article thumbnail

5 Interesting Learnings From DropBox at $2.6 Billion in ARR

SaaStr

” Drew Houston has been CEO since Day 1 in 2008 and we’re super excited to have him speaking at 2025 SaaStr Annual, May 13-15 in SF Bay ! File Sharing Moving More and More to Mobile, So Offering a Lower Cost Edition There This is also leading to some pressure on ARPU. #8.

AI Search 175
article thumbnail

5 Interesting Learnings from Expensify at $140,000,000 in ARR

SaaStr

Expensify: Founded in 2008 … 13 years ago. It was born in the age of mobile, and from the moment it launched, everyone I knew started to use it to track their own expenses. A long, tenacious path to $100m ARR, and then … Boom!! * 60% growth in Year 13 at $140m+ ARR!! * 119% NRR from SMBs!! Super Profitable (35% EBITDA!!)

Scale 328
Insiders

Sign Up for our Newsletter

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

article thumbnail

Seeking a Distribution Advantage with AI

Tom Tunguz

In the last five major cycles (internet, social, mobile, cloud, web3), startups seized the new technologies of the era to create a distribution advantage. The iTunes store launch in 2008 enabled Uber. Great companies transform a technology innovation into a go-to-market advantage.

AI Search 218
article thumbnail

The 10x Feature is Real. At Least, for a While. What’s Yours?

SaaStr

2008: Cross-platform. We had basic mobile, Mac and Windows, whatever you wanted. As the web began to grow, just having Mobile Sign and Safari compatibility alone could win deals. “Do you want 80% of your customers to be able e-sign your contacts? We know this, because we sure were lacking a lot of other key features!

Scale 246
article thumbnail

The Disappearance of the Fundraising Demo

Tom Tunguz

The iPhone was just a year old and mobile hadn’t blossomed yet. The fundraising pitches of 2008 highlighted leading indicators of success: the product, the vision, the team. At that August Demo Day, each pitch lasted eight minutes. Without fail each featured a demonstration of the product. It was the height of the Web 2.0

Scale 189
article thumbnail

What does it take to raise capital, in SaaS, in 2016?

The Angel VC

With constantly rising table stakes and a fundraising environment that looks quite a bit less favorable than last year’s, I believe the bar is higher than in the last 18-24 months (although raising money is still much easier than it was in “Silicon Valley’s nuclear winter” in 2008 ). Update 1: Here's a mobile-friendly version of the napkin.]

SaaS 193
article thumbnail

The 10x Feature is Real. At Least, for a While. What’s Yours?

SaaStr

2008: Cross-platform. We had basic mobile, Mac and Windows, whatever you wanted. As the web began to grow, just having Mobile Sign and Safari compatibility alone could win deals. “Do you want 80% of your customers to be able e-sign your contacts? We know this, because we sure were lacking a lot of other key features!

Scale 216