Box is an amazing company. It is at $600m-ish ARR and $800m annualized bookings, and cash-flow positive. Amazing. Truly.



  • Dropbox is >2x larger by revenue, at ~$1.3b in ARR vs. $500m for Box. Both are huge success stories. But more revenue, all things being equal, makes for a higher market cap.
  • Dropbox has stronger cashflow.
  • Dropbox is growing more quickly, adjusting for ARR. Dropbox is quantitatively growing at about the same rate as Box (both at ~28% Year-over-Year), but Dropbox is at $1.3b+ in ARR vs Box is at $500m in ARR. So normalized for scale, Dropbox is growing “faster”. Put differently, at $500m in ARR Dropbox was growing faster than Box is today, and almost all software companies see their growth slow down over time.

So, Dropbox should be worth more.

Both are great companies, serving different customers. Dropbox is much more B2C-like in metrics (and at a product level). It has higher churn, but much lower customer acquisition costs. Box is much more enterprise, and as a result, has much higher revenue retention, but also much higher sales and marketing costs. It’s not as direct a competition as the names and history make it out to be.

Box will grow into Dropbox’s valuation as it crosses $1b-$2b+ in ARR.

Box will be there before you know it.

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