![[Un]Churned – The No. 1 Podcast for Customer Retention](https://d3t3ozftmdmh3i.cloudfront.net/staging/podcast_uploaded_nologo/40344000/40344000-1759325757098-ebbb3cde389fe.jpg)
Ex-Microsoft AI Lead: Why Smart Teams With Big Budgets Still Fail at AI ft. Brian Evergreen (The Future Solving Company)
[Un]Churned – The No. 1 Podcast for Customer RetentionShow Notes
Everyone's racing to "do AI." Almost nobody can say what for. Brian Evergreen, Forbes AI thought leader, author of Autonomous Transformation, ex-Microsoft, Founder & CEO of The Future Solving Company joins Josh Schachter to flip the playbook.
Start with a problem? That traps you in incrementalism. Be data-driven? There's no data about the future. The old industrial-era moves quietly sabotage every AI rollout.
Brian's fix: solve for a future you can feel. Then reverse-engineer it with one question: what would have to be true?
Inside: the reason-tree framework, the JFK moon test, and how to make renewal a panic-level no-brainer your champion fights for. You don't need the CEO's permission to start.
---
Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com.
---
What you'll learn - Why "start with a problem" caps your upside - How "data-driven" quietly became unscientific - Why green scorecards hide a shrinking business - The JFK test for a visceral vision - The reason-tree mapping "what would have to be true" - Whether a revenue number can be a vision - Helping customers build their own vision - Starting all this without executive buy-in
---
Timestamps 0:00 - Preview & Introduction 2:00 - Meet Brian Evergreen (Ex-Microsoft) 4:30 - Why the digital-era playbook fails for AI 5:25 - "Start with a problem" is an incrementalism trap 6:00 - How "data-driven" turned unscientific 7:19 - All green scorecards but shrinking market share 8:40 - Netflix solved the same future twice 9:35 - No value vision? Don't invest in AI yet 12:40 - Getting over organizational inertia 15:30 - The reason-tree: "what would have to be true?" 18:25 - Can a vision be a number? (Replit's $1B ARR vision) 19:50 - Why most "strategy" is just a SWOT board 21:15 - You don't need the CEO's permission
---
Josh is writing a book on building customer relationships. Follow his journey and insights at www.joshschachter.com
---
Where to Find the Guest Brian Evergreen: https://www.linkedin.com/in/brianevergreen/ Brian's Substack: https://newsletter.brianevergreen.com/
--- Where to Find Josh: LinkedIn: https://www.linkedin.com/in/jschachter/ Unchurned Substack: https://unchurned.substack.com/
More from [Un]Churned – The No. 1 Podcast for Customer Retention
Is AI still an experiment on your customer success team, or is it delivering results?
Most companies treat renewals as a sales function. The real shift is treating retention as a job for the whole company.
Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com.
Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com.
Most companies think of customer success as a support function that ships software. The real shift is treating it as a co-build practice that ships outcomes.