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Candid conversations with founders and execs about making critical decisions, building and aligning your team, and showing up at your best.
I’m Keith Cowing, an executive coach and founder. Every week I’m in the room with leaders facing their hardest problems. This is where I share what I learn.
| Episode | Date |
|---|---|
|
How Top AI CEOs Hire Their Executive Teams | Michael Cullen, Founder of Bleecker Street
|
Oct 21, 2026 |
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The Discipline to Keep Showing Up | Dre Baldwin on Executive Presence and Consistency
|
Oct 06, 2026 |
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Consensus Is Too Slow, Even With Two People | Mahesh Guruswamy, COO of Kajabi
|
Aug 20, 2026 |
|
Why 90% of AI Agents Are Stuck in a Pilot
|
Jul 01, 2026 |
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10 Rules for Building AI Agents That Actually Work
|
Apr 21, 2026 |
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The Truth About Hiring Your First Head of Product
|
Apr 07, 2026 |
|
Field Notes from 20 Years of NYC Startups
|
Jan 29, 2026 |
|
Why 50% of Startup Executive Hires Fail (and How to Fix It)
|
Dec 22, 2025 |
|
250 Board Meetings Later: This CEO’s playbook will change your board meetings forever
|
Nov 26, 2025 |
|
Mastering executive offsites
|
Nov 04, 2025 |
|
How to bring startup speed to big organizations
|
Oct 21, 2025 |
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From Trade Shows to Target’s Shelves: Growing 500% in a Year w/ Recoup Co-founder Siwat Siengsanaoh
|
Oct 09, 2025 |
|
From Burnout to Breakthrough: Master Your Calendar
|
Sep 15, 2025 |
|
From Silos to Studios: A New Playbook for Building Faster, Smarter Teams
|
Jul 23, 2025 |
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Driving Rapid Change Without Breaking Your Team: Mastering the Art of Cadence and Commitment
|
Jun 30, 2025 |
|
Don't Leave Your Moral Compass at Home with Natasha Jaffe
|
Jun 18, 2025 |
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From Ballet to Scalpel to CEO: Reinvention, Resilience & Hiring Unconventionally
|
Apr 30, 2025 |
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From Big Company to AI Startup: How Fast Execution Beats Perfect Planning with Uday Chakravarthi
|
Feb 27, 2025 |
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From the Mat to the Boardroom: Iron Mike Steadman on Grit, Branding & the Power of Action
|
Feb 06, 2025 |
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Incentives, Truth and Selling the Right Way with Wayne Morris
|
Dec 19, 2024 |
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How to Lead From Growth Stage to IPO with Nayya President and COO Sarah Liebel
|
Oct 21, 2024 |
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From Self-Taught Developer to CTO and Inspiring Leader with Danielle Leong
|
Sep 19, 2024 |
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From Open-Heart Surgery and Mom's Ginger Teas to Beverage Entrepreneur with Siwat Siengsanaoh
|
Sep 18, 2024 |