From Content Engine to Freedom Engine w/ Chris Walker

Content and Conversation: Organic Growth Insights from Siege Media

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Fake Delegation to Freedom Frameworks 41:00 – Pattern-Matching LinkedIn Content for Real ICP Impact 43:13 – SEO Today: Outdated, Unpersonalized & Being Replaced 46:50 – Why ChatGPT over Google for User Intent 48:10 – The Case for Diversified GTM (and SEO’s Narrow Role) 50:00 – Reframing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 Subscribe for weekly episodes: https://bit.ly/3dBM61f Listen on iTunes: https://podcasts.apple.com/us/podcast/content-and-conversation-seo-tips-from-siege-media/id1289467174 Listen on Spotify: https://open.spotify.com/show/1kiaFGXO5UcT2qXVRuXjsM Follow Ross on Twitter: https://twitter.com/rosshudgens Follow Siege Media on Twitter: https://twitter.com/siegemedia Directed by Cara Brown: https://twitter.com/cararbrown Email Ross: [e-mail] #seo | #contentmarketingSubscribe today for weekly tips: https://bit.ly/3dBM61f Listen on iTunes: https://podcasts.apple.com/us/podcast/content-and-conversation-seo-tips-from-siege-media/id1289467174 Listen on Spotify: https://open.spotify.com/show/1kiaFGXO5UcT2qXVRuXjsM Listen on Google: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy5zaW1wbGVjYXN0LmNvbS9jT3NjUkdLeA Follow Siege on Twitter: http://twitter.com/siegemedia Follow Ross on Twitter: http://twitter.com/rosshudgens Directed by Cara Brown: https://twitter.com/cararbrown Email Ross: [e-mail] #seo | #contentmarketing