Thoughts on Selling YouTube Video Library

In this episode of Thoughts on Selling, I sit down with Lauren Bailey, one of the most dynamic voices in modern sales leadership. She’s the founder of Factor 8 (award-winning inside sales training), #GirlsClub (empowering women in revenue roles), and Legacy VIP (a community for seasoned executives who crave purpose and authentic connection). What starts as a conversation about leadership quickly turns into something deeper — a raw, funny, and inspiring dialogue about who we are and why we do what we do. Lauren shares how losing her best friend became the catalyst for creating Legacy, a space where executives can show up as their whole selves — not just their résumés. She also talks about integrity, self-awareness, and the power of human connection — lessons drawn from personal experience, Landmark Forum, and years of leading sales teams worldwide. 🧭 Key Themes & Lessons - Show up and say yes. These two rules, says Lauren, change everything — in leadership, friendship, and sales. …

In this episode of Thoughts on Selling, I sit down with Kevin Hubschmann, a former enterprise software rep turned comedian and founder of Laugh.Events — a company literally delivering “Laughter as a Service.” We dig into the parallels between improv, comedy, and enterprise sales, exploring how humor, presence, and curiosity can transform the way we connect with customers. Kevin shares his story of balancing daytime sales calls with nighttime comedy clubs, and how the two worlds collided to shape his philosophy on sales as performance and connection. Key themes: - Listening is better than Talking. Kevin breaks down why most sales calls fail because reps talk too much — and how mastering silence is the first step to earning trust - F your good idea. (Yes, really.) In improv and in sales, the goal isn’t to deliver your rehearsed pitch — it’s to respond to what’s actually happening in the moment - Yes, And… We explore how collaboration — not control — drives great sales conversati…

In this episode of Thoughts on Selling, I sit down with Jake Isham — filmmaker, creative director, and founder of Creative Minds Agency. Jake’s story is pure art-meets-entrepreneurship. He started as an actor, moved behind the camera to direct, and somewhere along the way became what he calls an “accidental marketer.” We dig deep into the intersection of storytelling, sales, and authenticity — how great art and great selling share the same purpose: to create an effect. Jake explains how the best salespeople are actually performers — not in a fake way, but in the sense that they listen, adapt, and stay present in the scene. Our conversation bounces between filmmaking, improv, and enterprise sales, but it all comes back to one central idea: sales is an art form. The goal isn’t to pitch harder or talk faster; it’s to create a feeling that sticks. A few big takeaways: 🎭 Sales and acting share the same core skill — presence. Great sellers listen, improvise, and respond in the moment. …

In this episode of Thoughts on Selling, I sit down with Laura Keith, CEO of Hive Perform and Hive Learning — and self-proclaimed “Chief Entertainment Officer” of three kids. We dig into the psychology of selling, the human side of enablement, and how data, AI, and coaching are reshaping modern sales. Laura’s journey from studying psychology to leading sales organizations is fascinating. She never planned to work in sales — but curiosity, empathy, and a deep understanding of human behavior naturally pulled her in. Those same traits now shape her leadership and the products she’s building at Hive Perform. We talk about how sales has lost touch with its human side — too often focused on product features and process over people — and how AI might actually help bring humanity back into selling. As automation handles more of the science, the art becomes more valuable: listening deeply, reading motivation, and understanding buyer psychology. A few big takeaways from our conversation: - …

In this episode of Thoughts on Selling, I sit down with Laura Keith, CEO of Hive Perform and Hive Learning — and self-proclaimed “Chief Entertainment Officer” of three kids. We dig into the psychology of selling, the human side of enablement, and how data, AI, and coaching are reshaping modern sales. Laura’s journey from studying psychology to leading sales organizations is fascinating. She never planned to work in sales — but curiosity, empathy, and a deep understanding of human behavior naturally pulled her in. Those same traits now shape her leadership and the products she’s building at Hive Perform. We talk about how sales has lost touch with its human side — too often focused on product features and process over people — and how AI might actually help bring humanity back into selling. As automation handles more of the science, the art becomes more valuable: listening deeply, reading motivation, and understanding buyer psychology. A few big takeaways from our conversation: - …

In this episode of Thoughts on Selling, I sit down with Jeff Kirchick — sales leader, author, and big believer in authenticity. We dig into how authenticity plays out in sales, what AI can and can’t replace, and why building trust matters more than ever. Jeff shares his journey from English major and aspiring screenwriter to startup sales leader, selling seven-figure deals to Fortune 500s. We talk about his book, the hard truths he learned writing it, and why he believes authenticity is the ultimate differentiator in a world where AI can generate scripts, emails, and playbooks. We get into some fun and unexpected territory too — from Dennis Rodman and Larry David as surprising role models for authenticity, to the cultural differences between selling in Boston, Japan, and Boulder. The through-line? Real relationships, built on curiosity, honesty, and non-attachment to outcomes, are what drive sustainable success in sales. A few key takeaways: - Authenticity builds trust. Buyers can…

In this episode of Thoughts on Selling, I sit down with David Donlan, VP of Sales at IP Co-Pilot, longtime tech sales leader, and passionate mentor for the next generation of sales professionals. David and I cover a wide range of topics — from his early days upselling azaleas with fertilizer at age 15 to shaping sales teams at HubSpot, and now building a company that helps innovators protect and accelerate patents. A few highlights from our conversation: - Three ways to sell. David breaks down selling on product (easy but competitive), outcomes (about solving real business problems), and feelings (the hardest, but most powerful when done well). - The heart of leadership. Why helping SDRs and junior salespeople grow into leaders is one of the most rewarding parts of a career. - Hiring with discipline. Scorecards, structured onboarding, and clear expectations turn hiring from a gamble into a repeatable, measurable process. - Culture in action. It’s not about slogans on the wal…

A brief trailer for the Ted McKenna podcast

In this episode of Thoughts on Selling, I sit down with Ted McKenna — researcher, author, and co-creator of some of the most influential sales frameworks of the past two decades. Ted has been behind The Challenger Sale, The JOLT Effect, and most recently, The Activator Advantage. Our conversation dives into the evolving dynamics of B2B sales, why buyers are more informed (and more hesitant) than ever, and what high-performing sellers do differently. We discuss: 👍 Data meets sales anthropology. Ted shares how deep analysis of 2.5 million sales calls revealed why more deals end in “no decision” — and what sellers can do about it. 👍 The JOLT Effect in practice. Why too much information overwhelms buyers, and how great sellers guide decisions rather than flood inboxes with decks. 👍 The Activator Advantage. A deep look at what makes “activators” so successful — consistent business development, building zipper relationships, and flowing value across networks. 👍 Fear of messing up.…

In this episode of Thoughts on Selling, I sit down with AI strategist and workforce transformation expert Ben Tasker. Ben has spent over a decade helping organizations harness AI not just as a shiny tool, but as a way to amplify human abilities through upskilling, reskilling, and smarter systems thinking. We dive into: The “AI Between Times”: why we’re in a transition period where adoption is fast, mistakes will happen, and systems thinking is essential. Upskilling & Reskilling: how organizations can build learning plans to keep talent relevant and amplify what people already do well. Applied AI in Sales: from RFP prep to simulated buyer conversations, how sales teams can use AI for deliberate practice and better customer engagement. Systems Thinking & Change Management: why AI adoption fails without clear processes, data quality, and organizational alignment. Personal Branding in the AI Era: how individuals can leverage AI to publish, create, and stay visible in a world where r…