Why Aston Motes, Dropbox’s First Employee, Chose MIT Over Caltech

Aston Motes, currently chief software architect at Merchbar, on diversity in Silicon Valley: “the pipeline is kind of up to the gatekeepers”

Why Aston Motes, Dropbox’s First Employee, Chose MIT Over Caltech
Aston Motes, engineer at Dropbox [Photo: David Paul Morris, Bloomberg via Getty Images]

Aston Motes is probably best known for being Dropbox‘s first employee, helping founders Drew Houston and Arash Ferdowsi build the former Y Combinator startup into the highly popular file hosting site it is today.


After four-and-a-half years at the company, Motes departed on good terms to found his own startup at Y Combinator called Assorted Bits, a project he describes as “a much worse idea than maybe it felt to me at the time,” but that he continues to work on when he has the time. Still, letting go of Assorted Bits freed Motes to bring technology to his greatest passion, music–and for the last two years, he’s worked as the chief software architect for Merchbar, a startup that connects music fans with the hard-to-find merchandise of their favorite artists.

We spoke with Motes about the path that brought him to Silicon Valley and how opportunities for diversity have been taken and missed by the institutions around him. The following transcript has been edited.

On His Path To Computer Science

I always had computers around me and that’s due to my dad, who I think earlier than most people not in Silicon Valley realized the power of personal computation. So, by the time I could remember anything, my dad had something he was showing me on the computer. I didn’t understand it to be anything special at the time, but in looking back I realized that most people probably didn’t have somebody in their family who understood what a database was in the early ’90s. His interest rubbed off on me a little bit.

The moment, though, where I put myself on this path of being a software engineer was probably in middle school–and I just so happened to have cool friends who, for whatever reason, thought making web pages was cool. By the time I was halfway through high school, I was fairly certain that I was going to try to be a software engineer. I even went out of my way to take the AP Computer Science exam, even though my school didn’t offer it, because it just felt like the right thing to do as a future computer scientist or a future computer engineer.

The reality was, when I was in high school, I didn’t know anybody who worked at Microsoft or Google, black or not black. But I just assumed that I could maybe be one of those people. And certainly, getting into the colleges I got into gave me some confidence that at least I was smart enough to do that and then I’ll figure out the rest.

On Choosing The Right College

When I was looking for colleges, I went out of my way to look for [diversity]. And the two colleges I was looking at most seriously had a really big line in the middle. One of them was Caltech and one of them was MIT.


When I talk[ed] to people at Caltech about how they thought about race, how they thought about diversity, how they thought about culture, the answer I got back was: Caltech’s a meritocracy. Everyone’s here because they’re smart enough to be here. And we really don’t see race, right?

When I went to MIT, the story was totally different. MIT does a lot of campus events and a tremendous amount of time I spent at MIT, when I was visiting, was with Latino student groups, with black student groups, with fraternities and sororities and student living groups that all had these pieces of culture that they really dug in on. And MIT lets you choose which of those communities you end up at and I just loved that. I love this idea that you could, just as a support network, have these people around who you felt like, culturally, you fit in with. And those cultures are not always race-based.

MIT had this sort of flipped idea from Caltech about what culture and diversity could do as an experience around learning engineering. So, I guess even then, I acknowledged this idea that the pipeline is kind of up to the gatekeepers.

On Diversity (And The Lack Thereof) In Silicon Valley

There’s, at this point, a lot of interest from all types of people, regardless of race or gender or background, to be a part of this technology world. So, there’s a lot of programs [in the Bay Area] that are great, that are trying to get kids interested earlier and going out to communities that don’t have as much access, which I love.

But I’ll say that one of the things about Silicon Valley that makes diversity, in general, tough is that the way that companies get built is primarily about building an organization that is easy for someone who has almost no experience running an organization to run. You’ll hear it from lots of parts of the Valley that one of the easiest ways to hire good people is to look around you and hire your friends or hire people who are very close to you in your network who you know lots about on a personal level, you know their skills and how they’ll work out. And the consequence of hiring folks that you know is that if your network isn’t diverse in and of itself, then you’ve already set yourself up for a non-diverse company.

And then the extension you’ll get from that, which maybe those same people would advocate, is that you want to avoid the amount of conflict in the company. You want to avoid the amount of bandwidth spent trying to negotiate communication issues and as such you should find people who, if they aren’t in your network, gel well. So, this idea of cultural fit. And that’s the same thing all over again. I worry that a lot of these bigger jobs in Silicon Valley come from these smaller companies in some form or fashion, [so] it does matter who those small companies are made up of.


Dropbox, I used to joke, was an equal opportunity company only because we just happened to get a super, super diverse early crew. And I don’t know if we went out and intentionally did it at all, but it just happened to be that by hiring a bunch of MIT engineers who we had had classes with, had worked with on projects, we got a very diverse group of people.

[And even though] we hired a very diverse group of people from a racial standpoint, we didn’t have any women. At all. And that was not intentional, but it just so happened that the female coders we knew were engaged in other activities and we were not successful in recruiting or pulling in anyone who was a woman. It meant that as Dropbox grew, it got harder and harder for the company to recruit women. It was a glaring missed opportunity for us that we started with so much diversity in some ways and we didn’t have it in other ways.

I think Dropbox now has a group of really strong female engineers and women in all sorts of other roles in the company. Every single piece of the organization is doing a ton better and this is all from the outside [perspective]. But it took a while to get there and maybe it’ll even take a while longer before other companies like Dropbox build that stuff up. My hope is that when people start companies now, they’ll be a little more careful about those early recruiting efforts and how you build a company. I think almost everyone will tell you that who you hire in the beginning makes a big difference for what you build, but it makes an even bigger difference for the people you attract and the types of things that you get to eventually do.

I think that it’s important to have visible examples of the types of things that are possible–and history does not have very many examples of black people or women or Eastern Asians running big, important companies in Silicon Valley. Again, there’s a time aspect to this. It can’t all happen overnight, but I’m extremely excited about the possibility of getting the names out of some folks who are doing big things who are underrepresented in this world. And they should be well known.

I wish that more people knew that there’s this path that black entrepreneurs can take that does involve Silicon Valley. And when people have successes, I hope that they will be more open about them.