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5 Interesting Learnings from Circle at $2.3 Billion in “ARR”

SaaStr

✨ Lemkin (@jasonlk) June 5, 2025 5 Interesting Learnings for B2B and SaaS Founders from Circle’s IPO: 1. The “Regulatory Moat” Strategy: Compliance as a Competitive Advantage Circle was the first to receive a New York State BitLicense, which is famously difficult to obtain, in 2015. Compliance debt is real debt.

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The Great IPO Awakening: What 2025’s Surprisingly Hot Market Means for B2B Companies

SaaStr

After years of drought, 2025 has delivered a scorching hot public market for tech companies so far, with some eye-popping returns that should have every SaaS founder and investor paying attention. This “pricing power” indicates genuine demand, not just investment bank optimism. The most recent five IPOs are averaging 121.5%

B2B
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The Top 3 Reasons AI Sales Tools “Don’t Work” (Spoiler: They Actually Do)

SaaStr

✨ Lemkin (@jasonlk) June 16, 2025 The Top 3 Reasons AI Sales Tools “Don’t Work” (Spoiler: They Actually Do, If You Use The Tools Properly) I get this question at least 3x a week: “Jason, we tried AI sales tools and they just don’t work. ✨ Lemkin (@jasonlk) June 12, 2025 #3. You Want Them to Do Everything.

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Welcome Back Duplo Cloud & Pylon to SaaStr Annual 2026! 🎉

SaaStr

Their return demonstrates their continued investment in the SaaS ecosystem and commitment to helping founders succeed. See you at SaaStr Annual + AI Summit 2026 and SaaStr AI London in December 2025! Pylon – Welcome Back for Round Two! 🚀 We’re equally excited to welcome back Pylon as a 2nd-time sponsor of SaaStr Annual!

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The $939B Question: Is AI Eating SaaS or Feeding It?

SaaStr

The Great Spending Showdown: AI vs SaaS in 2025/2026 — What Every B2B Leader Needs to Know We’re witnessing the most dramatic shift in enterprise tech spending since the cloud migration began 15 years ago. The numbers are staggering: AI spending is set to hit $644 billion in 2025, growing at a mind-bending 76.4% year-over-year.

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Is AI Penetration … Slowing Down? Ramp Says Possibly

SaaStr

as of April 2025, the growth trajectory has flattened since late 2024. I pay more for AI subscriptions than I do for my car lease — Matthew Berman (@MatthewBerman) June 5, 2025 Why the Slowdown May Be Real Several structural factors suggest this isn’t just a temporary pause: Implementation complexity has caught up with enthusiasm.

AI
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Palantir’s +79% vs Bill’s -43%: The AI Divide That Defined SaaS Performance in 1H’25

SaaStr

SaaS / B2B Public Stock Performance 1H’25: Top Winners & Losers 📊 Market Summary: SaaS Sector in 1H’25 The SaaS sector experienced a dramatic bifurcation in the first half of 2025, with clear winners and losers emerging based on AI differentiation, security positioning, and vertical specialization.

AI