Oct 21, 202627 min
Resumes mean less than ever. Here's what top AI CEOs hire for instead. Michael Cullen recruits executive teams for some of the fastest-moving AI companies in the world. We sat down in person at Kit Studios in New York...
business
Executives Unplugged
Hosted by Keith Cowing · business · EN
About this Podcast:
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 2x founder. Every week I’m in the room with leaders facing their hardest problems. This is where I share what I learn.
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Contact path
Verified email
Booking probability
30%
Guest openness
Selective
80/100
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What is Executives Unplugged about?
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 2x founder. Every week I’m in the room with leaders facing their hardest problems. This is where I share what I learn.
Who hosts Executives Unplugged?
Executives Unplugged is hosted by Keith Cowing. The show has published 23 episodes to date.
What has Executives Unplugged covered recently?
Recent episodes include "How Top AI CEOs Hire Their Executive Teams | Michael Cullen, Founder of Bleecker Street" (21 October 2026, 27 minutes), "The Discipline to Keep Showing Up | Dre Baldwin on Executive Presence and Consistency" (6 October 2026, 41 minutes), and "Consensus Is Too Slow, Even With Two People | Mahesh Guruswamy, COO of Kajabi" (20 August 2026, 42 minutes).
How often does Executives Unplugged publish?
Executives Unplugged publishes roughly monthly, with episodes averaging 32 minutes across 23 episodes.
How hard is it to get booked on Executives Unplugged?
Booking probability for Executives Unplugged is 30%, and the host is rated Selective on guests. Executives Unplugged requires a Pod Score of 80 or higher. Executives Unplugged's contact route on record: verified email.
Who should pitch Executives Unplugged?
The strongest fits for Executives Unplugged are Business & Management Consulting. Executives Unplugged has a business audience.
About the host
Keith Cowing hosts Executives Unplugged, a business podcast with 23 episodes published.
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Recent episodes
Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.
Episode #22
The Discipline to Keep Showing Up | Dre Baldwin on Executive Presence and Consistency
Oct 6, 202641 minIn today's world, how you show up is more important than ever. Dre Baldwin started playing basketball at 14, came out of a Division III school and willed himself into a nine-year professional basketball career. He now...
Episode #21
Consensus Is Too Slow, Even With Two People | Mahesh Guruswamy, COO of Kajabi
Aug 20, 202642 minTeams don't swirl because they disagree, they swirl because nobody is empowered to end the debate and move. Mahesh Guruswamy runs product, engineering, and customer support at Kajabi as a single-threaded leader, a model...
Episode #20
Why 90% of AI Agents Are Stuck in a Pilot
Jul 1, 202632 minThe hardest part of an AI transformation has nothing to do with the tech. It's breaking the human silos and learning to manage your agents like employees. Akshit Kandi has mentored over 100 startups and built agents...
Episode #19
10 Rules for Building AI Agents That Actually Work
Apr 21, 202619 minI've spent the last year building AI agents and working with CEOs doing the same. Most of what I built, I threw out. Here are the 10 rules that survived. I've been building agents across my coaching practice, content...
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Episode #18
The Truth About Hiring Your First Head of Product
Apr 7, 202628 minThree top executive recruiters and Foursquare founder Dennis Crowley reveal why the candidate with the perfect resume is usually the wrong hire — and how to find the right one. Most CEO-CPO relationships fail within the...
Episode #17
Field Notes from 20 Years of NYC Startups
Jan 29, 202634 minWhat if AI made you more present , not more addicted? Dennis Crowley (founder of Foursquare) shares field-tested lessons from 20+ years building in NYC, why he prefers NYC to SF, and the thesis behind Hopscotch Labs and...
Episode #16
Why 50% of Startup Executive Hires Fail (and How to Fix It)
Dec 22, 202528 minOver half of startup executive hires fail in the first 18 months and many in the first 30 days. Executive hiring is a high-stakes gamble. One bad fit doesn't just cost money; it can derail your entire momentum and kill...
Episode #15
250 Board Meetings Later: This CEO’s playbook will change your board meetings forever
Nov 26, 202530 minMatt Blumberg reveals why he bans slides, forces independent directors to audition for a seat, and uses AI to simulate Steve Jobs in the boardroom. For many founders, the board meeting is a dreaded time sink full of...
Episode #14
Mastering executive offsites
Nov 4, 202535 minToo many offsites miss the powerful opportunity to align a leadership team. Here’s how to make yours the exception. In this episode, Kelly Dwyer, executive coach and facilitator, breaks down what separates...
Episode #13
How to bring startup speed to big organizations
Oct 21, 202539 minA startup founder joins a 10,000-person company to build AI from scratch and learns how to move fast without losing trust. Moving fast inside a big company can feel impossible. You’re hired to shake things up - but if...
Episode #12
From Trade Shows to Target’s Shelves: Growing 500% in a Year with Recoup Co-founder Siwat Siengsanaoh
Oct 9, 202533 minIf you want 5x growth, you need more than a great product. In this episode, Recoup co-founder Siwat Siengsanaoh breaks down how trade shows, advisory boards, and fast feedback loops turned ginger-forward beverages into...
Episode #11
From Burnout to Breakthrough: Master Your Calendar
Sep 15, 202514 minFeeling like your calendar is running your life? In this episode of Executives Unplugged, executive coach Keith Cowing shares a battle-tested playbook to flip the script. Learn how to audit your schedule, spot...
Episode #10
From Silos to Studios: A New Playbook for Building Faster, Smarter Teams
Jul 23, 202546 minYour org chart is obsolete. It's time to move from silos to studios. The old model of large, hyper-specialized teams is now a liability. If you're looking to leverage AI to innovate faster than the competition, this...
Episode #9
Driving Rapid Change Without Breaking Your Team: Mastering the Art of Cadence and Commitment
Jun 30, 202531 minThe pressure on leaders to deliver rapid, transformative change has never been higher. But how do you move fast without leaving your people behind? In this episode, host Keith Cowing sits down with Perry Steinberg, a...
Episode #8
Don't Leave Your Moral Compass at Home with Natasha Jaffe
Jun 18, 202526 minWhat do you do when a leader tells you, "You have integrity. That's rare in this profession"? For my guest Natasha Jaffe, it was the signal she needed to leave. In this episode of Executives Unplugged, I talk with...
Episode #7
From Ballet to Scalpel to CEO: Reinvention, Resilience & Hiring Unconventionally
Apr 30, 202527 minReady to ditch the resume buzzwords and hire for true potential? Struggling with your own career pivot or leading teams through change? Join Keith Cowing on Executives Unplugged with Dr. Susan Lovelle, a former...
Episode #6
From Big Company to AI Startup, a product, and revenue in 12 Months: How Fast Execution Beats Perfect Planning with Uday Chakravarthi
Feb 27, 202523 minIn this episode of Executives Unplugged , Keith Cowing sits down with Uday Chakravarthi, former head of product at Atlassian and current CEO of Clinch AGI, an agentic AI company revolutionizing how companies sell and...
Episode #5
From the Mat to the Boardroom: Iron Mike Steadman on Grit, Branding & the Power of Action
Feb 6, 202535 minWhat does it take to get back up when life knocks you down? In this episode of Executives Unplugged , Iron Mike Steadman - collegiate boxing champion, veteran, entrepreneur, and business coach - shares his journey from...
Episode #4
Incentives, Truth and Selling the Right Way with Wayne Morris
Dec 19, 202448 minIn this episode of Executives Unplugged, Keith sits down with Wayne Morris, founder of RVNU and seasoned Chief Revenue Officer for multiple Silicon Valley startups. Wayne shares his transformative insights on...
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