Screaming in the Cloud - Making Dropping and Sharing Easy with Timo Josten

Episode Date: April 1, 2025

Dropping and sharing files should be easy. What a novel idea. On this episode, Corey speaks with Timo Josten, the sole developer behind Dropshare. We bring up the fact that he’s the only guy working on it because the tool is quite impressive! Corey loves it and so does an entire community of folks on Github! Together, they discuss the evolution and functionality of Dropshare. Timo also shares how he balance of enhancing Dropshare, emphasizing user feedback, and customization options, all while offering feature updates and maintaining sustainability. Show Highlights(0:00) Intro(1:06) The Duckbill Group sponsor read(1:39) What does Dropshare do? (6:10) Dropshare's impressive flexibility and dedicated community(10:27) How Timo landed on Dropshare's business model(12:38) What's new in Dropshare 6?(16:09) The Duckbill Group sponsor read(16:36) Determining what should be an update or part of the next version of Dropshare(18:30) Dropshare’s iOS app(21:04) The perks of being able to configure deletion in Dropshare(25:45) Dropshare's thriving GitHub community(29:26) Where you can find more from Timo and DropshareAbout Timo JostenTimo Josten is the developer of Dropshare, the macOS and iOS app to upload anything anywhere.LinksTimo’s LinkedIn profile: https://www.linkedin.com/in/timo-josten-493962185/Timo’s personal website: https://josten.ioDropshare: https://dropshare.app/shitposting.pictures SponsorThe Duckbill Group: duckbillgroup.com 

In my professional career, it's always a compromise between what the customers want, what the product is supposed to be, what the product managers imagine their product to be. But in this case, and that is why I enjoy to work on Dropshare so much, it's just me, right? The only one I need to argue with is me. And if I think it's a good idea and like the feature, I'm just going to implement it. Welcome to Screaming in the Cloud. I'm Corey Quinn. For those who may not be aware, I spend a lot of my time on the Internet shitposting.

I enjoy finding tools that make that a lot easier for me to do. And one that I've been using for years is Dropshare. Timo Joosten is the owner of Dropshare the company, which creates Dropshare the product that I've been using for a while and just released a new version. Timo, thank you for agreeing to talk to me. Hi, thank you for having me be here. Very glad. This episode is sponsored in part by my day job, the Duckbill Group. Do you have a horrifying AWS bill? That can mean a lot of things. Predicting what it's going to be, determining what it should be, negotiating your next long-term contract with AWS, or just figuring out why it increasingly resembles a phone number,

but nobody seems to quite know why that is. To learn more, visit DuckBillGroup.com. Remember, you can't duck the duck bill bill. And my CEO informs me that is absolutely not our slogan. So I have my own perspective on what drop share is, but I don't generally like when other people tell my story badly, so I figure I'll do you the same courtesy. What does Dropshare do? Yeah, so it's basically a piece of software, an app, as you would say nowadays, that helps

you share files, right? So it allows you to drag and drop any file, folder, anything you can think of on your Mac or iOS device, and upload it to virtually any storage provider you can think of, provide you with a link to share it, and that's it. One of the things that I looked for, back when I first encountered this, I wanna say seven years ago or so,

was I was talking to a bunch of people on the internet, as one does, and wanting to send people people on the internet, as one does, and wanting to send people screenshots of things, also as one does, but everything else that I was seeing at the time had their official domain tied to it. It was always very clear what app someone was using, and the flow of these things wasn't terrific either. The initial thing that really got Drop Share onto my radar was the fact that you could use whatever backend storage system you want, like, oh, I don't know,

an S3 bucket in my case. And well, if you do that and then just slap something like CloudFront in front of it, and well, suddenly you can wind up auto-generating screenshots with a hotkey, drag, drop, let go, and suddenly you can send those to everyone. I mean, the domain that I drag, drop, let go, and suddenly you can send those to everyone. I mean, the domain that I use for this, not kidding, is shipposting.pictures because that

is usually what I'm sharing pictures of. I sometimes forget that's what I'm using when I'm in a client discussion and send something quickly to them and then watching them do a spit take in a boardroom. But you know, we all have our peccadillos. Yeah, well, that's rather funny. There is a solution for that in the app, but let's dive into that later maybe. So, finally, you say that it's other solutions, other providers that basically do the same thing, but it's always like branded with their own identity, right? So, and that's actually what made me start Dropshare,

like I think 12 years ago now, maybe 13 years ago. I was relatively new on Mac OS, bought my first Mac and used one of the back then market-leading apps in Take a Screenshot, Share it with a Link. And initially it was great, but yeah, they started adding advertisements to their download page and everywhere it was like, obviously whichever I was using, unless I was to pay money for it, which is fine, on a monthly basis for a tool that I use for taking screenshots. I wasn't so sure about that and I was still a student and that was a no-no for me. So being initially a backend software developer, so that is what I'm by profession, I develop software.

I looked into how hard can it be to create a Mac app, right? How hard can it be the rallying cry of people who are about to learn a lot? Yeah, yeah, precisely. So I spun up Xcode for the first time, looked into it and closed it again for a year or so, because it was like other than anything I had seen before, this weird programming language Objective-C object sending messages to each other. Very weird, coming from a Python and Java background. And yeah, anyway, I was still annoyed for a year. And then I looked back into it with a friend who was back then looking to iOS development also for the first time.

And we helped each other out a bit. And that's when I spent some time and created an app I called Dropshare, I spent some time and created an app I called Dropshare, which basically was a very tiny settings window that allowed me to enter a host name, a password, and a path on my server where to upload files to. Sometimes I share a screenshot of that on Twitter, just for the fun of it. And yeah, I decided to use that.

And suddenly I could just like upload files, capture screenshots with my own domain and my own branding. And people were like, what are you using to do that? And yeah, it was like my app, it wasn't distributed anywhere. It was just running on my Mac. And that's when I started to think about maybe this can be a product. I have to say its flexibility is one of the things that

attracted me to it. At the time, you had a bunch of different cloud backend storage services you could use. And now that I'm looking in version six, you have what appear to be about three dozen of them, ranging from Amazon S3 to the other cloud providers equivalent of it to Google Drive to Dropbox to Imgur. If you want to have your screenshots constantly interrupted with a pop-up, this looks better in the app. I digress that I have angry feelings about it. You can SCP or FTP files into places programmatically.

It is highly customizable. You can also generate custom landing pages that do whatever you want them to do. I confess it took me a little while to figure out the right way to put the meta tags in the landing pages so it would show up properly on Twitter and later Blue Sky. Yeah, so basically when I started to make it a new product,

it supported SCP uploading, so like SSHing into your server uploading files, and Amazon S3 because back then it was like the obvious way to get cheap storage that serves over the internet. And there were, and I think still are, free tiers. So it was basically very easy to set up. It didn't cost anything. I think the app was free back then as well. So it was a win-win for everyone because it was an application sitting in your menu bar, almost invisible.

But there, if you want to share a file or capture a screenshot, people started to download it and apparently to like it. And that's when it grew and more and more storage providers came. I figured all of the object storage providers accepted their fate and implemented an S3 compatible API. So that made it very, very easy to basically attach Dropshare to any of the available storage providers and also allow any custom S3 compatible API if there is a new one that I didn't see yet. And people ask for Google Drive and Dropbox and OneDrive. And yeah, basically everything that has an API can be used with Dropshare. And if it doesn't let me know, I will probably find a way.

You hear from me every time S3 makes a significant change in this direction. I have a history of tickets in my email inboxes dating back, oh, must be to 2018 or so, where it's, hey, reduced redundancy storage isn't really a thing. Now it's infrequent access. Hey, now it's, hey, reduced redundancy storage isn't really a thing. Now it's in frequent access. Hey, now it's intelligent tiering. Can I have the option to upload to that storage class automatically? Yada yada. And your response is always the same of,

oh, thanks for letting me know. I'll look into this in the next version. And lo and behold, I would look a couple months later, and sure enough, either you would email me to say it was available or I discovered it first. It was great. It's not just that you cover a bunch of these storage services but you do it in some significant depth. So I'm very grateful and thankful for the feedback for yours and for the feedback of the community which is a very nice community I have to say because it's not possible for me to follow all the changes and

updates for all the storage providers, because some of them communicate, some of them don't, some of them just change stuff and APIs break. So very thankful and grateful for all these tips. Unless it's not a good idea, I'm very happily looking into it and implementing it, especially since adding a new storage class to the S3 support is really not that big of a deal. You're not tracking this stuff constantly on an ongoing basis. Every change to every storage provider, no matter how minor, can't imagine why. You must have something else to do with your life. Exactly. I wish. And yeah, especially since while Dropshare obviously is a business and I've been doing that for 13 years now, it's not my profession, right? It's something I do on the weekends and when I'm done with work and feel like doing it.

So yeah, again, very thankful for any tips or hints when stuff doesn't work anymore or yeah, just the services change their API or add new features. I want to get into the idea of it as a business a little bit because you have an ancient old-timey business model which is I pay you once for a piece of software and then I effectively get free updates until the next major version which is sort of a nice splitting of the difference between the subscription model and the, okay, we're just going to take money once and then give you free updates for life, which doesn't feel sustainable.

How'd you land there? Yeah, so I've tried it all, I'd say. So the app started with a one-off purchase. There were subscriptions somewhere in between. I think on iOS, it's still possible to opt into a subscription if you don't want to use the app for a long time and don't want to pay the big upfront or lifetime payment for a major version. Now I'm back for many years in the pay once and being an application that primarily targets, like not businesses, but individuals and looking at myself using software.

Um, while that might not be the most businessy way to go, I think it's the most fair way to do it, right? So because I'm not a big business, because I don't have an armada of support people helping, it's just me. I think it's just fair to say, pay once, buy as you've seen it, and whenever something breaks, please shoot me an email. But it might take a week or two for me to fix the issue or to get an update. And I think that's just fair. And on the other hand, Dropshare is on Setup for quite a long time now.

Setup is like the Netflix for applications on Mac OS. And it's like a subscription service. So if someone does not want to pay for their software individually, but rather have a big subscription and get the app from that subscription, that works for me. As long as the software is being used, I can participate on that. I have to confess that I use this so many times a day that when I got the pop-up that hey, there's a new major version out I didn't even bother to read the changelog I hit the link pulled out the credit card bought the upgrade installed it which was a seamless process

by the way, it even gets rid of the old one nice work and Then now I'm talking to you and realized I didn't do my homework well enough What changed in version 6? Because the only thing I would have been likely to notice is if something broke. It didn't. It's been a couple of weeks. That's very good. So it's not like the big bang major update with everything redesigned and updated and

new UI and yada yada because from what I hear from my users and customers, it's fine the way it is. Well, I want to be clear the way that I use it. There is no AI to speak of. I hold down three keys, then I hold two modifier keys and I press the number four and then I drag and I let go. Whatever I've just selected on my screen is now instantaneously uploaded to my S3 bucket. And the link to that accessible via CloudFront is now placed into my clipboard. I can just paste it and go. It is one of the fastest ways I've found of working with these things. I know you have a user interface in various parts of the app, but I almost never have to look at it.

Yeah, I think that's like part of the magic of it, right? It's like sitting in your menu bar almost invisible and it's just there if you need it. And if you don't want to see it, you don't ever need to see it because FU's just perfectly explained. That's how it can work. It can work in very different ways. There can be a visible user interface. The problem that you explained earlier with the shitposting domain, well, theoretically, you could like duplicate your F3 connection, right? And have like two different upload targets, one for the shitpost and one for the business stuff. The app allows that.

It will show you a question window to choose a connection when uploading if you want that. But it's customizable the way you want it to be. So if you don't ever want to see that, it's never going to pop up. Yeah, what changed in version 6 is basically there were a few new storage providers supported. Automatic upload deletions, that is something that people have been asking for quite a while. So if you want your uploads to disappear from your storage after a certain period of time, that's possible now. But it's rather my way of offering that app in a sustainable way, like offering a paid upgrade every five to seven years looking back, then a big bang update that changes everything and adds hundreds of new features and breaks stuff like usually.

So you should check it out if you are using Dropshare already. You should check it out when listening to this episode, obviously, to see whether it can help your workflow, but it's not like to expect major new brand new features because the app is fine the way it is there. It used to be 80, I think, free updates for version 5. Some of them new features, some of them improvements, but I just enjoy working on that product, strive to make it better, but I'm not going to change it in any way that will remove or change the workflow that people started to like and love. This episode is sponsored by my own company, the Duckbill Group.

Having trouble with your AWS bill? Perhaps it's time to renegotiate a contract with them. Maybe you're just wondering how to predict what's going on in the wide world of AWS. Well, that's where the Duck Bill group comes in to help. Remember, you can't duck the duck bill bill, which I am reliably informed by my business partner is absolutely not our motto. How do you look at a feature or an improvement and say, oh, I'm going to put this into the next point release versus this is going to be a paid upgrade for the next major version. How do you draw that line?

Yeah, that's an interesting question. So for the past seven years, there have only been three updates for version five, right? So I released version five, which was a bigger update because like seven years ago, they were like the first Mac OS version with dark mode and UI needed updating to support that. Everyone needs a dark mode for whatever reason. I don't get this obsession with it. So many people have it's sure. Okay, great. Late at night I do. It's a little easier on the eyes, but I don't know that I necessarily want to make that the hill that I die on. Yeah, precisely. But then again, if all of your Mac OS is black and then the settings window pops up and it's

all bright and white, people will write me emails. I've been there. I have no doubt that they will. Yeah. So that's like seven years ago when I needed to do the bigger update, I decided it to be paid. And then I just worked on that for the past seven years. And I didn't even think about a paid upgrade

because people are thankfully constantly buying the app. But then again, looking back seven years, much things have changed, not only economy, but also everything got more complicated, supporting more versions of Mac OS. I thought about it might be a good point now. It's a fair point to release a paid upgrade. Actually, a friend of mine asked me why I'm not doing it and that only made me think about

I could do it because I think it's just fair from time to time to release a paid upgrade because that's how the business stays sustainable in a way. One thing that I keep being surprised at every time I discover it, because I confess I've never used it or configured or gotten it working properly, is you have an iOS version as well, which I guess in hindsight would make a lot of sense for me to have used it a bunch of times

where I just basically throw it over AirDrop from my desktop to do things. That would have made things a lot more simple. But it feels like there's not quite the same equivalent of the friction-free approach of drag, select, or even just effectively hitting other hotkeys to a whole screen image and then store it into that. It feels like there's a few extra steps that need to happen.

It is, obviously, because that's the way iOS is. It cannot be integrated that deep into the OS. But I think one of the primary use cases is that its upload history synchronizes through your iCloud magic synchronization thing. So whenever you upload something on your Mac and you use an iOS device with the same Apple account, your upload history will just appear. So if you shared something and you need it on your phone, you will have easy access to that. And obviously back then when I implemented the iOS app, it made sense also to allow uploads. So not all, but I think like 70% of the storage providers

that are supported on Mac OS are also supported on iOS. And there's not so many native like S3 clients in the app store for iOS devices. So many people just use that to drop stuff into S3 without even needing the like download URL They just want to put stuff in their bucket for later use. That's what makes the app so flexible. You can basically do whatever you need to do with it. You can share the files, you upload it, or you don't. With widgets and share extensions and all that kind of stuff, you can integrate it in your

workflow. So I know that Federico from Mac Updates loved to use the iOS version to upload his blog pictures for the website. Oh, Federico Vettici? Or am I thinking of a different Federico? Yeah, exactly this guy. So he loved to use the iOS app to upload, I think it was even cloud files or so, I don't remember, but yeah, to just get his blog images, assets to his

storage and then use it when updating an article on a website or so. So it can be whatever you need it to be as long as you need to upload something. I very much like the idea of being able to have a configurable self-deletion of a lot of these things. Historically, I've approached that by having a life cycle policy on the S3 bucket, but I have a few screenshots that I've put up over the years that really should have been aimed a little bit differently. For example, one, I sent to someone in passing, well, it wound up getting linked in a New York Times article. That's one of those things where I probably don't want

to move that and break it. Whereas, oh, that was a random misfire as I was testing out a new keyboard shortcut that did not do what I thought it was going to do. I wind up with things cluttering up that S3 bucket constantly. I think last time I checked I had 7,000 images in that thing. Yeah, so apparently auto deleting is something that people wanted to have. I was a little

hesitant to implement that because like people tend to forget stuff, right? So data just disappearing from your storage is a little scary, but I'd say well hidden in the app and made sure that it just precisely does what you want it to do. And obviously only works if the Mac and the app is running at the time because there's no intermediate. Dropshare is always only going to directly communicate with your storage. There's nothing in between that will ever

get in touch with your files. But yeah, people love that. And I've already gotten some feedback on it. And people requested more customization options for the duration and the lifetime of the file. So yeah, that is what I'm actually very grateful for the lifetime of the file. So yeah, that is what I'm actually very grateful for, the community of the app, because people are very understandable for why there's now a paid upgrade.

And on the other hand, have very good feedback like you did many times in the past on how to improve the app. And it's always like in my professional career, it's always a compromise between what the customers want, what the product is supposed to be, what the product managers imagine their product to be. But in this case, and that is why I enjoy to work on dropshare so much, it's just me, right? The only one I need to argue with is me. And if I think it's a good idea and like the feature, I'm just going to implement it. Part of the problem that I consistently run into is that I spend all of my professional time fixing horrifying AWS bills, a small problem that's affected basically everyone in the fullness of time. And that's why I cared so much about getting intelligent tiering working with this and then I stopped to think. I mean really think about this and I

checked the numbers and I'm spending about seven cents a month right now on storage for all the things I've taken pictures of over the last eight years and it turns out that I don't actually care about optimizing that seven cents down to five or whatnot. What I do care about, and why I like that deletion feature quite a bit, is that I will periodically, either intentionally or accidentally, take screenshots of things that are somewhat sensitive.

And that's fine. There's a long random string that's part of the name of these things that winds up being, so it's not discoverable. You can't list index these things. And I know how S3 permissions work so I'm mostly safe there but I still don't like having that data hanging around and being able to have that delete in the fullness of time is a significant value. It is I think and well something else that's hidden kind of well in the app but has been there for I I think, since basically the beginning.

It's something that I call Dropshare Safe, which is an option to add a password protection and the link expiry to your upload. So it's not touching the file itself but just putting a site in front of that file with the secret URL you just mentioned and allow you to like set up a password to download it or set an expiry for just the link. And if you then share that drop share save link, no one's ever going to find out the actual URL of that file. And without the password, yeah, obviously not going to able to download it unless you share the actual file anywhere. I also have misled you. I'm trying to remember off the top of my head. That's why I checked and pulled this up. Yeah, this has cost me 11 cents total

over the past six months in storage. So yeah, maybe that's not the first thing I should cost optimize. Maybe I just get a medium coffee instead of a large and cover the difference for the next year. That sounds like a good plan. I am curious as well about what seems to have, of a large and cover the difference for the next year. That sounds like a good plan. I am curious as well about what seems to have,

I sort of stumbled upon this on GitHub. It feels like there's a thriving community around dropshare, which I want to just say is a wild thing to say about a relatively straightforward app that takes screenshots and puts them on the internet, but specifically around various tailored landing pages, the templates of whenever something gets thrown up there and I drop the link, it's not just a link to the raw image because that'll break a lot of things.

It's a bare bones HTML page that will in turn have embedded tags so it displays properly on various websites. I need to go back and look at that a fair bit more because I suspect there are better options in what I'm using that arrange for things like, I don't know what the alt text equivalent is for use on social media or changing the aspect ratio at which they display these things. But I'm sure they're out there and I'm sure someone has done that heavy lifting for me. But it's one of those incremental improvements. It's just quality of life stuff. Yeah, precisely. And many of the landing pages, as I call them, that are built into the app are community made, right?

So someone just made their own landing page, showed them on GitHub and tagged me and said, hey, this is nice, don't you want to put that into the app? And that's what I did because I'm not a really good web designer, right? So I wouldn't come up with plenty of templates to use. But if there isn't any that you like built into the app, you can, as you said, just spin up the HTML editor and create your own tiny landing page for your uploads. Put some placeholders in there that will be replaced with a preview image or the name of the file, the size of the file, whatever. And have your own CI or whatever you need for your downloads.

It's also probably worth pointing out that, for better or worse, AI can do a pretty decent job of banging these things together these days. Yeah, so that was rather a joke, to be honest, but turned out to be quite a helpful feature sometimes. So usually if you take a screenshot, it's very simply named screenshot with a date, right? So there is preview images of the files obviously in the app, but still sometimes if you actually need to find something that you captured like two weeks ago can be quite a hard. But yeah, some time ago, OpenAI came out with a model that was able to very efficiently analyze a screenshot and give it a good name.

And that's what the app can do if you want it to. So you can just hook it up with your OpenAI key and have all the screenshots you take annotated for better findability in the app. And it will also, as a nice tidbit, add that description to the metadata of the file on your Mac. So also when using Finder for the local file, for example, you will more easily find it based on what's in the screenshot. And it turned out to work rather well. Wasn't that hard to implement. And yeah, now I can say I have an app that does AI as well. I miss that option in the preferences that that sounds super handy. Not not from the perspective of I want AI to do all of my work for me. But oh my god, as I said, I have 7000 images in an S3 bucket. It sure would be nice to start annotating that in the fullness of time, especially with

S3's new metadata feature they just launched at re.invent and went in GA about a month ago. I still haven't wrapped my head around that, but once I do, don't worry, you'll get another feature request that sounds like it came from the freaking moon dropping into your chat box. Looking forward to that. Timo, thank you so much for taking the time to speak with me. If people want to learn more, or as I strongly suggest they do, buy Dropshare, where should

they go? It was a pleasure. So it's dropshare.app. Very easy. Excellent. And we will of course put a link to that in the show notes. Thank you so much for being so generous with your time. I appreciate it. Pleasure. Thank you for having me.

Timo Joosten, owner of Dropshare. I'm cloud economist Corey Quinn, and this is Screaming in the Cloud. If you've enjoyed this podcast, please leave a five-star review on your podcast platform of choice. Whereas if you've hated this podcast, please leave a five-star review on your podcast platform of choice, along with an angry, insulting comment that you should then take a screenshot of for posterity, but lose it because you don't have a reasonable app to upload it somewhere sensible. Bye!