Chris Walker (CEO of Passetto) joins Ross to talk about personal transformation, scaling through delegation, and why most entrepreneurs are chasing the wrong kind of freedom.
Chris shares insights from his month-long sabbatical, including frameworks for creating true independence—beyond just financial freedom—and lessons learned about leadership, agency structure, and internal alignment.
Ross and Chris also unpack strategies for delegation, avoiding burnout, client selection, the evolving role of SEO, and how B2B companies should rethink go-to-market in a post-ChatGPT world.
Show Notes:
00:00 – Welcome Chris Walker & “The Collision of Worlds”
00:51 – Why Bigger Doesn’t Mean Better
02:05 – The Real Test: Can Your Business Run Without You?
03:09 – 10 Types of Freedom (Beyond Just Financial)
06:01 – Time, Social, Creative, Mission, Health & More
09:10 – Letting Go of the Clients That Drain You
13:07 – Freedom Through Delegation: Fake vs Real
15:05 – Why Firing Someone Might Set Them Free
17:20 – Rethinking Wealth: Why 2x More Money Won’t Make You Happy
20:00 – Breaking Mental Loops Around Growth, Suffering, and “Success”
22:50 – Why Resistance Means You’re Out of Alignment
26:00 – Layoffs, Misalignment, and Making the Hard Call
29:00 – A New Agency Playbook: 10 People, $10M
31:32 – Delegation as a Superpower (And Trap)
34:20 – Hiring Without Job Descriptions
37:00 – How Top Talent Finds You (Not the Other Way Around)
39:01 – From Fake Delegation to Freedom Frameworks
41:00 – Pattern-Matching LinkedIn Content for Real ICP Impact
43:13 – SEO Today: Outdated, Unpersonalized & Being Replaced
46:50 – Why ChatGPT over Google for User Intent
48:10 – The Case for Diversified GTM (and SEO’s Narrow Role)
50:00 – Reframing Search: It’s Not Just Google Anymore
52:20 – Personal Holdings Companies & Managing Partners
54:00 – Why Resume-Perfect Execs Often Underperform
56:00 – Agency Scale: Founder as Visionary, Not CEO
59:00 – Building the Business That Serves Your Life
Show Links:
Chris Walker on LinkedIn
Chris’s Company, Passetto:
Listen on iTunes
Listen on Spotify
