
Sam: What does that have to do with anything I just said?
Ivy Leaguer: Well you said my school didn't teach satire.
Sam: And it didn't.
Ivy Leaguer: But my school is top rated.  I had all As in my essays and 5s in my AP exams, and our school is known for being among the best in the country.
Sam: I never said it wasn't, but you yourself just said you were never exposed to satire.
Ivy Leaguer: I had straight As-
Sam: Yeah, I know you did. Can you stop saying that? All I'm saying is that despite all the rankings, they seemed to have omitted teaching you something.
Ivy Leaguer: They taught everything that was on the standard tests.  I got perfect scores.
Sam: The standard tests are the bare minimal of what a school needs to teach.
Ivy Leaguer: And there's no reason for them to teach more than that.
Sam: What do you mean there's no reason? They're teachers.  They're supposed to teach you as much as they can.
Ivy Leaguer: Why would they do that? They don't get paid that much.  Their only job is to get us into good colleges.
Sam: Um, there are plenty of teachers who teach because they genuinely want to help people.  That's why they became teachers.
Ivy Leaguer: I've never met one.  Every teacher I know was stuck there or wanted to become a professor at a college to make more money.
Sam: You should hope they don't end up becoming a professor if that's the reason.
Ivy Leaguer: Then what reason would they have?
Sam: I just told you... Because they genuinely want to teach.
Ivy Leaguer: And I just told you I've never met one.
Sam: You don't need to meet one to know they exist.  Use your imagination.  Is it that hard to imagine that someone could just genuinely want to teach and help people?
Ivy Leaguer: If I never met one, how would I know they exist? You can't just make stuff up.
Sam: I don't know... read a book? It's not that hard to come across examples of genuinely good people.
Ivy Leaguer: That's just fiction.  It's not real.

* Months later *
Sam: Thanks for coming by my studio to work on this.  I hope you don't mind that the place is a bit of a mess.
Ivy Leaguer: Wow, you have two pianos!
Sam: Yes, it's for two people to play at the same time.  Can you play?
Ivy Leaguer: Yes, I trained for 12 years, but I only played real pianos.  I'm not sure if I can play a digital one...
Sam: These are among the best digital pianos you can get; they're supposed to replicate the feel of a real piano with the hammer action and everything.  Why don't you give it a try?
Ivy Leaguer: I don't have any sheet music with me though.
Sam: Just play something random.
Ivy Leaguer: What should I play?
Sam: Whatever comes to mind.  Here, I'll just play the left hand in C; you can just hit any white note and it should sound fine.
Ivy Leaguer: I can't...
Sam: Just hit one...
Ivy Leaguer: Which one?
Sam: C?
Ivy Leaguer: What next?
Sam: Just hit random white notes.  Look, I'm just literally hitting random notes with my right hand.  It sounds fine.
Ivy Leaguer: Can you give me the sheet music for what you're playing?
Sam: What? There's no sheet music.  I'm just making it up.  It was literally just random notes.

* Later that day *
Sam: Ok I know you come from banking and all, but these numbers don't look quite right.  They don't add up.
Ivy Leaguer: Ok I just re-calculated them.  It's the same number.
Sam: Did you look into the actual line items though? Make sure they're in the right categories, etc?
Ivy Leaguer: No, do you want me to do that too?
Sam: Don't you think you should?
Ivy Leaguer: I'm just doing what you asked.
Sam: But do you understand why I asked?
Ivy Leaguer: No.
Sam: Don't you care why I asked?
Ivy Leaguer: No, because I don't need to know.  All the years I spent in school and at the top firms, I never needed to ask why.  You're actually encouraged not to.  It slows things down and gets in the way of productivity.
Sam: Whether the company lives or dies can depend on if you get these numbers right.  You should care.  We have a profit share agreement, but there's no profit to share if the company goes under.
Ivy Leaguer: I do care, but I don't see what the problem is.
Sam: What if I didn't ask you to double-check the numbers?
Ivy Leaguer: Then someone would have noticed when they were off later in the year.
Sam: After we already report them?
Ivy Leaguer: Yes.
Sam: You don't think that would destroy my company's credibility if we reported wrong numbers and had to backtrack a year of data?
Ivy Leaguer: It wouldn't be a year, maybe 6 months at most.
Sam: Same difference.  The company's credibility would go down the drain.
Ivy Leaguer: How would you know?
Sam: Well, what would you think if you saw a company back-adjust all its numbers because they misreported?
Ivy Leaguer: I don't know.  I've never seen it happen.
Sam: Alright, look, this isn't how things should go.  I need you to put in as much effort as I do here if we're going to be partners.
Ivy Leaguer: I *am* putting as much effort as you are.  I just crunched all the same numbers and wrote the same things.  I did everything you just did.
Sam: No, that's not... the work is in realizing you had to crunch those numbers in the first place.  Right now, you're just doing that because I told you to.
Ivy Leaguer: Yes, and that's how it should be.  I'm doing exactly what you're telling me to do.
Sam: I'm trying to get you to see why I'm asked you to double-check these numbers.  It's not helpful if you're just obeying orders.  You should understand what we're doing and why we're doing it.
Ivy Leaguer: I've worked at many firms much bigger than this.  We've never had to worry about why.
Sam: Don't you think that's bad?
Ivy Leaguer: It's not bad.  It's just not good.
Sam: What? Didn't you read 1984 in school?
Ivy Leaguer: Yes, it was my favorite book.
Sam: You basically just corrected me to say "not good" instead of "bad." That's like straight up conditioning from the book to never think negatively.
Ivy Leaguer: 1984 is fiction.  This is real life.

* Later that week *
Sam: Okay, don't take this the wrong way, but I think you might have low self-esteem.  I'm not saying it to insult you.  I mean that, quite literally, you don't seem to know if you're good or bad at something unless someone tells you, even if that person has no expertise whatsoever.
Ivy Leaguer: No, that's not true.  I know if I'm good or bad at something.  I just don't know how good unless someone tells me.
Sam: ... That just proves my point.  You say 1984 is your favorite book; yet you just basically said rephrased "good or bad" with "how good."
Ivy Leaguer: Well, how are you supposed to know how good you are unless you have something to compare against???
Sam: What? Just look at what you're doing and see if you can improve in any way.  It doesn't need to be compared.  What if you were the first to try something new?
Ivy Leaguer: You always have reference points.  If you are doing something new, you pull pieces from reference points that already work.  I saw how successful people were on Wall St, and they became my reference points for how I want to live my life.  You have mentors, role models...
Sam: Not necessarily.  Just look at my own background.  Neither of my parents ever supported me or believed in what I did.  I was the only person in my circles growing up to ever get into programming when people didn't even think it a worthwhile career yet.  I taught myself to trade in college when my professors and classmates even to this day don't even think it legitimate.  Where's my reference point?  If I only followed those around me, I'd just be another accountant or consultant.  I mean, just look at what I'm doing now - my own business.  No one else I know is doing this.  In fact, most startups fail.  I should be doing the opposite.  If I used reference points, I'd just be working 9-5 like everyone else.
Ivy Leaguer: Well, that's because your startup is actually a success.
Sam: Uh, only because I told you.  The only proof you have that I made one is my word.  How do you know I'm not lying or faking it?
Ivy Leaguer: Why would you do that?
Sam: What? People lie all the time.
Ivy Leaguer: Not in my circles.  People keep their word.
Sam: Well, it seems like even if they did lie, you wouldn't notice.
Ivy Leaguer: No, they're just good people.  We all come from top schools, top firms... it's curated, so we don't have to worry about things like this.
Sam: That's a bit scary, don't you think? You're just assuming based on their background.  Like I said, you wouldn't even know if it didn't hold up true because you never bothered to check.
Ivy Leaguer: Because I don't have to! I got where I am today, didn't I? It's working so far.
Sam: And what happens if things break? What if something happens that you don't expect or that you haven't been prepped for? You have like no defense at all against the unexpected.
Ivy Leaguer: Well, that's why it's unexpected.  It's unknown.  You're not supposed to see it coming.  You can't.  That's normal.  Most people can't see what's coming if it's really unexpected.  That's why it's unexpected.
Sam: Yeah, but you're not even trying to see what's coming.  And it doesn't make it okay even if most people are that way.  Normal doesn't mean it's okay.  Most people are poor, but it's not because they want to be there.
Ivy Leaguer: No, most people I know are successful.
Sam: That's in your small circle in the 1% of the world.
Ivy Leaguer: Well that's the only people I know.
Sam: Then consider yourself lucky? What if you grew up with the majority of the world who weren't successful? Would you be okay with just being poor and going nowhere with your life just because it was normal?
Ivy Leaguer: But I'm not.
Sam: Well, just take a step back.  What if you thought things were okay but they could be better? What if there's a life that could be far better than yours and you just didn't know about it, that compared to them, you might as well be poor and unsuccessful?
Ivy Leaguer: I'd have to see it first.
Sam: But you never leave your circle.  How would you ever see it?
Ivy Leaguer: If it's so good, I would hear from other people.
Sam: Other people in your 1% circle? If they're just like you, they probably never leave their circle either.  How would they know? It's like blind leading the blind.
Ivy Leaguer: Well... I never thought of that, but...

* Later that month *
Sam: This is cool.  I didn't know you play tennis as well.  We should have just had our first meeting here instead of at a coffee shop.
Ivy Leaguer: Just a heads up though, it's going to be $50/hr.
Sam: For what? Aren't these courts free?
Ivy Leaguer: I mean my rate.  I charge for lessons or practice sessions.
Sam: I didn't ask for lessons...
Ivy Leaguer: Well, why else would I play with you?
Sam: For fun? I thought since we both enjoyed tennis we'd just play casually.
Ivy Leaguer: I do enjoy tennis, but you're the one who wanted to play, not me.  I'll cut you slack this one time, but you're being disrespectful of my time.  This is time I could be charging to someone else.
Sam: I guess.
Ivy Leaguer: What are you doing?
Sam: What?
Ivy Leaguer: Aren't you going to open a new can of balls?
Sam: These are brand new.  I just opened them yesterday.
Ivy Leaguer: You have no etiquette.  You're supposed to bring a new can every game.
Sam: I don't see what the big deal is.  These are literally only a day old.
Ivy Leaguer: Well, I don't mind.  I'm just telling you so you know.  Other people might not be as tolerant.  You clearly are new here, and I'm just trying to help you.
Sam: Do you want to practice serves before we start?
Ivy Leaguer: Okay.
Sam practices on one side for a few minutes, then goes to the other.
Ivy Leaguer: What are you doing?
Sam: What?
Ivy Leaguer: Why did you come to my side?
Sam: To practice from the other side.
Ivy Leaguer: But no one does that.
Sam: So?
Ivy Leaguer: That's bad etiquette.
Sam: I don't see what the big deal is.
Ivy Leaguer: I'm telling you you're being rude.
Sam: Well I need to practice from both sides to warm up.  The sun's at an angle.  My serve is going to be different depending on the side of the court.
Ivy Leaguer: But you just don't do things like that.  Look, I'm just trying to help you because you're clearly new.  I don't mind, but other people might.
Sam: Again, I don't see what the big deal is.  I'm just going to hit a few from this side and that's all.  No harm done.
Ivy Leaguer: But no one does that.  It'd be like if I started hitting with both left and right hand.
Sam: What's wrong with being ambidextrous?
Ivy Leaguer: It's bad.  No one does it.  You're not supposed to play like that.
Sam: Well I do.

* Three months later *
Ivy Leaguer: Hi everyone.  I'm here with my business partner Sam.  I moved here from San Francisco.  I'm a freelancer and started my own company for tech and creative interests.  I am an entrepreneur, and I like making stuff.
Sam: Wait, what? Why did you just copy my intro?
Ivy Leaguer: I'm just keeping it consistent, so we have the same talking points.
Sam: But that's a personal intro.  You should be coming up with your own, not using mine.
Ivy Leaguer: But you already came up with one, and it works.
Sam: It works for me.  It doesn't work if you start using it... Don't you think that's kind of messed up to just copy someone else's?
Ivy Leaguer: No, we're a team.  Teams share.
Sam: But you just let me do all the work.
Ivy Leaguer: No, I also talked. I did just as much you did.  I said everything you would say.
Sam: The work is coming up with what to say... Besides, what would you do if they start asking about your freelancing and tech experiences?
Ivy Leaguer: I'll just say the things you normally say.
Sam: ... No wonder you haven't gotten any leads yet.
Ivy Leaguer: That's not my fault.  I'm using your words.

* One year later *
Ivy Leaguer: What?! You can code AND you know finance?
Sam: Yeah, what's the big deal?
Ivy Leaguer: Do you realize how much you're worth? You're - you're like a gold mine!
Sam: What?
Ivy Leaguer: Why aren't you working for some big tech company right now? You could be making so much! If there's one thing I can help you with, it's that you don't realize how much you're leaving on the table.
Sam: Uh, no I just don't want to work for another company.
Ivy Leaguer: Really? Why?
Sam: I just don't.  I don't want to be stuck in some 9-5 job.  I like what I'm doing right now.  I can create things and work on whatever I want.  Didn't you say you wanted to start your own company to create technology? It's the same feeling.
Ivy Leaguer: Yeah, but people just say that to fit in.  You don't *actually* want to create things.  That's just an image.  You tell people your passion is technology, but when you go home, you just want to live a normal family life.
Sam: Well, no.  I actually want to create things and not work in a 9-5 job.  It's not an image.  What I want to do and create isn't just something I tell people.  I actually am like that whether I'm at home or out with people.
Ivy Leaguer: Hm I guess.  Most people I know would kill to have what you have... Besides, if you work for someone else, then you don't have to worry about your company failing.  There's so much competition out there.  Eventually someone will do what you do, and your company will fail.
Sam: What? No it won't.  It's not like we're selling commodities or something.  We're not in that kind of business.  Our success is dependent on our own work only.  Not everything is zero sum.
Ivy Leaguer: Everything in life is zero sum.
Sam: That's not true at all.  Someone doesn't always have to lose for you to gain.  There are plenty of people smarter than you.  Do you lose sleep over that everyday?
Ivy Leaguer: Actually I do.  If I'm not the best at what I do, someone will probably replace me.
Sam: Replace you in what? You are your own person.  No one can ever take that away from you.  When you get married, are you going to constantly worry that your partner would leave you because someone better comes along?
Ivy Leaguer: Yes, otherwise why else would they stay with me?
Sam: ...
Ivy Leaguer: And don't say love!  That's an illusion. That's why most marriages fail.