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

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 [https://linkedin.com/in/keithcowing] Join the Inner Circle: https://execs.tv [https://execs.tv] Subscribe YouTube: https://www.youtube.com/playlist?list=PLU_rgycqchjl1jNqjOeJFepyr9yfcXWcM [https://www.youtube.com/playlist?list=PLU_rgycqchjl1jNqjOeJFepyr9yfcXWcM] Spotify: https://open.spotify.com/show/1Bw7KhjlUzFjMoFhdfNAKN [https://open.spotify.com/show/1Bw7KhjlUzFjMoFhdfNAKN] Apple Podcasts: https://podcasts.apple.com/us/podcast/executives-unplugged/id1769131263 [https://podcasts.apple.com/us/podcast/executives-unplugged/id1769131263]

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/ [https://www.linkedin.com/in/jodijefferson/] Michael Cullen: https://www.linkedin.com/in/cullenmm/ [https://www.linkedin.com/in/cullenmm/] Chris Running: https://www.linkedin.com/in/chris-running-a94a8025/ [https://www.linkedin.com/in/chris-running-a94a8025/] Dennis Crowley: https://www.linkedin.com/in/dpstyles/ [https://www.linkedin.com/in/dpstyles/]

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 DENNIS Follow Dennis Crowley on LinkedIn: https://www.linkedin.com/in/dpstyles/ [https://www.linkedin.com/in/dpstyles/] Follow Dennis Crowley on Substack: https://teendrama.substack.com/ [https://teendrama.substack.com/] Hopscotch Labs: https://hopscotchlabs.co/ [https://hopscotchlabs.co/] BeeBot: https://dens.medium.com/say-hello-to-dj-beebot-592cdc1f1704 [https://dens.medium.com/say-hello-to-dj-beebot-592cdc1f1704] Follow Keith Cowing on LinkedIn: https://linkedin.com/in/keithcowing [https://linkedin.com/in/keithcowing] Join the Executives Unplugged Inner Circle for free coaching via email: https://execs.tv [https://execs.tv] Subscribe to the show: YouTube: https://www.youtube.com/playlist?list=PLU_rgycqchjl1jNqjOeJFepyr9yfcXWcM [https://www.youtube.com/playlist?list=PLU_rgycqchjl1jNqjOeJFepyr9yfcXWcM] Spotify: https://open.spotify.com/show/1Bw7KhjlUzFjMoFhdfNAKN [https://open.spotify.com/show/1Bw7KhjlUzFjMoFhdfNAKN] Apple Podcasts: https://podcasts.apple.com/us/podcast/executives-unplugged/id1769131263 [https://podcasts.apple.com/us/podcast/executives-unplugged/id1769131263]

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/ [https://www.linkedin.com/in/meghan-oliver/] Shoutouts RightMove Health: https://rightmovehealth.com [https://rightmovehealth.com] Follow Keith Cowing on LinkedIn: https://linkedin.com/in/keithcowing [https://linkedin.com/in/keithcowing] Join the Executives Unplugged Inner Circle: https://execs.tv [https://execs.tv] Subscribe to the show YouTube: https://www.youtube.com/@execsunplugged [https://www.youtube.com/@execsunplugged] Spotify: https://open.spotify.com/show/1Bw7KhjlUzFjMoFhdfNAKN [https://open.spotify.com/show/1Bw7KhjlUzFjMoFhdfNAKN] Apple Podcasts: https://podcasts.apple.com/us/podcast/executives-unplugged/id1769131263 [https://podcasts.apple.com/us/podcast/executives-unplugged/id1769131263]

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. CHAPTERS 00:00 — 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/ [https://www.linkedin.com/in/mattblumberg/] Shoutouts Startup Boards: https://www.amazon.com/Startup-Boards-Building-Effective-Directors/dp/111985928X [https://www.amazon.com/Startup-Boards-Building-Effective-Directors/dp/111985928X] Markup AI: https://markup.ai [https://markup.ai] Fred Wilson: https://avc.xyz [https://avc.xyz] Mike Collins: https://www.linkedin.com/in/mike-collins-362100/ [https://www.linkedin.com/in/mike-collins-362100/] Follow Keith Cowing on LinkedIn: https://linkedin.com/in/keithcowing [https://linkedin.com/in/keithcowing] Join the Executives Unplugged inner circle: https://kc.coach [https://kc.coach] Subscribe to the show: YouTube — https://www.youtube.com/@kcowing [https://www.youtube.com/@kcowing] Spotify — https://open.spotify.com/show/1Bw7KhjlUzFjMoFhdfNAKN [https://open.spotify.com/show/1Bw7KhjlUzFjMoFhdfNAKN] Apple Podcasts — https://podcasts.apple.com/us/podcast/executives-unplugged/id1769131263 [https://podcasts.apple.com/us/podcast/executives-unplugged/id1769131263]