Executives Unplugged

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...

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...

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...

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 s...

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...

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 strateg...

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 “e...

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 com...

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 —...

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 pi...

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 "Produ...

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...

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 c...

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....

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...

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: runni...

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...

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 strat...

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 t...

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...