An Angel Investor

A Pair of Shoes

A while back, I emailed my husband Tim an article about the Sony email hack. It was about the child of a Sony executive who – the email exchange suggested – was given favorable status as an applicant to Brown University due to her influential, wealthy family. I was outraged.

Tim’s response came in the form of a Gchat: re: the gawker article about rich ivy leaguers… that may be an interesting small answers…since that happened for me

What followed was an intense, occasionally contentious, and ultimately not-fully-resolved discussion between us about privilege, guilt, and personal responsibility. This interview has been edited and condensed, and “Paul” is a pseudonym.


Where did you go to college?

Brown University, in Rhode Island.

Why did you want to go there?

I didn’t; I didn’t want to go anywhere. While I was visiting colleges with my dad, my mom was dying of breast cancer. She’d been sick for years, but this was the end. It was a shitty time.

We went and saw a bunch of colleges in the Northeast. I just remember feeling at every campus we went to, “This is not a place for me.” I reacted negatively to everything, and the least negatively to Brown.

Is that how you decided to go?

When we got back from the college tour, my dad asked me my opinion. I said that I didn’t know where I wanted to go, and he said, “I think you should go to Brown,” and I basically didn’t want to think about it and said, “OK.”

That was spring of my junior year, and my mom died a month or two later.

Tell me about Paul.

I met Paul right after my mom died. He was a very, very, very wealthy man who was a major figure in the community where I grew up, and it was known that he was interested in helping kids attend college.

Why the interest in you – and in helping kids go to college?

He had lost a parent when he was young, and he took an interest in mentoring and befriending high school boys in a grandfatherly way. It’s hard to talk about without making it sound weird, but it wasn’t. He became a close friend, not just of mine, but also of my dad’s, my brother’s, and a bunch of other kids my age.

How did you two get to know each other? Was financial assistance for college explicitly discussed?

Over the course of the year Paul invited my dad, my brother, and me to events where we got to know each other better – stuff like NASCAR races and football games and things I have to admit I didn’t have much interest in. But, I did really enjoy getting to know him. We’d talk about what I wanted to do with my life. He was, and is, a great person.

Did Paul have a specific vision for your future?

He definitely believed in being a decision maker, regardless of your field.

I remember one conversation where I met him at his office and he grilled me about my ambitions. It didn’t go well because my ambitions were small – I wanted to be a programmer. He said, “You don’t actually want to be a programming gnome for the rest of your life.”

He was blunt and didn’t pull punches. To him, being a programmer was not an end goal. His point was that I should go after something with more autonomy, value, and influence – making a broader, more interesting career. I was only thinking that I liked computers.

How did the discussion about his financial support of your education start?

I don’t remember the particulars. By the time I told him that I wanted to go to Brown, there was already some understanding that he would help pay for it. And he did. In fact, he paid my full tuition for all four years. I was very grateful for his generosity – but I didn’t understand the magnitude of it. People tried to tell me, but those sums of money were still abstract.

Did he help you during the application process in ways other than offering financial support?

After I told I told him I wanted to apply, he arranged for me to have some very atypical interviews with powerful alumni, including someone at the highest level of government who also wrote me a personal letter of recommendation. I also talked to several heads of the computer science department, and other people in positions of power at the university.

He also established a scholarship to give a full four-year ride to one student, every year, for a set number of years. He told me when he did that. I knew that meant that the university was likelier to accept me.


Was that uncomfortable?

I was aware of how extraordinary it was to be talking to these people simply because of my connection to Paul. I don’t remember going out of my way to be impressive, but I knew how to talk to adults.

Were you conflicted about the access you got as an applicant due to Paul’s influence and connections?

I was a little conflicted about the access I’d been granted, but not that much. It was a great opportunity and I wasn’t going to pass it up. I didn’t talk about it much with my friends because it was a fraught conversation – they disapproved of his role in my life.

Brown has a very low acceptance rate. Do you think you would have been a competitive applicant without Paul’s help?

I knew Brown was a competitive school and I was a solidly average applicant in terms of grades and SATs. I also was very seriously into computer science, did an independent study, wrote my own programs, and I am from a state where they didn’t get a ton of applicants, all of which perhaps would have helped set me apart. But there was nothing obvious about me to suggest I would be a shoo-in. No one is.

Also, Brown admissions were not need-blind at that point, and I would have needed financial aid.

What did your dad think about all this?

Having this kind of access obviously put me at an advantage. I remember talking to my dad and Paul about it and asking them if it was OK. Both of them said that the entire process was unfair, and didn’t want me to fall on my sword thinking that would change the system.

Were you surprised when you were accepted?

Actually yeah, I was surprised when I got in because it’s such a crapshoot, and I had applied early and been deferred to the regular (non-early) applicant pool.

I had plenty of privilege growing up – though nothing this extreme ever happened to me – and I definitely feel guilt about it. Like, why did I get what I did? It’s not right, and there’s no defensible reason for it. Do you have any guilt over all the advantages you were given that other kids applying didn’t have?

Honestly, I don’t. I’m extremely grateful for what Paul did for me, and any conflicts I have about it are minor. I also think it’s more important to acknowledge that the system rewards privilege than to feel guilty.

One, I think there is an inherent hypocrisy in saying you feel guilty about something that you would go back and do again (which I would).

Two, there’s a difference between feeling guilt on a systemic level and feeling guilt about a particular situation. Discomfort with the system is something I can address by trying to live honestly. What I mean is living in a way that acknowledges my privilege, and puts that privilege to reasonable use (not using it to undermine other people, for example).

The other thing is that what Paul did was an act of selflessness and generosity. He helped a lot of kids go to college, many of them with fewer advantages than I had. Saying I felt guilty would feel like a betrayal of what I was given.

Do you think guilt in a situation like this is pointless?

Somewhat. Guilt doesn’t accomplish anything, and I think people often use it to make themselves feel better about their privilege. There was a lot of good that came of what I was given – I feel like I’m a better person for having gone to Brown, and I hope that translates to me living a better life.

But isn’t there some sense of obligation to, as a privileged person, be a part of the solution to correct the broken systems of the world?

If I have privilege, am I obligated to correct that system imbalance? I don’t know. I’m a game developer, not a social activist, but I can participate by showing support for people who are enacting it. I don’t know if that’s good enough, but that is what I’m doing.

There are obviously a bunch of broken societal systems that favor some people dramatically over others. I think one of the most insidious elements of privilege is that people don’t like talking about it when they have it, which makes it invisible. Unexamined privilege seems like the most destructive kind.

Why are you choosing to talking about this?

Privilege is a discussion that we all need to have in order to have a more just society. That’s part of my motivation, but I’m not trying to absolve myself of anything. Privilege makes people uncomfortable to talk about when they’re on the benefiting side, but it should be talked about more – especially because it’s frequently invisible and unacknowledged.

If a Paul-figure were to come into your life again and offer to help your kids in the same way you were helped, would you be in favor of it?


Does it ever bother you that you don’t know if you would have gotten into Brown without Paul’s involvement?

I would be lying if I said it didn’t make me uncomfortable at all. Would I have gotten in on merit alone? There’s no way to know, but I’d feel like I owned it more.


Image: A Pair of Shoes, by Vincent Van Gogh (1886)


  1. Brett

    I’ve never really made a conscious distinction between systemic and personal guilt, or thought too deeply about what unacknowledged privilege can do. I really enjoyed and appreciated this!

    • leda

      There is a lot to think about with both kinds of privilege (and guilt). I too appreciated that Tim thought about his situation in terms of both. It gives you a lot to think about.

  2. Hi, if you think about it, nonprofits that assist children to get into college are also an unfair advantage. People are relationship oriented. So many jobs are qualifications plus someone’s help. I think the trick is to think of who has no access to those relationships and try to form them, to even things out. It is a tough one, though! Great topic, and thoughtfully discussed!

    • leda

      Agree that much of getting offered opportunities for advancement and education have to do with relationships. As you said, finding people who don’t have those relationships, and then building them, is key.

  3. This was an interesting discussion… I tend to grab whatever advantage comes my way. But I definitely feel guilty about it.

    My mom has a theory that there’s a lot of free-floating guilt in the world, and some of us just attract it =P

  4. Michael

    Interesting discussion indeed.
    The whole guilt thing throws me.

    The underlying unsaid assumption here is the John Wayne syndrome. We are all independent actors who should succeed or fail based on our own merits, gumption, efforts… The cowboy archetype. Getting help or relying on the group is a weakness.

    In reality the model that works best is “we are our brothers keepers” we help each other and we are all stronger for it.
    No man is an island…

    This is not to say that individual effort and accomplishment should not be recognized and measured – but not in isolation.

    Tim and Paul are an example of how the system should work. In fact the process of being able to reach out to a larger pool of potential students with a broader set of evaluation tools should be institutionalized.

    Tim should not give guilt a second thought. I hear him being grateful he was found and wanting to pay it forward.

    • leda

      Michael, thanks for your comment. I hear what you’re saying. Thanks for this thoughtful response. Like Tim, I’ve certainly been given many things – opportunities, gifts, leeway – acts of generosity that have meant a helped me and had a big impact.

  5. A very honest and penetrating interview. Navigating the game of life is such a crapshoot, such a maze, that it would be a waste to fall into guilt over something good but “unearned” coming your way. Yet, some feelings are unavoidable. I wince still at my awkward reference at your wedding to “don’t talk about the Porsche.” The verbal holes I have stepped into are always ready to help me feel bad. And that’s too bad.

    • leda

      Isn’t it, though? I can easily bring to mind half a dozen things I feel guilty about with almost no effort. I appreciate Tim’s point about the futility of guilt. I’d like to borrow a little bit of that. It’s so easy to come down hard on ourselves – almost always with more ferocity than we would on anyone else.

  6. CLARE

    Wow. I probably should read this again and not reply straight away, but the moment beckons… I find this a bit shocking. Because the emphasis seems to be about poor Tim, and how he ‘manages’ his guilt and that seems very self indulgent to me. Be guilty or not, who said that feeling comfortable all the time was part of the deal? So, you had an easy ride, and you feel a bit iffy about it, but not enough to really get upset about it, or work to change the system, or refuse any further offer of an easy ride. Frankly I find any sense of unease that you, (or someone in a similar situation), might feel, fairly low on the scale of importance. Basically it seems that people want to gain from the unfairness and injustice in the system, but to not lose too much sleep about it.
    To make the point that it is ‘all about relationships anyway’ is pretty disingenuous. The kind of relationships needed to get these kind of ‘special benefits’ come from generations of privilege…people who knew relatives and employers and friends stretching back for decades. A few ‘programs’ to mentor the disadvantaged is really tokenistic. It might help a few individuals, but it will never create a level playing field, or subsitute for the knid of relationships that helped you on your way.
    I do think it is valuable for advantage and privilege be acknowledged, though it is kind of acknowledged in a whisper whilst the ‘you can do anything you want if you put your mind to it’ rhetoric is shouted out from the rooftops with a megaphone. And those who don’t win, and don’t break through the curtain of privilege, are demonised for their personal failings rather than acknowledged as the necessary ‘filler’ that society requires. It’s a shockingly competitive game, only a handful can make it, and those handful get a leg up.
    You are basically saying ‘That’s the way of the world. I’d rather be a winner than a loser. And I haven’t taken on any responsibility to change the world’
    So why would I be interested in your story?

    • leda

      Clare, I understand why this story upsets you. It’s an extreme, extreme example of privilege that few people would ever dream of, let alone experience. The intent of the piece wasn’t to editorialize about Tim’s position or his feelings, but to tell an interesting story and have a conversation about privilege and personal responsibility. For me, the piece raises as many or more questions as it answers.

      Thanks for sharing your perspective. We always appreciate hearing from readers.

      • CLARE

        Actually, I wonder how extreme it actually is. I suspect it goes on all the time. and our (western democratic) ‘merit based’ system is largely a scam. The veil gets lifted from time to time when nepotistic behaviour on the part of politicians or other public officials is revealed and people are (mock) scandalised by their behaviour for a time, until the media cycle rolls on, with the next welfare cheat story or similar.
        You can’t separate the individual and society. You can’t say that my little rort here doesn’t matter, doesn’t perpetuate a society of injustice. The reality here is not about an individual’s generosity, or accepting a gift or being my brother’s keeper as someone said, but getting an unfair advantage in a system which is supposed to be merit based, and from which many many benefits flow to the individual who gains access. We may as well get rid of the entrance criteria and just let people get in based on recommendations, which is most likely the truth of the situation anyway.
        Accepting an unfair advantage makes life harder for those who don’t have access to that advantage. That’s the cold hard truth.

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