Grateful Dead Lessons and Tribute

Dave shares business lessons from the Grateful Dead and a personal memory of 'Black Muddy River' for Bobby Weir.

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Dave Kellogg is a leading voice in enterprise software, SaaS metrics and go-to-market strategy. A four-time guest on AI and the Future of Work, Dave brings decades of hands-on experience inside SaaS companies to challenge how leaders think about growth, metrics, and execution. He is an Executive-in-Residence at Balderton Capital and the author of Kellblog. His perspective is shaped by years spent leading and advising software businesses from early stages through scale.

In this conversation, we discuss:

Why Dave argues that we are increasingly working for the algorithm, not the other way around, and how that shift shows up in SEO, productivity, and workplace behavior.
Why SaaS is not dying but is under real pressure, and how claims that companies can easily replace systems like Salesforce or Workday misunderstand how enterprise software actually works.
How AI changes jobs by pushing work up the value chain rather than simply eliminating roles, and why history suggests societies adapt faster than we expect.
Why trust becomes more valuable as AI floods the world with low-quality content, and how brands, creators, and leaders must earn credibility in an era of front-run information.
What the move from the Rule of 40 to the Rule of 60 signals about today’s market, and why many mid-scale SaaS companies now face uncomfortable strategic choices.
How venture capital is becoming more financialized, what that means for founders, and why AI may accelerate the shift toward larger funds, bigger bets, and fewer safety nets.

Episode Chapters

00:00 Why Dave Kellogg’s Annual SaaS Predictions Matter More Every Year

03:53 Working for the Algorithm, Not the Other Way Around

06:10 “Death of SaaS”: Why Enterprise Software Isn’t Going Away

08:56 Why Enterprise Software Is Built to Last

11:51 AI and Jobs: Why Work Disappears Differently Than We Expect

16:31 The New Jobs AI Creates and Why Humans Stay Essential at Work

19:22 Why Trust Becomes the Most Valuable Currency in an AI-Driven World

24:23 Why AI Forces Us to Rethink Trust, Media, and Credibility

27:57 Why the Rule of 60 Is Replacing the Rule of 40 for Startups in 2026

33:44 How Venture Capital Is Becoming a Financial Services Business

41:47 Why Silicon Valley’s New Willingness to Take Political Positions Surprised Many Founders