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Thank you Paul and Jessica for taking a chance on us — we wouldn’t be here without you and YC :)

And thank you HN — I’m pretty sure the upvotes on the original screencast helped us get into YC and on Paul & Jessica’s radar to begin with!

Even you BrandonM — https://news.ycombinator.com/item?id=9224 — my favorite HN comment thread of all time :)




It's funny how often that comment—which I made as a 22-year-old undergrad—resurfaces. Someone even reached out to me 2 weeks ago because they wanted to use it in an article as an example of "the disconnect between the way users and engineers see software"!

I like to think that I've gained a lot of perspective over the last 11 years; it's pretty clear to me that point #1 was short-sighted and exhibited a lot of tunnel vision. Looking back, though, I still think that thread was a reasonable exchange. My 2nd and 3rd points were fair, and I conceded much of point 1 to you after your reply (which was very high quality).

Obviously, we have the benefit of hindsight now in seeing how well you were able to execute. Kudos on that!

Congrats on your success! I wish you nothing but the best going forward!


Well put.

Also, one thing I think people ignore is that BrandonM's comment was notable because it was voted to the top.

Which means that the people reading and voting on the thread, at the time, thought it was the best reply. But no one will ever point a finger at them, because they're anonymous. They also have less chance for self-reflection - who remembers an upvote?


I also think people might overlook BrandonM's follow-up reply to dhouston's reply on April 6th - "All of your feedback was well-thought-out and appreciated; I only hope that I was able to give you a sneak preview of some of the potential criticisms you may receive. Best of luck to you!"


Yup. It's really only the first part of the comment which had tunnel vision.

(Which does of course raise the question: were people upvoting for that part, or despite it? We'll never know)


I think the biggest issue with people is a lack of introspection, and this example shows the issue here. Most interactions are too meaningless and therefore difficult to self improve on.

I don't know what's the best system to make people reconsider their actions, however. After all, giving a single upvote and walking away is incredibly easy. Coming back to recognize your mistakes is hard.


I think people are always looking for a take on a new product that can be shown with 20-20 hindsight to be proven wrong...

" No wireless. Less space than a nomad. Lame." for the original iPod, springs to mind.


I hereby point a finger at the people who silently upvoted that comment


I think your feelings were shared by hundreds of professional investors that passed them up so dont be too hard on your 22yo self at the time. :)


I see you getting some flak here but for what it's worth, I read it as a very grounded discussion and feedback. I appreciate the fact that you conceded the points that seemed reasonable post Drew's comment.


To be honest I like seeing some posts like that where the entire concept of the idea is being challenged from the ground up, especially if the creator has to step in and defend it. Oftentimes I get more perspective into a product from the defense of its perceived shortcomings than I do from any marketing material.


3rd point (viral): The dropbox solution was great, of users getting more dropbox when they brought in another user. By rewarding with more dropbox (instead of money), only people who genuinely value dropbox would spread it. These aligned interests can't be gamed.

I thought dropbox was a great idea from the very beginning... but I've been repeatedly amazed at the scale of the opportunity. People working cross-mobile/desktop must be a big part of it.


> but I've been repeatedly amazed at the scale of the opportunity. People working cross-mobile/desktop must be a big part of it.

Or just multiple computers. Also don't forget file sharing and collaboration.

I'm a long-time Dropbox user, and my first use cases were, in order:

- shared folders with friends at university, when we were working on projects together

- shared folder for myself between personal computer and a station at work

Nowadays I use it mostly as a way to sync up my time/task tracking (in Emacs/org-mode) between multiple machines and mobile devices.

OTOH, my SO regularly uses Dropbox at work to exchange bundles of 200+MB files with other companies, and it's telling - there really is no better, safer solution for a regular user to send someone larger files when they no longer fit in an e-mail.


Your comment was one of a handful that lead to me registering for an account on HN instead of just lurking, I love that this got closure in my mind. Thank you for responding to this


That bit about closure made me smile. You're welcome :). I owe a huge thank you to the HN member who emailed me to let me know about this discussion.


I think your initial comment, your reply - and now this all say the same thing.

You seem like a great person & I wish you well with your own projects.


That's very kind, thanks!


Your original HN comment perfectly captures the quintessential HN user at the time. I feel like every “Show HN” thread has those types of responses of like trivially explaining away all the hard work with just a few “simple” hacks.

I think the typical HN user has morphed a bit at this point(re: crypto) but it’s great to be able to reference the totally aloof engineer that existed at that time.


I came to Hacker News through Paul Graham's essays. I learned about Paul Graham because we used ANSI Common Lisp in an elective Common Lisp class. His essays were specifically suggesting that many college-aged techies would benefit from starting a startup instead of going into the traditional workplace.

I bet that describes a lot of the early HN (originally: Startup News) users. I don't think it was really "totally aloof engineers", but instead young geeks without much perspective on the world. Most of us weren't even engineers at that point, by any reasonable definition of the term.


This may be the most civil discussion I've ever seen on the web. Spread out over 11 years! Amazing. I love HN.


It seems funny now looking at retrospective that neither Drew or Brandon said anything about syncing on Mobile. Congrats Dropbox!


Mobile was barely a thing then. Amazing the decade of progress in personal electronics.


I just looked it up -- The first iPhone was officially released 3 days after Dropbox received their YC check (June 29th, 2007 vs. June 26th). Astounding.


Drew and Brandon, together again!


Feels like the “I’m a Mac, I’m a pc” ad.


What do you do now Brandon ? edit: nvm, found this https://news.ycombinator.com/user?id=BrandonM


I also spent about 2 years working remotely and traveling with my wife, living in different places in Europe, Asia, and the US for anywhere from a few days to a few months. We have a travel blog and twitter account (all thanks to my wife) that I'm happy to share via email with anyone who's interested.


I'd love to follow along - my beautiful wife and I are planning to hit the road as remote workers, so always keen to learn from others who have done it as couples / families.



I think you were still very right in your intentions. I despise Dropbox, personally, and wish it would die. This is what Operating Systems are for.

However, the fact it has not died and is in fact 'a success' from the capitalist side of things, means what I think about filesharing being an OS service, doesn't really matter. Microsoft and Apple and all the other vendors are asleep at the wheel - but it has to be said that its just a distro upgrade away from being the end of Dropbox for a lot of people.


Funny to see how many "analysts" laugh at Brandon without even realising that their "analysis" use to be very flawed.


Love that Drew posted this from the stock exchange floor this morning


Here's a link to the actual presentation https://web.archive.org/web/20100817162301/http://dl-web.dro...


That web interface is soooooo much easier to understand and use. Makes me sad how unnecessarily complex modern UI is, not just on dropbox, but across the whole web.


Hell, even the menu bar UI on OS X is still terrible; they 'broke' it maybe 5 years ago and it's been the same mess ever since. It used to tell you what % of your dropbox was used, it used to tell you syncing status, it used to tell you all kinds of things. Now it's some weird changelog that looks nothing like anything else in OS X (or Windows, for that matter) from a UX perspective.

I mean, I guess I'm glad they didn't pull a Google and break it in new and exciting ways every 6 months, but really, it should have been changed back a week after they screwed it up.

Big congrats to the Dropbox team, though -- I use their product personally because it Just Works. Interviewed there back in 2011 when the office was (next to?) the old Fry's in Palo Alto.


It still does tell you those things (they've just moved around a bit).

The % used is seen when you click on the settings. I think because, honestly, they're trying to abstract the idea that you need to do that (the average user just cares that it works not the %).

Get where you're coming from tho - it's not the most clear or clean UI.


A "power user" toggle in most apps would be great. PayPal's site kinda does this with a "classic mode" toggle.


The response when he shared the file on his messenger was "why are you sending me this crap" :)) so funny if this was part of the original presentation of what would become dropbox.


which presentation is it to whom? to get into ycombinator?!?!


Seems like BrandonM's quote comes up all the time, but Joel Spolsky wrote in 2008:

“Imagine all your devices—PCs, and soon Macs and mobile phones—working together to give you anywhere access to the information you care about.” Wait a minute. Something smells fishy here. Isn’t that exactly what Hailstorm [2001] was supposed to be? I smell an architecture astronaut.

And what is this Windows Live Mesh?

It’s a way to synchronize files.

Jeez, we’ve had that forever. When did the first sync web sites start coming out? 1999? There were a million versions. xdrive, mydrive, idrive, youdrive, wealldrive for ice cream. Nobody cared then and nobody cares now, because synchronizing files is just not a killer application. I’m sorry. It seems like it should be. But it’s not.

https://www.joelonsoftware.com/2008/05/01/architecture-astro...

Has he made any public comment on synchronizing files / killer app in the intervening years?


Congratulations to the entire team.

I think it's interesting to go back to that thread, look at what the author (BrandonM) has done since then and learn some important lessons about being able to step outside of your own head to see the bigger picture.

Looks like he's still working for another company and has an unfinished blog (http://shebang.brandonmintern.com) but he seems like a really smart guy. The takeaway I got from the thread is "Don't be afraid to try something and finish it".

You guys had a lot of courage and perseverance to take an idea that people trivialized, have a working implementation, build a company around it and then IPO.


Looking at his LinkedIn profile, it seems like he was still in college then. He was wrong, of course, but I think his errors were pretty reasonable given his situation.

It's very easy for tech people to say, "But it's totally easy, you just [long string of steps that they've learned over the course of years]." It takes time to learn that no, easy things for you can be hard for others. If you want them to use the thing, you have to make it dead easy. I note that Apple made a shit-ton of money because so many tech companies (e.g., MP3 player makers) refused to really learn this lesson.

His second point, that USB sticks were still necessary, wasn't bad, just not forward-looking enough. He wrote it before the introduction of the iPhone, after all. But back then, high-quality connectivity was much less common. Then, Dropbox would have worked better for some than others.

And his third point was correct. Charging cash money is important.

So really, it's not a bad comment for a CS student. And it reminds me that I'm very thankful that most of my youthful opinion-spouting happened in offline and pre-web contexts.


Thanks for such a fair evaluation! That's honestly the first time someone has put my comment in context like that... I appreciate it :)


Hah! Very welcome.

The people we really should be raking over the coals are the VCs who didn't invest. Spotting good products is their job.


As an engineer, "But it's totally easy, you just..." is my least favorite phrase. "Just" in particular. You can obscure so much effort with 4 simple letters.


well you can't be too hard on Brandon

if every Brandon out there was able to see the big picture, Dropbox would have had A LOT more competition, when Dropbox was still in the early stages. It would have made it a lot harder for Dropbox to succeed, right?

So in a way, the fact that the millions of Brandon's out there who think curlftpfs is the best, and are not capable of seeing the true value of Dropbox--perhaps that was a positive thing for Dropbox, right? Otherwise they might have tried to make a similar product and competed with you years ago :)


Congrats Drew and Arash, amazing job! I still remember meeting you at Startup school and wear account #27 with pride :).


Next up AirBnb and perhaps Stripe (speculation). Those early YC investments are really paying off huge returns.

Unlike investing in the stock market, where you want to hit lots of singles, angel/startup investing is all about hitting home runs as the vast majority of the time you are going to strikeout.


It's too bad the original screencast page is gone: http://www.getdropbox.com/u/2/screencast.html

Edit: someone posted an archived link: https://web.archive.org/web/20100817162301/http://dl-web.dro...


Congrats Drew!

One of the highlights of my MIT experience was going to your ~yearly tech talks that you did at the beginning of the fall semester. I’m excited to see Dropbox continue to grow as a company. :)


I think you handled BrandonM's critiques pretty well, and not immediately getting defensive around the products shortcomings was well played. Congrats to you and your team.


Congrats Drew. I remember seeing the TechCrunch 40 pitch and writing about you guys. You inspired me to do YC myself. Congrats on the IPO my friend.


What a classic and inspiring YC story :) Big congrats!


As they say, don't listen to the naysayers... and you did not! Congrats.


On point 1, he failed to understand that 99.9% of population is not IT savvy, not to mention how much time such setup would take and then maintain to run smoothly with all security patches, etc.

2. He misunderstood initial description of Drop; that the files will reside locally even if you lose internet connection you still can access those.

3. He was wrong about "viral" but right about inability to "make money off of this" :)

Congrats on listing!




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