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The Tough Side of Being Venture Backed: ActOn Sells for $53m After 17 Years … And Raising ~$53m+

SaaStr

Founded 2008 * Raises ~$53m in VC * Sells 17 years later for $53m * Only $20m of that cash * 2x ARR price * 1x What Raised Just plain tough.

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AI Agents in B2B: Top 10 Learnings from Aaron Levie, CEO of Box and IBM’s VP of AI

SaaStr

While pitching cloud to banks in 2008-2009 was a “non-starter,” today there isn’t an enterprise that doesn’t already have an AI strategy in development. “It’s going 1000x faster than cloud adoption because everyone’s using it,” Datta noted.

AI 212
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The Early Days: How Veeva Hit $100m ARR With Just $3m Raised — And a Deep Vertical Focus

SaaStr

” The Numbers Behind the Discipline: 2008 : $4M Series A from Emergence Capital (300x return, reportedly returned entire fund 7x over) 2012 : $18.8M .” Despite investor pressure to “spend more, spend more, spend more,” Peter refused: “I was the guy who just didn’t get it. I was too conservative.

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How to Successfully Bring AI Products to Market at Scale with GitHub’s CRO

SaaStr

GitHub, founded in 2008, is a leading platform for software development and version control that has made waves since 2018 with its AI Copilot.

Scale 261
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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 ! Phase 3 of Dropbox: “We are evolving from traditional file sync and share to AI-powered universal search and content intelligence.”

AI Search 167
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AI Adoption: 5 Hard Truths About the Fastest Technology Transformation in History With Aaron Levie, CEO Box

SaaStr

Enterprise AI Adoption Is Moving 5-10X Faster Than Cloud The contrast with cloud adoption is striking, according to Levie: Cloud in 2008-2009 : “Try pitching the cloud to a bank. .” This generational shift will accelerate transformation far beyond what we saw with cloud adoption. That was a non-starter.

AI 211
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The Real Story Behind B2B SaaS Growth Today: What Maxio’s Data from 2,400+ Private Companies Tell Us

SaaStr

We’re seeing echoes of 2008-2009, where nimble startups thrived during the downturn. The money’s still there – it’s just more concentrated. Small Companies Are The Surprise Winners Here’s something counterintuitive: sub-$1M ARR companies are actually accelerating right now.

B2B 239