Executives Unplugged

Doing what's best for you sounds obvious until you're a high achiever surrounded by status, prestige, and everyone else's expectations.Allison Canton has lived that tension, from Harvard Law to big law to startup general counsel, and in this episode she gets brutally honest about what it takes to trust your own judgment. We talk about how your environment influences your decisions, the difference between healthy ambition and ego, and the night she woke up and wrote "I CAN'T DO THIS!" Getting from there to a decision took time, a change of scenery, room to think, and daily habits she keeps coming back to. If you want to truly choose your next destination instead of just following the status train wherever it goes, this one's for you.Chapters00:00 "I can't do this. I need to quit."00:35 Meet Allison Canton01:35 Harvard Law by accident05:55 The pull of prestige08:10 Who's really making the decision?14:53 From Flatiron to general counsel15:51 The story that work comes first19:32 When the story becomes your identity21:38 Leaving New York, and one more title25:18 Healthy chasing vs. ego27:07 The two kinds of hard decisions28:06 The night it broke30:45 How your environment makes decisions for you34:01 It doesn't have to look a certain way35:57 Change your environment, then play39:19 Meditation, journaling, and a clear head42:05 The toughest question43:32 Closing thoughtsAllison Canton:LinkedIn: https://www.linkedin.com/in/allisoncanton/Website: https://allisoncanton.comKeith Cowing: LinkedIn: https://linkedin.com/in/keithcowingJoin the Inner Circle: https://execs.tvSubscribe: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

Resumes mean less than ever. Here's what top AI CEOs hire for instead.Michael Cullen recruits executive teams for some of the fastest-moving AI companies in the world. We sat down in person at Kit Studios in New York City to get into how the exec hiring playbook has changed: why marketing should come earlier than you think, what happened after the forward-deployed engineer mania, why big-company leaders rarely translate to startups, and the overlooked signal he looks for on resumes. We also get practical about how he actually interviews, why he hires for decisiveness over perfection, and how to close a candidate who has five other offers.00:00 Intro00:41 Comic Con and why New York is a place to build01:55 The Iron Man moment: AI is the suit, you're still the human02:40 The exec who crushes the interview, then gets fired03:12 Why you should hire marketing earlier04:58 Copycat products: features collapse, story wins06:07 The age of the generalist07:32 Resumes vs mindset08:31 What happened to forward-deployed engineers12:37 The overlooked resume signal13:35 Hire for slope, not experience15:25 Big company to startup: who actually translates17:18 Make a call: why 100 decisions beats 2018:54 How he interviews: pick apart the narrative20:01 How to close a candidate with five offers22:31 Why you can't judge culture over Zoom24:04 Back in the office, and the end of 99625:35 Why build in New YorkMICHAEL CULLENhttps://www.linkedin.com/in/cullenmm/https://bleeckerstconsulting.com/KEITH COWINGhttps://linkedin.com/in/keithcowinghttps://keithcowing.comEXECUTIVES UNPLUGGEDhttps://execs.tv

In today's world, how you show up is more important than ever.Dre Baldwin started playing basketball at 14, came out of a Division III school and willed himself into a nine-year professional basketball career. He now brings the same discipline to executives and organizations. We talk about what makes great results repeatable, why leaders should measure execution and not just outcomes, and how reliability compounds into an advantage. We also get into Power Presence, Dre's approach to improving presence by removing noise, and why judgment and presence matter more as AI makes information and answers abundant.Chapters00:00 Intro 00:33 The Execution Reliability Index 02:16 Film study and Lawrence Taylor breaking the script 05:23 How ERI works inside a company 07:06 What the first version got wrong 08:43 Reinventing from pro basketball to business 10:23 Exposure camps, VHS tapes, and 60 agents 12:20 Conviction when every answer is no 14:07 How basketball players led him to mindset 16:19 Unlearning brute force 18:46 Getting on the same side of the table 21:16 Power Presence 24:10 Consistency, not peak energy 25:44 The third day and the empty gym 29:28 Where discipline comes from 31:12 Ray Dalio and thinking three steps ahead 34:23 Coaching from game tape, not therapy 36:47 Kobe, Tracy McGrady, and coasting 39:47 Wrap-upDre Baldwinhttps://www.linkedin.com/in/dreallday/https://www.dreallday.com/Executives Unpluggedhttps://execs.tvKeith Cowinghttps://keithcowing.comhttps://linkedin.com/in/keithcowing

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.CHAPTERS00:00 Intro01:03 The case for a single-threaded leader05:12 Healthy tension without veto power06:53 The Wednesday business review09:17 Turning meetings into context for AI10:37 Recording everything by default12:30 Change management when it touches people's jobs14:18 How to tell if your exec team is too slow16:27 Business leaders, not functional leaders19:01 Anger, fear, and the decisions they cause19:49 Underwriting risk instead of pushing it down22:22 One-way doors and two-way doors23:37 The readme that names who decides what24:44 Calm but oddly ambitious27:31 Weasel words30:11 Pairing authority with accountability32:34 Who owns pricing35:39 One data layer for the whole exec team37:39 Hiring outside the bubble40:46 WrapMAHESH GURUSWAMYhttps://www.linkedin.com/in/maheshguruswamy/https://www.thesensiblemanager.comhttps://www.amazon.com/How-Deliver-Bad-News-Away/dp/B0D7FHTTNNKEITH COWINGhttps://linkedin.com/in/keithcowinghttps://keithcowing.comEXECUTIVES UNPLUGGEDhttps://execs.tv

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 SkySync00:48 Why 90% of AI projects are stuck in a pilot02:22 Manage AI agents like employees03:45 Inside a 300% growth story06:55 Why change management is the real bottleneck09:30 Offense vs. defense: the exec mindset12:26 The tech decisions behind a true 360° view15:12 Governance before you scale: CISOs, GDPR, data residency21:03 Codifying workflows and keeping humans in the loop23:50 Where to start: internal agents first26:52 Mining meeting transcripts and existing systems29:42 ROI dashboards: token measuring, not maxing30:13 Why Akshit’s building in NYCFollow 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.tvSubscribe to Executives Unplugged: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

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