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Dropbox buys HelloSign (YC W11) for $230M

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121–130 of 164 posts

Re: Dropbox buys HelloSign (YC W11) for $230M

#121

As someone who has never worked in an enterprise SaaS will never fully understand the hype or secret sauce around building and selling eSignature software.

I designed software for the AEC industry in the past. You wouldn't believe how engrained are signatures in their mental model for doing things. So much, that we once ended up builiding a functionality that required a scribble that would get attached to a finalized inspection.

Not like that was different from simply pressing a button and acknowledging some message. No cryptography, no standards about legally binding e-signaturees, nothing. They just wanted the scribble of the inspector attached to the form.

Signatures are basically a way of signaling approval, ackowledging something or declaring intent. I designed that feature and always thought about it more as a intentional friction to make someone think briefly before closing or approving an inspection.

Re: Dropbox buys HelloSign (YC W11) for $230M

#122
post #113
post #105

Earlier quoted context omitted.

This is security by obscurity, it's still technically possible to access the documents. Like if you accidentally revealed the URL somehow. You shouldn't have to worry about things like that.

Surprisingly, it turns out that using security based on a URL with a random string is /not/ security by obscurity. The security pattern of a URL with a random string is security-equivalent to a pubic username and a random string password, and also equivalent to the security pattern of a bearer token: so long as the URL is shared only with authorized users, it's the same security hardness. The pattern can tune the sec…

Browsers do not treat URLs as secure. If you just go to the page and happen to be live-streaming on Twitch or whatever, anyone can access the document because the information is printed visibly on the screen. This makes it starkly different from a password.

Re: Dropbox buys HelloSign (YC W11) for $230M

#123
post #88

This is awesome news, congrats folks!! Have relied on hellosign over the years, including doing all of my home buying paperwork with it.

I've used HelloSign as well, but every other app that I used that Dropbox bought has been discontinued so while I'm happy for the team, I don't have high long term hopes for the project.

Ugh, yeah they bought and then slowly killed off Mailbox. :(

Re: Dropbox buys HelloSign (YC W11) for $230M

#124
post #92

I don't mean to ask this ironically; how do these companies come up with these numbers during a sale? Jet.com was sold for $3 Billion, but Craftsman Tools was sold for only $900 Million. I don't really know anything about HelloSign, but can someone tell me roughly why they might have come up with the $230M number?

revenue * multiple let's say $10m in ARR * a 23x multiple The way you get to the multiple is a combination of how fast the revenue is growing, how long you think that will keep up, and the margin of the revenue. Craftsman Tools, for example, was probably not growing much or shrinking and likely had low margin revenue but I don't know.

Revenue is almost meaningless. At least use a multiple of profits or of net income.

You know, you can have a crazy revenue, and still lose money, and your company can be bankrupt in a few months.

Re: Dropbox buys HelloSign (YC W11) for $230M

#125
post #105

Earlier quoted context omitted.

The URLs contain a long random string in them, no? This makes them unguessable. Public-by-default seems to enable easy sharing of documents. I would hope that corporate plans would impose stricter privacy controls, but for personal use, being able to share a document just by sharing its URL seems very convenient. Though I suppose defaulting the permissions such that anyone with the URL can edit the document seems may…

This is security by obscurity, it's still technically possible to access the documents. Like if you accidentally revealed the URL somehow. You shouldn't have to worry about things like that.

It’s obscurity in the same way a password or a bearer token is obscurity. Which is not what anybody would reasonably call security by obscurity, as your definition includes any use of a secret.

Re: Dropbox buys HelloSign (YC W11) for $230M

#126
post #92

I don't mean to ask this ironically; how do these companies come up with these numbers during a sale? Jet.com was sold for $3 Billion, but Craftsman Tools was sold for only $900 Million. I don't really know anything about HelloSign, but can someone tell me roughly why they might have come up with the $230M number?

Esignature is a huge business and the incumbents have a high cost structure or a history of excessive price increases. (Would you want to build your strategy around Adobe?)

This gives Dropbox something to anchor against. Both Google and Microsoft improve every quarter, while Dropbox is mostly the same, with the same premium pricetag. I could move my whole company to Dropbox for a couple of million, OneDrive is $0.

Re: Dropbox buys HelloSign (YC W11) for $230M

#127
post #92

I don't mean to ask this ironically; how do these companies come up with these numbers during a sale? Jet.com was sold for $3 Billion, but Craftsman Tools was sold for only $900 Million. I don't really know anything about HelloSign, but can someone tell me roughly why they might have come up with the $230M number?

Many of my clients (F500) use HelloSign and DocuSign. They are not DropBox customers. I think what follows is rather obvious.

Re: Dropbox buys HelloSign (YC W11) for $230M

#128
post #21

Earlier quoted context omitted.

The law isn’t like programming. The reason you sign something is to show clear intent that you intended to agree to something. Nobody’s under the impression a paper signature cannot be forged either. It’s no different. It’s social not mathematical.

Then that leads to my second question >Why do we need them at all? Why not just email the contract, and the person replies back with "I agree to this"? Simpler and cheaper than paying $150/year.

You can absolutely do that. It works between two parties especially when small very well, but doesn’t scale well.

It’s also problematic when you deal with an asshole, as it’s difficult to determine who has the correct version of the message.

Re: Dropbox buys HelloSign (YC W11) for $230M

#129
post #40

Earlier quoted context omitted.

Because the ceremony of a signature has been socially recognised for thousands of years. That's what our society expects.

>Because the ceremony of a signature Come to think of it, I remember "signing" pdfs in adobe reader by clicking a form field that produced a signature similar to[1]: John Smith Digitally signed by CN=John Smith [...] This would satisfy the "ceremony" requirement. According to adobe[2] it looks like you can do this with self signed certificates, so it's completely free as well. But this option is significantly less po…

It’s only free for a certain number of signatures per form. Then you need to buy some server side tool from Adobe, and $150/yr seems cheap.

Re: Dropbox buys HelloSign (YC W11) for $230M

#130
post #40

Earlier quoted context omitted.

Because the ceremony of a signature has been socially recognised for thousands of years. That's what our society expects.

>Because the ceremony of a signature Come to think of it, I remember "signing" pdfs in adobe reader by clicking a form field that produced a signature similar to[1]: John Smith Digitally signed by CN=John Smith [...] This would satisfy the "ceremony" requirement. According to adobe[2] it looks like you can do this with self signed certificates, so it's completely free as well. But this option is significantly less po…

Adobe's failure to make this easy and free is the problem. How HelloSign gets away with not also embedding digital signatures is the amazing part. Physical signatures are terrible security, at least when we switch to digital make it better, not worse.
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