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mrweasel 53 minutes ago [-]
Somewhat off-topic: When writing like this, explain your abbreviations and who the various people and companies are. PE Target? Price to Earnings Target, that makes no sense. Perhaps Physical Education, no, that's not right either. 10-K (might bold to assume that the reader knows what that is). Even smb (which should be SMB, even if it doesn't help) is probably not Small Message Block.
Think what you will of their writing and opinions, but one thing The Economist get right is that they don't assume you know what things are, it's spelled out at the first mention. So first mention of PE would be: private equity (PE).
Or
> And Sequoia’s (a venture capital firm) investment in Dropbox was a great one, second to Airbnb in Fund 12 (another venture capital firm).
motoxpro 26 minutes ago [-]
I think the people who need those abbreviations spelled out are not the target audience of the article. There is no possible way to think that PE == price to earnings/physical education here and if a reader thinks that they wont understand the article anyway. e.g. hamilton helmer, power, fund 12 being a sequoia fund not a different venture firm, etc.
Its OK for articles to be a short few paragraphs with a smaller audience rather than a few long pages and explain every single thing at a basic level to try reach everyone
ElProlactin 3 hours ago [-]
Not sure why this is on the front page but anyway...
> But a lesson from this story is twofold: when Steve Jobs tries to buy you, take it. Economically, the return from a capital efficiency standpoint would be much better. Second, public companies that are truly just a feature never give you great returns.
Dropbox was a private company when Jobs offered to buy it for $800 million in 2009. Drew Houston (the founder) has collected hundreds of millions of dollars in compensation since then and is today worth over $2 billion. He's also on the board of Meta.
So the point about investing in companies that are features might be a decent (if obvious) one for retail investors looking at public equities, but the lesson here isn't "when Steve Jobs tries to buy you, take it".
bouk 19 minutes ago [-]
$800M in 2009 Apple stock would be about $24B today!
wongarsu 1 minutes ago [-]
But $800M in USD is worth only about $1.2B today. Keeping the money invested in Apple is convenient if you're already paid in stock, but beyond the lock-up period we have to keep in mind that it's just one of many things he could have done when accepting the money
Though I think it fair to speculate that if he had taken the deal he would likely have more money today, at the cost of less status
retired 2 hours ago [-]
I would have taken the 800 million and retired. Would easily be worth 1.5 billion with simple investment. And you would not have needed to work those 17 years.
stymaar 21 minutes ago [-]
If he wanted to “retire” he never had to wor in the first place, he could have hired someone to take his jobs while still keeping his equity.
But being the CEO of a well-known startup has a lot of status benefits compared to just being rich. And that's all what matters at this level of wealth.
And it gives you a sense of purpose, which we all need.
ElProlactin 2 hours ago [-]
But you're not Drew Houston.
monooso 56 minutes ago [-]
The advice isn't for Drew Houston, it's written as general advice for anyone.
The point is that different people have different priorities, and retiring in your mid-twenties to enjoy your many millions is a perfectly reasonable choice.
somenameforme 21 minutes ago [-]
Until one does it and realizes that the concept of retirement is not the same as the reality of such, especially for people who like achieving things, which is going to essentially be 100% of people who end up making millions in their 20s. I think this is why so many billionaires choose to be workaholics even though they have the means to do literally almost anything.
monooso 13 minutes ago [-]
In which case, fine, return to work, start a new company, start a foundation, whatever. Accepting the aforementioned big fat cheque from Steve Jobs affords you those options.
retired 2 hours ago [-]
Correct. At the 26 years old that he was I would take the millions and just have a chill life. Maybe start collecting rare Lamborghinis.
ElProlactin 2 hours ago [-]
And maybe that's why you didn't start Dropbox.
retired 2 hours ago [-]
Still started and sold my own company. Quit working. But no, it wasn’t Dropbox.
Taikhoom10 2 hours ago [-]
which company?
sunnybeetroot 44 minutes ago [-]
OneDrive
testdelacc1 39 minutes ago [-]
It’s right there in his name. Retired Inc.
Taikhoom10 3 hours ago [-]
I was referring to multiples on invested capital. Plus, it's a bit hurtful when you IPO your company, the stock stays flat if not down, and you step down; I think an Apple acquisition like that is much more of a happy ending IMO.
ElProlactin 2 hours ago [-]
You're thinking like an investor, not an entrepreneur/founder.
Taikhoom10 2 hours ago [-]
Yes, you're right
perks_12 37 minutes ago [-]
Dropbox pulled the plug on so many good apps. They should have built the full office suite in the browser and eventually slapped an email service on it. As a competitor to Google Workspace, they would have a real chance. Storage as a Service is too little of a moat in the cloud age.
dgoldstein0 15 minutes ago [-]
Out of curiosity which apps do you miss the most?
paxys 3 hours ago [-]
> But a lesson from this story is twofold: when Steve Jobs tries to buy you, take it.
Not quite sure how the author reached that conclusion, considering – by their own calculations – Dropbox is profitable, rich on cash flow and worth at minimum 10x what Steve Jobs offered for it.
Taikhoom10 3 hours ago [-]
Right, but you have to consider how early on this was, with little venture raised; multiples are way better. My point was bundling wins in the long term.
ElProlactin 2 hours ago [-]
Yeah, if he had sold and taken his money and invested it all in BTC or FB or Nvidia he would have been one of the richest people in the world.
What you're missing is that he was able to build his company, run it for years, get paid well and step down from the CEO position with a stake worth a couple of billion dollars.
You can't always reduce everything to money. Lots of entrepreneurs, perhaps the majority, would consider Drew's outcome to be the ideal one: you get to do what you love, raise your baby and earn a fortune.
Not everyone wants to sell out, start a family office and spend their days on a boat pondering what the purpose of life is and what they should do next.
retired 1 hours ago [-]
Work at a soul sucking corporate for 17 years instead of enjoy life traveling around the world? In what way does that sound good?
Reaction to fragmede as I am rate limited:
You don’t have to travel full time.
And yes working at Dropbox is boring. Dropbox stores files. Things haven’t changed since 2009. There is not any product growth. They still store files. 95% of their daily operations is sales. That doesn’t sound enticing to me.
wickedsight 6 minutes ago [-]
> Work at a soul sucking corporate for 17 years instead of enjoy life traveling around the world?
It might be difficult to believe, but some people enjoy running companies just as much as others enjoy traveling the world. Different people have different interests and goals in life. Neither is wrong.
Also, we can't just have people who retire as soon as they have enough money to travel around the world for the rest of their lives, we would only have inexperienced people in many important positions. 3 million is probably enough for that, if you don't demand too much luxury, and that's close to 1% of US families.
fragmede 1 hours ago [-]
If you hate travelling, in what way does doing that for 17 years sound like fun? Some people just do not like traveling and living out of a suitcase or backpack. Others, do. If you see being at a corporation as soul sucking, then don't, but I imagine that if you're the CEO of the corporation, it's a different story than if you're a drone, and see yourself as one. Retirement is great, you get to choose what to do. Some people choose to fuck off to the beach. Others choose to keep writing code, like Larry Finger. No one's gonna shame you for not being Larry Finger in your retirement, but we should celebrate the people who chose to do good works.
rglullis 56 minutes ago [-]
For the system, there is not a lot of difference whether you are the slave or the slave driver. But oh boy would the system be in in trouble if it had more free people around...
ggm 2 hours ago [-]
Not spending time with 10/100/1000 millions people very much I appreciate there may be a boundary between 10 amd 100 but between 100 and 1000 I remain unsure there is a functionally useful distinction which would motivate me, per the money. Maybe it's about the zero as a rei-ified thing in itself but if somebody decides to stop at 100 and you argue they should have driven to 1000 what axiomatically makes you "right"?
This feels like a judgement purely in financial numerology. Is bigger of necessity "better" for every founder?
blitzar 54 minutes ago [-]
I have a few qualms with this PE Target:
1. For a Linux user, you can already build such a system yourself quite trivially by getting an FTP account, mounting it locally with curlftpfs, and then using SVN or CVS on the mounted filesystem. From Windows or Mac, this FTP account could be accessed through built-in software.
2. It doesn't actually replace a USB drive. Most people I know e-mail files to themselves or host them somewhere online to be able to perform presentations, but they still carry a USB drive in case there are connectivity problems. This does not solve the connectivity issue.
3. It does not seem very "viral" or income-generating. I know this is premature at this point, but without charging users for the service, is it reasonable to expect to make money off of this?
mickael-kerjean 47 minutes ago [-]
> From Windows or Mac, this FTP account could be accessed through built-in software.
It is primarily a switching-cost-enabled cash cow.
telotortium 3 hours ago [-]
Bending Spoons must be watching Dropbox closely. Like the other companies that have been acquired by them, Dropbox has reached its final stage of stability.
thinkindie 56 minutes ago [-]
They acquired already WeTransfer and Dropbox could be a natural fit with that.
syncthing replaced dropbox for me.
and for cloud the existing solutions are better google drive,icloud, onedrive
but actually I use restic and a s3 compatible bucket.
nugzbunny 3 hours ago [-]
I used to use Dropbox at work and also personally.
Work didn’t like it as Dropbox was new/unknown and eventually banned us from using it. This was about 15 years ago and the only way to share files between colleagues was to manually upload a file to their shared drive (through a browser) and then ask your colleague to go download it.
Works Dropbox was replaced by Microsoft. My personal Dropbox was replaced by Google Drive, and then by iCloud.
Nice to know Dropbox is still make lots of cash really. They started it all.
jh00ker 3 hours ago [-]
>They started it all.
Actually box.com was first (launched as box.net in 2005), and Dropbox was founded in 2007.
zrobotics 2 hours ago [-]
I mean if we're going to get pedantic like that, then here is the classic Dropbox evaluation:
BrandonM on April 5, 2007 | parent | context | favorite | on: My YC app: Dropbox - Throw away your USB drive
I have a few qualms with this app:
1. For a Linux user, you can already build such a system yourself quite trivially by getting an FTP account, mounting it locally with curlftpfs, and then using SVN or CVS on the mounted filesystem. From Windows or Mac, this FTP account could be accessed through built-in software.
2. It doesn't actually replace a USB drive. Most people I know e-mail files to themselves or host them somewhere online to be able to perform presentations, but they still carry a USB drive in case there are connectivity problems. This does not solve the connectivity issue.
3. It does not seem very "viral" or income-generating. I know this is premature at this point, but without charging users for the service, is it reasonable to expect to make money off of this?
tmp10423288442 58 minutes ago [-]
Everyone makes fun of #1 for good reason, but #2 and #3 were actually reasonable objections at the time.
Yes and quite frankly dropbox should have leverage their consumer brand to move into enterprise.
kelvinjps10 19 minutes ago [-]
I remember gaining a bunch of storage from dropbox because they used to have this program where you gained storage by doing referrals.
but then they removed it after I had invited so many people and I didn't want to keep using the service at all.
Now I use syncthing (no cloud needed)
eps 1 hours ago [-]
It would've helped to clarify that "PE" stands for "private equity".
motoxpro 12 minutes ago [-]
You should send these out in a newsletter
raz32dust 3 hours ago [-]
Sad. I still use Dropbox personally and really like their use experience, but I just don't find enough use for it to pay for a service like that. The technology proved to be far too easy to replicate and they failed to build anything that would make users stick around, I guess. Maybe moving to workspace collaboration solution like Google docs was the play?
As much as I hate it, capturing users and building a walled garden seems to be the only way to make it really big.
andreidbr 3 hours ago [-]
I recently migrated to a new phone and one of the apps I had to re-login was Dropbox. A feeling of nostalgia washed over me. It was absolutely essential many years ago but now the competition is huge. I'm not a fan of Private Equity but if it can keep the business alive, then it's worth exploring by the leadership.
Krutonium 3 hours ago [-]
PE's end goal is never the health of the business.
Being bought by PE is a death sentence. Maybe drawn out by years, but a death sentence none the less.
matwood 58 minutes ago [-]
In most cases you have the causal effect of PE incorrect. By the time PE comes in, the company has already peaked and is on a downslope. The original owners know this, want to get out and sell. Blaming PE is like blaming vultures for the roadkill they are picking over.
shuwix 2 hours ago [-]
Exactly ... PE's wants shorterm return, just numbers in a sheetbook, and they special execs for such jobs. Their only "strategy" (my dog can figure out better) is aggresive monetization, layoffs pushing remaining employees to limits.
Profits goes up ... so the strategy must work, lets increase monetization more and do more layoffs.
Prices goes up, quality of service goes down.
After few years, everything goes down the drain, PE and their execs can't figure out what went wrong.
edoceo 3 hours ago [-]
And despite their patterns giving not that great returns they keep doing it. Mostly it's an income play vs capital appreciation anyway. If you wanted the capital gains pre-seed and seed are doing well. ACA had a report which I think also got mentioned in Bloomberg.
Taikhoom10 3 hours ago [-]
It depends on the acquirer; Silver Lake could be a good partner.
oersted 2 hours ago [-]
That's an oversimplification. Private Equity's goal is to take control of the business and change it so that it has higher resell value.
Often they do sell it for parts, or they enshitify the hell out of it to squeeze revenue from loyal customers. Not necessarily because it's the optimal strategy, but because truly fixing a business is hard and these are decent shortcuts from their perspective.
But that's not a given, sometimes they do truly turn it around for the better.
bombcar 3 hours ago [-]
Dropbox was huge before everything built in sync as SaaS. I still fondly recall the Dropbox backend to 1Password.
chorsestudios 2 hours ago [-]
I understand why it is a reasonable acquisition target for PE and worthy of exploration, but I’m not sure I understand how being acquired by PE would keep Dropbox alive longer other than shaking up the leadership and shifting priorities. Perhaps aggressively targeting enterprise customers currently using Box after rolling out the necessary features?
Taikhoom10 3 hours ago [-]
No, definitely agree. One of the great SaaS companies, strategy matters, though, and the early success distracted them from building a defensible business.
yojo 3 hours ago [-]
I was at Dropbox from 2016-2020. We were certainly trying to build a sustainable business, but there was a major identity crisis. Were we consumer web? Buy Mailbox and build Carousel, then shut them both down.
Maybe we’re Notion/Evernote? Buy Hackpad, plow a ton of money into Paper (which was legitimately good), then quietly deprioritize it.
Maybe we’re actually some kind of enterprise document productivity suite? Buy HelloSign. Plow a bunch of money into a desktop app. Pull more plugs.
A lot of smart people were trying. We made a lot of bets (too many?). None of them proved to be a second act, and the competitors eventually caught up.
Taikhoom10 2 hours ago [-]
I intend to write a piece going deeper into the failures; I would love to chat if you're open to it. Also, not to say Dropbox sucked or anything, it is just that the broader strategy and industry structure make it hard; if anything, the success of the first product made it difficult to evolve the business.
OCTAGRAM 3 hours ago [-]
I recall I was using Dropbox on Windows 2003 and Mac OS X 10.4. I was student and actively writing Office documents, AutoCAD, NanoCAD, LabVIEW, plenty of cryptic formats. Eventually Dropbox stopped working on Mac OS X 10.4. And I was not student anymore, I was not dealing with folders. As developer I worked with TortoiseHg and BitBucket, Mercurial repositories and reStructured Text wikis. And returned to neither Dropbox nor similar alternatives. By inertia I synchronized with Dropbox, but when Dropbox stopped working on Mac OS X 10.4, it stopped at all. Eventually I've got OS upgrade, but Dropbox already gone and never returned.
crossroadsguy 45 minutes ago [-]
There are not many companies around with so much of voluntary important/intimate personal data as Dropbox has. PEs have gone for smaller note taking apps.
> ICloud went on to become a bigger business than Dropbox
And a worse app/service and that's saying something because Dropbox isn't even a shell of what it used to be. I'd agree with Jobs' observation of original Dropbox being a feature. But not any more.
As for "take it".. really?
> The product has largely remained the same
It seems to be coming from someone who hasn't been using Dropbox, at least not of late.
Also, I think their paying users used to be 2-3%. So yes PEs like this kind of chance of quick squeeze and squeeze and dry it and then leave it to die. I would reckon PEs would see a lot of one-time juice making opportunity here.
krzyk 2 hours ago [-]
I'm surprised Dropbox is still around, was it 15 years ago when I used? It was something new, but after they started pushing limitations I stopped using it.
sbennettmcleish 55 minutes ago [-]
I'm still a paying customer from somewhere before 2010, don't use it consistently but I've got a ton of things in there. Every time the anniversary rolls around in November I ponder how much effort to move off it for the not insignificant cost, but then the desire fades until about the next November :)
Taikhoom10 2 hours ago [-]
I know, right! Switching costs are powerful.
devops000 54 minutes ago [-]
Maybe Bending Spoons could buy it?
snozolli 2 hours ago [-]
Call me crazy, but I think we need more Dropboxes and fewer Metas or whatever.
Make a product that solves a sufficiently common problem, and make it extremely high quality. Want more growth? Find another problem to solve and launch a product in that space.
As for Steve Jobs and selling out, Apple bought FingerWorks. That's how they ended up with excellent, multi-touch touchpads while the rest of the computing world suffered. Make great products (or "features") and never sell out to soulless megacorps.
The premise of the article that "Dropbox was .. a feature, not a Product" is complete nonsense. Remember the infamous FTP guy's top comment during their launch? I have spent almost 10 years working on making that vision a reality [1], and there are entire industries built around some variation of it: digital asset management, managed file transfer, digital preservation software, electronic document management systems, ...
Think what you will of their writing and opinions, but one thing The Economist get right is that they don't assume you know what things are, it's spelled out at the first mention. So first mention of PE would be: private equity (PE).
Or
> And Sequoia’s (a venture capital firm) investment in Dropbox was a great one, second to Airbnb in Fund 12 (another venture capital firm).
Its OK for articles to be a short few paragraphs with a smaller audience rather than a few long pages and explain every single thing at a basic level to try reach everyone
> But a lesson from this story is twofold: when Steve Jobs tries to buy you, take it. Economically, the return from a capital efficiency standpoint would be much better. Second, public companies that are truly just a feature never give you great returns.
Dropbox was a private company when Jobs offered to buy it for $800 million in 2009. Drew Houston (the founder) has collected hundreds of millions of dollars in compensation since then and is today worth over $2 billion. He's also on the board of Meta.
So the point about investing in companies that are features might be a decent (if obvious) one for retail investors looking at public equities, but the lesson here isn't "when Steve Jobs tries to buy you, take it".
Though I think it fair to speculate that if he had taken the deal he would likely have more money today, at the cost of less status
But being the CEO of a well-known startup has a lot of status benefits compared to just being rich. And that's all what matters at this level of wealth.
And it gives you a sense of purpose, which we all need.
The point is that different people have different priorities, and retiring in your mid-twenties to enjoy your many millions is a perfectly reasonable choice.
Not quite sure how the author reached that conclusion, considering – by their own calculations – Dropbox is profitable, rich on cash flow and worth at minimum 10x what Steve Jobs offered for it.
What you're missing is that he was able to build his company, run it for years, get paid well and step down from the CEO position with a stake worth a couple of billion dollars.
You can't always reduce everything to money. Lots of entrepreneurs, perhaps the majority, would consider Drew's outcome to be the ideal one: you get to do what you love, raise your baby and earn a fortune.
Not everyone wants to sell out, start a family office and spend their days on a boat pondering what the purpose of life is and what they should do next.
Reaction to fragmede as I am rate limited:
You don’t have to travel full time.
And yes working at Dropbox is boring. Dropbox stores files. Things haven’t changed since 2009. There is not any product growth. They still store files. 95% of their daily operations is sales. That doesn’t sound enticing to me.
It might be difficult to believe, but some people enjoy running companies just as much as others enjoy traveling the world. Different people have different interests and goals in life. Neither is wrong.
Also, we can't just have people who retire as soon as they have enough money to travel around the world for the rest of their lives, we would only have inexperienced people in many important positions. 3 million is probably enough for that, if you don't demand too much luxury, and that's close to 1% of US families.
This feels like a judgement purely in financial numerology. Is bigger of necessity "better" for every founder?
1. For a Linux user, you can already build such a system yourself quite trivially by getting an FTP account, mounting it locally with curlftpfs, and then using SVN or CVS on the mounted filesystem. From Windows or Mac, this FTP account could be accessed through built-in software.
2. It doesn't actually replace a USB drive. Most people I know e-mail files to themselves or host them somewhere online to be able to perform presentations, but they still carry a USB drive in case there are connectivity problems. This does not solve the connectivity issue.
3. It does not seem very "viral" or income-generating. I know this is premature at this point, but without charging users for the service, is it reasonable to expect to make money off of this?
This is exactly what I've done: https://github.com/mickael-kerjean/fdrive https://github.com/mickael-kerjean/filestash
Work didn’t like it as Dropbox was new/unknown and eventually banned us from using it. This was about 15 years ago and the only way to share files between colleagues was to manually upload a file to their shared drive (through a browser) and then ask your colleague to go download it.
Works Dropbox was replaced by Microsoft. My personal Dropbox was replaced by Google Drive, and then by iCloud.
Nice to know Dropbox is still make lots of cash really. They started it all.
Actually box.com was first (launched as box.net in 2005), and Dropbox was founded in 2007.
BrandonM on April 5, 2007 | parent | context | favorite | on: My YC app: Dropbox - Throw away your USB drive
I have a few qualms with this app:
1. For a Linux user, you can already build such a system yourself quite trivially by getting an FTP account, mounting it locally with curlftpfs, and then using SVN or CVS on the mounted filesystem. From Windows or Mac, this FTP account could be accessed through built-in software.
2. It doesn't actually replace a USB drive. Most people I know e-mail files to themselves or host them somewhere online to be able to perform presentations, but they still carry a USB drive in case there are connectivity problems. This does not solve the connectivity issue.
3. It does not seem very "viral" or income-generating. I know this is premature at this point, but without charging users for the service, is it reasonable to expect to make money off of this?
As much as I hate it, capturing users and building a walled garden seems to be the only way to make it really big.
Being bought by PE is a death sentence. Maybe drawn out by years, but a death sentence none the less.
Prices goes up, quality of service goes down. After few years, everything goes down the drain, PE and their execs can't figure out what went wrong.
Often they do sell it for parts, or they enshitify the hell out of it to squeeze revenue from loyal customers. Not necessarily because it's the optimal strategy, but because truly fixing a business is hard and these are decent shortcuts from their perspective.
But that's not a given, sometimes they do truly turn it around for the better.
Maybe we’re Notion/Evernote? Buy Hackpad, plow a ton of money into Paper (which was legitimately good), then quietly deprioritize it.
Maybe we’re actually some kind of enterprise document productivity suite? Buy HelloSign. Plow a bunch of money into a desktop app. Pull more plugs.
A lot of smart people were trying. We made a lot of bets (too many?). None of them proved to be a second act, and the competitors eventually caught up.
> ICloud went on to become a bigger business than Dropbox
And a worse app/service and that's saying something because Dropbox isn't even a shell of what it used to be. I'd agree with Jobs' observation of original Dropbox being a feature. But not any more.
As for "take it".. really?
> The product has largely remained the same
It seems to be coming from someone who hasn't been using Dropbox, at least not of late.
Also, I think their paying users used to be 2-3%. So yes PEs like this kind of chance of quick squeeze and squeeze and dry it and then leave it to die. I would reckon PEs would see a lot of one-time juice making opportunity here.
Make a product that solves a sufficiently common problem, and make it extremely high quality. Want more growth? Find another problem to solve and launch a product in that space.
As for Steve Jobs and selling out, Apple bought FingerWorks. That's how they ended up with excellent, multi-touch touchpads while the rest of the computing world suffered. Make great products (or "features") and never sell out to soulless megacorps.
[1] https://github.com/mickael-kerjean/fdrive | https://github.com/mickael-kerjean/filestash