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.

00:00 – Welcome Chris Walker & “The Collision of Worlds”

00:51 – Why Bigger Doesn’t Mean Better (And Why Chris Took a Month Off)

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43:13 – SEO Today: Outdated, Unpersonalized & Being Replaced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

Chris Walker on LinkedIn: https://www.linkedin.com/in/chriswalker171

Chris’s Company, Passetto: https://www.passetto.com

Siege Media: https://www.siegemedia.com

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Directed by Cara Brown: https://twitter.com/cararbrown

Email Ross: [email protected]

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