Executives Unplugged

Keith Cowing
  • 5.0 (8)
  • Entrepreneurship
  • Updated Biweekly

CEOs have coaches behind the scenes, but few people get to hear those conversations. Executives Unplugged puts you in that room. I'm Keith Cowing, an executive coach and 2x founder. I go deep with CEOs and operators so you can learn from the case studies that matter most: the ones playing out right now.

  1. 4d ago ·  Video

    Consensus Is Too Slow, Even With Two People | Mahesh Guruswamy, COO of Kajabi

    Teams 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 he picked up at Amazon and carried through Smartsheet and Kickstarter. His case is simple: when two peers share a decision and neither one can break the tie, the whole org waits for them to agree. We get into how he keeps genuine challenge in the room without giving anyone veto power, why he runs a business review every Wednesday, and exactly which decisions he keeps versus delegates. We also cover what it takes to get from your current model to an AI-native model when the change touches people's jobs and nobody volunteers to give up their turf. CHAPTERS 00:00 Intro 01:03 The case for a single-threaded leader 05:12 Healthy tension without veto power 06:53 The Wednesday business review 09:17 Turning meetings into context for AI 10:37 Recording everything by default 12:30 Change management when it touches people's jobs 14:18 How to tell if your exec team is too slow 16:27 Business leaders, not functional leaders 19:01 Anger, fear, and the decisions they cause 19:49 Underwriting risk instead of pushing it down 22:22 One-way doors and two-way doors 23:37 The readme that names who decides what 24:44 Calm but oddly ambitious 27:31 Weasel words 30:11 Pairing authority with accountability 32:34 Who owns pricing 35:39 One data layer for the whole exec team 37:39 Hiring outside the bubble 40:46 Wrap MAHESH GURUSWAMY https://www.linkedin.com/in/maheshguruswamy/ https://www.thesensiblemanager.com https://www.amazon.com/How-Deliver-Bad-News-Away/dp/B0D7FHTTNN KEITH COWING https://linkedin.com/in/keithcowing https://keithcowing.com EXECUTIVES UNPLUGGED https://execs.tv

    Consensus Is Too Slow, Even With Two People | Mahesh Guruswamy, COO of Kajabi

  2. Jul 1

    Why 90% of AI Agents Are Stuck in a Pilot

    The 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 inside Salesforce's Agentforce platform. Now, as CEO of SkySync, he helps companies deploy and manage AI agents. In this episode he walks through the four moves that separate the teams getting real returns from the 90% stuck experimenting. Along the way he unpacks a client that grew new business 300% with a single marketing agent, why fear drives the worst decisions in a transformation, and how to measure ROI with a master dashboard. 00:00 Intro: Akshit Kandi and SkySync 00:48 Why 90% of AI projects are stuck in a pilot 02:22 Manage AI agents like employees 03:45 Inside a 300% growth story 06:55 Why change management is the real bottleneck 09:30 Offense vs. defense: the exec mindset 12:26 The tech decisions behind a true 360° view 15:12 Governance before you scale: CISOs, GDPR, data residency 21:03 Codifying workflows and keeping humans in the loop 23:50 Where to start: internal agents first 26:52 Mining meeting transcripts and existing systems 29:42 ROI dashboards: token measuring, not maxing 30:13 Why Akshit’s building in NYC Follow Akshit on LinkedIn: https://www.linkedin.com/in/akandi6/ SkySync: https://www.skysync.nyc/ Follow Keith on LinkedIn: https://linkedin.com/in/keithcowing Join Keith's Inner Circle: https://execs.tv Subscribe to Executives Unplugged: YouTube: https://www.youtube.com/playlist?list=PLU_rgycqchjl1jNqjOeJFepyr9yfcXWcM Spotify: https://open.spotify.com/show/1Bw7KhjlUzFjMoFhdfNAKN Apple Podcasts: https://podcasts.apple.com/us/podcast/executives-unplugged/id1769131263

    Why 90% of AI Agents Are Stuck in a Pilot

  3. Apr 21

    10 Rules for Building AI Agents That Actually Work

    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. 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. Chapters 00:00 Introduction 00:44 Rule 1: Put All Your Data in One Place 02:00 Rule 2: Build Context That Compounds 03:28 Rule 3: Design for Rapidly Swapping Models 05:03 Rule 4: Use the Right Model for the Right Problem 06:55 Rule 5: Mix Deterministic Software with LLMs 08:21 Rule 6: Orchestrate Based on Frequency and Value 10:44 Rule 7: Keep Agents Narrowly Focused 12:04 Rule 8: Get Ready to Iterate 12:52 Rule 9: Managing Agents Is a New Skill 15:00 Rule 10: Half of What You Build Is Disposable 17:11 Your Next Steps: Just Start Building Follow Keith Cowing on LinkedIn: https://linkedin.com/in/keithcowing Join the Inner Circle: https://execs.tv Subscribe YouTube: https://www.youtube.com/playlist?list=PLU_rgycqchjl1jNqjOeJFepyr9yfcXWcM Spotify: https://open.spotify.com/show/1Bw7KhjlUzFjMoFhdfNAKN Apple Podcasts: https://podcasts.apple.com/us/podcast/executives-unplugged/id1769131263

  4. Apr 7

    The Truth About Hiring Your First Head of Product

    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 relationships fail within the first 18 months and a lot of that pain starts with how the hire was made in the first place. 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. 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. 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. Chapters 01:13 Start With Why 03:10 Avoid Logo Trap 04:28 Real Search Example 07:50 Trajectory Not Altitude 08:48 Assess Judgment & Speed 10:52 Culture Fit Walkthrough 12:28 Management In Details 13:59 AI Native Leaders 17:15 Hiring With Conviction 19:23 Candidate Due Diligence 20:48 Align Expectations 23:19 Close The Candidate 25:13 The Market Shift 26:14 Five Takeaways Find the guests on LinkedIn: Jodi Jefferson: https://www.linkedin.com/in/jodijefferson/ Michael Cullen: https://www.linkedin.com/in/cullenmm/ Chris Running: https://www.linkedin.com/in/chris-running-a94a8025/ Dennis Crowley: https://www.linkedin.com/in/dpstyles/

    The Truth About Hiring Your First Head of Product

  5. Jan 29

    Field Notes from 20 Years of NYC Startups

    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 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. Chapters(00:00) Intro — A founder’s field notes from NYC (03:05) Why writing things down changes your brain (09:10) “You fall to the level of your systems” (14:45) From Dodgeball → Foursquare → Hopscotch Labs (19:35) BeeBot — proactive, wearable AI and why it’s hard (27:15) Hiring for uncertainty: side projects, skill, and resilience (34:30) NYC tech evolution — capital, talent, and density (41:10) How to battle burnout Connect with Keith or DennisFollow Dennis Crowley on LinkedIn: https://www.linkedin.com/in/dpstyles/ Follow Dennis Crowley on Substack: https://teendrama.substack.com/ Hopscotch Labs: https://hopscotchlabs.co/ BeeBot: https://dens.medium.com/say-hello-to-dj-beebot-592cdc1f1704 Follow Keith Cowing on LinkedIn: https://linkedin.com/in/keithcowing Join the Executives Unplugged Inner Circle for free coaching via email: https://execs.tv Subscribe to the show: YouTube: https://www.youtube.com/playlist?list=PLU_rgycqchjl1jNqjOeJFepyr9yfcXWcM Spotify: https://open.spotify.com/show/1Bw7KhjlUzFjMoFhdfNAKN Apple Podcasts: https://podcasts.apple.com/us/podcast/executives-unplugged/id1769131263

    Field Notes from 20 Years of NYC Startups

  6. 12/22/2025

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

    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 momentum and kill team morale. Yet, most companies are still playing a game of mutual selling that incentivizes flaunting and filtering over honesty and results. Meghan Oliver decided to stop playing that game. After stepping off the corporate hamster wheel to build her own business, she found a way to bypass the interview dance entirely. She joined a Series A healthcare company as a fractional product leader. No elongated interview process, just real problems to solve on day one. What started as a 90-day experiment ended with Meghan rewriting the company’s product and operations playbook and stepping in as full-time COO. In this episode, Meghan reveals her framework for how to wildly reduce the risk of a mis-hire and either close your next great executive or land your next great gig. Chapter Markers: 00:00 — Why traditional executive hiring often fails 01:00 — Meghan’s path: burnout, sabbatical, and discovering fractional 03:20 — Starting fractional at RightMove Health as CPO 04:20 — Finding clarity in context, not just function 07:20 — What makes a fractional executive role actually work 10:50 — Evolving from fractional CPO to full-time COO 13:20 — Why combining product and ops cuts coordination tax 15:00 — The power of a 90-day “try before you buy” 15:40 — Navigating health insurance and benefits as fractional 18:40 — How the role shift felt seamless for the team 20:40 — Building conviction and quieting self-doubt 22:40 — Advice for CEOs and executives on fractional hires 26:20 — What’s happening at RightMove Health (and open roles) Follow Meghan Oliver: https://www.linkedin.com/in/meghan-oliver/ Shoutouts RightMove Health: https://rightmovehealth.com Follow Keith Cowing on LinkedIn: https://linkedin.com/in/keithcowing Join the Executives Unplugged Inner Circle: https://execs.tv Subscribe to the show YouTube: https://www.youtube.com/@execsunplugged Spotify: https://open.spotify.com/show/1Bw7KhjlUzFjMoFhdfNAKN Apple Podcasts: https://podcasts.apple.com/us/podcast/executives-unplugged/id1769131263

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

  7. 11/26/2025

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

    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 time sink full of status updates and glazed eyes. In this episode Matt Blumberg, the CEO of Markup AI and author of Startup Boards, breaks down how to turn your board meetings into your ultimate strategy session. Matt shares the story of a "perfect" board candidate who failed a live audition, the "Rule of Ones" that will lead to an effective board composition, and why he strictly forbids slides during meetings. He also reveals a new experiment: using AI agents to simulate a "Fantasy Board" meeting with personalities like Steve Jobs and Warren Buffett to stress-test decisions before the real directors show up. Executives will come away with a playbook to stop reporting and start using their board to build the business. Chapters00:00 — The No Slides Rule 02:04 — Turning the eye roll into strategy 03:20 — The Audition: Making directors do the work 06:58 — How to reference check your VCs 08:59 — The "Rule of Ones" for board composition 13:25 — Stop writing 50-page board decks 17:24 — Specific rules for better conversations 20:58 — Inside the Markup AI pivot 23:05 — The "Fantasy Board": Simulating Steve Jobs with AI 26:19 — How to fire a board member 28:17 — Why every CEO should sit on another board Follow Matt on LinkedIn: https://www.linkedin.com/in/mattblumberg/ Shoutouts Startup Boards: https://www.amazon.com/Startup-Boards-Building-Effective-Directors/dp/111985928X Markup AI: https://markup.ai Fred Wilson: https://avc.xyz Mike Collins: https://www.linkedin.com/in/mike-collins-362100/ Follow Keith Cowing on LinkedIn: https://linkedin.com/in/keithcowing Join the Executives Unplugged inner circle: https://kc.coach Subscribe to the show: YouTube — https://www.youtube.com/@kcowing Spotify — https://open.spotify.com/show/1Bw7KhjlUzFjMoFhdfNAKN Apple Podcasts — https://podcasts.apple.com/us/podcast/executives-unplugged/id1769131263

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

  8. 11/04/2025

    Mastering executive offsites

    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 separates transformational offsites from frustrating ones. She’s helped leadership teams at venture and PE-backed companies turn tense conversations into breakthroughs and knows exactly how to keep the “elephant in the room” from derailing trust. Kelly and host Keith Cowing unpack a tactical playbook: how to prep the right way, design the space for honesty, navigate conflict, and make sure the alignment lasts. Leaders will walk away knowing how to run an offsite that doesn’t just check a box, but changes how their team thinks, decides, and leads. 00:00 — Why offsites fail (and how to fix them) 02:10 — How prep work sets the tone 05:00 — The value of “having a sleep” between days 07:40 — The CEO’s role: set vision, not the agenda 10:50 — Creating meeting agreements that drive honesty 16:20 — The facilitator’s job: manage time and truth 18:50 — Handling conflict when the “fight” breaks out 22:30 — Tools for structure: parking lots, sticky notes, and timers 25:40 — Decision-making without consensus traps 28:20 — The “Fist to Five” tool for real alignment 30:20 — Ensuring follow-through and lasting impact 33:30 — Why offsites are the most powerful (and risky) meetings you’ll ever run Follow Kelly Dwyer on LinkedIn: https://www.linkedin.com/in/kellydwyer/ Visit Kelly’s Website: https://kellydwyer.co Listen to Kelly’s Podcast: https://www.lifefromwithin.com/ Follow Keith Cowing on LinkedIn: https://linkedin.com/in/keithcowing Subscribe to Keith’s free coaching via email: https://kc.coach/ Subscribe to the show: YouTube: https://www.youtube.com/@kcowing Spotify: https://open.spotify.com/show/1Bw7KhjlUzFjMoFhdfNAKN Apple Podcasts: https://podcasts.apple.com/us/podcast/executives-unplugged/id1769131263

    Mastering executive offsites
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About

CEOs have coaches behind the scenes, but few people get to hear those conversations. Executives Unplugged puts you in that room. I'm Keith Cowing, an executive coach and 2x founder. I go deep with CEOs and operators so you can learn from the case studies that matter most: the ones playing out right now.

Information

  • Creator
    Keith Cowing
  • Years Active
    2024 - 2026
  • Episodes
    21
  • Rating
    Explicit
  • Copyright
    © 2025 Keith Cowing
  • Show Website
    Executives Unplugged