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.

• 💬 Be interested, not interesting. Shift the spotlight to the customer; that’s where trust begins.

• 🧠 Reps build mastery. Like athletes and artists, salespeople get better through repetition and reflection — not theory.

• 🔥 Authenticity beats polish. When you lead with genuine curiosity and passion, selling stops feeling like selling.

• 🎥 Personal brand is leverage. Jake shows how documenting your story builds trust and visibility that lasts beyond any one deal.

• 💡 The right views matter more than viral views. You don’t need a million followers — you need the right audience.

• Jake and I also talk about the business of creativity — how he learned to blend craft with commerce, the value of expertise (“knowing where to tap”), and why every creator, seller, and leader needs to believe in what they’re offering.

  It’s a fun, high-energy conversation about where art meets revenue — and how showing up as yourself is the real competitive edge.

  🎧 Give it a listen, and let me know what lands with you.

  #SalesLeadership #PersonalBranding #AuthenticSelling #Storytelling #ThoughtsOnSelling

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:

• Sales is psychology. Understanding what makes buyers tick — their motivations, fears, and goals — is at the heart of effective selling.

• AI can’t replace empathy. The best sales reps will use AI as a tool but rely on human insight and curiosity to create connection.

• Coaching and practice drive performance. The highest-performing teams make time to practice and coach — not just inspect pipelines.

• Leaders must define “what good looks like.” Without clear frameworks, coaching and development can’t happen effectively.

• Data makes conversations objective. When performance data is visible, reps and leaders can focus on solving problems together, not defending opinions.

• Curiosity beats scripts. Great sellers ask one more question instead of firing back with a pre-rehearsed answer.

We wrap by talking about the future of sales enablement — one where data, AI, and human insight combine to make teams more adaptable, empathetic, and effective.

🎧 Give it a listen — and let me know what resonates most with you.

#SalesEnablement #SalesLeadership #AIinSales #PsychologyofSelling #ThoughtsOnSelling

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 tell when you’re real — and they reward it.

• AI can’t replace relationships. Tools help, but risk management and shared experience still come from humans.

• Deliberate practice matters. Salespeople need to rehearse pivots and build confidence outside scripts.

• Non-attachment to outcomes frees you. Curiosity and care create openings, even if they don’t lead to immediate deals.

• Great leaders go first. Vulnerability and empathy from the top invite teams to bring their full selves.

This conversation is packed with stories, insights, and practical wisdom for anyone looking to level up as a sales leader or seller.

🎧 Give it a listen, and let me know what lands with you.