Why Startups Fail—and How AI Can Help Them Succeed with Donna Mitchell & Douglas Squirrel

How can better conversations supercharge your tech team—and what happens when AI goes rogue? On this episode of Pivoting To Web3, Douglas Squirrel, an industry veteran who’s transformed over 400 technology teams worldwide. Squirrel shares the surprising truth behind thriving tech cultures, why fear and trust matter more than deadlines, and what companies get wrong about adopting AI tools. Plus, hear jaw-dropping real-world stories (bacon ice cream, anyone?) and actionable tips for keeping your AI agents “backstage.” If you’re a leader navigating AI, blockchain, or digital transformation, this is the practical, insightful discussion you can’t afford to miss! Podcast Hook: Ever heard of a team so efficient the boss had to fire their own CTO—over and over? Discover Douglas Squirrel’s wild journey from “nicest layoffs ever” to revolutionizing how tech teams and businesses communicate for insane profit. But that’s just the start: Find out why unleashing AI agents without a leash could land your company in a world of weird—and risky—surprises. Tune in now to laugh, learn, and rethink what it really takes to lead in the era of Web3 and AI! 💡 What you’ll learn in this episode: 1. Why so many startups fail at execution (and the fix) 2. The mindset shift leaders need to thrive in the AI era 3. How to align people, processes, and technology for growth 4. Real examples of AI + human collaboration in business If you want to thrive in the age of AI and Web3, this episode is for you! Chapters: 0:00 Fired for Success 04:58 "Action Science: Building Trust in Tech" 06:38 Rapid Iterative Learning in Tech 12:57 Manage New AI Like Interns 15:19 McDonald's AI Drive-Thru Fail 18:33 Phishing Defense: Secret Password Strategy 21:13 "Removing Key Blockers Breaks Dams" 23:53 "Test-Driven Communication Approach" 28:17 Engineers Experience Trading Floor Chaos 30:40 Shift Focus from Tech to Profit 33:01 AI and Ethical Governance Concerns