Episodes 18
Avg. Duration 33m
Activity Highly Active
Since Sep 2024
Latest Episode Apr 2026

Publishing Details

Schedule
Monthly
Format
Episodic
Consistency
47%
Hosting
rss.buzzsprout.com

Contact & Outreach

About This Podcast

Top CEOs have coaches behind the scenes.

Executives Unplugged takes you into those rooms for candid conversations with leaders about how they find clarity in the chaos. We distill the systems and mindsets required to navigate high-stakes decisions and build world-class companies.

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Recent Episodes

The Truth About Hiring Your First Head of Product

Apr 07, 2026 27m Transcript

Three 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…

Field Notes from 20 Years of NYC Startups

Jan 29, 2026 33m

What 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…

Why 50% of Startup Executive Hires Fail (and How to Fix It)

Dec 22, 2025 28m

Over 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…

250 Board Meetings Later: This CEO’s playbook will change your board meetings forever

Nov 26, 2025 30m

Matt 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…

Mastering executive offsites

Nov 04, 2025 34m

Too 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…

How to bring startup speed to big organizations

Oct 21, 2025 39m

A 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…

From Trade Shows to Target’s Shelves: Growing 500% in a Year with Recoup Co-founder Siwat Siengsanaoh

Oct 09, 2025 33m

If 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…

From Burnout to Breakthrough: Master Your Calendar

Sep 15, 2025 13m

Feeling 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…

From Silos to Studios: A New Playbook for Building Faster, Smarter Teams

Jul 23, 2025 45m

Your 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…

Driving Rapid Change Without Breaking Your Team: Mastering the Art of Cadence and Commitment

Jun 30, 2025 31m

The 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…

Don't Leave Your Moral Compass at Home with Natasha Jaffe

Jun 18, 2025 25m

What 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…

From Ballet to Scalpel to CEO: Reinvention, Resilience & Hiring Unconventionally

Apr 30, 2025 26m

Ready 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…

From Big Company to AI Startup, a product, and revenue in 12 Months: How Fast Execution Beats Perfect Planning with Uday Chakravarthi

Feb 27, 2025 23m

In 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…

From the Mat to the Boardroom: Iron Mike Steadman on Grit, Branding & the Power of Action

Feb 06, 2025 35m

What 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 -…

Incentives, Truth and Selling the Right Way with Wayne Morris

Dec 19, 2024 47m

In 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…

How to Lead From Growth Stage to IPO with Nayya President and COO Sarah Liebel

Oct 21, 2024 36m

Join us for a candid conversation with Sarah Liebel, President and COO of Nayya, who shares her invaluable insights on maintaining a founder's mindset while empowering teams. Learn about the art of…

From Self-Taught Developer to CTO and Inspiring Leader with Danielle Leong

Sep 19, 2024 38m

Join us as Danielle Leong shares her inspiring journey from marketing to becoming Twilio's first female engineer and on to senior leadership roles at companies such as Github and FireHydrant.…

From Open-Heart Surgery and Mom's Ginger Teas to Beverage Entrepreneur with Siwat Siengsanaoh

Sep 18, 2024 27m

From open heart surgery and Mom's ginger teas, to selling ginger-based beverages in grocery stores across the country, Siwat's story is one of passion and resilience. The episode delves into pivotal…

Frequently Asked Questions

How many episodes does Executives Unplugged have?

Executives Unplugged has published 18 episodes since September 2024, covering topics in Business, Entrepreneurship.

Is Executives Unplugged still active?

Executives Unplugged is currently highly active with new episodes monthly. Average episode length is 33m.

How do I contact Executives Unplugged for sponsorship or guest appearances?

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