Executives Unplugged
Claim This Podcastby Keith Cowing
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Podcast Overview
<p>Top CEOs have <b>coaches behind the scenes</b>.</p><p></p><p><b>Executives Unplugged</b> takes you into those rooms for candid conversations with leaders about how they find <b>clarity in the chaos</b>. We distill the <b>systems and mindsets</b> required to navigate high-stakes decisions and build world-class companies.</p>
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Publishing Since
9/18/2024
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Recent Episodes
April 21, 2026
10 Rules for Building AI Agents That Actually Work
<p>I'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.</p><p></p><p>I've been building agents across my coaching practice, content production, and business operations — and the biggest lesson is that the hard part isn't the AI. It's codifying what actually matters in your work and organizing it so agents can use it. In this episode, I break down 10 rules for building agents that are genuinely useful — from structuring your data and building context that compounds, to choosing the right model for the right job, mixing deterministic software with LLMs, and managing agents the way you'd manage a high-performing team. No hype, no theory — just what I've learned from doing it every day. If you've been curious about agents but haven't started yet, this is your playbook.</p><p></p><p>Chapters</p><p>00:00 Introduction</p><p>00:44 Rule 1: Put All Your Data in One Place</p><p>02:00 Rule 2: Build Context That Compounds</p><p>03:28 Rule 3: Design for Rapidly Swapping Models</p><p>05:03 Rule 4: Use the Right Model for the Right Problem</p><p>06:55 Rule 5: Mix Deterministic Software with LLMs</p><p>08:21 Rule 6: Orchestrate Based on Frequency and Value</p><p>10:44 Rule 7: Keep Agents Narrowly Focused</p><p>12:04 Rule 8: Get Ready to Iterate</p><p>12:52 Rule 9: Managing Agents Is a New Skill</p><p>15:00 Rule 10: Half of What You Build Is Disposable</p><p>17:11 Your Next Steps: Just Start Building</p><p></p><p>Follow Keith Cowing on LinkedIn: <a rel="noopener noreferrer nofollow" href="https://linkedin.com/in/keithcowing" target="_blank">https://linkedin.com/in/keithcowing</a></p><p>Join the Inner Circle: <a rel="noopener noreferrer nofollow" href="https://execs.tv" target="_blank">https://execs.tv</a></p><p></p><p>Subscribe</p><p>YouTube: <a rel="noopener noreferrer nofollow" href="https://www.youtube.com/playlist?list=PLU_rgycqchjl1jNqjOeJFepyr9yfcXWcM" target="_blank">https://www.youtube.com/playlist?list=PLU_rgycqchjl1jNqjOeJFepyr9yfcXWcM</a></p><p>Spotify: <a rel="noopener noreferrer nofollow" href="https://open.spotify.com/show/1Bw7KhjlUzFjMoFhdfNAKN" target="_blank">https://open.spotify.com/show/1Bw7KhjlUzFjMoFhdfNAKN</a></p><p>Apple Podcasts: <a rel="noopener noreferrer nofollow" href="https://podcasts.apple.com/us/podcast/executives-unplugged/id1769131263" target="_blank">https://podcasts.apple.com/us/podcast/executives-unplugged/id1769131263</a></p>
April 7, 2026
The Truth About Hiring Your First Head of Product
<p>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.</p><p></p><p>Most CEO-CPO relationships fail within the first 18 months and a lot of that pain starts with how the hire was made in the first place.</p><p></p><p>In this episode, I sat down with three of the best executive recruiters in the business — Chris Running, Jodi Jefferson, and Michael Cullen — plus Dennis Crowley, founder of Foursquare and Hopscotch Labs, to unpack the biggest mistakes founders and CEOs make when hiring their first VP of Product or CPO at Series A through Series C companies.</p><p></p><p>We cover: why many searches derail, the logo trap that seduces hiring managers into picking the wrong candidate, why you should look for trajectory over altitude, the management answer that's a complete red flag, how AI fluency is reshaping what "great" looks like in a product leader, and what it actually takes to close top talent in a market that's shifting fast.</p><p></p><p>Whether you're a founder about to make this hire or a product leader evaluating your next opportunity, this episode gives you the playbook from both sides of the table.</p><p></p><p><b>Chapters</b></p><p>01:13 Start With Why</p><p>03:10 Avoid Logo Trap</p><p>04:28 Real Search Example</p><p>07:50 Trajectory Not Altitude</p><p>08:48 Assess Judgment & Speed</p><p>10:52 Culture Fit Walkthrough</p><p>12:28 Management In Details</p><p>13:59 AI Native Leaders</p><p>17:15 Hiring With Conviction</p><p>19:23 Candidate Due Diligence</p><p>20:48 Align Expectations</p><p>23:19 Close The Candidate</p><p>25:13 The Market Shift</p><p>26:14 Five Takeaways</p><p></p><p><b>Find the guests on LinkedIn:</b></p><p>Jodi Jefferson: <a rel="noopener noreferrer nofollow" href="https://www.linkedin.com/in/jodijefferson/" target="_blank">https://www.linkedin.com/in/jodijefferson/</a></p><p>Michael Cullen: <a rel="noopener noreferrer nofollow" href="https://www.linkedin.com/in/cullenmm/" target="_blank">https://www.linkedin.com/in/cullenmm/</a></p><p>Chris Running: <a rel="noopener noreferrer nofollow" href="https://www.linkedin.com/in/chris-running-a94a8025/" target="_blank">https://www.linkedin.com/in/chris-running-a94a8025/</a></p><p>Dennis Crowley: <a rel="noopener noreferrer nofollow" href="https://www.linkedin.com/in/dpstyles/" target="_blank">https://www.linkedin.com/in/dpstyles/</a></p><p></p>
January 29, 2026
Field Notes from 20 Years of NYC Startups
<p>What if AI made you more present<i>,</i> not more addicted?</p><p></p><p>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 Beebot: ambient, context-aware experiences designed to push you into the real world instead of into a feed. We also get tactical: notebooks, hiring, early-stage chaos, and how to stay in the game when you feel burned out.</p><p></p><h2><b>Chapters</b></h2><p>(00:00) Intro — A founder’s field notes from NYC</p><p>(03:05) Why writing things down changes your brain</p><p>(09:10) “You fall to the level of your systems”</p><p>(14:45) From Dodgeball → Foursquare → Hopscotch Labs</p><p>(19:35) BeeBot — proactive, wearable AI and why it’s hard</p><p>(27:15) Hiring for uncertainty: side projects, skill, and resilience</p><p>(34:30) NYC tech evolution — capital, talent, and density</p><p>(41:10) How to battle burnout</p><p></p><h2>Connect with Keith or Dennis</h2><p>Follow Dennis Crowley on LinkedIn: <a target="_blank" rel="noopener noreferrer nofollow" href="https://www.linkedin.com/in/dpstyles/">https://www.linkedin.com/in/dpstyles/</a></p><p>Follow Dennis Crowley on Substack: <a target="_blank" rel="noopener noreferrer nofollow" href="https://teendrama.substack.com/">https://teendrama.substack.com/</a></p><p>Hopscotch Labs: <a target="_blank" rel="noopener noreferrer nofollow" href="https://hopscotchlabs.co/">https://hopscotchlabs.co/</a></p><p>BeeBot: <a target="_blank" rel="noopener noreferrer nofollow" href="https://dens.medium.com/say-hello-to-dj-beebot-592cdc1f1704">https://dens.medium.com/say-hello-to-dj-beebot-592cdc1f1704</a></p><p>Follow Keith Cowing on LinkedIn: <a target="_blank" rel="noopener noreferrer nofollow" href="https://linkedin.com/in/keithcowing">https://linkedin.com/in/keithcowing</a></p><p>Join the Executives Unplugged Inner Circle for free coaching via email: <a target="_blank" rel="noopener noreferrer nofollow" href="https://execs.tv">https://execs.tv</a></p><p></p><p>Subscribe to the show:</p><p>YouTube: <a target="_blank" rel="noopener noreferrer nofollow" href="https://www.youtube.com/playlist?list=PLU_rgycqchjl1jNqjOeJFepyr9yfcXWcM">https://www.youtube.com/playlist?list=PLU_rgycqchjl1jNqjOeJFepyr9yfcXWcM</a></p><p>Spotify: <a target="_blank" rel="noopener noreferrer nofollow" href="https://open.spotify.com/show/1Bw7KhjlUzFjMoFhdfNAKN">https://open.spotify.com/show/1Bw7KhjlUzFjMoFhdfNAKN</a></p><p>Apple Podcasts: <a target="_blank" rel="noopener noreferrer nofollow" href="https://podcasts.apple.com/us/podcast/executives-unplugged/id1769131263">https://podcasts.apple.com/us/podcast/executives-unplugged/id1769131263</a></p>
19 total episodes available
Recent guests on Executives Unplugged
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Perry Steinberg
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Natasha Jaffe
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Wayne Morris
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- What is Executives Unplugged?
<p>Top CEOs have <b>coaches behind the scenes</b>.</p><p></p><p><b>Executives Unplugged</b> takes you into those rooms for candid conversations with leaders about how they find <b>clarity in the chaos</b>. We distill the <b>systems and mindsets</b> required to navigate high-stakes decisions and build world-class companies.</p> - How often does this podcast release new episodes?
This podcast updates bi-weekly.
- Where can I listen to this podcast?
This podcast is available on 7 platforms including Apple Podcasts, Spotify, and more. You can also use the RSS feed directly.
- Does this podcast accept guests?
Yes, this podcast regularly features guests.
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