Dropbox CEO Drew Houston to step down • Hacker News Board

Re: Dropbox CEO Drew Houston to step down

#271

Post by RigelKentaurus » Tue, May 26, 2026, 9:54 PM UTC

They had a terrific product that worked well in ~2013, but they haven't innovated since then (TBH, not sure what "innovation" means in the file-sync space.) Although Y-o-Y revenue is mostly flat, I'm a little surprised that they still brought in $630M the last quarter, and that they still have 2,000 employees. Looking at what Dropbox does, I would have guesstimated they were a 250-person company.

All the best to their employees, but I think a big round of layoffs will be coming within the next couple of quarters.

Re: Dropbox CEO Drew Houston to step down

#272

Post by light_triad » Tue, May 26, 2026, 9:55 PM UTC

ktallett wrote: post #240

light_triad wrote: post #206

Earlier quoted context omitted.

It's a great product. They had the brand, the capital, and the user base to become what Slack, Zoom, or Notion became. Instead, they spent a decade fighting a losing battle over storage pricing with Google and Microsoft. Their lack of a second act is due to a failure of product vision and enterprise execution.

I don't see the need to become bloated like slack and a one size fits all application. They do a great job with the product they have. Is there anything wrong with just being what you are? Why does the lack of a second act need to be a bad thing if your first product is great and still extremely valuable? I would also if anything put Zoom in with Dropbox, they have a product that is by far the most enjoyable to use i…

[dead]

Re: Dropbox CEO Drew Houston to step down

#273

Post by afavour » Tue, May 26, 2026, 9:56 PM UTC

light_triad wrote: post #206

nashadelic wrote: post #199

Earlier quoted context omitted.

Dropbox is a $6B product, just no second act

It's a great product. They had the brand, the capital, and the user base to become what Slack, Zoom, or Notion became. Instead, they spent a decade fighting a losing battle over storage pricing with Google and Microsoft. Their lack of a second act is due to a failure of product vision and enterprise execution.

> They had the brand, the capital, and the user base to become what Slack, Zoom, or Notion became. Instead, they spent a decade fighting a losing battle over storage pricing with Google and Microsoft

Is the alternative not likely that they would have spent a decade fighting a losing battle over office software with Google and Microsoft? Paper was a great product but the big guys have vertical integration so companies prefer their end-to-end solutions (GSuite etc) and I don't see how Dropbox could have easily overcome that.

Re: Dropbox CEO Drew Houston to step down

#274

Post by dzonga » Tue, May 26, 2026, 9:57 PM UTC

genxy wrote: post #148

bhouston wrote: post #124

Dropbox's stock has been stuck at around $6B valuation for years with flat growth and income around $2.5B per year. It is just stuck. Box.com, which is quite similar, is not that different. Around $3B and $1.2B in income. Similar valuation. I think it is the market, not the leadership. It is a tough market that has cut off the consumer end because all the big players have their own deeply integrated solutions: Apple…

iCloud is just rebadged GCS.

iCloud actually runs on FoundationDB - probably one of most underrated DB engines out there.

you can build object storage on FoundationDB + other awesome bespoke stuff.

Re: Dropbox CEO Drew Houston to step down

#275

Post by idiotsecant » Tue, May 26, 2026, 9:58 PM UTC

mplewis wrote: post #259

idiotsecant wrote: post #248

Earlier quoted context omitted.

I think impending demographic collapse might give us a peek at that sooner than you'd think

Clarify exactly what you mean by "demographic collapse."

https://en.wikipedia.org/wiki/Population_decline

Re: Dropbox CEO Drew Houston to step down

#276

Post by mandeepj » Tue, May 26, 2026, 9:58 PM UTC

bhouston wrote: post #124

Dropbox's stock has been stuck at around $6B valuation for years with flat growth and income around $2.5B per year. It is just stuck. Box.com, which is quite similar, is not that different. Around $3B and $1.2B in income. Similar valuation. I think it is the market, not the leadership. It is a tough market that has cut off the consumer end because all the big players have their own deeply integrated solutions: Apple…

> I honestly do not know where to go.

Yeah, with blinders on, it's hard to see that. Otherwise, the playground was wide open. If whales start eating your revenue, then you go after them.

Re: Dropbox CEO Drew Houston to step down

#277

Post by dzonga » Tue, May 26, 2026, 9:59 PM UTC

my take dhouston should go be a CTO somewhere.

technically he's rich enough to never work again. but he's hungry, young & smart

& can really push the industry forward - by taking one of the f500 that's tech adjacent & be CTO

Re: Dropbox CEO Drew Houston to step down

#278

Post by RigelKentaurus » Tue, May 26, 2026, 10:00 PM UTC

guhcampos wrote: post #226

bhouston wrote: post #124

Dropbox's stock has been stuck at around $6B valuation for years with flat growth and income around $2.5B per year. It is just stuck. Box.com, which is quite similar, is not that different. Around $3B and $1.2B in income. Similar valuation. I think it is the market, not the leadership. It is a tough market that has cut off the consumer end because all the big players have their own deeply integrated solutions: Apple…

Is that bad though? Think about it. If you're paying all your bills, all your wages, and you have a strong product that people enjoy, and you're able to compete in the market - maybe not gaining any ground, but at least not losing any either - why change? Of course I moderately understand the market pressures at work, but at some point in the human civilization journey we'll have to be content with something instead…

It's not necessarily bad, but in tech, not actively growing is tantamount to shrinking. Organic customer churn and attrition means that you're just a few years away from irrelevance. If DBX wants to stay a stable tech company, it should figure out a way to go private.

Re: Dropbox CEO Drew Houston to step down

#279

Post by jlarks32 » Tue, May 26, 2026, 10:02 PM UTC

I was lucky enough to work at Dropbox for a bit. Awesome engineering culture and such good people. Got to even grab a beer and rip karaoke with Drew. Thanks for creating such an awesome working environment Drew. I cannot say thank you enough for those memories or that experience. By far the best CEO and leader I've seen.

Re: Dropbox CEO Drew Houston to step down

#280

Post by lancewiggs » Tue, May 26, 2026, 10:05 PM UTC

bhouston wrote: post #124

Dropbox's stock has been stuck at around $6B valuation for years with flat growth and income around $2.5B per year. It is just stuck. Box.com, which is quite similar, is not that different. Around $3B and $1.2B in income. Similar valuation. I think it is the market, not the leadership. It is a tough market that has cut off the consumer end because all the big players have their own deeply integrated solutions: Apple…

Perhaps think of the stock as a value stock, not a growth/momentum stock.

The thesis is that they should survive and thrive as an investment asset through the AI bust, but performance during the AI bubble is poor. If you are a longer term investor then B2B SaaS valuations appear cheap right now, but you need to be able to weather the storm of missing out on the AI infused bubble.

As evidence the BVP Nasdaq Emerging Cloud Index is at all-time lows for EV/revenue multiples. While some of the companies will see growth rates impacted by AI, that only explains a little bit of the drop in multiples versus the past.