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Congrats Dropbox

blog.ycombinator.com

211–220 of 285 posts

Re: Congrats Dropbox

#211
Eh they should have stayed private. Private companies have more control over their future. Public companies move to a quarter by quarter cycle and innovation goes at a snail's pace as marketing and bean counters take over.

Re: Congrats Dropbox

#212
post #70

Earlier quoted context omitted.

So 600M is the upper bound. Drew Houston owns roughly 25% of the company now, and he probably owned ~75% at when YC invested, for a dilution rate of 3. I'd say YC investment probably has dilution rate of 10, for the real amount of 60M. Not bad, but not Whatsapp scale either.

Dumb question: Why would YC get diluted so much more than DH? I've started to read up on venture financing and this doesn't match my mental model for any of the mechanisms I've learned about. (Like if anything I'd expect YC to have less dilution due to follow-on/pro rata investments, if they did any.)

I believe that when founders stock is fully vested, additional grants are an option to retain the founders beyond 4 years (or whatever the founders stock beating period is). 11 years as CEO likely led to additional grants. For a much bigger example, look at the additional grant Musk got this last week for Tesla.

Re: Congrats Dropbox

#213

Earlier quoted context omitted.

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…

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.

Re: Congrats Dropbox

#215
post #182

Earlier quoted context omitted.

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…

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!"

Re: Congrats Dropbox

#216

Earlier quoted context omitted.

Wouldn't that be the best time to go public? Before valuations drop? Usually you don't want to sell your stock to the public after it's crashed.

Sure, we call it pump and dump. Awesome for insiders but terrible for investors. I'm talking from an investor perspective. By going public today it might only benefit a few early birds such as founders, angels, founding team, etc. If the market crashes it's terrible for new investors, anyone who bought the IPO. If you IPO after a storm your stock can only go up from the bottom.

That's not what pump and dump means.

Re: Congrats Dropbox

#217

Remember when people used two floppy disks to save files so if one floppy break you have a backup one? I remember the first day I heard about Dropbox and I was amazed by it, it made perfect sense. Since then I'm a client and as an entrepreneur, it's a company I always looked up to.

I definitely remember "oh no, I think the floppy is corrupted" as a popular excuse when it was essay hand in day at college

Re: Congrats Dropbox

#218
post #29

Incidentally, Drew's relationship with the HN community is even older than his relationship with Y Combinator. Two weeks before we interviewed Drew and Arash, Drew posted Dropbox to HN: https://news.ycombinator.com/item?id=8863

[deleted]

Re: Congrats Dropbox

#219
post #207

Am I correct that if there were stock options granted to the first employees of Dropbox in 2007 then they expired in 2017?

There were several opportunities for liquidity for people with options prior to this point (not to mention extremely early employees should have had an extremely low strike price and should have been able to afford exercising prior to this point with relatively little risk)

I was at Dropbox from 2012 to 2016 and (while I'll lose out, relatively speaking, on taxes due to having a lot in RSUs, and I've mentioned on HN before being frustrated with the illiquidity of RSUs) people in my employee "cohort" should be fine as well.

Re: Congrats Dropbox

#220
post #76
post #73

I remember seeing the release of DB on HN and immediately had a "holy shit" moment, I was literally carrying a portable shuttle computer back and forth to the office before DropBox - congrats to the entire team and thank you for a product I've used daily for 10+ years! And this is yet another good lesson for would be angel investors AND startup employees - DropBox to me was one of the most obvious product-market-fit…

Is there any talk about how late stage employees have done? I suppose they’ll be in the waiting game as their lockup progresses.

Stock is up beyond the last valuation in 2014. Assuming the stock holds its value for he 6 month lockup, they'll get at least what they signed up for.
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