Thinking Big: Strategy that scales. Mindset that multiplies.

Sean Osborn

sean@sean-osborn.com

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Booking Overview

Thinking Big is a practical, strategy-first show for founders and ambitious professionals, combining mindset frameworks with scalable execution tactics. It’s especially useful for guests who can translate business theory into repeatable systems and decision tools.

Metrics

Episodes: 155

Frequency: Weekly

Rating: 4.9/5.0

Estimated listeners: <1k

Gender skew: Male

Location: USA

Instagram: 3.8k followers

Contact Information

sean@sean-osborn.com

For verified host and producer emails, sign up to view.

Host

Sean Osborn - Host Sean Osborn helps ambitious professionals and founders reach their next level by exploring tools, tactics, mindset, and high-leverage systems that compound growth. He runs “council”/roundtable...

Booking Intelligence

Booking Requirements

very_high
Typical Credentials:  
High-profile entrepreneurs, founders, and well-known business strategists/sales leaders whose frameworks are recognized (e.g., major public figures in strategy, persuasion, negotiations, entrepreneurship).
Required Achievements:  
Known for a signature business/sales/strategy framework or model, Founder/operator visibility and track record in scaling businesses, Public recognition through books, widely cited methods, or major media presence

Recent Guest Discussions

Ethan Mollick - Risk Of Cutting Junior Work: Avoiding Liquidation Of Future Senior Talent When AI Removes Grunt Tasks.

Gino Wickman - Accountability Chart/org Redesign: Restructure Around Accountability/role Seats Before Automating; “poorly Designed Seats” Concept.

Elon Musk - AI And Automation: Unbundle Roles Into Outputs; Delete Obsolete Work Before Automation; Time-bound Decision-making.

Sam Altman - AI And Org Design: Whether AI Changes The Value Of A Role; Task Vs Job Framing; Decisions For Restructuring Teams.

Robert Cialdini - Persuasion Sequence: Reducing Uncertainty Before Increasing Urgency; Evidence/proof Before Pressure.

Recent Topics

Entrepreneurship, Sales, Scaling, Strategy, Operations

Episodes

Here's the recent few episodes on
Thinking Big: Strategy that scales. Mindset that multiplies.
:

AI Doesn't Replace People First. It Destroys Poorly Designed Seats First: Altman, Musk, Wickman, and Mollick Collide on the $80K Hire Question

June 08, 2026

Every founder is quietly doing this math right now. AI can produce what my $80K a year hire produces. So do I restructure the team, and when. A client brought me that question this week, and instead of giving you my take, I pulled The Council into the room and let the minds collide in front of you. This is the roundtable cut. Each mind speaks for itself, in its own voice, in the order it happened. The Sam Altman model said be careful with the premise: AI does tasks, not jobs, and the real t...

You Don't Have a Closing Problem. You Have a Truth Problem. (Five Sales Legends on Doubling Your Close Rate Without Feeling Salesy)

June 04, 2026

Here's the lie a full calendar tells you. It says you're winning. Then the calls don't close. Your team starts pushing harder. And every conversation starts to feel like you're talking someone into something. That feeling, the salesy feeling, is the thing nobody can quite fix. So I ran it through The Room. I convened five mind models who have spent their lives on this exact problem. Alex Hormozi reframed it first. A full calendar plus a terrible close rate is not a sales problem, it's a qu...

Don't Niche Down. Gate Up. (Four Legends, One Founder's Fear, and the Move That Protects Your Cash)

June 02, 2026

Here's the knot almost every founder hits. Things are working. Money is coming in. And then everyone around you starts chanting the same advice. Niche down. It sounds smart. It feels terrifying. Because the second you try it, it feels like you're about to fire the people funding your life. So I ran the question through The Room. I convened a council session inside Invisible Council AI with cognitive models of four people who have actually built fortunes on this exact decision. Alex Hormozi...

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