Executives Unplugged

Keith Cowing
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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.

  1. The Truth About Hiring Your First Head of Product

    -1 ДН.

    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/

    28 мин.
  2. Field Notes from 20 Years of NYC Startups

    29 ЯНВ.

    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

    34 мин.
  3. Why 50% of Startup Executive Hires Fail (and How to Fix It)

    22.12.2025

    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

    28 мин.
  4. 250 Board Meetings Later: This CEO’s playbook will change your board meetings forever

    26.11.2025

    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

    30 мин.
  5. Mastering executive offsites

    04.11.2025

    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

    35 мин.
  6. How to bring startup speed to big organizations

    21.10.2025

    How to bring startup speed to big organizations

    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 things up - but if you move too quickly, you lose people. This episode dives into that tension. Atlassian’s Head of AI, Nisha Iyer, shares what happens when a startup founder joins a 10,000-person company and tries to build new AI products from the inside. She unpacks learning to slow down, earning trust, and building momentum the right way - without giving up the spark that made you effective in the first place. Executives and operators will relate to the tension between urgency and patience - and take away ideas for leading change without burning out your team or losing trust. 00:00 — Moving fast meets resistance04:00 — “Learn the business”: slowing down to speed up09:00 — The big swing that fell flat — and the lesson in humility17:00 — Piloting change and earning trust one team at a time22:00 — Turning internal wins into customer-facing AI26:00 — Balancing empathy, momentum, and trust31:00 — Reducing fear, sparking excitement: leading through change36:00 — What’s next: voice tech, connection, and being more human Shoutouts: The First 90 Days — https://www.amazon.com/First-90-Days-Strategies-Expanded/dp/1422188612 Atlassian — https://www.atlassian.com Rovo — https://www.atlassian.com/software/rovo Follow Nisha Iyer: https://www.linkedin.com/in/nisha-ranjani-iyer/ Follow Keith Cowing: 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

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

    09.10.2025

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

    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 ginger-forward beverages into a national Target launch. You’ll learn how to build an advisory bench, get massive distribution, expand margins, and use polarizing positioning to earn raving fans. (00:00) Intro — From trade shows to Target shelves (03:20) Lean teams, volunteers, and winning Pitch Slam (06:48) Building an advisory board that moves margins (13:16) Polarization as a brand strategy: the ginger edge (16:33) Customer feedback and fast iteration (25:45) Rethinking risk: small bets, tight feedback loops Drink recoup: https://www.recoupwellness.com/ Follow Siwat Siengsanaoh on LinkedIn: https://www.linkedin.com/in/siwatsiengsanaoh/ Follow Keith Cowing on LinkedIn: https://linkedin.com/in/keithcowing Join the Executives Unplugged Community and get free office hours: https://kc.coach/executives-unplugged 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

    33 мин.

  8. 15.09.2025

    From Burnout to Breakthrough: Master Your Calendar

    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 schedule, spot energy-drainers, and make small but powerful changes that double your strategic time without burning out. You’ll discover: How to run a calendar audit step by step The “two truths and two pies” exercise Simple psychological tricks to protect your focus Why just a 10% shift can double your momentum Subscribe for more playbooks to lead with clarity and momentum. Chapters: (00:00) Intro — Is your calendar running your life? (00:51) The Tetris analogy: when meetings feel like blocks falling (02:20) Step 1 — Calendar audit explained (04:06) Step 2 — Analyzing results: the two pies and two truths (07:53) Step 3 — Making changes and mindset shifts (09:04) Protecting your focus like it’s a meeting with the CEO (11:11) Setting boundaries and saying no with confidence (12:48) Closing thoughts — audit, analyze, shift Follow Keith Cowing: Follow on LinkedIn: https://linkedin.com/in/keithcowing   Join the Executives Unplugged community for free coaching via email: https://kc.coach 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

    14 мин.
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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.

Информация

  • Автор
    Keith Cowing
  • Годы выхода
    2024 - 2026
  • Выпуски
    18
  • Ограничения
    С ненормативной лексикой
  • Авторские права
    © 2025 Keith Cowing
  • Сайт подкаста
    Executives Unplugged