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Ask HN: Review our webapp: AirDropper
55 points by jesselamb 2418 days ago | hide | past | web | 51 comments | favorite
Hi everyone! My co-founder and I just finished our second pass at our new app and we were hoping to get some feedback from the HN community.


AirDropper is a Dropbox companion app for requesting files from anyone with an email address. You just authorize your Dropbox account, make a request, and we put the file the person uploads into your Dropbox. Everything's secure in transit, we can handle larger files than most email services, and it's really easy for the person sending the file.

To provide some context, I started my own law firm this year, and I immediately ran into some friction in trying to securely get files from clients. Many clients were uncomfortable sending sensitive documents as email attachments. I walked a few clients through signing up with Dropbox and sharing a folder, but that caused a lot of back and forth with creating an account, setting sharing permissions, etc. I talked through the issue with my perennial side-project partner and AirDropper is what we came up with as a solution. We made a "two week" version a little while ago and we got some great feedback, especially from designer friends who need to get files from clients that are too big to email. Today's version incorporates their feedback, along with some improvements we've stumbled into along the way.

What do you think?

Slick. I can see myself using this frequently.

I have a couple questions/comments:

- It's not exactly "secure", right? AirDropper has access to my file while it's "in transit" so AirDropper's really only "secure" if I trust AirDropper. You could, for example, be keeping a copy of everyone's files. So who are you, and why should I trust you?

- When I linked my Dropbox account I just gave you full access to my whole Dropbox. Ugh. Is there a way you can just get access to the directory in question?

These seem like obvious new user questions so you might want to add an FAQ, perhaps.

I understand the concern. All traffic from your computer to AirDropper and from AirDropper to Dropbox is SSLed. We actually don't have full access to your Dropbox account, just a sandboxed folder we create called AirDropper. We don't plan on expanding beyond sandbox access. We don't keep any copies of files you send or receive, though we do technically have access to them as long as their stored in the AirDropper folder in your Dropbox. You can deauthorize the app anytime on Dropbox.com.

As far as who's behind AirDropper, my name is Jesse Lamb and my co-founder is Nick Stamas. I'm a Florida attorney that works with tech companies on business formations, contracts, and intellectual property. I also blog at http://www.notmylawyer.com, which has been on the front page of HN a few times. Nick is a designer/developer who just moved to NYC. We've known each other our whole lives and we've been on various teams together for the past 6 years. The name of our company is Gruntverk, LLC. We don't have a site for the company yet, but our information is on file with Florida's Division of Corporations.

A FAQ is a great idea, and I really appreciate you bringing these issues up.


Thanks a bunch, Jesse -- I really appreciate you taking the time to answer in such detail!

Like I said, it's slick app and I totally see myself using it, so this is just icing on the cake.

Of course! Your feedback is gold. Thank you so much for it.

I would like to see these questions answered as well before I use the service.

However, apart from the privacy/security concerns I can see this service having a lot of potential.

Thanks! Let me know if my response to jacobian covers all your questions.

IIRC, you can make self-extracting password-protected encrypted archives. That solves the security question.

Great point. Yeah, just like with Dropbox you can always bring your own file-level encryption.

I think this is a great idea for me- I work technical support and often have to get large files from customers/ partners who do not have the ability to send them in a secure manner. Also I work on about 4 different computers during the day and it is helpful that it stores into Dropbox by default so that I automatically get the file on each computer that I have that account on. If worried about the secureness of your Dropbox, you can create a free new account that only stores your airdropper folder and share that folder with your primary account. That way no email addy or Dropbox is exposed, only the info. As stated already, if you encrypt the info, there should be little exposure. It is not necessary for everyone, but for someone like me who has to get files securely very often from folks with restricted firewalls, it seems a great solution. The file size would be the only limitation that might require me to find another method- sometimes even 50 MB isn't big enough which is I assume what you've said you have tested up to.

I went directly to your site from the link, without reading your post in its entirety and couldn't see the use of this until I read your post and the comments...

I think you need to take the time to explain who would use this and why on your front page a lot better from the beginning. I also don't think the diagrams are descriptive enough, for example I didn't really understand how exactly steps 2 and 3 worked until I read your post in detail.

So in closing ... market this more explicitly to devs/graphic designers/lawyers etc (folks who need to get files from non-technical people) and do a better job of explaining exactly how the product works and it could turn into a nice stream of passive income.

PS: An idea would be to allow your subscribers brand the upload page with their logo and colors then use their domain/subdomain names for it. This would make their clients even more comfortable with uploading sensitive information.

Looks good. I like diagram on the front page explaining things, but change the font for the text. It looks a bit sloppy. Also increase the font size a bit to optimize the size for the boxes.

One thing I don't see is a price list. How do you plan on making a business out of this? Monthly subscription on top of dropbox?

Thanks for the feedback. We haven't built the billing piece yet, but we're planning a freemium model based on number of requests per week.

Thanks for the clickable link.

Couldn't this work without dropbox? You're limiting your set of potential customers by mandating they use dropbox. You're also missing out on some easy cash for hosting that users would be happy to spend if it meant easy access to files they need. If I can hook up my dropbox... Fine. But if I can access an organized online directory of requested files, by client, date, size, and any parameters I entered at time of request... That'd be pretty sweet. You might be able to take cash that would otherwise go to dropbox.

That's true, there might be opportunities beyond just supplementing Dropbox's service. Thanks!

Seems like a good, although niche, idea.

Out of curiosity - were the files you needed from clients PDFs that required signatures? That seems to be the primary use case. There are some interesting startups around this area, but I haven't seen someone nail it 100% yet.

Yeah, sometimes it's signed documents but I also get client materials that are particularly sensitive.

I've been thinking through the signed documents problem, but I'm not sure the market is ready yet. We've had legislation in the U.S. that legitimizing electronic signature for about a decade, but there's a comfort to a signed physical copy that is hard for people to give up for big contracts. I'm wondering what user affordance will finally break through that mental barrier, but I haven't come up with anything yet.

Looks really nice, but as helpful as the four-paned image is, I think it would be really useful if you had a link somewhere to a (semi-)technical overview of what's actually going on.

Like a page of screenshots of the actual service UI and some details as to how everything is set up (for example, I initially thought that the uploader would also need a dropbox acount. After looking again, I'm pretty sure that's not the case).

It just seems rather jarring that the only thing you can do from the home page is give airdropper access to your dropbox.

That said, it looks like an awesome service; I'm sure I'll be using it.

Great idea. Yeah, we definitely need to make more obvious that the sender doesn't need a Dropbox account. That's a big value point.

Sceenshots and maybe a screencast is a great idea. I think we'll start with a FAQ since the implementation cost is so much cheaper and go from there.

Thanks for the feedback!

I genuinely wish you the best, but this does not seem to solve any problem that I can see.

If I want a file from someone, the easiest thing is for me to email him and say "send me file X" and he will reply with file X attached.

If he's hesitant to send file X because it contains sensitive information, he can encrypt it first.

If the file is sensitive, I have to decide whether I trust the person asking for it, but assuming I do, I also have to decide if I trust AirDropper and Dropbox? If I don't, then I encrypt the file anyway, at which point I might as well just email it directly.

You make a fair point. I'd say though, putting the important issue of trust aside for a second, it's not that we don't solve any problem, but that we solve a problem for which there are already other solutions. And in practice those solutions have disadvantages.

Taking file encryption as an example, you can certainly encrypt a file before sending it, but that depends on the sophistication of the sender. They may not be familiar with how to encrypt a file. And if they are, it's kind of a hassle dealing with encrypted files on both ends. You have to transmit the password in some separate medium from the file itself, and now you have to decide whether to keep both the encrypted and unencrypted versions. It's friction that our solution obviates.

Likewise, you can send an email attachment for non-sensitive files, but every email provider has differing file size caps. We're still testing the limits of our service, but we've already successfully handled files more than double Gmail's size caps, which are among the highest in the industry. Right now most of the alternatives to attachments require a fair amount of setup for the sender. Ours just requires they visit a page and upload the file.

Coming back to the issue of trust, that's definitely going to be a challenge for us as a company just starting out. If you have any ideas about how we can develop that trust I'd welcome them.

Thanks for the awesome feedback. :)

this is superficial, but that font looks terrible, at least on my screen. honestly, it looks like an amateur's first attempt at making a font. otherwise it's a cool product idea :)

Nothing is superficial, we always appreciate feedback. Can you tell me what browser you're using? Most of the site is set in Goudy Bookletter 1911, by The League of Moveable Type. Is this what it looks like in your browser? http://bit.ly/2oH1TM

Same problem for me:


Firefox 3.6.8, Windows 7.

Otherwise, great design and idea.

Thanks, we're looking into it.

Do you mind sending me a screenshot at inquiries@gruntverk.com ? You're not the first to comment on the typeface. Just trying to see if we're failing on taste or tech. :)


notice how the r and l characters seem to be a bit higher, and (at least in my opinion) the b and o chars seems to be too "fat", especially relative to the e. also, the bottom part of the a looks too thick...just overall looks a bit weird, definitely not like what nickstamas posted above.

this is in FF 3.6.8 on XP with cleartype enabled, btw.

Holy crap, that looks horrible! We'll work on it. Thank you so much for the screenshot.

More like a minor point, but I'd like to see that envelope more white-ish, the home page is really beautiful but the envelope takes a little eye-candy from it. :)

Good luck with your project!

I actually gave my dropbox username/password to someone just hours ago to login to my dropbox and upload a couple large files. This is definitely a better way. Thanks!

My father, an accountant, was talking to me about this very problem a few weeks ago, and I thought it was a good business opportunity. Congrats on taking a shot at it.

One question: Have you given any consideration for sending files the other way - in other words, from you to a less-sophisticated client? That's the other side of this equation.

We're definitely considering that once we're satisfied with how the current flow works.

Would it be possible to get a unique url so that I don't have to send an email ? (ex : if I want to send it by GTalk)

Yep, there is a checkbox on the form that allows you to skip sending the email. Instead, on the confirmation page, you'll be given a unique URL and a password that you can send however you'd like.

Oh I see. It's work but you have a bug and one or two minor "irritant" :

- If I check the checkbox, I have to input a valid email or I get a something went wrong error. (bug) - The person received an email even if the checkbox was checked (bug) - I have to input a description of the file requested (not needed)

Thanks, you found our first production bug! Should be fixed now :)

We still will require the file description, because in our opinion, the page that allows someone to upload the file should have some sort of reminder as to what file they are supposed to be uploading is (even if it is very brief).

One feature that seems to be missing is allowing recipients (uploaders) to send multiple files.

Currently, uploaders can't use the same request link twice so the requester would need to send 3 requests if they wanted 3 files.

It seems like the solution might be to have a "send another file" link, after the uploader has chosen their first file.

All in all, really slick tool.


Yeah, we need to work on implementing multiple file support really soon. I like the idea of a "send another file" link. Maybe add an "allow multiple files" option to the request form. I'll see if I can convince my co-founder, he's stingy with form elements. :)


Just from visiting the site I did not understand what "requesting" is. Would I browse some other dropbox user's filelist and ask him to send me one of the files? Reading above it rather sounds like "Provide a place for someone to upload a file and then find it in your dropbox".

I see what you mean. The vocabulary has been tricky for us so far. We'll keep working on it. Thanks!

Really slick UI and wonderful idea. But I think you are filling a hole in Dropbox.

Thanks. Yeah, we are definitely filling a gap, the same way a Twitter client supplements the Twitter platform or an email program supplements the email protocol. Dropbox has strong potential as a platform player over the next couple of years. It's the best cloud storage system there is, and we're hoping apps like ours and the efforts Dropbox is putting into mobile will make it more useful to more people.

I think the meaning was your service becomes obsolete once Dropbox decides to implement a similar function.

(Nice idea by the way.)

That's certainly a risk, but it seems like a lot of Dropbox's resources are going into mobile, at least for the time being. We'll see though.

It seems like you will put a lot of bike messengers out of work!

Ha, thanks! Yeah, we're hoping to expand so that you can send files too, but we haven't finished thinking through how we can improve that workflow.

very nice idea and execution.

might want to make it clearer that the person you're trying to get the file from doesn't need a dropbox account, as that seems to be the big idea behind this.

good point, we'll try to make that more obvious. Thanks!

Tried this out, very nice seemless integration with my dropbox


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