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The Investments Where I’m Going to Lose All My Money

So when I started writing venture checks in 2013, I didn't know what I was doing, but I had a strong start: First was Pipedrive co-leading seed, then acquired for $1.5B cash Second was Algolia leading U.S. seed, now at $200m+ ARR and an IPO candidate Third was...

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Artificial Intelligence (AI), Blog Posts, SaaStr.Ai

Tired vs. Wired: $4 Trillion in IPOs Coming, $100B in M&A, Vibing Isn’t Killing Salesforce After All, and Why the B2B Doomers Were Dead Wrong (Mostly)

I put this chart together for my SaaStr AI Annual opener last week. Of the 5 things we kept hearing through 2025 and through Q1 2026, and what we’re actually seeing now that the agents have shipped and the budgets have hit. #1. “Everyone will vibe-code their own CRM” → “Our CRM brings in deals…
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Aaron LevieCEO and Co-Founder of Box

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Eric YuanCEO & Co-Founder of Zoom

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Lew CirneCEO of NewRelic

"SaaStr is the undisputed thought leader in how to build SaaS businesses. Jason is legendary."

Lew CirneCEO of NewRelic

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Scott DorseyCEO of ExactTarget

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Aaron LevieCEO and Co-Founder of Box

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Phil FernandezCEO & Co-Founder of Marketo

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