The Advanced Selling Podcast

The Advanced Selling Podcast

By Bill Caskey and Bryan Neale: B2B Sales TrainersBusinessEducationSelf-ImprovementMarketing
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The Advanced Selling Podcast episodes

  • From Content to Conquest

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    Bill and Bryan are giving you a preview of the March 6th ASP Insider session — and it's one you don't want to miss.

    The topic is From Content to Conquest, but this isn't a social media training. It's about what you know, what you believe, and how you package your expertise so prospects say, "I want to know more."

    Before diving into the March session, Bill and Bryan walk through the perspective shifts that have to happen first — because you can know exactly what to do and still not do it. The missing ingredient is almost always how you see things.

    Plus, Bryan shares how the Mental Health for Salespeople series resonated far beyond the sales world — and what that buzz means for upcoming episodes.

    The Insider program is open for enrollment. To check out our small learning group, go to http://advancedsellingpodcast.com/insider

    If you haven't already, join 14,000+ other sales professionals in our LinkedIn group at advancedsellingpodcast.com/linkedin

    Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrets to Reinventing Yourself and Your Business." http://12boldmoves.com

    20 min
  • Why Collaboration Beats Closing Tactics Every Time

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    What if your entire sales process—from networking to contract signing—was built on collaboration instead of persuasion? 

    In this episode, Bill and Bryan break down what real collaboration looks like at every stage: pre-sale networking, early conversations, mid-stage resistance, and closing deals. You'll discover why most salespeople avoid collaboration (they're afraid of conflict), how to audit your sales process for collaborative moments, and the simple phrase that sets the tone from day one. 

    Bill shares a client story about refusing to send a proposal until they collaborated on unanswered questions—and how it built immediate trust. 

    Whether you're stuck in transactional mode or ready to differentiate yourself completely, this episode gives you a new through line that actually works.

    Join the conversation: AdvancedSellingPodcast.com/linkedin

    Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrets to Reinventing Yourself and Your Business." http://12boldmoves.com

    The Insider program is open for enrollment. To check out our small learning group, go to http://advancedsellingpodcast.com/insider

    21 min
  • Saving Sales Time with Smarter Routes ft. Steve Benson

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    In this episode of The Advanced Selling Podcast, Bryan Neale welcomes Steve Benson, founder of Badger Maps, for a conversation on why outside sales teams are often overlooked by modern sales technology — and what happens when tools are finally built with field sellers in mind.

    Bryan and Steve dig into the realities of territory design and route planning, calling out how many sales leaders still rely on gut feel and educated guesses when structuring territories. Steve explains how Badger Maps and Badger Align help sales teams visualize customers geographically, balance territories using real data, and create more efficient routes that lead to more meetings and measurable sales lift. They also explore why mobile-friendly CRM tools matter so much for outside sellers, and how removing friction from data entry in the field directly impacts performance.

    The conversation expands into Badger Maps’ broader platform, including lead routing, geographic insights, and performance tracking, before Steve shares the origin story behind the product — a firsthand realization that sales data is far more powerful when you can see it on a map.

    _______

    Curious about certification in the Blind Zebra Sales Operating System? Learn more here.

    27 min
  • Is Your Through Line Costing You Business?

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    What can Charlie Puth's collaboration with Kenny G for the Super Bowl national anthem teach us about sales? More than you'd think.

    Bill and Bryan break down the story of how Charlie Puth persistently pursued Kenny G—not through aggressive follow-ups, but through generous, creative demonstrations of value. He sent tracks. He added a choir. He painted the picture so vividly that Kenny G couldn't help but respond.

    The sales lessons are everywhere: Clean intention enables authentic persistence. Information isn't proprietary anymore, so stop withholding it. Collaboration beats competition. And most importantly, your "through line"—the underlying driver of your sales process—might be sabotaging your success.

    Most sales methodologies operate on a selfish through line: What do I need to say or do to get the deal? That approach creates manipulation, defensiveness, and resistance. But what if collaboration was your through line instead?

    Join the conversation: AdvancedSellingPodcast.com/linkedin

    Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrets to Reinventing Yourself and Your Business." http://12boldmoves.com

    The Insider program is open for enrollment. To check out our small learning group, go to http://advancedsellingpodcast.com/insider

    19 min
  • Be the Guide Your Customers Are Craving

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    Bill Caskey explores the most important question in sales: What is your role in the buyer-seller dance?

    In this solo episode, Bill breaks down the Guide Model—a three-part framework that transforms how you show up with customers. Instead of selling to people who don't need what you offer, you become the guide that customers are craving.

    If you've ever wondered why buyers don't trust you or why price becomes the sticking point, this episode reveals what's really happening—and how to fix it.

    This is part 2 of a 2-part series on how to be a guide.

    🔗 Want more advanced sales training? Join ASP Insider: https://advancedsellingpodcast.com/insider

    Download your complimentary copy of the 12 Bold Moves audiobook at 12BoldMoves.com/Audiobook

    8 min
  • Mental Health in Sales: Movement Creates Momentum

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    In the final episode of our mental health in sales series, Bill and Bryan tackle a truth most sellers ignore: you can't think your way out of a slump—you have to move your way out.

    Drawing from Scott Galloway's "get out of the house" philosophy and real client stories, they explore how physical action—whether it's actual exercise or the behavioral action of getting out and connecting with people—breaks the isolation cycle that feeds sales depression.

    Bill shares a coaching win where an engineer went from zero prospecting hours to booking two appointments just by reaching out to reconnect with old contacts. No pitch, no agenda—just human connection. 

    Whether you're feeling stuck, isolated, or just going through the motions, this episode delivers the kick you need to stop overthinking and start moving.

    This is Part 4 of our Mental Health in Sales series. Find all episodes at https://vault.advancedsellingpodcast.com/mental-health-in-sales

    Join the conversation: AdvancedSellingPodcast.com/linkedin

    Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrets to Reinventing Yourself and Your Business." http://12boldmoves.com

    The Insider program is open for enrollment. To check out our small learning group, go to http://advancedsellingpodcast.com/insider

    25 min
  • How Detachment Creates Sales Freedom

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    In this solo episode, Bill breaks down why detachment might be the most important skill you're not practicing. When a client asked for help with negotiation, positioning, and value communication, Bill realized all these challenges stem from one core issue: attachment to outcomes.

    Discover why healthy detachment isn't about not caring—it's about being deliberate in your process without getting entangled in results. Bill explains how attachment creates fear, shortcuts, and procrastination, while detachment creates freedom and effectiveness.

    This is part 1 of a 2-part series. Next week: How to be the guide.

    🔗 Want more advanced sales training? Join ASP Insider: https://advancedsellingpodcast.com/insider

    Download your complimentary copy of the 12 Bold Moves audiobook at 12BoldMoves.com/Audiobook

    6 min
  • Scaling Authenticity in Sales with John Wechsler

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    In this episode of The Advanced Selling Podcast, Bryan Neale is joined by John Wechsler, CEO of Spokenote, for a conversation on why authentic, personalized video is becoming a critical advantage for modern sales teams.

    Bryan and John discuss the difference between messaging and moments, emphasizing that when the moment matters more than the message, authenticity wins. John shares the evolution of Spokenote, from a simple sticker concept to a dynamic video platform, driven by real demand for scalable personalization. They unpack what truly differentiates Spokenote from other video tools: modular, variable video snippets that allow sellers to personalize outreach while staying efficient and fully integrated with existing CRM workflows.

    The conversation also tackles one of the biggest barriers to video adoption in sales: hesitation and self-consciousness. John encourages sales professionals to embrace imperfection, reminding listeners that vulnerability often increases trust and likability.

    __

    Curious about certification in the Blind Zebra Sales Operating System? Learn more here.

    21 min
  • Mental Health in Sales: Detachment, Service and Personal Agency

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    In part 3 of the mental health series, Bill and Bryan tackle the achievement trap that plagues high performers: when is enough enough? 

    They introduce six practical frameworks for managing mental health in sales, covering the first three in depth: detachment from outcomes, obsessive focus on customer problems, and personal agency. Bill addresses a high performer's legitimate concern about whether detachment actually helps or hurts quota achievement, and Bryan shares insights from John Mellencamp's conversation with Joe Rogan about success and happiness. 

    The episode includes the concept of "measuring backwards" and explains why serving customers beats obsessing over your own numbers.

    Join the conversation: AdvancedSellingPodcast.com/linkedin

    Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrets to Reinventing Yourself and Your Business." http://12boldmoves.com

    The Insider program is open for enrollment. To check out our small learning group, go to http://advancedsellingpodcast.com/insider

    If you haven't already, join 14,000+ other sales professionals in our LinkedIn group at advancedsellingpodcast.com/linkedin

    29 min
  • Mental Health in Sales: Confidence, Purpose and Movement

    Send us Fan Mail

    In part 2 of our mental health series, Bill and Bryan explore what creates genuine confidence in sales and why it starts with something bigger than yourself. 

    They discuss the "divine assignment" concept, finding meaning in your work beyond financial gain, and how physical movement directly impacts emotional health. 

    If you struggle with walking on eggshells around buyers or feel desperate for outcomes, this episode offers practical remedies including discovering your purpose and becoming obsessed with customer problems instead of deal outcomes.

    Join the conversation: AdvancedSellingPodcast.com/linkedin

    Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrets to Reinventing Yourself and Your Business." http://12boldmoves.com

    The Insider program is open for enrollment. To check out our small learning group, go to http://advancedsellingpodcast.com/insider

    If you haven't already, join 14,000+ other sales professionals in our LinkedIn group at advancedsellingpodcast.com/linkedin

    27 min

About The Advanced Selling Podcast

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Bill Caskey and Bryan Neale deliver practical, no-nonsense sales training through their signature blend of humor, real-world insights, and actionable frameworks. Each episode tackles the challenges…

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