Newsletter MAY 2026

Hi there, The tension between SaaS and AI remains at its peak. Many software developers now believe they can build almost any application using AI, open-source libraries, and vibe-coding tools — regardless of complexity. Later this year, we may hear many success stories… or we may learn otherwise. At one extreme, SaaS companies could start losing subscribers as businesses leverage AI to build their own custom applications, while vibe-coding platforms emerge as the next generation of unicorns. On the other side of the spectrum: maybe not so fast. Building software is one thing. Building scalable, secure, reliable, and continuously evolving software platforms is something else entirely. Hope you enjoy this month's episodes.  As always, listen on Spotify or Apple, or watch them on YouTube. Building AI Pricing Dan returns to the podcast to unpack why adding AI doesn’t automatically create more value—and why most companies should expect to get AI pricing wrong at first. He also shares why token-based pricing can hurt your GTM motion, plus the common pricing mistakes teams should avoid. BONUS CONTENT I asked Dan about a business decision that proved valuable in hindsight, he pointed to starting his consulting firm before he felt fully ready. His takeaway: there will always be reasons why now isn’t the right time, but sometimes the best decisions require ignoring that voice and taking the leap anyway. LISTEN NOW Three Ways to Manage AI Use in Organizations Uri joins the podcast to discuss how AI is blurring the lines with SaaS, shifting users away from traditional UIs and toward AI agents. He also shares why centralized AI and SaaS governance is becoming harder for enterprises, especially as non-human identities continue to grow. BONUS CONTENT When asked about a surprisingly positive business decision, Uri pointed back to starting his first company nearly 20 years ago. Though others saw it as risky, he says taking that leap became the best decision of his career—and one that led him to keep building, now through his third company. LISTEN NOW Books Behind the Leaders: Recommendations from our Guests I always ask our guests to recommend a book, or perhaps a blog or podcast, that has been helpful in their lives—professionally or personally. Check out what our recent guests have recommended. SEE ALL RECOMMENDATIONS Qrvey, 1775 Tysons Blvd, 5th Floor, Tysons, VA 22102, United States