Executives Unplugged

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.Chapters00:00 Introduction00:44 Rule 1: Put All Your Data in One Place02:00 Rule 2: Build Context That Compounds03:28 Rule 3: Design for Rapidly Swapping Models05:03 Rule 4: Use the Right Model for the Right Problem06:55 Rule 5: Mix Deterministic Software with LLMs08:21 Rule 6: Orchestrate Based on Frequency and Value10:44 Rule 7: Keep Agents Narrowly Focused12:04 Rule 8: Get Ready to Iterate12:52 Rule 9: Managing Agents Is a New Skill15:00 Rule 10: Half of What You Build Is Disposable17:11 Your Next Steps: Just Start BuildingFollow Keith Cowing on LinkedIn: https://linkedin.com/in/keithcowingJoin the Inner Circle: https://execs.tvSubscribeYouTube: https://www.youtube.com/playlist?list=PLU_rgycqchjl1jNqjOeJFepyr9yfcXWcMSpotify: https://open.spotify.com/show/1Bw7KhjlUzFjMoFhdfNAKNApple Podcasts: https://podcasts.apple.com/us/podcast/executives-unplugged/id1769131263

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.Chapters01:13 Start With Why03:10 Avoid Logo Trap04:28 Real Search Example07:50 Trajectory Not Altitude08:48 Assess Judgment & Speed10:52 Culture Fit Walkthrough12:28 Management In Details13:59 AI Native Leaders17:15 Hiring With Conviction19:23 Candidate Due Diligence20:48 Align Expectations23:19 Close The Candidate25:13 The Market Shift26:14 Five TakeawaysFind 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/

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 burnoutConnect 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-592cdc1f1704Follow Keith Cowing on LinkedIn: https://linkedin.com/in/keithcowingJoin the Executives Unplugged Inner Circle for free coaching via email: https://execs.tvSubscribe to the show:YouTube: https://www.youtube.com/playlist?list=PLU_rgycqchjl1jNqjOeJFepyr9yfcXWcMSpotify: https://open.spotify.com/show/1Bw7KhjlUzFjMoFhdfNAKNApple Podcasts: https://podcasts.apple.com/us/podcast/executives-unplugged/id1769131263

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/ShoutoutsRightMove Health: https://rightmovehealth.comFollow Keith Cowing on LinkedIn: https://linkedin.com/in/keithcowing Join the Executives Unplugged Inner Circle: https://execs.tvSubscribe 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

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 boardFollow Matt on LinkedIn: https://www.linkedin.com/in/mattblumberg/ShoutoutsStartup Boards: https://www.amazon.com/Startup-Boards-Building-Effective-Directors/dp/111985928XMarkup AI: https://markup.aiFred Wilson: https://avc.xyzMike 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.coachSubscribe 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

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 tone05:00 — The value of “having a sleep” between days07:40 — The CEO’s role: set vision, not the agenda10:50 — Creating meeting agreements that drive honesty16:20 — The facilitator’s job: manage time and truth18:50 — Handling conflict when the “fight” breaks out22:30 — Tools for structure: parking lots, sticky notes, and timers25:40 — Decision-making without consensus traps28:20 — The “Fist to Five” tool for real alignment30:20 — Ensuring follow-through and lasting impact33:30 — Why offsites are the most powerful (and risky) meetings you’ll ever runFollow Kelly Dwyer on LinkedIn: https://www.linkedin.com/in/kellydwyer/Visit Kelly’s Website: https://kellydwyer.coListen to Kelly’s Podcast: https://www.lifefromwithin.com/Follow Keith Cowing on LinkedIn: https://linkedin.com/in/keithcowingSubscribe to Keith’s free coaching via email: https://kc.coach/Subscribe to the show:YouTube: https://www.youtube.com/@kcowingSpotify: https://open.spotify.com/show/1Bw7KhjlUzFjMoFhdfNAKNApple Podcasts: https://podcasts.apple.com/us/podcast/executives-unplugged/id1769131263

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 humanShoutouts: 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/rovoFollow 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.coachSubscribe 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

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 loopsDrink 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/keithcowingJoin the Executives Unplugged Community and get free office hours: https://kc.coach/executives-unpluggedSubscribe to the show:YouTube: https://www.youtube.com/playlist?list=PLU_rgycqchjl1jNqjOeJFepyr9yfcXWcMSpotify: https://open.spotify.com/show/1Bw7KhjlUzFjMoFhdfNAKNApple Podcasts: https://podcasts.apple.com/us/podcast/executives-unplugged/id1769131263

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 stepThe “two truths and two pies” exerciseSimple psychological tricks to protect your focusWhy just a 10% shift can double your momentumSubscribe 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, shiftFollow Keith Cowing:Follow on LinkedIn: https://linkedin.com/in/keithcowing  Join the Executives Unplugged community for free coaching via email: https://kc.coachSubscribe to the show:YouTube: https://www.youtube.com/playlist?list=PLU_rgycqchjl1jNqjOeJFepyr9yfcXWcMSpotify: https://open.spotify.com/show/1Bw7KhjlUzFjMoFhdfNAKNApple Podcasts: https://podcasts.apple.com/us/podcast/executives-unplugged/id1769131263

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 competition, this episode offers a playbook. Product leader Nate Gosselin introduces a new model inspired not by corporate frameworks, but by hip-hop producers. He breaks down the concept of the "Product Producer" and the shift from rigid, siloed teams to small, nimble "studios" powered by AI. This conversation provides a tactical guide for leaders to rethink their org design, tackle technical debt, and build the multidisciplinary teams needed for the future. In this episode, you’ll learn: (01:31) What is a "Product Producer"? (05:12) The Skills to Hire For: AI Literacy and Multidisciplinary Talent (11:09) Managing AI Like a Team of Highly Capable Interns (13:30) Where to Start: Low-Risk, High-Impact AI Projects (16:33) How to Use AI to Tackle Your Scariest Tech Debt (20:49) The New Org Model: Shifting from Assembly Lines to Creative Studios (31:53) Your First Step: A Practical Guide to Implementing AI in Your Workflows (39:08) The Personal Transformation for Leaders: From Specialist to Builder Follow Keith Cowing: LinkedIn: https://linkedin.com/in/keithcowing Subscribe to 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 Follow Nate Gosselin: LinkedIn: https://www.linkedin.com/in/nate-gosselin Website: https://www.heynate.me/

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 Perry Steinberg, a seasoned Chief Product Officer with deep experience leading through high-stakes transitions at both public companies and fast-paced private equity-backed firms. Perry unpacks his core leadership philosophy for navigating this exact challenge, revealing how to maintain cohesion and drive results simultaneously.In this conversation, you will learn:The Art of Cadence and Commitment: The methods Perry uses to build trust and alignment, even when making difficult decisions.Leading the 'Mindset Shift': Discover techniques to guide an organization through a fundamental change in thinking and strategy.From Chaos to Cohesion: Hear how Perry unified disparate teams and roadmaps post-acquisition to create a single, focused vision.Staying Relevant in the AI Era: Understand why past playbooks are obsolete and what skills are critical for leadership in a world of constant technological disruption.This episode is for any leader tasked with steering their organization through uncertainty.---Access free, email-based coaching for executives. Join the conversation at https://kc.coach.

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 Unplugged, I talk with Natasha, an experienced engineering leader and coach who has guided teams at both Fortune 100 companies and startups through multi-billion dollar acquisitions.We have a raw and honest conversation about the critical mistake leaders make when they chase productivity gains but accidentally "squash the magic" that makes their teams special. Natasha shares a powerful playbook for leading through disruptive changes—like reorgs or the push for AI—by protecting your team's "flow state" and listening to your own moral compass.This episode is a masterclass in leading with empathy and principle, offering practical advice on how to navigate immense change without losing your team, or yourself, in the process.Guest:Natasha Jaffe: Experienced Engineering Leader and Coach.Find Natasha's writing at her blog: Nuts and Bolts on SubstackIn this episode, we discuss:(1:13) What is "Flow State"? Natasha explains why long, uninterrupted blocks of time are the source of an engineer's most creative and deep work.(2:11) How Leaders Destroy Flow: Forcing teams to prioritize the "important" over the "interesting" for too long erodes curiosity and squashes the magic.(3:40) The Human Reaction to AI: Why engineering teams often react to top-down AI mandates with trepidation, seeing it as "dystopian" and a threat to their craft.(4:35) Fear Kills Innovation: When your team is afraid, they won't engage in the productive risk-taking required to innovate.(5:11) A Case Study in Leading a Reorg: How Natasha turned a messy, demoralizing situation into a success by bringing the team into the decision-making process, listening to their fears, and even choosing a team mascot.(8:33) The Real Path to Moving Faster: Stop telling your engineers to "run harder." Instead, reduce toil and remove friction to "widen the mouth of the funnel."(9:16) The Collapsing Talent Stack: Are we moving away from hyper-specialists and back toward multi-skilled teams who can move with lightning speed?(12:49) The Bell Curve of Team Size: The trade-off between having more minds on a problem and the rapid degradation of velocity and quality when "too many cooks are in the kitchen."(15:01) Your Moral Compass: Why you can't leave your values at home and how the biggest career regrets come from not listening to your gut.(16:35) "They Said the Quiet Part Out Loud": The powerful story of how a single comment about integrity was the signal Natasha needed to make a pivotal career change.(18:41) Key Questions to Ask Yourself: How to get clarity when your job is in conflict with your values, and how to know when it's time to explore a change.(22:08) On Burnout and Recovery: Natasha shares her personal journey of recovering from massive burnout and rediscovering creativity.

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 Lovelle, a former professional ballet dancer turned plastic surgeon, now founder & CEO of Balanced Performance, and her long-time colleague Tonya Sook, a Certified Family Nurse Practitioner.Discover Dr. Lovelle's unconventional approach to hiring – prioritizing inner skills over years of experience – and how it built a thriving practice. Hear her incredible story of multiple reinventions, driven by passion and necessity, and learn how to navigate your own transformations. Tonya shares the ground-level view of building a culture of trust and excellence. Learn practical strategies for assessing talent beyond the resume, fostering team alignment, managing your energy to avoid burnout, and applying the "Listen, Let Go, Live" method for peak performance.GuestsDr. Susan Lovelle: Former professional ballet dancer (17 years), plastic surgeon, and now Founder/CEO of Balanced Performance, helping executives optimize their health and leadership. Learn more at Balanced Performance.Tonya Sook APRN-C: Certified Family Nurse Practitioner specializing in medical aesthetics, hormone therapy, dermatology, and functional medicine, dedicated to holistic patient well-being.View on your favorite platformYoutube: https://youtu.be/Stgj-ZwL45wSpotify: https://open.spotify.com/episode/6n4zRnSVJf1ZfRITtG1VK8?si=lO_8BZWoTXWL5WeT-ZhvQwApple Podcasts: https://podcasts.apple.com/us/podcast/from-ballet-to-scalpel-to-ceo-reinvention-resilience/id1769131263?i=1000705573303[00:00:00] Intro / From Dance to Medicine[00:00:19] Welcome & Guest Introductions[00:01:24] Hiring Philosophy: Skills Over Experience[00:02:47] The Group Interview & Testing for Inner Workings[00:04:10] Why Experience Can Be Overrated[00:04:41] Tonya Sook: Cultivating Culture & Trust[00:05:08] Enabling Teams to Be Themselves[00:06:09] Learning Leadership Through Delegation[00:07:36] Reinvention 1: Ballet to Medical School[00:09:39] Reinvention 2: Surgery to Lifestyle Coaching (The Wake-Up Call)[00:11:25] Finding Your Energy & Root Causes[00:12:55] The L3 Method: Listen, Let Go, Live[00:14:14] Tonya Sook: The Art of Nurse Practitioner Leadership (Gentle Firmness)[00:16:33] Learning You Can't Help Everyone[00:17:35] Discipline: The Common Thread from Ballet to Business[00:19:45] Performance: How You Show Up Matters[00:21:57] What's Next? Scaling Impact Through Corporate Wellness[00:22:49] Lessons Learned from Working Together[00:24:07] Why Dr. Susan Isn't a "Typical" Surgeon[00:26:20] Key Takeaways & Conclusion

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 companies sell and grow. Uday shares his journey from idea to his first $100K in revenue in just 12 months, revealing the strategies that fueled his success: ruthless prioritization, weekly sprints, and a customer-first mindset. From managing a costly API glitch in the middle of the night to leveraging advisors for go-to-market mastery, Uday’s story is packed with actionable insights for CEOs, founders, or anyone looking to accelerate team performance and growth.Key topics include:The zero-to-one journey: How Uday refined his idea, assembled a core team, and got first customers quickly.Time-zone challenges: Strategies for async communication, “bat phone” emergencies, and using Loom/WhatsApp for round-the-clock collaboration.Surrounding yourself with expertise: Building advisory boards, the difference between “cheerleader” advisors and hands-on experts, and how to get real-time coaching on your sales calls.Fast execution: Why shipping weekly sprints and labeling “deal-breaker” features help close deals and energize the team.Real-world examples: How a coding error led to thousands of dollars in AI API charges—and why having rapid response processes in place was critical.Show Notes:[0:00] Intro: Uday’s runaway API call costing thousands overnight.[1:25] Uday’s Journey: From Atlassian to founding Clinch AGI in the agentic AI space.[3:39] Speed Secrets: Building a core team, async communication, and customer collaboration.[8:14] Advisory Boards: How Uday strategically filled skill gaps with experts.[17:48] Actionable Advice: Validate problems early, invest in relationships, and prioritize ruthlessly.[19:31] Execution Hacks: Weekly sprints, AI-driven prioritization, and “deal breaker” focus.Where to Find Uday:Connect with Uday Chakravarthi on LinkedIn: https://www.linkedin.com/in/abhyuday/Learn more about Clinch AGI: clinchit.ioWhere to Find Keith:Visit Keith Cowing’s coaching site for CEOs and product leaders: kc.coachFollow Keith on LinkedIn for leadership insights: linkedin.com/in/keithcowing References from the Show:Executive Product Leadership Program: Unlock AI’s potential for your team with this two-day in-person workshop at Cornell Tech in September. Details at kc.coach/cornellIf you loved this episode, share it with a fellow leader or leave a five-star review to help others discover Executives Unplugged. Subscribe for more real talk from top executives.

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 - shares his journey from the boxing ring to the boardroom, revealing hard-earned lessons on resilience, branding, and the power of action.Mike takes us inside one of his toughest leadership moments: running a nonprofit boxing gym in Newark, NJ, when COVID shut everything down overnight. With his back against the ropes, he found a way to pivot, reinvent, and build something even stronger. Now, as a sought-after business coach for veteran entrepreneurs, he helps others define their brand, find their market, and take decisive action in the face of uncertainty.🔹 Key Takeaways:•How to turn adversity into momentum—even when you feel stuck•Why action builds confidence•The power of niching down and owning your brand identity•How to battle imposter syndrome and step into leadership with clarity•What it really takes to sell yourself and your business with convictionWhether you’re an entrepreneur, leader, or someone looking for the mindset to push through tough times, this episode delivers practical lessons and real-world insights that will get you off the mat and back in the fight.🎧 Listen now and take your leadership to the next level!YouTubeSpotifyApple PodcastsMike Steadman: ironmikesteadman.comBlack Veteran Entrepreneur: Validate your business model, build your brand, and step into greatnessKeith Cowing (host): kc.coachReferences:The Four AgreementsThe Confident MindHow Champions ThinkPlay Bigger

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 insights on go-to-market strategies, building sustainable sales teams, and the critical role of truth in creating long-term success.💡 Key Topics Covered: • How to diagnose product-market fit and go-to-market fit. • The truth-driven approach to selling and why it builds trust and success. • Structuring sales team incentives for long-term growth and customer success. • Leadership lessons from Silicon Valley and beyond. • Wayne’s wild journey from London to Silicon Valley.Whether you’re a founder, sales leader, or just curious about what it takes to thrive in high-growth startups, this episode is packed with practical advice and compelling stories.📍 Take Wayne’s Free Go-to-Market Assessment: RVNU.coYou can find his Go-To-Market framework one pager highlighted on this post: https://rvnu.substack.com/p/rvnu-017-exposing-if-a-startup-willDirect link to the one page image: https://substackcdn.com/image/fetch/f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fadf1d891-263a-4bd1-ba16-9d96e0a4f152_2378x1326.png📧 Connect with Host Keith Cowing: kc.coachShare your thoughts and feedback—Keith responds to every listener!If you enjoyed this episode, please like, subscribe, and share it with someone who might find it valuable. Don’t forget to leave a review to help others discover Executives Unplugged!

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 empathetic yet decisive leadership and how to build trust with founders, making swift decisions with limited data in high-stakes environments.Tune in for a treasure trove of practical advice and strategies that provide a roadmap for navigating the complexities of high-growth environments.

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. Danielle opens up about her experiences managing former peers, building self awareness and confidence, communicating transparently and holding people accountable.Danielle also shares some of her management templates and playbooks that she has open-sourced to the world in the form of a GitHub repository.Tune in to gain a wealth of insights on effective leadership, communication strategies, and continuous learning from one of the industry's most dynamic leaders.You can find Danielle's open-source management playbooks here: https://github.com/dmleong

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 moments that shaped Siwat’s leadership style, from teamwork in a hospital, to launching a series of businesses, to inspiration from great coaches such as Carlo Ancelotti and Phil Jackson. This episode is packed with insights on resilience, developing a brand, and leading with purpose.Visit Recoup at:https://recoupwellness.comhttps://instagram.com/recoupwellnesshttps://www.amazon.com/stores/recoup/page/B58DA3B7-E2E4-49F5-AE28-C8B982FABE17Book recommendations from Siwat:Quiet Leadership by Carlo Ancelottihttps://www.amazon.com/Quiet-Leadership-Winning-Hearts-Matches/dp/024124493511 Rings by Phil Jacksonhttps://www.amazon.com/Eleven-Rings-audiobook/dp/B00CTE0YTC/Tribal Leadershiphttps://www.amazon.com/Tribal-Leadership-audiobook/dp/B07NF1R92F